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(R)-metamphetamine + NADPH + H+ + O2
(R)-metamphetamine N-oxide + NADP+ + H2O
-
substrate of isoform FMO1
-
-
?
(S)-metamphetamine + NADPH + H+ + O2
(S)-metamphetamine N-oxide + NADP+ + H2O
-
substrate of isoforms FMO1 and FMO3
-
-
?
(S)-nicotine + NADPH + H+ + O2
?
-
-
-
-
?
(S)-nicotine + NADPH + O2
(S)-nicotine N1-oxide + NADP+ + H2O
-
(S)-nicotine N-1'-oxygenation
-
-
?
1,1-dimethylhydrazine + NADPH + O2
formaldehyde + CH3N2H3 + NADP+
1,2,3,4-tetrahydroisoquinoline + NADPH + O2
?
1,2-dimethylhydrazine + NADPH + H+ + O2
1,2-dimethylhydrazine N-oxide + NADP+ + H2O
-
-
-
-
r
1,2-dimethylhydrazine + NADPH + O2
?
1,2-dimethylphenylhydrazine + NADPH + O2
?
1-butanethiol + NADPH + O2
?
1-methyl-1-phenylhydrazine + NADPH + O2
?
1-methyl-2-benzylhydrazine + NADPH + H+ + O2
1-methyl-2-benzylhydrazine N-oxide + NADP+ + H2O
-
-
-
-
r
1-methyl-2-benzylhydrazine + NADPH + O2
?
1-methyl-2-thioimidazole + NADPH + O2
?
-
-
-
-
?
1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine + NADPH + H+ + O2
1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine N-oxide + NADP+ + H2O
1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine + NADPH + O2
?
1-methyl-6,7-dihydroxytetrahydroisoquinoline + NADPH + O2
?
-
-
-
-
?
1-[4-(methylsulfanyl)phenyl]ethanone + NADPH + H+ + O2
(R,S)-1-[4-(methylsulfanyl)phenyl]ethanone S-oxide + NADP+ + H2O
10-(N,N-dimethylaminoalkyl)-2-(trifluoromethyl) phenothiazines + NADPH + O2
?
10-(N,N-dimethylaminooctyl)2-(trifluoromethyl)phenothiazene + NADPH + H+ + O2
? + NADP+ + H2O
10-(N,N-dimethylaminooctyl)2-(trifluoromethyl)phenothiazine + NADPH + H+ + O2
10-(N,N-dimethylaminooctyl)2-(trifluoromethyl)phenothiazine N-oxide + NADP+ + H2O
-
-
-
r
10-(N,N-dimethylaminopentyl)-2-(trifluoromethyl)phenothiazine + NADPH + O2
?
10-([N,N-dimethylaminopentyl]-2-trifluoromethyl)phenothiazine + NADPH + O2
?
-
-
-
-
?
10-N-(n-octylamino)-2-(trifluoromethyl) phenothiazine + NADPH + O2
10-N-(n-octylamino)-2-(trifluoromethyl) phenothiazine N-oxide + NADP+ + H2O
10-[(N,N-dimethylaminooctyl)-2-(trifluoromethyl)]phenothiazine + NADPH + H+ + O2
10-[(N,N-dimethylaminooctyl)-2-(trifluoromethyl)]phenothiazine N-oxide + NADP+ + H2O
-
-
-
-
?
10-[(N,N-dimethylaminopentyl)-2-(trifluoromethyl)]phenothiazine + NADPH + O2
?
-
i.e. 5-DPT or diethylenetriaminepentaacetic acid
-
-
?
2 bicyclo[4.2.0]octan-7-one + 2 NADH + 2 H+ + 2 O2
(3aS,7aS)-hexahydro-1-benzofuran-2(3H)-one + (3aR,7aS)-hexahydro-2-benzofuran-1(3H)-one + 2 NAD+ + 2 H2O
-
-
-
-
?
2,4,5-trichlorphenol + O2
2,5-dichlorohydroquinone + H2O + Cl-
2,4,6-trichlorphenol + O2
2,6-dichlorohydroquinone + H2O + Cl-
2,4-dichlorphenol + O2
chlorohydroquinone + H2O + Cl-
2-(methylsulfanyl)pyridine + NADPH + H+ + O2
2-(methylsulfanyl)pyridine S-oxide + NADP+ + H2O
2-(methylsulfanyl)thiophene + NADPH + H+ + O2
2-(methylsulfanyl)thiophene S-oxide + NADP+ + H2O
2-acetylsulfanylmethyl-4-(4-methoxyphenyl)-4-oxobutyric acid + NADPH + H+ + O2
?
-
-
-
-
?
2-chlorophenol + O2
chlorohydroquinone + H2O
2-chlorophenyl methyl sulfide + NADPH + H+ + O2
(R,S)-2-chlorophenyl methyl sulfide S-oxide + NADP+ + H2O
2-mercaptobenzimidazole + NADPH + O2
?
2-[(methylsulfanyl)methyl]furan + NADPH + H+ + O2
2-[(methylsulfanyl)methyl]furan S-oxide + NADP+ + H2O
-
sulfoxidation by recombinant PTDH-mFMO fusion protein
-
-
?
2-[2-(4-methoxyphenyl)-2-oxoethyl]-acrylic acid + NADPH + H+ + O2
?
-
a synthetic 10-(N,N-dimethylaminoalkyl)-2-(trifluoromethyl)phenothiazine analogue
-
-
?
3-chlorophenyl methyl sulfide + NADPH + H+ + O2
(R,S)-3-chlorophenyl methyl sulfide S-oxide + NADP+ + H2O
-
sulfoxidation of the thioanisole derivative by recombinant PTDH-mFMO fusion protein. Enantiomeric reaction with 15% R-enantiomer as product
-
-
?
3-hydroxy-nabumetone + NADPH + H+ + O2
? + NADP+ + H2O
activation reaction
-
-
?
4-(4-methoxyphenyl)-2-methylsulfanylmethyl-4-oxobutyric acid + NADPH + H+ + O2
?
-
FMO1, poor activity with FMO3 and FMO5
-
-
?
4-(4-methylphenyl)-2-methylsulfanylmethyl-4-oxobutyric acid + NADPH + H+ + O2
?
-
FMO1 and FMO5, no activity with FMO3
-
-
?
4-(methylsulfanyl)benzonitrile + NADPH + H+ + O2
(R,S)-4-(methylsulfanyl)benzonitrile S-oxide + NADP+ + H2O
-
sulfoxidation of the thioanisole derivative by recombinant PTDH-mFMO fusion protein. Enantiomeric reaction with 22% S-enantiomer as product
-
-
?
4-(methylsulfanyl)phenol + NADPH + H+ + O2
(R,S)-4-(methylsulfanyl)phenol S-oxide + NADP+ + H2O
-
sulfoxidation of the thioanisole derivative by recombinant PTDH-mFMO fusion protein. Enantiomeric reaction with 81% S-enantiomer as product
-
-
?
4-aminobenzoic acid hydrazide + NADPH + O2
?
-
-
-
?
4-chlorophenol + O2
hydroquinone + H2O + Cl-
4-chlorophenyl methyl sulfide + NADPH + H+ + O2
(R,S)-4-chlorophenyl methyl sulfide S-oxide + NADP+ + H2O
-
sulfoxidation of the thioanisole derivative by recombinant PTDH-mFMO fusion protein. Enantiomeric reaction with 95% S-enantiomer as product
-
-
?
5,6-dimethylxanthenone-4-acetic acid + NADPH + H+ + O2
?
-
substrate of isoform FMO3, methyl hydroxylation
-
-
?
5-[[3-(dimethylamino)propyl]amino]-8-hydroxy-6H-[1,2,3]triazolo[4,5,1-de]acridin-6-one + NADPH + H+ + O2
5-[[3-(dimethylnitroryl)propyl]amino]-8-hydroxy-6H-[1,2,3]triazolo[4,5,1-de]acridin-6-one + NADP+ + H2O
5-[[3-(dimethylamino)propyl]amino]-8-methoxy-6H-[1,2,3]triazolo[4,5,1-de]acridin-6-one + NADPH + H+ + O2
5-[[3-(dimethylnitroryl)propyl]amino]-8-methoxy-6H-[1,2,3]triazolo[4,5,1-de]acridin-6-one + NADP+ + H2O
9-hydroxy-5,6-dimethyl-N-(2-(dimethylamino)ethyl)-6H-pyrido(4,3-B)-carbazole-1-carboxamide + NADPH + H+ + O2
2-(9-hydroxy-5,6-dimethyl-6H-pyrido[4,3-b]carbazole-1-carboxamido)-N,N-dimethylethan-1-amine oxide + NADP+ + H2O
-
substrate of isoform FMO3
-
-
?
albendazole + NADPH + H+ + O2
albendazole S-oxide + NADP+ + H2O
-
substrate of isoform FMO3
-
-
?
aldicarb + NADPH + O2
?
-
-
-
-
?
almotriptan + NADPH + H+ + O2
almotriptan N-oxide + NADP+ + H2O
-
substrate of isoform FMO3
-
-
?
alpha-naphthylthiourea + NADPH + O2
?
aminopyrine + NADPH + O2
?
ammonia + NADPH + H+ + O2
? + NADP+ + H2O
-
-
-
-
?
amphetamine + NADPH + H+ + O2
?
amphetamine + NADPH + H+ + O2
amphetamine N-oxide + NADP+ + H2O
-
substrate of isoform FMO3
-
-
?
amphetamine + NADPH + O2
amphetamine N-oxide + NADP+ + H2O
-
-
-
-
?
benzydamine + NADPH + H+ + O2
?
-
i.e. 3-(1-benzyl-1H-indazol-3-yloxy)-N,N-dimethylpropan-1-amine
-
-
?
benzydamine + NADPH + H+ + O2
benzydamine N-oxide + NADP+ + H2O
benzydamine + NADPH + O2
benzydamine N-oxide + NADP+ + H2O
benzyl ethyl sulfide + NADPH + H+ + O2
benzyl ethyl sulfide S-oxide + NADP+ + H2O
-
sulfoxidation by recombinant PTDH-mFMO fusion protein
-
-
?
benzyl methyl sulfide + NADPH + H+ + O2
benzyl methyl sulfide S-oxide + NADP+ + H2O
-
sulfoxidation by recombinant PTDH-mFMO fusion protein
-
-
?
benzylamine + [reduced NADPH-hemoprotein reductase] + O2
benzylamine N-oxide + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
-
-
?
benzylhydrazine + NADPH + H+ + O2
benzylhydrazine N-oxide + NADP+ + H2O
-
-
-
-
r
benzylhydrazine + NADPH + O2
?
beta-ethylphenylhydrazine + NADPH + H+ + O2
beta-ethylphenylhydrazine N-oxide + NADP+ + H2O
-
-
-
-
r
beta-ethylphenylhydrazine + NADPH + O2
?
bicyclo[3.2.0]hept-2-en-6-one + NADH + H+ + O2
?
-
-
-
-
?
bicyclo[3.2.0]hept-2-en-6-one + NADPH + H+ + O2
?
-
-
-
-
?
bupivacaine + NADPH + O2
bupivacaine-oxide + NADP+
-
-
-
-
?
butyl ethyl sulfide + NADPH + H+ + O2
butyl ethyl sulfide S-oxide + NADP+ + H2O
-
sulfoxidation by recombinant PTDH-mFMO fusion protein
-
-
?
butyl methyl sulfide + NADPH + H+ + O2
butyl methyl sulfide S-oxide + NADP+ + H2O
-
sulfoxidation by recombinant PTDH-mFMO fusion protein
-
-
?
butylhydrazine + NADPH + H+ + O2
butylhydrazine N-oxide + NADP+ + H2O
-
-
-
-
r
butylhydrazine + NADPH + O2
?
chlorpromazine + NADPH + H+ + O2
chlorpromazine N-oxide + NADP+ + H2O
chlorpromazine + NADPH + H+ + O2
chlorpromazine oxide + NADP+ + H2O
-
-
-
-
?
chlorpromazine + NADPH + O2
?
chlorpromazine + NADPH + O2
chlorpromazine N-oxide + NADP+ + H2O
-
-
-
-
?
cimetidine + NADPH + H+ + O2
cimetidine S-oxide + NADP+ + H2O
cimetidine + NADPH + O2
cimetidine S-oxide + NADP+ + H2O
-
-
-
-
?
clomiphene + NADPH + H+ + O2
?
-
i.e. 2-[4-[2-chloro-1,2-diphenylethenyl]phenoxy]-N,N-diethylethanamine
-
-
?
clomiphene + NADPH + H+ + O2
clomiphene N-oxide + NADP+ + H2O
clomipramine + NADPH + H+ + O2
clomipramine N-oxide + NADP+ + H2O
-
-
-
?
clozapine + NADPH + H+ + O2
?
-
-
-
-
?
clozapine + NADPH + H+ + O2
clozapine N-oxide + NADP+ + H2O
clozapine + NADPH + O2
?
-
-
-
-
?
contezolid + NADPH + H+ + O2
contezolid N-oxide + NADP+ + H2O
-
substrate of isoform FMO5
-
-
?
cyclobutanone + NADH + H+ + O2
gamma-butyrolactone + NAD+ + H2O
-
-
-
-
?
cyclohexyl methyl sulfide + NADPH + H+ + O2
cyclohexyl methyl sulfide S-oxide + NADP+ + H2O
-
sulfoxidation by recombinant PTDH-mFMO fusion protein
-
-
?
cysteamine + NADPH + H+ + O2
?
cysteamine + NADPH + O2
?
cysteamine + NADPH + O2
cysteamine N-oxide + NADP+ + H2O
danusertib + NADPH + H+ + O2
danusertib N-oxide + NADP+ + H2O
-
substrate of isoform FMO3
-
-
?
dasatinib + NADPH + H+ + O2
4-(6-((5-((2-chloro-6-methylphenyl)carbamoyl)thiazol-2-yl)amino)-2-methylpyrimidin-4-yl)-1-(2-hydroxyethyl)piperazine 1-oxide + NADP+ + H2O
-
substrate of isoform FMO3
-
-
?
dasatinib + NADPH + H+ + O2
dasatinib N-oxide + NADP+ + H2O
-
-
-
?
demeton-O + NADPH + O2
demeton-O sulfoxide + NADP+ + H2O
deprenyl + NADPH + H+ + O2
?
deprenyl + NADPH + H+ + O2
deprenyl N-oxide + NADP+ + H2O
-
substrate of isoforms FMO1 and FMO3
-
-
?
dibenzylamine + NADPH + O2
?
dihydrolipoic acid + NADPH + O2
?
-
-
-
-
?
dimethylsulfone + NADH + H+ + O2
methanesulfinate + NAD+ + H2O
disulfoton + NADPH + H+ + O2
?
E-7016 + NADPH + H+ + O2
?
-
substrate of isoform FMO5, Bayer Villiger oxidation
-
-
?
esonarimod + NADPH + H+ + O2
S-methyl esonarimod + NADP+ + H2O
a antirheumatic drug, is converted to the S-oxide
-
-
?
ethiofencarb + NADPH + O2
ethiofencarb sulfoxide + NADP+ + H2O
ethionamide + NADPH + H+ + O2
?
ethionamide + NADPH + H+ + O2
ethionamide N-oxide + NADP+ + H2O
ethionamide + NADPH + H+ + O2
ethionamide S-oxide + NADP+ + H2O
ethionamide + NADPH + O2 + H+
2-ethyl-N-hydroxypyridine-4-carbothioamide + NADP+ + H2O
ethyl phenyl sulfide + NADPH + H+ + O2
ethyl phenyl sulfoxide + NADP+ + H2O
-
sulfoxidation by recombinant PTDH-mFMO fusion protein
-
-
?
ethylene sulfide + NADPH + O2
?
ethylene thiourea + NADPH + H+ + O2
?
-
-
-
-
?
ethylenethiourea + NADPH + O2
ethylenethiourea S-oxide + NADP+ + H2O
-
-
-
-
?
ethylenthiourea + NADPH + O2
?
-
-
-
-
?
ethylhydrazine + NADPH + H+ + O2
ethylhydrazine N-oxide + NADP+ + H2O
-
-
-
-
r
etionamide + NADPH + H+ + O2
etionamide S-oxide + NADP+ + H2O
substrate of FMO1, FMO3, and FMO2.1
-
-
?
fenthion + NADPH + O2
fenthion sulfoxide + NADP+
-
-
74% (+)-sulfoxide
-
?
fenthion + NADPH + O2
fenthion sulfoxide + NADP+ + H2O
GSK5182 + NADPH + H+ + O2
(Z)-2-(4-(5-hydroxy-1-(4-hydroxyphenyl)-2-phenylpent-1-en-1-yl)phenoxy)-N,N-dimethylethan-1-amine oxide + NADP+ + H2O
-
substrate of isoforms FMO1 and FMO3
-
-
?
GSK5182 + NADPH + H+ + O2
GSK5182 N-oxide + NADP+ + H2O
hypotaurine + H2O + NAD+
taurine + NADH
hypotaurine + NADH + H+ + O2
taurine + NAD+ + H2O
hypotaurine + NADPH + H+ + O2
taurine + NADP+ + H2O
hypotaurine + O2 + NADH + H+
taurine + NAD+ + H2O
-
-
-
?
hypotaurine + O2 + NADPH + H+
taurine + NADP+ + H2O
-
-
-
?
imipramine + NADPH + H+ + O2
imipramine N-oxide + NADP+ + H2O
imipramine + NADPH + H+ + O2
imipramine oxide + NADP+ + H2O
-
-
-
-
?
imipramine + NADPH + O2
?
imipramine + NADPH + O2
imipramine N-oxide + NADP+ + H2O
indole + NADPH + H+ + O2
indole N-oxide + NADP+ + H2O
indole + NADPH + H+ + O2
indoxyl + NADP+ + H2O
isopropylhydrazine + NADPH + H+ + O2
isopropylhydrazine N-oxide + NADP+ + H2O
-
-
-
-
r
isopropylhydrazine + NADPH + O2
?
itopride + NADPH + H+ + O2
itopride N-oxide + NADP+ + H2O
itopride + NADPH + O2
?
-
-
-
-
?
K11777 + NADPH + H+ + O2
K11777 N-oxide + NADP+ + H2O
L-775,606 + NADPH + H+ + O2
4-(3-(5-(4H-1,2,4-triazol-4-yl)-1H-indol-3-yl)propyl)-1-(3-fluorophenethyl)piperazine 1-oxide + NADP+ + H2O
-
substrate of isoform FMO3
-
-
?
L-Met-Phe + NADPH + O2
(L-Met-S-oxide)-Phe + NADP+ + H2O
L-Met-Val + NADPH + O2
(L-Met-S-oxide)-Val + NADP+ + H2O
L-methionine + NADPH + H+ + O2
?
-
-
-
?
L-methionine + NADPH + H+ + O2
L-methionine S-oxide + NADP+ + H2O
-
-
-
-
?
L-methionine + NADPH + H+ + O2
methionine S-oxide + NADP+ + H2O
stereochemistry, overview
formation of 80% D-isomer
-
?
L-methionine + NADPH + O2
L-methionine S-oxide + NADP+ + H2O
L-Phe-Met + NADPH + O2
(L-Met-S-oxide)-Phe + NADP+ + H2O
-
liver microsomes
-
-
?
L-seleno-methionine + NADPH + O2
L-methionine seleno-oxide + NADP+ + H2O
lidocaine + NADPH + O2
lidocaine-oxide + NADP+
-
-
-
-
?
lipoic acid + NADPH + O2
?
lorcaserin + NADPH + H+ + O2
lorcaserin N-oxide + NADP+ + H2O
-
substrate of isoform FMO1
-
-
?
loxapine + NADPH + H+ + O2
4-(2-chlorodibenzo[b,f][1,4]oxazepin-11-yl)-1-methylpiperazine 1-oxide + NADP+ + H2O
-
substrate of isoform FMO3
-
-
?
loxapine + NADPH + H+ + O2
loxapine N-oxide + NADP+ + H2O
-
-
-
?
mercaptoimidazole + NADPH + H+ + O2
?
-
FMO1 and FMO3, no activity with FMO5
-
-
?
mercaptoimidazole + NADPH + O2
mercaptoimidazole S-oxide + NADP+ + H2O
-
-
-
-
?
methamphetamine + NADPH + H+ + O2
?
methamphetamine + NADPH + H+ + O2
methamphetamine N-oxide + NADP+ + H2O
a psychostimulant, is converted to the hydroxylamine
-
-
?
methamphetamine + NADPH + O2
?
methimazole + NADH + H+
?
-
-
-
?
methimazole + NADPH + H+
?
-
-
-
?
methimazole + NADPH + H+ + O2
?
methimazole + NADPH + H+ + O2
methimazole N-oxide + NADP+ + H2O
methimazole + NADPH + H+ + O2
methimazole S-oxide + NADP+ + H2O
methimazole + NADPH + O2
?
methimazole + NADPH + O2
N-methylmethimidazole-2-sulfinic acid + NADP+ + H2O
methiocarb + NADPH + O2
methiocarb sulfoxide + NADP+ + H2O
methyl 2-phenylethyl sulfide + NADPH + H+ + O2
methyl 2-phenylethyl sulfide S-oxide + NADP+ + H2O
-
sulfoxidation by recombinant PTDH-mFMO fusion protein
-
-
?
methyl 4-(methylsulfanyl)phenyl ether + NADPH + H+ + O2
(R,S)-methyl 4-(methylsulfanyl)phenyl ether S-oxide + NADP+ + H2O
-
sulfoxidation of the thioanisole derivative by recombinant PTDH-mFMO fusion protein. Enantiomeric reaction with 70% S-enantiomer as product
-
-
?
methyl 4-methylphenyl sulfide + NADPH + H+ + O2
(R,S)-methyl 4-methylphenyl sulfide S-oxide + NADP+ + H2O
-
sulfoxidation of the thioanisole derivative by recombinant PTDH-mFMO fusion protein. Enantiomeric reaction with 92% S-enantiomer as product
-
-
?
methyl 4-nitrophenyl sulfide + NADPH + H+ + O2
(R,S)-methyl 4-nitrophenyl sulfide S-oxide + NADP+ + H2O
-
sulfoxidation of the thioanisole derivative by recombinant PTDH-mFMO fusion protein. Enantiomeric reaction with 37% S-enantiomer as product
-
-
?
methyl 4-tolyl sulfide + NADPH + O2
methyl 4-tolyl sulfoxide + NADP+ + H2O
methyl p-tolyl sulfide + NADPH + H+ + O2
?
methyl p-tolyl sulfide + NADPH + O2
methyl p-tolyl sulfoxide + NADP+ + H2O
methyl phenyl sulfide + NADPH + H+ + O2
(R,S)-methyl phenyl sulfoxide + NADP+ + H2O
-
sulfoxidation of the thioanisole derivative by recombinant PTDH-mFMO fusion protein. Enantiomeric reaction with 35% S-enantiomer as product
-
-
?
methyl-4-tolyl sulfide + NADPH + H+ + O2
?
-
-
-
-
?
methylmercaptan + NADPH + H+ + O2
? + NADP+ + H2O
-
-
-
-
?
methylphenylsulfide + NADPH + O2
?
methylthioalkyl glucosinolate + NADPH + H+ + O2
methylsulfinylalkyl glucosinolate S-oxide + NADP+ + H2O
-
-
-
-
?
MK-0457 + NADPH + H+ + O2
MK-0457 N-oxide + NADP+ + H2O
-
substrate of isoforms FMO1 and FMO3
-
-
?
MK-0767 methyl sulfide + NADPH + H+ + O2
?
moclobemide + NADPH + H+ + O2
moclobemide N-oxide + NADP+ + H2O
-
substrate of isoform FMO3
-
-
?
N,N,N-trimethylamine + NADPH + H+ + O2
N,N,N-trimethylamine N-oxide + NADP+ + H2O
-
-
-
?
N,N-diallyltryptamine + NADPH + H+ + O2
N,N-diallyltryptamine N-oxide + NADP+ + H2O
-
substrate of isoform FMO3
-
-
?
N,N-dimethyl-3-[2-(trifluoromethyl)-10H-phenothiazin-10-yl]propan-1-amine + NADPH + H+ + O2
?
-
3-DPT, a phenothiazine analogue, N-oxygenation by FMO1 and FMO3, no activity with FMO5
-
-
?
N,N-dimethyl-5-[2-(trifluoromethyl)-10H-phenothiazin-10-yl]pentan-1-amine + NADPH + H+ + O2
?
-
5-DPT, a phenothiazine analogue, N-oxygenation by FMO1, FMO3, and FMO5
-
-
?
N,N-dimethyl-8-[2-(trifluoromethyl)-10H-phenothiazin-10-yl]octan-1-amine + NADPH + H+ + O2
?
-
8-DPT, a phenothiazine analogue, N-oxygenation by FMO1, FMO3, and FMO5
-
-
?
N,N-dimethylamphetamine + NADPH + H+ + O2
N,N-dimethylamphetamine N-oxide + NADP+ + H2O
N-oxygenation mainly by isozyme FMO1, low activity with isozyme FMO3
-
-
?
N,N-dimethylaniline + NADH + H+ + O2
N,N-dimethylaniline N-oxide + NAD+ + H2O
-
-
-
-
?
N,N-dimethylaniline + NADPH + H+ + O2
N,N-dimethylaniline N-oxide + NADP+ + H2O
N,N-dimethylaniline + NADPH + O2
N,N-dimethylaniline N-oxide + NADP+ + H2O
N-(3R)-1-azabicyclo[2.2.2]oct-3-ylfuro[2,3-c]pyridine-5-carboxamide + NADPH + H+ + O2
(R)-3-(furo[2,3-c]pyridine-5-carboxamido)quinuclidine 1-oxide + NADP+ + H2O
-
substrate of isoforms FMO1 and FMO3
-
-
?
N-aminohomopiperidine + NADPH + O2
?
N-aminomorpholine + NADPH + H+ + O2
N-aminomorpholine N-oxide + NADP+ + H2O
-
-
-
-
r
N-aminomorpholine + NADPH + O2
?
N-aminopiperidine + NADPH + O2
?
N-aminopiperidine + NADPH + O2
tetrazene + NADP+ + H2O + ?
N-aminopyrrolidine + NADPH + H+ + O2
N-aminopyrrolidine N-oxide + NADP+ + H2O
-
-
-
-
r
N-aminopyrrolidone + NADPH + O2
?
N-deacetyl ketoconazole + NADPH + H+ + O2
?
an antifungal agent, is converted to the N-hydroxyl
-
-
?
N-deacetyl ketoconazole + NADPH + H+ + O2
N-deacetyl ketoconazole N-oxide + NADP+ + H2O
n-decylamine + NADPH + O2
1-nitrosodecane + NADP+ + H2O
N-methyl-1,2,3,4-tetrahydroisoquinoline + NADPH + O2
?
-
-
-
-
?
N-methyl-tamoxifen + NADPH + O2
N-methyl-tamoxifen N-oxide + NADP+ + H2O
-
recombinant isozymes FMO1 and FMO3
-
-
?
n-octylamine + NADPH + O2
1-nitrosooctane + NADP+ + H2O
n-propylhydrazine + NADPH + H+ + O2
N-propylhydrazine N-oxide + NADP+ + H2O
-
-
-
-
r
naphthylthiourea + NADPH + O2
naphthylthiourea S-oxide + NADP+ + H2O
nicotine + NADPH + H+ + O2
(S)-nicotine N1-oxide + NADP+ + H2O
-
substrate of isoform FMO3
-
-
?
nicotine + NADPH + H+ + O2
nicotine N-oxide + NADP+ + H2O
nomifensine + NADPH + H+ + O2
?
-
substrate of isoforms FMO3 and FMO5
-
-
?
NSC645809 + NADPH + H+ + O2
N,N-diethyl-2-((8-hydroxy-6-oxo-6H-imidazo[4,5,1-de]acridin-5-yl)amino)ethan-1-amine oxide + NADP+ + H2O
-
substrate of isoforms FMO1 and FMO3
-
-
?
olanzapine + NADPH + H+ + O2
1-methyl-4-(2-methyl-10H-benzo[b]thieno[2,3-e][1,4]diazepin-4-yl)piperazine 1-oxide + NADP+ + H2O
-
substrate of isoform FMO3
-
-
?
olopatadine + NADPH + H+ + O2
olopatadine N-oxide + NADP+ + H2O
orphenadrine + NADPH + H+ + O2
orphenadrine N-oxide + NADP+ + H2O
an anticholinergic drug
-
-
?
p-chloro-N-methylaniline + NADPH + O2
?
p-tolyl sulfide + NADPH + O2
p-tolyl sulfoxide + NADP+ + H2O
pargyline + NADPH + H+ + O2
pargyline N-oxide + NADP+ + H2O
-
substrate of isoforms FMO1 and FMO3
-
-
?
pargyline + NADPH + O2
?
-
inhibitor of monoaminoxidase B
-
-
?
pentoxifylline + NADPH + H+ + O2
pentoxifylline N-oxide + NADP+ + H2O
phenethylamine + NADPH + O2
phenethylamine N-oxide + NADP+ + H2O
-
isozyme FMO3
-
-
?
phenyl propyl sulfide + NADPH + H+ + O2
phenyl propyl sulfide S-oxide + NADP+ + H2O
-
sulfoxidation by recombinant PTDH-mFMO fusion protein
-
-
?
phenylhydrazine + NADPH + H+ + O2
phenylhydrazine N-oxide + NADP+ + H2O
-
-
-
-
r
phenylhydrazine + NADPH + O2
?
phenylthiourea + NADPH + O2
?
phenylthiourea + NADPH + O2
phenylthiourea S-oxide + NADP+ + H2O
phorate + NADPH + H+ + O2
?
a thioether-containing organophosphate insecticide
-
-
?
phospho-sulindac + NADPH + H+ + O2
?
-
substrate of isoforms FMO1, FMO3, and FMO5
-
-
?
primaquine + NADPH + H+ + O2
?
-
substrate of isoform FMO3
-
-
?
procarbazine + NADPH + H+ + O2
procarbazine N-oxide + NADP+ + H2O
-
-
-
-
r
procarbazine + NADPH + O2
?
propranolol + NADPH + O2
propranolol-hydroxylamine + NADP+
-
-
-
-
?
pyrazolacridine + NADPH + H+ + O2
pyrazolacridine N-oxide + NADP+ + H2O
pyrazoloacridine + NADPH + O2
pyrazoloacridine N-oxide + NADP+ + H2O
-
-
-
-
?
quazepam + NADPH + H+ + O2
7-chloro-5-(2-fluorophenyl)-1-(2,2,2-trifluoroethyl)-1,3-dihydro-2H-benzo[e][1,4]diazepin-2-one + NADP+ + H2O
-
substrate of isoform FMO1
-
-
?
R(-)-deprenyl + NADPH + O2
?
-
inhibitor of monoaminoxidase B
-
-
?
ranitidine + NADPH + H+ + O2
?
ranitidine + NADPH + O2
?
-
-
-
-
?
S-allyl-L-cysteine + NADPH + H+ + O2
?
-
-
-
?
S-allyl-L-cysteine + NADPH + H+ + O2
? + NADP+ + H2O
stereochemmistry, overview
-
-
?
S-benzyl-L-cysteine + NADPH + O2
S-benzyl-L-cysteine S-oxide + NADP+ + H2O
-
isozyme FMO1
-
-
?
S-farnesylcysteine + NADPH + O2
S-farnesylcysteine S-oxide + NADP+ + H2O
-
-
-
-
?
S-farnesylcysteine methyl ester + NADPH + O2
?
-
-
-
-
?
S-farnesylcysteine methyl ester + NADPH + O2
S-farnesylcysteine S-oxide methyl ester + NADP+ + H2O
-
-
-
-
?
S-methyl esonarimod + NADPH + H+ + O2
?
S-methyl esonarimod + NADPH + H+ + O2
S-methyl esonarimod S-oxide + NADP+ + H2O
S-methyl N,N-diethyldithiocarbamate + NADPH + H+ + O2
(diethylnitroryl)(methylsulfanyl)methanethione + NADP+ + H2O
-
substrate of isoform FMO1 and FMO3
-
-
?
S16020 + NADPH + H+ + O2
S16020 N-oxide + NADP+ + H2O
a topoisomerase II inhibitor and antitumor drug, is converted to the N-oxide
-
-
?
secondary amine + NADPH + O2
secondary nitrone + NADP+ + H2O
-
-
first oxidation to the N-hydroxy amine and then to the corresponding nitrone
?
selegiline + NADPH + H+ + O2
?
-
i.e. (2R)-N-methyl-1-phenyl-N-prop-2-ynylpropan-2-amine
-
-
?
selegiline + NADPH + O2
selegiline N-oxide + NADP+
-
-
-
-
?
seleno-L-methionine + NADPH + H+ + O2
seleno-L-methionine Se-oxide + NADP+ + H2O
-
-
-
?
selenomethionine + NADPH + H+ + O2
seleno-L-methionine Se-oxide + NADP+ + H2O
-
substrate of isoform FMO3
-
-
?
SNI-2011 + NADPH + H+ + O2
?
a muscarinic receptor antagonist, is converted to the N-oxide
-
-
?
SNI-2011 + NADPH + H+ + O2
SNI-2011 N-oxide + NADP+ + H2O
-
substrate of isoform FMO1
-
-
?
sulfamethoxazole + NADPH + O2
?
sulindac sulfide + NADPH + H+ + O2
?
-
substrate of isoforms FMO1 and FMO3
-
-
?
sulindac sulfide + NADPH + H+ + O2
sulindac + NADP+ + H2O
sulindac sulfide + NADPH + H+ + O2
sulindac sulfide S-oxide + NADP+ + H2O
-
-
-
?
sulindac sulfide + NADPH + O2
(S,R)-sulindac + NADP+ + H2O
-
-
-
-
?
sulindac sulfide + NADPH + O2
sulindac + NADP+ + H2O
-
-
-
-
?
tamoxifen + NADPH + H+ + O2
?
tamoxifen + NADPH + H+ + O2
tamoxifen N-oxide + NADP+ + H2O
tamoxifen + NADPH + O2
?
-
-
-
-
?
tamoxifen + NADPH + O2
tamoxifen N-oxide + NADP+ + H2O
tazarotenic acid + NADPH + H+ + O2
?
a retinoic acid receptor modulator, is converted to the S-oxide
-
-
?
tazarotenic acid + NADPH + H+ + O2
tazarotenate N-oxide + NADP+ + H2O
tertiary amine + NADPH + O2
tertiary N-oxide + NADP+ + H2O
-
-
-
-
?
TG100435 + NADPH + H+ + O2
1-(2-(4-((7-(2,6-dichlorophenyl)-5-methylbenzo[e][1,2,4]triazin-3-yl)amino)phenoxy)ethyl)pyrrolidine 1-oxide + NADP+ + H2O
-
substrate of isoform FMO3
-
-
?
TG100435 + NADPH + H+ + O2
?
-
substrate of isoform FMO1
-
-
?
thiacetazone + 2 NADPH + 2 H+ + 2 O2
thiacetazone carbodiimide + 2 NADP+ + 2 H2O
thiacetazone + 2 NADPH + 2 O2
(E)-{(2E)-[4-(acetylamino)benzylidene]hydrazinylidene}(amino)methanesulfinic acid + 2 NADP+ + H2O
-
bioactivation by EtaA
-
-
?
thiacetazone + NADPH + H+ + O2
?
thiacetazone + NADPH + H+ + O2
thiacetazone N-oxide + NADP+ + H2O
thiacetazone + NADPH + H+ + O2
thiacetazone S-oxide + NADP+ + H2O
thioacetamide + NADPH + O2
?
thiobenzamide + NADPH + H+ + O2
thiobenzamide N-oxide + NADP+ + H2O
-
N-oxidation
-
-
?
thiobenzamide + NADPH + O2
?
thiocarbanilide + NADPH + O2
?
-
-
-
-
?
thiourea + NADPH + H+ + O2
?
thiourea + NADPH + O2
thiourea S-oxide + NADP+ + H2O
tigecycline + NADPH + O2
11a-hydroxytigecycline + NADP+ + H2O
tozasertib + NADPH + H+ + O2
?
tozasertib + NADPH + H+ + O2
tozasertib N-oxide + NADP+ + H2O
-
-
-
?
triethylamine + NADPH + H+ + O2
triethylamine N-oxide + NADP+ + H2O
-
-
-
-
?
trifluoperazine + NADPH + O2
?
-
-
-
-
?
trifluoroperazine + NADPH + H+ + O2
2,3,4-trifluoropyridine 1-oxide + NADP+ + H2O
-
substrate of isoform FMO3
-
-
?
trifluoroperazine + NADPH + O2
?
-
-
-
-
?
trimethylamine + NADPH + H+ + O2
?
trimethylamine + NADPH + H+ + O2
trimethylamine N-oxide + NADP+ + H2O
trimethylamine + NADPH + O2
?
trimethylamine + NADPH + O2
trimethylamine N-oxide + NADP+ + H2O
tyramine + NADPH + O2
tyramine N-oxide + NADP+ + H2O
-
-
-
-
?
voriconazole + NADPH + H+ + O2
?
xanomeline + NADPH + H+ + O2
xanomeline N-oxide + NADP+ + H2O
[7-(2,6-dichloro-phenyl)-5-methyl-benzo[1,2,4]triazin-3-yl]-[4-(2-pyrrolidin-1-yl-ethoxy)-phenyl]-amine + NADPH + H+ + O2
[7-(2,6-dichlorophenyl)-5-methyl-benzo[1,2,4]triazin-3-yl]-(4-[2-(1-oxy-pyrrolidin-1-yl)-ethoxy]-phenyl)-amine + NADP+ + H2O
-
i.e. TG100435, a multitargeted Src family kinase inhibitor with anticancer activity, FMO3 is the primary enzyme responsible for TG100855 formation, enzyme-mediated retroreduction of TG100855 back to TG100435 is observed catalyzed by a cytochrome P450 reductase, overview
i.e. TG100855, the N-oxide product is also a multitargeted Src family kinase inhibitor with anticancer activity
-
?
additional information
?
-
1,1-dimethylhydrazine + NADPH + O2
formaldehyde + CH3N2H3 + NADP+
-
-
-
?
1,1-dimethylhydrazine + NADPH + O2
formaldehyde + CH3N2H3 + NADP+
-
possibly, and other 1,1-disubstituted hydrazines
-
?
1,1-dimethylhydrazine + NADPH + O2
formaldehyde + CH3N2H3 + NADP+
-
-
-
?
1,1-dimethylhydrazine + NADPH + O2
formaldehyde + CH3N2H3 + NADP+
-
possibly, and other 1,1-disubstituted hydrazines
-
?
1,1-dimethylhydrazine + NADPH + O2
formaldehyde + CH3N2H3 + NADP+
-
-
-
?
1,1-dimethylhydrazine + NADPH + O2
formaldehyde + CH3N2H3 + NADP+
-
possibly, and other 1,1-disubstituted hydrazines
-
?
1,2,3,4-tetrahydroisoquinoline + NADPH + O2
?
-
-
-
-
?
1,2,3,4-tetrahydroisoquinoline + NADPH + O2
?
-
-
-
-
?
1,2-dimethylhydrazine + NADPH + O2
?
-
-
-
-
?
1,2-dimethylhydrazine + NADPH + O2
?
-
-
-
-
?
1,2-dimethylphenylhydrazine + NADPH + O2
?
-
-
-
-
?
1,2-dimethylphenylhydrazine + NADPH + O2
?
-
-
-
-
?
1-butanethiol + NADPH + O2
?
-
-
-
-
?
1-butanethiol + NADPH + O2
?
-
-
-
-
?
1-butanethiol + NADPH + O2
?
-
-
-
-
?
1-butanethiol + NADPH + O2
?
-
-
-
-
?
1-methyl-1-phenylhydrazine + NADPH + O2
?
-
-
-
-
?
1-methyl-1-phenylhydrazine + NADPH + O2
?
-
-
-
-
?
1-methyl-1-phenylhydrazine + NADPH + O2
?
-
-
-
-
?
1-methyl-2-benzylhydrazine + NADPH + O2
?
-
-
-
-
?
1-methyl-2-benzylhydrazine + NADPH + O2
?
-
-
-
-
?
1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine + NADPH + H+ + O2
1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine N-oxide + NADP+ + H2O
-
-
-
-
?
1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine + NADPH + H+ + O2
1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine N-oxide + NADP+ + H2O
-
-
-
?
1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine + NADPH + H+ + O2
1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine N-oxide + NADP+ + H2O
-
reaction in microsomal detoxification pathway of 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine, a neurotoxin to nigrostriatal dopaminergic neurons
-
-
?
1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine + NADPH + H+ + O2
1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine N-oxide + NADP+ + H2O
-
-
-
?
1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine + NADPH + H+ + O2
1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine N-oxide + NADP+ + H2O
-
reaction in microsomal detoxification pathway of 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine, a neurotoxin to nigrostriatal dopaminergic neurons
-
-
?
1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine + NADPH + H+ + O2
1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine N-oxide + NADP+ + H2O
-
-
-
-
?
1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine + NADPH + H+ + O2
1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine N-oxide + NADP+ + H2O
-
one of the predominant enzmyes responsible for the oxygenation of 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine
-
-
?
1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine + NADPH + O2
?
-
-
-
-
?
1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine + NADPH + O2
?
-
-
-
-
?
1-[4-(methylsulfanyl)phenyl]ethanone + NADPH + H+ + O2
(R,S)-1-[4-(methylsulfanyl)phenyl]ethanone S-oxide + NADP+ + H2O
-
sulfoxidation of the thioanisole derivative by recombinant PTDH-mFMO fusion protein. Enantiomeric reaction with 21% R-enantiomer as product
-
-
?
1-[4-(methylsulfanyl)phenyl]ethanone + NADPH + H+ + O2
(R,S)-1-[4-(methylsulfanyl)phenyl]ethanone S-oxide + NADP+ + H2O
-
sulfoxidation of the thioanisole derivative by recombinant PTDH-mFMO fusion protein. Enantiomeric reaction with 21% R-enantiomer as product
-
-
?
10-(N,N-dimethylaminoalkyl)-2-(trifluoromethyl) phenothiazines + NADPH + O2
?
-
with the alkyl side chain varying in length from 5 to 7 carbons, no activity with shorter side chains by isozyme FMO2
-
-
?
10-(N,N-dimethylaminoalkyl)-2-(trifluoromethyl) phenothiazines + NADPH + O2
?
-
with the alkyl side chain varying in length from 2 to 7 carbons, liver isozyme FMO1
-
-
?
10-(N,N-dimethylaminooctyl)2-(trifluoromethyl)phenothiazene + NADPH + H+ + O2
? + NADP+ + H2O
-
-
-
?
10-(N,N-dimethylaminooctyl)2-(trifluoromethyl)phenothiazene + NADPH + H+ + O2
? + NADP+ + H2O
-
-
-
?
10-(N,N-dimethylaminopentyl)-2-(trifluoromethyl)phenothiazine + NADPH + O2
?
-
-
-
-
?
10-(N,N-dimethylaminopentyl)-2-(trifluoromethyl)phenothiazine + NADPH + O2
?
-
isozyme FMO3
-
-
?
10-N-(n-octylamino)-2-(trifluoromethyl) phenothiazine + NADPH + O2
10-N-(n-octylamino)-2-(trifluoromethyl) phenothiazine N-oxide + NADP+ + H2O
-
-
-
-
?
10-N-(n-octylamino)-2-(trifluoromethyl) phenothiazine + NADPH + O2
10-N-(n-octylamino)-2-(trifluoromethyl) phenothiazine N-oxide + NADP+ + H2O
-
formation of the cis-oxime
-
-
?
2,4,5-trichlorphenol + O2
2,5-dichlorohydroquinone + H2O + Cl-
-
100% conversion
-
-
?
2,4,5-trichlorphenol + O2
2,5-dichlorohydroquinone + H2O + Cl-
-
100% conversion
-
-
?
2,4,6-trichlorphenol + O2
2,6-dichlorohydroquinone + H2O + Cl-
-
72% conversion
-
-
?
2,4,6-trichlorphenol + O2
2,6-dichlorohydroquinone + H2O + Cl-
-
72% conversion
-
-
?
2,4-dichlorphenol + O2
chlorohydroquinone + H2O + Cl-
-
100% conversion
-
-
?
2,4-dichlorphenol + O2
chlorohydroquinone + H2O + Cl-
-
100% conversion
-
-
?
2-(methylsulfanyl)pyridine + NADPH + H+ + O2
2-(methylsulfanyl)pyridine S-oxide + NADP+ + H2O
-
sulfoxidation by recombinant PTDH-mFMO fusion protein
-
-
?
2-(methylsulfanyl)pyridine + NADPH + H+ + O2
2-(methylsulfanyl)pyridine S-oxide + NADP+ + H2O
-
sulfoxidation by recombinant PTDH-mFMO fusion protein
-
-
?
2-(methylsulfanyl)thiophene + NADPH + H+ + O2
2-(methylsulfanyl)thiophene S-oxide + NADP+ + H2O
-
sulfoxidation by recombinant PTDH-mFMO fusion protein
-
-
?
2-(methylsulfanyl)thiophene + NADPH + H+ + O2
2-(methylsulfanyl)thiophene S-oxide + NADP+ + H2O
-
sulfoxidation by recombinant PTDH-mFMO fusion protein
-
-
?
2-chlorophenol + O2
chlorohydroquinone + H2O
-
-
-
-
?
2-chlorophenol + O2
chlorohydroquinone + H2O
-
-
-
-
?
2-chlorophenyl methyl sulfide + NADPH + H+ + O2
(R,S)-2-chlorophenyl methyl sulfide S-oxide + NADP+ + H2O
-
sulfoxidation of the thioanisole derivative by recombinant PTDH-mFMO fusion protein. Enantiomeric reaction with 75% R-enantiomer as product
-
-
?
2-chlorophenyl methyl sulfide + NADPH + H+ + O2
(R,S)-2-chlorophenyl methyl sulfide S-oxide + NADP+ + H2O
-
sulfoxidation of the thioanisole derivative by recombinant PTDH-mFMO fusion protein. Enantiomeric reaction with 75% R-enantiomer as product
-
-
?
2-mercaptobenzimidazole + NADPH + O2
?
-
-
-
-
?
2-mercaptobenzimidazole + NADPH + O2
?
-
-
-
-
?
2-mercaptobenzimidazole + NADPH + O2
?
-
-
-
-
?
2-mercaptobenzimidazole + NADPH + O2
?
-
-
-
-
?
4-chlorophenol + O2
hydroquinone + H2O + Cl-
-
100% conversion
-
-
?
4-chlorophenol + O2
hydroquinone + H2O + Cl-
-
100% conversion
-
-
?
5-[[3-(dimethylamino)propyl]amino]-8-hydroxy-6H-[1,2,3]triazolo[4,5,1-de]acridin-6-one + NADPH + H+ + O2
5-[[3-(dimethylnitroryl)propyl]amino]-8-hydroxy-6H-[1,2,3]triazolo[4,5,1-de]acridin-6-one + NADP+ + H2O
i.e. C-1305
-
-
?
5-[[3-(dimethylamino)propyl]amino]-8-hydroxy-6H-[1,2,3]triazolo[4,5,1-de]acridin-6-one + NADPH + H+ + O2
5-[[3-(dimethylnitroryl)propyl]amino]-8-hydroxy-6H-[1,2,3]triazolo[4,5,1-de]acridin-6-one + NADP+ + H2O
-
i.e. C-1305
-
-
?
5-[[3-(dimethylamino)propyl]amino]-8-methoxy-6H-[1,2,3]triazolo[4,5,1-de]acridin-6-one + NADPH + H+ + O2
5-[[3-(dimethylnitroryl)propyl]amino]-8-methoxy-6H-[1,2,3]triazolo[4,5,1-de]acridin-6-one + NADP+ + H2O
i.e. C-1299
-
-
?
5-[[3-(dimethylamino)propyl]amino]-8-methoxy-6H-[1,2,3]triazolo[4,5,1-de]acridin-6-one + NADPH + H+ + O2
5-[[3-(dimethylnitroryl)propyl]amino]-8-methoxy-6H-[1,2,3]triazolo[4,5,1-de]acridin-6-one + NADP+ + H2O
i.e. C-1305
-
-
?
5-[[3-(dimethylamino)propyl]amino]-8-methoxy-6H-[1,2,3]triazolo[4,5,1-de]acridin-6-one + NADPH + H+ + O2
5-[[3-(dimethylnitroryl)propyl]amino]-8-methoxy-6H-[1,2,3]triazolo[4,5,1-de]acridin-6-one + NADP+ + H2O
-
i.e. C-1299
-
-
?
alpha-naphthylthiourea + NADPH + O2
?
-
-
-
-
?
alpha-naphthylthiourea + NADPH + O2
?
-
-
-
-
?
alpha-naphthylthiourea + NADPH + O2
?
-
-
-
-
?
alpha-naphthylthiourea + NADPH + O2
?
-
-
-
-
?
aminopyrine + NADPH + O2
?
-
-
-
-
?
aminopyrine + NADPH + O2
?
-
-
-
-
?
aminopyrine + NADPH + O2
?
-
-
-
-
?
aminopyrine + NADPH + O2
?
-
-
-
-
?
amphetamine + NADPH + H+ + O2
?
an antipsychotic agent, is converted to the hydroxylamine
-
-
?
amphetamine + NADPH + H+ + O2
?
an antipsychotic agent, is converted to the hydroxylamine
-
-
?
benzydamine + NADPH + H+ + O2
benzydamine N-oxide + NADP+ + H2O
-
-
-
-
?
benzydamine + NADPH + H+ + O2
benzydamine N-oxide + NADP+ + H2O
-
-
-
-
?
benzydamine + NADPH + H+ + O2
benzydamine N-oxide + NADP+ + H2O
-
-
-
-
?
benzydamine + NADPH + H+ + O2
benzydamine N-oxide + NADP+ + H2O
-
N-oxidation
-
-
?
benzydamine + NADPH + H+ + O2
benzydamine N-oxide + NADP+ + H2O
-
-
-
-
?
benzydamine + NADPH + H+ + O2
benzydamine N-oxide + NADP+ + H2O
-
-
-
?
benzydamine + NADPH + H+ + O2
benzydamine N-oxide + NADP+ + H2O
-
-
-
-
?
benzydamine + NADPH + H+ + O2
benzydamine N-oxide + NADP+ + H2O
high activity
-
-
?
benzydamine + NADPH + H+ + O2
benzydamine N-oxide + NADP+ + H2O
a nonsteroidal antiinflammatory drug, is converted to the N-oxide
-
-
?
benzydamine + NADPH + H+ + O2
benzydamine N-oxide + NADP+ + H2O
-
N-oxidation
-
-
?
benzydamine + NADPH + H+ + O2
benzydamine N-oxide + NADP+ + H2O
-
substrate of isoforms FMO1 and FMO3
-
-
?
benzydamine + NADPH + H+ + O2
benzydamine N-oxide + NADP+ + H2O
N-oxygenation of benzydamine by the wild-type and N61S mutant variant of FMO3
-
-
?
benzydamine + NADPH + H+ + O2
benzydamine N-oxide + NADP+ + H2O
-
-
-
-
?
benzydamine + NADPH + H+ + O2
benzydamine N-oxide + NADP+ + H2O
-
substrate of isoforms FMO1 and FMO3
-
-
?
benzydamine + NADPH + H+ + O2
benzydamine N-oxide + NADP+ + H2O
-
-
-
-
?
benzydamine + NADPH + H+ + O2
benzydamine N-oxide + NADP+ + H2O
-
-
-
-
?
benzydamine + NADPH + H+ + O2
benzydamine N-oxide + NADP+ + H2O
-
-
-
-
?
benzydamine + NADPH + O2
benzydamine N-oxide + NADP+ + H2O
KC734478, KC734481, KC734482, KC734486
-
-
-
?
benzydamine + NADPH + O2
benzydamine N-oxide + NADP+ + H2O
KC734478, KC734481, KC734482, KC734486
highest activity of all isoforms tested
-
-
?
benzydamine + NADPH + O2
benzydamine N-oxide + NADP+ + H2O
-
-
-
-
?
benzylhydrazine + NADPH + O2
?
-
-
-
-
?
benzylhydrazine + NADPH + O2
?
-
-
-
-
?
beta-ethylphenylhydrazine + NADPH + O2
?
-
-
-
-
?
beta-ethylphenylhydrazine + NADPH + O2
?
-
-
-
-
?
butylhydrazine + NADPH + O2
?
-
-
-
-
?
butylhydrazine + NADPH + O2
?
-
-
-
-
?
chlorpromazine + NADPH + H+ + O2
chlorpromazine N-oxide + NADP+ + H2O
-
-
-
?
chlorpromazine + NADPH + H+ + O2
chlorpromazine N-oxide + NADP+ + H2O
a dopemaine D2 antagonist
-
-
?
chlorpromazine + NADPH + H+ + O2
chlorpromazine N-oxide + NADP+ + H2O
a dopemaine D2 antagonist
-
-
?
chlorpromazine + NADPH + O2
?
-
-
-
-
?
chlorpromazine + NADPH + O2
?
-
liver microsomes
-
-
?
chlorpromazine + NADPH + O2
?
-
liver isozyme FMO1
-
-
?
cimetidine + NADPH + H+ + O2
cimetidine S-oxide + NADP+ + H2O
-
S-oxygenation of cimetidine, i.e. CIM, a histamine H2-receptor antagonist of therapeutic utility in the treatment of peptic ulcer disease and gastric hypersecretory syndromes. Development of in-line screening and an off-line chiral CE method for determination of the stereoselectivity of flavin-containing monooxygenase isoforms FMO1, FMO3, and FMO5 using chiral specific selectors, overview
-
-
?
cimetidine + NADPH + H+ + O2
cimetidine S-oxide + NADP+ + H2O
-
substrate of isoforms FMO1 and FMO3
-
-
?
clomiphene + NADPH + H+ + O2
clomiphene N-oxide + NADP+ + H2O
-
-
-
?
clomiphene + NADPH + H+ + O2
clomiphene N-oxide + NADP+ + H2O
clomiphene is used in infertility medication
-
-
?
clozapine + NADPH + H+ + O2
clozapine N-oxide + NADP+ + H2O
-
N-oxidation
-
-
?
clozapine + NADPH + H+ + O2
clozapine N-oxide + NADP+ + H2O
-
-
-
?
clozapine + NADPH + H+ + O2
clozapine N-oxide + NADP+ + H2O
an antipsychotic agent, is converted to the N-oxide
-
-
?
clozapine + NADPH + H+ + O2
clozapine N-oxide + NADP+ + H2O
an antipsychotic agent, is converted to the N-oxide
-
-
?
clozapine + NADPH + H+ + O2
clozapine N-oxide + NADP+ + H2O
-
N-oxidation
-
-
?
clozapine + NADPH + H+ + O2
clozapine N-oxide + NADP+ + H2O
-
substrate of isoform FMO3
-
-
?
cysteamine + NADPH + H+ + O2
?
-
-
-
-
?
cysteamine + NADPH + H+ + O2
?
-
-
-
-
?
cysteamine + NADPH + H+ + O2
?
-
-
-
-
?
cysteamine + NADPH + O2
?
-
-
-
-
?
cysteamine + NADPH + O2
?
-
-
-
-
?
cysteamine + NADPH + O2
?
-
-
-
-
?
cysteamine + NADPH + O2
?
-
-
-
-
?
cysteamine + NADPH + O2
?
-
-
-
-
?
cysteamine + NADPH + O2
cysteamine N-oxide + NADP+ + H2O
-
-
-
-
?
cysteamine + NADPH + O2
cysteamine N-oxide + NADP+ + H2O
-
-
-
-
?
cysteamine + NADPH + O2
cysteamine N-oxide + NADP+ + H2O
-
-
-
-
?
cysteamine + NADPH + O2
cysteamine N-oxide + NADP+ + H2O
-
-
-
-
?
dapsone + NADPH + O2
?
bioactivation by isozyme FMO3, not FMO1, results in covalent adduct formation
-
-
?
dapsone + NADPH + O2
?
isozyme FMO3, not FMO1
-
-
?
demeton-O + NADPH + O2
demeton-O sulfoxide + NADP+ + H2O
-
-
-
-
?
demeton-O + NADPH + O2
demeton-O sulfoxide + NADP+ + H2O
-
i.e. O,O-diethyl O-2-ethylthioethyl phosphorothioate, isozymes FMO1 and FMO3, higher activity by FMO1
-
-
?
deprenyl + NADPH + H+ + O2
?
a monoamine oxidase type B inhibitor, is converted to the hydroxylamine
-
-
?
deprenyl + NADPH + H+ + O2
?
a monoamine oxidase type B inhibitor, is converted to the hydroxylamine
-
-
?
deprenyl + NADPH + H+ + O2
?
-
-
-
-
?
dibenzylamine + NADPH + O2
?
-
-
-
-
?
dibenzylamine + NADPH + O2
?
-
-
-
-
?
dibenzylamine + NADPH + O2
?
-
-
-
-
?
dibenzylamine + NADPH + O2
?
-
-
-
-
?
dimethylsulfone + NADH + H+ + O2
methanesulfinate + NAD+ + H2O
-
-
-
-
?
dimethylsulfone + NADH + H+ + O2
methanesulfinate + NAD+ + H2O
-
-
-
-
?
disulfoton + NADPH + H+ + O2
?
-
-
-
-
?
disulfoton + NADPH + H+ + O2
?
a thioether-containing organophosphate insecticide
-
-
?
ephedrine + NADPH + O2
?
-
-
-
-
?
ephedrine + NADPH + O2
?
-
-
-
-
?
ephedrine + NADPH + O2
?
-
-
-
-
?
ephedrine + NADPH + O2
?
-
-
-
-
?
ethiofencarb + NADPH + O2
ethiofencarb sulfoxide + NADP+ + H2O
-
-
-
-
?
ethiofencarb + NADPH + O2
ethiofencarb sulfoxide + NADP+ + H2O
-
i.e. alpha-ethylthio-o-tolyl methylcarbamate, isozymes FMO1 and FMO3, higher activity by FMO1
-
-
?
ethionamide + NADPH + H+ + O2
?
an antibiotic agent
-
-
?
ethionamide + NADPH + H+ + O2
?
an antibiotic agent
-
-
?
ethionamide + NADPH + H+ + O2
ethionamide N-oxide + NADP+ + H2O
an antibiotic agent
-
-
?
ethionamide + NADPH + H+ + O2
ethionamide N-oxide + NADP+ + H2O
-
-
-
?
ethionamide + NADPH + H+ + O2
ethionamide S-oxide + NADP+ + H2O
-
-
-
?
ethionamide + NADPH + H+ + O2
ethionamide S-oxide + NADP+ + H2O
ethionamide is a pro-drug requiring bioactivation to exert toxicity
-
-
?
ethionamide + NADPH + H+ + O2
ethionamide S-oxide + NADP+ + H2O
i.e. ETA, S-oxygenation by isozymes FMO1, FMO2, and FMO3
-
-
?
ethionamide + NADPH + H+ + O2
ethionamide S-oxide + NADP+ + H2O
-
substrate of isoforms FMO1, FMO2, and FMO3
-
-
?
ethionamide + NADPH + H+ + O2
ethionamide S-oxide + NADP+ + H2O
-
-
-
?
ethionamide + NADPH + H+ + O2
ethionamide S-oxide + NADP+ + H2O
ethionamide is a pro-drug requiring bioactivation to exert toxicity
-
-
?
ethionamide + NADPH + H+ + O2
ethionamide S-oxide + NADP+ + H2O
i.e. ETA, S-oxygenation by isozymes FMO1, FMO2, and FMO3
-
-
?
ethionamide + NADPH + O2 + H+
2-ethyl-N-hydroxypyridine-4-carbothioamide + NADP+ + H2O
-
bioactivation by isozymes FMO1 and FMO3
-
-
?
ethionamide + NADPH + O2 + H+
2-ethyl-N-hydroxypyridine-4-carbothioamide + NADP+ + H2O
-
a thioamide-containing second line antitubercular prodrug
-
-
?
ethionamide + NADPH + O2 + H+
2-ethyl-N-hydroxypyridine-4-carbothioamide + NADP+ + H2O
-
bioactivation by EtaA
-
-
?
ethionamide + NADPH + O2 + H+
2-ethyl-N-hydroxypyridine-4-carbothioamide + NADP+ + H2O
-
a thioamide-containing second line antitubercular prodrug
-
-
?
ethylene sulfide + NADPH + O2
?
-
-
-
-
?
ethylene sulfide + NADPH + O2
?
-
-
-
-
?
ethylene sulfide + NADPH + O2
?
-
-
-
-
?
ethylene sulfide + NADPH + O2
?
-
-
-
-
?
fenthion + NADPH + O2
fenthion sulfoxide + NADP+ + H2O
-
-
-
-
?
fenthion + NADPH + O2
fenthion sulfoxide + NADP+ + H2O
-
-
more than 95% (+)-sulfoxide
-
?
fenthion + NADPH + O2
fenthion sulfoxide + NADP+ + H2O
-
i.e. O,O-dimethyl O-4-methylthio-m-tolyl phosphorothioate, isozymes FMO1 and FMO3, stereospecifc product formation, overview
-
-
?
GSK5182 + NADPH + H+ + O2
GSK5182 N-oxide + NADP+ + H2O
-
-
-
?
GSK5182 + NADPH + H+ + O2
GSK5182 N-oxide + NADP+ + H2O
an antidiabetic lead molecule
-
-
?
hypotaurine + H2O + NAD+
taurine + NADH
-
-
-
?
hypotaurine + H2O + NAD+
taurine + NADH
-
metabolism of cysteine
-
?
hypotaurine + NADH + H+ + O2
taurine + NAD+ + H2O
S-oxygenation
-
-
?
hypotaurine + NADH + H+ + O2
taurine + NAD+ + H2O
S-oxygenation
-
-
?
hypotaurine + NADPH + H+ + O2
taurine + NADP+ + H2O
S-oxygenation
-
-
?
hypotaurine + NADPH + H+ + O2
taurine + NADP+ + H2O
S-oxygenation
-
-
?
imipramine + NADPH + H+ + O2
imipramine N-oxide + NADP+ + H2O
an antidepressant, is converted to the N-oxide
-
-
?
imipramine + NADPH + H+ + O2
imipramine N-oxide + NADP+ + H2O
an antidepressant, is converted to the N-oxide
-
-
?
imipramine + NADPH + H+ + O2
imipramine N-oxide + NADP+ + H2O
-
substrate of isoform FMO1
-
-
?
imipramine + NADPH + H+ + O2
imipramine N-oxide + NADP+ + H2O
-
substrate of isoform FMO1
-
-
?
imipramine + NADPH + O2
?
-
-
-
-
?
imipramine + NADPH + O2
?
-
-
-
-
?
imipramine + NADPH + O2
?
-
-
-
-
?
imipramine + NADPH + O2
?
-
liver microsomes
-
-
?
imipramine + NADPH + O2
?
-
-
-
-
?
imipramine + NADPH + O2
?
-
-
-
-
?
imipramine + NADPH + O2
?
-
liver isozyme FMO1
-
-
?
imipramine + NADPH + O2
imipramine N-oxide + NADP+ + H2O
-
-
-
-
?
imipramine + NADPH + O2
imipramine N-oxide + NADP+ + H2O
-
-
-
-
?
indole + NADPH + H+ + O2
indole N-oxide + NADP+ + H2O
-
-
-
-
?
indole + NADPH + H+ + O2
indole N-oxide + NADP+ + H2O
-
-
-
-
?
indole + NADPH + H+ + O2
indoxyl + NADP+ + H2O
-
-
-
-
?
indole + NADPH + H+ + O2
indoxyl + NADP+ + H2O
-
-
-
-
?
indole + NADPH + H+ + O2
indoxyl + NADP+ + H2O
-
-
-
-
?
indole + NADPH + H+ + O2
indoxyl + NADP+ + H2O
-
-
-
?
indole + NADPH + H+ + O2
indoxyl + NADP+ + H2O
-
-
-
-
?
indole + NADPH + H+ + O2
indoxyl + NADP+ + H2O
-
-
-
?
isopropylhydrazine + NADPH + O2
?
-
-
-
-
?
isopropylhydrazine + NADPH + O2
?
-
-
-
-
?
itopride + NADPH + H+ + O2
itopride N-oxide + NADP+ + H2O
-
-
-
?
itopride + NADPH + H+ + O2
itopride N-oxide + NADP+ + H2O
-
-
-
-
?
itopride + NADPH + H+ + O2
itopride N-oxide + NADP+ + H2O
a dopamine D2 receptor antagonist, is converted to the N-oxide
-
-
?
itopride + NADPH + H+ + O2
itopride N-oxide + NADP+ + H2O
a dopamine D2 receptor antagonist, is converted to the N-oxide
-
-
?
itopride + NADPH + H+ + O2
itopride N-oxide + NADP+ + H2O
-
substrate of isoforms FMO1 and FMO3
-
-
?
K11777 + NADPH + H+ + O2
K11777 N-oxide + NADP+ + H2O
a cysteine protease inhibitor against Trypanosoma cruzi, is converted to the N-oxide
-
-
?
K11777 + NADPH + H+ + O2
K11777 N-oxide + NADP+ + H2O
-
substrate of isoform FMO3
-
-
?
L-Met-Phe + NADPH + O2
(L-Met-S-oxide)-Phe + NADP+ + H2O
-
isozymes FMO1-FMO4
-
-
?
L-Met-Phe + NADPH + O2
(L-Met-S-oxide)-Phe + NADP+ + H2O
-
liver microsomes
-
-
?
L-Met-Val + NADPH + O2
(L-Met-S-oxide)-Val + NADP+ + H2O
-
isozymes FMO1-FMO4, low activity by isozyme FMO1
-
-
?
L-Met-Val + NADPH + O2
(L-Met-S-oxide)-Val + NADP+ + H2O
-
liver microsomes
-
-
?
L-methionine + NADPH + O2
L-methionine S-oxide + NADP+ + H2O
-
-
-
-
?
L-methionine + NADPH + O2
L-methionine S-oxide + NADP+ + H2O
-
free and N-terminally peptide-bound L-methionine, no activity with modified peptide-bound methionine and with N-acetyl-L-methionine, isozymes FMO1-FMO4
stereospecificity for formation of the D-isomer, especially by isozyme FMO3
-
?
L-methionine + NADPH + O2
L-methionine S-oxide + NADP+ + H2O
-
-
-
-
?
L-methionine + NADPH + O2
L-methionine S-oxide + NADP+ + H2O
-
free and N-terminally peptide-bound L-methionine, no activity with modified peptide-bound methionine and with N-acetyl-L-methionine, isozymes FMO1-FMO4
stereospecificity for formation of the D-isomer, especially by isozyme FMO3
-
?
L-methionine + NADPH + O2
L-methionine S-oxide + NADP+ + H2O
-
-
-
-
?
L-methionine + NADPH + O2
L-methionine S-oxide + NADP+ + H2O
-
free and N-terminally peptide-bound L-methionine, no activity with modified peptide-bound methionine and with N-acetyl-L-methionine, isozymes FMO1-FMO4
stereospecificity for formation of the D-isomer, especially by isozyme FMO3
-
?
L-methionine + NADPH + O2
L-methionine S-oxide + NADP+ + H2O
-
-
-
-
?
L-seleno-methionine + NADPH + O2
L-methionine seleno-oxide + NADP+ + H2O
-
liver microsomes
-
-
?
L-seleno-methionine + NADPH + O2
L-methionine seleno-oxide + NADP+ + H2O
-
purified liver isozymes FMO1 and FMO3
-
-
?
lipoic acid + NADPH + O2
?
-
-
-
-
?
lipoic acid + NADPH + O2
?
-
-
-
-
?
methamphetamine + NADPH + H+ + O2
?
a psychostimulant, is converted to the hydroxylamine
-
-
?
methamphetamine + NADPH + H+ + O2
?
a psychostimulant, is converted to the hydroxylamine
-
-
?
methamphetamine + NADPH + O2
?
-
-
-
-
?
methamphetamine + NADPH + O2
?
-
-
-
-
?
methamphetamine + NADPH + O2
?
-
-
-
-
?
methamphetamine + NADPH + O2
?
-
-
-
-
?
methamphetamine + NADPH + O2
?
-
-
-
-
?
methimazole + NADPH + H+ + O2
?
a thyroperoxidase inhibitor
-
-
?
methimazole + NADPH + H+ + O2
?
a thyroperoxidase inhibitor, is converted to the S-oxide
-
-
?
methimazole + NADPH + H+ + O2
?
an thyroperoxidase inhibitor, is converted to the S-oxide
-
-
?
methimazole + NADPH + H+ + O2
?
-
-
-
-
?
methimazole + NADPH + H+ + O2
?
-
-
-
-
?
methimazole + NADPH + H+ + O2
?
-
FMO1, FMO2, and FMO3
-
-
?
methimazole + NADPH + H+ + O2
methimazole N-oxide + NADP+ + H2O
an thyroperoxidase inhibitor, is converted to the S-oxide
-
-
?
methimazole + NADPH + H+ + O2
methimazole N-oxide + NADP+ + H2O
-
N-oxidation
-
-
?
methimazole + NADPH + H+ + O2
methimazole N-oxide + NADP+ + H2O
KC734478, KC734481, KC734482, KC734486
-
-
-
?
methimazole + NADPH + H+ + O2
methimazole N-oxide + NADP+ + H2O
KC734478, KC734481, KC734482, KC734486
about 25% of the activityy with substrate benzydamine
-
-
?
methimazole + NADPH + H+ + O2
methimazole N-oxide + NADP+ + H2O
-
-
-
-
?
methimazole + NADPH + H+ + O2
methimazole N-oxide + NADP+ + H2O
-
-
-
-
?
methimazole + NADPH + H+ + O2
methimazole S-oxide + NADP+ + H2O
-
-
-
-
?
methimazole + NADPH + H+ + O2
methimazole S-oxide + NADP+ + H2O
-
-
-
-
?
methimazole + NADPH + H+ + O2
methimazole S-oxide + NADP+ + H2O
low activity with FMO2.1, moderate activity with FMO3, high activity with FMO1
-
-
?
methimazole + NADPH + H+ + O2
methimazole S-oxide + NADP+ + H2O
-
substrate of isoforms FMO1, FMO2, and FMO3
-
-
?
methimazole + NADPH + H+ + O2
methimazole S-oxide + NADP+ + H2O
S-oxygenation
-
-
?
methimazole + NADPH + H+ + O2
methimazole S-oxide + NADP+ + H2O
S-oxygenation
-
-
?
methimazole + NADPH + H+ + O2
methimazole S-oxide + NADP+ + H2O
i.e. N-methyl-2-mercaptoimidazole
-
-
?
methimazole + NADPH + O2
?
-
-
-
-
?
methimazole + NADPH + O2
?
-
-
-
?
methimazole + NADPH + O2
?
-
isozyme FMO3
-
-
?
methimazole + NADPH + O2
?
-
liver microsomes
-
-
?
methimazole + NADPH + O2
?
-
-
-
?
methimazole + NADPH + O2
N-methylmethimidazole-2-sulfinic acid + NADP+ + H2O
-
-
-
-
?
methimazole + NADPH + O2
N-methylmethimidazole-2-sulfinic acid + NADP+ + H2O
-
-
-
-
?
methimazole + NADPH + O2
N-methylmethimidazole-2-sulfinic acid + NADP+ + H2O
-
recombinant protein expressed in E. coli
-
-
?
methimazole + NADPH + O2
N-methylmethimidazole-2-sulfinic acid + NADP+ + H2O
-
-
-
-
?
methimazole + NADPH + O2
N-methylmethimidazole-2-sulfinic acid + NADP+ + H2O
-
recombinant protein expressed in E. coli
-
-
?
methimazole + NADPH + O2
N-methylmethimidazole-2-sulfinic acid + NADP+ + H2O
-
FMO3 5000 times more efficient than FMO5
-
-
?
methimazole + NADPH + O2
N-methylmethimidazole-2-sulfinic acid + NADP+ + H2O
-
-
-
-
?
methimazole + NADPH + O2
N-methylmethimidazole-2-sulfinic acid + NADP+ + H2O
-
-
-
-
?
methimazole + NADPH + O2
N-methylmethimidazole-2-sulfinic acid + NADP+ + H2O
-
-
-
-
?
methimazole + NADPH + O2
N-methylmethimidazole-2-sulfinic acid + NADP+ + H2O
-
-
-
-
?
methimazole + NADPH + O2
N-methylmethimidazole-2-sulfinic acid + NADP+ + H2O
-
recombinant protein expressed in E. coli
-
-
?
methimazole + NADPH + O2
N-methylmethimidazole-2-sulfinic acid + NADP+ + H2O
-
-
-
-
?
methimazole + NADPH + O2
N-methylmethimidazole-2-sulfinic acid + NADP+ + H2O
-
-
-
?
methimazole + NADPH + O2
N-methylmethimidazole-2-sulfinic acid + NADP+ + H2O
-
-
-
-
?
methiocarb + NADPH + O2
methiocarb sulfoxide + NADP+ + H2O
-
-
-
-
?
methiocarb + NADPH + O2
methiocarb sulfoxide + NADP+ + H2O
-
i.e. 4-methylthio-3,5-xylyl methylcarbamate, isozyme FMO1 acts stereospecifically, no activity by isozyme FMO3
-
-
?
methyl 4-tolyl sulfide + NADPH + O2
methyl 4-tolyl sulfoxide + NADP+ + H2O
-
-
-
-
?
methyl 4-tolyl sulfide + NADPH + O2
methyl 4-tolyl sulfoxide + NADP+ + H2O
-
-
-
-
?
methyl p-tolyl sulfide + NADPH + H+ + O2
?
-
-
-
?
methyl p-tolyl sulfide + NADPH + H+ + O2
?
-
FMO1, FMO2, but poor substrate of FMO3
-
-
?
methyl p-tolyl sulfide + NADPH + O2
methyl p-tolyl sulfoxide + NADP+ + H2O
-
-
-
-
?
methyl p-tolyl sulfide + NADPH + O2
methyl p-tolyl sulfoxide + NADP+ + H2O
-
-
stereochemistry: product 49% R-enantiomer
?
methyl p-tolyl sulfide + NADPH + O2
methyl p-tolyl sulfoxide + NADP+ + H2O
-
-
26% R
-
?
methylphenylsulfide + NADPH + O2
?
-
-
-
-
?
methylphenylsulfide + NADPH + O2
?
-
-
-
-
?
methylphenylsulfide + NADPH + O2
?
-
-
-
-
?
methylphenylsulfide + NADPH + O2
?
-
-
-
-
?
MK-0767 methyl sulfide + NADPH + H+ + O2
?
a peroxisome proliferator receptor activator, is converted to the S-oxide
-
-
?
MK-0767 methyl sulfide + NADPH + H+ + O2
?
-
substrate of isoforms FMO1 and FMO3
-
-
?
N,N-dimethylaniline + NADPH + H+ + O2
N,N-dimethylaniline N-oxide + NADP+ + H2O
-
-
-
-
?
N,N-dimethylaniline + NADPH + H+ + O2
N,N-dimethylaniline N-oxide + NADP+ + H2O
-
-
-
?
N,N-dimethylaniline + NADPH + H+ + O2
N,N-dimethylaniline N-oxide + NADP+ + H2O
-
-
-
?
N,N-dimethylaniline + NADPH + H+ + O2
N,N-dimethylaniline N-oxide + NADP+ + H2O
-
-
-
?
N,N-dimethylaniline + NADPH + H+ + O2
N,N-dimethylaniline N-oxide + NADP+ + H2O
-
-
-
-
?
N,N-dimethylaniline + NADPH + H+ + O2
N,N-dimethylaniline N-oxide + NADP+ + H2O
-
-
-
?
N,N-dimethylaniline + NADPH + H+ + O2
N,N-dimethylaniline N-oxide + NADP+ + H2O
-
-
-
?
N,N-dimethylaniline + NADPH + H+ + O2
N,N-dimethylaniline N-oxide + NADP+ + H2O
-
-
-
-
?
N,N-dimethylaniline + NADPH + H+ + O2
N,N-dimethylaniline N-oxide + NADP+ + H2O
-
-
-
-
?
N,N-dimethylaniline + NADPH + H+ + O2
N,N-dimethylaniline N-oxide + NADP+ + H2O
-
-
-
?
N,N-dimethylaniline + NADPH + H+ + O2
N,N-dimethylaniline N-oxide + NADP+ + H2O
-
-
-
-
r
N,N-dimethylaniline + NADPH + H+ + O2
N,N-dimethylaniline N-oxide + NADP+ + H2O
-
-
-
-
r
N,N-dimethylaniline + NADPH + O2
N,N-dimethylaniline N-oxide + NADP+ + H2O
-
-
-
-
?
N,N-dimethylaniline + NADPH + O2
N,N-dimethylaniline N-oxide + NADP+ + H2O
-
-
-
-
?
N,N-dimethylaniline + NADPH + O2
N,N-dimethylaniline N-oxide + NADP+ + H2O
-
-
-
-
?
N,N-dimethylaniline + NADPH + O2
N,N-dimethylaniline N-oxide + NADP+ + H2O
-
-
-
-
?
N,N-dimethylaniline + NADPH + O2
N,N-dimethylaniline N-oxide + NADP+ + H2O
-
-
-
-
?
N,N-dimethylaniline + NADPH + O2
N,N-dimethylaniline N-oxide + NADP+ + H2O
-
-
-
-
?
N,N-dimethylaniline + NADPH + O2
N,N-dimethylaniline N-oxide + NADP+ + H2O
-
-
-
-
?
N,N-dimethylaniline + NADPH + O2
N,N-dimethylaniline N-oxide + NADP+ + H2O
-
-
-
-
?
N,N-dimethylaniline + NADPH + O2
N,N-dimethylaniline N-oxide + NADP+ + H2O
-
-
-
-
?
N,N-dimethylaniline + NADPH + O2
N,N-dimethylaniline N-oxide + NADP+ + H2O
-
-
348485, 348486, 348487, 348488, 348490, 348491, 348492, 348494, 348497, 348498, 348499, 348505, 676315 -
-
?
N-aminohomopiperidine + NADPH + O2
?
-
-
-
-
?
N-aminohomopiperidine + NADPH + O2
?
-
-
-
-
?
N-aminohomopiperidine + NADPH + O2
?
-
-
-
-
?
N-aminomorpholine + NADPH + O2
?
-
-
-
-
?
N-aminomorpholine + NADPH + O2
?
-
-
-
-
?
N-aminopiperidine + NADPH + O2
?
-
-
-
-
?
N-aminopiperidine + NADPH + O2
?
-
-
-
-
?
N-aminopiperidine + NADPH + O2
tetrazene + NADP+ + H2O + ?
-
-
-
?
N-aminopiperidine + NADPH + O2
tetrazene + NADP+ + H2O + ?
-
-
-
-
?
N-aminopiperidine + NADPH + O2
tetrazene + NADP+ + H2O + ?
-
-
-
?
N-aminopiperidine + NADPH + O2
tetrazene + NADP+ + H2O + ?
-
-
-
-
?
N-aminopiperidine + NADPH + O2
tetrazene + NADP+ + H2O + ?
-
-
-
?
N-aminopiperidine + NADPH + O2
tetrazene + NADP+ + H2O + ?
-
-
-
-
?
N-aminopyrrolidone + NADPH + O2
?
-
-
-
-
?
N-aminopyrrolidone + NADPH + O2
?
-
-
-
-
?
N-deacetyl ketoconazole + NADPH + H+ + O2
N-deacetyl ketoconazole N-oxide + NADP+ + H2O
an antifungal agent, is converted to the N-hydroxyl
-
-
?
N-deacetyl ketoconazole + NADPH + H+ + O2
N-deacetyl ketoconazole N-oxide + NADP+ + H2O
-
substrate of isoform FMO1
-
-
?
N-deacetyl ketoconazole + NADPH + H+ + O2
N-deacetyl ketoconazole N-oxide + NADP+ + H2O
-
substrate of isoform FMO3
-
-
?
n-decylamine + NADPH + O2
1-nitrosodecane + NADP+ + H2O
-
lung enzyme active, liver enzyme not
-
-
?
n-decylamine + NADPH + O2
1-nitrosodecane + NADP+ + H2O
-
lung enzyme active, liver enzyme not
-
-
?
n-octylamine + NADPH + O2
1-nitrosooctane + NADP+ + H2O
-
recombinant protein expressed in E. coli
-
-
?
n-octylamine + NADPH + O2
1-nitrosooctane + NADP+ + H2O
-
recombinant protein expressed in E. coli
-
-
?
n-octylamine + NADPH + O2
1-nitrosooctane + NADP+ + H2O
-
lung enzyme active, liver enzyme not
-
-
?
n-octylamine + NADPH + O2
1-nitrosooctane + NADP+ + H2O
-
lung enzyme active, liver enzyme not
-
-
?
naphthylthiourea + NADPH + O2
naphthylthiourea S-oxide + NADP+ + H2O
-
isozyme FMO2
-
-
?
naphthylthiourea + NADPH + O2
naphthylthiourea S-oxide + NADP+ + H2O
-
isozyme FMO2
-
-
?
nicotine + NADPH + H+ + O2
nicotine N-oxide + NADP+ + H2O
a stimulant, is converted to the trans-N-oxide
-
-
?
nicotine + NADPH + H+ + O2
nicotine N-oxide + NADP+ + H2O
-
-
-
-
?
olopatadine + NADPH + H+ + O2
olopatadine N-oxide + NADP+ + H2O
an antihistamininc drug, is converted to the N-oxide
-
-
?
olopatadine + NADPH + H+ + O2
olopatadine N-oxide + NADP+ + H2O
an antihistamininc drug, is converted to the N-oxide
-
-
?
olopatadine + NADPH + H+ + O2
olopatadine N-oxide + NADP+ + H2O
-
substrate of isoforms FMO1 and FMO3
-
-
?
p-chloro-N-methylaniline + NADPH + O2
?
-
-
-
-
?
p-chloro-N-methylaniline + NADPH + O2
?
-
-
-
-
?
p-chloro-N-methylaniline + NADPH + O2
?
-
-
-
-
?
p-chloro-N-methylaniline + NADPH + O2
?
-
-
-
-
?
p-tolyl sulfide + NADPH + O2
p-tolyl sulfoxide + NADP+ + H2O
-
S-oxidase activity
-
-
?
p-tolyl sulfide + NADPH + O2
p-tolyl sulfoxide + NADP+ + H2O
-
S-oxidase activity
-
-
?
pentoxifylline + NADPH + H+ + O2
pentoxifylline N-oxide + NADP+ + H2O
-
-
-
?
pentoxifylline + NADPH + H+ + O2
pentoxifylline N-oxide + NADP+ + H2O
-
-
-
?
phenylhydrazine + NADPH + O2
?
-
-
-
-
?
phenylhydrazine + NADPH + O2
?
-
-
-
-
?
phenylthiourea + NADPH + O2
?
-
-
-
-
?
phenylthiourea + NADPH + O2
?
-
-
-
-
?
phenylthiourea + NADPH + O2
?
-
-
-
-
?
phenylthiourea + NADPH + O2
?
-
-
-
-
?
phenylthiourea + NADPH + O2
?
-
-
-
-
?
phenylthiourea + NADPH + O2
phenylthiourea S-oxide + NADP+ + H2O
-
isozyme FMO2
-
-
?
phenylthiourea + NADPH + O2
phenylthiourea S-oxide + NADP+ + H2O
-
isozyme FMO2
-
-
?
procarbazine + NADPH + O2
?
-
-
-
-
?
procarbazine + NADPH + O2
?
-
-
-
-
?
pyrazolacridine + NADPH + H+ + O2
pyrazolacridine N-oxide + NADP+ + H2O
an antitumor drug, is converted to the N-oxide
-
-
?
pyrazolacridine + NADPH + H+ + O2
pyrazolacridine N-oxide + NADP+ + H2O
-
substrate of isoform FMO3
-
-
?
ranitidine + NADPH + H+ + O2
?
an antihistamininc drug, is converted to the N-oxide and/or S-oxide
-
-
?
ranitidine + NADPH + H+ + O2
?
-
substrate of isoforms FMO3 and FMO5, S-oxygenation and N-oxygenation
-
-
?
S-methyl esonarimod + NADPH + H+ + O2
?
a cytokine production inhibitor, is converted to the S-oxide
-
-
?
S-methyl esonarimod + NADPH + H+ + O2
?
-
-
-
-
?
S-methyl esonarimod + NADPH + H+ + O2
S-methyl esonarimod S-oxide + NADP+ + H2O
an cytokine production inhibitor, is converted to the S-oxide
-
-
?
S-methyl esonarimod + NADPH + H+ + O2
S-methyl esonarimod S-oxide + NADP+ + H2O
-
substrate of isoforms FMO1, FMO3, and FMO5
-
-
?
sulfamethoxazole + NADPH + O2
?
bioactivation by isozyme FMO3, not FMO1, results in covalent adduct formation
-
-
?
sulfamethoxazole + NADPH + O2
?
isozyme FMO3, not FMO1
-
-
?
sulindac sulfide + NADPH + H+ + O2
sulindac + NADP+ + H2O
-
S-oxidation, low activity
-
-
?
sulindac sulfide + NADPH + H+ + O2
sulindac + NADP+ + H2O
a nonsteroidal antiinflammatory drug, is converted to the S-oxide
-
-
?
sulindac sulfide + NADPH + H+ + O2
sulindac + NADP+ + H2O
-
S-oxidation
-
-
?
sulindac sulfide + NADPH + H+ + O2
sulindac + NADP+ + H2O
-
-
-
?
tamoxifen + NADPH + H+ + O2
?
-
-
-
-
?
tamoxifen + NADPH + H+ + O2
?
-
i.e. (Z)-2-[4-(1,2-diphenylbut-1-enyl)phenoxy]-N,N-dimethylethanamine
-
-
?
tamoxifen + NADPH + H+ + O2
tamoxifen N-oxide + NADP+ + H2O
-
-
-
?
tamoxifen + NADPH + H+ + O2
tamoxifen N-oxide + NADP+ + H2O
-
-
-
-
?
tamoxifen + NADPH + H+ + O2
tamoxifen N-oxide + NADP+ + H2O
-
-
-
?
tamoxifen + NADPH + H+ + O2
tamoxifen N-oxide + NADP+ + H2O
an estrogen receptor modulator, is converted to the N-oxide
-
-
?
tamoxifen + NADPH + H+ + O2
tamoxifen N-oxide + NADP+ + H2O
an estrogen receptor modulator, is converted to the N-oxide
-
-
?
tamoxifen + NADPH + H+ + O2
tamoxifen N-oxide + NADP+ + H2O
-
substrate of isoforms FMO1 and FMO3
-
-
?
tamoxifen + NADPH + H+ + O2
tamoxifen N-oxide + NADP+ + H2O
tamoxifen is used in breast cancer medication
-
-
?
tamoxifen + NADPH + O2
tamoxifen N-oxide + NADP+ + H2O
-
tamoxifen metabolism pathways involving FMOs and CYP450s, tamoxifen N-oxide is reconverted into tamoxifen by reduced hemoglobin and NADPH-P450 oxidoreductase, a metabolic cycle in vivo, overview
-
-
?
tamoxifen + NADPH + O2
tamoxifen N-oxide + NADP+ + H2O
-
tamoxifen N-oxygenation represents a detoxication pathway, low level of tamoxifen N-oxide production in human liver microsomes may be explained by the kinetics of FMO1 versus FMO3
-
-
?
tamoxifen + NADPH + O2
tamoxifen N-oxide + NADP+ + H2O
-
i.e. (Z)-(1-[4-(2-dimethyl-aminoethoxy)phenyl]-1,2-diphenyl-1-butene), a drug used in breast cancer therapy, isozymes FMO1 and FMO3
-
-
?
tamoxifen + NADPH + O2
tamoxifen N-oxide + NADP+ + H2O
-
i.e. Z-(1-[4-(2-dimethyl-aminoethoxy)phenyl]-1,2-diphenyl-1-butene)
-
-
?
tamoxifen + NADPH + O2
tamoxifen N-oxide + NADP+ + H2O
-
tamoxifen N-oxygenation represents a detoxication pathway, high activity by isozyme FMO1
-
-
?
tamoxifen + NADPH + O2
tamoxifen N-oxide + NADP+ + H2O
-
i.e. Z-(1-[4-(2-dimethyl-aminoethoxy)phenyl]-1,2-diphenyl-1-butene)
-
-
?
tamoxifen + NADPH + O2
tamoxifen N-oxide + NADP+ + H2O
-
tamoxifen N-oxygenation represents a detoxication pathway
-
-
?
tamoxifen + NADPH + O2
tamoxifen N-oxide + NADP+ + H2O
-
i.e. Z-(1-[4-(2-dimethyl-aminoethoxy)phenyl]-1,2-diphenyl-1-butene)
-
-
?
tamoxifen + NADPH + O2
tamoxifen N-oxide + NADP+ + H2O
-
tamoxifen N-oxygenation represents a detoxication pathway
-
-
?
tamoxifen + NADPH + O2
tamoxifen N-oxide + NADP+ + H2O
-
i.e. (Z)-(1-[4-(2-dimethyl-aminoethoxy)phenyl]-1,2-diphenyl-1-butene)
-
-
?
tazarotenic acid + NADPH + H+ + O2
tazarotenate N-oxide + NADP+ + H2O
an retinoic acid receptor modulator, is converted to the S-oxide
-
-
?
tazarotenic acid + NADPH + H+ + O2
tazarotenate N-oxide + NADP+ + H2O
-
substrate of isoforms FMO1 and FMO3
-
-
?
thiacetazone + 2 NADPH + 2 H+ + 2 O2
thiacetazone carbodiimide + 2 NADP+ + 2 H2O
-
bioactivation by isozymes FMO1 and FMO3, two-step process
-
-
?
thiacetazone + 2 NADPH + 2 H+ + 2 O2
thiacetazone carbodiimide + 2 NADP+ + 2 H2O
-
a thiourea-containing second line antitubercular prodrug
-
-
?
thiacetazone + 2 NADPH + 2 H+ + 2 O2
thiacetazone carbodiimide + 2 NADP+ + 2 H2O
-
bioactivation by EtaA
-
-
?
thiacetazone + 2 NADPH + 2 H+ + 2 O2
thiacetazone carbodiimide + 2 NADP+ + 2 H2O
-
a thiourea-containing second line antitubercular prodrug
-
-
?
thiacetazone + NADPH + H+ + O2
?
-
-
-
-
?
thiacetazone + NADPH + H+ + O2
?
a anti-tubercular drug, high activity
-
-
?
thiacetazone + NADPH + H+ + O2
?
an antibiotic agent, is converted to the sulfinic acid/carbodiimide
-
-
?
thiacetazone + NADPH + H+ + O2
?
an antibiotic agent, is converted to the sulfinic acid/carbodiimide
-
-
?
thiacetazone + NADPH + H+ + O2
thiacetazone N-oxide + NADP+ + H2O
an antibiotic agent, is converted to the sulfinic acid/carbodiimide
-
-
?
thiacetazone + NADPH + H+ + O2
thiacetazone N-oxide + NADP+ + H2O
an antibiotic agent, is converted to the sulfinic acid/carbodiimide
-
-
?
thiacetazone + NADPH + H+ + O2
thiacetazone S-oxide + NADP+ + H2O
low activity with FMO1 and FMO3, high activity with FMO2.1
-
-
?
thiacetazone + NADPH + H+ + O2
thiacetazone S-oxide + NADP+ + H2O
-
substrate of isoforms FMO1, FMO2, and FMO3
-
-
?
thioacetamide + NADPH + O2
?
-
-
-
-
?
thioacetamide + NADPH + O2
?
-
-
-
-
?
thioacetamide + NADPH + O2
?
-
-
-
-
?
thioacetamide + NADPH + O2
?
-
-
-
-
?
thiobenzamide + NADPH + O2
?
-
-
-
-
?
thiobenzamide + NADPH + O2
?
-
-
-
-
?
thiobenzamide + NADPH + O2
?
-
-
-
-
?
thiourea + NADPH + H+ + O2
?
-
-
-
-
?
thiourea + NADPH + H+ + O2
?
-
-
-
-
?
thiourea + NADPH + H+ + O2
?
-
-
-
-
?
thiourea + NADPH + O2
?
-
-
-
-
?
thiourea + NADPH + O2
?
-
-
-
-
?
thiourea + NADPH + O2
?
-
-
-
-
?
thiourea + NADPH + O2
?
-
-
-
-
?
thiourea + NADPH + O2
?
-
-
-
-
?
thiourea + NADPH + O2
?
-
-
-
-
?
thiourea + NADPH + O2
thiourea S-oxide + NADP+ + H2O
-
isozyme FMO2
-
-
?
thiourea + NADPH + O2
thiourea S-oxide + NADP+ + H2O
-
-
-
-
?
tigecycline + NADPH + O2
11a-hydroxytigecycline + NADP+ + H2O
-
detoxification, the organism is resistant against the antibiotic
-
-
?
tigecycline + NADPH + O2
11a-hydroxytigecycline + NADP+ + H2O
-
a glycylcycline derivative containing a 9-tert-butylglycylamido group belonging to the tetracyline antibiotic compounds
product identification by LC-MS
-
?
tozasertib + NADPH + H+ + O2
?
-
-
-
-
?
tozasertib + NADPH + H+ + O2
?
-
i.e. N-[4-[4-(4-methylpiperazin-1-yl)-6-[(5-methyl-1H-pyrazol-3-yl)amino]pyrimidin2yl]sulfanylphenyl]cyclopropane carboxamide
-
-
?
trimethylamine + NADPH + H+ + O2
?
-
-
-
-
?
trimethylamine + NADPH + H+ + O2
?
-
-
-
-
?
trimethylamine + NADPH + H+ + O2
?
-
-
-
-
?
trimethylamine + NADPH + H+ + O2
?
-
FMO1, no activity with FMO3 and FMO5
-
-
?
trimethylamine + NADPH + H+ + O2
?
-
-
-
-
?
trimethylamine + NADPH + H+ + O2
trimethylamine N-oxide + NADP+ + H2O
-
-
-
-
?
trimethylamine + NADPH + H+ + O2
trimethylamine N-oxide + NADP+ + H2O
-
-
-
?
trimethylamine + NADPH + H+ + O2
trimethylamine N-oxide + NADP+ + H2O
-
-
-
-
?
trimethylamine + NADPH + H+ + O2
trimethylamine N-oxide + NADP+ + H2O
-
mutations of FMO3 are involved in trimethylaminuria, primary trimethylaminuria is multifactorial in origin in that enzyme dysfunction can result from kinetic incompetencies as well as impaired assembly of holoprotein, overview
-
-
?
trimethylamine + NADPH + H+ + O2
trimethylamine N-oxide + NADP+ + H2O
-
substrate of isoform FMO3
-
-
?
trimethylamine + NADPH + H+ + O2
trimethylamine N-oxide + NADP+ + H2O
KC734478, KC734481, KC734482, KC734486
-
-
-
?
trimethylamine + NADPH + H+ + O2
trimethylamine N-oxide + NADP+ + H2O
-
-
-
-
?
trimethylamine + NADPH + H+ + O2
trimethylamine N-oxide + NADP+ + H2O
-
-
-
-
?
trimethylamine + NADPH + H+ + O2
trimethylamine N-oxide + NADP+ + H2O
-
-
-
-
?
trimethylamine + NADPH + H+ + O2
trimethylamine N-oxide + NADP+ + H2O
-
-
-
-
?
trimethylamine + NADPH + O2
?
-
-
-
-
?
trimethylamine + NADPH + O2
?
-
-
-
-
?
trimethylamine + NADPH + O2
?
-
-
-
-
?
trimethylamine + NADPH + O2
?
-
-
-
-
?
trimethylamine + NADPH + O2
?
-
-
-
-
?
trimethylamine + NADPH + O2
trimethylamine N-oxide + NADP+ + H2O
-
-
-
-
?
trimethylamine + NADPH + O2
trimethylamine N-oxide + NADP+ + H2O
-
isozyme FMO3
-
-
?
trimethylamine + NADPH + O2
trimethylamine N-oxide + NADP+ + H2O
-
preferred substrate of isozyme FMO3
-
-
?
trimethylamine + NADPH + O2
trimethylamine N-oxide + NADP+ + H2O
-
-
-
-
?
trimethylamine + NADPH + O2
trimethylamine N-oxide + NADP+ + H2O
-
-
-
-
?
voriconazole + NADPH + H+ + O2
?
-
-
-
-
?
voriconazole + NADPH + H+ + O2
?
-
liver microsomes, a potent second-generation triazole antifungal agent with broad-spectrum activity against clinically important fungi
-
-
?
voriconazole + NADPH + H+ + O2
?
-
recombinant FMO1 and FMO3, no activity with FMO5, N-oxidation of the fluoropyrimidine ring, its hydroxylation, and hydroxylation of the adjacent methyl group
-
-
?
voriconazole + NADPH + H+ + O2
?
-
substrate of isoforms FMO1 and FMO3
-
-
?
voriconazole + NADPH + H+ + O2
?
-
-
-
-
?
xanomeline + NADPH + H+ + O2
xanomeline N-oxide + NADP+ + H2O
-
-
-
?
xanomeline + NADPH + H+ + O2
xanomeline N-oxide + NADP+ + H2O
a muscarinic receptor antagonist, is converted to the N-oxide
-
-
?
xanomeline + NADPH + H+ + O2
xanomeline N-oxide + NADP+ + H2O
-
substrate of isoforms FMO1 and FMO3
-
-
?
additional information
?
-
enhanced disease susceptibility1, EDS1, controls defense activation and programmed cell death conditioned by intracellular Toll-related immune receptors that recognize specific pathogen effectors in Arabidopsis thaliana, EDS1 is also needed for basal resistance to invasive pathogens by restricting the progression of disease, EDS1 with phytoalexin-deficient 4, PAD4, regulates accumulation of the phenolic defense molecule salicylic acid, EDS1 is regulated by FMO and the Nudix hydrolase NUDT7
-
-
?
additional information
?
-
-
enhanced disease susceptibility1, EDS1, controls defense activation and programmed cell death conditioned by intracellular Toll-related immune receptors that recognize specific pathogen effectors in Arabidopsis thaliana, EDS1 is also needed for basal resistance to invasive pathogens by restricting the progression of disease, EDS1 with phytoalexin-deficient 4, PAD4, regulates accumulation of the phenolic defense molecule salicylic acid, EDS1 is regulated by FMO and the Nudix hydrolase NUDT7
-
-
?
additional information
?
-
-
isozyme FMO1 is an essential component of biologically induced systemic acquired resistance, e.g. versus the bacterial pathogen Pseudomonas syringae pv maculicola, resistance is accompanied by accumulation of salicylic acid, overview
-
-
?
additional information
?
-
-
the enzyme is important for pathogen defense and resistance participating in the detoxification of virulence factors produced by pathogens, overview
-
-
?
additional information
?
-
-
tigecycline displays a broad spectrum of antibacterial activity and circumvents the efflux and ribosomal protection resistance mechanisms, Mg2+-complexing is required for ribosome binding, 11a-hydroxytigecycline forms a weaker complex with magnesium than tigecycline, structure, overview
-
-
?
additional information
?
-
-
benzydamine is a weak base and an indazole derivative with analgesic and antipyretic properties used in human and veterinary medicine, it is metabolized to a wide range of metabolites. One of the main metabolites, benzydamine N-oxide is produced in the liver and brain by flavin-containing monooxygenases
-
-
?
additional information
?
-
-
specificity of FMO-I and FMO-II
-
-
?
additional information
?
-
-
the enzyme does not oxidize glutathione or cysteine
-
-
?
additional information
?
-
-
the enzyme does not oxidize glutathione or cysteine
-
-
?
additional information
?
-
-
comparison of FMO3 and FMO5
-
-
?
additional information
?
-
-
modulation of activity by site directed mutagenesis
-
-
?
additional information
?
-
-
overview on substrate specifities and requirements of FMO1, FMO3
-
-
?
additional information
?
-
-
enzyme regulation, overview
-
-
?
additional information
?
-
arylamine compounds, such as sulfamethoxazole and dapsone, are metabolized in epidermal keratinocytes to arylhydroxylamine metabolites that autooxidize to arylnitroso derivatives, which in turn bind to cellular proteins and can act as antigens/immunogens, methimazole and 4-aminobenzoic acid hydrazide attenuate the protein haptenation, overview
-
-
?
additional information
?
-
-
effects of genetic variants of isozyme FMO3 on N- and S-oxygenation activities, FMO3 polymorphisms are responsible for the genetic disorder trimethylaminuria, or fish-like odor syndrome, overview
-
-
?
additional information
?
-
-
FMO oxygenates a number of drugs and xenobiotics containing a soft-nucleophile heteroatom, mostly sulfur- and nitrogen-containing xenobiotics, isozymes FMO1-FMO3 are involved in detoxication and drug metabolism, FMO3 deficiency causes the disease trimethylaminuria
-
-
?
additional information
?
-
-
FMOs are, together with cytochrome P450 monooxygenases, the major oxidative enzymes in phase I metabolism, extrahepatic metabolism of carbamate and organophosphate thioether compounds, isozyme FMO1 shows higher turnover numbers than isozyme FMO3 for all pesticides studies, overview
-
-
?
additional information
?
-
-
FMOs catalyze NADPH-dependent monooxygenation of soft-nucleophilic nitrogen, sulfur, and phosphorous atoms contained within various drugs, pesticides, and xenobiotics, isozyme FMO3 is responsible for the majority of FMO-mediated xenobiotic metabolism in the adult human liver, FMO3 mutations causing defects in trimethylamine N-oxygenation, result in the disorder known as trimethylaminuria, TMAU, or fish-odour syndrome, overview, interindividual variability in the expression of FMO3 affect drug and exogenous chemical metabolism in the liver and other tissues
-
-
?
additional information
?
-
-
nitrogen- and sulfur-containing endogenous substrates and physiologic functions, FMO is not induced by xenobiotics, isozyme FMO3 mutant alleles contribute to the disease known as trimethylaminuria, the enzyme is involved in detoxification and drug metabolism, overview, expression of FMO5 is markedly down-regulated in the liver of humans with type II diabetes, patients diagnosed with atrial fibrillation document a significant increase in the expression of FMO1, FMO may be associated with sideroblastic anemia, FMO3 mutations lead to trimethylaminuria, detailed overview
-
-
?
additional information
?
-
-
the enzyme catalyzes the NADPH-dependent N-and S-oxidation of a variety of therapeutics, environmental toxicants, carcinogens, and nutrients
-
-
?
additional information
?
-
-
carbophenothion, i.e. S-4-chlorophenylthiomethyl O,O-diethyl phosphorodithioate, and fonofos, i.e. O-ethyl S-phenyl (RS)-ethylphosphonodithioate, are poor substrates
-
-
?
additional information
?
-
-
FMO oxygenates drugs and xenobiotics containing a soft nucleophile, usually nitrogen or sulfur, isozyme substrate specificity, detailed overview, no activity with 1,3-diphenylthiourea
-
-
?
additional information
?
-
-
FMO oxygenates soft nucleophiles, and converts lipophilic compounds into more hydrophilic metabolites, potential adverse drug-drug interactions are minimized for drugs prominently metabolized by FMO, substrate specificities of isozmes, overview
-
-
?
additional information
?
-
-
stereoselectivity of male and female liver microsomes, and of recombinant isozymes FMO1, FMO3, and FMO4, overview
-
-
?
additional information
?
-
drug metabolism, overview, enzyme mutations are involved in development of trimethylaminuria or fish-odor-syndrome, overview
-
-
?
additional information
?
-
drug metabolism, overview, enzyme mutations are involved in development of trimethylaminuria or fish-odor-syndrome, overview
-
-
?
additional information
?
-
drug metabolism, overview, enzyme mutations are involved in development of trimethylaminuria or fish-odor-syndrome, overview
-
-
?
additional information
?
-
-
drug metabolism, overview, enzyme mutations are involved in development of trimethylaminuria or fish-odor-syndrome, overview
-
-
?
additional information
?
-
drug metabolism, overview, most humans are homozygous for a nonsense mutation that inactivates FMO2. But a substantial proportion of sub-Saharan Africans express functional FMO2 and, thus, are predicted to respond differently to drugs and other foreign chemicals
-
-
?
additional information
?
-
drug metabolism, overview, most humans are homozygous for a nonsense mutation that inactivates FMO2. But a substantial proportion of sub-Saharan Africans express functional FMO2 and, thus, are predicted to respond differently to drugs and other foreign chemicals
-
-
?
additional information
?
-
drug metabolism, overview, most humans are homozygous for a nonsense mutation that inactivates FMO2. But a substantial proportion of sub-Saharan Africans express functional FMO2 and, thus, are predicted to respond differently to drugs and other foreign chemicals
-
-
?
additional information
?
-
-
drug metabolism, overview, most humans are homozygous for a nonsense mutation that inactivates FMO2. But a substantial proportion of sub-Saharan Africans express functional FMO2 and, thus, are predicted to respond differently to drugs and other foreign chemicals
-
-
?
additional information
?
-
drug metabolism, overview, the FMO1 gene is downregulated in the spinal cord of patients with the neurodegenerative disease amyotrophic lateral sclerosis, but is upregulated in the myocardial tissue of patients with atrial fibrillation
-
-
?
additional information
?
-
drug metabolism, overview, the FMO1 gene is downregulated in the spinal cord of patients with the neurodegenerative disease amyotrophic lateral sclerosis, but is upregulated in the myocardial tissue of patients with atrial fibrillation
-
-
?
additional information
?
-
drug metabolism, overview, the FMO1 gene is downregulated in the spinal cord of patients with the neurodegenerative disease amyotrophic lateral sclerosis, but is upregulated in the myocardial tissue of patients with atrial fibrillation
-
-
?
additional information
?
-
-
drug metabolism, overview, the FMO1 gene is downregulated in the spinal cord of patients with the neurodegenerative disease amyotrophic lateral sclerosis, but is upregulated in the myocardial tissue of patients with atrial fibrillation
-
-
?
additional information
?
-
FMO2 catalyzes the S-oxygenation of organophosphates representing a detoxification pathway
-
-
?
additional information
?
-
FMO2 catalyzes the S-oxygenation of organophosphates representing a detoxification pathway
-
-
?
additional information
?
-
FMO2 catalyzes the S-oxygenation of organophosphates representing a detoxification pathway
-
-
?
additional information
?
-
FMO2 catalyzes the S-oxygenation of organophosphates representing a detoxification pathway
-
-
?
additional information
?
-
FMO2 catalyzes the S-oxygenation of organophosphates representing a detoxification pathway
-
-
?
additional information
?
-
human FMO3 regulatory elements, overview
-
-
?
additional information
?
-
-
human FMO3 regulatory elements, overview
-
-
?
additional information
?
-
-
the enzyme is regulated by hormones, e.g. testosterone
-
-
?
additional information
?
-
-
FMO1 mediates the formation of a reactive intermediate of 4-fluoro-N-methylaniline. FMO1 catalyzes a carbon oxidation reaction coupled with defluorination that leads to the formation of 4-N-methylaminophenol, mechanism, overview. A labile 1-fluoro-4-(methylimino)cyclohexa-2,5-dienol intermediate is formed leading to an electrophilic quinoneimine intermediate
-
-
?
additional information
?
-
isoform FMO5 exhibits a low catalytic activity only for sulfoxidation of methyl 4-tolyl sulfide
-
-
?
additional information
?
-
-
isoform FMO5 exhibits a low catalytic activity only for sulfoxidation of methyl 4-tolyl sulfide
-
-
?
additional information
?
-
isozyme FMO5 does not metabolize C-1305
-
-
?
additional information
?
-
isozyme FMO5 does not metabolize C-1305
-
-
?
additional information
?
-
-
isozyme FMO5 does not metabolize C-1305
-
-
?
additional information
?
-
comparison of in vivo activity of FMO enzyme with P450 enzme in N-oxygenation of drugs at different pH values, overview
-
-
-
additional information
?
-
-
comparison of in vivo activity of FMO enzyme with P450 enzme in N-oxygenation of drugs at different pH values, overview
-
-
-
additional information
?
-
analysis of the uncoupling reactions in the catalytic cycle of enzyme FMO3, overview. The level of uncoupling varies between 50% and 70% (wild-type) and 90-98% (mutant N61S) for incubations with NADPH and benzydamine over a period of 5 or 20 min, respectively. The substrate lowers the level of uncoupling only related to the H2O2 and not the superoxide radical. In the absence of the substrate benzydamine (BZD), mutant N61S produces higher amounts of H2O2 compared to wild-type
-
-
-
additional information
?
-
-
analysis of the uncoupling reactions in the catalytic cycle of enzyme FMO3, overview. The level of uncoupling varies between 50% and 70% (wild-type) and 90-98% (mutant N61S) for incubations with NADPH and benzydamine over a period of 5 or 20 min, respectively. The substrate lowers the level of uncoupling only related to the H2O2 and not the superoxide radical. In the absence of the substrate benzydamine (BZD), mutant N61S produces higher amounts of H2O2 compared to wild-type
-
-
-
additional information
?
-
formation of a highly stable C4a-hydroperoxyflavin intermediate of hFMO1 upon reduction by NADPH in presence of O2, the intermediate is not fully re-oxidized after 30 min at 15°C in the absence of substrate. The enzyme is below 1% uncoupled in the presence of substrate. Higher stability of the hFMO1 intermediate compared to the stability of the intermediate of isozyme hFMO3
-
-
-
additional information
?
-
-
formation of a highly stable C4a-hydroperoxyflavin intermediate of hFMO1 upon reduction by NADPH in presence of O2, the intermediate is not fully re-oxidized after 30 min at 15°C in the absence of substrate. The enzyme is below 1% uncoupled in the presence of substrate. Higher stability of the hFMO1 intermediate compared to the stability of the intermediate of isozyme hFMO3
-
-
-
additional information
?
-
-
human FMO1 catalyzes the oxygenation of hypotaurine in vitro. Ability of hypotaurine to act as a competitor substrate of FMO1 is assessed by measuring the effect of various concentrations of hypotaurine on FMO1-catalyzed S-oxygenation of methimazole
-
-
-
additional information
?
-
human FMO1 catalyzes the oxygenation of hypotaurine in vitro. Ability of hypotaurine to act as a competitor substrate of FMO1 is assessed by measuring the effect of various concentrations of hypotaurine on FMO1-catalyzed S-oxygenation of methimazole
-
-
-
additional information
?
-
identification of GSK5182 N-oxide products by mass spectrometry
-
-
-
additional information
?
-
-
identification of GSK5182 N-oxide products by mass spectrometry
-
-
-
additional information
?
-
N- and S-oxygenation activity of truncated wild-type human flavin-containing monooxygenase 3 and its common polymorphic variants, overview. The enzyme binds noncovalently one molecule of FAD and is reduced by NADPH before exerting its catalysis
-
-
-
additional information
?
-
-
N- and S-oxygenation activity of truncated wild-type human flavin-containing monooxygenase 3 and its common polymorphic variants, overview. The enzyme binds noncovalently one molecule of FAD and is reduced by NADPH before exerting its catalysis
-
-
-
additional information
?
-
-
S-oxygenation of N-substituted thioureas
-
-
?
additional information
?
-
-
substrate specificity, the ability to stabilize the hydroperoxyflavin intermediate in substrate oxygenation is crucial involving NADP(H), overview
-
-
?
additional information
?
-
-
substrate specificity, the ability to stabilize the hydroperoxyflavin intermediate in substrate oxygenation is crucial involving NADP(H), overview
-
-
?
additional information
?
-
-
substrate specificity of the recombinant PTDH-mFMO fusion enzyme, overview
-
-
?
additional information
?
-
-
substrate specificity of the recombinant PTDH-mFMO fusion enzyme, overview
-
-
?
additional information
?
-
-
overview on specificity
-
-
?
additional information
?
-
-
FMO oxygenates a number of drugs and xenobiotics containing a soft-nucleophile heteroatom, mostly sulfur- and nitrogen-containing xenobiotics, and is involved in detoxication
-
-
?
additional information
?
-
-
nitrogen- and sulfur-containing endogenous substrates and physiologic functions, the enzyme is involved in detoxification and drug metabolism, overview, hepatic total FMO activity is enhanced in mouse models of type I and type II diabetes
-
-
?
additional information
?
-
-
the enzyme is involved in fatty acid oxidation in the liver, as well as in drug detoxification
-
-
?
additional information
?
-
-
regulation of hepatic Fmo isozymes, overview
-
-
?
additional information
?
-
flavin-containing monooxygenases catalyze the addition of oxygen to many sulfur-, nitrogen-, phosphorus-, and selenium-containing compounds including pesticides, therapeutics, and dietary substances
-
-
?
additional information
?
-
flavin-containing monooxygenases catalyze the addition of oxygen to many sulfur-, nitrogen-, phosphorus-, and selenium-containing compounds including pesticides, therapeutics, and dietary substances
-
-
?
additional information
?
-
flavin-containing monooxygenases catalyze the addition of oxygen to many sulfur-, nitrogen-, phosphorus-, and selenium-containing compounds including pesticides, therapeutics, and dietary substances
-
-
?
additional information
?
-
flavin-containing monooxygenases catalyze the addition of oxygen to many sulfur-, nitrogen-, phosphorus-, and selenium-containing compounds including pesticides, therapeutics, and dietary substances
-
-
?
additional information
?
-
flavin-containing monooxygenases catalyze the addition of oxygen to many sulfur-, nitrogen-, phosphorus-, and selenium-containing compounds including pesticides, therapeutics, and dietary substances
-
-
?
additional information
?
-
-
flavin-containing monooxygenases catalyze the addition of oxygen to many sulfur-, nitrogen-, phosphorus-, and selenium-containing compounds including pesticides, therapeutics, and dietary substances
-
-
?
additional information
?
-
in vitro microsomal Baeyer-Villiger oxidation of pentoxifylline (PTX) by Fmo5
-
-
-
additional information
?
-
-
in vitro microsomal Baeyer-Villiger oxidation of pentoxifylline (PTX) by Fmo5
-
-
-
additional information
?
-
flavin-containing monooxygenases catalyze the addition of oxygen to many sulfur-, nitrogen-, phosphorus-, and selenium-containing compounds including pesticides, therapeutics, and dietary substances
-
-
?
additional information
?
-
flavin-containing monooxygenases catalyze the addition of oxygen to many sulfur-, nitrogen-, phosphorus-, and selenium-containing compounds including pesticides, therapeutics, and dietary substances
-
-
?
additional information
?
-
flavin-containing monooxygenases catalyze the addition of oxygen to many sulfur-, nitrogen-, phosphorus-, and selenium-containing compounds including pesticides, therapeutics, and dietary substances
-
-
?
additional information
?
-
flavin-containing monooxygenases catalyze the addition of oxygen to many sulfur-, nitrogen-, phosphorus-, and selenium-containing compounds including pesticides, therapeutics, and dietary substances
-
-
?
additional information
?
-
flavin-containing monooxygenases catalyze the addition of oxygen to many sulfur-, nitrogen-, phosphorus-, and selenium-containing compounds including pesticides, therapeutics, and dietary substances
-
-
?
additional information
?
-
in vitro microsomal Baeyer-Villiger oxidation of pentoxifylline (PTX) by Fmo5
-
-
-
additional information
?
-
-
no activity with glutathione
-
-
?
additional information
?
-
regulation of the enzyme expression by hypersaline conditions and the osmoregulatory hormonecortisol, overview
-
-
?
additional information
?
-
-
regulation of the enzyme expression by hypersaline conditions and the osmoregulatory hormonecortisol, overview
-
-
?
additional information
?
-
-
overview on specificity
-
-
?
additional information
?
-
-
nitrogen- and sulfur-containing endogenous substrates and physiologic functions, the enzyme is involved in detoxification and drug metabolism, overview
-
-
?
additional information
?
-
the enzyme is involved in oxidative metabolism of drugs and other chemicals
-
-
?
additional information
?
-
-
the enzyme is involved in oxidative metabolism of drugs and other chemicals
-
-
?
additional information
?
-
-
stereoselectivity of recombinant isozymes FMO1, FMO2, and FMO3
-
-
?
additional information
?
-
-
the lung isozyme is distinct from the liver isozyme in having high activity toward primary alkyl amines, restricted substrate specificity related to steric properties, resistance to detergent inhibition and enhanced thermal stability, and restricted substrate access, no activity of the lung isozyme with 1,3-diphenylthiourea, chlorpromazine and imipramine by isozyme FMO2, isozyme substrate specificity, detailed overview
-
-
?
additional information
?
-
-
benzydamine is a weak base and an indazole derivative with analgesic and antipyretic properties used in human and veterinary medicine, it is metabolized to a wide range of metabolites. One of the main metabolites, benzydamine N-oxide is produced in the liver and brain by flavin-containing monooxygenases
-
-
?
additional information
?
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-
the enzyme is involved in detoxification, generally, metabolites produced by FMO-catalysed reactions are more hydrophilic and less toxic, and are easily excreted from the body
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additional information
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substrates are a wide range of nucleophilic nitrogen-, sulfur-, phosphorus-, and selenium heteroatom-containing chemicals, drugs, and agricultural agents
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additional information
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overview on specificity
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additional information
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FMO oxygenates a number of drugs and xenobiotics containing a soft-nucleophile heteroatom, mostly sulfur- and nitrogen-containing xenobiotics, and is involved in detoxication
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additional information
?
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the enzyme plays an important role in drug metabolism, insulin itself has no effect on FMO1 activity in non-diabetic animals, but hepatic isozyme FMO1 and intestinal CYP3A activity are correlated with average blood glucose concentration in untreated diabetic rats, and insulin reduces CYP3A activity, thus also regulates FMO1 indirectly
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additional information
?
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stereoselectivity of purified isozymes FMO1 and FMO3, overview
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additional information
?
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isozyme FMO5 does not metabolize 5-[[3-(dimethylamino)propyl]amino]-8-hydroxy-6H-[1,2,3]triazolo[4,5,1-de]acridin-6-one (C-1305)
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?
additional information
?
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the substrate specificity of Saccharomyces cerevisiae FMO is more restricted than that of mammalian FMOs, reflecting its role in maintaining redox balance in the cell
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additional information
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additional information
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reaction can be functionally separated into 2 partial reactions: 1. a reduced pyridine nucleotide and oxygen-dependent N-oxide synthase, 2. an N-oxide dealkylase
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?
additional information
?
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catalyzes NADPH- and O2-dependent N-oxidation of N-substituted amines and hydrazines and the S-oxidation of thioureylenes and thiols
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?
additional information
?
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-
catalyzes NADPH- and O2-dependent N-oxidation of N-substituted amines and hydrazines and the S-oxidation of thioureylenes and thiols
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?
additional information
?
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-
S-oxygenation of N-substituted thioureas
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?
additional information
?
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study of oxidative half-reaction
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?
additional information
?
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study of reductive half-reaction
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?
additional information
?
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-
FMO oxygenates a number of drugs and xenobiotics containing a soft-nucleophile heteroatom, mostly sulfur- and nitrogen-containing xenobiotics, and is involved in detoxication
-
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?
additional information
?
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-
nitrogen- and sulfur-containing endogenous substrates and physiologic functions, the enzyme is involved in detoxification and drug metabolism, overview
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?
additional information
?
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FMO oxygenates oxygenates a wide range of sulfur- and nitrogen-containing xenobiotics and, in some cases, also oxygenates selenium, iodine, boron, phosphorus and even carbon, it oxidizes drugs and xenobiotics containing a soft nucleophile, usually nitrogen or sulfur, utilizing the reducing equivalents of NADPH to reduce 1 atom of molecular oxygen to water, while the other atom is used to oxidize the substrate, FMO does not require a reductase to transfer electrons from NADPH, liver isozyme FMO1 shows a very promiscuous substrate specificity, isozyme substrate specificity, detailed overview
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additional information
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benzydamine is a weak base and an indazole derivative with analgesic and antipyretic properties used in human and veterinary medicine, it is metabolized to a wide range of metabolites. One of the main metabolites, benzydamine N-oxide is produced in the liver and brain by flavin-containing monooxygenases
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Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
(S)-nicotine + NADPH + O2
(S)-nicotine N1-oxide + NADP+ + H2O
-
(S)-nicotine N-1'-oxygenation
-
-
?
1,1-dimethylhydrazine + NADPH + O2
formaldehyde + CH3N2H3 + NADP+
1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine + NADPH + H+ + O2
1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine N-oxide + NADP+ + H2O
10-(N,N-dimethylaminopentyl)-2-(trifluoromethyl)phenothiazine + NADPH + O2
?
-
-
-
-
?
10-N-(n-octylamino)-2-(trifluoromethyl) phenothiazine + NADPH + O2
10-N-(n-octylamino)-2-(trifluoromethyl) phenothiazine N-oxide + NADP+ + H2O
-
-
-
-
?
3-hydroxy-nabumetone + NADPH + H+ + O2
? + NADP+ + H2O
activation reaction
-
-
?
4-aminobenzoic acid hydrazide + NADPH + O2
?
-
-
-
?
amphetamine + NADPH + O2
amphetamine N-oxide + NADP+ + H2O
-
-
-
-
?
benzydamine + NADPH + H+ + O2
benzydamine N-oxide + NADP+ + H2O
benzylamine + [reduced NADPH-hemoprotein reductase] + O2
benzylamine N-oxide + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
-
-
?
chlorpromazine + NADPH + H+ + O2
chlorpromazine N-oxide + NADP+ + H2O
-
-
-
?
cimetidine + NADPH + O2
cimetidine S-oxide + NADP+ + H2O
-
-
-
-
?
clomiphene + NADPH + H+ + O2
clomiphene N-oxide + NADP+ + H2O
clomiphene is used in infertility medication
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-
?
clomipramine + NADPH + H+ + O2
clomipramine N-oxide + NADP+ + H2O
-
-
-
?
clozapine + NADPH + H+ + O2
clozapine N-oxide + NADP+ + H2O
-
-
-
?
clozapine + NADPH + O2
?
-
-
-
-
?
cysteamine + NADPH + O2
cysteamine N-oxide + NADP+ + H2O
dapsone + NADPH + O2
?
bioactivation by isozyme FMO3, not FMO1, results in covalent adduct formation
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-
?
dasatinib + NADPH + H+ + O2
dasatinib N-oxide + NADP+ + H2O
-
-
-
?
demeton-O + NADPH + O2
demeton-O sulfoxide + NADP+ + H2O
-
-
-
-
?
dihydrolipoic acid + NADPH + O2
?
-
-
-
-
?
ethiofencarb + NADPH + O2
ethiofencarb sulfoxide + NADP+ + H2O
-
-
-
-
?
ethionamide + NADPH + H+ + O2
ethionamide S-oxide + NADP+ + H2O
ethionamide + NADPH + O2 + H+
2-ethyl-N-hydroxypyridine-4-carbothioamide + NADP+ + H2O
fenthion + NADPH + O2
fenthion sulfoxide + NADP+ + H2O
-
-
-
-
?
GSK5182 + NADPH + H+ + O2
GSK5182 N-oxide + NADP+ + H2O
an antidiabetic lead molecule
-
-
?
hypotaurine + H2O + NAD+
taurine + NADH
-
metabolism of cysteine
-
?
hypotaurine + NADH + H+ + O2
taurine + NAD+ + H2O
hypotaurine + NADPH + H+ + O2
taurine + NADP+ + H2O
imipramine + NADPH + O2
?
-
-
-
-
?
indole + NADPH + H+ + O2
indole N-oxide + NADP+ + H2O
itopride + NADPH + H+ + O2
itopride N-oxide + NADP+ + H2O
itopride + NADPH + O2
?
-
-
-
-
?
L-methionine + NADPH + O2
L-methionine S-oxide + NADP+ + H2O
lipoic acid + NADPH + O2
?
loxapine + NADPH + H+ + O2
loxapine N-oxide + NADP+ + H2O
-
-
-
?
methimazole + NADPH + O2
?
methiocarb + NADPH + O2
methiocarb sulfoxide + NADP+ + H2O
-
-
-
-
?
methyl 4-tolyl sulfide + NADPH + O2
methyl 4-tolyl sulfoxide + NADP+ + H2O
-
-
-
-
?
methylthioalkyl glucosinolate + NADPH + H+ + O2
methylsulfinylalkyl glucosinolate S-oxide + NADP+ + H2O
-
-
-
-
?
N,N-dimethylamphetamine + NADPH + H+ + O2
N,N-dimethylamphetamine N-oxide + NADP+ + H2O
N-oxygenation mainly by isozyme FMO1, low activity with isozyme FMO3
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-
?
N,N-dimethylaniline + NADH + H+ + O2
N,N-dimethylaniline N-oxide + NAD+ + H2O
-
-
-
-
?
N,N-dimethylaniline + NADPH + H+ + O2
N,N-dimethylaniline N-oxide + NADP+ + H2O
N,N-dimethylaniline + NADPH + O2
N,N-dimethylaniline N-oxide + NADP+ + H2O
phenethylamine + NADPH + O2
phenethylamine N-oxide + NADP+ + H2O
-
isozyme FMO3
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?
ranitidine + NADPH + O2
?
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-
-
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?
S-farnesylcysteine + NADPH + O2
S-farnesylcysteine S-oxide + NADP+ + H2O
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-
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?
S-farnesylcysteine methyl ester + NADPH + O2
?
-
-
-
-
?
selegiline + NADPH + O2
selegiline N-oxide + NADP+
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-
-
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?
sulfamethoxazole + NADPH + O2
?
bioactivation by isozyme FMO3, not FMO1, results in covalent adduct formation
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?
sulindac sulfide + NADPH + O2
(S,R)-sulindac + NADP+ + H2O
-
-
-
-
?
tamoxifen + NADPH + H+ + O2
tamoxifen N-oxide + NADP+ + H2O
tamoxifen + NADPH + O2
tamoxifen N-oxide + NADP+ + H2O
thiacetazone + 2 NADPH + 2 H+ + 2 O2
thiacetazone carbodiimide + 2 NADP+ + 2 H2O
thiacetazone + 2 NADPH + 2 O2
(E)-{(2E)-[4-(acetylamino)benzylidene]hydrazinylidene}(amino)methanesulfinic acid + 2 NADP+ + H2O
-
bioactivation by EtaA
-
-
?
tigecycline + NADPH + O2
11a-hydroxytigecycline + NADP+ + H2O
-
detoxification, the organism is resistant against the antibiotic
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-
?
tozasertib + NADPH + H+ + O2
tozasertib N-oxide + NADP+ + H2O
-
-
-
?
trimethylamine + NADPH + H+ + O2
trimethylamine N-oxide + NADP+ + H2O
trimethylamine + NADPH + O2
trimethylamine N-oxide + NADP+ + H2O
tyramine + NADPH + O2
tyramine N-oxide + NADP+ + H2O
-
-
-
-
?
voriconazole + NADPH + H+ + O2
?
-
liver microsomes, a potent second-generation triazole antifungal agent with broad-spectrum activity against clinically important fungi
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-
?
xanomeline + NADPH + H+ + O2
xanomeline N-oxide + NADP+ + H2O
-
-
-
?
[7-(2,6-dichloro-phenyl)-5-methyl-benzo[1,2,4]triazin-3-yl]-[4-(2-pyrrolidin-1-yl-ethoxy)-phenyl]-amine + NADPH + H+ + O2
[7-(2,6-dichlorophenyl)-5-methyl-benzo[1,2,4]triazin-3-yl]-(4-[2-(1-oxy-pyrrolidin-1-yl)-ethoxy]-phenyl)-amine + NADP+ + H2O
-
i.e. TG100435, a multitargeted Src family kinase inhibitor with anticancer activity, FMO3 is the primary enzyme responsible for TG100855 formation, enzyme-mediated retroreduction of TG100855 back to TG100435 is observed catalyzed by a cytochrome P450 reductase, overview
i.e. TG100855, the N-oxide product is also a multitargeted Src family kinase inhibitor with anticancer activity
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?
additional information
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1,1-dimethylhydrazine + NADPH + O2
formaldehyde + CH3N2H3 + NADP+
-
possibly, and other 1,1-disubstituted hydrazines
-
?
1,1-dimethylhydrazine + NADPH + O2
formaldehyde + CH3N2H3 + NADP+
-
possibly, and other 1,1-disubstituted hydrazines
-
?
1,1-dimethylhydrazine + NADPH + O2
formaldehyde + CH3N2H3 + NADP+
-
possibly, and other 1,1-disubstituted hydrazines
-
?
1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine + NADPH + H+ + O2
1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine N-oxide + NADP+ + H2O
-
reaction in microsomal detoxification pathway of 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine, a neurotoxin to nigrostriatal dopaminergic neurons
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-
?
1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine + NADPH + H+ + O2
1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine N-oxide + NADP+ + H2O
-
reaction in microsomal detoxification pathway of 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine, a neurotoxin to nigrostriatal dopaminergic neurons
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-
?
1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine + NADPH + H+ + O2
1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine N-oxide + NADP+ + H2O
-
one of the predominant enzmyes responsible for the oxygenation of 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine
-
-
?
benzydamine + NADPH + H+ + O2
benzydamine N-oxide + NADP+ + H2O
-
-
-
-
?
benzydamine + NADPH + H+ + O2
benzydamine N-oxide + NADP+ + H2O
-
-
-
?
benzydamine + NADPH + H+ + O2
benzydamine N-oxide + NADP+ + H2O
-
-
-
-
?
benzydamine + NADPH + H+ + O2
benzydamine N-oxide + NADP+ + H2O
-
-
-
-
?
benzydamine + NADPH + H+ + O2
benzydamine N-oxide + NADP+ + H2O
-
-
-
-
?
cysteamine + NADPH + O2
cysteamine N-oxide + NADP+ + H2O
-
-
-
-
?
cysteamine + NADPH + O2
cysteamine N-oxide + NADP+ + H2O
-
-
-
-
?
cysteamine + NADPH + O2
cysteamine N-oxide + NADP+ + H2O
-
-
-
-
?
cysteamine + NADPH + O2
cysteamine N-oxide + NADP+ + H2O
-
-
-
-
?
ethionamide + NADPH + H+ + O2
ethionamide S-oxide + NADP+ + H2O
ethionamide is a pro-drug requiring bioactivation to exert toxicity
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-
?
ethionamide + NADPH + H+ + O2
ethionamide S-oxide + NADP+ + H2O
ethionamide is a pro-drug requiring bioactivation to exert toxicity
-
-
?
ethionamide + NADPH + O2 + H+
2-ethyl-N-hydroxypyridine-4-carbothioamide + NADP+ + H2O
-
bioactivation by isozymes FMO1 and FMO3
-
-
?
ethionamide + NADPH + O2 + H+
2-ethyl-N-hydroxypyridine-4-carbothioamide + NADP+ + H2O
-
bioactivation by EtaA
-
-
?
hypotaurine + NADH + H+ + O2
taurine + NAD+ + H2O
S-oxygenation
-
-
?
hypotaurine + NADH + H+ + O2
taurine + NAD+ + H2O
S-oxygenation
-
-
?
hypotaurine + NADPH + H+ + O2
taurine + NADP+ + H2O
S-oxygenation
-
-
?
hypotaurine + NADPH + H+ + O2
taurine + NADP+ + H2O
S-oxygenation
-
-
?
indole + NADPH + H+ + O2
indole N-oxide + NADP+ + H2O
-
-
-
-
?
indole + NADPH + H+ + O2
indole N-oxide + NADP+ + H2O
-
-
-
-
?
itopride + NADPH + H+ + O2
itopride N-oxide + NADP+ + H2O
-
-
-
?
itopride + NADPH + H+ + O2
itopride N-oxide + NADP+ + H2O
-
-
-
-
?
L-methionine + NADPH + O2
L-methionine S-oxide + NADP+ + H2O
-
-
-
-
?
L-methionine + NADPH + O2
L-methionine S-oxide + NADP+ + H2O
-
-
-
-
?
L-methionine + NADPH + O2
L-methionine S-oxide + NADP+ + H2O
-
-
-
-
?
L-methionine + NADPH + O2
L-methionine S-oxide + NADP+ + H2O
-
-
-
-
?
lipoic acid + NADPH + O2
?
-
-
-
-
?
lipoic acid + NADPH + O2
?
-
-
-
-
?
methimazole + NADPH + O2
?
-
-
-
-
?
methimazole + NADPH + O2
?
-
-
-
?
methimazole + NADPH + O2
?
-
-
-
?
N,N-dimethylaniline + NADPH + H+ + O2
N,N-dimethylaniline N-oxide + NADP+ + H2O
-
-
-
-
?
N,N-dimethylaniline + NADPH + H+ + O2
N,N-dimethylaniline N-oxide + NADP+ + H2O
-
-
-
?
N,N-dimethylaniline + NADPH + H+ + O2
N,N-dimethylaniline N-oxide + NADP+ + H2O
-
-
-
?
N,N-dimethylaniline + NADPH + H+ + O2
N,N-dimethylaniline N-oxide + NADP+ + H2O
-
-
-
?
N,N-dimethylaniline + NADPH + H+ + O2
N,N-dimethylaniline N-oxide + NADP+ + H2O
-
-
-
-
?
N,N-dimethylaniline + NADPH + H+ + O2
N,N-dimethylaniline N-oxide + NADP+ + H2O
-
-
-
?
N,N-dimethylaniline + NADPH + H+ + O2
N,N-dimethylaniline N-oxide + NADP+ + H2O
-
-
-
?
N,N-dimethylaniline + NADPH + H+ + O2
N,N-dimethylaniline N-oxide + NADP+ + H2O
-
-
-
-
?
N,N-dimethylaniline + NADPH + H+ + O2
N,N-dimethylaniline N-oxide + NADP+ + H2O
-
-
-
-
?
N,N-dimethylaniline + NADPH + H+ + O2
N,N-dimethylaniline N-oxide + NADP+ + H2O
-
-
-
?
N,N-dimethylaniline + NADPH + O2
N,N-dimethylaniline N-oxide + NADP+ + H2O
-
-
-
-
?
N,N-dimethylaniline + NADPH + O2
N,N-dimethylaniline N-oxide + NADP+ + H2O
-
-
-
-
?
N,N-dimethylaniline + NADPH + O2
N,N-dimethylaniline N-oxide + NADP+ + H2O
-
-
-
-
?
N,N-dimethylaniline + NADPH + O2
N,N-dimethylaniline N-oxide + NADP+ + H2O
-
-
-
-
?
tamoxifen + NADPH + H+ + O2
tamoxifen N-oxide + NADP+ + H2O
-
-
-
?
tamoxifen + NADPH + H+ + O2
tamoxifen N-oxide + NADP+ + H2O
tamoxifen is used in breast cancer medication
-
-
?
tamoxifen + NADPH + O2
tamoxifen N-oxide + NADP+ + H2O
-
tamoxifen metabolism pathways involving FMOs and CYP450s, tamoxifen N-oxide is reconverted into tamoxifen by reduced hemoglobin and NADPH-P450 oxidoreductase, a metabolic cycle in vivo, overview
-
-
?
tamoxifen + NADPH + O2
tamoxifen N-oxide + NADP+ + H2O
-
tamoxifen N-oxygenation represents a detoxication pathway, low level of tamoxifen N-oxide production in human liver microsomes may be explained by the kinetics of FMO1 versus FMO3
-
-
?
tamoxifen + NADPH + O2
tamoxifen N-oxide + NADP+ + H2O
-
tamoxifen N-oxygenation represents a detoxication pathway, high activity by isozyme FMO1
-
-
?
tamoxifen + NADPH + O2
tamoxifen N-oxide + NADP+ + H2O
-
tamoxifen N-oxygenation represents a detoxication pathway
-
-
?
tamoxifen + NADPH + O2
tamoxifen N-oxide + NADP+ + H2O
-
tamoxifen N-oxygenation represents a detoxication pathway
-
-
?
thiacetazone + 2 NADPH + 2 H+ + 2 O2
thiacetazone carbodiimide + 2 NADP+ + 2 H2O
-
bioactivation by isozymes FMO1 and FMO3, two-step process
-
-
?
thiacetazone + 2 NADPH + 2 H+ + 2 O2
thiacetazone carbodiimide + 2 NADP+ + 2 H2O
-
bioactivation by EtaA
-
-
?
trimethylamine + NADPH + H+ + O2
trimethylamine N-oxide + NADP+ + H2O
-
-
-
-
?
trimethylamine + NADPH + H+ + O2
trimethylamine N-oxide + NADP+ + H2O
-
-
-
?
trimethylamine + NADPH + H+ + O2
trimethylamine N-oxide + NADP+ + H2O
-
-
-
-
?
trimethylamine + NADPH + H+ + O2
trimethylamine N-oxide + NADP+ + H2O
-
mutations of FMO3 are involved in trimethylaminuria, primary trimethylaminuria is multifactorial in origin in that enzyme dysfunction can result from kinetic incompetencies as well as impaired assembly of holoprotein, overview
-
-
?
trimethylamine + NADPH + O2
trimethylamine N-oxide + NADP+ + H2O
-
-
-
-
?
trimethylamine + NADPH + O2
trimethylamine N-oxide + NADP+ + H2O
-
preferred substrate of isozyme FMO3
-
-
?
trimethylamine + NADPH + O2
trimethylamine N-oxide + NADP+ + H2O
-
-
-
-
?
trimethylamine + NADPH + O2
trimethylamine N-oxide + NADP+ + H2O
-
-
-
-
?
additional information
?
-
enhanced disease susceptibility1, EDS1, controls defense activation and programmed cell death conditioned by intracellular Toll-related immune receptors that recognize specific pathogen effectors in Arabidopsis thaliana, EDS1 is also needed for basal resistance to invasive pathogens by restricting the progression of disease, EDS1 with phytoalexin-deficient 4, PAD4, regulates accumulation of the phenolic defense molecule salicylic acid, EDS1 is regulated by FMO and the Nudix hydrolase NUDT7
-
-
?
additional information
?
-
-
enhanced disease susceptibility1, EDS1, controls defense activation and programmed cell death conditioned by intracellular Toll-related immune receptors that recognize specific pathogen effectors in Arabidopsis thaliana, EDS1 is also needed for basal resistance to invasive pathogens by restricting the progression of disease, EDS1 with phytoalexin-deficient 4, PAD4, regulates accumulation of the phenolic defense molecule salicylic acid, EDS1 is regulated by FMO and the Nudix hydrolase NUDT7
-
-
?
additional information
?
-
-
isozyme FMO1 is an essential component of biologically induced systemic acquired resistance, e.g. versus the bacterial pathogen Pseudomonas syringae pv maculicola, resistance is accompanied by accumulation of salicylic acid, overview
-
-
?
additional information
?
-
-
the enzyme is important for pathogen defense and resistance participating in the detoxification of virulence factors produced by pathogens, overview
-
-
?
additional information
?
-
-
tigecycline displays a broad spectrum of antibacterial activity and circumvents the efflux and ribosomal protection resistance mechanisms, Mg2+-complexing is required for ribosome binding, 11a-hydroxytigecycline forms a weaker complex with magnesium than tigecycline, structure, overview
-
-
?
additional information
?
-
-
benzydamine is a weak base and an indazole derivative with analgesic and antipyretic properties used in human and veterinary medicine, it is metabolized to a wide range of metabolites. One of the main metabolites, benzydamine N-oxide is produced in the liver and brain by flavin-containing monooxygenases
-
-
?
additional information
?
-
-
enzyme regulation, overview
-
-
?
additional information
?
-
arylamine compounds, such as sulfamethoxazole and dapsone, are metabolized in epidermal keratinocytes to arylhydroxylamine metabolites that autooxidize to arylnitroso derivatives, which in turn bind to cellular proteins and can act as antigens/immunogens, methimazole and 4-aminobenzoic acid hydrazide attenuate the protein haptenation, overview
-
-
?
additional information
?
-
-
effects of genetic variants of isozyme FMO3 on N- and S-oxygenation activities, FMO3 polymorphisms are responsible for the genetic disorder trimethylaminuria, or fish-like odor syndrome, overview
-
-
?
additional information
?
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FMO oxygenates a number of drugs and xenobiotics containing a soft-nucleophile heteroatom, mostly sulfur- and nitrogen-containing xenobiotics, isozymes FMO1-FMO3 are involved in detoxication and drug metabolism, FMO3 deficiency causes the disease trimethylaminuria
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additional information
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FMOs are, together with cytochrome P450 monooxygenases, the major oxidative enzymes in phase I metabolism, extrahepatic metabolism of carbamate and organophosphate thioether compounds, isozyme FMO1 shows higher turnover numbers than isozyme FMO3 for all pesticides studies, overview
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additional information
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FMOs catalyze NADPH-dependent monooxygenation of soft-nucleophilic nitrogen, sulfur, and phosphorous atoms contained within various drugs, pesticides, and xenobiotics, isozyme FMO3 is responsible for the majority of FMO-mediated xenobiotic metabolism in the adult human liver, FMO3 mutations causing defects in trimethylamine N-oxygenation, result in the disorder known as trimethylaminuria, TMAU, or fish-odour syndrome, overview, interindividual variability in the expression of FMO3 affect drug and exogenous chemical metabolism in the liver and other tissues
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additional information
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nitrogen- and sulfur-containing endogenous substrates and physiologic functions, FMO is not induced by xenobiotics, isozyme FMO3 mutant alleles contribute to the disease known as trimethylaminuria, the enzyme is involved in detoxification and drug metabolism, overview, expression of FMO5 is markedly down-regulated in the liver of humans with type II diabetes, patients diagnosed with atrial fibrillation document a significant increase in the expression of FMO1, FMO may be associated with sideroblastic anemia, FMO3 mutations lead to trimethylaminuria, detailed overview
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additional information
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the enzyme catalyzes the NADPH-dependent N-and S-oxidation of a variety of therapeutics, environmental toxicants, carcinogens, and nutrients
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additional information
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drug metabolism, overview, enzyme mutations are involved in development of trimethylaminuria or fish-odor-syndrome, overview
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additional information
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drug metabolism, overview, enzyme mutations are involved in development of trimethylaminuria or fish-odor-syndrome, overview
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additional information
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drug metabolism, overview, enzyme mutations are involved in development of trimethylaminuria or fish-odor-syndrome, overview
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additional information
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drug metabolism, overview, enzyme mutations are involved in development of trimethylaminuria or fish-odor-syndrome, overview
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additional information
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drug metabolism, overview, most humans are homozygous for a nonsense mutation that inactivates FMO2. But a substantial proportion of sub-Saharan Africans express functional FMO2 and, thus, are predicted to respond differently to drugs and other foreign chemicals
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additional information
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drug metabolism, overview, most humans are homozygous for a nonsense mutation that inactivates FMO2. But a substantial proportion of sub-Saharan Africans express functional FMO2 and, thus, are predicted to respond differently to drugs and other foreign chemicals
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additional information
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drug metabolism, overview, most humans are homozygous for a nonsense mutation that inactivates FMO2. But a substantial proportion of sub-Saharan Africans express functional FMO2 and, thus, are predicted to respond differently to drugs and other foreign chemicals
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additional information
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drug metabolism, overview, most humans are homozygous for a nonsense mutation that inactivates FMO2. But a substantial proportion of sub-Saharan Africans express functional FMO2 and, thus, are predicted to respond differently to drugs and other foreign chemicals
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additional information
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drug metabolism, overview, the FMO1 gene is downregulated in the spinal cord of patients with the neurodegenerative disease amyotrophic lateral sclerosis, but is upregulated in the myocardial tissue of patients with atrial fibrillation
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additional information
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drug metabolism, overview, the FMO1 gene is downregulated in the spinal cord of patients with the neurodegenerative disease amyotrophic lateral sclerosis, but is upregulated in the myocardial tissue of patients with atrial fibrillation
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additional information
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drug metabolism, overview, the FMO1 gene is downregulated in the spinal cord of patients with the neurodegenerative disease amyotrophic lateral sclerosis, but is upregulated in the myocardial tissue of patients with atrial fibrillation
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additional information
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drug metabolism, overview, the FMO1 gene is downregulated in the spinal cord of patients with the neurodegenerative disease amyotrophic lateral sclerosis, but is upregulated in the myocardial tissue of patients with atrial fibrillation
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additional information
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FMO2 catalyzes the S-oxygenation of organophosphates representing a detoxification pathway
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additional information
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FMO2 catalyzes the S-oxygenation of organophosphates representing a detoxification pathway
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additional information
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FMO2 catalyzes the S-oxygenation of organophosphates representing a detoxification pathway
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additional information
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FMO2 catalyzes the S-oxygenation of organophosphates representing a detoxification pathway
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additional information
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FMO2 catalyzes the S-oxygenation of organophosphates representing a detoxification pathway
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additional information
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human FMO3 regulatory elements, overview
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additional information
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human FMO3 regulatory elements, overview
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additional information
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the enzyme is regulated by hormones, e.g. testosterone
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additional information
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comparison of in vivo activity of FMO enzyme with P450 enzme in N-oxygenation of drugs at different pH values, overview
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additional information
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comparison of in vivo activity of FMO enzyme with P450 enzme in N-oxygenation of drugs at different pH values, overview
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additional information
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FMO oxygenates a number of drugs and xenobiotics containing a soft-nucleophile heteroatom, mostly sulfur- and nitrogen-containing xenobiotics, and is involved in detoxication
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additional information
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nitrogen- and sulfur-containing endogenous substrates and physiologic functions, the enzyme is involved in detoxification and drug metabolism, overview, hepatic total FMO activity is enhanced in mouse models of type I and type II diabetes
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additional information
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the enzyme is involved in fatty acid oxidation in the liver, as well as in drug detoxification
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additional information
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regulation of hepatic Fmo isozymes, overview
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additional information
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flavin-containing monooxygenases catalyze the addition of oxygen to many sulfur-, nitrogen-, phosphorus-, and selenium-containing compounds including pesticides, therapeutics, and dietary substances
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additional information
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flavin-containing monooxygenases catalyze the addition of oxygen to many sulfur-, nitrogen-, phosphorus-, and selenium-containing compounds including pesticides, therapeutics, and dietary substances
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additional information
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flavin-containing monooxygenases catalyze the addition of oxygen to many sulfur-, nitrogen-, phosphorus-, and selenium-containing compounds including pesticides, therapeutics, and dietary substances
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additional information
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flavin-containing monooxygenases catalyze the addition of oxygen to many sulfur-, nitrogen-, phosphorus-, and selenium-containing compounds including pesticides, therapeutics, and dietary substances
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additional information
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flavin-containing monooxygenases catalyze the addition of oxygen to many sulfur-, nitrogen-, phosphorus-, and selenium-containing compounds including pesticides, therapeutics, and dietary substances
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additional information
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flavin-containing monooxygenases catalyze the addition of oxygen to many sulfur-, nitrogen-, phosphorus-, and selenium-containing compounds including pesticides, therapeutics, and dietary substances
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additional information
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flavin-containing monooxygenases catalyze the addition of oxygen to many sulfur-, nitrogen-, phosphorus-, and selenium-containing compounds including pesticides, therapeutics, and dietary substances
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additional information
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flavin-containing monooxygenases catalyze the addition of oxygen to many sulfur-, nitrogen-, phosphorus-, and selenium-containing compounds including pesticides, therapeutics, and dietary substances
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additional information
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flavin-containing monooxygenases catalyze the addition of oxygen to many sulfur-, nitrogen-, phosphorus-, and selenium-containing compounds including pesticides, therapeutics, and dietary substances
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additional information
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flavin-containing monooxygenases catalyze the addition of oxygen to many sulfur-, nitrogen-, phosphorus-, and selenium-containing compounds including pesticides, therapeutics, and dietary substances
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additional information
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flavin-containing monooxygenases catalyze the addition of oxygen to many sulfur-, nitrogen-, phosphorus-, and selenium-containing compounds including pesticides, therapeutics, and dietary substances
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additional information
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regulation of the enzyme expression by hypersaline conditions and the osmoregulatory hormonecortisol, overview
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additional information
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regulation of the enzyme expression by hypersaline conditions and the osmoregulatory hormonecortisol, overview
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additional information
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nitrogen- and sulfur-containing endogenous substrates and physiologic functions, the enzyme is involved in detoxification and drug metabolism, overview
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additional information
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the enzyme is involved in oxidative metabolism of drugs and other chemicals
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additional information
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the enzyme is involved in oxidative metabolism of drugs and other chemicals
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additional information
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benzydamine is a weak base and an indazole derivative with analgesic and antipyretic properties used in human and veterinary medicine, it is metabolized to a wide range of metabolites. One of the main metabolites, benzydamine N-oxide is produced in the liver and brain by flavin-containing monooxygenases
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additional information
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the enzyme is involved in detoxification, generally, metabolites produced by FMO-catalysed reactions are more hydrophilic and less toxic, and are easily excreted from the body
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additional information
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FMO oxygenates a number of drugs and xenobiotics containing a soft-nucleophile heteroatom, mostly sulfur- and nitrogen-containing xenobiotics, and is involved in detoxication
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additional information
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the enzyme plays an important role in drug metabolism, insulin itself has no effect on FMO1 activity in non-diabetic animals, but hepatic isozyme FMO1 and intestinal CYP3A activity are correlated with average blood glucose concentration in untreated diabetic rats, and insulin reduces CYP3A activity, thus also regulates FMO1 indirectly
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additional information
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the substrate specificity of Saccharomyces cerevisiae FMO is more restricted than that of mammalian FMOs, reflecting its role in maintaining redox balance in the cell
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additional information
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FMO oxygenates a number of drugs and xenobiotics containing a soft-nucleophile heteroatom, mostly sulfur- and nitrogen-containing xenobiotics, and is involved in detoxication
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additional information
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nitrogen- and sulfur-containing endogenous substrates and physiologic functions, the enzyme is involved in detoxification and drug metabolism, overview
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additional information
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benzydamine is a weak base and an indazole derivative with analgesic and antipyretic properties used in human and veterinary medicine, it is metabolized to a wide range of metabolites. One of the main metabolites, benzydamine N-oxide is produced in the liver and brain by flavin-containing monooxygenases
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A52T
naturally occuring mutation causing trimethylaminuria or fish-odor-syndrome
C530L
naturally occuring single nucleotide polymorphism of FMO2
D198E
naturally occuring mutation causing trimethylaminuria or fish-odor-syndrome
D227K
pKa value 7.3 for N-oxygenation of 10-(N,N-dimethylaminooctyl)2-(trifluoromethyl)phenothiazene, compared with 6.9 for wild-type
D36G
naturally occuring single nucleotide polymorphism of FMO2
down
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FMO5 is downregulated in type II diabetes in liver. FMO1 downregulation and inhibition by 3,3'-diindolylmethane
E132H
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natural genetic variant of isozyme FMO2, substrate specificity, overview
E132H/E158K
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natural genetic variant of isozyme FMO2, substrate specificity, overview
E158K/T201K/E308G
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naturally occuring genetic variant of isozyme FMO3, and site-directed mutagenesis, the mutant shows reduced activity with sulindac and methyl 4-toyl sulfide compared to the wild-type FMO3
E158K/V257M
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the naturally occuring polymorphisms reduce the oxidation and clearance of FMO3 substrates such as tyramine, and TMA in vitro, and mutations are highly likely to eliminate the enzyme function in vivo
E305X
naturally occuring mutation causing trimethylaminuria or fish-odor-syndrome
E314G
naturally occuring single nucleotide polymorphism of FMO2
E314X
naturally occuring mutation causing trimethylaminuria or fish-odor-syndrome
E32K
naturally occuring mutation causing trimethylaminuria or fish-odor-syndrome
E339Q
naturally occuring single nucleotide polymorphism of FMO4
E362Q
naturally occuring single nucleotide polymorphism of FMO3
F182S
naturally occuring single nucleotide polymorphism of FMO2
F510X
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natural genetic variant of isozyme FMO2, substrate specificity, overview
F69Y
naturally occuring single nucleotide polymorphism of FMO2
F81S
naturally occuring single nucleotide polymorphism of FMO2
G148X
naturally occuring mutation causing trimethylaminuria or fish-odor-syndrome
G180V
naturally occuring single nucleotide polymorphism of FMO3, the mutant is similar to the wild-type enzyme
G182E
pKa value 6.6 for N-oxygenation of 10-(N,N-dimethylaminooctyl)2-(trifluoromethyl)phenothiazene, compared with 6.9 for wild-type
G475D
naturally occuring mutation causing trimethylaminuria or fish-odor-syndrome
G503R
naturally occuring single nucleotide polymorphism of FMO3
H360P
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site-directed mutagenesis of isozyme FMO1, the mutant shows altered thermal stability and highly increased activity with mercaptoimidazole and chlorpromazine compared to the wild-type FMO1
I199T
naturally occuring mutation causing trimethylaminuria or fish-odor-syndrome
I468M
naturally occuring single nucleotide polymorphism of FMO3
K158L
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Km-value for fenthion is 1.4fold higher than the wild-type value, Vmax for fenthion is nearly identical to the wild-type value, mutant of FMO3
K158L/D132H
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Km-value for fenthion is 1.5fold higher than the wild-type value, Vmax for fenthion is 1.5fold higher than the wild-type value, mutant of FMO3
L360A
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site-directed mutagenesis of isozyme FMO3, the mutant shows altered thermal stability and reduced activity with mercaptoimidazole, chlorpromazine, and 10-[(N,N-dimethylaminopentyl)-2-(trifluoromethyl)]phenothiazine compared to the wild-type FMO3
L360H
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site-directed mutagenesis of isozyme FMO3, the mutant shows altered thermal stability and reduced activity with mercaptoimidazole, chlorpromazine, and 10-[(N,N-dimethylaminopentyl)-2-(trifluoromethyl)]phenothiazine compared to the wild-type FMO3
L360Q
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site-directed mutagenesis of isozyme FMO3, the mutant shows altered thermal stability and reduced activity with mercaptoimidazole, chlorpromazine, and 10-[(N,N-dimethylaminopentyl)-2-(trifluoromethyl)]phenothiazine compared to the wild-type FMO3
M260V
naturally occuring single nucleotide polymorphism of FMO3
M434I
naturally occuring mutation causing trimethylaminuria or fish-odor-syndrome
M82T
naturally occuring mutation causing trimethylaminuria or fish-odor-syndrome
N114S
naturally occuring mutation causing trimethylaminuria or fish-odor-syndrome
P457L
naturally occuring single nucleotide polymorphism of FMO4
Q170K
pKa value 6.6 for N-oxygenation of 10-(N,N-dimethylaminooctyl)2-(trifluoromethyl)phenothiazene, compared with 6.9 for wild-type
Q206H
pKa value 6.5 for N-oxygenation of 10-(N,N-dimethylaminooctyl)2-(trifluoromethyl)phenothiazene, compared with 6.9 for wild-type
Q470X
naturally occuring mutation causing trimethylaminuria or fish-odor-syndrome
R238P
naturally occuring mutation causing trimethylaminuria or fish-odor-syndrome
R238Q
naturally occuring single nucleotide polymorphism of FMO2
R249X
naturally occuring single nucleotide polymorphism of FMO2, probably inactive mutant
R378L
naturally occuring mutation causing trimethylaminuria or fish-odor-syndrome
R391T
naturally occuring single nucleotide polymorphism of FMO2
R492W
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naturally occuring mutation involved in trimethylaminuria, the mutant fails to incorporate/retain the FAD cofactor
R500X
naturally occuring mutation causing trimethylaminuria or fish-odor-syndrome
R502V
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no activity with methimazole, KM-value for methyl p-tolyl sulfide is 70% of the wild-type value, Vmax with methyl p-tolyl sulfide is 70% of the wild-type value, KM-value for imipramine is is nearly identical to the the wild-type value, Vmax with imipramine is 49% of the wild-type value, KM-value for fenthion is 88% of the wild-type value, Vmax with fenthion is 55% of wild-type value, mutant of FMO1
R506S
naturally occuring single nucleotide polymorphism of FMO4
R51G
naturally occuring mutation causing trimethylaminuria or fish-odor-syndrome
T201K
naturally occuring mutation causing trimethylaminuria or fish-odor-syndrome
T308S
naturally occuring single nucleotide polymorphism of FMO4
V143E
naturally occuring mutation causing trimethylaminuria or fish-odor-syndrome
V257M/E308G
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naturally occuring polymorphism, the substitutions do not affect enzyme activity in vitro
V257M/M260V
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naturally occuring genetic variant of isozyme FMO3, and site-directed mutagenesis, the mutant shows reduced activity with sulindac and methyl 4-toyl sulfide compared to the wild-type FMO3
V277A
naturally occuring single nucleotide polymorphism of FMO3
V323A
naturally occuring single nucleotide polymorphism of FMO4
V58I
naturally occuring mutation causing trimethylaminuria or fish-odor-syndrome
W388X
naturally occuring mutation causing trimethylaminuria or fish-odor-syndrome
Y228H
pKa value 7.9 for N-oxygenation of 10-(N,N-dimethylaminooctyl)2-(trifluoromethyl)phenothiazene, compared with 6.9 for wild-type
E158A/E159A
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the mutant shows similar activity with trimethylamine compared to the wild-type enzyme
Y207S
mutant exhibits very little indoxyl producing activity but the NADPH oxidase activity of the mutant is higher than that of the wild-type enzyme
E158A/E159A
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the mutant shows similar activity with trimethylamine compared to the wild-type enzyme
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Y207S
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mutant exhibits very little indoxyl producing activity but the NADPH oxidase activity of the mutant is higher than that of the wild-type enzyme
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C78A
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site-directed mutagenesis, the mutation leads to an increase in KM and kcat compared to wild-type enzyme, but the mutant shows reduced activity compared to wild-type enzyme
C78I
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site-directed mutagenesis, the mutation leads to an increase in KM and kcat compared to wild-type enzyme, but the mutant shows reduced activity compared to wild-type enzyme
C78L
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site-directed mutagenesis, the mutant shows reduced activity compared to wild-type enzyme
C78V
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site-directed mutagenesis, the mutation leads to an increase in KM and kcat compared to wild-type enzyme, but the mutant shows reduced activity compared to wild-type enzyme
M15L/S23A
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site-directed mutagenesis, combining the two mutations at the N-terminus results in a 3°C increase in apparent melting temperature. Both M15L and S23A are far from the active site and no significant effect on the kinetic parameters of the enzyme is observed. Adding more stabilizing mutations does not contribute to a higher thermostability
W319A
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site-directed mutagenesis, the mutant shows reduced activity compared to wild-type enzyme
W319F
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site-directed mutagenesis, the mutant shows reduced activity compared to wild-type enzyme
W47A
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insoluble inactive protein
W47F
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soluble and active protein. The spectrum of the flavin displays a redshift, the kcat values for NADPH, trimethylamine, and methimazole, show a 5-8fold decrease, and primary kinetic isotope effect values are higher than in wild-type. Mutant displays reduced flexibility in active site residues and, in particular, the nicotinamide moiety of NADP+
Y207W/W319A
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site-directed mutagenesis, the mutant shows reduced activity compared to wild-type enzyme
W47A
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insoluble inactive protein
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W47F
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soluble and active protein. The spectrum of the flavin displays a redshift, the kcat values for NADPH, trimethylamine, and methimazole, show a 5-8fold decrease, and primary kinetic isotope effect values are higher than in wild-type. Mutant displays reduced flexibility in active site residues and, in particular, the nicotinamide moiety of NADP+
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H228Y
pKa value 6.6 for N-oxygenation of 10-(N,N-dimethylaminooctyl)2-(trifluoromethyl)phenothiazene, compared with 7.7 for wild-type
K227D
pKa value 6.6 for N-oxygenation of 10-(N,N-dimethylaminooctyl)2-(trifluoromethyl)phenothiazene, compared with 7.7 for wild-type
D132H
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KM-value and Vmax of fenthion are nearly identical to the wild-type values, mutant of FMO3
D132H
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natural genetic variant of isozyme FMO2, substrate specificity, overview
D132H
naturally occuring single nucleotide polymorphism of FMO3, the mutant shows substrate-dependent reduced activity
E158K
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major naturally occuring structural varainat of isozyme FMO3, the mutant shows increased activity with tamoxifen compared to the wild-type enzyme
E158K
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natural genetic variant of isozymes FMO2 and FMO3, substrate specificity, overview
E158K
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naturally occuring genetic variant of isozyme FMO3, and site-directed mutagenesis, the mutant shows reduced activity with sulindac and methyl 4-toyl sulfide compared to the wild-type FMO3
E158K
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naturally occuring polymorphism of FMO3, frequency in different human populations, the mutation has an impact on protein structure, overview
E158K
loss of function mutation of FMO3 results in trimethylaminuria or fish-odor-syndrome, the mutant enzyme is incapable of metabolizing trimethylamine to its non-odorous N-oxide, phenotype, overview
E158K
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naturally occuring mutation not involved in primary trimethylaminuria
E158K
naturally occuring single nucleotide polymorphism of FMO3 in Europeans and Asians, the mutation slightly affects enzyme activity, substrate-dependent reduced activity, phenotype, overview
E158K
naturally occuring single nucleotide polymorphism of FMO3, the mutation slightly affects enzyme activity, substrate-dependent reduced activity
E158K
the mutant shows moderately reduced activity
E158K
naturally occuring mutation and site-directed mutagenesis, the mutant exhibits a significant increase in all the kinetic parameters measured with substrate tamoxifen with nearly two times faster clearance. The mutation has no effect on the clearance of GSK5182
E158K
naturally occuring polymorphic variant and site-directed mutagenesis, the melting temperature and activation energy of the mutant is nearly unaltered compared to the wild-type enzyme
E158K
naturally occuring polymorphism of FMO3, the E158K variant is mostly expressed in African-American and Europeans, the mutant shows reduced activity compared to the wild-type enzyme
E158K/E308G
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natural genetic variant of isozyme FMO2, substrate specificity, overview
E158K/E308G
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naturally occuring genetic variant of isozyme FMO3, and site-directed mutagenesis, the mutant shows reduced activity with sulindac and methyl 4-toyl sulfide compared to the wild-type FMO3
E158K/E308G
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naturally occuring polymorphism, in many cases in vivo, altered clinical responses or altered susceptibility to various chemicals due to these sequence variants are observed compared to the carriers of at least one wild-type allele
E158K/E308G
-
naturally occuring mutation not involved in primary trimethylaminuria
E158K/E308G
naturally occuring single nucleotide polymorphism of FMO3 in Europeans and Asians, the mutation affects enzyme activity, substrate-dependent reduced activity, phenotype, overview
E158K/E308G
naturally occuring single nucleotide polymorphism of FMO3, the mutation affects enzyme activity, substrate-dependent reduced activity
E24D
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naturally occuring polymorphism of FMO3, frequency in different human populations, the mutation has an impact on protein structure, overview, the mutant shows altered substrate specificity compared to the wild-type mutant
E24D
naturally occuring single nucleotide polymorphism of FMO3, the mutant shows reduced activity
E308G
-
natural genetic variant of isozyme FMO2, substrate specificity, overview
E308G
-
naturally occuring polymorphism of FMO3, frequency in different human populations, the mutation has an impact on protein structure, overview
E308G
loss of function mutation of FMO3 results in trimethylaminuria or fish-odor-syndrome, the mutant enzyme is incapable of metabolizing trimethylamine to its non-odorous N-oxide, phenotype, overview
E308G
-
naturally occuring mutation not involved in primary trimethylaminuria
E308G
naturally occuring single nucleotide polymorphism of FMO3 in Europeans and Asians, the mutation slightly affects enzyme activity, substrate-dependent reduced activity, phenotype, overview
E308G
naturally occuring single nucleotide polymorphism of FMO3, the mutation slightly affects enzyme activity, substrate-dependent reduced activity
E308G
the mutant shows moderately reduced activity
E308G
naturally occuring mutation and site-directed mutagenesis, the mutant exhibits a significant increase in all the kinetic parameters measured with substrate clomiphene with nearly two times faster clearance. The mutation has no effect on the clearance of GSK5182
E308G
naturally occuring polymorphic variant and site-directed mutagenesis, the mutant is unable to bind the NADP+ cofactor, it shows a significantly higher energy of unfolding (Ea) compared to wild-type
E308G
naturally occuring polymorphism of FMO3, the E308G is widely distributed in Asians and Europeans, the mutant shows reduced activity compared to the wild-type enzyme
H97Q
-
KM-value for methimazole is 3fold higher than wild-type value, Vmax with methimazole is 1.6fold higher than the wild-type value, KM-value for methyl p-tolyl sulfide is 88% of the wild-type value, Vmax with methyl p-tolyl sulfide is 1.4fold higher than the wild-type value, KM-value for imipramine is is nearly identical to the the wild-type value, Vmax with imipramine is 1.3fold higher than the wild-type value, KM-value for fenthion is 94% of the wild-type value, Vmax with fenthion is 1.3fold higher than the wild-type value, mutant of FMO1
H97Q
-
natural genetic variant of isozyme FMO1, substrate specificity, overview
H97Q
naturally occuring single nucleotide polymorphism of FMO1, the mutant enzyme is similar to the wild-type enzyme
I303T
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KM-value for methimazole is 2.3fold higher than wild-type value, Vmax with methimazole is 1.8fold higher than the wild-type value, KM-value for methyl p-tolyl sulfide is 86% of the wild-type value, Vmax with methyl p-tolyl sulfide is 1.8fold higher than the wild-type value, KM-value for imipramine is identical to the the wild-type value, Vmax with imipramine is 1.4fold higher than the wild-type value, KM-value for fenthion is 94% of the wild-type value, Vmax with fenthion is 1.6fold higher than the wild-type value, mutant of FMO1
I303T
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natural genetic variant of isozyme FMO1, substrate specificity, overview
I303T
naturally occuring single nucleotide polymorphism of FMO1, the mutant enzyme is similar to the wild-type enzyme
I303V
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KM-value for methimazole is identical to the wild-type value, Vmax with methimazole is nearly identical to the wild-type value, KM-value and Vmax for meth is 1,4fold higher than the the wild-type value, Vmax with imipramine is nearly identical to the wild-type value, KM-value and Vmax for fenthion are nearly identical to the wild-type values, mutant of FMO1
I303V
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natural genetic variant of isozyme FMO1, substrate specificity, overview
I303V
naturally occuring single nucleotide polymorphism of FMO1, the mutant enzyme is similar to the wild-type enzyme
I37T
naturally occuring mutation causing trimethylaminuria or fish-odor-syndrome
I37T
naturally occuring single nucleotide polymorphism of FMO4
K416N
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naturally occuring polymorphism of FMO3, frequency in different human populations, the mutation has an impact on protein structure, overview, the mutant shows altered substrate specificity compared to the wild-type mutant
K416N
naturally occuring single nucleotide polymorphism of FMO3, the mutant shows reduced activity
L360P
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natural genetic variant of isozyme FMO2, substrate specificity, overview
L360P
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site-directed mutagenesis of isozyme FMO3, the mutant shows altered thermal stability and increased activity with mercaptoimidazole, chlorpromazine, and 10-[(N,N-dimethylaminopentyl)-2-(trifluoromethyl)]phenothiazine compared to the wild-type FMO3
L360P
naturally occuring single nucleotide polymorphism of FMO3, the mutant shows increased activity
L360P
naturally occuring single nucleotide polymorphism of FMO3, the mutant shows increased activity
L360P
the mutation increases catalytic activity
M66I
naturally occuring mutation causing trimethylaminuria or fish-odor-syndrome
M66I
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naturally occuring mutation involved in trimethylaminuria, the mutant fails to incorporate/retain the FAD cofactor
N413K
naturally occuring single nucleotide polymorphism of FMO2, the mutant is similar to the wild-type enzyme
N413K
naturally occuring mutant of the FMO2*1 allele, the mutant shows higher kcat and Vmax, and increased thermosensitivity compared to the wild-type enzyme, activity is stabilized by NADPH
N413K
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the mutant of isoform FMO2 exhibits higher catalytic activity toward methyl-4-tolyl sulfide compared to the wild type enzyme
N61K
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naturally occuring polymorphism of FMO3, frequency in different human populations, the mutation has an impact on protein structure, overview, the mutant shows altered substrate specificity compared to the wild-type mutant
N61K
naturally occuring single nucleotide polymorphism of FMO3, the mutant shows reduced activity
N61K
naturally occuring single nucleotide polymorphism of FMO3, the mutant shows reduced activity
N61S
loss of function mutation of FMO3 results in trimethylaminuria or fish-odor-syndrome, the mutant enzyme is incapable of metabolizing trimethylamine to its non-odorous N-oxide, nuta this mutant is still active with methimazole, phenotype, overview
N61S
loss of function mutation of FMO3 results in trimethylaminuria or fish-odor-syndrome, the mutant enzyme is incapable of metabolizing trimethylamine to its non-odorous N-oxide, nuta this mutant is still active with methimazole, phenotype, overview
N61S
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naturally occuring mutation involved in trimethylaminuria, the mutant shows over 90% reduced activity with trimethylamine compared to the wild-type enzyme
N61S
an active site polymorphic variant, the single-nucleotide polymorphism is leading to deleterious effects of oxidative stress. N-Oxygenation of benzydamine by the wild-type and N61S mutant variant of FMO3. In the absence of the substrate benzydamine (BZD), N61S produces higher amounts of H2O2 compared to wild-type
P153L
loss of function mutation of FMO3 results in trimethylaminuria or fish-odor-syndrome, the mutant enzyme is incapable of metabolizing trimethylamine to its non-odorous N-oxide, phenotype, overview
P153L
naturally occuring mutation causing trimethylaminuria or fish-odor-syndrome
P153L
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naturally occuring mutation involved in trimethylaminuria, the mutant shows over 90% reduced activity with trimethylamine compared to the wild-type enzyme
Q472X
naturally occuring single nucleotide polymorphism of FMO2, inactive mutant
Q472X
naturally occuring single nucleotide polymorphism of FMO2, inactive mutant
Q472X
naturally occuring mutant of the FMO2*1 allele, more frequent in the sub-Sahara African population
R205C
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naturally occuring genetic variant of isozyme FMO3, and site-directed mutagenesis, the mutant shows reduced activity with sulindac and methyl 4-toyl sulfide compared to the wild-type FMO3, and is almost substrate inhibited, wild-type FMO3 has no free cysteine residues in the native form
R205C
loss of function mutation of FMO3 results in trimethylaminuria or fish-odor-syndrome, the mutant enzyme is incapable of metabolizing trimethylamine to its non-odorous N-oxide, phenotype, overview
R205C
naturally occuring single nucleotide polymorphism of FMO3, the mutant shows highly reduced activity
R205C
naturally occuring single nucleotide polymorphism of FMO3, the mutant shows reduced activity
R223Q
naturally occuring mutation causing trimethylaminuria or fish-odor-syndrome
R223Q
naturally occuring single nucleotide polymorphism of FMO1
R502X
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natural genetic variant of isozyme FMO1, substrate specificity, overview
R502X
naturally occuring single nucleotide polymorphism of FMO1, the mutant shows substrate-dependent reduced activity compared to the wild-type enzyme
R502X
naturally occuring single nucleotide polymorphism of FMO1, the mutant shows substrate-dependent reduced activity compared to the wild-type enzyme
S195L
naturally occuring single nucleotide polymorphism of FMO2, inactive mutant
S195L
naturally occuring mutant of the FMO2*1 allele, the mutant shows reduced activity and increased pH sensitivity and thermosensitivity compared to the wild-type enzyme, activity is stabilized by NADPH
S195L
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the mutant of isoform FMO2 exhibits lower catalytic activity toward methyl-4-tolyl sulfide and ethylene thiourea compared to the wild type enzyme
V257M
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variant with 13.21% allele frequency. Mutation causes a transformation of the secondary structure. The presence of this mutant allele correlates significantly with a reduction in caffeine N-1-demethylating activity
V257M
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natural genetic variant of isozyme FMO3, substrate specificity, overview
V257M
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naturally occuring genetic variant of isozyme FMO3, and site-directed mutagenesis, the mutant shows reduced activity with sulindac and methyl 4-toyl sulfide compared to the wild-type FMO3
V257M
loss of function mutation of FMO3 results in trimethylaminuria or fish-odor-syndrome, the mutant enzyme is incapable of metabolizing trimethylamine to its non-odorous N-oxide, phenotype, overview
V257M
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naturally occuring mutation not involved in primary trimethylaminuria
V257M
naturally occuring single nucleotide polymorphism of FMO3, the mutant shows slightly reduced activity
V257M
naturally occuring mutation and site-directed mutagenesis, residue V257 is not in the immediate vicinity of the active site and is part of the hFMO3 insert region in a loop that protrudes from the NADP+-binding domain across the FAD-binding domain, the mutant exhibits a significant increase in all the kinetic parameters measured with substrate clomiphene with nearly two times faster clearance, while the clearance with substrate tamoxifen is reduced. The mutation has no effect on the clearance of GSK5182
V257M
naturally occuring polymorphic variant and site-directed mutagenesis, the melting temperature and activation energy of the mutant is nearly unaltered compared to the wild-type enzyme
V257M
naturally occuring polymorphism of FMO3, the V257M polymorphic variant is predominantly present in Asians, the mutant shows reduced activity compared to the wild-type enzyme
Y207W
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site-directed mutagenesis, the mutant shows reduced activity compared to wild-type enzyme
Y207W
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site-directed mutagenesis, the mutation leads to an increase in KM and kcat, as well as in catalytic efficiency, compared to wild-type enzyme
additional information
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an Arabidopsis FMO1 knockout line is fully impaired in the establishment of systemic acquired resistance, SAR, triggered by virulent bacteria, loss of SAR in the FMO1 mutants is accompanied by the inability to initiate systemic accumulation of salicylic acid and systemic expression of diverse defense related genes, overview, fmo1mutation does not significantly affect local disease resistance toward virulent or avirulent bacteria in native plants
additional information
construction of fmo1 defective mutants, FMO1 mutations specifically affects the EDS1 pathway, defects in Arabidopsis fmo1 mutants are not coupled to SA accumulation, reduced pathogen defense, phenotype, analysis of fmo1 and nudt7 mutants alone or in combination with sid2-1, a mutation that severely depletes pathogen-induced salicylic acid production, points to salicylic acid-independent functions of FMO1 and NUDT7 in EDS1-conditioned disease resistance and cell death, overview
additional information
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construction of fmo1 defective mutants, FMO1 mutations specifically affects the EDS1 pathway, defects in Arabidopsis fmo1 mutants are not coupled to SA accumulation, reduced pathogen defense, phenotype, analysis of fmo1 and nudt7 mutants alone or in combination with sid2-1, a mutation that severely depletes pathogen-induced salicylic acid production, points to salicylic acid-independent functions of FMO1 and NUDT7 in EDS1-conditioned disease resistance and cell death, overview
additional information
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isolation of a dominant, gain-of-function phenotype FMO1-3D mutant, insertion at At1g19260 and towards the At1g19250 locus, from Arabidopsis thaliana, using activation tagging in the Arabidopsis Col-0 rps2-101C background, the mutant shows virtually no symptoms after inoculation with virulent Pseudomonas syringae pv. tomato DC3000 bacteria and downy mildew-causing pathogen Hyaloperonospora parasitica due to overexpression of class 3 FMO, overview, overexpression of the FMO1 cDNA, under control of the 35S CaMV promoter in independent transgenic Col-0 lines, leads to the same phenotype, progeny from crosses of the FMO1-3D mutant with the NahG transgenic line show that the enhanced basal resistance phenotype is dependent on the accumulation of salicylic acid, the R-gene-mediated defence physiology is not compromised by FMO1 overexpression, T-DNA insertion into the FMO1 gene resulted in enhances the susceptibility to virulent Pseudomonas and Hyaloperonospora parasitica, phenotypes, overview
additional information
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determination and analysis of frequencies of 18 FMO3 single-nucleotide polymorphisms in 202 Hispanics of Mexican descent, 201 African Americans, and 200 non-Latino whites, synonymous mutations, and hypomorphic haplotypes, overview
additional information
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effects of genetic variants of isozyme FMO3 on N- and S-oxygenation activities, genotype-phenotype studies, overview
additional information
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identification and analysis of 18 mutations of FMO3 genes from 134 AfricanAmericans and 129 Caucasians from the United States, missense and nonsense nucleotide substitutions, and polymorphic variants of the gene, both involved in development of trimethylaminuria, TMAU, interindividual variability in the expression of FMO3 may affect drug and exogenous chemical metabolism in the liver and other tissues, clinical relevance of the polymorphisms, overview
additional information
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occuring single nucleotide polymorphisms are associated with dramatic functional differences in selective functional enzyme activity, overview
additional information
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three of the five expressed human FMO genes, FMO1, FMO2 and FMO3, exhibit genetic polymorphisms, overview
additional information
FMO3 is highly polymorphic, with as many as 15 nonsynonymous single nucleotide polymorphisms identified, many of which are present at relatively high frequency, several single nucleotide polymorphisms cause loss of function mutation of FMO3 resulting in trimethylaminuria or fish-odor-syndrome, the mutant enzymes are incapable of metabolizing trimethylamine to its non-odorous N-oxide, haplotypes and phenotypes, overview
additional information
FMO3 is highly polymorphic, with as many as 15 nonsynonymous single nucleotide polymorphisms identified, many of which are present at relatively high frequency, several single nucleotide polymorphisms cause loss of function mutation of FMO3 resulting in trimethylaminuria or fish-odor-syndrome, the mutant enzymes are incapable of metabolizing trimethylamine to its non-odorous N-oxide, haplotypes and phenotypes, overview
additional information
FMO3 is highly polymorphic, with as many as 15 nonsynonymous single nucleotide polymorphisms identified, many of which are present at relatively high frequency, several single nucleotide polymorphisms cause loss of function mutation of FMO3 resulting in trimethylaminuria or fish-odor-syndrome, the mutant enzymes are incapable of metabolizing trimethylamine to its non-odorous N-oxide, haplotypes and phenotypes, overview
additional information
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FMO3 is highly polymorphic, with as many as 15 nonsynonymous single nucleotide polymorphisms identified, many of which are present at relatively high frequency, several single nucleotide polymorphisms cause loss of function mutation of FMO3 resulting in trimethylaminuria or fish-odor-syndrome, the mutant enzymes are incapable of metabolizing trimethylamine to its non-odorous N-oxide, haplotypes and phenotypes, overview
additional information
genotyping of FMO3 in a Japanese cohort, missense and nonsense mutations, overview
additional information
most humans are homozygous for a nonsense mutation that inactivates FMO2. But a substantial proportion of sub-Saharan Africans express functional FMO2 and, thus, are predicted to respond differently to drugs and other foreign chemicals
additional information
most humans are homozygous for a nonsense mutation that inactivates FMO2. But a substantial proportion of sub-Saharan Africans express functional FMO2 and, thus, are predicted to respond differently to drugs and other foreign chemicals
additional information
most humans are homozygous for a nonsense mutation that inactivates FMO2. But a substantial proportion of sub-Saharan Africans express functional FMO2 and, thus, are predicted to respond differently to drugs and other foreign chemicals
additional information
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most humans are homozygous for a nonsense mutation that inactivates FMO2. But a substantial proportion of sub-Saharan Africans express functional FMO2 and, thus, are predicted to respond differently to drugs and other foreign chemicals
additional information
naturally occuring mutations, including silent mutations, genotyping, overview
additional information
naturally occuring mutations, including silent mutations, genotyping, overview
additional information
naturally occuring mutations, including silent mutations, genotyping, overview
additional information
naturally occuring mutations, including silent mutations, genotyping, overview
additional information
naturally occuring mutations, including silent mutations, genotyping, overview
additional information
several single nucleotide polymorphisms cause loss of function mutation of FMO3 resulting in trimethylaminuria or fish-odor-syndrome, the mutant enzymes are incapable of metabolizing trimethylamine to its non-odorous N-oxide, haplotypes and phenotypes, overview
additional information
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several single nucleotide polymorphisms cause loss of function mutation of FMO3 resulting in trimethylaminuria or fish-odor-syndrome, the mutant enzymes are incapable of metabolizing trimethylamine to its non-odorous N-oxide, haplotypes and phenotypes, overview
additional information
the HepG2 model is suitable for the study of FMO3 regulation, deletion analysis of FMO3/luciferase reporter constructs, domains A-I, and specific transcription factor responsive elements identified by DNA-protein binding reactions and site-directed mutagenesis of FMO3 reporter constructs, functional analysis of the FMO3 HNF3, and C/EBP elements, FMO3 promoter analysis, overview
additional information
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the HepG2 model is suitable for the study of FMO3 regulation, deletion analysis of FMO3/luciferase reporter constructs, domains A-I, and specific transcription factor responsive elements identified by DNA-protein binding reactions and site-directed mutagenesis of FMO3 reporter constructs, functional analysis of the FMO3 HNF3, and C/EBP elements, FMO3 promoter analysis, overview
additional information
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enzyme activity analysis using a simple but functional and stable enzyme-electrode system based on a glassy carbon electrode with human flavin-containing monooxygenase isoform 3 entrapped in a gel cross-linked with bovine serum albumin by glutaraldehyde, method development and evaluation, overview
additional information
generation of humanized-liver TK-NOG mice, chimeric mice, in which more than 90% of liver cells are estimated to have been replaced with human hepatocytes, interactions between FMO substrates in humanized-liver mice, overview. Administered itopride (10 mg/kg) is extensively oxygenated to its N-oxide in humanized-liver mouse plasma. The area under the concentration-time curve of itopride N-oxide is 15fold that of itopride in humanize-liver mice
additional information
generation of truncated forms of wild-type and mutant enzymes, the 17 amino acid truncation at the C-terminal of FMO3 results in a more soluble protein, the truncated enzymes are better catalysts than the full-length proteins. The truncated enzymes are not only fully active, but also have a higher vmax compared to their full-length counterparts, the latter observation might be the result of their higher solubility. The mutations have no major effect on the interaction of the FAD cofactor with the protein
additional information
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generation of truncated forms of wild-type and mutant enzymes, the 17 amino acid truncation at the C-terminal of FMO3 results in a more soluble protein, the truncated enzymes are better catalysts than the full-length proteins. The truncated enzymes are not only fully active, but also have a higher vmax compared to their full-length counterparts, the latter observation might be the result of their higher solubility. The mutations have no major effect on the interaction of the FAD cofactor with the protein
additional information
unfolding process of a phase I drug metabolizing enzyme, human flavin-containing monooxygenase 3 (hFMO3) and its single nucleotide polymorphic variants (SNPs) V257M, E158K and E308G are analyzed by differential scanning calorimetry (DSC) indicating that the thermal denaturation of the enzyme is irreversible. The melting temperature (Tm) for the wild-type enzyme and its polymorphic variants is in a range from 46°C to 50°C. Also the activation energies of unfolding (Ea) show no significant differences among all proteins investigated (290-328 KJ/mol), except for the E308G variant that shows a significantly higher Ea of 412 KJ/mol. The presence of the bound NADP+ cofactor stabilizes all the variants by shifting the main Tm by 4-5°C for all the proteins, exception made for E308G where no changes are observed
additional information
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unfolding process of a phase I drug metabolizing enzyme, human flavin-containing monooxygenase 3 (hFMO3) and its single nucleotide polymorphic variants (SNPs) V257M, E158K and E308G are analyzed by differential scanning calorimetry (DSC) indicating that the thermal denaturation of the enzyme is irreversible. The melting temperature (Tm) for the wild-type enzyme and its polymorphic variants is in a range from 46°C to 50°C. Also the activation energies of unfolding (Ea) show no significant differences among all proteins investigated (290-328 KJ/mol), except for the E308G variant that shows a significantly higher Ea of 412 KJ/mol. The presence of the bound NADP+ cofactor stabilizes all the variants by shifting the main Tm by 4-5°C for all the proteins, exception made for E308G where no changes are observed
additional information
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preparation of self-sufficient monooxygenases by covalent coupling of mFMO with the soluble NADPHregenerating phosphite dehydrogenase, PTDH, from Pseudomonas stutzeri using a codon-optimized gene encoding a His-tagged and thermostable PTDH mutant as fusion partner. The bifunctional biocatalyst is able to use phosphite as a cheap and sacrificial substrate for recycling NADPH
additional information
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preparation of self-sufficient monooxygenases by covalent coupling of mFMO with the soluble NADPHregenerating phosphite dehydrogenase, PTDH, from Pseudomonas stutzeri using a codon-optimized gene encoding a His-tagged and thermostable PTDH mutant as fusion partner. The bifunctional biocatalyst is able to use phosphite as a cheap and sacrificial substrate for recycling NADPH
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additional information
construction of Fmo1-/-, 2-/-, and 4-/- knockout mutants, 1D 1H NMR spectroscopy to compare the urinary metabolite profiles of the knockout-mouse line and wild-type animals, metabolic profiles of hypotaurine and taurine in wild-type and mutant mice' urine samples, overview
additional information
C-terminal truncation of 26 amino acids and and a double Ser substitutio of isozyme FMO2 enhances the enzyme solubility and reduce hydrophobicity required for efficient enzyme crystallization, overview
additional information
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C-terminal truncation of 26 amino acids and and a double Ser substitutio of isozyme FMO2 enhances the enzyme solubility and reduce hydrophobicity required for efficient enzyme crystallization, overview
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