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(S)-1-indanol + NADP+
?
-
-
-
-
?
(S)-1-tetralol + NADP+
?
-
-
-
-
?
(S)-methyl 3-hydroxybutyrate + NADP+
methyl acetoacetate + NADPH + H+
(S)-tetralol + NAD(P)+
3,4-dihydronaphthalen-1(2H)-one + NAD(P)H + H+
-
-
-
?
1,2-cyclohexanedione + NADP+
?
1,2-cyclohexanedione + NADPH + H+
?
-
-
-
-
r
1-acenaphthenol + NAD+
? + NADH + H+
-
-
-
?
1-phenyl-1,2-propanedione + NADPH
NADP+ + ?
11-deoxycorticosterone + NAD(P)H
4-pregnen-20alpha,21-diol-3-one + NAD(P)+
11-deoxycortisol + NADH
? + NAD+
11-deoxycortisol + NADH + H+
? + NAD+
17alpha,20alpha-dihydroxypregn-4-en-3-one + NAD(P)+
17alpha-hydroxyprogesterone + NAD(P)H
17alpha,21-dihydroxy-5beta-pregnan-3,20-dione + NADPH + H+
17alpha,20alpha,21-trihydroxy-5beta-pregnane-3-one + NADP+
-
-
-
-
r
17alpha,21-dihydroxy-5beta-pregnane-3,11,20-trione + NADPH + H+
17alpha,20alpha,21-trihydroxy-5beta-pregnane-3,11-dione + NADP+
-
-
-
-
r
17alpha,21-dihydroxyadrenocorticosteroid + NAD(P)H
? + NADP+
-
NADH preferred
-
?
17alpha-hydroxy-progesterone + NADH + H+
17alpha,20alpha-dihydroxypregn-4-en-3-one + NAD+
-
-
-
-
r
17alpha-hydroxycorticosterone + NADPH
? + NADP+
-
less reactive than with 17alpha-hydroxyrogesterone
-
?
17alpha-hydroxypregnenolone + NADPH
? + NADP+
17alpha-hydroxyprogesterone + NAD(P)H
17alpha,20alpha-dihydroxypregn-4-en-3-one + NAD(P)+
17alpha-hydroxyprogesterone + NAD(P)H + H+
17alpha,20alpha-dihydroxy-pregn-4-en-3-one + NAD(P)+
17alpha-hydroxyprogesterone + NADPH
17alpha,20alpha-dihydroxyprogesterone + NADP+
17alpha-hydroxyprogesterone + NADPH + H+
17alpha,20alpha-dihydroxy-pregn-4-en-3-one + NADP+
17beta-estradiol + NADP+
?
-
-
-
-
?
2,3-butanedione + NADPH
? + NADP+
2,3-heptanedione + NADPH
NADP+ + ?
2,3-hexanedione + NADPH
NADP+ + ?
2,3-pentanedione + NADPH
NADP+ + ?
2,4-pentanedione + NADP+
?
2,4-pentanedione + NADPH + H+
4-hydroxypentan-2-one + NADP+
-
-
-
-
r
2-amino-8-((2-fluoro-4-methoxybenzyl)thio)-1,9-dihydro-6H-purin-6-one + NADP+
?
-
-
-
-
r
2-tert-butyl-1,4-benzoquinone + NADPH + H+
?
-
-
-
-
?
20alpha-dihydroprogesterone + NAD+
progesterone + NADH
-
-
-
?
20alpha-dihydroprogesterone + NADP+
progesterone + NADPH
-
-
-
?
20alpha-hydroxy-5alpha-pregnan-3-one + NADPH + H+
5alpha-pregnan-20alpha,3alpha-diol + NADP+
-
-
-
-
r
20alpha-hydroxy-5beta-pregnan-3-one + NADP+
5beta-pregnane-3,20-dione + NADPH
-
-
-
?
20alpha-hydroxypregn-4-en-3-one + 3-acetylpyridine adenine dinucleotide phosphate
?
-
-
-
-
r
20alpha-hydroxypregn-4-en-3-one + nicotinamide 1,N6-ethenoadenine dinucleotide phosphate
?
-
-
-
-
r
20alpha-hydroxypregn-4-en-3-one + nicotinamide hypoxanthine dinucleotide phosphate
?
-
-
-
-
r
20alpha-hydroxypregn-4-en-3-one + thionicotinamide adenine dinucleotide phosphate
?
-
-
-
-
r
20alpha-hydroxyprogesterone + NAD+
progesterone + NADH
-
-
-
-
?
20alpha-hydroxyprogesterone + NADP+
?
-
-
-
-
?
20alpha-hydroxyprogesterone + NADP+
progesterone + NADPH
3,4-hexanedione + NADP+
?
3-deoxyglucosone + NADPH + H+
?
-
-
-
-
?
3alpha-hydroxy-5-alpha-pregnan-20-one + NADPH + H+
5alpha-pregnan-3alpha,20alpha-diol + NADP+
-
-
-
-
r
3alpha-hydroxy-5alpha-pregnan-20-one + NADPH + H+
5alpha-pregnan-3alpha,20alpha-diol + NADP+
-
-
-
-
r
4-androstene-3,17-dione + NADPH + H+
?
-
-
-
-
?
4-chromanol + NADP+
?
-
-
-
-
?
4-hydroxy-2-nonenal + NADPH + H+
?
-
-
-
-
?
4-nitroacetophenone + NADPH + H+
?
-
-
-
-
?
4-nitrobenzaldehyde + NADPH
4-nitrobenzyl alcohol + NADP+
4-oxo-2-hexenal + NADPH + H+
?
-
-
-
-
?
4-oxo-2-nonenal + NADPH + H+
?
-
-
-
-
?
4-pregnen-20alpha-ol-3-one + NAD(P)+
4-pregnen-3,20-dione + NAD(P)H + H+
-
-
-
-
r
4-pregnen-3alpha-ol-20-one + NADPH + H+
?
-
-
-
-
?
5-androstene-3beta,17beta-diol + NADP+
?
-
-
-
-
?
5alpha-androstan-3alpha,17beta-diol + NADP+
?
-
-
-
-
?
5alpha-androstan-3alpha-ol-17-one + NADPH + H+
?
-
-
-
-
?
5alpha-androstan-3beta,17beta-diol + NADP+
?
-
-
-
-
?
5alpha-androstan-3beta-ol-17-one + NADPH + H+
?
-
-
-
-
?
5alpha-dihydroprogesterone + NADPH + H+
5alpha,20alpha-tetrahydroprogesterone + NADP+
5alpha-dihydrotestosterone + NADP+
?
-
-
-
-
?
5alpha-dihydrotestosterone + NADPH + H+
?
-
-
-
-
?
5alpha-dihydrotestosterone + NADPH + H+
? + NADP+
-
-
-
-
?
5alpha-pregnan-20alpha-ol-3-one + NAD(P)+
5alpha-pregnan-3,20-dione + NAD(P)H
-
-
-
-
r
5alpha-pregnan-20alpha-ol-3-one + NAD(P)+
5alpha-pregnane-3,20-dione + NAD(P)H
-
-
-
-
r
5alpha-pregnan-20alpha-ol-3-one + NADP+
5beta-pregnan-3,20-dione + NADPH + H+
-
-
-
-
r
5alpha-pregnan-20alpha-ol-3-one + NADP+
?
-
-
-
-
?
5alpha-pregnan-3,20-dione + NADPH + H+
?
-
-
-
-
?
5alpha-pregnan-3alpha,20alpha-diol + NADP+
?
-
-
-
-
?
5alpha-pregnan-3alpha,21-diol-20-one + NADPH + H+
?
-
-
-
-
?
5alpha-pregnan-3alpha-ol-20-one + NAD(P)H
5alpha-pregnan-3alpha,20alpha-diol + NAD(P)+
-
-
-
-
r
5alpha-pregnan-3alpha-ol-20-one + NAD(P)H + H+
5alpha-pregnan-3alpha,20alpha-diol + NAD(P)+
-
-
-
-
r
5alpha-pregnan-3alpha-ol-20-one + NADPH + H+
?
-
-
-
-
?
5alpha-pregnane-21-ol-3,20-dione + NAD(P)H
5alpha-pregnane-20alpha,21-diol-3-one + NAD(P)+
-
-
-
-
r
5alpha-pregnane-3,20-dione + NAD(P)H
5alpha-pregnan-20alpha-ol-3-one + NAD(P)+
-
-
-
-
r
5alpha-pregnane-3alpha,20alpha-diol + NAD(P)+
3alpha-hydroxy-5alpha-pregnan-20-one + NAD(P)H + H+
5alpha-pregnane-3alpha,21-diol-20-one + NAD(P)H + H+
5alpha-pregnane-3alpha,20alpha,21-triol + NAD(P)+
-
-
-
-
r
5beta-androstan-17beta-ol-3-one + NADP+
?
-
-
-
-
?
5beta-androstan-3alpha,17beta-diol + NADP+
?
-
-
-
-
?
5beta-androstan-3alpha-ol-17-one + NADPH + H+
?
-
-
-
-
?
5beta-androstan-3beta,17beta-diol + NADP+
?
-
-
-
-
?
5beta-androstan-3beta-ol-17-one + NADPH + H+
?
-
-
-
-
?
5beta-dihydrocortisol + NADH
? + NAD+
-
-
-
r
5beta-pregnan-20alpha-ol-3-one + NAD(P)+
5beta-pregnan-3,20-dione + NAD(P)H
-
-
-
-
r
5beta-pregnan-20alpha-ol-3-one + NADP+
?
5beta-pregnan-3,20-dione + NADPH + H+
5alpha-pregnan-20alpha-ol-3-one + NADP+
-
-
-
-
r
5beta-pregnan-3alpha,20alpha-diol + NADP+
?
-
-
-
-
?
5beta-pregnan-3alpha,21-diol-20-one + NADPH + H+
?
-
-
-
-
?
5beta-pregnan-3alpha-ol-20-one + NAD(P)H
5beta-pregnan-3alpha,20alpha-diol + NAD(P)+
-
-
-
-
r
5beta-pregnan-3alpha-ol-20-one + NAD(P)H
5beta-pregnane-3alpha,20alpha-diol + NAD(P)+
-
-
-
-
r
5beta-pregnan-3alpha-ol-20-one + NAD(P)H + H+
5alpha-pregnan-3alpha,20alpha-diol + NAD(P)+
-
-
-
?
5beta-pregnan-3alpha-ol-20-one + NADPH + H+
?
-
-
-
-
?
5beta-pregnane-3,20-dione + NAD(P)H + H+
5alpha-pregnan-20alpha-ol-3-one + NAD(P)+
-
-
-
-
r
5beta-pregnane-3alpha,20alpha-diol + NAD(P)+
5beta-pregnan-20alpha-ol-3-one + NAD(P)H + H+
6-tert-butyl-2,3-epoxy-5-cyclohexen-1,4-dione + NADPH + H+
?
-
-
-
-
?
7alpha-hydroxy-dehydroepiandrosterone + NADPH + H+
?
-
-
-
-
?
9,10-phenanthrenequinone + NADPH
NADP+ + ?
-
-
-
-
?
acetoacetyl-CoA + NADPH
NADP+ + ?
acrolein + NADPH + H+
?
-
-
-
-
?
all-trans-retinal + NADPH + H+
?
-
-
-
-
?
alpha-tetralone + NADPH + H+
?
-
-
-
-
?
befunolol + NADPH + H+
?
-
-
-
-
?
benzaldehyde + NADPH
benzyl alcohol + NADP+
-
-
-
-
?
benzene dihydrodiol + NADP+
2-hydroxycyclohexa-3,5-diene-1-one + NADPH + H+
-
-
-
-
r
benzyl acetoacetate + NADPH + H+
?
beta-ionol + NADP+
?
-
-
-
-
?
camphorquinone + NADP+
?
-
-
-
-
r
cis-benzene-1,2-dihydrodiol + NADP+
?
corticosterone + NADH + H+
? + NAD+
corticosterone + NADPH + H+
? + NADP+
-
less reactive than with 17alpha-hydroxyprogesterone
-
?
cortisol + NADH
20alpha-dihydrocortisol + NAD+
cortisol + NADH + H+
20beta-hydroxycortisol + NAD+
cortisone + NADH
? + NAD+
D-galactose + NADPH
NADP+ + ?
-
-
-
-
?
D-glucose + NADPH
NADP+ + ?
-
-
-
-
?
D-glyceraldehyde + NADPH + H+
glycerol + NADP+
D-lactaldehyde + NADPH + H+
?
daunorubicin + NADPH + H+
daunorubicinol + NADP+
dehydroepiandrosterone + NADPH + H+
?
-
-
-
-
?
dehydroepiandrosterone 3-sulfate + NADPH + H+
?
-
-
-
-
?
diacetyl + NADPH + H+
?
-
-
-
-
?
dihydrotestosterone + NADPH
? + NADP+
-
-
-
-
r
dihydrotestosterone + NADPH + H+
4-androsten-3alpha,17beta-diol + NADP+
DL-glyceraldehyde + NADPH
glycerol + NADP+
-
-
-
-
?
DL-glyceraldehyde 3-phosphate + NADPH + H+
glycerol 3-phosphate + NADP+
dydrogesterone + NADH + H+
20alpha-hydroxydydrogesterone + NAD+
-
-
-
-
?
estrone + NADPH + H+
?
-
-
-
-
?
estrone 3-sulfate + NADPH + H+
?
-
-
-
-
?
ethyl 2-methylacetoacetate + NADPH
NADP+ + ?
ethyl 3-oxovalerate + NADPH + H+
?
ethyl 4-chloroacetoacetate + NADPH
NADP+ + ?
ethyl acetoaetate + NADPH
(S)-ethyl 3-hydroxybutyrate + NADP+
ethyl benzoylacetate + NADPH + H+
?
ethyl pyruvate + NADPH
NADP+ + ?
geraniol + NADP+
?
-
-
-
-
?
hexanal + NADPH + H+
?
-
-
-
-
?
isatin + NADP+
?
-
-
-
-
?
isocaproaldehyde + NADPH + H+
?
-
-
-
-
?
ketotifen + NADPH + H+
?
-
-
-
-
?
menadione + NADPH + H+
?
-
-
-
-
?
methyl acetoacetate + NADPH + H+
?
methylglyoxal + NADPH
NADP+ + ?
methylglyoxal + NADPH + H+
?
-
-
-
-
?
n-butyl acetoacetate + NADPH + H+
?
n-hexyl acetoacetate + NADPH + H+
?
n-octyl acetoacetate + NADPH + H+
?
nonanal + NADPH + H+
?
-
-
-
-
?
phenylglyoxal + NADPH + H+
?
-
-
-
-
r
progesterone + NAD(P)+
20alpha-hydroxyprogesterone + NAD(P)H + H+
-
-
-
?
progesterone + NAD(P)H
20alpha-hydroxypregn-4-en-3-one + NAD(P)+
progesterone + NAD(P)H
20alpha-hydroxyprogesterone + NAD(P)+
progesterone + NAD(P)H + H+
20alpha-hydroxyprogesterone + NAD(P)+
progesterone + NADH
20alpha-hydroxyprogesterone + NAD+
-
-
-
-
?
progesterone + NADH + H+
20alpha-hydroxyprogesterone + NAD+
progesterone + NADPH
20alpha-hydroxyprogesterone + NADP+
progesterone + NADPH + H+
20alpha-hydroxyprogesterone + NADP+
-
-
-
-
?
prostaglandin E2 + NADPH
NADP+ + ?
-
low activity
-
-
?
pyridine 3-aldehyde + NADPH + H+
?
-
-
-
-
?
pyridine-3-aldehyde + NADPH
NADP+ + ?
pyridine-4-aldehyde + NADP+
?
testosterone + NADP+
?
-
-
-
-
?
tetrahydrocortisol + NADH + H+
? + NAD+
trans-1S,2S-cyclohexanediol + NADP+
?
trans-2-hexenal + NADPH + H+
?
-
-
-
-
?
trans-2-nonenal + NADPH + H+
?
-
-
-
-
?
trans-benzene dihydrodiol + NADP+
?
-
-
-
-
?
trans-benzene-1S,2S-dihydrodiol + NADP+
?
additional information
?
-
(S)-methyl 3-hydroxybutyrate + NADP+
methyl acetoacetate + NADPH + H+
-
-
-
-
r
(S)-methyl 3-hydroxybutyrate + NADP+
methyl acetoacetate + NADPH + H+
-
-
-
-
r
1,2-cyclohexanedione + NADP+
?
-
66% activity compared to pyridine 3-aldehyde
-
-
r
1,2-cyclohexanedione + NADP+
?
-
50% activity compared to pyridine 3-aldehyde
-
-
r
1-phenyl-1,2-propanedione + NADPH
NADP+ + ?
-
-
-
-
?
1-phenyl-1,2-propanedione + NADPH
NADP+ + ?
-
-
-
-
?
11-deoxycorticosterone + NAD(P)H
4-pregnen-20alpha,21-diol-3-one + NAD(P)+
-
-
-
-
?
11-deoxycorticosterone + NAD(P)H
4-pregnen-20alpha,21-diol-3-one + NAD(P)+
-
-
-
-
?
11-deoxycortisol + NADH
? + NAD+
-
-
-
-
?
11-deoxycortisol + NADH
? + NAD+
-
-
-
?
11-deoxycortisol + NADH
? + NAD+
-
inducer
-
-
r
11-deoxycortisol + NADH + H+
? + NAD+
i.e. 4-pregnen-17,21-diol-3,20-dione, 66.03% compared to the activity with cortisol
-
-
?
11-deoxycortisol + NADH + H+
? + NAD+
i.e. 4-pregnen-17,21-diol-3,20-dione, 66.03% compared to the activity with cortisol
-
-
?
17alpha,20alpha-dihydroxypregn-4-en-3-one + NAD(P)+
17alpha-hydroxyprogesterone + NAD(P)H
-
-
-
-
r
17alpha,20alpha-dihydroxypregn-4-en-3-one + NAD(P)+
17alpha-hydroxyprogesterone + NAD(P)H
-
inactive molecule form
hormone
-
r
17alpha-hydroxypregnenolone + NADPH
? + NADP+
-
-
-
-
?
17alpha-hydroxypregnenolone + NADPH
? + NADP+
-
-
-
?
17alpha-hydroxypregnenolone + NADPH
? + NADP+
-
-
-
-
?
17alpha-hydroxypregnenolone + NADPH
? + NADP+
-
-
-
-
?
17alpha-hydroxyprogesterone + NAD(P)H
17alpha,20alpha-dihydroxypregn-4-en-3-one + NAD(P)+
-
-
-
r
17alpha-hydroxyprogesterone + NAD(P)H
17alpha,20alpha-dihydroxypregn-4-en-3-one + NAD(P)+
the aldo-keto reductase, AKR1C23, also shows 20alpha-hydroxysteroid dehydrogenase activity in vivo, enzyme regulation in preovulatory follicles and corpora lutea, overview
-
-
r
17alpha-hydroxyprogesterone + NAD(P)H
17alpha,20alpha-dihydroxypregn-4-en-3-one + NAD(P)+
-
-
-
-
r
17alpha-hydroxyprogesterone + NAD(P)H
17alpha,20alpha-dihydroxypregn-4-en-3-one + NAD(P)+
-
the enzyme activity is highest in women with visceral obesity
-
-
r
17alpha-hydroxyprogesterone + NAD(P)H
17alpha,20alpha-dihydroxypregn-4-en-3-one + NAD(P)+
-
-
-
-
r
17alpha-hydroxyprogesterone + NAD(P)H
17alpha,20alpha-dihydroxypregn-4-en-3-one + NAD(P)+
-
NADPH is preferred to NADH in liver, while the kidney enzyme is specific for NADPH
-
-
r
17alpha-hydroxyprogesterone + NAD(P)H
17alpha,20alpha-dihydroxypregn-4-en-3-one + NAD(P)+
-
progesterone catabolism
-
-
r
17alpha-hydroxyprogesterone + NAD(P)H
17alpha,20alpha-dihydroxypregn-4-en-3-one + NAD(P)+
-
regulation of enzyme expression during pregnancy, the enzyme is required for prostaglandin F2alpha-dependent progesterone down-regulation before parturition, overview
-
-
r
17alpha-hydroxyprogesterone + NAD(P)H
17alpha,20alpha-dihydroxypregn-4-en-3-one + NAD(P)+
-
-
-
-
r
17alpha-hydroxyprogesterone + NAD(P)H
17alpha,20alpha-dihydroxypregn-4-en-3-one + NAD(P)+
-
progesterone catabolism
-
-
r
17alpha-hydroxyprogesterone + NAD(P)H
17alpha,20alpha-dihydroxypregn-4-en-3-one + NAD(P)+
-
-
-
-
r
17alpha-hydroxyprogesterone + NAD(P)H + H+
17alpha,20alpha-dihydroxy-pregn-4-en-3-one + NAD(P)+
-
-
-
-
?
17alpha-hydroxyprogesterone + NAD(P)H + H+
17alpha,20alpha-dihydroxy-pregn-4-en-3-one + NAD(P)+
-
NADPH preferred
-
-
?
17alpha-hydroxyprogesterone + NAD(P)H + H+
17alpha,20alpha-dihydroxy-pregn-4-en-3-one + NAD(P)+
-
-
-
-
?
17alpha-hydroxyprogesterone + NAD(P)H + H+
17alpha,20alpha-dihydroxy-pregn-4-en-3-one + NAD(P)+
-
-
-
r
17alpha-hydroxyprogesterone + NAD(P)H + H+
17alpha,20alpha-dihydroxy-pregn-4-en-3-one + NAD(P)+
-
NADPH preferred
-
-
?
17alpha-hydroxyprogesterone + NADPH
17alpha,20alpha-dihydroxyprogesterone + NADP+
-
-
-
?
17alpha-hydroxyprogesterone + NADPH
17alpha,20alpha-dihydroxyprogesterone + NADP+
-
-
-
?
17alpha-hydroxyprogesterone + NADPH + H+
17alpha,20alpha-dihydroxy-pregn-4-en-3-one + NADP+
-
-
-
-
?
17alpha-hydroxyprogesterone + NADPH + H+
17alpha,20alpha-dihydroxy-pregn-4-en-3-one + NADP+
-
-
-
?
17alpha-hydroxyprogesterone + NADPH + H+
17alpha,20alpha-dihydroxy-pregn-4-en-3-one + NADP+
-
-
-
?
17alpha-hydroxyprogesterone + NADPH + H+
17alpha,20alpha-dihydroxy-pregn-4-en-3-one + NADP+
-
-
-
-
r
17alpha-hydroxyprogesterone + NADPH + H+
17alpha,20alpha-dihydroxy-pregn-4-en-3-one + NADP+
-
best substrate
-
r
17alpha-hydroxyprogesterone + NADPH + H+
17alpha,20alpha-dihydroxy-pregn-4-en-3-one + NADP+
-
-
-
-
r
2,3-butanediol + NADP+
?
-
-
-
-
r
2,3-butanediol + NADP+
?
-
-
-
-
r
2,3-butanedione + NADPH
? + NADP+
-
-
-
-
?
2,3-butanedione + NADPH
? + NADP+
-
-
-
-
?
2,3-heptanedione + NADPH
NADP+ + ?
-
-
-
-
?
2,3-heptanedione + NADPH
NADP+ + ?
-
-
-
-
?
2,3-hexanedione + NADPH
NADP+ + ?
-
-
-
-
?
2,3-hexanedione + NADPH
NADP+ + ?
-
-
-
-
?
2,3-pentanedione + NADPH
NADP+ + ?
-
-
-
-
?
2,3-pentanedione + NADPH
NADP+ + ?
-
-
-
-
?
2,4-pentanedione + NADP+
?
-
-
-
-
r
2,4-pentanedione + NADP+
?
-
-
-
-
r
20alpha-hydroxyprogesterone + NADP+
progesterone + NADPH
-
-
-
-
r
20alpha-hydroxyprogesterone + NADP+
progesterone + NADPH
-
-
-
?
20alpha-hydroxyprogesterone + NADP+
progesterone + NADPH
-
-
-
?
20alpha-hydroxyprogesterone + NADP+
progesterone + NADPH
-
-
-
?
3,4-hexanedione + NADP+
?
-
-
-
-
r
3,4-hexanedione + NADP+
?
-
-
-
-
r
4-nitrobenzaldehyde + NADPH
4-nitrobenzyl alcohol + NADP+
-
-
-
-
?
4-nitrobenzaldehyde + NADPH
4-nitrobenzyl alcohol + NADP+
-
-
-
-
?
4-nitrobenzaldehyde + NADPH
4-nitrobenzyl alcohol + NADP+
-
-
-
-
?
5alpha-dihydroprogesterone + NADPH + H+
5alpha,20alpha-tetrahydroprogesterone + NADP+
-
-
-
r
5alpha-dihydroprogesterone + NADPH + H+
5alpha,20alpha-tetrahydroprogesterone + NADP+
-
-
-
r
5alpha-dihydroprogesterone + NADPH + H+
5alpha,20alpha-tetrahydroprogesterone + NADP+
-
-
-
-
r
5alpha-pregnane-3alpha,20alpha-diol + NAD(P)+
3alpha-hydroxy-5alpha-pregnan-20-one + NAD(P)H + H+
-
-
-
-
r
5alpha-pregnane-3alpha,20alpha-diol + NAD(P)+
3alpha-hydroxy-5alpha-pregnan-20-one + NAD(P)H + H+
-
-
-
?
5beta-pregnan-20alpha-ol-3-one + NADP+
?
-
-
-
-
?
5beta-pregnan-20alpha-ol-3-one + NADP+
?
-
-
-
-
r
5beta-pregnane-3alpha,20alpha-diol + NAD(P)+
5beta-pregnan-20alpha-ol-3-one + NAD(P)H + H+
-
-
-
-
?
5beta-pregnane-3alpha,20alpha-diol + NAD(P)+
5beta-pregnan-20alpha-ol-3-one + NAD(P)H + H+
-
-
-
-
r
acetoacetyl-CoA + NADPH
NADP+ + ?
-
-
-
-
?
acetoacetyl-CoA + NADPH
NADP+ + ?
-
-
-
-
?
acetoin + NADPH + H+
?
-
-
-
-
?
acetoin + NADPH + H+
?
-
-
-
-
r
acetoin + NADPH + H+
?
-
-
-
-
r
benzyl acetoacetate + NADPH + H+
?
-
-
-
-
r
benzyl acetoacetate + NADPH + H+
?
-
-
-
-
r
cis-benzene-1,2-dihydrodiol + NADP+
?
-
-
-
-
r
cis-benzene-1,2-dihydrodiol + NADP+
?
-
-
-
-
r
corticosterone + NADH + H+
? + NAD+
i.e. 4-pregnen-11beta,21-diol-3,20-dione, 33.32% compared to the activity with cortisol
-
-
?
corticosterone + NADH + H+
? + NAD+
i.e. 4-pregnen-11beta,21-diol-3,20-dione, 33.32% compared to the activity with cortisol
-
-
?
cortisol + NADH
20alpha-dihydrocortisol + NAD+
-
-
-
r
cortisol + NADH
20alpha-dihydrocortisol + NAD+
-
inducer
-
-
r
cortisol + NADH + H+
20beta-hydroxycortisol + NAD+
-
-
-
?
cortisol + NADH + H+
20beta-hydroxycortisol + NAD+
no activity with NADPH
-
-
?
cortisol + NADH + H+
20beta-hydroxycortisol + NAD+
-
-
-
?
cortisol + NADH + H+
20beta-hydroxycortisol + NAD+
no activity with NADPH
-
-
?
cortisone + NADH
? + NAD+
-
-
-
?
cortisone + NADH
? + NAD+
-
inducer
-
-
r
D-glyceraldehyde + NADPH + H+
glycerol + NADP+
-
-
-
-
r
D-glyceraldehyde + NADPH + H+
glycerol + NADP+
-
-
-
-
r
D-lactaldehyde + NADPH + H+
?
-
-
-
-
r
D-lactaldehyde + NADPH + H+
?
-
-
-
-
r
daunorubicin + NADPH + H+
daunorubicinol + NADP+
inactivation of the anticancer drug
-
-
r
daunorubicin + NADPH + H+
daunorubicinol + NADP+
the enzyme reduces daunorubicin to its corresponding alcohol daunorubicinol using NADPH as the coenzyme
-
-
r
dihydrotestosterone + NADPH + H+
4-androsten-3alpha,17beta-diol + NADP+
reaction of EC 1.1.1.357
-
-
r
dihydrotestosterone + NADPH + H+
4-androsten-3alpha,17beta-diol + NADP+
reaction of EC 1.1.1.357
-
-
r
dihydrotestosterone + NADPH + H+
4-androsten-3alpha,17beta-diol + NADP+
-
reaction of EC 1.1.1.357
-
-
r
DL-glyceraldehyde 3-phosphate + NADPH + H+
glycerol 3-phosphate + NADP+
-
-
-
-
r
DL-glyceraldehyde 3-phosphate + NADPH + H+
glycerol 3-phosphate + NADP+
-
-
-
-
r
ethyl 2-methylacetoacetate + NADPH
NADP+ + ?
-
-
-
-
?
ethyl 2-methylacetoacetate + NADPH
NADP+ + ?
-
-
-
-
?
ethyl 3-oxovalerate + NADPH + H+
?
-
-
-
-
r
ethyl 3-oxovalerate + NADPH + H+
?
-
-
-
-
r
ethyl 4-chloroacetoacetate + NADPH
NADP+ + ?
-
-
-
-
?
ethyl 4-chloroacetoacetate + NADPH
NADP+ + ?
-
-
-
-
?
ethyl acetoaetate + NADPH
(S)-ethyl 3-hydroxybutyrate + NADP+
-
-
-
-
?
ethyl acetoaetate + NADPH
(S)-ethyl 3-hydroxybutyrate + NADP+
-
-
-
r
ethyl benzoylacetate + NADPH + H+
?
-
-
-
-
r
ethyl benzoylacetate + NADPH + H+
?
-
-
-
-
r
ethyl pyruvate + NADPH
NADP+ + ?
-
-
-
-
?
ethyl pyruvate + NADPH
NADP+ + ?
-
-
-
-
?
isatin + NADPH
NADP+ + ?
-
-
-
-
?
isatin + NADPH
NADP+ + ?
-
-
-
-
?
methyl acetoacetate + NADPH + H+
?
-
-
-
-
r
methyl acetoacetate + NADPH + H+
?
-
-
-
-
r
methylglyoxal + NADPH
NADP+ + ?
-
-
-
-
?
methylglyoxal + NADPH
NADP+ + ?
-
-
-
-
?
methylglyoxal + NADPH
NADP+ + ?
-
-
-
-
?
n-butyl acetoacetate + NADPH + H+
?
-
-
-
-
r
n-butyl acetoacetate + NADPH + H+
?
-
-
-
-
r
n-hexyl acetoacetate + NADPH + H+
?
-
-
-
-
r
n-hexyl acetoacetate + NADPH + H+
?
-
-
-
-
r
n-octyl acetoacetate + NADPH + H+
?
-
-
-
-
r
n-octyl acetoacetate + NADPH + H+
?
-
-
-
-
r
phenylglyoxal + NADP+
?
-
-
-
-
r
phenylglyoxal + NADP+
?
-
-
-
-
r
progesterone + NAD(P)H
20alpha-hydroxypregn-4-en-3-one + NAD(P)+
-
-
-
-
r
progesterone + NAD(P)H
20alpha-hydroxypregn-4-en-3-one + NAD(P)+
-
i.e. pregn-4-en-3-one, importance of sulfhydryl groups in the functioning of the enzyme
-
-
r
progesterone + NAD(P)H
20alpha-hydroxyprogesterone + NAD(P)+
-
-
-
-
?
progesterone + NAD(P)H
20alpha-hydroxyprogesterone + NAD(P)+
-
-
-
r
progesterone + NAD(P)H
20alpha-hydroxyprogesterone + NAD(P)+
-
-
-
-
r
progesterone + NAD(P)H
20alpha-hydroxyprogesterone + NAD(P)+
-
NADPH much more efficient, 4-fold lower Km
-
?
progesterone + NAD(P)H + H+
20alpha-hydroxyprogesterone + NAD(P)+
-
-
-
-
ir
progesterone + NAD(P)H + H+
20alpha-hydroxyprogesterone + NAD(P)+
-
maternal and fetal 20alpha-HSD play a role in maintaining normal pregnancy at least partially by reducing progesterone concentrations in fetuses
-
-
?
progesterone + NADH + H+
20alpha-hydroxyprogesterone + NAD+
-
-
-
?
progesterone + NADH + H+
20alpha-hydroxyprogesterone + NAD+
-
-
-
-
?
progesterone + NADH + H+
20alpha-hydroxyprogesterone + NAD+
-
-
-
-
?
progesterone + NADPH
20alpha-hydroxyprogesterone + NADP+
-
-
-
-
?
progesterone + NADPH
20alpha-hydroxyprogesterone + NADP+
-
-
-
-
r
progesterone + NADPH
20alpha-hydroxyprogesterone + NADP+
-
-
-
?
progesterone + NADPH
20alpha-hydroxyprogesterone + NADP+
-
-
-
?
progesterone + NADPH
20alpha-hydroxyprogesterone + NADP+
-
-
-
r
progesterone + NADPH
20alpha-hydroxyprogesterone + NADP+
-
-
-
r
progesterone + NADPH
20alpha-hydroxyprogesterone + NADP+
-
-
-
r
progesterone + NADPH
20alpha-hydroxyprogesterone + NADP+
-
-
-
r
progesterone + NADPH
20alpha-hydroxyprogesterone + NADP+
-
-
-
r
progesterone + NADPH
20alpha-hydroxyprogesterone + NADP+
-
central role in luteolysis and parturition
-
?
progesterone + NADPH
20alpha-hydroxyprogesterone + NADP+
-
-
-
r
progesterone + NADPH
20alpha-hydroxyprogesterone + NADP+
-
less reactive than with 17alpha-hydroxyprogesterone
-
-
?
pyridine-3-aldehyde + NADPH
NADP+ + ?
-
-
-
-
?
pyridine-3-aldehyde + NADPH
NADP+ + ?
-
-
-
-
?
pyridine-4-aldehyde + NADP+
?
-
-
-
-
r
pyridine-4-aldehyde + NADP+
?
-
-
-
-
r
tetrahydrocortisol + NADH + H+
? + NAD+
i.e. 5beta-pregnan-3alpha,11beta,17,21-tetrol-20-one, 44.29% compared to the activity with cortisol
-
-
?
tetrahydrocortisol + NADH + H+
? + NAD+
i.e. 5beta-pregnan-3alpha,11beta,17,21-tetrol-20-one, 44.29% compared to the activity with cortisol
-
-
?
trans-1S,2S-cyclohexanediol + NADP+
?
-
-
-
-
r
trans-1S,2S-cyclohexanediol + NADP+
?
-
-
-
-
r
trans-benzene-1S,2S-dihydrodiol + NADP+
?
-
-
-
-
r
trans-benzene-1S,2S-dihydrodiol + NADP+
?
-
-
-
-
r
additional information
?
-
-
androstenedione and corticosterone not substrates
-
-
?
additional information
?
-
-
negligible activity with dehydroepiandrosterone, estrone estradiol, 4-androstenendione, testosterone and diydrotestosterone as substrates
-
-
?
additional information
?
-
-
pregnancy induces X-zone regression and abolishes 20alphaHSD expression, which is partially restored in animals that are kept from nursing their pups, lactation inhibits enzyme expression, X-zone regulation, overview
-
-
?
additional information
?
-
-
pregnancy induces X-zone regression and abolishes 20alphaHSD expression, which is partially restored in animals that are kept from nursing their pups, lactation inhibits enzyme expression, X-zone regulation, overview
-
-
?
additional information
?
-
-
no activity with 5beta-androstan-17beta-ol-3-one, 5beta-pregnan-20alpha-ol-3-one, testosterone and 20alpha-hydroxy progesterone
-
-
?
additional information
?
-
-
no activity with corticosterone and 5alpha-dihydrotestosterone as substrates, other substrate: 17alpha-hydroxyprogesterone
-
-
?
additional information
?
-
-
high activity for neuroactive steroids, 9,10-phenanthrenequinone and 4-nitrobenzaldehyde, low activity for 17alpha hydroxypregnenolone, D,L-glyceraldehyde and prostaglandin E2, no activity for 20beta-hydroxy-pregn-4-en-3-one, andro-, testosterone, 17alpha-, 17beta-oestradiol, oestrone and 5alpha-dihydrotestosterone, other substrates: DL-glyceraldehyde, prostaglandin E2, D-glucose, prednisolone, D-galactose, prednisone, pregnenolone, 5alpha-pregnane-3,20-dione, 9,10-phenanthrenequinone
-
-
?
additional information
?
-
-
no activity with 20beta isomer of 20alpha-hydroxyprogesterone, rising activity with 20alpha-hydroxyprogesterone concentrations over the range 0.05-1.0 mM, increasing activity with NADP+ over the range 0.01-0.2 mM, no NAD+ activity over this concentration range
-
-
?
additional information
?
-
-
no activity with 20beta-hydroxypregn-4-en-3-one, 5alpha-pregnan-3,20-dione, 3beta-hydroxy-5alpha-pregnan-20-one and 3alpha,20alpha-dihydroxy-5alpha-pregnane
-
-
?
additional information
?
-
-
no activity with 20alpha-hydroxy-4-pregnen-3-one
-
-
?
additional information
?
-
-
benzaldehyde, DL-glyceraldehyde, 4-nitrobenzaldehyde and glucose very efficient substrates, methylglyoxal, 9,10-phenanthrenquinone and D-galactose less active, no activity with corticosterone and 5alpha-dihydrotestosterone
-
-
?
additional information
?
-
-
no activity with corticosterone and 5alpha-dihydrotestosterone as substrates, other substrate: 17alpha-hydroxyprogesterone
-
-
?
additional information
?
-
-
no activity toward estrone with NADPH
-
-
?
additional information
?
-
-
less or no activity with 5beta-androstane-3,17-dione, 17beta-hydroxy-5beta-androstan-3-one, progesterone, 5beta-pregnane-3,20-dione, cortisone oestrone, 20-oxopregnenes without 17alpha-hydroxy group, 20-oxopregnanes, corticosteroides, 3- or 17-oxosteroids, 20beta-hydroxysteroids, 3- or 17-hydroxysteroids, alcohols as substrate, other substrates: isatin, ethyl acetoacetate, camphorquinone, pyridine-3-aldehyde, 1,2-cyclohexanedione, 2,4-pentanedione, 4-nitrobenzaldehyde, benzene-dihydrodiol
-
-
?
additional information
?
-
-
other substrates: 2,3-butanedione to 2,3-heptanedione, 1-phenyl-1,2-propanedione, ethyl 2-methylacetoacetate, acetoacetyl-CoA, ethyl pyruvate, ethyl 4-chloroacetoacetate, isatin, pyridine-3-aldehyde , not 20beta-hydroxysteroids, 1,2-cyclohexanedione, methyl acetoacetate, 2,4-pentanedione, acetoin, 4-nitrobenzaldehyde, ethyl 3-oxovalerate, 3,4-hexanedione, D-glyceraldehyde, ethyl benzoylacetate, D-lactaldehyde, DL-glceraldehyde 3-phosphate, pyridine-4-aldehyde, (S)-ethyl-3-hydroxybutyrate, trans-benzene-1S,2S-dihydrodiol, cis-benzene-1,2-dihydrodiol, (S)-methyl 3-hydroxybutyrate
-
-
?
additional information
?
-
-
role of enzyme suggested to be for detoxication or metabolism of carbonyl compounds because of broad substrate specificity
-
-
?
additional information
?
-
-
role of enzyme suggested to be for detoxication or metabolism of carbonyl compounds because of broad substrate specificity
-
-
?
additional information
?
-
-
other substrates: 2,3-butanedione to 2,3-heptanedione, 1-phenyl-1,2-propanedione, ethyl 2-methylacetoacetate, acetoacetyl-CoA, ethyl pyruvate, ethyl 4-chloroacetoacetate, isatin, pyridine-3-aldehyde , not 20beta-hydroxysteroids, 1,2-cyclohexanedione, methyl acetoacetate, 2,4-pentanedione, acetoin, 4-nitrobenzaldehyde, ethyl 3-oxovalerate, 3,4-hexanedione, D-glyceraldehyde, ethyl benzoylacetate, D-lactaldehyde, DL-glceraldehyde 3-phosphate, pyridine-4-aldehyde, (S)-ethyl-3-hydroxybutyrate, trans-benzene-1S,2S-dihydrodiol, cis-benzene-1,2-dihydrodiol, (S)-methyl 3-hydroxybutyrate
-
-
?
additional information
?
-
-
role of enzyme suggested to be for detoxication or metabolism of carbonyl compounds because of broad substrate specificity
-
-
?
additional information
?
-
-
17alpha-hydroxyprogesterone inducer but not substrate
-
-
?
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1,10-phenanthroline
-
50% inhibition at 0.065 mM
1,2-naphthoquinone
-
0.01 mM, 55% inhibition of enzyme in liver, 10% in kidney, 10% in lung cytosolic fraction, respectively
1-phenylcyclopentanecarboxylic acid
-
16alpha-Bromoacetoxyprogesterone
-
-
17alpha-hydroxyprogesterone
-
most inhibitory at pH 8.0, significant at pH 6.8
17beta-estradiol
-
20alpha-hydroxyprogesterone analog, competitive or noncompetitive depending on variable substrate
2',5'-adenosine bisphosphate
-
competitive inhibition versus NADP+
2',5'-ADP
-
coenzyme-competitive inhibitor
2'-adenylic acid
-
coenzyme-competitive inhibitor
2'-phosphoadenosine diphosphoribose
2,4-Pentanedione
-
pH profile for the inactivation, overview
2-(4-chlorobenzylidene)cyclopentanone
-
2-(4-chlorobenzylidene)cyclopentyl ethyl ether
-
2-acetylbenzofuran
-
50% inhibition at 0.033 mM
20beta-hydroxypregn-4-en-3-one
-
marginally inhibitory at pH 8.0
3',3'',5',5''-tetrabromophenolphthalein
3',3'',5',5''-tetrabromophenolphthalein diacetate
-
50% inhibition at 350 nM
3',3'',5',5''-tetraiodophenolphthalein
-
50% inhibition at 120 nM
3',5'-cyclic AMP
-
coenzyme-competitive inhibitor
3,5-dibromo-4-hydroxybenzoic acid methyl ester
-
50% inhibition at 0.099 mM
3,5-dibromosalicylic acid
-
-
3,5-dichlorosalicylic acid
3,5-diiodosalicylic acid
-
competitive
3-Aminopyridine 1,N6-ethenoadenine dinucleotide phosphate
-
NADP analog, competitive inhibitor
3-Aminopyridine adenine dinucleotide phosphate
3-bromo-5-phenylsalicylic acid
3-chloro-5-phenylsalicylic acid
3-phenyl-5-bromosalicylic acid
-
-
3-phenylcyclopentanecarboxylic acid
-
4'-butyl-5-chloro-4-hydroxybiphenyl-3-carboxylic acid
7fold selectivity relative to 3alpha-hydroxysteroid dehydrogenase AKR1C2
5'-adenosine diphosphate
-
-
5'-Adenosine triphosphate
-
-
5'-adenylic acid
-
coenzyme-competitive inhibitor
5'-ADP
-
coenzyme-competitive inhibitor
5'-ATP
-
coenzyme-competitive inhibitor
5-chloro-4-hydroxy-3'-methylbiphenyl-3-carboxylic acid
13fold selectivity relative to 3alpha-hydroxysteroid dehydrogenase AKR1C2
5-chloro-4-hydroxy-4'-methylbiphenyl-3-carboxylic acid
24fold selectivity relative to 3alpha-hydroxysteroid dehydrogenase AKR1C2
5-chloro-4-hydroxybiphenyl-3-carboxylic acid
24fold selectivity relative to 3alpha-hydroxysteroid dehydrogenase AKR1C2
5-fluoro-4-hydroxybiphenyl-3-carboxylic acid
1.2fold selectivity relative to 3alpha-hydroxysteroid dehydrogenase AKR1C2
5alpha-dihydrotestosterone
-
-
5beta-dihydrotestosterone
-
-
9,10-phenanthrenequinone
-
0.01 mM, 70% inhibition of enzyme in liver, 5% in kidney, 60% in lung cytosolic fraction, respectively
adenosine 2'-monophospho- 5'-diphosphoribose
-
strong inhibition
adenosine diphosphoribose
-
coenzyme-competitive inhibitor
aminopyridine 1,N6-ethenoadenine dinucleotide phosphate
-
-
aminopyridine adenine dinucleotide phosphate
-
-
androstendione
-
most inhibitory at pH 8.0
benzbromarone acetate
-
50% inhibition at 430 nM
benzofuran
-
50% inhibition at 1.45 mM
benzofuran-2-carboxylic acid
-
50% inhibition at 0.16 mM
Bethamethasone
-
0.1 mM, 10% inhibition
carboxylic acid
-
competitive for acetic and propionic acid, mixed-type from pentanoic to undecanoic acid with exception of heptanoic acid
cloxazolam
-
0.01 mM, 38% inhibition
diazepam
-
50% inhibition at 0.0056 mM
Diazotized 3-aminopyridine 1,N6-ethenoadenine dinucleotide phosphate
-
NADP+ analog, competitive inhibitor
Diazotized 3-aminopyridine adenine dinucleotide phosphate
-
NADP analog, competitive inhibitor
dibenzofuran
-
50% inhibition at 0.895 mM
Diphenic acid
-
less than 17% inhibition
Fluorescein mercuric acetate
-
-
glycerol
-
inhibition partially reversed by cysteine
glycyrrhetinic acid
-
50% inhibition at 0.0022 mM
linear monocarboxylic acids
-
slight inhibition, overview
-
linear N-alkylammonium chloride derivatives
-
slight inhibition, overview
-
lithocholic acid
-
50% inhibition at 0.022 mM
Maleimide
-
pH profile for the inactivation, overview
Meclofenamic acid
-
20alpha-hydroxyprogesterone oxidation
medazepam
-
50% inhibition at 0.0047 mM
Medroxyprogesterone acetate
-
50% inhibition at 700 nM
N-1-butylnicotinamide chloride
-
inhibition of the ovarian enzyme, competitive inhibition versus NADP+
N-1-decylnicotinamide chloride
-
inhibition of the ovarian enzyme, mixed type inhibition versus NADP+
N-1-dodecylnicotinamide chloride
-
inhibition of the ovarian enzyme, mixed type inhibition versus NADP+
N-1-ethylnicotinamide chloride
-
inhibition of the ovarian enzyme, competitive inhibition versus NADP+
N-1-heptylnicotinamide chloride
-
inhibition of the ovarian enzyme, competitive inhibition versus NADP+
N-1-hexylnicotinamide chloride
-
inhibition of the ovarian enzyme, competitive inhibition versus NADP+
N-1-methylnicotinamide chloride
-
inhibition of the ovarian enzyme, competitive inhibition versus NADP+
N-1-nonylnicotinamide chloride
-
inhibition of the ovarian enzyme, mixed type inhibition versus NADP+
N-1-octylnicotinamide chloride
-
inhibition of the ovarian enzyme, mixed type inhibition versus NADP+
N-1-pentylnicotinamide chloride
-
inhibition of the ovarian enzyme, competitive inhibition versus NADP+
N-1-propylnicotinamide chloride
-
inhibition of the ovarian enzyme, competitive inhibition versus NADP+
N-1-undecylnicotinamide chloride
-
inhibition of the ovarian enzyme, mixed type inhibition versus NADP+
N-alkylammonium chloride
-
competitive from pentyl to heptyl, mixed type from nonyl to dodecyl
N-Alkylmaleimide
-
N-ethylmaleimide and N-butylmaleimide to N-octylmaleimide at 25°C, pH 7.7
N-alkylmaleimides
-
coenzyme-competitive inhibition, varying in chainlength from N-ethyl- to N-octylmaleimide, effectively inactivated the enzyme through pseudo-first-order rate processes, overview
-
N-Butylmaleimide
-
inactivation via sulfhydryl groups of the enzyme in a nonpolar region
N-ethylmaleimide
-
inactivation via sulfhydryl groups of the enzyme in a nonpolar region
N-Heptylmaleimide
-
inactivation via sulfhydryl groups of the enzyme in a nonpolar region
N-Hexylmaleimide
-
inactivation via sulfhydryl groups of the enzyme in a nonpolar region
N-Octylmaleimide
-
inactivation via sulfhydryl groups of the enzyme in a nonpolar region
N-Pentylmaleimide
-
inactivation via sulfhydryl groups of the enzyme in a nonpolar region
N1-alkylnicotinamide chloride
-
competitive from methyl to heptyl, mixed-type from octyl to dodecyl with respect to NADP
NAD+
-
NADP analog, competitive inhibitor
NADH
-
concentrations above 0.1 mM
NADPH
-
competitive and noncompetitive product inhibition with respect to NADP+ depending on substrate concentrations
natural oestrogens
-
e.g. oestrone less than 15% inhibition
-
o-cresolphthalein
-
50% inhibition at 140 nM
p-chloromercuribenzoate
-
also other sufhydryl reagents like 5,5'-dithiobis-2-nitrobenzoic acid and iodoacetamide strong
phenazine methosulfate
-
0.01-0.3 mg/ml
prolactin
-
down-regulating of gene-expression
-
pyridoxal 5'-phosphate
-
strong, 90% inactivation by 10 mM
synthetic non-steroidal oestrogens
-
hexoestrol most potent competitive inhibitor
-
synthetic oestrogens
-
e.g. hexestrol, silbestrol, dienstrol
-
Ursodeoxycholic acid
-
50% inhibition at 0.34 mM
valporic acid
-
less than 17% inhibition
2'-phosphoadenosine diphosphoribose
-
coenzyme-competitive inhibitor
2'-phosphoadenosine diphosphoribose
-
NADP+ analog, competitive or noncompetitive depending on variable substrate
3',3'',5',5''-tetrabromophenolphthalein
-
50% inhibition at 33 nM
3',3'',5',5''-tetrabromophenolphthalein
-
-
3,5-dichlorosalicylic acid
potent inhibitor
3,5-dichlorosalicylic acid
-
3,5-dichlorosalicylic acid
-
-
3-Aminopyridine adenine dinucleotide phosphate
-
NADP analog, competitive inhibitor
3-Aminopyridine adenine dinucleotide phosphate
-
diazotized, coenzyme-competitive at 25°C, pH 7.4, reversible binding
3-Aminopyridine adenine dinucleotide phosphate
-
-
3-bromo-5-phenylsalicylic acid
-
-
3-bromo-5-phenylsalicylic acid
-
3-chloro-5-phenylsalicylic acid
-
3-chloro-5-phenylsalicylic acid
-
-
apigenin
-
high inhibition
apigenin
-
0.02 mM, 90% inhibition of enzyme in liver cytosolic fraction, 0.05 mM, 45% inhibition in kidney cytosolic fraction
apigenin
-
inhibitory effect on hepatic NADPH-dependent activity in decreasing order: fisetin > apigenin > naringenin > quercetin
benzbromarone
-
50% inhibition at 48 nM
Bile acids
-
e.g. lithocholic acid, competitive with respect to (S)-ethyl 3-hydroxybutyrate
Bile acids
-
e.g. lithocholic acid, competitive with respect to (S)-ethyl 3-hydroxybutyrate
Bromophenol blue
-
50% inhibition at 0.011 mM
Bromophenol blue
-
little effect on hepatic NADPH-dependent 20alpha-hydroxysteroid dehydrogenase, moderate inhibitor of hepatic NADH-dependent 20alpha-hydroxysteroid dehydrogenase activity
cibacron
-
coenzyme analog, competitively with respect to both coenzymes
cibacron
-
coenzyme analog, competitively with respect to both coenzymes
Cu2+
-
very powerful
Dienstrol
-
competitive with respect to (S)-ethyl 3-hydroxybutyrate
Dienstrol
-
competitive with respect to (S)-ethyl 3-hydroxybutyrate
ethyl acetate
-
noncompetitively with respect to NADP+ and (S)-ethyl 3-hydroxybutyrate at backward reaction
ethyl acetate
-
noncompetitively with respect to NADP+ and (S)-ethyl 3-hydroxybutyrate at backward reaction
fatty acids
-
e.g. myristic acid, competitive with respect to (S)-ethyl 3-hydroxybutyrate
fatty acids
-
e.g. myristic acid, competitive with respect to (S)-ethyl 3-hydroxybutyrate
fisetin
-
high inhibition
fisetin
-
0.02 mM, 95% inhibition of enzyme in liver cytosolic fraction, 0.05 mM, 20% inhibition in kidney cytosolic fraction
fisetin
-
inhibitory effect on hepatic NADPH-dependent activity in decreasing order: fisetin > apigenin > naringenin > quercetin
Flufenamic acid
-
50% inhibition at 0.0053 mM
Flufenamic acid
-
poor inhibition for 20alpha-hydroxyprogesterone oxidation
Hexestrol
-
50% inhibition at 0.0083 mM
indomethacin
-
50% inhibition at 0.13 mM
indomethacin
-
less than 17% inhibition
kaempferol
-
high inhibition
kaempferol
-
0.02 mM, 80% inhibition of enzyme in liver cytosolic fraction, 0.05 mM, 15% inhibition in kidney cytosolic fraction
kaempferol
-
potent and competitive inhibitor
luteolin
-
high inhibition
luteolin
-
0.02 mM, 80% inhibition of enzyme in liver cytosolic fraction, 0.05 mM, 40% inhibition in kidney cytosolic fraction
myricetin
-
0.02 mM, 60% inhibition of enzyme in liver cytosolic fraction, 0.05 mM, 10% inhibition in kidney cytosolic fraction
NADP+
-
coenzyme-competitive inhibitor
NADP+
-
(non)competitively with respect to NADPH and ethyl acetoacetate at forward reaction
NADP+
-
(non)competitively with respect to NADPH and ethyl acetoacetate at forward reaction
naringenin
-
high inhibition
naringenin
-
0.02 mM, 85% inhibition of enzyme in liver cytosolic fraction, 0.05 mM, 3% inhibition in kidney cytosolic fraction
naringenin
-
inhibitory effect on hepatic NADPH-dependent activity in decreasing order: fisetin > apigenin > naringenin > quercetin
Phenobarbital
-
competitive with respect to (S)-ethyl 3-hydroxybutyrate
Phenobarbital
-
competitive with respect to (S)-ethyl 3-hydroxybutyrate
Phenolphthalein
-
50% inhibition at 340 nM
progesterone
-
noncompetitive product inhibition
progesterone
-
1.5 mM marginally inhibitory at pH 8.0, 0.75-1.5 mM reduces activity at pH 6.8 by 46 and 60%, respectively; most inhibitory at pH 8.0, significant at pH 6.8
quercetin
-
high inhibition
quercetin
-
0.02 mM, 85% inhibition of enzyme in liver cytosolic fraction, 0.05 mM, 20% inhibition in kidney cytosolic fraction
quercetin
-
inhibitory effect on hepatic NADPH-dependent activity in decreasing order: fisetin > apigenin > naringenin > quercetin
quercetin
-
potent and competitive inhibitor
quercitrin
-
-
quercitrin
-
competitive with respect to (S)-ethyl 3-hydroxybutyrate
quercitrin
-
competitive with respect to (S)-ethyl 3-hydroxybutyrate
sorbinil
-
competitive with respect to (S)-ethyl 3-hydroxybutyrate
sorbinil
-
competitive with respect to (S)-ethyl 3-hydroxybutyrate
Sulfobromophthalein
-
little effect on hepatic NADPH-dependent 20alpha-hydroxysteroid dehydrogenase, potent inhibitor of hepatic NADH-dependent 20alpha-hydroxysteroid dehydrogenase activity
Tolrestat
-
competitive with respect to (S)-ethyl 3-hydroxybutyrate
Tolrestat
-
competitive with respect to (S)-ethyl 3-hydroxybutyrate
additional information
-
pregnancy induces X-zone regression and abolishes 20alphaHSD expression, which is partially restored in animals that are kept from nursing their pups
-
additional information
-
adenosine: no inhibition, important features of coenzyme structure binding to coenzyme-binding site are 2'-phosphate, diphosphate and the positively charged ring nitrogen, hydrophobic region nearby the NADP-binding site might be responsible for nonpolar faciliation of the rates of maleimide inactivation; no inhibition by ATP, 3,5-cyclic AMP, and by adenosine up to 7.5 mM
-
additional information
-
apparent second-order rate constants for inactivation are observed to increase with increasing chain length of the N-alkylmaleimide used, NADP-and coenzyme-competitive inhibitors such as 3-aminopyridine adenine dinucleotide phosphate and various adenosine derivatives protect the enzyme against maleimide inactivation, whereas no protection is observed with the steroid substrate, overview; NADP+, 3-aminopyridine adenine dinucleotide phosphate and three adenosine derivatives protect enzyme against inactivation by N-ethylmaleimide, 20alpha-hydroxyprogesterone does not and N1-ethylnicotinamide chloride not significantly; sulfhydryl groups are modified during inactivation
-
additional information
-
no inhibition by NADPH with saturating concentration of NADP+
-
additional information
-
not inhibited by indomethacin, tolmetin and steroidal anti-inflammatory drugs
-
additional information
-
no inhibition but increase at preincubation with antiserum
-
additional information
-
Ca2+, Fe2+, Mg2+, Mn2+, Cd2+ and Zn2+ no significant effect
-
additional information
-
no inhibition with thiol reagents, reducing or chelating agents, ADH inhibitors
-
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
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0.131
(S)-1-indanol
-
at pH 7.4 and 37°C
0.112
(S)-1-tetralol
-
at pH 7.4 and 37°C
1 - 1870
(S)-ethyl 3-hydroxybutyrate
4.8 - 5
(S)-methyl 3-hydroxybutyrate
0.007 - 0.47
(S)-tetralol
0.092 - 0.129
1,2-Cyclohexanedione
0.006
1-phenyl-1,2-propanedione
0.0033
11-deoxycorticosterone
-
pH 7.4, 37°C
0.073
17-hydroxyprogesterone
-
-
0.013
17alpha,20alpha-dihydroxypregn-4-en-3-one
-
-
0.013 - 0.014
17alpha,20alpha-dihydroxyprogesterone
0.022
17alpha,21-dihydroxy-5beta-pregnan-3,20-dione
-
-
0.02
17alpha,21-dihydroxy-5beta-pregnane-3,11,20-trione
-
-
0.002 - 0.0034
17alpha-hydroxypregnenolone
0.0029 - 0.118
17alpha-hydroxyprogesterone
0.0013
17beta-estradiol
-
at pH 7.4 and 37°C
34.8 - 66.3
2,3-Butanediol
0.015 - 0.018
2,3-Butanedione
0.005 - 0.008
2,3-heptanedione
0.01 - 0.016
2,3-Hexanedione
0.018 - 0.021
2,3-Pentanedione
0.131 - 0.243
2,4-Pentanedione
0.0026
2-amino-8-((2-fluoro-4-methoxybenzyl)thio)-1,9-dihydro-6H-purin-6-one
-
pH 7.0, 25°C
0.001
2-tert-butyl-1,4-benzoquinone
-
at pH 7.4 and 37°C
0.041
20alpha-dihydrocortisol
-
NAD+, pH 7.9
0.00102 - 0.00516
20alpha-hydroxy-4-pregnen-3-one
0.013
20alpha-hydroxy-5alpha-pregnan-3-one
-
+/-0.0035
0.073
20alpha-hydroxy-5beta-pregnan-3-one
-
-
0.00117 - 2.5
20alpha-hydroxyprogesterone
0.23 - 0.57
3,4-hexanedione
0.00208
3-acetylpyridine adenine dinucleotide phosphate
-
NADP analog
1.4
3-deoxyglucosone
-
at pH 7.4 and 37°C
0.012
3alpha-hydroxy-5alpha-pregnan-20-one
-
+/-0.0035
0.001
4-androstene-3,17-dione
-
at pH 7.4 and 37°C
0.152
4-chromanol
-
at pH 7.4 and 37°C
0.0053
4-hydroxy-2-nonenal
-
at pH 7.4 and 37°C
0.0012
4-Nitroacetophenone
-
at pH 7.4 and 37°C
0.221 - 0.3811
4-nitrobenzaldehyde
0.0059
4-oxo-2-hexenal
-
at pH 7.4 and 37°C
0.0018
4-oxo-2-nonenal
-
at pH 7.4 and 37°C
0.016
4-pregnen-20alpha-ol-3-one
-
pH 7.0, 25°C
0.001
4-pregnen-3alpha-ol-20-one
-
at pH 7.4 and 37°C
0.0031
5-androstene-3beta,17beta-diol
-
at pH 7.4 and 37°C
0.0042
5alpha-androstan-3alpha,17beta-diol
-
at pH 7.4 and 37°C
0.0041
5alpha-Androstan-3alpha-ol-17-one
-
at pH 7.4 and 37°C
0.0022
5alpha-androstan-3beta,17beta-diol
-
at pH 7.4 and 37°C
0.006
5alpha-Androstan-3beta-ol-17-one
-
at pH 7.4 and 37°C
0.0034 - 0.018
5alpha-dihydrotestosterone
0.0007 - 0.011
5alpha-pregnan-20alpha-ol-3-one
0.0005
5alpha-pregnan-3,20-dione
-
at pH 7.4 and 37°C
0.0008
5alpha-pregnan-3alpha,20alpha-diol
-
at pH 7.4 and 37°C
0.0062
5alpha-Pregnan-3alpha,21-diol-20-one
-
at pH 7.4 and 37°C
0.0013 - 0.0033
5alpha-pregnan-3alpha-ol-20-one
0.0012
5alpha-pregnane-21-ol-3,20-dione
-
pH 7.0, 25°C
0.0011
5alpha-pregnane-3,20-dione
-
pH 7.0, 25°C
0.0004 - 0.0009
5alpha-pregnane-3alpha,20alpha-diol
0.0062
5beta-androstan-17beta-ol-3-one
-
at pH 7.4 and 37°C
0.0014
5beta-Androstan-3alpha,17beta-diol
-
at pH 7.4 and 37°C
0.0017
5beta-Androstan-3alpha-ol-17-one
-
at pH 7.4 and 37°C
0.0025
5beta-Androstan-3beta,17beta-diol
-
at pH 7.4 and 37°C
0.0028
5beta-androstan-3beta-ol-17-one
-
at pH 7.4 and 37°C
0.001 - 0.073
5beta-pregnan-20alpha-ol-3-one
0.001
5beta-pregnan-3,20-dione
-
at pH 7.4 and 37°C
0.0078
5beta-pregnan-3alpha,20alpha-diol
-
at pH 7.4 and 37°C
0.0026
5beta-Pregnan-3alpha,21-diol-20-one
-
at pH 7.4 and 37°C
0.001 - 0.0062
5beta-Pregnan-3alpha-ol-20-one
0.0012
5beta-pregnane-3,20-dione
-
pH 7.0, 25°C
0.0015
5beta-pregnane-3alpha,20alpha-diol
-
pH 7.0, 25°C
0.002
6-tert-butyl-2,3-epoxy-5-cyclohexen-1,4-dione
-
at pH 7.4 and 37°C
0.0029
7alpha-hydroxy-dehydroepiandrosterone
-
at pH 7.4 and 37°C
0.00195
9,10-phenanthrenequinone
-
+/-0.0004
0.02 - 0.022
acetoacetyl-CoA
0.014
acrolein
-
at pH 7.4 and 37°C
0.0089
all-trans-retinal
-
at pH 7.4 and 37°C
0.053
alpha-tetralone
-
at pH 7.4 and 37°C
0.034
befunolol
-
at pH 7.4 and 37°C
2.1
benzene dihydrodiol
-
-
0.008
benzyl acetoacetate
0.018
beta-ionol
-
at pH 7.4 and 37°C
2.02 - 2.9
cis-benzene-1,2-dihydrodiol
0.022
cortisone
-
NADH, pH 6.3
120
D,L-glyceraldehyde
-
-
0.3 - 0.67
D-glyceraldehyde
0.534 - 0.587
D-Lactaldehyde
0.006
dehydroepiandrosterone
-
at pH 7.4 and 37°C
0.0042
dehydroepiandrosterone 3-sulfate
-
at pH 7.4 and 37°C
0.019
diacetyl
-
at pH 7.4 and 37°C
0.069 - 0.151
dihydrotestosterone
0.852 - 1.3
DL-glyceraldehyde 3-phosphate
0.0011
estrone
-
at pH 7.4 and 37°C
0.0067
Estrone 3-sulfate
-
at pH 7.4 and 37°C
0.012 - 0.015
ethyl 2-methylacetoacetate
0.222 - 0.447
ethyl 3-oxovalerate
0.027
ethyl 4-chloroacetoacetate
0.02 - 20
ethyl acetoacetate
0.303 - 0.654
ethyl benzoylacetate
0.18
geraniol
-
at pH 7.4 and 37°C
0.0076
hexanal
-
at pH 7.4 and 37°C
0.068
isocaproaldehyde
-
at pH 7.4 and 37°C
0.111
ketotifen
-
at pH 7.4 and 37°C
0.018
menadione
-
at pH 7.4 and 37°C
0.117 - 0.123
methyl acetoacetate
0.088 - 0.548
methylglyoxal
0.004
n-butyl acetoacetate
0.0015 - 0.0024
n-hexyl acetoacetate
0.0013 - 0.0016
n-octyl acetoacetate
0.526
NAD+
-
20alpha-dihydrocortisol
0.1429
nicotinamide 1,N6-ethenoadenine dinucleotide phosphate
-
NADP analog
0.0588
nicotinamide hypoxanthine dinucleotide phosphate
-
NADP analog
0.0009
Nonanal
-
at pH 7.4 and 37°C
0.43 - 0.591
Phenylglyoxal
0.0006 - 0.2833
progesterone
0.061
pyridine 3-aldehyde
-
at pH 7.4 and 37°C
0.049 - 0.081
Pyridine-3-aldehyde
0.945 - 1.06
Pyridine-4-aldehyde
0.013
testosterone
-
at pH 7.4 and 37°C
0.00186
thionicotinamide adenine dinucleotide phosphate
-
NADP analog
50.9 - 79.7
trans-1S,2S-cyclohexanediol
0.0074
trans-2-hexenal
-
at pH 7.4 and 37°C
0.0055
trans-2-nonenal
-
at pH 7.4 and 37°C
0.26
trans-benzene dihydrodiol
-
at pH 7.4 and 37°C
1.6
trans-benzene-1S,2S-dihydrodiol
additional information
additional information
-
1 - 1.3
(S)-ethyl 3-hydroxybutyrate
-
-
1 - 1.3
(S)-ethyl 3-hydroxybutyrate
-
-
1870
(S)-ethyl 3-hydroxybutyrate
-
+/-60
4.8 - 5
(S)-methyl 3-hydroxybutyrate
-
-
4.8 - 5
(S)-methyl 3-hydroxybutyrate
-
-
0.007
(S)-tetralol
wild-type, pH 7.4, 25°C
0.016
(S)-tetralol
mutant L308V, pH 7.4, 25°C
0.47
(S)-tetralol
mutant L308A, pH 7.4, 25°C
0.092 - 0.129
1,2-Cyclohexanedione
-
-
0.125
1,2-Cyclohexanedione
-
-
0.129
1,2-Cyclohexanedione
-
-
0.006
1-phenyl-1,2-propanedione
-
-
0.006
1-phenyl-1,2-propanedione
-
-
0.013 - 0.014
17alpha,20alpha-dihydroxyprogesterone
-
-
0.013 - 0.014
17alpha,20alpha-dihydroxyprogesterone
-
-
0.002 - 0.003
17alpha-hydroxypregnenolone
-
-
0.002 - 0.003
17alpha-hydroxypregnenolone
-
-
0.0034
17alpha-hydroxypregnenolone
-
-
0.0029
17alpha-hydroxyprogesterone
-
-
0.003
17alpha-hydroxyprogesterone
-
-
0.003
17alpha-hydroxyprogesterone
-
-
0.003 - 0.012
17alpha-hydroxyprogesterone
-
0.0058
17alpha-hydroxyprogesterone
-
pH 7.4, 37°C
0.0154
17alpha-hydroxyprogesterone
-
+/-0.0029
0.0262
17alpha-hydroxyprogesterone
-
isozyme HSD-I
0.118
17alpha-hydroxyprogesterone
-
isozyme HSD-II
34.8 - 66.3
2,3-Butanediol
-
-
0.015 - 0.018
2,3-Butanedione
-
-
0.015 - 0.018
2,3-Butanedione
-
-
0.005 - 0.008
2,3-heptanedione
-
-
0.005 - 0.008
2,3-heptanedione
-
-
0.01 - 0.016
2,3-Hexanedione
-
-
0.01 - 0.016
2,3-Hexanedione
-
-
0.018 - 0.021
2,3-Pentanedione
-
-
0.018 - 0.021
2,3-Pentanedione
-
-
0.131 - 0.243
2,4-Pentanedione
-
-
0.21
2,4-Pentanedione
-
-
0.243
2,4-Pentanedione
-
-
0.00102
20alpha-hydroxy-4-pregnen-3-one
-
spectrophotometric, pH 6.8
0.00162
20alpha-hydroxy-4-pregnen-3-one
-
fluorometric, pH 7.8
0.0023
20alpha-hydroxy-4-pregnen-3-one
-
-
0.00475
20alpha-hydroxy-4-pregnen-3-one
-
HSD1
0.00516
20alpha-hydroxy-4-pregnen-3-one
-
HSD2
0.00117
20alpha-hydroxyprogesterone
-
wild type, pH 7.5, 37°C
0.0022
20alpha-hydroxyprogesterone
-
at pH 7.4 and 37°C
0.0058 - 0.0059
20alpha-hydroxyprogesterone
-
37°C, 10 min
0.0075
20alpha-hydroxyprogesterone
-
-
0.009
20alpha-hydroxyprogesterone
-
+/-0.0001
0.098
20alpha-hydroxyprogesterone
-
mutant H222I, pH 7.5, 37°C
0.12
20alpha-hydroxyprogesterone
-
A, B and C loop changed, total converted enzyme
0.13
20alpha-hydroxyprogesterone
-
A and C loop changed, bifunctional enzyme
0.1774
20alpha-hydroxyprogesterone
-
mutant H222S, pH 7.5, 37°C
0.3
20alpha-hydroxyprogesterone
-
0.015-0.1 mM, 6 min
2.5
20alpha-hydroxyprogesterone
-
-
0.23 - 0.57
3,4-hexanedione
-
-
0.221 - 0.254
4-nitrobenzaldehyde
-
-
0.221 - 0.254
4-nitrobenzaldehyde
-
-
0.34
4-nitrobenzaldehyde
-
-
0.3811
4-nitrobenzaldehyde
-
+/-0.0605
0.0034
5alpha-dihydrotestosterone
-
at pH 7.4 and 37°C
0.018
5alpha-dihydrotestosterone
-
at pH 7.4 and 37°C
0.0007
5alpha-pregnan-20alpha-ol-3-one
-
pH 7.0, 25°C
0.0027
5alpha-pregnan-20alpha-ol-3-one
-
pH 7.0, 25°C
0.0059
5alpha-pregnan-20alpha-ol-3-one
-
at pH 7.4 and 37°C
0.011
5alpha-pregnan-20alpha-ol-3-one
-
at pH 7.4 and 37°C
0.0013
5alpha-pregnan-3alpha-ol-20-one
-
at pH 7.4 and 37°C
0.002
5alpha-pregnan-3alpha-ol-20-one
-
pH 7.0, 25°C
0.0033
5alpha-pregnan-3alpha-ol-20-one
-
pH 7.0, 25°C
0.0004
5alpha-pregnane-3alpha,20alpha-diol
mutant L308V, pH 7.4, 25°C
0.0009
5alpha-pregnane-3alpha,20alpha-diol
-
pH 7.0, 25°C
0.0009
5alpha-pregnane-3alpha,20alpha-diol
wild-type, pH 7.4, 25°C
0.001
5beta-pregnan-20alpha-ol-3-one
-
pH 7.0, 25°C
0.0013
5beta-pregnan-20alpha-ol-3-one
-
pH 7.0, 25°C
0.0057
5beta-pregnan-20alpha-ol-3-one
-
at pH 7.4 and 37°C
0.073
5beta-pregnan-20alpha-ol-3-one
-
-
0.001
5beta-Pregnan-3alpha-ol-20-one
-
at pH 7.4 and 37°C
0.0033
5beta-Pregnan-3alpha-ol-20-one
-
pH 7.0, 25°C
0.0045
5beta-Pregnan-3alpha-ol-20-one
-
pH 7.0, 25°C
0.0045
5beta-Pregnan-3alpha-ol-20-one
wild-type, pH 7.4, 25°C
0.0062
5beta-Pregnan-3alpha-ol-20-one
mutant L308V, pH 7.4, 25°C
0.02 - 0.022
acetoacetyl-CoA
-
-
0.02 - 0.022
acetoacetyl-CoA
-
-
0.162
acetoin
-
at pH 7.4 and 37°C
0.186 - 0.272
acetoin
-
-
0.008
benzyl acetoacetate
-
-
0.008
benzyl acetoacetate
-
-
2.02 - 2.9
cis-benzene-1,2-dihydrodiol
-
racemic
2.9
cis-benzene-1,2-dihydrodiol
-
racemic
0.02407
cortisol
pH 5.0, temperature not specified in the publication
0.032
cortisol
-
NADH, pH 6.3
0.3 - 0.464
D-glyceraldehyde
-
-
0.464
D-glyceraldehyde
-
-
0.67
D-glyceraldehyde
-
-
0.534 - 0.587
D-Lactaldehyde
-
-
0.069
dihydrotestosterone
-
wild type, pH 7.5, 37°C
0.151
dihydrotestosterone
-
mutant R304L, pH 7.5, 37°C
0.852 - 1.3
DL-glyceraldehyde 3-phosphate
-
-
1.3
DL-glyceraldehyde 3-phosphate
-
-
0.012 - 0.015
ethyl 2-methylacetoacetate
-
-
0.012 - 0.015
ethyl 2-methylacetoacetate
-
-
0.222 - 0.447
ethyl 3-oxovalerate
-
-
0.447
ethyl 3-oxovalerate
-
-
0.027
ethyl 4-chloroacetoacetate
-
-
0.027
ethyl 4-chloroacetoacetate
-
-
0.02 - 0.032
ethyl acetoacetate
-
-
0.02 - 0.032
ethyl acetoacetate
-
-
0.067
ethyl acetoacetate
-
-
20
ethyl acetoacetate
-
+/-1
0.303 - 0.654
ethyl benzoylacetate
-
-
0.654
ethyl benzoylacetate
-
-
0.025
ethyl pyruvate
-
-
0.0006
isatin
-
at pH 7.4 and 37°C
0.117 - 0.123
methyl acetoacetate
-
-
0.123
methyl acetoacetate
-
-
0.088
methylglyoxal
-
at pH 7.4 and 37°C
0.356 - 0.548
methylglyoxal
-
-
0.356 - 0.548
methylglyoxal
-
-
0.004
n-butyl acetoacetate
-
-
0.004
n-butyl acetoacetate
-
-
0.0015
n-hexyl acetoacetate
-
-
0.0024
n-hexyl acetoacetate
-
-
0.0013
n-octyl acetoacetate
-
-
0.0016
n-octyl acetoacetate
-
-
0.0081
NADH
-
cortisone 0.05 mM
0.75
NADH
-
10 mM cysteine
0.75
NADH
-
freshly thawed enzyme
1.1
NADH
-
10 mM cysteine, at 4°C until activity decreases to half of the initial value
1.1
NADH
-
enzyme solution that has been left standing at 4°C until the activity has decreased to half of the initial value
0.0007
NADP+
-
spectrophotometric, pH 6.8
0.00088
NADP+
-
fluorometric, pH 7.8
0.008
NADP+
-
20-oxo and 20alpha-hydroxy-steroids, pH 7.0
0.0095 - 0.0096
NADP+
-
37°C, 7.5 min
0.012
NADP+
-
+/-0.001, (S)-ethyl 3-hydroxybutyrate
0.025
NADP+
-
0.01-0.1 mM, 6 min
0.0002
NADPH
-
20-oxo and 20alpha-hydroxy-steroids, pH 7.0
0.0002
NADPH
-
wild type, pH 7.5, 37°C
0.00138
NADPH
-
spectrophotometric, pH 6.8
0.002
NADPH
-
+/-0.0001, ethyl acetoacetate
0.0021
NADPH
-
mutant H222S, pH 7.5, 37°C
0.019
NADPH
-
mutant H222S, pH 7.5, 37°C
0.022
NADPH
-
10 mM cysteine, at 4°C until activity decreases to half of the initial value
0.052
NADPH
-
10 mM cysteine
0.43
Phenylglyoxal
-
-
0.447 - 0.591
Phenylglyoxal
-
-
0.0006
progesterone
-
NADPH, intact cells
0.0006
progesterone
-
at pH 7.4 and 37°C
0.0013
progesterone
-
pH 7.0, 25°C
0.0041
progesterone
-
mutant T307V, pH 7.5, 37°C
0.0042
progesterone
-
wild type, pH 7.5, 37°C
0.0046
progesterone
-
mutant D309L, pH 7.5, 37°C
0.00538
progesterone
-
spectrophotometric pH 6.8
0.0056
progesterone
-
mutant Y305F, pH 7.5, 37°C
0.0066
progesterone
-
NADPH, cell homogenate
0.0094
progesterone
-
mutant E127D, pH 7.5, 37°C
0.011
progesterone
-
+/-0.0017
0.0256
progesterone
-
mutant H222S, pH 7.5, 37°C
0.0286
progesterone
-
mutant H222I, pH 7.5, 37°C
0.2833
progesterone
-
mutant R304L, pH 7.5, 37°C
0.049 - 0.051
Pyridine-3-aldehyde
-
-
0.049 - 0.051
Pyridine-3-aldehyde
-
-
0.081
Pyridine-3-aldehyde
-
-
0.945 - 1.06
Pyridine-4-aldehyde
-
-
1.06
Pyridine-4-aldehyde
-
-
50.9 - 79.7
trans-1S,2S-cyclohexanediol
-
-
79.7
trans-1S,2S-cyclohexanediol
-
-
1.6
trans-benzene-1S,2S-dihydrodiol
-
-
1.6
trans-benzene-1S,2S-dihydrodiol
-
-
additional information
additional information
-
kinetics
-
additional information
additional information
-
rapid activity decrease upon homogenization
-
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0.0358
1-phenylcyclopentanecarboxylic acid
pH 6.5, temperature not specified in the publication
0.00134
2',5'-adenosine bisphosphate
-
pH 7.8, 23°C
0.148
2'-adenylic acid
-
pH 7.8, 23°C
0.0172
2-(4-chlorobenzylidene)cyclopentanone
pH 6.5, temperature not specified in the publication
0.0305
2-(4-chlorobenzylidene)cyclopentyl ethyl ether
pH 6.5, temperature not specified in the publication
0.0000007
3',3'',5',5''-tetrabromophenolphthalein
-
binding to NADPH-enzyme complex via ordered bi-bi-mechanism
0.000009
3,5-dibromosalicylic acid
-
-
0.0000059 - 0.0028
3,5-dichlorosalicylic acid
0.000009
3,5-diiodosalicylic acid
-
-
0.000004 - 0.000113
3-bromo-5-phenylsalicylic acid
0.00000085 - 0.00007
3-chloro-5-phenylsalicylic acid
0.00014
3-phenyl-5-bromosalicylic acid
-
-
0.0485
3-phenylcyclopentanecarboxylic acid
pH 6.5, temperature not specified in the publication
0.0000021
4'-butyl-5-chloro-4-hydroxybiphenyl-3-carboxylic acid
wild-type, 25°C, pH not specified in the publication
2.84
5'-adenylic acid
-
pH 7.8, 23°C
0.0000013
5-chloro-4-hydroxy-3'-methylbiphenyl-3-carboxylic acid
wild-type, 25°C, pH not specified in the publication
0.0000026
5-chloro-4-hydroxy-4'-methylbiphenyl-3-carboxylic acid
wild-type, 25°C, pH not specified in the publication
0.00000086
5-chloro-4-hydroxybiphenyl-3-carboxylic acid
wild-type, 25°C, pH not specified in the publication
0.0000013
5-fluoro-4-hydroxybiphenyl-3-carboxylic acid
wild-type, 25°C, pH not specified in the publication
0.021
Acetylsalicylate
-
-
0.00087
adenosine 2'-monophospho- 5'-diphosphoribose
-
pH 7.8, 23°C
0.95
adenosine diphosphoribose
-
pH 7.8, 23°C
0.01
aminopyridine 1,N6-ethenoadenine dinucleotide phosphate
-
pH 7.8, 23°C
0.0029
aminopyridine adenine dinucleotide phosphate
-
pH 7.8, 23°C
0.022
Diazotized 3-aminopyridine 1,N6-ethenoadenine dinucleotide phosphate
-
pH 7.8, 23°C
0.0005
Diazotized 3-aminopyridine adenine dinucleotide phosphate
-
pH 7.8, 23°C
9.29
N-1-butylnicotinamide chloride
-
pH 7.8, 23°C
1.24
N-1-decylnicotinamide chloride
-
pH 7.8, 23°C
8.95
N-1-ethylnicotinamide chloride
-
pH 7.8, 23°C
3.39
N-1-heptylnicotinamide chloride
-
pH 7.8, 23°C
6.59
N-1-hexylnicotinamide chloride
-
pH 7.8, 23°C
0.205 - 14.8
N-1-methylnicotinamide chloride
3.29
N-1-nonylnicotinamide chloride
-
pH 7.8, 23°C
4.01
N-1-octylnicotinamide chloride
-
pH 7.8, 23°C
9.35
N-1-pentylnicotinamide chloride
-
pH 7.8, 23°C
8.24
N-1-propylnicotinamide chloride
-
pH 7.8, 23°C
0.487
N-1-undecylnicotinamide chloride
-
pH 7.8, 23°C
0.00074
NADP+
-
pH 7.8, 23°C
additional information
additional information
-
0.0000059
3,5-dichlorosalicylic acid
wild type enzyme, in 0.1 M potassium phosphate buffer, pH 7.4
0.0000059
3,5-dichlorosalicylic acid
wild-type, 25°C, pH not specified in the publication
0.0000059
3,5-dichlorosalicylic acid
-
wild-type, pH and temperature not specified in the publication
0.0000066
3,5-dichlorosalicylic acid
-
mutant F311A, pH and temperature not specified in the publication
0.000007
3,5-dichlorosalicylic acid
-
mutant F311L, pH and temperature not specified in the publication
0.000078
3,5-dichlorosalicylic acid
mutant L308V, 25°C, pH not specified in the publication
0.000078
3,5-dichlorosalicylic acid
-
mutant L308V, pH and temperature not specified in the publication
0.000085
3,5-dichlorosalicylic acid
-
mutant L54V, pH and temperature not specified in the publication
0.00027
3,5-dichlorosalicylic acid
mutant enzyme L306A, in 0.1 M potassium phosphate buffer, pH 7.4
0.000273
3,5-dichlorosalicylic acid
-
mutant L306A, pH and temperature not specified in the publication
0.00058
3,5-dichlorosalicylic acid
mutant enzyme H222S, in 0.1 M potassium phosphate buffer, pH 7.4
0.00085
3,5-dichlorosalicylic acid
mutant enzyme L54V, in 0.1 M potassium phosphate buffer, pH 7.4
0.00279
3,5-dichlorosalicylic acid
mutant L308A, 25°C, pH not specified in the publication
0.00279
3,5-dichlorosalicylic acid
-
mutant L308V, pH and temperature not specified in the publication
0.0028
3,5-dichlorosalicylic acid
mutant enzyme L308A, in 0.1 M potassium phosphate buffer, pH 7.4
0.000004
3-bromo-5-phenylsalicylic acid
-
-
0.0000041
3-bromo-5-phenylsalicylic acid
wild-type, 25°C, pH not specified in the publication
0.000014
3-bromo-5-phenylsalicylic acid
mutant L308V, 25°C, pH not specified in the publication
0.000113
3-bromo-5-phenylsalicylic acid
mutant L308A, 25°C, pH not specified in the publication
0.00000085
3-chloro-5-phenylsalicylic acid
-
mutant F311L, pH and temperature not specified in the publication
0.00000086
3-chloro-5-phenylsalicylic acid
-
wild-type, pH and temperature not specified in the publication
0.0000012
3-chloro-5-phenylsalicylic acid
-
mutant L308V, pH and temperature not specified in the publication
0.0000015
3-chloro-5-phenylsalicylic acid
-
mutant F311A, pH and temperature not specified in the publication
0.0000017
3-chloro-5-phenylsalicylic acid
-
mutant L308V, pH and temperature not specified in the publication
0.0000048
3-chloro-5-phenylsalicylic acid
-
mutant L54V, pH and temperature not specified in the publication
0.00007
3-chloro-5-phenylsalicylic acid
-
mutant L306A, pH and temperature not specified in the publication
0.205
N-1-methylnicotinamide chloride
-
pH 7.8, 23°C
14.8
N-1-methylnicotinamide chloride
-
pH 7.8, 23°C
additional information
additional information
-
inhibition kinetics
-
additional information
additional information
-
inhibition kinetics
-
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Strickler, R.C.; Tobias, B.; Covey, D.F.
Human placental 17beta-estradiol dehydrogenase and 20alpha-hydroxysteroid dehydrogenase. Two activities at a single enzyme active site
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316-321
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Homo sapiens
brenda
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Rattus norvegicus, Rattus norvegicus Wistar-Imamichi
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Rattus norvegicus
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Homo sapiens
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Kinetic studies of rat ovarian 20alpha-hydroxysteroid dehydrogenase
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51-58
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Rattus norvegicus
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Rattus norvegicus
brenda
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Sus scrofa
brenda
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Sus scrofa
brenda
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20alpha-Hydroxysteroid dehydrogenase of porcine testes
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Sus scrofa
brenda
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Bos taurus
brenda
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Sus scrofa
brenda
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brenda
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Rattus norvegicus
-
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20alpha-hydroxy steroid dehydrogenase of cultured mammalian (HeLa S3) cells
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297
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brenda
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Rattus norvegicus
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Rattus norvegicus
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Expression, crystallization and preliminary X-ray analysis of human and rabbit 20alpha-hydroxysteroid dehydrogenases in complex with NADP(H) and various steroid substrates
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Activity and expression of progesterone metabolizing 5alpha-reductase, 20alpha-hydroxysteroid oxidoreductase and 3alpha(beta)-hydroxysteroid oxidoreductases in tumorigenic (MCF-7, MDA-MB-231, T-47D) and nontumorigenic (MCF-10A) human breast cancer cells
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9
2003
Homo sapiens
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Selective and potent inhibitors of human 20alpha-hydroxysteroid dehydrogenase (AKR1C1) that metabolizes neurosteroids derived from progesterone
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503-513
2003
Homo sapiens
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Couture, J.F.; Legrand, P.; Cantin, L.; Luu-The, V.; Labrie, F.; Breton, R.
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331
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Homo sapiens
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Adrenal 20alpha-hydroxysteroid dehydrogenase in the mouse catabolizes progesterone and 11-deoxycorticosterone and is restricted to the X-zone
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148
976-988
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brenda
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90
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Homo sapiens
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Human chorionic gonadotropin-dependent induction of an equine aldo-keto reductase (AKR1C23) with 20alpha-hydroxysteroid dehydrogenase activity during follicular luteinization in vivo
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36
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2006
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Expression and possible role of 20alpha-hydroxysteroid dehydrogenase in the placenta of the goat
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51
265-272
2005
Capra hircus
brenda
Shimada, H.; Miura, K.; Imamura, Y.
Characteristics and inhibition by flavonoids of 20alpha-hydroxysteroid dehydrogenase activity in mouse tissues
Life Sci.
78
2931-2936
2006
Mus musculus
brenda
Piekorz, R.P.; Gingras, S.; Hoffmeyer, A.; Ihle, J.N.; Weinstein, Y.
Regulation of progesterone levels during pregnancy and parturition by signal transducer and activator of transcription 5 and 20alpha-hydroxysteroid dehydrogenase
Mol. Endocrinol.
19
431-440
2005
Mus musculus
brenda
Shimada, H.; Ohtaguro, M.; Miura, K.; Imamura, Y.
Inhibitory effects of diesel exhaust components and flavonoids on 20alpha-hydroxysteroid dehydrogenase activity in mouse tissues
J. Enzyme Inhib. Med. Chem.
22
445-449
2007
Mus musculus
brenda
Nio, J.; Iwanaga, T.
Galectins in the mouse ovary: concomitant expression of galectin-3 and progesterone degradation enzyme (20alpha-HSD) in the corpus luteum
J. Histochem. Cytochem.
55
423-432
2007
Mus musculus (Q8K023), Mus musculus
brenda
Ishida, M.; Choi, J.H.; Hirabayashi, K.; Matsuwaki, T.; Suzuki, M.; Yamanouchi, K.; Horai, R.; Sudo, K.; Iwakura, Y.; Nishihara, M.
Reproductive phenotypes in mice with targeted disruption of the 20alpha-hydroxysteroid dehydrogenase gene
J. Reprod. Dev.
53
499-508
2007
Mus musculus
brenda
Imamura, Y.; Ohtaguro, M.; Shimada, H.
Several distinct enzymes catalyze 20alpha-hydroxysteroid dehydrogenase activity in mouse liver and kidney
J. Steroid Biochem. Mol. Biol.
107
120-126
2007
Mus musculus
brenda
Dhagat, U.; Carbone, V.; Chung, R.P.; Matsunaga, T.; Endo, S.; Hara, A.; El-Kabbani, O.
A salicylic acid-based analogue discovered from virtual screening as a potent inhibitor of human 20alpha-hydroxysteroid dehydrogenase
Med. Chem.
3
546-550
2007
Homo sapiens
brenda
Dhagat, U.; Endo, S.; Sumii, R.; Hara, A.; El-Kabbani, O.
Selectivity determinants of inhibitor binding to human 20alpha-hydroxysteroid dehydrogenase: crystal structure of the enzyme in ternary complex with coenzyme and the potent inhibitor 3,5-dichlorosalicylic acid
J. Med. Chem.
51
4844-4848
2008
Homo sapiens (Q04828), Homo sapiens
brenda
El-Kabbani, O.; Scammells, P.J.; Gosling, J.; Dhagat, U.; Endo, S.; Matsunaga, T.; Soda, M.; Hara, A.
Structure-guided design, synthesis, and evaluation of salicylic acid-based inhibitors targeting a selectivity pocket in the active site of human 20alpha-hydroxysteroid dehydrogenase (AKR1C1)
J. Med. Chem.
52
3259-3264
2009
Homo sapiens
brenda
Choi, J.H.; Ishida, M.; Matsuwaki, T.; Yamanouchi, K.; Nishihara, M.
Involvement of 20alpha-hydroxysteroid dehydrogenase in the maintenance of pregnancy in mice
J. Reprod. Dev.
54
408-412
2008
Mus musculus
brenda
Smuc, T.; Rizner, T.L.
Aberrant pre-receptor regulation of estrogen and progesterone action in endometrial cancer
Mol. Cell. Endocrinol.
301
74-82
2009
Homo sapiens
brenda
Dhagat, U.; Endo, S.; Soda, M.; Hara, A.; El-Kabbani, O.
Factorizing the role of a critical leucine residue in the binding of substrate to human 20alpha-hydroxysteroid dehydrogenase (AKR1C1): molecular modeling and kinetic studies of the Leu308Val mutant enzyme
Bioorg. Med. Chem. Lett.
20
5274-5276
2010
Homo sapiens (Q04828), Homo sapiens
brenda
Stefane, B.; Brozic, P.; Vehovc, M.; Rizner, T.L.; Gobec, S.
New cyclopentane derivatives as inhibitors of steroid metabolizing enzymes AKR1C1 and AKR1C3
Eur. J. Med. Chem.
44
2563-2571
2009
Homo sapiens (Q04828)
brenda
El-Kabbani, O.; Scammells, P.J.; Day, T.; Dhagat, U.; Endo, S.; Matsunaga, T.; Soda, M.; Hara, A.
Structure-based optimization and biological evaluation of human 20alpha-hydroxysteroid dehydrogenase (AKR1C1) salicylic acid-based inhibitors
Eur. J. Med. Chem.
45
5309-5317
2010
Homo sapiens (Q04828), Homo sapiens
brenda
Naumann, J.M.; Zoellner, A.; Dragan, C.A.; Messinger, J.; Adam, J.; Bureik, M.
Biotechnological production of 20-alpha-dihydrodydrogesterone at pilot scale
Appl. Biochem. Biotechnol.
165
190-203
2011
Homo sapiens
brenda
El-Kabbani, O.; Dhagat, U.; Soda, M.; Endo, S.; Matsunaga, T.; Hara, A.
Probing the inhibitor selectivity pocket of human 20alpha-hydroxysteroid dehydrogenase (AKR1C1) with X-ray crystallography and site-directed mutagenesis
Bioorg. Med. Chem. Lett.
21
2564-2567
2011
Homo sapiens
brenda
Naumann, J.M.; Messinger, J.; Bureik, M.
Human 20alpha-hydroxysteroid dehydrogenase (AKR1C1)-dependent biotransformation with recombinant fission yeast Schizosaccharomyces pombe
J. Biotechnol.
150
161-170
2010
Homo sapiens
brenda
Nanjidsuren, T.; Naidansuren, P.; Park, C.W.; Park, J.J.; Yun, S.J.; Sim, B.W.; Kang, M.H.; Lee, S.R.; Chang, K.T.; Min, K.S.
Expression and localization of the 20alpha-hydroxysteroid dehydrogenase (HSD) enzyme in the reproductive tissues of the cynomolgus monkey Macaca fascicularis
J. Steroid Biochem. Mol. Biol.
127
337-344
2011
Macaca fascicularis
brenda
Naidansuren, P.; Park, C.W.; Kim, S.H.; Nanjidsuren, T.; Park, J.J.; Yun, S.J.; Sim, B.W.; Hwang, S.; Kang, M.H.; Ryu, B.Y.; Hwang, S.Y.; Yoon, J.T.; Yamanouchi, K.; Min, K.S.
Molecular characterization of bovine placental and ovarian 20alpha-hydroxysteroid dehydrogenase
Reproduction
142
723-731
2011
Bos taurus
brenda
Kim, S.; Shin, Y.; Kang, M.; Yoon, J.; Min, K.
Gene expression and localization of 20alpha-hydroxysteroid dehydrogenase (HSD) in reproductive tissues during early pregnancy of cattle
Anim. Reprod. Sci.
147
1-9
2014
Bos taurus, Bos taurus (D0VDT4)
brenda
Papp, E.; Balogun, K.; Banko, N.; Mohammadi, H.; Loutfy, M.; Yudin, M.; Shah, R.; Macgillivray, J.; Murphy, K.; Walmsley, S.; Silverman, M.; Serghides, L.
Low prolactin and high 20-alpha-hydroxysteroid dehydrogenase levels contribute to lower progesterone levels in hiv-infected pregnant women exposed to protease inhibitor-based combination antiretroviral therapy
J. Infect. Dis.
213
1532-1540
2016
Homo sapiens
brenda
Nanjidsuren, T.; Yun, S.J.; Park, C.W.; Kim, M.S.; Kang, M.H.; Min, K.S.
Expression and localization of 20alpha-hydroxysteroid dehydrogenase (20lpha-HSD) in porcine reproductive tissues during pregnancy
Anim. Reprod. Sci.
148
63-71
2014
Sus scrofa
brenda
Matsunaga, T.; Yamaguchi, A.; Morikawa, Y.; Kezuka, C.; Takazawa, H.; Endo, S.; El-Kabbani, O.; Tajima, K.; Ikari, A.; Hara, A.
Induction of aldo-keto reductases (AKR1C1 and AKR1C3) abolishes the efficacy of daunorubicin chemotherapy for leukemic U937 cells
Anticancer Drugs
25
868-877
2014
Homo sapiens (Q04828), Homo sapiens
brenda
Endo, S.; Arai, Y.; Hara, A.; Kitade, Y.; Bunai, Y.; El-Kabbani, O.; Matsunaga, T.
Substrate specificity and inhibitor sensitivity of rabbit 20alpha-hydroxysteroid dehydrogenase
Biol. Pharm. Bull.
36
1514-1518
2013
Oryctolagus cuniculus
brenda
Kwon, S.; Bang, W.; Jeong, J.; Cho, H.; Park, D.; Hwang, J.; Kim, T.; Ko, M.; Cho, I.; Joo, Y.; Jeong, M.; Kim, S.; Kim, C.
Important role of the C-terminal region of pig aldo-keto reductase family 1 member C1 in the NADPH-dependent reduction of steroid hormones
Indian J. Biochem. Biophys.
50
237-241
2013
Sus scrofa
brenda
Sudeshna, T.; Anand, K.; Medhamurthy, R.
Analysis of 20alpha-hydroxysteroid dehydrogenase expression in the corpus luteum of the buffalo cow: effect of prostaglandin F2-alpha treatment on circulating 20alpha-hydroxyprogesterone levels
Reprod. Biol. Endocrinol.
11
111
2013
Bos taurus
brenda
Rantala, M.H.; Mutikainen, M.; Schuler, G.; Katila, T.; Taponen, J.
Endometrial expression of progesterone, estrogen, and oxytocin receptors and of 20alpha-hydroxysteroid dehydrogenase and cyclooxygenase II 2 and 5 days after ovulation in induced short and normal estrous cycles in dairy cows
Theriogenology
81
1181-1188
2014
Bos taurus
brenda
Yoo, M.H.; Park, C.W.; Byambaragchaa, M.; Kang, M.H.; Min, K.S.
Data on the localization of EGFP and 20alpha-hydroxysteroid dehydrogenase (20alpha-HSD) in the placenta and testes of transgenic mice
Data Brief
19
632-637
2018
Mus musculus (Q8K023)
brenda
Giatti, S.; Diviccaro, S.; Falvo, E.; Garcia-Segura, L.; Melcangi, R.
Physiopathological role of the enzymatic complex 5alpha-reductase and 3alpha/beta-hydroxysteroid oxidoreductase in the generation of progesterone and testosterone neuroactive metabolites
Front. Neuroendocrinol.
57
100836
2020
Rattus norvegicus, Homo sapiens (Q04828), Mus musculus (Q91WT7)
brenda
Doden, H.; Pollet, R.; Mythen, S.; Wawrzak, Z.; Devendran, S.; Cann, I.; Koropatkin, N.; Ridlon, J.
Structural and biochemical characterization of 20-hydroxysteroid dehydrogenase from Bifidobacterium adolescentis strain L2-32
J. Biol. Chem.
294
12040-12053
2019
Bifidobacterium adolescentis (A7A7R9), Bifidobacterium adolescentis L2-32 (A7A7R9)
brenda