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1.1.1.25: shikimate dehydrogenase (NADP+)

This is an abbreviated version!
For detailed information about shikimate dehydrogenase (NADP+), go to the full flat file.

Word Map on EC 1.1.1.25

Reaction

shikimate
+
NADP+
=
3-dehydroshikimate
+
NADPH
+
H+

Synonyms

3-dehydroquinate dehydratase/shikimate dehydrogenase, 5-dehydroshikimate reductase, 5-dehydroshikimic reductase, ael1, Af2327, AroE, bifunctional dehydroquinate dehydratase-shikimate dehydrogenase, bifunctional DHQD-SDH/QDH, cgR_0495, cgR_1677, ChlreSDH, CsDQD/SDH, dehydroquinate dehydratase-shikimate dehydrogenase, dehydroquinate dehydratase/shikimate dehydrogenase, dehydroshikimic reductase, DHD/SHD, DHQ-SDH, DHQD-SDH, DHS reductase, DQD/SDH, EcDQD, EcDQD/SDH, EcDQD/SDH1, EcDQD/SDH2, EcDQD/SDH3, EcoSDH, EcSDH, EMB3004, HI0607, HpSDH, More, MtbSD, MtbSDH, NAD+-dependent enzyme quinate/shikimate dehydrogenase, NADP-dependent shikimate dehydrogenase, NADP-shikimate dehydrogenase, PgSDH, PhypaSDH, PintaSDH, Poptr1, Poptr5, PoptrSDH1, QDH/SDH, qsuD, quinate/shikimate dehydrogenase, RhobaSDH, rifI, SaSDH, SD, SDH, sdhL, SelmoSDH, ShDH, shikimate 5-dehydrogenase, shikimate dehydrogenase, shikimate oxidoreductase, shikimate:NADP oxidoreductase, shikimate:NADP+ 5-oxidoreductase, shikimate:NADP+ oxidoreductase, SKDH, TgSDH, tm0346, VvSDH1, VvSDH2, VvSDH3, VvSDH4, YdiB

ECTree

     1 Oxidoreductases
         1.1 Acting on the CH-OH group of donors
             1.1.1 With NAD+ or NADP+ as acceptor
                1.1.1.25 shikimate dehydrogenase (NADP+)

Inhibitors

Inhibitors on EC 1.1.1.25 - shikimate dehydrogenase (NADP+)

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INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
(3E)-3-[2-(4-bromophenyl)hydrazinylidene]piperidine-2,4,6-trione
-
(3R,3'R,4S,4'S,5R,5'R)-N,N'-(butane-1,4-diyl)bis(3,4,5-trihydroxycyclohex-1-ene-1-carboxamide)
-
(3R,3'R,4S,4'S,5R,5'R)-N,N'-(ethane-1,2-diyl)bis(3,4,5-trihydroxycyclohex-1-ene-1-carboxamide)
-
(3R,3'R,4S,4'S,5R,5'R)-N,N'-(propane-1,3-diyl)bis(3,4,5-trihydroxycyclohex-1-ene-1-carboxamide)
-
(3R,4S,5R)-3,4,5-trihydroxy-N-(3-hydroxypropyl)cyclohex-1-ene-1-carboxamide
-
(3R,4S,5R)-3,4,5-trihydroxy-N-(4-hydroxybutyl)cyclohex-1-ene-1-carboxamide
-
(3R,4S,5R)-3,4,5-trihydroxy-N-(5-hydroxypentyl)cyclohex-1-ene-1-carboxamide
-
(3R,4S,5R)-3,4,5-trihydroxy-N-(6-hydroxyhexyl)cyclohex-1-ene-1-carboxamide
-
(3R,4S,5R)-3,4,5-tri[(tert-butyldimethylsilyl)oxy]cyclohex-1-enecarboxylic acid
-
(4Z)-4-[2-(3-hydroxyphenyl)triazan-1-ylidene]-5-methyl-2-[(piperidin-1-yl)methyl]-2,4-dihydro-3H-pyrazol-3-one
-
(azepan-1-yl)(3-methyl-4,5-dinitrophenyl)methanone
-
1,2,4-triazolo[3,4-b][1,3,4]thiadiazole
-
half-maximal inhibition at 0.023 mg/ml
1,3-benzodioxole-5-carbothioamide
-
the compound shows higher affinity for the shikimate binding site than for the NADP+ binding site, mixed full inhibition mechanism versus shikimate, non-competitive full inhibition mechanism versus NADP+, interaction analysis and enzyme-bound structure, overview. 75% inhibition at 0.4 mM
2,2'-bithiophene-5-carboxylic acid
-
the inhibitor is identified by virtual screeening, 87% inhibition at 0.2 mM, competitive versus shikimate, uncompetitive versus NADP+. Flexible docking studies reveal that the inhibitor molecule makes interactions with catalytic residues
2,2-bisepigallocatechin gallate
about 50% inhibition at 0.0025 mM
2,4-Dichlorophenoxyacetic acid
-
-
2,5-dimethyl-1,4-phenylene bis(trifluoroacetate)
-
2-(3,4-dihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3,5,7-triol
-
2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxo-4H-1-benzopyran-3-yl 6-deoxy-alpha-L-mannopyranoside
-
2-(3,4-dihydroxyphenyl)ethyl 6-O-[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]-beta-D-glucopyranoside
-
2-([2-([2-([2-(2,3-dimethylanilino)-2-oxoethyl]sulfanyl)-1,3-benzothiazol-6-yl]amino)2-oxoethyl]sulfanyl)-N-(2-naphthyl)acetamide
IC50: 0.0029 mM, competitive inhibition with respect to shikimate, noncompetitive to NADP+, potent antibacterial activity
2-[4-(trifluoromethyl)phenyl]-1,3-thiazole-4-carboxylic acid
2-[methyl[3-(trifluoromethyl)naphthalen-1-yl]amino]ethan-1-ol
3,3,3-trifluoro-N-(2-nitrophenyl)-2-(trifluoromethyl)propanamide
-
3,5,7-trihydroxy-3'-(4-hydroxy-3-methoxyphenyl)-2'-(hydroxymethyl)-2,3,3',4'-tetrahydro-2'H,4H-[2,6'-bi-1-benzopyran]-4-one
-
3,5-dihydroxy-4-methylbenzoic acid
-
3,5-Dihydroxybenzoate
-
moderate
3-(2-naphthyloxy)-4-oxo-2-(trifluoromethyl)-4H-chromen-7-yl 3-chlorobenzoate
IC50: 0.0039 mM, noncompetitive inhibition with respect to shikimate, competitive to NADP+
3-(3,4-dihydroxyphenyl)-2-[[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy]propanoic acid
-
3-(3-fluoropyridin-4-yl)-6-(phenoxymethyl)-1,2,4-triazolo[3,4-b]-1,3,4-thiadiazole
-
-
3-(4-bromophenyl)-6-((2,4-dichlorophenoxy)methyl)-[1,2,4]-triazolo[3,4-b][1,3,4]thiadiazole
-
half-maximal inhibition at 0.0396 mg/ml
3-(4-bromophenyl)-6-((2-methyl-4-chlorophenoxy)methyl)-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazole
-
half-maximal inhibition at 0.0216 mg/ml
3-(4-bromophenyl)-6-((4-chlorophenoxy)methyl)-[1,2,4]triazolo-[3,4-b][1,3,4]thiadiazole
-
half-maximal inhibition at 0.0363 mg/ml
3-(4-bromophenyl)-6-((4-fluorophenoxy)methyl)-[1,2,4]triazolo-[3,4-b][1,3,4]thiadiazole
-
half-maximal inhibition at 0.0795 mg/ml
3-(4-bromophenyl)-6-((4-methoxyphenoxy)methyl)-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazole
-
half-maximal inhibition at 0.0120 mg/ml
3-(4-bromophenyl)-6-((4-nitrophenoxy)methyl)-[1,2,4]triazolo-[3,4-b][1,3,4]thiadiazole
-
half-maximal inhibition at 0.0586 mg/ml
3-(4-chlorophenyl)-6-((2-naphthyloxy)methyl)-[1,2,4]triazolo-[3,4-b][1,3,4]thiadiazole
-
half-maximal inhibition at 0.168 mg/ml
3-(4-chlorophenyl)-6-((4-fluorophenoxy)methyl)-[1,2,4]triazolo-[3,4-b][1,3,4]thiadiazole
-
half-maximal inhibition at 5.052 mg/ml
3-(4-chlorophenyl)-6-((4-nitrophenoxy)methyl)-[1,2,4]triazolo-[3,4-b][1,3,4]thiadiazole
-
half-maximal inhibition at 0.00937 mg/ml
3-(4-fluorophenyl)-6-((2-naphthyloxy)methyl)-[1,2,4]triazolo-[3,4-b][1,3,4]thiadiazole
-
-
3-(4-fluorophenyl)-6-((4-methoxyphenoxy)methyl)-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazole
-
half-maximal inhibition at 0.0663 mg/ml
3-(4-hydroxyphenyl)-4-oxo-4H-1-benzopyran-7-yl hexopyranosiduronic acid
-
3-(beta-naphthylmethyl)-6-((4-nitrophenoxy)methyl)-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazole
-
half-maximal inhibition at 0.0407 mg/ml
3-ethyl-3,4-dihydro-2H-1-benzopyran
3-hydroxy-4-(methoxycarbonyl)-2,5-dimethylphenyl 3-formyl-2,4-dihydroxy-6-methylbenzoate
-
3-[[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy]-1,4,5-trihydroxycyclohexane-1-carboxylic acid
-
4,4'-methylenebis(2,6-dibromo-3,5-dihydroxybenzoic acid)
-
4-hydroxy-6-methyl-2-oxo-1-(2-phenylethyl)-1,2-dihydropyridine-3-carbaldehyde
-
4-[(morpholin-4-yl)methyl]benzoic acid
4-[[(E)-(2-ethoxy-6-methyl-4-oxo-2H-1-benzopyran-3(4H)-ylidene)methyl]amino]-2-hydroxybenzoic acid
-
5-(6-hydroxy-1-benzofuran-2-yl)-2-[(1E)-3-methylbut-1-en-1-yl]benzene-1,3-diol
-
5-(hex-1-yn-1-yl)furan-2-carboxylic acid
5-[4-(1H-imidazol-2-ylcarbonyl)phenyl]thiophene-2-carboxylic acid
-
the compound shows higher affinity for the shikimate binding site than for the NADP+ binding site, uncompetitive full inhibition versus shikimate and mixed full inhibition versus NADP+, interaction analysis and enzyme-bound structure, overview. 98% inhibition at 0.4 mM
5-[[5-(4-chlorophenyl)furan-2-yl]methylidene]-2,2-dimethyl-1,3-dioxane-4,6-dione
-
6-((2,4-dichlorophenoxy)methyl)-3-(3-fluoropyridin-4-yl)-[1,2,4]-triazolo[3,4-b][1,3,4]thiadiazole
-
-
6-((4-bromophenoxy)methyl)-3-(4-bromophenyl)-[1,2,4]triazolo-[3,4-b][1,3,4]thiadiazole
-
half-maximal inhibition at 0.0144 mg/ml
6-((4-bromophenoxy)methyl)-3-(4-chlorophenyl)-[1,2,4]triazolo-[3,4-b][1,3,4]thiadiazole
-
half-maximal inhibition at 0.00682 mg/ml
6-((4-fluorophenoxy)methyl)-3-(beta-naphthylmethyl)-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazole
-
half-maximal inhibition at 0.0277 mg/ml
6-(2,6-dichlorophenoxy) pyridin-3-amine
-
60% inhibition at 0.4 mM
6-amino-1,2,3,4-tetrahydronaphthalen-1-one
-
the compound presents a higher affinity for NADP+ binding site than for shikimate binding, mixed partial inhibition mechanism versus NADP+ and mixed full versus shikimate, interaction analysis and enzyme-bound structure, overview. 91% inhibition at 0.4 m
6-hydroxy-1-benzofuran-3(2H)-one
-
-
6-hydroxy-2,3-dihydrobenzo[b]furan-3-one
-
the inhibitor is identified by virtual screeening, 99% inhibition at 0.2 mM, mixed-type inhibition versus shikimate, uncompetitive versus NADP+. Flexible docking studies reveal that the inhibitor molecule makes interactions with catalytic residues
6-hydroxy-7-methyl-1-benzofuran-3(2H)-one
-
mixed partial inhibition mechanism versus NADP+ and shikimate, interaction analysis and enzyme bound structure, overview. 98% inhibition at 0.4 mM
7-hydroxy-2,2,8-trimethyl-2,3-dihydro-4H-1-benzopyran-4-one
-
-
7-hydroxy-2,2,8-trimethyl-2,3-dihydro-4H-chromen-4-one
-
the inhibitor is identified by virtual screeening, 87% inhibition at 0.2 mM, competitive versus shikimate, uncompetitive versus NADP+. Flexible docking studies reveal that the inhibitor molecule makes interactions with catalytic residues
ajmalicine
-
(19alpha)-16,17-didehydro-19-methyloxayohimban-16-carboxylic acid methyl ester, from Rauwolfia serpentina leaves and roots, interacting residues are Asp131 and Arg130
arsenite
-
-
aurintricarboxylic acid
lower inhibitry potency, about 25% inhibition at 0.0025 mM
baicalein
about 25% inhibition at 0.0025 mM
butyl 2-([3-(2-naphthyloxy)4-oxo-2-(trifluoromethyl)4H-chromen-7-yl]oxy)propanoate
IC50: 0.0134 mM, noncompetitive inhibition with respect to shikimate, competitive to NADP+, potent antibacterial activity
cardiolipin
lower inhibitry potency, about 25% inhibition at 0.0025 mM
Cd2+
-
500 nM
curcumin
cyclopropyl(5-hydroxy-1-benzofuran-3-yl)methanone
-
32% inhibition at 0.4 mM
dianthrol
about 50% inhibition at 0.0025 mM
-
diethylenetriamine pentaacetic acid
lower inhibitry potency, about 25% inhibition at 0.0025 mM
ebselen
lower inhibitry potency, about 25% inhibition at 0.0025 mM
ellagic acid
about 50% inhibition at 0.0025 mM
epicatechin gallate
epigallocatechin gallate
epigallocatechin-3,5-digallate
about 50% inhibition at 0.0025 mM
epitheaflavin monogallate
about 50% inhibition at 0.0025 mM
ethyl 5-(1H-pyrazol-3-yl)thiophene-2-carboxylate
-
28% inhibition at 0.4 mM
guaiacol
-
-
HgCl2
-
complete inhibition at concentration 0.05 mM
hydroquinone
lower inhibitry potency, about 25% inhibition at 0.0025 mM
iodoacetate
limonin
-
7,16-dioxo-7,16-dideoxylimondiol, from Citrus sp. fruits, interacting residues are Thr75, Thr78, Val71, Gln101, and Pro103
maesaquinone diacetate
IC50: 0.0035 mM, noncompetitive inhibition with respect to shikimate and NADP+
merbromin
lower inhibitry potency, about 25% inhibition at 0.0025 mM
Metal ions
-
-
-
methyl 3-hydroxy-1-benzothiophene-2-carboxylate
N-ethylmaleimide
-
-
N-methyl-N-(quinolin-6-ylmethyl)amine
-
63% inhibition at 0.4 mM
N-[2,2-dimethyl-6-(1-methyldioxidan-1-ium-1-yl)-3,4-dihydro-2H-1-benzopyran-4-yl]-N2-methyl-N2-[(pyridin-2-yl)methyl]glycinamide
-
34% inhibition at 0.4 mM
NADP+
product inhibition, competitive versus NADPH, noncompetitive versus 3-dehydroshikimate
nordihydroguaiaretic acid
lower inhibitry potency, about 25% inhibition at 0.0025 mM
p-chloromercuribenzoate
p-hydroxymercuribenzoate
-
moderate
protocatechuic acid
purpurogallin
about 50% inhibition at 0.0025 mM
pyridoxine
lower inhibitry potency, about 25% inhibition at 0.0025 mM
pyrogallin
about 50% inhibition at 0.0025 mM
quercetin
about 25% inhibition at 0.0025 mM
SDS
-
nearly complete inactivation of AroE at 0.02%
shikimate
strictamin
-
akuammilan-17-oic acid methyl ester, from Alstonia scholaris leaves, interacting residues are Tyr129, Gln126, and Leu125
taxifolin
about 25% inhibition at 0.0025 mM
theaflavanin
about 25% inhibition at 0.0025 mM
theaflavin monogallate
about 50% inhibition at 0.0025 mM
theaflavin-3,3-digallate
about 25% inhibition at 0.0025 mM
[2,2'-bithiophene]-5-carboxylic acid
-
-
[2-[2-(dimethylamino)ethoxy]phenyl]methanol
[4-(4-methylperhydro-1,4-diazepin-1-yl)phenyl]methanol
-
67% inhibition at 0.4 mM
additional information
-