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1,4-benzoquinone + NAD(P)H + H+
1,4-benzoquinol + NAD(P)+
1,4-benzoquinone + NADH + H+
1,4-benzoquinol + NAD+
1,4-benzoquinone + NADPH
1,4-benzosemiquinone + NADP+
-
-
-
-
?
1,4-dimethoxymethylbenzoquinone + NAD(P)H
1,4-dimethoxymethylhydrobenzoquinone + NAD(P)+
-
-
-
?
1,4-naphthoquinone + NAD(P)H
1,4-naphthohydroquinone + NAD(P)+
1,4-naphthoquinone + NADPH + H+
1,4-naphthoquinol + NADP+
-
-
-
-
?
1,4-naphthoquinone + NADPH + H+
1,4-naphthosemiquinone + NADP+
-
-
-
-
?
1,4-tetramethylbenzoquinone + NAD(P)H
1,4-tetramethylhydrobenzoquinone + NAD(P)+
-
-
-
?
1,8-dihydroxy-9,10-anthraquinone + NADPH
1,8-dihydroxy-9,10-anthraquinol + NADP+
-
-
-
-
?
1-hydroxy-2-[2-(nitrooxy)ethyl]-1-oxo-2-(2,4,6-trinitro-3-(nitro[2-(nitrooxy)ethyl]amino)phenyl)diazanium + NAD(P)H + H+
reduced 1-hydroxy-2-[2-(nitrooxy)ethyl]-1-oxo-2-(2,4,6-trinitro-3-(nitro[2-(nitrooxy)ethyl]amino)phenyl)diazanium + NAD(P)+
-
-
ratio kcat to Km value is 52000 per M and s
-
?
1-hydroxy-9,10-anthraquinone + NADPH
1-hydroxy-9,10-anthraquinol + NADP+
-
-
-
-
?
17-(2-dimethylylamino)ethylamino-17-demethoxygeldanamycin + NAD(P)H + H+
reduced 17-(2-dimethylylamino)ethylamino-17-demethoxygeldanamycin + NADP+
-
-
reduced component is a more potent Hsp90 inhibitor than parent benzoquinone ansamycin
-
?
17-(2-pyrrolidin-1-yl)ethylamino-17-demethoxygeldanamycin + NAD(P)H + H+
reduced 17-(2-pyrrolidin-1-yl)ethylamino-17-demethoxygeldanamycin + NADP+
-
-
reduced component is a more potent Hsp90 inhibitor than parent benzoquinone ansamycin
-
?
17-allylamino-17-demethoxygeldanamycin + NAD(P)H + H+
reduced 17-allylamino-17-demethoxygeldanamycin + NADP+
-
-
reduced component is a more potent Hsp90 inhibitor than parent benzoquinone ansamycin
-
?
17-amino-17-demethoxygeldanamycin + NAD(P)H + H+
reduced 17-amino-17-demethoxygeldanamycin + NADP+
-
-
reduced component is a more potent Hsp90 inhibitor than parent benzoquinone ansamycin
-
?
2 ferricyanide + NAD(P)H
2 ferrocyanide + NAD(P)+ + H+
2 ferricyanide + NADH
2 ferrocyanide + NAD+ + H+
-
60% activity compared to the reactions of NADPH or NADH with 2,3-dimethoxy-5-methyl-1,4-benzoquinone
-
-
?
2,3,3-trimethyl-2,3-dihydronaphtho[1,2-b]furan-4,5-dione + NADH + H+
2,3,3-trimethyl-2,3-dihydronaphtho[1,2-b]furan-4,5-diol + NAD+
-
-
-
?
2,3,5,6-tetramethyl-1,4-benzoquinone + NAD(P)H
reduced 2,3,5,6-tetramethyl-1,4-benzoquinone + NAD(P)+
-
-
-
?
2,3-diglutathionyl-1,4-naphthoquinone + NADPH
2,3-diglutathionyl-1,4-naphthoquinol + NADP+
-
-
-
-
?
2,3-dihydroxy-5-methyl-1,4-benzoquinone + NAD(P)H
2,3-dihydroxy-5-methyl-1,4-benzoquinol + NAD(P)+
2,3-dimethyl-1,4-naphthoquinone + NAD(P)H
2,3-dimethyl-1,4-hydronaphthoquinone + NAD(P)+
-
-
-
?
2,4,6-trinitrotoluene + NAD(P)H +
reduced 2,4,6-trinitrotoluene + NAD(P)+
-
-
ratio kcat to Km value is 670 per M and s
-
?
2,5-bis(aziridin-1-yl)-3,6-dimethylcyclohexa-2,5-diene-1,4-dione + NAD(P)H
2,5-bis(aziridin-1-yl)-3,6-dimethylbenzene-1,4-diol + NAD(P)+
excellent substrate
-
-
?
2,5-bis(aziridin-1-yl)-3-(hydroxymethyl)-6-methylcyclohexane-1,4-dione + NAD(P)H
2,5-bis(aziridin-1-yl)-3-(hydroxymethyl)-6-methylbenzene-1,4-diol + NAD(P)+
excellent substrate
-
-
?
2,5-bis(ethylamine)-3,6-diaziridinyl-1,4-benzoquinone + NADPH
2,5-bis(ethylamine)-3,6-diaziridinyl-1,4-benzoquinol + NADP+
-
-
-
-
?
2,5-di-tert-butyl-1,4-benzoquinone + NADH
2,5-di-tert-butyl-1,4-benzoquinol + NAD+
-
-
-
?
2,5-diaziridinyl-1,4-benzoquinone + NADPH
2,5-diaziridinyl-1,4-benzoquinol + NADP+
-
-
-
-
?
2,5-diaziridinyl-3-(hydroxymethyl)-6-methyl-1,4-benzoquinone + NADPH
2,5-diaziridinyl-3-(hydroxymethyl)-6-methyl-1,4-benzoquinol + NADP+
-
-
-
-
?
2,5-dihydroxy-1,4-naphthoquinone + NADPH
2,5-dihydroxy-1,4-naphthoquinol + NADP+
-
-
-
-
?
2,5-dimethoxy-1,3-benzothiazole-4,7-dione + NAD(P)H
2,5-dimethoxy-1,3-benzothiazole-4,7-diol + NAD(P)+
-
-
-
?
2,5-dimethoxy-1-methyl-1H-benzimidazole-4,7-dione + NAD(P)H
2,5-dimethoxy-1-methyl-1H-benzimidazole-4,7-diol + NAD(P)+
-
-
-
?
2,5-dimethyl-1,4-benzoquinone + NADPH
2,5-dimethyl-1,4-benzoquinol + NADP+
-
-
-
-
?
2,5-dimethyl-1,4-naphthoquinone + NADPH
2,5-dimethyl-1,4-naphthoquinol + NADP+
-
-
-
-
?
2,5-dimethyl-3,6-diaziridinyl-1,4-benzoquinone + NADPH
2,5-dimethyl-3,6-diaziridinyl-1,4-benzoquinol + NADP+
-
-
-
-
?
2,6-dichlorophenolindophenol + NADPH
reduced 2,6-dichlorophenolindophenol + NADP+
-
-
-
?
2,6-dimethoxy-1,4-benzoquinone + NADH
2,6-dimethoxy-1,4-benzoquinol + NAD+
-
-
-
?
2,6-dimethoxybenzoquinone + NAD(P)H
2,6-dimethoxyhydrobenzoquinone + NAD(P)+
-
-
-
?
2,6-dimethyl-1,4-benzoquinone + NADPH
2,6-dimethyl-1,4-benzoquinol + NADP+
-
-
-
-
?
2-(1-hydroxyethyl)-5-methoxy-3-methyl-1-benzofuran-4,7-dione + NADH + H+
2-(1-hydroxyethyl)-5-methoxy-3-methyl-1-benzofuran-4,7-diol + NAD+
-
-
-
?
2-acetoxymethyl-6-methoxy-1-methylbenzimidazole-4,7-dione + NADH
? + NAD+
-
-
-
-
?
2-chloro-6-hydroxy-1,4-benzoquinone + NADH
6-chlorobenzene-1,2,4-triol + NAD+
-
-
-
-
?
2-ethyl-1,4-naphthoquinone + NAD(P)H
2-ethyl-1,4-hydronaphthoquinone + NAD(P)+
-
-
-
?
2-hydroxy-1,4-naphthoquinone + NADPH
2-hydroxy-1,4-naphthoquinol + NADP+
-
-
-
-
?
2-hydroxymethyl-5-methoxy-1-methylbenzimidazole-4,7-dione + NADH
? + NAD+
-
-
-
-
?
2-hydroxymethyl-5-methoxy-2,5-cyclohexadiene-1,4-dione + NAD(P)H
2-hydroxymethyl-5-methoxy-2,5-cyclohexadiene-1,4-diol + NAD(P)+
-
-
-
?
2-hydroxymethyl-5-methoxybenzothiazole-4,7-dione + NADH
? + NAD+
-
-
-
-
?
2-hydroxymethyl-6-methoxy-1-methylbenzimidazole-4,7-dione + NADH
? + NAD+
-
-
-
-
?
2-methoxy-1,4-benzoquinone + NADPH
2-methoxy-1,4-benzoquinol + NADP+
-
-
-
?
2-methoxy-2,5-cyclohexadiene-1,4-dione + NAD(P)H
2-methoxy-2,5-cyclohexadiene-1,4-diol + NAD(P)+
-
-
-
?
2-methoxy-5-(methoxymethyl)-2,5-cyclohexadiene + NADH + H+
2-methoxy-5-methoxymethyl-2,5-cyclohexadiene-1,4-diol + NAD+
-
-
-
-
r
2-methoxy-5-(methoxymethyl)-2,5-cyclohexadiene-1,4-dione + NAD(P)H
2-methoxy-5-methoxymethyl-2,5-cyclohexadiene-1,4-diol + NAD(P)+
-
-
-
?
2-methoxyquinone + NAD(P)H
2-methoxyhydroquinone + NAD(P)+
Sporotrichum pulverulentum
-
-
-
?
2-methyl-1,4-benzoquinone + NADPH
2-methyl-1,4-benzoquinol + NADP+
-
-
-
-
?
2-methyl-1,4-naphthoquinone + NAD(P)H
2-methyl-1,4-dihydronaphthoquinone + NAD(P)+
-
-
-
?
2-methyl-1,4-naphthoquinone + NAD(P)H
2-methyl-1,4-naphthoquinol + NAD(P)+
2-methyl-1,4-naphthoquinone + NADH
2-methyl-1,4-naphthoquinol + NAD+
2-methyl-1,4-naphthoquinone + NADPH
2-methyl-1,4-naphthoquinol + NADp+
2-methyl-3-glutathionyl-5-hydroxy-1,4-naphthoquinone + NADPH
2-methyl-3-glutathionyl-5-hydroxy-1,4-naphthoquinol + NADP+
-
-
-
-
?
2-methyl-3-hydroxy-1,4-naphthoquinone + NADPH
2-methyl-3-hydroxy-1,4-naphthoquinol + NADP+
-
-
-
-
?
2-methyl-3-phytyl-1,4-naphthoquinone + NAD(P)H
2-methyl-3-phytyl-1,4-naphthohydroquinone + NAD(P)+
2-methyl-5-aziridinyl-1,4-benzoquinone + NADPH
2-methyl-5-aziridinyl-1,4-benzoquinol + NADP+
-
-
-
-
?
2-methyl-5-hydroxy-1,4-naphthoquinone + NADPH
2-methyl-5-hydroxy-1,4-naphthoquinol + NADP+
-
-
-
-
?
2-[nitro(2,4,6-trinitrophenyl)amino]ethyl nitrate + NAD(P)H +
reduced 2-[nitro(2,4,6-trinitrophenyl)amino]ethyl nitrate + NAD(P)+
-
-
ratio kcat to Km value is 570000 per M and s
-
?
3,4-dihydro-2,2-dimethyl-2H-naphthol[1,2-b]pyran-5,6-dione + NAD(P)H
3,4-dihydro-2,2-dimethyl-2H-naphthol[1,2-b]pyran-5,6-diol + NAD(P)+
-
trivial name beta-lapachone, potent cytotoxic agent against various cancer cell lines
-
?
3-(1-hydroxyethyl)-5-methoxy-2-methyl-1-benzofuran-4,7-dione + NADH + H+
3-(1-hydroxyethyl)-5-methoxy-2-methyl-1-benzofuran-4,7-diol + NAD+
-
-
-
?
3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide + NAD(P)H
reduced 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide + NAD(P)+
3-(hydroxymethyl)-5-methoxy-1-methyl-1H-indazole-4,7-dione + NADH + H+
3-(hydroxymethyl)-5-methoxy-1-methyl-1H-indazole-4,7-diol + NAD+
-
-
-
?
3-(hydroxymethyl)-5-methoxy-1-methyl-2-phenyl-1H-indole-4,7-dione + NAD(P)H
3-(hydroxymethyl)-5-methoxy-1-methyl-2-phenyl-1H-indole-4,7-diol + NAD(P)+
excellent substrate
-
-
?
4,5,6,7-tetranitro-1,3-dihydro-2H-benzimidazol-2-one + NAD(P)H +
reduced 4,5,6,7-tetranitro-1,3-dihydro-2H-benzimidazol-2-one + NAD(P)+
-
-
ratio kcat to Km value is 5000000 per M and s
-
?
4,5,6-trinitro-1,3-dihydro-2H-benzimidazol-2-one + NAD(P)H +
reduced 4,5,6-trinitro-1,3-dihydro-2H-benzimidazol-2-one + NAD(P)+
-
-
ratio kcat to Km value is 26000 per M and s
-
?
4,5-dimethoxy-3,5-cyclohexadiene-1,2-dione
4,5-dimethoxy-3,5-cyclohexadiene-1,2-diol + NAD(P)+
-
-
-
?
5,8-dihydroxy-1,4-naphthoquinone + NADPH
5,8-dihydroxy-1,4-naphthoquinol + NADP+
-
-
-
-
?
5,8-dihydroxynaphthoquinone + NAD(P)H
5,8-dihydroxynaphthohydroquinone + NAD(P)+
-
-
-
?
5-(1-aziridinyl)-3-(hydroxymethyl)-2-(3-hydroxy-1-propenyl)-1-methyl-1H-indole-4,7-dione + NAD(P)H
5-(1-aziridinyl)-3-(hydroxymethyl)-2-(3-hydroxy-1-propenyl)-1-methyl-1H-indole-4,7-diol + NAD(P)+
5-(aziridin-1-yl)-2,4-dinitrobenzamide + NAD(P)H
5-(aziridin-1-yl)-4-hydroxylamino-2-nitrobenzamide + NAD(P)+
5-(aziridin-1-yl)-2,4-dinitrobenzamide + reduced dihydronicotineamide riboside
5-(aziridin-1-yl)-4-hydroxylamino-2-nitrobenzamide + oxidized dihydronicotineamide riboside
5-aziridin-1-yl-2,4-dinitrobenzamide + NAD(P)H + H+
5-aziridin-1-yl-4-(hydroxyamino)-2-nitrobenzamide
-
i.e. CB1954, anticancer prodrug
-
-
?
5-aziridin-1-yl-3-(hydroxymethyl)-2-[(1E)-3-hydroxyprop-1-en-1-yl]-1-methyl-1H-indole-4,7-dione + NAD(P)H
5-aziridin-1-yl-3-(hydroxymethyl)-2-[(1E)-3-hydroxyprop-1-en-1-yl]-1-methyl-1H-indole-4,7-diol + NAD(P)+
-
-
-
?
5-hydroxy-1,4-naphthoquinone + NADPH
5-hydroxy-1,4-naphthosemiquinone + NADP+
-
-
-
-
?
5-methoxy-1,2-dimethyl-3-(hydroxymethyl)indole-4,7-dione + NADH
? + NAD+
is efficiently metabolized by NQO1
-
-
?
5-methoxy-1,2-dimethyl-3-[(phenoxy)methyl]indole-4,7-dione + NADH
? + NAD+
inefficient indolequinone substrate
-
-
?
5-methoxy-2-methylbenzothiazole-4,7-dione + NADH
? + NAD+
-
-
-
-
?
5-methoxy-4,7-dioxo-4,7-dihydro-1-benzothiophene-2-carboxylic acid + NADH + H+
4,7-dihydroxy-5-methoxy-1-benzothiophene-2-carboxylic acid + NAD+
-
-
-
?
6-hydroxydopaminequinone + NAD(P)H
6-hydroxydopaminehydroquinone + NAD(P)+
-
-
-
?
6-hydroxydopaquinone + NAD(P)H
6-hydroxydopahydroquinone + NAD(P)+
-
-
-
?
6-methoxy-1,2-dimethyl-3-(hydroxymethyl)indole-4,7-dione + NADH
? + NAD+
is efficiently metabolized by NQO1
-
-
?
6-methoxy-1,2-dimethyl-3-[(phenoxy)methyl]indole-4,7-dione + NADH
? + NAD+
inefficient indolequinone substrate
-
-
?
6-methoxy-1-methyl-2-(4-nitrophenoxymethyl)benzimidazole-4,7-dione + NADH
? + NAD+
-
-
-
-
?
6-methoxy-1-methylbenzimidazole-4,7-dione + NADH
? + NAD+
-
-
-
-
?
7-N-(2-furoyl)demethyllavendamycin methyl ester + NADH
? + NAD+
poor substrate
-
-
?
7-N-acetyldemethyllavendamycin n-butyl amide + NADH
? + NAD+
good substrate
-
-
?
7-N-acetyldemethyllavendamycin sec-butyl amide + NADH
? + NAD+
poor substrate
-
-
?
8-methoxy-2,3,3-trimethyl-2,3-dihydronaphtho[1,2-b]furan-4,5-dione + NADH + H+
8-methoxy-2,3,3-trimethyl-2,3-dihydronaphtho[1,2-b]furan-4,5-diol + NAD+
-
-
-
?
9,10-anthraquinone-2,6-disulfonate + NADPH
? + NADP+
-
-
-
-
?
9,10-anthraquinone-2-sulfonate + NADPH
? + NADP+
-
-
-
-
?
9,10-phenanthrene quinone + NADPH
9,10-phenanthrene quinol + NADP+
-
-
-
-
?
9-methoxy-2,3,3-trimethyl-2,3-dihydronaphtho[1,2-b]furan-4,5-dione + NADH + H+
9-methoxy-2,3,3-trimethyl-2,3-dihydronaphtho[1,2-b]furan-4,5-diol + NAD+
-
-
-
?
acetaminophen + NAD(P)H + H+
N-acetyl-p-benzoquinone imine + NAD(P)+
-
-
enhanced levels of hepatic enzyme may detoxify N-acetyl-p-benzoquinone imine by reducing it back to acetaminophen
-
r
alpha-tocopherolquinone + NAD(P)H
reduced alpha-tocopherolquinone + NAD(P)+
amodiaquine + NAD+
amodiaquine quinoneimine + NADH + H+
-
-
-
r
amodiaquine quinoneimine + NADH + H+
amodiaquine + NAD+
-
-
-
r
benzoquinone + 2 NAD(P)H + H+
benzohydroquinone + 2 NAD(P)+
benzo[a]pyrene 3,6-quinone + NAD(P)H
benzo[a]pyrene 3,6-quinol
-
-
-
?
beta-lapachone + NAD(P)H
reduced beta-lapachone + NAD(P)+
-
-
-
?
chromate(IV) + H2O
chromate(III) + H2O2
chromate(VI) + H2O
chromate(III) + H2O2
coenzyme Q0 + NAD(P)H
reduced coenzyme Q0 + NADP+
coenzyme Q1 + NAD(P)H
reduced coenzyme Q1 + NADP+
coenzyme Q1 + NADH
?
-
-
-
-
?
coenzyme Q10 + NAD(P)H
reduced coenzyme Q10 + NAD(P)+
-
-
-
?
cyclized-dopamine o-quinone + NAD(P)H
cyclized-dopamine o-hydroquinone + NADP+
-
-
-
?
cytochrome C + menadione + NADH
? + reduced menadione + NAD+
-
-
-
-
?
deamino-NADH + H+ + 2,3-dimethoxy-5-methyl-1,4-benzoquinone
deamino-NAD+ + 2,3-dimethoxy-5-methyl-1,4-benzoquinol
-
45% activity compared to NADPH or NADH
-
-
?
diethyl [2,5-bis(aziridin-1-yl)-3,6-dioxocyclohexa-1,4-diene-1,4-diyl]biscarbamate + NAD(P)H
diethyl [2,5-bis(aziridin-1-yl)-3,6-dihydroxybenzene-1,4-diyl]biscarbamate + NAD(P)+
-
-
-
?
duroquinone + NAD(P)H
reduced duroquinone + NAD(P)+
-
-
-
?
duroquinone + NADH
?
-
-
-
-
?
duroquinone + NADH
? + NAD+
duroquinone + NADPH
? + NADP+
duroquinone + NADPH
durohydroquinone + NADP+
-
in both normoxic and hyperoxia-exposed cells, enzyme is the dominant duroquinone reductase
-
-
?
ethyl 5-aziridin-1-yl-2,4-dinitrobenzoate + NAD(P)H +
reduced ethyl 5-aziridin-1-yl-2,4-dinitrobenzoate + NAD(P)+
-
-
ratio kcat to Km value is 20000 per M and s
-
?
ferricyanide + FAD + NADH
?
-
-
-
-
?
ferricyanide + FMN + NADH
?
-
-
-
-
?
ferricyanide + NADH + H+
ferrocyanide + NAD+
-
-
-
-
r
geldanamycin + NAD(P)H
reduced geldanamycin + NAD(P)+
excellent substrate
-
-
?
geldanamycin + NAD(P)H + H+
reduced geldanamycin + NADP+
-
-
reduced component is a more potent Hsp90 inhibitor than parent benzoquinone ansamycin
-
?
hydroxy(oxo)(3,6,8-trinitro-9H-carbazol-1-yl)ammonium + NAD(P)H +
reduced 2-[nitro(2,4,6-trinitrophenyl)amino]ethyl nitrate + NAD(P)+
-
-
ratio kcat to Km value is 500000 per M and s
-
?
indolequinones + NAD(P)H
indolehydroquinones + NAD(P)+
-
compounds with electron-withdrawing groups at the indole 3-position are among the best substrates, groups larger than methyl at N-1 are tolerated, compounds with a leaving group at the 3-indolyl methyl position inactivate the enzyme
-
?
juglone + NAD(P)H
dihydrojuglone + NAD(P)+
juglone + NADH
dihydrojuglone + NAD+
juglone + NADPH
dihydrojuglone + NADP+
-
-
-
-
?
K3[Fe(CN)6] + NAD(P)H
K4[Fe(CN)6] + NAD(P)+
lavendamycin beta-hydroxyethyl ester + NADH
? + NAD+
good substrate
-
-
?
menadione + FAD + NADH
?
-
-
-
-
?
menadione + FMN + NADH
?
-
-
-
-
?
menadione + NAD(P)H
reduced menadione + NAD(P)+
menadione + NAD(P)H
reduced menadione + NADP+
-
-
-
-
?
menadione + NADH
reduced menadione + NAD+
menadione + NADH + H+
? + NAD+
-
-
-
?
menadione + NADH + H+
menadiol + NAD+
menadione + NADH + H+
reduced menadione + NAD+
-
-
-
?
menadione + NADPH
reduced menadione + NADP+
-
-
-
-
?
menadione + NADPH + H+
? + NADP+
-
-
-
?
menadione + NADPH + H+
reduced menadione + NADP+
-
-
-
?
menadione + reduced nicotinamide 2-azidoadenine dinucleotide
reduced menadione + oxidized nicotinamide 2-azidoadenine dinucleotide
-
-
-
?
menadione + reduced nicotinamide 8-azidoadenine dinucleotide
reduced menadione + oxidized nicotinamide 8-azidoadenine dinucleotide
-
-
-
?
methoxyquinone + NAD(P)H
methoxyhydroquinone + NAD(P)+
Sporotrichum pulverulentum
-
-
-
?
methyl 5-methoxy-4,7-dioxo-4,7-dihydro-1-benzothiophene-2-carboxylate + NADH + H+
methyl 4,7-dihydroxy-5-methoxy-1-benzothiophene-2-carboxylate + NAD+
-
-
-
?
methyl red + NAD(P)H
reduced methyl red + NAD(P)+
methyl-1,4-benzoquinone + NADPH + H+
methyl-1,4-benzoquinol + NADP+
two-electron mechanism
-
-
?
methylene blue + NAD(P)H
reduced methylene blue + NAD(P)+
-
-
-
?
mitomycin C + NAD(P)H
reduced mitomycin C + NAD(P)+
poor substrate
-
-
?
mitomycin C + NADPH
? + NADP+
-
-
-
-
?
N-desethylamodiaquine + NAD+
N-desethylamodiaquine quinoneimine + NADH + H+
-
-
-
r
N-desethylamodiaquine quinoneimine + NADH + H+
N-desethylamodiaquine + NAD+
-
-
-
r
N-methyl-N,2,4,6-tetranitroaniline + NAD(P)H +
reduced N-methyl-N,2,4,6-tetranitroaniline + NAD(P)+
-
-
ratio kcat to Km value is 260000 per M and s
-
?
N-methyl-N,2,4-trinitroaniline + NAD(P)H +
reduced N-methyl-N,2,4-trinitroaniline + NAD(P)+
-
-
ratio kcat to Km value is 52000 per M and s
-
?
NAD(P)H + H+ + 17-allylamino-demethoxygeldanamycin
NAD(P)+ + reduced 17-allylamino-demethoxygeldanamycin
-
-
product exhibits superior Hsp90 inhibition and is involved in Hsp70 induction and Raf-1 degradation
-
?
NAD(P)H + H+ + 2,5-diaziridinyl-3-hydroxymethyl-6-methyl-1,4-benzoquinone
NAD(P)+ + reduced 2,5-diaziridinyl-3-hydroxymethyl-6-methyl-1,4-benzoquinone
-
i.e. RH1, induction of apoptosis via enzyme-linked formation of alkylating species
-
-
?
NAD(P)H + H+ + 2,5-dimethyl-3,6-diaziridinyl-1,4-benzoquinone
NAD(P)+ + reduced 2,5-dimethyl-3,6-diaziridinyl-1,4-benzoquinone
-
i.e. MeDZQ, induction of apoptosis via enzyme-linked formation of alkylating species
-
-
?
NAD(P)H + H+ + a quinone
NAD(P)+ + a hydroquinone
the enzyme catalyzes a detoxification process. QR1 gene expression is induced in response to xenobiotics, oxidants, heavy metals, UV light, and ionisation radiation. The enzyme is part of an electrophilic-induced and/or oxidative stress-induced cellular defense mechanism that includes the induction of more than two dozen defensive genes
-
-
?
NAD(P)H + H+ + amrubicin
NAD(P)+ + ?
-
-
-
?
NAD(P)H + H+ + amrubicinol
NAD(P)+ + ?
-
-
-
?
NAD(P)H + H+ + oxidized 2,6-dichlorophenolindophenol
NAD(P)+ + reduced 2,6-dichlorophenolindophenol
NAD(P)H + H+ + quinone
NAD(P)+ + hydroquinone
-
-
-
-
?
NADH + decylubiquinone
NAD+ + decylubiquinol
-
-
-
-
?
NADH + H+ + 1-[3,5-dinitro-2-(1,2,3,4-tetrahydronaphthalen-2-yl)phenyl]-1-oxohydrazinium
?
-
-
-
-
?
NADH + H+ + 10-nitro-5,6-dihydrobenzimidazo[2,1-a]isoquinoline 12-oxide
?
-
-
-
-
?
NADH + H+ + 10-nitro-5,6-dihydrobenzimidazo[2,1-a]isoquinoline-8-carboxamide 12-oxide
?
-
-
-
-
?
NADH + H+ + 10-nitro-5,6-dihydrobenzimidazo[2,1-a]isoquinoline-9-carboxamide 12-oxide
?
-
-
-
-
?
NADH + H+ + 17-(allylamino)-17-demethoxygeldanamycin
?
NADH + H+ + 2,10-dinitro-5,6-dihydrobenzimidazo[2,1-a]isoquinoline 12-oxide
?
-
-
-
-
?
NADH + H+ + 2,3-dimethoxy-5-methyl-1,4-benzoquinone
NAD+ + 2,3-dimethoxy-5-methyl-1,4-benzoquinol
NADH + H+ + 2,3-dimethoxy-5-methyl-2,5-cyclohexadiene-1,4-dione
NAD+ + 2,3-dimethoxy-5-methylbenzene-1,4-diol
i.e. ubiquinone-0, UQ-0, a quinone electron acceptor
-
-
r
NADH + H+ + 2,4-dinitro-5-(1,2,3,4-tetrahydronaphthalen-2-yl)benzamide
?
-
-
-
-
?
NADH + H+ + 2,4-dinitro-5-(5-nitro-1,2,3,4-tetrahydronaphthalen-2-yl)benzamide
?
-
-
-
-
?
NADH + H+ + 2,4-dinitro-5-(7-nitro-1,2,3,4-tetrahydronaphthalen-2-yl)benzamide
?
-
-
-
-
?
NADH + H+ + 2,6-dichlorophenolindophenol
NAD+ + reduced 2,6-dichlorophenolindophenol
-
-
-
-
r
NADH + H+ + 2-(2,4,6-trinitrophenyl)-1,2,3,4-tetrahydronaphthalene
?
-
-
-
-
?
NADH + H+ + 2-(2,4-dinitrophenyl)-1,2,3,4-tetrahydronaphthalene
?
-
-
-
-
?
NADH + H+ + 2-(2,4-dinitrophenyl)-5-nitro-1,2,3,4-tetrahydronaphthalene
?
-
-
-
-
?
NADH + H+ + 2-(3,5-dinitropyridin-2-yl)-1,2,3,4-tetrahydroisoquinoline
?
-
-
-
-
?
NADH + H+ + 2-methyl-1,4-naphthoquinone
NAD+ + 2-methyl-1,4-naphthoquinol
-
-
-
-
?
NADH + H+ + 2-[2,4-dinitro-6-(trifluoromethyl)phenyl]-1,2,3,4-tetrahydronaphthalene
?
-
-
-
-
?
NADH + H+ + 2-[2,4-dinitro-6-(trifluoromethyl)phenyl]-5-nitro-1,2,3,4-tetrahydronaphthalene
?
-
-
-
-
?
NADH + H+ + 2-[2,4-dinitro-6-(trifluoromethyl)phenyl]-7-nitro-1,2,3,4-tetrahydronaphthalene
?
-
-
-
-
?
NADH + H+ + 3,5-dinitro-2-(1,2,3,4-tetrahydronaphthalen-2-yl)benzamide
?
-
-
-
-
?
NADH + H+ + 3,5-dinitro-2-(1,2,3,4-tetrahydronaphthalen-2-yl)benzoic acid
?
-
-
-
-
?
NADH + H+ + 3,5-dinitro-2-(7-nitro-1,2,3,4-tetrahydronaphthalen-2-yl)benzoic acid
?
-
-
-
-
?
NADH + H+ + 4,10-dinitro-5,6-dihydrobenzimidazo[2,1-a]isoquinoline 12-oxide
?
-
-
-
-
?
NADH + H+ + 4,10-dinitro-5,6-dihydrobenzimidazo[2,1-a]isoquinoline-9-carboxamide 12-oxide
?
-
-
-
-
?
NADH + H+ + 4,10-dinitro-8-(trifluoromethyl)-5,6-dihydrobenzimidazo[2,1-a]isoquinoline 12-oxide
?
-
-
-
-
?
NADH + H+ + 5,6-dihydro-10-nitropyrido[3'',2'':4',5']imidazo[2',1'-a]isoquinoline 12-oxide
?
-
-
-
-
?
NADH + H+ + 5-(aziridin-1-yl)-2,4-dinitrobenzamide
?
-
i.e. CB-1954
-
-
?
NADH + H+ + a quinone
NAD+ + a hydroquinone
NADH + H+ + atovaquone
NAD+ + reduced atovaquone
-
atovaquone is 2-[4-(4-chlorophenyl)cyclohexyl]-3-hydroxynaphthalene-1,4-dione
-
-
?
NADH + H+ + benzoquinone
NAD+ + benzoquinol
-
-
-
-
?
NADH + H+ + coenzyme Q0
NAD+ + reduced coenzyme Q0
-
-
-
-
?
NADH + H+ + coenzyme Q1
NAD+ + reduced coenzyme Q1
-
-
-
-
?
NADH + H+ + dichlorophenolindophenol
NAD+ + reduced dichlorophenolindophenol
-
-
-
-
?
NADH + H+ + duroquinone
NAD+ + duroquinol
-
-
-
-
?
NADH + H+ + ubiquinone
NAD+ + ubiquinone
-
the enzyme plays an essential role in maintaining a reduced ubiquinone-pool during infection (Plasmodium falciparum is the causative agents of malaria). The enzyme is not only essential to parasite survival in vivo but may also contribute to the severity and outcome of disease. Type II NADH:quinone oxidoreductase the membrane-bound respiratory enzyme differs from the canonical NADH:dehydrogenase (complex I), because it is not involved in the vectorial transfer of protons across membranes. In the electron transport chain of Plasmodium, the canonical multimeric complex I (NADH:dehydrogenase) found in mammalian mitochondria is absent, and, instead, the parasite possesses five quinone-dependent oxidoreductases, namely a type II NADH:quinone oxidoreductase (PfNDH2), a malate: quinone oxidoreductase (MQO), a dihydroorotate dehydrogenase (DHOD), a glycerol-3-phosphate dehydrogenase (G3PDH), and a succinate: quinone oxidoreductase (SDH). These enzymes link cytosolic metabolism to mitochondrial metabolism, generating reducing power (ubiquinol) for the bc1 complex and an aa3-type cytochrome oxidase, enabling proton pumping and energy conservation
-
-
?
NADH + H+ + ubiquinone-0
NAD+ + ubiquinol-0
-
-
-
-
?
NADH + H+ + ubiquinone-1
NAD+ + ubiquinol-1
-
-
-
-
?
NADH + H+ + ubiquinone-10
NAD+ + ubiquinol-10
-
-
-
-
?
NADPH + H+ + 17-(allylamino)-17-demethoxygeldanamycin
?
NADPH + H+ + 2,3-dimethoxy-5-methyl-1,4-benzoquinone
NADP+ + 2,3-dimethoxy-5-methyl-1,4-benzoquinol
-
100% activity
-
-
?
NADPH + H+ + 2-methyl-1,4-naphthoquinone
NADP+ + 2-methyl-1,4-naphthoquinol
-
-
-
-
?
NADPH + H+ + a quinone
NADP+ + a hydroquinone
-
-
-
-
?
NADPH + H+ + benzoquinone
NADP+ + benzoquinol
-
-
-
-
?
NADPH + H+ + duroquinone
NADP+ + duroquinol
-
-
-
-
?
NADPH + H+ + oxidized 2,6-dichlorophenolindophenol
NADP+ + reduced 2,6-dichlorophenolindophenol
NADPH + H+ + quinone
NADP+ + ?
NADPH + H+ + ubiquinone-1
NADP+ + ubiquinol-1
-
-
-
-
?
NADPH + H+ + ubiquinone-10
NADP+ + ubiquinol-10
-
-
-
-
?
naphthoquinone + NADH + H+
naphthoquinol + NAD+
-
-
-
-
r
nitracrine + NAD(P)H +
reduced nitracrine + NAD(P)+
-
-
i.e. N,N-dimethyl-N'-(1-nitro-9,10-dihydroacridin-9-yl)propane-1,3-diamine, ratio kcat to Km value is 1800 per M and s
-
?
oxidized 2,6-dichlorophenolindophenol + NADH + H+
reduced 2,6-dichlorophenolindophenol + NAD+
oxidized 2,6-dichlorophenolindophenol + NADPH + H+
reduced 2,6-dichlorophenolindophenol + NADP+
-
-
-
-
r
oxidized 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium + NADPH + H+
reduced 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium + NADP+
-
-
-
-
r
oxidized dichlorophenol-indophenol + NAD(P)H
reduced dichlorophenol-indophenol + NADP+
oxidized dichlorophenolindophenol + NADH + H+
reduced dichlorophenolindophenol + NAD+
-
-
-
?
oxidized methyl red + reduced dihydronicotinamide riboside + H+
reduced methyl red + oxidized dihydronicotinamide riboside
-
-
-
-
r
p-benzoquinone + NADH
benzohydroquinone + NAD+
-
-
-
-
?
p-benzoquinone + NADPH
p-benzohydroquinone + NADP+
-
-
-
-
?
plumbagin + NADH
? + NAD+
-
-
-
-
?
plumbagin + NADPH
? + NADP+
-
-
-
-
?
potassiumferricyanide + NADH + H+
potassium ferrocyanide + NAD+
-
-
-
-
r
potassiumferricyanide + NADPH + H+
potassium ferrocyanide + NADP+
-
-
-
-
r
quinone + NAD(P)H
hydroquinone + NAD(P)+
riboflavin + NADPH
? + NADP+
-
-
-
-
?
streptonigrin + NAD(P)H
reduced streptonigrin + NAD(P)+
one of the best substrates for NQO1
-
-
?
tetramethyl-1,4-benzoquinone + NADPH
tetramethyl-1,4-benzoquinol + NADP+
-
-
-
-
?
toluquinone + NAD(P)H
toluhydroquinone + NAD(P)+
Sporotrichum pulverulentum
-
-
-
?
ubiquinone + NAD(P)H
reduced ubiquinone + NAD(P)+
ubiquinone-1 + NADPH + H+
ubiquinol-1 + NADP+
-
the protein shows NADH-ubiquinone-1 oxidoreductase activity (EC 1.6.5.3), NADPH oxidase (EC 1.6.3.1) and NADPH-ubiquinone-1 oxidoreductase (EC 1.6.5.2) activities
-
-
?
vitamin K + NAD(P)H + H+
reduced vitamin K + NAD(P)+
-
-
-
?
vitamin K2 + NAD(P)H
reduced vitamin K2 + NAD(P)+
-
-
-
?
[Fe(CN)6]3- + NAD(P)H
[Fe(CN)6]4- + NAD(P)+
additional information
?
-
1,4-benzoquinone + NAD(P)H + H+
1,4-benzoquinol + NAD(P)+
-
-
-
?
1,4-benzoquinone + NAD(P)H + H+
1,4-benzoquinol + NAD(P)+
-
-
-
?
1,4-benzoquinone + NADH + H+
1,4-benzoquinol + NAD+
-
-
-
r
1,4-benzoquinone + NADH + H+
1,4-benzoquinol + NAD+
-
-
-
r
1,4-naphthoquinone + NAD(P)H
1,4-naphthohydroquinone + NAD(P)+
-
-
-
?
1,4-naphthoquinone + NAD(P)H
1,4-naphthohydroquinone + NAD(P)+
-
-
-
?
1,4-naphthoquinone + NAD(P)H
1,4-naphthohydroquinone + NAD(P)+
-
-
-
?
1,4-naphthoquinone + NAD(P)H
1,4-naphthohydroquinone + NAD(P)+
-
-
-
?
1,4-naphthoquinone + NAD(P)H
1,4-naphthohydroquinone + NAD(P)+
-
-
-
?
1,4-naphthoquinone + NAD(P)H
1,4-naphthohydroquinone + NAD(P)+
-
-
-
-
?
1,4-naphthoquinone + NAD(P)H
1,4-naphthohydroquinone + NAD(P)+
-
-
-
-
?
1,4-naphthoquinone + NAD(P)H
1,4-naphthohydroquinone + NAD(P)+
-
-
-
?
2 ferricyanide + NAD(P)H
2 ferrocyanide + NAD(P)+ + H+
-
-
-
-
?
2 ferricyanide + NAD(P)H
2 ferrocyanide + NAD(P)+ + H+
-
-
-
-
?
2,3-dihydroxy-5-methyl-1,4-benzoquinone + NAD(P)H
2,3-dihydroxy-5-methyl-1,4-benzoquinol + NAD(P)+
-
-
-
?
2,3-dihydroxy-5-methyl-1,4-benzoquinone + NAD(P)H
2,3-dihydroxy-5-methyl-1,4-benzoquinol + NAD(P)+
-
-
-
?
2-methyl-1,4-naphthoquinone + NAD(P)H
2-methyl-1,4-naphthoquinol + NAD(P)+
-
artificial acceptor, trivial name menadione
-
?
2-methyl-1,4-naphthoquinone + NAD(P)H
2-methyl-1,4-naphthoquinol + NAD(P)+
-
artificial acceptor, trivial name menadione
-
?
2-methyl-1,4-naphthoquinone + NAD(P)H
2-methyl-1,4-naphthoquinol + NAD(P)+
-
artificial acceptor, trivial name menadione
-
?
2-methyl-1,4-naphthoquinone + NAD(P)H
2-methyl-1,4-naphthoquinol + NAD(P)+
-
artificial acceptor, trivial name menadione
-
?
2-methyl-1,4-naphthoquinone + NAD(P)H
2-methyl-1,4-naphthoquinol + NAD(P)+
-
-
-
?
2-methyl-1,4-naphthoquinone + NAD(P)H
2-methyl-1,4-naphthoquinol + NAD(P)+
-
involved in the process of reductive activation of several cytotoxic antitumor quinones, such as mitomycins, anthracyclines and azaridinylbenzoquinones
-
?
2-methyl-1,4-naphthoquinone + NAD(P)H
2-methyl-1,4-naphthoquinol + NAD(P)+
-
-
-
-
?
2-methyl-1,4-naphthoquinone + NAD(P)H
2-methyl-1,4-naphthoquinol + NAD(P)+
-
-
-
?
2-methyl-1,4-naphthoquinone + NAD(P)H
2-methyl-1,4-naphthoquinol + NAD(P)+
-
artificial acceptor, trivial name menadione
-
?
2-methyl-1,4-naphthoquinone + NAD(P)H
2-methyl-1,4-naphthoquinol + NAD(P)+
-
-
-
?
2-methyl-1,4-naphthoquinone + NAD(P)H
2-methyl-1,4-naphthoquinol + NAD(P)+
-
microsomal enzyme
-
?
2-methyl-1,4-naphthoquinone + NAD(P)H
2-methyl-1,4-naphthoquinol + NAD(P)+
-
artificial acceptor, trivial name menadione
-
?
2-methyl-1,4-naphthoquinone + NAD(P)H
2-methyl-1,4-naphthoquinol + NAD(P)+
-
artificial acceptor, trivial name menadione
-
?
2-methyl-1,4-naphthoquinone + NAD(P)H
2-methyl-1,4-naphthoquinol + NAD(P)+
-
artificial acceptor, trivial name menadione
-
?
2-methyl-1,4-naphthoquinone + NAD(P)H
2-methyl-1,4-naphthoquinol + NAD(P)+
-
artificial acceptor, trivial name menadione
-
?
2-methyl-1,4-naphthoquinone + NAD(P)H
2-methyl-1,4-naphthoquinol + NAD(P)+
-
-
-
?
2-methyl-1,4-naphthoquinone + NADH
2-methyl-1,4-naphthoquinol + NAD+
-
-
-
-
?
2-methyl-1,4-naphthoquinone + NADH
2-methyl-1,4-naphthoquinol + NAD+
-
-
-
-
?
2-methyl-1,4-naphthoquinone + NADH
2-methyl-1,4-naphthoquinol + NAD+
-
-
-
-
?
2-methyl-1,4-naphthoquinone + NADH
2-methyl-1,4-naphthoquinol + NAD+
-
-
-
-
?
2-methyl-1,4-naphthoquinone + NADPH
2-methyl-1,4-naphthoquinol + NADp+
-
-
-
-
?
2-methyl-1,4-naphthoquinone + NADPH
2-methyl-1,4-naphthoquinol + NADp+
-
-
-
-
?
2-methyl-1,4-naphthoquinone + NADPH
2-methyl-1,4-naphthoquinol + NADp+
-
-
-
-
?
2-methyl-1,4-naphthoquinone + NADPH
2-methyl-1,4-naphthoquinol + NADp+
-
-
-
-
?
2-methyl-3-phytyl-1,4-naphthoquinone + NAD(P)H
2-methyl-3-phytyl-1,4-naphthohydroquinone + NAD(P)+
-
-
-
-
?
2-methyl-3-phytyl-1,4-naphthoquinone + NAD(P)H
2-methyl-3-phytyl-1,4-naphthohydroquinone + NAD(P)+
-
trivial name vitamin K1
-
?
2-methyl-3-phytyl-1,4-naphthoquinone + NAD(P)H
2-methyl-3-phytyl-1,4-naphthohydroquinone + NAD(P)+
-
no activity with vitamin K1 diphosphate, menadione diphosphate, vitamin K1 oxide, d-alpha-tocopherol and d-alpha-tocoquinone
-
?
2-methyl-3-phytyl-1,4-naphthoquinone + NAD(P)H
2-methyl-3-phytyl-1,4-naphthohydroquinone + NAD(P)+
-
trivial name vitamin K1
-
?
2-methyl-3-phytyl-1,4-naphthoquinone + NAD(P)H
2-methyl-3-phytyl-1,4-naphthohydroquinone + NAD(P)+
-
trivial name vitamin K1
-
?
3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide + NAD(P)H
reduced 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide + NAD(P)+
-
-
-
?
3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide + NAD(P)H
reduced 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide + NAD(P)+
-
-
-
-
?
5-(1-aziridinyl)-3-(hydroxymethyl)-2-(3-hydroxy-1-propenyl)-1-methyl-1H-indole-4,7-dione + NAD(P)H
5-(1-aziridinyl)-3-(hydroxymethyl)-2-(3-hydroxy-1-propenyl)-1-methyl-1H-indole-4,7-diol + NAD(P)+
-
-
-
?
5-(1-aziridinyl)-3-(hydroxymethyl)-2-(3-hydroxy-1-propenyl)-1-methyl-1H-indole-4,7-dione + NAD(P)H
5-(1-aziridinyl)-3-(hydroxymethyl)-2-(3-hydroxy-1-propenyl)-1-methyl-1H-indole-4,7-diol + NAD(P)+
-
-
-
?
5-(1-aziridinyl)-3-(hydroxymethyl)-2-(3-hydroxy-1-propenyl)-1-methyl-1H-indole-4,7-dione + NAD(P)H
5-(1-aziridinyl)-3-(hydroxymethyl)-2-(3-hydroxy-1-propenyl)-1-methyl-1H-indole-4,7-diol + NAD(P)+
-
-
-
?
5-(aziridin-1-yl)-2,4-dinitrobenzamide + NAD(P)H
5-(aziridin-1-yl)-4-hydroxylamino-2-nitrobenzamide + NAD(P)+
-
-
-
?
5-(aziridin-1-yl)-2,4-dinitrobenzamide + NAD(P)H
5-(aziridin-1-yl)-4-hydroxylamino-2-nitrobenzamide + NAD(P)+
-
-
-
?
5-(aziridin-1-yl)-2,4-dinitrobenzamide + NAD(P)H
5-(aziridin-1-yl)-4-hydroxylamino-2-nitrobenzamide + NAD(P)+
-
-
-
?
5-(aziridin-1-yl)-2,4-dinitrobenzamide + reduced dihydronicotineamide riboside
5-(aziridin-1-yl)-4-hydroxylamino-2-nitrobenzamide + oxidized dihydronicotineamide riboside
-
-
-
?
5-(aziridin-1-yl)-2,4-dinitrobenzamide + reduced dihydronicotineamide riboside
5-(aziridin-1-yl)-4-hydroxylamino-2-nitrobenzamide + oxidized dihydronicotineamide riboside
-
-
-
?
5-(aziridin-1-yl)-2,4-dinitrobenzamide + reduced dihydronicotineamide riboside
5-(aziridin-1-yl)-4-hydroxylamino-2-nitrobenzamide + oxidized dihydronicotineamide riboside
-
-
-
?
alpha-tocopherolquinone + NAD(P)H
reduced alpha-tocopherolquinone + NAD(P)+
-
-
-
?
alpha-tocopherolquinone + NAD(P)H
reduced alpha-tocopherolquinone + NAD(P)+
-
-
-
-
?
benzoquinone + 2 NAD(P)H + H+
benzohydroquinone + 2 NAD(P)+
-
-
-
?
benzoquinone + 2 NAD(P)H + H+
benzohydroquinone + 2 NAD(P)+
-
-
-
?
benzoquinone + 2 NAD(P)H + H+
benzohydroquinone + 2 NAD(P)+
-
no activity with coenzyme Q6 and vitamin K1
-
?
benzoquinone + 2 NAD(P)H + H+
benzohydroquinone + 2 NAD(P)+
-
-
-
?
benzoquinone + 2 NAD(P)H + H+
benzohydroquinone + 2 NAD(P)+
-
no reaction with p-benzoquinone
-
-
?
benzoquinone + NADH
?
-
-
-
-
?
benzoquinone + NADH
?
-
-
-
-
?
chromate(IV) + H2O
chromate(III) + H2O2
-
-
-
-
?
chromate(IV) + H2O
chromate(III) + H2O2
-
-
-
-
?
chromate(VI) + H2O
chromate(III) + H2O2
-
-
-
-
?
chromate(VI) + H2O
chromate(III) + H2O2
-
extremely poor substrate
-
-
?
coenzyme Q0 + NAD(P)H
reduced coenzyme Q0 + NADP+
-
-
-
-
?
coenzyme Q0 + NAD(P)H
reduced coenzyme Q0 + NADP+
-
-
-
-
?
coenzyme Q1 + NAD(P)H
reduced coenzyme Q1 + NADP+
-
-
-
-
?
coenzyme Q1 + NAD(P)H
reduced coenzyme Q1 + NADP+
-
-
-
-
?
duroquinone + NADH
? + NAD+
-
-
-
-
?
duroquinone + NADH
? + NAD+
-
-
-
-
?
duroquinone + NADPH
? + NADP+
-
-
-
-
?
duroquinone + NADPH
? + NADP+
-
-
-
-
?
juglone + NAD(P)H
dihydrojuglone + NAD(P)+
-
-
-
?
juglone + NAD(P)H
dihydrojuglone + NAD(P)+
-
-
-
?
juglone + NADH
dihydrojuglone + NAD+
-
-
-
-
?
juglone + NADH
dihydrojuglone + NAD+
-
-
-
-
?
K3[Fe(CN)6] + NAD(P)H
K4[Fe(CN)6] + NAD(P)+
-
no activity with coenzyme Q10
-
?
K3[Fe(CN)6] + NAD(P)H
K4[Fe(CN)6] + NAD(P)+
-
no activity with lipoic acid, cytochrome c and vitamin K1
-
?
K3[Fe(CN)6] + NAD(P)H
K4[Fe(CN)6] + NAD(P)+
-
no activity with lipoic acid, cytochrome c and vitamin K1
-
?
K3[Fe(CN)6] + NAD(P)H
K4[Fe(CN)6] + NAD(P)+
-
-
-
?
K3[Fe(CN)6] + NAD(P)H
K4[Fe(CN)6] + NAD(P)+
-
-
-
?
K3[Fe(CN)6] + NAD(P)H
K4[Fe(CN)6] + NAD(P)+
-
no activity with O2, vitamin K3, ubiquinone-30 and 2-p-iodophenyl-3-p-nitrophenyl-5-phenyltetrazolium chloride
-
?
K3[Fe(CN)6] + NAD(P)H
K4[Fe(CN)6] + NAD(P)+
-
no activity with lipoic acid, cytochrome c and vitamin K1
-
?
menadione + NAD(P)H
reduced menadione + NAD(P)+
-
-
-
?
menadione + NAD(P)H
reduced menadione + NAD(P)+
-
-
-
?
menadione + NADH
?
-
-
-
-
?
menadione + NADH
?
-
-
-
-
?
menadione + NADH
reduced menadione + NAD+
-
-
-
-
?
menadione + NADH
reduced menadione + NAD+
-
-
-
?
menadione + NADH
reduced menadione + NAD+
-
-
-
?
menadione + NADH
reduced menadione + NAD+
-
-
-
-
?
menadione + NADH + H+
menadiol + NAD+
-
-
-
-
r
menadione + NADH + H+
menadiol + NAD+
-
-
-
-
r
menadione + NADH + H+
menadiol + NAD+
-
-
-
-
r
menadione + NADH + H+
menadiol + NAD+
-
-
-
-
r
methyl red + NAD(P)H
reduced methyl red + NAD(P)+
-
-
-
?
methyl red + NAD(P)H
reduced methyl red + NAD(P)+
-
-
-
-
?
NAD(P)H + H+ + oxidized 2,6-dichlorophenolindophenol
NAD(P)+ + reduced 2,6-dichlorophenolindophenol
-
-
-
?
NAD(P)H + H+ + oxidized 2,6-dichlorophenolindophenol
NAD(P)+ + reduced 2,6-dichlorophenolindophenol
-
-
-
?
NAD(P)H + H+ + oxidized 2,6-dichlorophenolindophenol
NAD(P)+ + reduced 2,6-dichlorophenolindophenol
-
-
-
?
NAD(P)H + H+ + oxidized 2,6-dichlorophenolindophenol
NAD(P)+ + reduced 2,6-dichlorophenolindophenol
-
-
-
?
NAD(P)H + H+ + oxidized 2,6-dichlorophenolindophenol
NAD(P)+ + reduced 2,6-dichlorophenolindophenol
-
low activity
-
?
NAD(P)H + H+ + oxidized 2,6-dichlorophenolindophenol
NAD(P)+ + reduced 2,6-dichlorophenolindophenol
-
-
-
?
NAD(P)H + H+ + oxidized 2,6-dichlorophenolindophenol
NAD(P)+ + reduced 2,6-dichlorophenolindophenol
-
-
-
?
NAD(P)H + H+ + oxidized 2,6-dichlorophenolindophenol
NAD(P)+ + reduced 2,6-dichlorophenolindophenol
-
-
-
?
NAD(P)H + H+ + oxidized 2,6-dichlorophenolindophenol
NAD(P)+ + reduced 2,6-dichlorophenolindophenol
-
-
-
-
?
NAD(P)H + H+ + oxidized 2,6-dichlorophenolindophenol
NAD(P)+ + reduced 2,6-dichlorophenolindophenol
-
-
-
?
NAD(P)H + H+ + oxidized 2,6-dichlorophenolindophenol
NAD(P)+ + reduced 2,6-dichlorophenolindophenol
-
-
-
-
?
NAD(P)H + H+ + oxidized 2,6-dichlorophenolindophenol
NAD(P)+ + reduced 2,6-dichlorophenolindophenol
-
low activity
-
?
NAD(P)H + H+ + oxidized 2,6-dichlorophenolindophenol
NAD(P)+ + reduced 2,6-dichlorophenolindophenol
-
-
-
?
NAD(P)H + H+ + oxidized 2,6-dichlorophenolindophenol
NAD(P)+ + reduced 2,6-dichlorophenolindophenol
-
-
-
?
NAD(P)H + H+ + oxidized 2,6-dichlorophenolindophenol
NAD(P)+ + reduced 2,6-dichlorophenolindophenol
-
-
-
?
NAD(P)H + H+ + oxidized 2,6-dichlorophenolindophenol
NAD(P)+ + reduced 2,6-dichlorophenolindophenol
-
-
-
-
?
NAD(P)H + H+ + oxidized 2,6-dichlorophenolindophenol
NAD(P)+ + reduced 2,6-dichlorophenolindophenol
-
microsomal enzyme
-
?
NADH + H+ + 17-(allylamino)-17-demethoxygeldanamycin
?
-
NAD(P)H:quinone oxidoreductase 1 in pancreatic cell lines metabolizes the heat shock protein 90 inhibitor 17-(allylamino)-17-demethoxygeldanamycin to the corresponding hydroquinone
-
-
?
NADH + H+ + 17-(allylamino)-17-demethoxygeldanamycin
?
-
NAD(P)H:quinone oxidoreductase 1 metabolizes the heat shock protein 90 inhibitor 17-(allylamino)-17-demethoxygeldanamycin to the corresponding hydroquinone
-
-
?
NADH + H+ + 2,3-dimethoxy-5-methyl-1,4-benzoquinone
NAD+ + 2,3-dimethoxy-5-methyl-1,4-benzoquinol
-
-
-
-
?
NADH + H+ + 2,3-dimethoxy-5-methyl-1,4-benzoquinone
NAD+ + 2,3-dimethoxy-5-methyl-1,4-benzoquinol
i.e. ubiquinone-10, UQ-10, a quinone electron acceptor
-
-
r
NADH + H+ + 2,3-dimethoxy-5-methyl-1,4-benzoquinone
NAD+ + 2,3-dimethoxy-5-methyl-1,4-benzoquinol
i.e. ubiquinone-10, UQ-10, a quinone electron acceptor
-
-
r
NADH + H+ + a quinone
NAD+ + a hydroquinone
hydride transfer occurs from the 4-pro-S position of NADH to the solvent-accessible si side of the flavin ring
-
-
r
NADH + H+ + a quinone
NAD+ + a hydroquinone
hydride transfer occurs from the 4-pro-S position of NADH to the solvent-accessible si side of the flavin ring. The first, reductive half-reaction of flavin cofactor is rate-limiting
-
-
r
NADH + H+ + a quinone
NAD+ + a hydroquinone
hydride transfer occurs from the 4-pro-S position of NADH to the solvent-accessible si side of the flavin ring
-
-
r
NADH + H+ + a quinone
NAD+ + a hydroquinone
hydride transfer occurs from the 4-pro-S position of NADH to the solvent-accessible si side of the flavin ring. The first, reductive half-reaction of flavin cofactor is rate-limiting
-
-
r
NADH + H+ + a quinone
NAD+ + a hydroquinone
-
-
-
-
?
NADPH + H+ + 17-(allylamino)-17-demethoxygeldanamycin
?
-
NAD(P)H:quinone oxidoreductase 1 in pancreatic cell lines metabolizes the heat shock protein 90 inhibitor 17-(allylamino)-17-demethoxygeldanamycin to the corresponding hydroquinone
-
-
?
NADPH + H+ + 17-(allylamino)-17-demethoxygeldanamycin
?
-
NAD(P)H:quinone oxidoreductase 1 metabolizes the heat shock protein 90 inhibitor 17-(allylamino)-17-demethoxygeldanamycin to the corresponding hydroquinone
-
-
?
NADPH + H+ + oxidized 2,6-dichlorophenolindophenol
NADP+ + reduced 2,6-dichlorophenolindophenol
-
-
-
-
?
NADPH + H+ + oxidized 2,6-dichlorophenolindophenol
NADP+ + reduced 2,6-dichlorophenolindophenol
-
-
-
-
?
NADPH + H+ + quinone
NADP+ + ?
-
-
-
-
?
NADPH + H+ + quinone
NADP+ + ?
-
TNF alpha and LPS induce Nqo1 mRNA expression
-
-
?
oxidized 2,6-dichlorophenolindophenol + NADH + H+
reduced 2,6-dichlorophenolindophenol + NAD+
-
-
-
-
r
oxidized 2,6-dichlorophenolindophenol + NADH + H+
reduced 2,6-dichlorophenolindophenol + NAD+
-
-
-
-
r
oxidized dichlorophenol-indophenol + NAD(P)H
reduced dichlorophenol-indophenol + NADP+
-
-
-
-
?
oxidized dichlorophenol-indophenol + NAD(P)H
reduced dichlorophenol-indophenol + NADP+
-
-
-
-
?
quinone + NAD(P)H
hydroquinone + NAD(P)+
-
protection of cells against damage by reactive oxygen species generated during oxidative cycling of quinones and semiquinone radicals
-
?
quinone + NAD(P)H
hydroquinone + NAD(P)+
-
possible role in seed germination
-
?
ubiquinone + NAD(P)H
reduced ubiquinone + NAD(P)+
-
-
-
?
ubiquinone + NAD(P)H
reduced ubiquinone + NAD(P)+
-
-
-
-
?
[Fe(CN)6]3- + NAD(P)H
[Fe(CN)6]4- + NAD(P)+
-
-
-
?
[Fe(CN)6]3- + NAD(P)H
[Fe(CN)6]4- + NAD(P)+
-
-
-
?
additional information
?
-
role of enzyme in protecting against environmental stressors
-
-
?
additional information
?
-
-
role of enzyme in protecting against environmental stressors
-
-
?
additional information
?
-
role of enzyme in protecting against environmental stressors
-
-
?
additional information
?
-
-
role of enzyme in protecting against environmental stressors
-
-
?
additional information
?
-
-
NQO1 activity colocalizes closely with Alzheimers disease pathology supporting a presumed role as an antioxidant system upregulated in response to the oxidative stress of the Alzheimers disease process
-
-
?
additional information
?
-
-
the enzyme is involved in the metabolic activation of carcinogenic aristolochic acid
-
-
?
additional information
?
-
enzyme contributes to the capacity of keratinocytes to protect epidermis against oxidant stress
-
-
?
additional information
?
-
-
enzyme contributes to the capacity of keratinocytes to protect epidermis against oxidant stress
-
-
?
additional information
?
-
-
increased enzyme expression reflects an endogenous defense response against reactive oxygen species-mediated cellular toxicity
-
-
?
additional information
?
-
-
no activity with 2-[2,4-dinitro-6-(trifluoromethyl)phenyl]-5-nitro-1,2,3,4-tetrahydronaphthalene and 2-(2,4-dinitrophenyl)-7-nitro-1,2,3,4-tetrahydronaphthalene
-
-
?
additional information
?
-
(+-)-dunnione and its ortho-quinone analogues acts as substrates. The biological activity is favored by the presence of methyl group at the C ring and methoxy group at the A ring. The ortho-quinones exert their antitumor activity through NQO1-mediated reactive oxygen species production by redox cycling
-
-
?
additional information
?
-
-
lack of NQO1 in male mice increases benzene-induced hematotoxicity but not genotoxicity or the DNA damage response. NQO1 appears critical in female mice for detoxifying the metabolites of benzene responsible for genotoxicity, hematotoxicity, and induction of the DNA damage response
-
-
?
additional information
?
-
-
V5+ down-regulates Nqo1 at the transcriptional level, possibly through inhibiting the ATP-dependent activation of Nrf2
-
-
?
additional information
?
-
the flavoprotein ferric reductase B, FerB, from Paracoccus denitrificans is one of two major enzymes able to reduce Fe(III)-ligand complexes when NADH is the electron donor. The protein is also active as a chromate reductase and, to a substantially greater extent, as a quinone reductase
-
-
?
additional information
?
-
-
the flavoprotein ferric reductase B, FerB, from Paracoccus denitrificans is one of two major enzymes able to reduce Fe(III)-ligand complexes when NADH is the electron donor. The protein is also active as a chromate reductase and, to a substantially greater extent, as a quinone reductase
-
-
?
additional information
?
-
low activity with riboflavin instead of FMN
-
-
?
additional information
?
-
-
low activity with riboflavin instead of FMN
-
-
?
additional information
?
-
the flavoprotein ferric reductase B, FerB, from Paracoccus denitrificans is one of two major enzymes able to reduce Fe(III)-ligand complexes when NADH is the electron donor. The protein is also active as a chromate reductase and, to a substantially greater extent, as a quinone reductase
-
-
?
additional information
?
-
low activity with riboflavin instead of FMN
-
-
?
additional information
?
-
catalyzes the two-electron reduction of several quinones and other electron acceptors utilizing either NADH or NADPH as an electron donor
-
-
?
additional information
?
-
-
catalyzes the two-electron reduction of several quinones and other electron acceptors utilizing either NADH or NADPH as an electron donor
-
-
?
additional information
?
-
-
ChrR minimizes intracellular H2O2 stress
-
-
?
additional information
?
-
-
ChrR reduces quinones by simultaneous two-electron transfer, avoiding formation of highly reactive semiquinone intermediates and producing quinols that promote tolerance of H2O2
-
-
?
additional information
?
-
-
ChrR minimizes intracellular H2O2 stress
-
-
?
additional information
?
-
-
ChrR reduces quinones by simultaneous two-electron transfer, avoiding formation of highly reactive semiquinone intermediates and producing quinols that promote tolerance of H2O2
-
-
?
additional information
?
-
-
plays one of the main roles in the bioactivation of quinoidal drugs
-
-
?
additional information
?
-
-
the enzyme is involved in the metabolic activation of carcinogenic aristolochic acid
-
-
?
additional information
?
-
-
the main cytotoxicity mechanism of antitumour aziridinyl-benzoquinones is their two-electron reduction to alkylating products by NAD(P)H:quinone oxidoreductase. In addition to the activation of NQO1 the oxidative stress, presumably initiated by single-electron enzymatic reduction, plays an important role in the cytotoxicity of aziridinyl-substituted quinones
-
-
?
additional information
?
-
-
naphthoquinone-based vitamin (vitamin K1) is not a substrate for purified rat NQO1
-
-
?
additional information
?
-
-
regeneration of alpha-tocopherol may be one of the physiologic functions of this enzyme
-
-
?
additional information
?
-
TmQR2 could play a role in protecting the infected epidermis
-
-
?
additional information
?
-
-
TmQR2 could play a role in protecting the infected epidermis
-
-
?
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(A)-2-Azido-NAD+
-
photodependent inhibition
(A)-8-azido-NAD+
-
photodependent inhibition
1,4-diaminoanthraquinone-2-sulfonic acid
-
-
1,4-Naphthohydroquinone
-
competitive vs. 1,4-naphthohydroquinone, noncompetitive vs. NADPH
1-amino-4-[(3-carboxyphenyl)amino]-anthraquinone-2-sulfonic acid
-
-
1-amino-4-[(4-amino-3-sulfophenyl)amino]-anthraquinone-2-sulfonic acid
-
-
1-aminoanthraquinone-2-carboxylic acid
-
-
1-hydroxy-2-(1-naphthylmethyl)-3H-benzo[f]chromen-3-one
-
1-hydroxy-2-(2-naphthylmethyl)-3H-benzo[f]chromen-3-one
-
1-hydroxy-2-dodecyl-4(1H)-quinolone
-
-
1-hydroxy-2-dodecyl-4(1H)quinolone
-
-
1-hydroxy-2-octyl-4(1H)quinolone
-
-
1-hydroxy-2-[2-(nitrooxy)ethyl]-1-oxo-2-(2,4,6-trinitro-3-(nitro[2-(nitrooxy)ethyl]amino)phenyl)diazanium
-
competitive
1-[3,5-dinitro-2-(1,2,3,4-tetrahydronaphthalen-2-yl)phenyl]-1-oxohydrazinium
-
-
10-nitro-5,6-dihydrobenzimidazo[2,1-a]isoquinoline 12-oxide
-
-
10-nitro-5,6-dihydrobenzimidazo[2,1-a]isoquinoline-8-carboxamide 12-oxide
-
-
10-nitro-5,6-dihydrobenzimidazo[2,1-a]isoquinoline-9-carboxamide 12-oxide
-
-
2,10-dinitro-5,6-dihydrobenzimidazo[2,1-a]isoquinoline 12-oxide
-
-
2,2'-dimethoxy-trans-stilbene
2,4'-dimethoxy-cis-stilbene
2,4'-dimethoxy-trans-stilbene
2,4,4'-trimethoxy-cis-stilbene
2,4,4'-trimethoxy-trans-stilbene
2,4,6-trinitrotoluene
-
competitive
2,4-dinitro-5-(1,2,3,4-tetrahydronaphthalen-2-yl)benzamide
-
-
2,4-dinitro-5-(5-nitro-1,2,3,4-tetrahydronaphthalen-2-yl)benzamide
-
-
2,4-dinitro-5-(7-nitro-1,2,3,4-tetrahydronaphthalen-2-yl)benzamide
-
-
2,4-Dinitroaniline
-
0.1 mM, 33% inhibition
2,4-Dinitronaphthol
-
0.1 mM, 90% inhibition
2,6,4'-trimethoxy-trans-stilbene
2-(2,4,6-trinitrophenyl)-1,2,3,4-tetrahydronaphthalene
-
-
2-(2,4-dinitrophenyl)-1,2,3,4-tetrahydronaphthalene
-
-
2-(2,4-dinitrophenyl)-5-nitro-1,2,3,4-tetrahydronaphthalene
-
-
2-(2,4-dinitrophenyl)-7-nitro-1,2,3,4-tetrahydronaphthalene
-
-
2-(4'-chlorophenyl)-indan-1,3-dione
-
0.0002 mM, 50% inhibition
2-benzyl-1-hydroxy-3H-benzo[f]chromen-3-one
-
2-Heptyl-4-hydroxyquinoline-N-oxide
-
-
2-hydroxy-4'-methoxy-trans-stilbene
2-Pivaloyl-1,3-indanedione
-
-
2-[2,4-dinitro-6-(trifluoromethyl)phenyl]-1,2,3,4-tetrahydronaphthalene
-
-
2-[2,4-dinitro-6-(trifluoromethyl)phenyl]-5-nitro-1,2,3,4-tetrahydronaphthalene
-
-
2-[2,4-dinitro-6-(trifluoromethyl)phenyl]-7-nitro-1,2,3,4-tetrahydronaphthalene
-
-
2-[nitro(2,4,6-trinitrophenyl)amino]ethyl nitrate
-
competitive
3,3'-(9H-fluoren-3-ylmethanediyl)bis(4-hydroxy-2H-chromen-2-one)
-
3,3'-(biphenyl-4-ylmethanediyl)bis(4-hydroxy-2H-chromen-2-one)
-
3,3'-(furan-2-ylmethanediyl)bis(4-hydroxy-2H-chromen-2-one)
-
3,3'-(naphthalen-2-ylmethanediyl)bis(4-hydroxy-2H-chromen-2-one)
-
3,3'-(phenylmethanediyl)bis(4,7-dihydroxy-2H-chromen-2-one)
-
3,3'-(phenylmethanediyl)bis(4-hydroxy-2H-chromen-2-one)
-
3,3'-(pyridin-2-ylmethanediyl)bis(4,7-dihydroxy-2H-chromen-2-one)
-
3,3'-(quinolin-3-ylmethanediyl)bis(4-hydroxy-2H-chromen-2-one)
-
3,3'-(thiophen-2-ylmethanediyl)bis(4-hydroxy-2H-chromen-2-one)
-
3,3'-([4-[(E)-2-phenylethenyl]phenyl]methanediyl)bis(4-hydroxy-2H-chromen-2-one)
-
3,3'-butane-1,1-diylbis(4-hydroxy-2H-chromen-2-one)
-
3,3'-methanediylbis(4,7-dihydroxy-2H-chromen-2-one)
-
3,3'-methanediylbis(4-hydroxy-2H-benzo[h]chromen-2-one)
-
3,3'-methanediylbis(4-hydroxy-2H-chromen-2-one)
-
-
3,3'-methanediylbis(4-hydroxy-5-methoxy-2H-chromen-2-one)
3,3'-methanediylbis(4-hydroxy-6,7-dimethoxy-2H-chromen-2-one)
3,3'-methanediylbis(4-hydroxy-6,7-dimethyl-2H-chromen-2-one)
3,3'-methanediylbis(4-hydroxy-6,8-dibromo-2H-chromen-2-one)
-
3,3'-methanediylbis(4-hydroxy-6-chloro-2H-chromen-2-one)
-
3,3'-methanediylbis(4-hydroxy-6-fluoro-2H-chromen-2-one)
-
3,3'-methanediylbis(4-hydroxy-6-methoxy-2H-chromen-2-one)
3,3'-methanediylbis(4-hydroxy-7,8-dimethyl-2H-chromen-2-one)
3,3'-methanediylbis(4-hydroxy-7-fluoro-2H-chromen-2-one)
-
3,3'-methanediylbis(4-hydroxy-7-methoxy-2H-chromen-2-one)
3,3'-methylene-bis(4-hydroxycoumarin)
3,3'-methylenebis(4-hydroxy-6-methyl-2H-chromen-2-one)
-
3,3'-[(4-chlorophenyl)methanediyl]bis(4-hydroxy-2H-chromen-2-one)
-
3,3'-[(4-hydroxy-3-methoxyphenyl)methanediyl]bis(4-hydroxy-2H-chromen-2-one)
-
3,3'-[(4-hydroxyphenyl)methanediyl]bis(4-hydroxy-2H-chromen-2-one)
-
3,3'-[(4-methoxyphenyl)methanediyl]bis(4-hydroxy-2H-chromen-2-one)
-
3,3'-[[3,5-bis(benzyloxy)phenyl]methanediyl]bis(4-hydroxy-2H-chromen-2-one)
-
3,3'-[[4-(1-methylethyl)phenyl]methanediyl]bis(4-hydroxy-2H-chromen-2-one)
-
3,3'-[[4-(dimethylamino)phenyl]methanediyl]bis(4-hydroxy-2H-chromen-2-one)
-
3,4'-dimethoxy-cis-stilbene
3,4'-dimethoxy-trans-stilbene
-
-
3,4,4'-trimethoxy-cis-stilbene
3,4,4'-trimethoxy-trans-stilbene
3,4,5,4'-tetramethoxy-cis-stilbene
3,4,5,4'-tetramethoxy-trans-stilbene
3,5,4'-trimethoxy-cis-stilbene
3,5,4'-trimethoxy-trans-stilbene
3,5-dihydroxy-4'-methoxy-cis-stilbene
3,5-dihydroxy-4'-methoxy-trans-stilbene
3,5-dinitro-2-(1,2,3,4-tetrahydronaphthalen-2-yl)benzamide
-
-
3,5-dinitro-2-(1,2,3,4-tetrahydronaphthalen-2-yl)benzoic acid
-
-
3,5-dinitro-2-(5-nitro-1,2,3,4-tetrahydronaphthalen-2-yl)benzoic acid
-
-
3,5-dinitro-2-(7-nitro-1,2,3,4-tetrahydronaphthalen-2-yl)benzoic acid
-
-
3-(2,4-difluorophenoxymethyl)-6-methoxy-1,2-dimethylindole-4,7-dione
-
effective inhibitor of the growth of MiaPaCa-2 cells
3-(2-fluoro-4-nitrophenoxymethyl)-5-methoxy-1,2-dimethylindole-4,7-dione
-
-
3-(2-fluoro-4-nitrophenoxymethyl)-6-methoxy-1,2-dimethylindole-4,7-dione
-
effective inhibitor of the growth of MiaPaCa-2 cells
3-(3,4-dimethylbenzyl)-4-hydroxy-2H-chromen-2-one
-
3-(3,4-dimethylbenzyl)-4-hydroxy-6,7-dimethyl-2H-chromen-2-one
3-(4-aminophenoxymethyl)-6-methoxy-1,2-dimethylindole-4,7-dione
-
effective inhibitor of the growth of MiaPaCa-2 cells
3-(4-cyanophenoxymethyl)-6-methoxy-1,2-dimethylindole-4,7-dione
-
effective inhibitor of the growth of MiaPaCa-2 cells; indolequinone derivative 22, dose dependent inhibition of NQO1 activity in MiaPaCa-2
3-(4-fluorophenoxymethyl)-6-methoxy-1,2-dimethylindole-4,7-dione
-
indolequinone derivative 24, dose dependent inhibition of NQO1 activity in MiaPaCa-2
3-(alpha-phenylpropyl)-4-hydroxycoumarin
-
0.01 mM, 50% inhibition
3-([[4-Iodophenyl]thio]methyl)-5-methoxy-1,2-dimethyl-1H-indole-4,7-dione
compound based on the selective binding of indolequinone analogs to the active site of NQO1 by the stacking effect. [125]I-marked compound can be used as an internal radiation agent for the treatment of cancer
-
3-benzyl-4-hydroxy-2H-benzo[h]chromen-2-one
-
3-benzyl-4-hydroxy-2H-chromen-2-one
-
3-benzyl-4-hydroxy-6,7-dimethyl-2H-chromen-2-one
-
3-hydroxy-4'-methoxy-cis-stilbene
3-hydroxy-4'-methoxy-trans-stilbene
3-hydroxy-4,4'-dimethoxy-cis-stilbene
3-hydroxy-4,4'-dimethoxy-trans-stilbene
3-methoxy-1,2-dimethyl-3-(3-pyridyloxymethyl)indole-4,7-dione
-
-
3-[alpha-(4'-nitrophenyl)-beta-acetylethyl]-4-hydroxycoumarin
-
0.02 mM, 50% inhibition
3-[[3-[bis(4-hydroxy-2-oxo-2H-chromen-3-yl)methyl]phenyl](4-hydroxy-2-oxo-4a,8a-dihydro-2H-chromen-3-yl)methyl]-4-hydroxy-2H-chromen-2-one
-
3-[[4-[bis(4-hydroxy-2-oxo-2H-chromen-3-yl)methyl]phenyl](4,7-dihydroxy-2-oxo-4a,8a-dihydro-2H-chromen-3-yl)methyl]-4,7-dihydroxy-2H-chromen-2-one
-
3-[[4-[bis(4-hydroxy-2-oxo-2H-chromen-3-yl)methyl]phenyl](4-hydroxy-2-oxo-4a,8a-dihydro-2H-chromen-3-yl)methyl]-4-hydroxy-2H-chromen-2-one
-
4',5,7-trihydroxyflavone
-
0.01 mM, 61% inhibition, recombinant NAD(P)H:quinone acceptor oxidoreductase 2
4,10-dinitro-5,6-dihydrobenzimidazo[2,1-a]isoquinoline 12-oxide
-
-
4,10-dinitro-5,6-dihydrobenzimidazo[2,1-a]isoquinoline-9-carboxamide 12-oxide
-
-
4,10-dinitro-8-(trifluoromethyl)-5,6-dihydrobenzimidazo[2,1-a]isoquinoline 12-oxide
-
-
4,4'-dichlorodicoumarol
-
0.001 mM, 50% inhibition
4,4'-dimethoxy-cis-stilbene
4,4'-dimethoxy-trans-stilbene
4,5,6,7-tetranitro-1,3-dihydro-2H-benzimidazol-2-one
-
competitive
4,5,6-trinitro-1,3-dihydro-2H-benzimidazol-2-one
-
competitive
4-amino-2H-chromen-2-one
-
4-chloromercuribenzoate
-
74% residual activity at 0.15 mM
4-hydroxy-3-(1-naphthylmethyl)-2H-benzo[h]chromen-2-one
-
4-hydroxy-3-(1-naphthylmethyl)-2H-chromen-2-one
-
4-hydroxy-3-(2-naphthylmethyl)-2H-benzo[h]chromen-2-one
-
4-hydroxy-3-(2-naphthylmethyl)-2H-chromen-2-one
-
4-hydroxy-3-(naphthalen-1-yl)cyclohepta[h]chromen-2(7H)-one
-
-
4-hydroxy-3-(naphthalen-2-yl)cyclohepta[h]chromen-2(7H)-one
-
-
4-hydroxy-3-phenylcyclohepta[h]chromen-2(7H)-one
-
-
4-hydroxy-3-[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]-2H-1-benzopyran-2-one
10 microM, 89.2% inhibition. At 0.0084 microM, 50% toxicity in A549 cells in the presence of 20 mM beta-lapachone. Inhibitor is used to built a functional affinity-based small-molecule fluoresent probe composed of the NQO1 inhibitor as the recognition group, a linker and the fluorophores group FITC
-
4-hydroxy-6,7-dimethyl-3-(1-naphthylmethyl)-2H-chromen-2-one
-
4-hydroxy-6,7-dimethyl-3-(2-naphthylmethyl)-2H-chromen-2-one
-
4-hydroxy-6,7-dimethyl-3-(naphthalen-1-yl)-2H-chromen-2-one
-
-
4-hydroxy-6,7-dimethyl-3-(naphthalen-2-yl)-2H-chromen-2-one
-
-
4-hydroxy-6,7-dimethyl-3-phenyl-2H-chromen-2-one
-
-
4-hydroxymercuribenzoate
-
0.067 mM, 50% inhibition
4-[bis(4-hydroxy-2-oxo-2H-chromen-3-yl)methyl]benzoic acid
-
5,5'-dithiobis(2-nitrobenzoic acid)
5,6-dimethylxanthenone-4-acetic acid
-
tumour blood flow inhibitor, competitive vs. NADH
5-hydroxy-7-bromoacetylflavone
-
0.00018 mM, 50% inhibition, irreversible, useful as affinity label
5-methoxy-1,2-dimethyl-3-(2,4,6-trifluorophenoxymethyl)indole-4,7-dione
-
effective inhibitor of the growth of MiaPaCa-2 cells; indolequinone derivative 10, mechanism based 80% inhibition
5-methoxy-1,2-dimethyl-3-(2-nitrophenoxymethyl)indole-4,7-dione
-
effective inhibitor of the growth of MiaPaCa-2 cells
5-methoxy-1,2-dimethyl-3-(3-nitrophenoxymethyl)indole-4,7-dione
-
effective inhibitor of the growth of MiaPaCaa-2 cells; indolequinone derivative 6, dose dependent inhibition of NQO1 activity in MiaPaCa-2
5-methoxy-1,2-dimethyl-3-(3-pyridyloxymethyl)indole-4,7-dione
-
indolequinone derivative 12, dose dependent inhibition of NQO1 activity in MiaPaCa-2
5-methoxy-1,2-dimethyl-3-(4-nitrophenoxymethyl)indole-4,7-dione
-
effective inhibitor of the growth of MiaPaCa-2 cells
5-methoxy-1,2-dimethyl-3-(phenoxymethyl)indole-4,7-dione
-
-
5-methoxy-1,2-dimethyl-3-(pyridin-2-yloxymethyl)indole-4,7-dione
-
indolequinone derivative 11, mechanism based 90% inhibition
5-methoxy-1,2-dimethyl-3-(pyridin-4-yloxymethyl)indole-4,7-dione
-
-
5-methoxy-1,2-dimethyl-3-[(4-nitrophenoxy)methyl]-indole-4,7-dione
-
ES936, potent mechanism-based inhibitor of NQO1, complete inhibition at 0.001 mM
5-methoxy-1,2-dimethyl-3-[(4-nitrophenoxy)methyl]indole-4,7-dione
5-methoxy-1,2-dimethyl-3-[(4-pyridinyloxy)methyl]indole-4,7-dione
approximately 90% inhibition of enzyme activity after 4 h, and this inactivation is dependent upon NADH
5-methoxy-1,2-dimethyl-3-[1-(4-nitrophenoxy)ethyl]indole-4,7-dione
-
-
5-methoxy-1,2-dimethyl-[(4-nitrophenoxy)methyl]indole-4,7-dione
6-methoxy-1,2-dimethyl-3-(2,4,6-trifluorophenoxymethyl)indole-4,7-dione
-
effective inhibitor of the growth of MiaPaCa-2 cells; indolequinone derivative 26, mechanism based 90% inhibition
6-methoxy-1,2-dimethyl-3-(2-nitrophenoxymethyl)indole-4,7-dione
-
effective inhibitor of the growth of MiaPaCaa-2 cells
6-methoxy-1,2-dimethyl-3-(3-nitrophenoxymethyl)indole-4,7-dione
-
effective inhibitor of the growth of MiaPaCa-2 cells
6-methoxy-1,2-dimethyl-3-(4-nitrophenoxymethyl)indole-4,7-dione
-
effective inhibitor of the growth of MiaPaCa-2 cells; indolequinone derivative 15, mechanism based 85% inhibition
6-methoxy-1,2-dimethyl-3-(phenoxymethyl)indole-4,7-dione
-
-
6-methoxy-1,2-dimethyl-3-(pyridin-2-yloxymethyl)indole-4,7-dione
-
indolequinone derivative 27, mechanism based 90% inhibition
6-methoxy-1,2-dimethyl-3-(pyridin-4-yloxymethyl)indole-4,7-dione
-
indolequinone derivative 29, mechanism based 95% inhibition
6-methoxy-1,2-dimethyl-3-[(4-nitrophenoxy)methyl]indole-4,7-dione
approximately 90% inhibition of enzyme activity after 4 h, and this inactivation is dependent upon NADH
6-methoxy-1,2-dimethyl-3-[(4-pyridinyloxy)methyl]indole-4,7-dione
approximately 90% inhibition of enzyme activity after 4 h, and this inactivation is dependent upon NADH
6-methoxy-1,2-dimethyl-3-[(acetoxy)methyl]indole-4,7-dione
approximately 90% inhibition of enzyme activity after 4 h, and this inactivation is dependent upon NADH
6-methoxy-1,2-dimethyl-3-[2-nitrophenoxymethyl]indole-4,7-dione
-
indolequinone derivative 19, mechanism based 95% inhibition, dose dependent inhibition of NQO1 activity in MiaPaCa-2
6-methoxy-1,2-dimethyl-3-[4-(trifluoromethyl)phenoxymethyl]-indole-4,7-dione
-
effective inhibitor of the growth of MiaPaCa-2 cells; indolequinone derivative 23, dose dependent inhibition of NQO1 activity in MiaPaCa-2
7,8-dibromoacetylflavone
-
0.00003 mM, 50% inhibition
7-(4-hydroxy-2-oxo-2H-chromen-3-yl)-6a,7-dihydro-4aH,6H,8H-pyrano[3,2-c:5,6-c']dichromene-6,8-dione
-
7-(4-hydroxy-2-oxo-2H-chromen-3-yl)-6H,7H-chromeno[4,3-b]chromen-6-one
-
7-bromoacetylflavone
-
time-dependent inactivation within 30 s, 0.00074 mM, 50% inhibition
7-hydroxylflavone
-
competitive inhibition, 0.00074 mM, 50% inhibition
7-N-acetyldemethyllavendamycin n-butyl amide
lavendamycin analogue 12, selective toxic toward NQO1-rich cells
8-hydroxyquinoline
-
1 mM, 50% inhibition
ADP
-
86% residual activity at 0.2 mM
Alizarin Red S
-
0.04 mM, 38% inhibition
alpha,alpha'-dipyridyl
-
IC50: 1 mM
alpha-naphthoflavone
-
0.01 mM, 75% inhibition, recombinant NAD(P)H:quinone acceptor oxidoreductase 2
Amytal
-
6.6 mM, 55% inhibition
anthraquinone-2-carboxylic acid
-
-
anthraquinone-2-sulfonic acid
-
-
ATP
-
91% residual activity at 0.2 mM
benzoquinol
-
shows noncompetitive inhibition in all conditions, it can bind to multiple enzyme forms or sites, even when either of the substrates (NADH or benzoquinone) is present at high concentrations
beta-naphthoflavone
-
0.01 mM, 76% inhibition, recombinant NAD(P)H:quinone acceptor oxidoreductase 2
capsaicin
-
activity is decreased after the treatment with capsaicin or dicoumarol. Quinone metabolites or other reactive forms of capsaicin may bind covalently to NQO1 and thereby inhibit its activity, leading to production of reactive oxygen species; suppresses NQO1 expression and activity. Quinone metabolites or other reactive forms of capsaicin may bind covalently to NQO1 and thereby inhibit its activity, leading to production of reactive oxygen species
Cibacron Blue F3G-A
-
0.04 mM, 75% inhibition
Cr6+
-
decrease of enzyme mRNA level together with heme oxygenase-1 and glutathione S-transferase Ya
Cu2+
-
decrease of enzyme mRNA expression, via a transcriptional mechanism
curcumin
-
inhibition of enzyme activity in vivo and in vitro. Inducues dissociation of complexes of enzyme with tumor suppressor protein p53 leading to degradation of p53, but not of p53 cancer hot-spot mutant R273H
Dicoumarol dimethylether
-
0.0005, 50% inhibition
diphenylene iodonium chloride
-
-
EGTA
-
95% residual activity at 5 mM
ethyl 5-aziridin-1-yl-2,4-dinitrobenzoate
-
competitive
ethyl bis(2-hydroxy-4-oxo-4H-chromen-3-yl)acetate
ethyl bis(4-hydroxy-2-oxo-2H-chromen-3-yl)acetate
-
flavone-8-acetic acid
-
tumour blood flow inhibitor, competitive vs. NADH
galangin
-
0.01 mM, 100% inhibition, recombinant NAD(P)H:quinone acceptor oxidoreductase 2
HgCl2
-
0.2 mM, 94% inhibition
hydroxy(oxo)(3,6,8-trinitro-9H-carbazol-1-yl)ammonium
-
competitive
lavendamycin beta-hydroxyethyl ester
lavendamycin analogue 12, selective toxic toward NQO1-rich cells
Mersalyl
-
68% residual activity at 0.15 mM
methylene-5,5'-bis(4,6-dioxo-2-methyldihydropyran)
-
0.003 mM, 50% inhibition
morin
-
0.01 mM, 95% inhibition, recombinant NAD(P)H:quinone acceptor oxidoreductase 2
N-ethyl maleimide
-
0.33 mM, complete inhibition
N-methyl-N,2,4,6-tetranitroaniline
-
competitive
N-methyl-N,2,4-trinitroaniline
-
competitive
p-chloromercuribenzoate
-
-
Phenindione
-
0.1 mM, 92% inhibition
phenylmercuric acetate
-
-
Procion blue MX-R
-
0.04 mM, 75% inhibition
quinacrine dihydrochloride
-
0.05 mM, 65-95% inhibition depending on substrate
reserpine
-
competitive inhibitor of DT-diaphorase
salicylate
-
1 mM, 62% inhibition
siRNA
-
siRNA for NQO1 inhibits clonogenic cell death caused by beta-lap
-
SOD
-
inhibits the NADPH:chromate reductase reaction of NQO1
-
Thenoyltrifluoroacetone
-
-
warfarin
-
1 mM, 70% inhibition
1,10-phenanthroline
-
-
1,10-phenanthroline
-
1 mM, 50% inhibition
2,2'-dimethoxy-trans-stilbene
-
-
2,2'-dimethoxy-trans-stilbene
-
-
2,4'-dimethoxy-cis-stilbene
-
-
2,4'-dimethoxy-cis-stilbene
-
-
2,4'-dimethoxy-trans-stilbene
-
-
2,4'-dimethoxy-trans-stilbene
-
-
2,4,4'-trimethoxy-cis-stilbene
-
-
2,4,4'-trimethoxy-cis-stilbene
-
-
2,4,4'-trimethoxy-trans-stilbene
-
-
2,4,4'-trimethoxy-trans-stilbene
-
-
2,4-dinitrophenol
-
0.067 mM, 56% inhibition
2,4-dinitrophenol
-
0.1 mM, 39% inhibition
2,6,4'-trimethoxy-trans-stilbene
-
-
2,6,4'-trimethoxy-trans-stilbene
-
-
2-hydroxy-4'-methoxy-trans-stilbene
-
-
2-hydroxy-4'-methoxy-trans-stilbene
-
-
3,3'-methanediylbis(4-hydroxy-5-methoxy-2H-chromen-2-one)
-
-
3,3'-methanediylbis(4-hydroxy-5-methoxy-2H-chromen-2-one)
-
3,3'-methanediylbis(4-hydroxy-6,7-dimethoxy-2H-chromen-2-one)
-
-
3,3'-methanediylbis(4-hydroxy-6,7-dimethoxy-2H-chromen-2-one)
-
3,3'-methanediylbis(4-hydroxy-6,7-dimethyl-2H-chromen-2-one)
-
-
3,3'-methanediylbis(4-hydroxy-6,7-dimethyl-2H-chromen-2-one)
-
3,3'-methanediylbis(4-hydroxy-6-methoxy-2H-chromen-2-one)
-
-
3,3'-methanediylbis(4-hydroxy-6-methoxy-2H-chromen-2-one)
-
3,3'-methanediylbis(4-hydroxy-7,8-dimethyl-2H-chromen-2-one)
-
-
3,3'-methanediylbis(4-hydroxy-7,8-dimethyl-2H-chromen-2-one)
-
3,3'-methanediylbis(4-hydroxy-7-methoxy-2H-chromen-2-one)
-
-
3,3'-methanediylbis(4-hydroxy-7-methoxy-2H-chromen-2-one)
-
3,3'-methylene-bis(4-hydroxycoumarin)
-
0.000033 mM, 56% inhibition
3,3'-methylene-bis(4-hydroxycoumarin)
-
-
3,3'-methylene-bis(4-hydroxycoumarin)
-
0.1 mM, 97% inhibition
3,3'-methylene-bis(4-hydroxycoumarin)
-
-
3,3'-methylene-bis(4-hydroxycoumarin)
-
-
3,3'-methylene-bis(4-hydroxycoumarin)
-
0.04 mM, complete inhibition
3,3'-methylene-bis(4-hydroxycoumarin)
-
-
3,3'-methylene-bis(4-hydroxycoumarin)
-
0.01 mM, 25% inhibition, recombinant NAD(P)H:quinone acceptor oxidoreductase 2
3,3'-methylene-bis(4-hydroxycoumarin)
-
-
3,3'-methylene-bis(4-hydroxycoumarin)
-
competitive vs. NADH
3,3'-methylene-bis(4-hydroxycoumarin)
-
-
3,3'-methylene-bis(4-hydroxycoumarin)
-
only in the presence of glutathione
3,3'-methylene-bis(4-hydroxycoumarin)
-
trivial name dicoumarol, slight inhibition
3,3'-methylene-bis(4-hydroxycoumarin)
-
-
3,3'-methylene-bis(4-hydroxycoumarin)
-
competitive vs. NADH, uncompetitive vs. vitamin K1
3,3'-methylene-bis(4-hydroxycoumarin)
-
-
3,3'-methylene-bis(4-hydroxycoumarin)
-
competitive vs. NADH
3,4'-dimethoxy-cis-stilbene
-
-
3,4'-dimethoxy-cis-stilbene
-
-
3,4,4'-trimethoxy-cis-stilbene
-
-
3,4,4'-trimethoxy-cis-stilbene
-
-
3,4,4'-trimethoxy-trans-stilbene
-
-
3,4,4'-trimethoxy-trans-stilbene
-
-
3,4,5,4'-tetramethoxy-cis-stilbene
-
-
3,4,5,4'-tetramethoxy-cis-stilbene
-
-
3,4,5,4'-tetramethoxy-trans-stilbene
-
-
3,4,5,4'-tetramethoxy-trans-stilbene
-
-
3,5,4'-trimethoxy-cis-stilbene
-
-
3,5,4'-trimethoxy-cis-stilbene
-
-
3,5,4'-trimethoxy-trans-stilbene
-
-
3,5,4'-trimethoxy-trans-stilbene
-
-
3,5-dihydroxy-4'-methoxy-cis-stilbene
-
-
3,5-dihydroxy-4'-methoxy-cis-stilbene
-
-
3,5-dihydroxy-4'-methoxy-trans-stilbene
-
-
3,5-dihydroxy-4'-methoxy-trans-stilbene
-
-
3-(3,4-dimethylbenzyl)-4-hydroxy-6,7-dimethyl-2H-chromen-2-one
-
-
3-(3,4-dimethylbenzyl)-4-hydroxy-6,7-dimethyl-2H-chromen-2-one
-
3-hydroxy-4'-methoxy-cis-stilbene
-
-
3-hydroxy-4'-methoxy-cis-stilbene
-
-
3-hydroxy-4'-methoxy-trans-stilbene
-
-
3-hydroxy-4'-methoxy-trans-stilbene
-
-
3-hydroxy-4,4'-dimethoxy-cis-stilbene
-
-
3-hydroxy-4,4'-dimethoxy-cis-stilbene
-
-
3-hydroxy-4,4'-dimethoxy-trans-stilbene
-
-
3-hydroxy-4,4'-dimethoxy-trans-stilbene
-
-
4,4'-dimethoxy-cis-stilbene
-
-
4,4'-dimethoxy-cis-stilbene
-
-
4,4'-dimethoxy-trans-stilbene
-
-
4,4'-dimethoxy-trans-stilbene
-
-
5,5'-dithiobis(2-nitrobenzoic acid)
-
1 mM, 67% inhibition, 10 mM, complete inhibition
5,5'-dithiobis(2-nitrobenzoic acid)
-
-
5,7-dihydroxyflavone
-
0.009 mM, approx. 90% inhibition
5,7-dihydroxyflavone
-
0.009 mM, approx. 20% inhibition
5,7-dihydroxyflavone
-
0.009 mM, approx. 80% inhibition
5,7-dihydroxyflavone
-
0.00018 mM, 50% inhibition
5-methoxy-1,2-dimethyl-3-[(4-nitrophenoxy)methyl]indole-4,7-dione
mechanism-based inhibitor, time- and concentration dependent inhibition that requires the presence of NAD(P)H, 0.0015 mM, complete inhibition after 4 min
5-methoxy-1,2-dimethyl-3-[(4-nitrophenoxy)methyl]indole-4,7-dione
ES936, potent inhibitor of NQO1 activity and cell proliferation. Approximately 90% inhibition of enzyme activity after 4 h. Inactivation is dependent upon NADH
5-methoxy-1,2-dimethyl-[(4-nitrophenoxy)methyl]indole-4,7-dione
-
-
5-methoxy-1,2-dimethyl-[(4-nitrophenoxy)methyl]indole-4,7-dione
-
-
chrysin
-
0.01 mM, 100% inhibition, recombinant NAD(P)H:quinone acceptor oxidoreductase 2
Cibacron blue
-
and related anthraquinone dyes
dicoumarol
binding of dicoumarol induces conformational changes involving Y128 and F232 on the surface of enzyme catalytic pocket
dicoumarol
-
inhibitor of NQO1, inhibits clonogenic cell death caused by beta-lap
dicoumarol
i.e. 3,3'-methylenebis(4-hydroxycoumarin), potent competitive inhibitor of NQO1
dicoumarol
-
lack of effect of inhibition of DT-diaphorase by dicoumarol, when the cells are incubated with dopamine and reserpine. Significant cell death only when RCSN-3 cells are incubated with reserpine and dopamine together with the DT-diaphorase inhibitor dicoumarol
dicoumarol
-
in the presence of 0.050 mM of dicoumarol, the protective effect of bromocriptine against H2O2 is completely abolished
dicumarol
-
most potent inhibitor, 12% residual activity at 0.15 mM
dicumarol
most potent competitive inhibitor of QO1. Disadvantages with dicumarol in that it is not selective and can inhibit other enzymes in addition to NQO1 and it can also be extensively protein bound complicating its use in cellular assays
dicumarol
-
inhibits the reduction of chromate by the digiton-permeabilized FLK cells in the presence of NADPH regeneration system. Protects against cytotoxicity by inhibiting NQO1
ES936
-
i.e. 5-methoxy-1,2-dimethyl-3-[(4-nitrophenoxy)methyl]indole-4,7-dione, suicide inhibitor
ES936
effective mechanism-based inhibitor. Inhibits NQO1 in a time- and concentration-dependent manner. In agreement with its role as mechanism-based (suicide substrate) inhibitor, requires the presence of cofactor NADH, and therefore a catalytic turnover, for effective enzyme inhibition. At 100 nanomol concentration, ES936 inhibits more than 95% of NQO1 activity in cells within 30 min, and since it is specific, appears to be a more useful biochemical tool than dicumarol for use in routine NQO1 assays
ES936
-
is an irreversible mechanism-based inhibitor of QR1
ES936
-
pancreatic tumour xenografts in mice grow significantly slower following treatment with ES936
ethyl bis(2-hydroxy-4-oxo-4H-chromen-3-yl)acetate
-
-
ethyl bis(2-hydroxy-4-oxo-4H-chromen-3-yl)acetate
-
trivial tromexan, 0.1 mM, 79% inhibition
mitomycin C
-
mechanism-based inhibitor, in a pH-dependent manner
mitomycin C
-
mechanism-based inhibitor, in a pH-dependent manner
mitomycin C
-
mechanism-based inhibitor, in a pH-dependent manner
NAD+
-
96% residual activity at 0.2 mM
NAD+
-
noncompetitive inhibition with either substrate when the other substrate is at low concentrations. At high NADH concentrations, NAD and benzoquinone are competitive, indicating they bind to a common site or sites
NADP+
-
95% residual activity at 0.2 mM
NADP+
-
noncompetitive vs. NADPH
quercetin
-
-
quercetin
-
0.01 mM, 100% inhibition, recombinant NAD(P)H:quinone acceptor oxidoreductase 2
resveratrol
-
-
additional information
-
insensitive to rotenone, Ca2+, platanetin and flavone have no effect on the NADH:2,3-dimethoxy-5-methyl-1,4-benzoquinone reductase activity of the purified enzyme
-
additional information
-
not inhibited by iodoacetate, 4-chloromercuribenzoate, Cu2+, FeSO4, FeCl3, CdSO4, ZnSO4, CuSO4, EDTA, alpha,alpha'-dipyridiyl, o-phenanthroline, dimethylglyoxime, dithizon, NaCN, amytal, veronal, antimycin, 2,4-dinitrophenol and thyroxin
-
additional information
-
not inhibited by o-phenanthroline, KCN, quinacrine, EDTA and 2,3-dimercapto-1-propanol
-
additional information
-
compounds 5-methoxy-1,2-dimethyl-3-(phenoxymethyl)indole-4,7-dione, 6-methoxy-1,2-dimethyl-3-(phenoxymethyl)indole-4,7-dione, 5-methoxy-1,2-dimethyl-3-(2,4-dinitrophenoxymethyl)indole-4,7-dione, 6-methoxy-1,2-dimethyl-3-(2,4-dinitrophenoxymethyl)indole-4,7-dione, 3-(2-fluoro-4-nitrophenoxymethyl)-5-methoxy-1,2-dimethylindole-4,7-dione, 3-(4-fluorophenoxymethyl)-6-methoxy-1,2-dimethylindole-4,7-dione, 5-methoxy-1,2-dimethyl-3-(pyridin-2-yloxymethyl)indole-4,7-dione, 6-methoxy-1,2-dimethyl-3-(pyridin-2-yloxymethyl)indole-4,7-dione, 5-methoxy-1,2-dimethyl-3-(3-pyridyloxymethyl)indole-4,7-dione, 3-methoxy-1,2-dimethyl-3-(3-pyridyloxymethyl)indole-4,7-dione, 5-methoxy-1,2-dimethyl-3-(pyridin-4-yloxymethyl)indole-4,7-dione, 6-methoxy-1,2-dimethyl-3-(pyridin-4-yloxymethyl)indole-4,7-dione, and 5-methoxy-1,2-dimethyl-3-[1-(4-nitrophenoxy)ethyl]indole-4,7-dione are relatively ineffective at inducing growth inhibition. Inhibition of recombinant NQO1 is related to the pKa of the leaving group: compounds with poorer phenolic leaving groups are poor inhibitors whereas those with more acidic leaving groups are more efficient inhibitors
-
additional information
-
fruit and vegetable consumption may repress rather than induce rectal NQO1 phenotype. Consumption of Compositae is associated with lower rectal NQO1 mRNA level. Consumption of Apiaceae is associated with lower rectal NQO1 activity
-
additional information
fruit and vegetable consumption may repress rather than induce rectal NQO1 phenotype. Consumption of Compositae is associated with lower rectal NQO1 mRNA level. Consumption of Apiaceae is associated with lower rectal NQO1 activity
-
additional information
indolequinones with 4-nitrophenoxy, 4-pyridinyloxy, and acetoxy substituents at the (indol-3-yl)methyl position are NADH-dependent inhibitors of recombinant human NQO1, indicative of mechanism-based inhibition. However, those with hydroxy and phenoxy substituents are poor inhibitors of NQO1 enzyme activity, due to attenuated elimination of the leaving group. 4-pyridinyloxy and acetoxy compounds are potent inhibitors of NQO1 activity but relatively poor inhibitors of cell proliferation. Phenoxy compounds, which are not inhibitors of NQO1 enzymatic activity, demonstrate potent growth inhibition
-
additional information
-
indolequinones with 4-nitrophenoxy, 4-pyridinyloxy, and acetoxy substituents at the (indol-3-yl)methyl position are NADH-dependent inhibitors of recombinant human NQO1, indicative of mechanism-based inhibition. However, those with hydroxy and phenoxy substituents are poor inhibitors of NQO1 enzyme activity, due to attenuated elimination of the leaving group. 4-pyridinyloxy and acetoxy compounds are potent inhibitors of NQO1 activity but relatively poor inhibitors of cell proliferation. Phenoxy compounds, which are not inhibitors of NQO1 enzymatic activity, demonstrate potent growth inhibition
-
additional information
-
growth inhibitory effects of series of methoxystilbenes (E and Z isomers) related to resveratrol on human cancer cell lines, overview
-
additional information
-
synthesis of 2-nitroaryl-1,2,3,4-tetrahydroisoquinolines, nitro-substituted 5,6-dihydrobenzimidazo[2,1-a]isoquinoline N-oxides and related heterocycles as potential bioreducible substrates for the enzymes NAD(P)H: quinone oxidoreductase 1, NQO1, overview
-
additional information
-
almond skin polyphenol extracted with agastrointestinal juice mimic decreases quinone reductase activity. Combining almond skin polyphenol extracted with agastrointestinal juice mimic plus vitamin C has an antagonistic effect
-
additional information
-
enzyme induction effects of series of methoxystilbenes (E and Z isomers) related to resveratrol on murine hepatoma cells, overview
-
additional information
-
-
-
additional information
-
microsomal enzyme: not inhibited by dicoumarol, lapachol and p-chloromercuribenzoate
-
additional information
-
the product inhibition pattern expected if WrbA follows a ping pong mechanism is that the pairs NAD/BQ and NADH/BQH2 display competitive inhibition, whereas the pairs NAD/NADH and BQ/BQH2 display non-competitive inhibition
-
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0.0000063 - 0.00061
1-hydroxy-2-(1-naphthylmethyl)-3H-benzo[f]chromen-3-one
0.000006 - 0.002366
1-hydroxy-2-(2-naphthylmethyl)-3H-benzo[f]chromen-3-one
0.025
2,2'-dimethoxy-trans-stilbene
Mus musculus
-
above, pH not specified in the publication, 37°C
0.0051 - 0.0115
2,4'-dimethoxy-cis-stilbene
0.025
2,4'-dimethoxy-trans-stilbene
Mus musculus
-
above, pH not specified in the publication, 37°C
0.0023 - 0.0081
2,4,4'-trimethoxy-cis-stilbene
0.025
2,4,4'-trimethoxy-trans-stilbene
Mus musculus
-
above, pH not specified in the publication, 37°C
0.0103
2,6,4'-trimethoxy-trans-stilbene
Mus musculus
-
pH not specified in the publication, 37°C
0.000015 - 0.000465
2-benzyl-1-hydroxy-3H-benzo[f]chromen-3-one
0.025
2-hydroxy-4'-methoxy-trans-stilbene
Mus musculus
-
above, pH not specified in the publication, 37°C
0.00015 - 0.041
3,3'-(9H-fluoren-3-ylmethanediyl)bis(4-hydroxy-2H-chromen-2-one)
0.00088 - 0.0445
3,3'-(biphenyl-4-ylmethanediyl)bis(4-hydroxy-2H-chromen-2-one)
0.0013 - 0.0059
3,3'-(furan-2-ylmethanediyl)bis(4-hydroxy-2H-chromen-2-one)
0.000014 - 0.0085
3,3'-(naphthalen-2-ylmethanediyl)bis(4-hydroxy-2H-chromen-2-one)
0.0075 - 0.082
3,3'-(phenylmethanediyl)bis(4,7-dihydroxy-2H-chromen-2-one)
0.0042 - 0.021
3,3'-(phenylmethanediyl)bis(4-hydroxy-2H-chromen-2-one)
0.008 - 0.024
3,3'-(pyridin-2-ylmethanediyl)bis(4,7-dihydroxy-2H-chromen-2-one)
0.00038 - 0.018
3,3'-(quinolin-3-ylmethanediyl)bis(4-hydroxy-2H-chromen-2-one)
0.00055 - 0.01
3,3'-(thiophen-2-ylmethanediyl)bis(4-hydroxy-2H-chromen-2-one)
0.00035 - 0.06
3,3'-([4-[(E)-2-phenylethenyl]phenyl]methanediyl)bis(4-hydroxy-2H-chromen-2-one)
0.00058 - 0.005322
3,3'-butane-1,1-diylbis(4-hydroxy-2H-chromen-2-one)
0.000005 - 0.00035
3,3'-methanediylbis(4,7-dihydroxy-2H-chromen-2-one)
0.00000018 - 0.00037
3,3'-methanediylbis(4-hydroxy-2H-benzo[h]chromen-2-one)
0.0000026 - 0.000404
3,3'-methanediylbis(4-hydroxy-2H-chromen-2-one)
0.0000028 - 0.000038
3,3'-methanediylbis(4-hydroxy-5-methoxy-2H-chromen-2-one)
0.000062 - 0.001497
3,3'-methanediylbis(4-hydroxy-6,7-dimethoxy-2H-chromen-2-one)
0.00000041 - 0.000233
3,3'-methanediylbis(4-hydroxy-6,7-dimethyl-2H-chromen-2-one)
0.0000049 - 0.063
3,3'-methanediylbis(4-hydroxy-6,8-dibromo-2H-chromen-2-one)
0.000009 - 0.00625
3,3'-methanediylbis(4-hydroxy-6-chloro-2H-chromen-2-one)
0.0000045 - 0.0016
3,3'-methanediylbis(4-hydroxy-6-fluoro-2H-chromen-2-one)
0.000011 - 0.0033
3,3'-methanediylbis(4-hydroxy-6-methoxy-2H-chromen-2-one)
0.00000042 - 0.000149
3,3'-methanediylbis(4-hydroxy-7,8-dimethyl-2H-chromen-2-one)
0.0000038 - 0.00115
3,3'-methanediylbis(4-hydroxy-7-fluoro-2H-chromen-2-one)
0.000006 - 0.00079
3,3'-methanediylbis(4-hydroxy-7-methoxy-2H-chromen-2-one)
0.000014 - 0.0055
3,3'-methylenebis(4-hydroxy-6-methyl-2H-chromen-2-one)
0.0022 - 0.028
3,3'-[(4-chlorophenyl)methanediyl]bis(4-hydroxy-2H-chromen-2-one)
0.00065 - 0.01
3,3'-[(4-hydroxy-3-methoxyphenyl)methanediyl]bis(4-hydroxy-2H-chromen-2-one)
0.0023 - 0.035
3,3'-[(4-hydroxyphenyl)methanediyl]bis(4-hydroxy-2H-chromen-2-one)
0.00022 - 0.0087
3,3'-[(4-methoxyphenyl)methanediyl]bis(4-hydroxy-2H-chromen-2-one)
0.00125 - 0.05
3,3'-[[3,5-bis(benzyloxy)phenyl]methanediyl]bis(4-hydroxy-2H-chromen-2-one)
0.00035 - 0.0029
3,3'-[[4-(1-methylethyl)phenyl]methanediyl]bis(4-hydroxy-2H-chromen-2-one)
0.0001 - 0.005
3,3'-[[4-(dimethylamino)phenyl]methanediyl]bis(4-hydroxy-2H-chromen-2-one)
0.0044 - 0.0097
3,4'-dimethoxy-cis-stilbene
0.025
3,4'-dimethoxy-trans-stilbene
Mus musculus
-
above, pH not specified in the publication, 37°C
0.0023 - 0.007
3,4,4'-trimethoxy-cis-stilbene
0.025
3,4,4'-trimethoxy-trans-stilbene
Mus musculus
-
above, pH not specified in the publication, 37°C
0.000015 - 0.000034
3,4,5,4'-tetramethoxy-cis-stilbene
0.00016 - 0.001
3,4,5,4'-tetramethoxy-trans-stilbene
0.00012 - 0.00059
3,5,4'-trimethoxy-cis-stilbene
0.0011 - 0.0057
3,5,4'-trimethoxy-trans-stilbene
0.025
3,5-dihydroxy-4'-methoxy-cis-stilbene
Mus musculus
-
above, pH not specified in the publication, 37°C
0.025
3,5-dihydroxy-4'-methoxy-trans-stilbene
Mus musculus
-
above, pH not specified in the publication, 37°C
0.000255
3-(2,4-difluorophenoxymethyl)-6-methoxy-1,2-dimethylindole-4,7-dione
Homo sapiens
-
-
0.004654
3-(2-fluoro-4-nitrophenoxymethyl)-5-methoxy-1,2-dimethylindole-4,7-dione
Homo sapiens
-
-
0.000529
3-(2-fluoro-4-nitrophenoxymethyl)-6-methoxy-1,2-dimethylindole-4,7-dione
Homo sapiens
-
-
0.000031 - 0.0016
3-(3,4-dimethylbenzyl)-4-hydroxy-2H-chromen-2-one
0.0000099 - 0.000192
3-(3,4-dimethylbenzyl)-4-hydroxy-6,7-dimethyl-2H-chromen-2-one
0.000504
3-(4-aminophenoxymethyl)-6-methoxy-1,2-dimethylindole-4,7-dione
Homo sapiens
-
-
0.000463
3-(4-cyanophenoxymethyl)-6-methoxy-1,2-dimethylindole-4,7-dione
Homo sapiens
-
-
0.000905
3-(4-fluorophenoxymethyl)-6-methoxy-1,2-dimethylindole-4,7-dione
Homo sapiens
-
-
0.000035 - 0.00088
3-benzyl-4-hydroxy-2H-benzo[h]chromen-2-one
0.000144 - 0.0032
3-benzyl-4-hydroxy-2H-chromen-2-one
0.000039 - 0.00066
3-benzyl-4-hydroxy-6,7-dimethyl-2H-chromen-2-one
0.025
3-hydroxy-4'-methoxy-cis-stilbene
Mus musculus
-
above, pH not specified in the publication, 37°C
0.025
3-hydroxy-4'-methoxy-trans-stilbene
Mus musculus
-
above, pH not specified in the publication, 37°C
0.0034 - 0.025
3-hydroxy-4,4'-dimethoxy-cis-stilbene
0.025
3-hydroxy-4,4'-dimethoxy-trans-stilbene
Mus musculus
-
above, pH not specified in the publication, 37°C
0.002475
3-methoxy-1,2-dimethyl-3-(3-pyridyloxymethyl)indole-4,7-dione
Homo sapiens
-
-
0.0005 - 0.0225
3-[[3-[bis(4-hydroxy-2-oxo-2H-chromen-3-yl)methyl]phenyl](4-hydroxy-2-oxo-4a,8a-dihydro-2H-chromen-3-yl)methyl]-4-hydroxy-2H-chromen-2-one
0.00025 - 0.055
3-[[4-[bis(4-hydroxy-2-oxo-2H-chromen-3-yl)methyl]phenyl](4,7-dihydroxy-2-oxo-4a,8a-dihydro-2H-chromen-3-yl)methyl]-4,7-dihydroxy-2H-chromen-2-one
0.00011 - 0.02
3-[[4-[bis(4-hydroxy-2-oxo-2H-chromen-3-yl)methyl]phenyl](4-hydroxy-2-oxo-4a,8a-dihydro-2H-chromen-3-yl)methyl]-4-hydroxy-2H-chromen-2-one
0.025
4,4'-dimethoxy-cis-stilbene
Mus musculus
-
above, pH not specified in the publication, 37°C
0.025
4,4'-dimethoxy-trans-stilbene
Mus musculus
-
above, pH not specified in the publication, 37°C
0.00325 - 0.013
4-amino-2H-chromen-2-one
0.0000063 - 0.00045
4-hydroxy-3-(1-naphthylmethyl)-2H-benzo[h]chromen-2-one
0.000024 - 0.001522
4-hydroxy-3-(1-naphthylmethyl)-2H-chromen-2-one
0.0000022 - 0.000255
4-hydroxy-3-(2-naphthylmethyl)-2H-benzo[h]chromen-2-one
0.000014 - 0.001452
4-hydroxy-3-(2-naphthylmethyl)-2H-chromen-2-one
0.0000063 - 0.00045
4-hydroxy-3-(naphthalen-1-yl)cyclohepta[h]chromen-2(7H)-one
0.0000022 - 0.000225
4-hydroxy-3-(naphthalen-2-yl)cyclohepta[h]chromen-2(7H)-one
0.000035 - 0.00088
4-hydroxy-3-phenylcyclohepta[h]chromen-2(7H)-one
0.0000077 - 0.001095
4-hydroxy-6,7-dimethyl-3-(1-naphthylmethyl)-2H-chromen-2-one
0.0000025 - 0.000167
4-hydroxy-6,7-dimethyl-3-(2-naphthylmethyl)-2H-chromen-2-one
0.0000077 - 0.001095
4-hydroxy-6,7-dimethyl-3-(naphthalen-1-yl)-2H-chromen-2-one
0.0000025 - 0.000167
4-hydroxy-6,7-dimethyl-3-(naphthalen-2-yl)-2H-chromen-2-one
0.000039 - 0.00066
4-hydroxy-6,7-dimethyl-3-phenyl-2H-chromen-2-one
0.0017 - 0.021
4-[bis(4-hydroxy-2-oxo-2H-chromen-3-yl)methyl]benzoic acid
0.000427
5-methoxy-1,2-dimethyl-3-(2,4,6-trifluorophenoxymethyl)indole-4,7-dione
Homo sapiens
-
-
0.000345
5-methoxy-1,2-dimethyl-3-(2-nitrophenoxymethyl)indole-4,7-dione
Homo sapiens
-
-
0.000352
5-methoxy-1,2-dimethyl-3-(3-nitrophenoxymethyl)indole-4,7-dione
Homo sapiens
-
-
0.000904
5-methoxy-1,2-dimethyl-3-(3-pyridyloxymethyl)indole-4,7-dione
Homo sapiens
-
-
0.000629
5-methoxy-1,2-dimethyl-3-(4-nitrophenoxymethyl)indole-4,7-dione
Homo sapiens
-
-
0.001385
5-methoxy-1,2-dimethyl-3-(phenoxymethyl)indole-4,7-dione
Homo sapiens
-
-
0.002007
5-methoxy-1,2-dimethyl-3-(pyridin-4-yloxymethyl)indole-4,7-dione
Homo sapiens
-
-
0.001829
5-methoxy-1,2-dimethyl-3-[1-(4-nitrophenoxy)ethyl]indole-4,7-dione
Homo sapiens
-
-
0.000452
6-methoxy-1,2-dimethyl-3-(2,4,6-trifluorophenoxymethyl)indole-4,7-dione
Homo sapiens
-
-
0.000363
6-methoxy-1,2-dimethyl-3-(2-nitrophenoxymethyl)indole-4,7-dione
Homo sapiens
-
-
0.000351
6-methoxy-1,2-dimethyl-3-(3-nitrophenoxymethyl)indole-4,7-dione
Homo sapiens
-
-
0.000638
6-methoxy-1,2-dimethyl-3-(4-nitrophenoxymethyl)indole-4,7-dione
Homo sapiens
-
-
0.004563
6-methoxy-1,2-dimethyl-3-(phenoxymethyl)indole-4,7-dione
Homo sapiens
-
-
0.009579
6-methoxy-1,2-dimethyl-3-(pyridin-2-yloxymethyl)indole-4,7-dione
Homo sapiens
-
-
0.00256
6-methoxy-1,2-dimethyl-3-(pyridin-4-yloxymethyl)indole-4,7-dione
Homo sapiens
-
-
0.000496
6-methoxy-1,2-dimethyl-3-[4-(trifluoromethyl)phenoxymethyl]-indole-4,7-dione
Homo sapiens
-
-
0.00025 - 0.0006
7-(4-hydroxy-2-oxo-2H-chromen-3-yl)-6a,7-dihydro-4aH,6H,8H-pyrano[3,2-c:5,6-c']dichromene-6,8-dione
0.0002 - 0.00065
7-(4-hydroxy-2-oxo-2H-chromen-3-yl)-6H,7H-chromeno[4,3-b]chromen-6-one
1
alpha,alpha'-dipyridyl
Canis lupus familiaris
-
IC50: 1 mM
0.0000026 - 0.00045
dicoumarol
0.001221 - 0.02233
ethyl bis(4-hydroxy-2-oxo-2H-chromen-3-yl)acetate
0.0000063
1-hydroxy-2-(1-naphthylmethyl)-3H-benzo[f]chromen-3-one
Homo sapiens
without bovine serum albumin, in 50 mM phosphate buffer, at pH 7.5 and 25°C
0.00061
1-hydroxy-2-(1-naphthylmethyl)-3H-benzo[f]chromen-3-one
Homo sapiens
with 0.002 mM bovine serum albumin, in 50 mM phosphate buffer, at pH 7.5 and 25°C
0.000006
1-hydroxy-2-(2-naphthylmethyl)-3H-benzo[f]chromen-3-one
Homo sapiens
without bovine serum albumin, in 50 mM phosphate buffer, at pH 7.5 and 25°C
0.002366
1-hydroxy-2-(2-naphthylmethyl)-3H-benzo[f]chromen-3-one
Homo sapiens
with 0.002 mM bovine serum albumin, in 50 mM phosphate buffer, at pH 7.5 and 25°C
0.0051
2,4'-dimethoxy-cis-stilbene
Homo sapiens
-
pH not specified in the publication, 37°C, MCF-7 cells
0.0059
2,4'-dimethoxy-cis-stilbene
Homo sapiens
-
pH not specified in the publication, 37°C, HCT-116 cells
0.0104
2,4'-dimethoxy-cis-stilbene
Homo sapiens
-
pH not specified in the publication, 37°C, IMR-90 cells
0.0115
2,4'-dimethoxy-cis-stilbene
Mus musculus
-
pH not specified in the publication, 37°C
0.0023
2,4,4'-trimethoxy-cis-stilbene
Homo sapiens
-
pH not specified in the publication, 37°C, HCT-116 cells
0.0025
2,4,4'-trimethoxy-cis-stilbene
Homo sapiens
-
pH not specified in the publication, 37°C, MCF-7 cells
0.0056
2,4,4'-trimethoxy-cis-stilbene
Homo sapiens
-
pH not specified in the publication, 37°C, IMR-90 cells
0.0081
2,4,4'-trimethoxy-cis-stilbene
Mus musculus
-
pH not specified in the publication, 37°C
0.000015
2-benzyl-1-hydroxy-3H-benzo[f]chromen-3-one
Homo sapiens
without bovine serum albumin, in 50 mM phosphate buffer, at pH 7.5 and 25°C
0.000465
2-benzyl-1-hydroxy-3H-benzo[f]chromen-3-one
Homo sapiens
with 0.002 mM bovine serum albumin, in 50 mM phosphate buffer, at pH 7.5 and 25°C
0.00015
3,3'-(9H-fluoren-3-ylmethanediyl)bis(4-hydroxy-2H-chromen-2-one)
Homo sapiens
-
0.041
3,3'-(9H-fluoren-3-ylmethanediyl)bis(4-hydroxy-2H-chromen-2-one)
Homo sapiens
in the presence of bovine serum albumin
0.00088
3,3'-(biphenyl-4-ylmethanediyl)bis(4-hydroxy-2H-chromen-2-one)
Homo sapiens
-
0.0445
3,3'-(biphenyl-4-ylmethanediyl)bis(4-hydroxy-2H-chromen-2-one)
Homo sapiens
in the presence of bovine serum albumin
0.0013
3,3'-(furan-2-ylmethanediyl)bis(4-hydroxy-2H-chromen-2-one)
Homo sapiens
-
0.0059
3,3'-(furan-2-ylmethanediyl)bis(4-hydroxy-2H-chromen-2-one)
Homo sapiens
in the presence of bovine serum albumin
0.000014
3,3'-(naphthalen-2-ylmethanediyl)bis(4-hydroxy-2H-chromen-2-one)
Homo sapiens
-
0.0085
3,3'-(naphthalen-2-ylmethanediyl)bis(4-hydroxy-2H-chromen-2-one)
Homo sapiens
in the presence of bovine serum albumin
0.0075
3,3'-(phenylmethanediyl)bis(4,7-dihydroxy-2H-chromen-2-one)
Homo sapiens
-
0.082
3,3'-(phenylmethanediyl)bis(4,7-dihydroxy-2H-chromen-2-one)
Homo sapiens
in the presence of bovine serum albumin
0.0042
3,3'-(phenylmethanediyl)bis(4-hydroxy-2H-chromen-2-one)
Homo sapiens
-
0.021
3,3'-(phenylmethanediyl)bis(4-hydroxy-2H-chromen-2-one)
Homo sapiens
in the presence of bovine serum albumin
0.008
3,3'-(pyridin-2-ylmethanediyl)bis(4,7-dihydroxy-2H-chromen-2-one)
Homo sapiens
-
0.024
3,3'-(pyridin-2-ylmethanediyl)bis(4,7-dihydroxy-2H-chromen-2-one)
Homo sapiens
in the presence of bovine serum albumin
0.00038
3,3'-(quinolin-3-ylmethanediyl)bis(4-hydroxy-2H-chromen-2-one)
Homo sapiens
-
0.018
3,3'-(quinolin-3-ylmethanediyl)bis(4-hydroxy-2H-chromen-2-one)
Homo sapiens
in the presence of bovine serum albumin
0.00055
3,3'-(thiophen-2-ylmethanediyl)bis(4-hydroxy-2H-chromen-2-one)
Homo sapiens
-
0.01
3,3'-(thiophen-2-ylmethanediyl)bis(4-hydroxy-2H-chromen-2-one)
Homo sapiens
in the presence of bovine serum albumin
0.00035
3,3'-([4-[(E)-2-phenylethenyl]phenyl]methanediyl)bis(4-hydroxy-2H-chromen-2-one)
Homo sapiens
-
0.06
3,3'-([4-[(E)-2-phenylethenyl]phenyl]methanediyl)bis(4-hydroxy-2H-chromen-2-one)
Homo sapiens
in the presence of bovine serum albumin
0.00058
3,3'-butane-1,1-diylbis(4-hydroxy-2H-chromen-2-one)
Homo sapiens
without bovine serum albumin, in 50 mM phosphate buffer, at pH 7.5 and 25°C
0.005322
3,3'-butane-1,1-diylbis(4-hydroxy-2H-chromen-2-one)
Homo sapiens
with 0.002 mM bovine serum albumin, in 50 mM phosphate buffer, at pH 7.5 and 25°C
0.000005
3,3'-methanediylbis(4,7-dihydroxy-2H-chromen-2-one)
Homo sapiens
-
0.00035
3,3'-methanediylbis(4,7-dihydroxy-2H-chromen-2-one)
Homo sapiens
in the presence of bovine serum albumin
0.00000018
3,3'-methanediylbis(4-hydroxy-2H-benzo[h]chromen-2-one)
Homo sapiens
with 0.002 mM bovine serum albumin, in 50 mM phosphate buffer, at pH 7.5 and 25°C
0.00037
3,3'-methanediylbis(4-hydroxy-2H-benzo[h]chromen-2-one)
Homo sapiens
with 0.002 mM bovine serum albumin, in 50 mM phosphate buffer, at pH 7.5 and 25°C
0.0000026
3,3'-methanediylbis(4-hydroxy-2H-chromen-2-one)
Homo sapiens
-
without bovine serum albumin, at pH 7.5, 25°C
0.000404
3,3'-methanediylbis(4-hydroxy-2H-chromen-2-one)
Homo sapiens
-
with 0.14% (v/v) bovine serum albumin, at pH 7.5, 25°C
0.0000028
3,3'-methanediylbis(4-hydroxy-5-methoxy-2H-chromen-2-one)
Homo sapiens
-
without bovine serum albumin, at pH 7.5, 25°C
0.0000028
3,3'-methanediylbis(4-hydroxy-5-methoxy-2H-chromen-2-one)
Homo sapiens
without bovine serum albumin, in 50 mM phosphate buffer, at pH 7.5 and 25°C
0.000038
3,3'-methanediylbis(4-hydroxy-5-methoxy-2H-chromen-2-one)
Homo sapiens
with 0.002 mM bovine serum albumin, in 50 mM phosphate buffer, at pH 7.5 and 25°C
0.000038
3,3'-methanediylbis(4-hydroxy-5-methoxy-2H-chromen-2-one)
Homo sapiens
-
with 0.14% (v/v) bovine serum albumin, at pH 7.5, 25°C
0.000062
3,3'-methanediylbis(4-hydroxy-6,7-dimethoxy-2H-chromen-2-one)
Homo sapiens
-
without bovine serum albumin, at pH 7.5, 25°C
0.000062
3,3'-methanediylbis(4-hydroxy-6,7-dimethoxy-2H-chromen-2-one)
Homo sapiens
without bovine serum albumin, in 50 mM phosphate buffer, at pH 7.5 and 25°C
0.001497
3,3'-methanediylbis(4-hydroxy-6,7-dimethoxy-2H-chromen-2-one)
Homo sapiens
with 0.002 mM bovine serum albumin, in 50 mM phosphate buffer, at pH 7.5 and 25°C
0.001497
3,3'-methanediylbis(4-hydroxy-6,7-dimethoxy-2H-chromen-2-one)
Homo sapiens
-
with 0.14% (v/v) bovine serum albumin, at pH 7.5, 25°C
0.00000041
3,3'-methanediylbis(4-hydroxy-6,7-dimethyl-2H-chromen-2-one)
Homo sapiens
-
without bovine serum albumin, at pH 7.5, 25°C
0.00000041
3,3'-methanediylbis(4-hydroxy-6,7-dimethyl-2H-chromen-2-one)
Homo sapiens
without bovine serum albumin, in 50 mM phosphate buffer, at pH 7.5 and 25°C
0.000233
3,3'-methanediylbis(4-hydroxy-6,7-dimethyl-2H-chromen-2-one)
Homo sapiens
with 0.002 mM bovine serum albumin, in 50 mM phosphate buffer, at pH 7.5 and 25°C
0.000233
3,3'-methanediylbis(4-hydroxy-6,7-dimethyl-2H-chromen-2-one)
Homo sapiens
-
with 0.14% (v/v) bovine serum albumin, at pH 7.5, 25°C
0.0000049
3,3'-methanediylbis(4-hydroxy-6,8-dibromo-2H-chromen-2-one)
Homo sapiens
without bovine serum albumin, in 50 mM phosphate buffer, at pH 7.5 and 25°C
0.063
3,3'-methanediylbis(4-hydroxy-6,8-dibromo-2H-chromen-2-one)
Homo sapiens
with 0.002 mM bovine serum albumin, in 50 mM phosphate buffer, at pH 7.5 and 25°C
0.000009
3,3'-methanediylbis(4-hydroxy-6-chloro-2H-chromen-2-one)
Homo sapiens
without bovine serum albumin, in 50 mM phosphate buffer, at pH 7.5 and 25°C
0.00625
3,3'-methanediylbis(4-hydroxy-6-chloro-2H-chromen-2-one)
Homo sapiens
with 0.002 mM bovine serum albumin, in 50 mM phosphate buffer, at pH 7.5 and 25°C
0.0000045
3,3'-methanediylbis(4-hydroxy-6-fluoro-2H-chromen-2-one)
Homo sapiens
without bovine serum albumin, in 50 mM phosphate buffer, at pH 7.5 and 25°C
0.0016
3,3'-methanediylbis(4-hydroxy-6-fluoro-2H-chromen-2-one)
Homo sapiens
with 0.002 mM bovine serum albumin, in 50 mM phosphate buffer, at pH 7.5 and 25°C
0.000011
3,3'-methanediylbis(4-hydroxy-6-methoxy-2H-chromen-2-one)
Homo sapiens
-
without bovine serum albumin, at pH 7.5, 25°C
0.000011
3,3'-methanediylbis(4-hydroxy-6-methoxy-2H-chromen-2-one)
Homo sapiens
without bovine serum albumin, in 50 mM phosphate buffer, at pH 7.5 and 25°C
0.0033
3,3'-methanediylbis(4-hydroxy-6-methoxy-2H-chromen-2-one)
Homo sapiens
with 0.002 mM bovine serum albumin, in 50 mM phosphate buffer, at pH 7.5 and 25°C
0.0033
3,3'-methanediylbis(4-hydroxy-6-methoxy-2H-chromen-2-one)
Homo sapiens
-
with 0.14% (v/v) bovine serum albumin, at pH 7.5, 25°C
0.00000042
3,3'-methanediylbis(4-hydroxy-7,8-dimethyl-2H-chromen-2-one)
Homo sapiens
-
without bovine serum albumin, at pH 7.5, 25°C
0.00000042
3,3'-methanediylbis(4-hydroxy-7,8-dimethyl-2H-chromen-2-one)
Homo sapiens
without bovine serum albumin, in 50 mM phosphate buffer, at pH 7.5 and 25°C
0.000096
3,3'-methanediylbis(4-hydroxy-7,8-dimethyl-2H-chromen-2-one)
Homo sapiens
with 0.002 mM bovine serum albumin, in 50 mM phosphate buffer, at pH 7.5 and 25°C
0.000149
3,3'-methanediylbis(4-hydroxy-7,8-dimethyl-2H-chromen-2-one)
Homo sapiens
-
with 0.14% (v/v) bovine serum albumin, at pH 7.5, 25°C
0.0000038
3,3'-methanediylbis(4-hydroxy-7-fluoro-2H-chromen-2-one)
Homo sapiens
without bovine serum albumin, in 50 mM phosphate buffer, at pH 7.5 and 25°C
0.00115
3,3'-methanediylbis(4-hydroxy-7-fluoro-2H-chromen-2-one)
Homo sapiens
with 0.002 mM bovine serum albumin, in 50 mM phosphate buffer, at pH 7.5 and 25°C
0.000006
3,3'-methanediylbis(4-hydroxy-7-methoxy-2H-chromen-2-one)
Homo sapiens
-
without bovine serum albumin, at pH 7.5, 25°C
0.000006
3,3'-methanediylbis(4-hydroxy-7-methoxy-2H-chromen-2-one)
Homo sapiens
without bovine serum albumin, in 50 mM phosphate buffer, at pH 7.5 and 25°C
0.00079
3,3'-methanediylbis(4-hydroxy-7-methoxy-2H-chromen-2-one)
Homo sapiens
with 0.002 mM bovine serum albumin, in 50 mM phosphate buffer, at pH 7.5 and 25°C
0.00079
3,3'-methanediylbis(4-hydroxy-7-methoxy-2H-chromen-2-one)
Homo sapiens
-
with 0.14% (v/v) bovine serum albumin, at pH 7.5, 25°C
0.000014
3,3'-methylenebis(4-hydroxy-6-methyl-2H-chromen-2-one)
Homo sapiens
without bovine serum albumin, in 50 mM phosphate buffer, at pH 7.5 and 25°C
0.0055
3,3'-methylenebis(4-hydroxy-6-methyl-2H-chromen-2-one)
Homo sapiens
with 0.002 mM bovine serum albumin, in 50 mM phosphate buffer, at pH 7.5 and 25°C
0.0022
3,3'-[(4-chlorophenyl)methanediyl]bis(4-hydroxy-2H-chromen-2-one)
Homo sapiens
-
0.028
3,3'-[(4-chlorophenyl)methanediyl]bis(4-hydroxy-2H-chromen-2-one)
Homo sapiens
in the presence of bovine serum albumin
0.00065
3,3'-[(4-hydroxy-3-methoxyphenyl)methanediyl]bis(4-hydroxy-2H-chromen-2-one)
Homo sapiens
-
0.01
3,3'-[(4-hydroxy-3-methoxyphenyl)methanediyl]bis(4-hydroxy-2H-chromen-2-one)
Homo sapiens
in the presence of bovine serum albumin
0.0023
3,3'-[(4-hydroxyphenyl)methanediyl]bis(4-hydroxy-2H-chromen-2-one)
Homo sapiens
-
0.035
3,3'-[(4-hydroxyphenyl)methanediyl]bis(4-hydroxy-2H-chromen-2-one)
Homo sapiens
in the presence of bovine serum albumin
0.00022
3,3'-[(4-methoxyphenyl)methanediyl]bis(4-hydroxy-2H-chromen-2-one)
Homo sapiens
-
0.0087
3,3'-[(4-methoxyphenyl)methanediyl]bis(4-hydroxy-2H-chromen-2-one)
Homo sapiens
in the presence of bovine serum albumin
0.00125
3,3'-[[3,5-bis(benzyloxy)phenyl]methanediyl]bis(4-hydroxy-2H-chromen-2-one)
Homo sapiens
-
0.05
3,3'-[[3,5-bis(benzyloxy)phenyl]methanediyl]bis(4-hydroxy-2H-chromen-2-one)
Homo sapiens
in the presence of bovine serum albumin
0.00035
3,3'-[[4-(1-methylethyl)phenyl]methanediyl]bis(4-hydroxy-2H-chromen-2-one)
Homo sapiens
-
0.0029
3,3'-[[4-(1-methylethyl)phenyl]methanediyl]bis(4-hydroxy-2H-chromen-2-one)
Homo sapiens
in the presence of bovine serum albumin
0.0001
3,3'-[[4-(dimethylamino)phenyl]methanediyl]bis(4-hydroxy-2H-chromen-2-one)
Homo sapiens
-
0.005
3,3'-[[4-(dimethylamino)phenyl]methanediyl]bis(4-hydroxy-2H-chromen-2-one)
Homo sapiens
in the presence of bovine serum albumin
0.0044
3,4'-dimethoxy-cis-stilbene
Homo sapiens
-
pH not specified in the publication, 37°C, MCF-7 cells
0.0051
3,4'-dimethoxy-cis-stilbene
Homo sapiens
-
pH not specified in the publication, 37°C, HCT-116 cells
0.0095
3,4'-dimethoxy-cis-stilbene
Homo sapiens
-
pH not specified in the publication, 37°C, IMR-90 cells
0.0097
3,4'-dimethoxy-cis-stilbene
Mus musculus
-
pH not specified in the publication, 37°C
0.0023
3,4,4'-trimethoxy-cis-stilbene
Homo sapiens
-
pH not specified in the publication, 37°C, HCT-116 cells
0.0024
3,4,4'-trimethoxy-cis-stilbene
Homo sapiens
-
pH not specified in the publication, 37°C, MCF-7 cells
0.0051
3,4,4'-trimethoxy-cis-stilbene
Mus musculus
-
pH not specified in the publication, 37°C
0.007
3,4,4'-trimethoxy-cis-stilbene
Homo sapiens
-
pH not specified in the publication, 37°C, IMR-90 cells
0.000015
3,4,5,4'-tetramethoxy-cis-stilbene
Homo sapiens
-
pH not specified in the publication, 37°C, MCF-7 cells
0.00002
3,4,5,4'-tetramethoxy-cis-stilbene
Homo sapiens
-
pH not specified in the publication, 37°C, HCT-116 cells
0.00002
3,4,5,4'-tetramethoxy-cis-stilbene
Homo sapiens
-
pH not specified in the publication, 37°C, IMR-90 cells
0.000034
3,4,5,4'-tetramethoxy-cis-stilbene
Mus musculus
-
pH not specified in the publication, 37°C
0.00016
3,4,5,4'-tetramethoxy-trans-stilbene
Homo sapiens
-
pH not specified in the publication, 37°C, IMR-90 cells
0.00022
3,4,5,4'-tetramethoxy-trans-stilbene
Homo sapiens
-
pH not specified in the publication, 37°C, MCF-7 cells
0.00053
3,4,5,4'-tetramethoxy-trans-stilbene
Homo sapiens
-
pH not specified in the publication, 37°C, HCT-116 cells
0.001
3,4,5,4'-tetramethoxy-trans-stilbene
Mus musculus
-
pH not specified in the publication, 37°C
0.00012
3,5,4'-trimethoxy-cis-stilbene
Homo sapiens
-
pH not specified in the publication, 37°C, MCF-7 cells
0.00022
3,5,4'-trimethoxy-cis-stilbene
Homo sapiens
-
pH not specified in the publication, 37°C, HCT-116 cells
0.00023
3,5,4'-trimethoxy-cis-stilbene
Homo sapiens
-
pH not specified in the publication, 37°C, IMR-90 cells
0.00059
3,5,4'-trimethoxy-cis-stilbene
Mus musculus
-
pH not specified in the publication, 37°C
0.0011
3,5,4'-trimethoxy-trans-stilbene
Homo sapiens
-
pH not specified in the publication, 37°C, MCF-7 cells
0.0021
3,5,4'-trimethoxy-trans-stilbene
Homo sapiens
-
pH not specified in the publication, 37°C, IMR-90 cells
0.0052
3,5,4'-trimethoxy-trans-stilbene
Mus musculus
-
pH not specified in the publication, 37°C
0.0057
3,5,4'-trimethoxy-trans-stilbene
Homo sapiens
-
pH not specified in the publication, 37°C, HCT-116 cells
0.000031
3-(3,4-dimethylbenzyl)-4-hydroxy-2H-chromen-2-one
Homo sapiens
without bovine serum albumin, in 50 mM phosphate buffer, at pH 7.5 and 25°C
0.0016
3-(3,4-dimethylbenzyl)-4-hydroxy-2H-chromen-2-one
Homo sapiens
with 0.002 mM bovine serum albumin, in 50 mM phosphate buffer, at pH 7.5 and 25°C
0.0000099
3-(3,4-dimethylbenzyl)-4-hydroxy-6,7-dimethyl-2H-chromen-2-one
Homo sapiens
-
without bovine serum albumin, at pH 7.5, 25°C
0.0000099
3-(3,4-dimethylbenzyl)-4-hydroxy-6,7-dimethyl-2H-chromen-2-one
Homo sapiens
without bovine serum albumin, in 50 mM phosphate buffer, at pH 7.5 and 25°C
0.000192
3-(3,4-dimethylbenzyl)-4-hydroxy-6,7-dimethyl-2H-chromen-2-one
Homo sapiens
with 0.002 mM bovine serum albumin, in 50 mM phosphate buffer, at pH 7.5 and 25°C
0.000192
3-(3,4-dimethylbenzyl)-4-hydroxy-6,7-dimethyl-2H-chromen-2-one
Homo sapiens
-
with 0.14% (v/v) bovine serum albumin, at pH 7.5, 25°C
0.000035
3-benzyl-4-hydroxy-2H-benzo[h]chromen-2-one
Homo sapiens
without bovine serum albumin, in 50 mM phosphate buffer, at pH 7.5 and 25°C
0.00088
3-benzyl-4-hydroxy-2H-benzo[h]chromen-2-one
Homo sapiens
with 0.002 mM bovine serum albumin, in 50 mM phosphate buffer, at pH 7.5 and 25°C
0.000144
3-benzyl-4-hydroxy-2H-chromen-2-one
Homo sapiens
without bovine serum albumin, in 50 mM phosphate buffer, at pH 7.5 and 25°C
0.0032
3-benzyl-4-hydroxy-2H-chromen-2-one
Homo sapiens
with 0.002 mM bovine serum albumin, in 50 mM phosphate buffer, at pH 7.5 and 25°C
0.000039
3-benzyl-4-hydroxy-6,7-dimethyl-2H-chromen-2-one
Homo sapiens
without bovine serum albumin, in 50 mM phosphate buffer, at pH 7.5 and 25°C
0.00066
3-benzyl-4-hydroxy-6,7-dimethyl-2H-chromen-2-one
Homo sapiens
with 0.002 mM bovine serum albumin, in 50 mM phosphate buffer, at pH 7.5 and 25°C
0.0034
3-hydroxy-4,4'-dimethoxy-cis-stilbene
Homo sapiens
-
pH not specified in the publication, 37°C, HCT-116 cells
0.0042
3-hydroxy-4,4'-dimethoxy-cis-stilbene
Homo sapiens
-
pH not specified in the publication, 37°C, MCF-7 cells
0.006
3-hydroxy-4,4'-dimethoxy-cis-stilbene
Homo sapiens
-
pH not specified in the publication, 37°C, IMR-90 cells
0.025
3-hydroxy-4,4'-dimethoxy-cis-stilbene
Mus musculus
-
above, pH not specified in the publication, 37°C
0.0005
3-[[3-[bis(4-hydroxy-2-oxo-2H-chromen-3-yl)methyl]phenyl](4-hydroxy-2-oxo-4a,8a-dihydro-2H-chromen-3-yl)methyl]-4-hydroxy-2H-chromen-2-one
Homo sapiens
-
0.0225
3-[[3-[bis(4-hydroxy-2-oxo-2H-chromen-3-yl)methyl]phenyl](4-hydroxy-2-oxo-4a,8a-dihydro-2H-chromen-3-yl)methyl]-4-hydroxy-2H-chromen-2-one
Homo sapiens
in the presence of bovine serum albumin
0.00025
3-[[4-[bis(4-hydroxy-2-oxo-2H-chromen-3-yl)methyl]phenyl](4,7-dihydroxy-2-oxo-4a,8a-dihydro-2H-chromen-3-yl)methyl]-4,7-dihydroxy-2H-chromen-2-one
Homo sapiens
-
0.055
3-[[4-[bis(4-hydroxy-2-oxo-2H-chromen-3-yl)methyl]phenyl](4,7-dihydroxy-2-oxo-4a,8a-dihydro-2H-chromen-3-yl)methyl]-4,7-dihydroxy-2H-chromen-2-one
Homo sapiens
in the presence of bovine serum albumin
0.00011
3-[[4-[bis(4-hydroxy-2-oxo-2H-chromen-3-yl)methyl]phenyl](4-hydroxy-2-oxo-4a,8a-dihydro-2H-chromen-3-yl)methyl]-4-hydroxy-2H-chromen-2-one
Homo sapiens
-
0.02
3-[[4-[bis(4-hydroxy-2-oxo-2H-chromen-3-yl)methyl]phenyl](4-hydroxy-2-oxo-4a,8a-dihydro-2H-chromen-3-yl)methyl]-4-hydroxy-2H-chromen-2-one
Homo sapiens
in the presence of bovine serum albumin
0.00325
4-amino-2H-chromen-2-one
Homo sapiens
-
0.013
4-amino-2H-chromen-2-one
Homo sapiens
in the presence of bovine serum albumin
0.0000063
4-hydroxy-3-(1-naphthylmethyl)-2H-benzo[h]chromen-2-one
Homo sapiens
without bovine serum albumin, in 50 mM phosphate buffer, at pH 7.5 and 25°C
0.00045
4-hydroxy-3-(1-naphthylmethyl)-2H-benzo[h]chromen-2-one
Homo sapiens
with 0.002 mM bovine serum albumin, in 50 mM phosphate buffer, at pH 7.5 and 25°C
0.000024
4-hydroxy-3-(1-naphthylmethyl)-2H-chromen-2-one
Homo sapiens
without bovine serum albumin, in 50 mM phosphate buffer, at pH 7.5 and 25°C
0.001522
4-hydroxy-3-(1-naphthylmethyl)-2H-chromen-2-one
Homo sapiens
with 0.002 mM bovine serum albumin, in 50 mM phosphate buffer, at pH 7.5 and 25°C
0.0000022
4-hydroxy-3-(2-naphthylmethyl)-2H-benzo[h]chromen-2-one
Homo sapiens
without bovine serum albumin, in 50 mM phosphate buffer, at pH 7.5 and 25°C
0.000255
4-hydroxy-3-(2-naphthylmethyl)-2H-benzo[h]chromen-2-one
Homo sapiens
with 0.002 mM bovine serum albumin, in 50 mM phosphate buffer, at pH 7.5 and 25°C
0.000014
4-hydroxy-3-(2-naphthylmethyl)-2H-chromen-2-one
Homo sapiens
without bovine serum albumin, in 50 mM phosphate buffer, at pH 7.5 and 25°C
0.001452
4-hydroxy-3-(2-naphthylmethyl)-2H-chromen-2-one
Homo sapiens
with 0.002 mM bovine serum albumin, in 50 mM phosphate buffer, at pH 7.5 and 25°C
0.0000063
4-hydroxy-3-(naphthalen-1-yl)cyclohepta[h]chromen-2(7H)-one
Homo sapiens
-
without bovine serum albumin, at pH 7.5, 25°C
0.00045
4-hydroxy-3-(naphthalen-1-yl)cyclohepta[h]chromen-2(7H)-one
Homo sapiens
-
with 0.14% (v/v) bovine serum albumin, at pH 7.5, 25°C
0.0000022
4-hydroxy-3-(naphthalen-2-yl)cyclohepta[h]chromen-2(7H)-one
Homo sapiens
-
without bovine serum albumin, at pH 7.5, 25°C
0.000225
4-hydroxy-3-(naphthalen-2-yl)cyclohepta[h]chromen-2(7H)-one
Homo sapiens
-
with 0.14% (v/v) bovine serum albumin, at pH 7.5, 25°C
0.000035
4-hydroxy-3-phenylcyclohepta[h]chromen-2(7H)-one
Homo sapiens
-
without bovine serum albumin, at pH 7.5, 25°C
0.00088
4-hydroxy-3-phenylcyclohepta[h]chromen-2(7H)-one
Homo sapiens
-
with 0.14% (v/v) bovine serum albumin, at pH 7.5, 25°C
0.0000077
4-hydroxy-6,7-dimethyl-3-(1-naphthylmethyl)-2H-chromen-2-one
Homo sapiens
without bovine serum albumin, in 50 mM phosphate buffer, at pH 7.5 and 25°C
0.001095
4-hydroxy-6,7-dimethyl-3-(1-naphthylmethyl)-2H-chromen-2-one
Homo sapiens
with 0.002 mM bovine serum albumin, in 50 mM phosphate buffer, at pH 7.5 and 25°C
0.0000025
4-hydroxy-6,7-dimethyl-3-(2-naphthylmethyl)-2H-chromen-2-one
Homo sapiens
without bovine serum albumin, in 50 mM phosphate buffer, at pH 7.5 and 25°C
0.000167
4-hydroxy-6,7-dimethyl-3-(2-naphthylmethyl)-2H-chromen-2-one
Homo sapiens
with 0.002 mM bovine serum albumin, in 50 mM phosphate buffer, at pH 7.5 and 25°C
0.0000077
4-hydroxy-6,7-dimethyl-3-(naphthalen-1-yl)-2H-chromen-2-one
Homo sapiens
-
without bovine serum albumin, at pH 7.5, 25°C
0.001095
4-hydroxy-6,7-dimethyl-3-(naphthalen-1-yl)-2H-chromen-2-one
Homo sapiens
-
with 0.14% (v/v) bovine serum albumin, at pH 7.5, 25°C
0.0000025
4-hydroxy-6,7-dimethyl-3-(naphthalen-2-yl)-2H-chromen-2-one
Homo sapiens
-
without bovine serum albumin, at pH 7.5, 25°C
0.000167
4-hydroxy-6,7-dimethyl-3-(naphthalen-2-yl)-2H-chromen-2-one
Homo sapiens
-
with 0.14% (v/v) bovine serum albumin, at pH 7.5, 25°C
0.000039
4-hydroxy-6,7-dimethyl-3-phenyl-2H-chromen-2-one
Homo sapiens
-
without bovine serum albumin, at pH 7.5, 25°C
0.00066
4-hydroxy-6,7-dimethyl-3-phenyl-2H-chromen-2-one
Homo sapiens
-
with 0.14% (v/v) bovine serum albumin, at pH 7.5, 25°C
0.0017
4-[bis(4-hydroxy-2-oxo-2H-chromen-3-yl)methyl]benzoic acid
Homo sapiens
-
0.021
4-[bis(4-hydroxy-2-oxo-2H-chromen-3-yl)methyl]benzoic acid
Homo sapiens
in the presence of bovine serum albumin
0.00025
7-(4-hydroxy-2-oxo-2H-chromen-3-yl)-6a,7-dihydro-4aH,6H,8H-pyrano[3,2-c:5,6-c']dichromene-6,8-dione
Homo sapiens
-
0.0006
7-(4-hydroxy-2-oxo-2H-chromen-3-yl)-6a,7-dihydro-4aH,6H,8H-pyrano[3,2-c:5,6-c']dichromene-6,8-dione
Homo sapiens
in the presence of bovine serum albumin
0.0002
7-(4-hydroxy-2-oxo-2H-chromen-3-yl)-6H,7H-chromeno[4,3-b]chromen-6-one
Homo sapiens
-
0.00065
7-(4-hydroxy-2-oxo-2H-chromen-3-yl)-6H,7H-chromeno[4,3-b]chromen-6-one
Homo sapiens
in the presence of bovine serum albumin
0.0000026
dicoumarol
Homo sapiens
without bovine serum albumin, in 50 mM phosphate buffer, at pH 7.5 and 25°C
0.000005
dicoumarol
Homo sapiens
without bovine serum albumin
0.000404
dicoumarol
Homo sapiens
with 0.002 mM bovine serum albumin, in 50 mM phosphate buffer, at pH 7.5 and 25°C
0.00045
dicoumarol
Homo sapiens
in the presence of bovine serum albumin
0.001221
ethyl bis(4-hydroxy-2-oxo-2H-chromen-3-yl)acetate
Homo sapiens
without bovine serum albumin, in 50 mM phosphate buffer, at pH 7.5 and 25°C
0.02233
ethyl bis(4-hydroxy-2-oxo-2H-chromen-3-yl)acetate
Homo sapiens
with 0.002 mM bovine serum albumin, in 50 mM phosphate buffer, at pH 7.5 and 25°C
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biotechnology
the flavoprotein WrbA from Escherichia coli represents a new family of multimeric flavodoxin-like proteins implicated in cell protection against oxidative stress, WrbA has NAD(P)H: quinone reductase activity, forms multimers and binds FMN only weakly
degradation
-
TcpB is acting as a quinone reductase for 6-chlorohydroxyquinone reduction during 2,4,6-trichlorophenol degradation, a toxic pollutant
pharmacology
a series of lavendamycin analogues are tested in docking studies employing an X-ray derived NQO1 active site computational model, structure-based analogue design criteria are valid, resulting in the design of two analogues with high substrate specificity and selective toxicity toward NQO1-rich cells
analysis
-
method to measure enzyme inhibition in intact cells based on the resorufin reductase activity of enzyme. Values for 50% inhibition of enzyme by several reported in vivo inhibitors is at least three orders of magnitude higher for intact cells than for cell lysates
analysis
the enzyme is a catalyst for 1,4-dihydronicotinamide adenine dinucleotide-dependent amperometric biosensors and biofuel cells. For NADH detection, a linear range between 0.005 mM and 1 mM, a limit of detection of 0.003 mM, and a high sensitivity can be reached
analysis
development of a functional affinity-based small-molecule probe composed of a potent small-molecule NQO1 inhibitor 4-hydroxy-3-[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]-2H-1-benzopyran-2-one as the recognition group, a linker and the fluorophores group FITC. The probe exhibits good inhibitory activity of NQO1 and can be used to label the protein in A549 cells at the micromolar level
drug development
-
ability of ketoconazole and itraconazole to induce NQO1 gene expression at the transcriptional level through an aryl hydrocarbon receptor-dependent mechanism
drug development
-
cytoprotective effect of bromocriptine involving PI3K- and Nrf2-mediated upregulation of the antioxidant enzyme NQO1, which may be a therapeutic strategy to protect cells from oxidative damage in Parkinsons disease
drug development
design of novel lavendamycin analogues with enhanced, selective, and potent antitumor activity
drug development
-
greater induction activities of the phase II enzyme quinone reductase associated with stilbenoids serve as a useful starting point for the design of improved chemopreventive agents
drug development
-
in vitro, almond skin polyphenols act as antioxidants and induce quinone reductase activity, but these actions are dependent upon their dose, method of extraction, and interaction with antioxidant vitamins
drug development
-
induction of phase 2 enzymes, e.g. NQO1 increases resistance to chemical carcinogenesis. Isothiocyanates can therefore be valuable chemopreventative agents, and the specificity of these substances toward the urinary bladder suggest that they may be particularly useful for protecting against bladder cancer
drug development
-
mild temperature heat shock elevates the NQO1 expression in cancer cells, which in turn markedly increases the sensitivity of the cells to the bioreductive drug beta-lapachone in vitro and in vivo
drug development
-
mild temperature heat shock elevates the NQO1 expression in cancer cells, which in turn markedly increases the sensitivity of the cells to the bioreductive drug beta-lapachone in vitro and in vivo
drug development
-
NAD(P)H:quinone oxidoreductase is a major detoxifying enzyme for 7,12-dimethylbenz[a]anthracene. Eugenol has a potent protective effect against 7,12-dimethylbenz[a]anthracene-induced genotoxicity, presumably through the suppression of the 7,12-dimethylbenz[a]anthracene activation and the induction of its detoxification through NAD(P)H:quinone oxidoreductase
drug development
new coumarin-based competitive inhibitors of NQO1. NQO1 inhibition as an anticancer drug design target and superoxide generation as the dicoumarol-mediated mechanism of cytotoxicity
drug development
-
the enzyme is a valuable target for activating stimuli-responsive drug delivery systems based on quinone derivatives, such as prodrugs and liposomes
drug development
-
mild temperature heat shock elevates the NQO1 expression in cancer cells, which in turn markedly increases the sensitivity of the cells to the bioreductive drug beta-lapachone in vitro and in vivo
-
medicine
-
activation of antitumor prodrugs
medicine
-
acetaminophen is bioactivated by cytochrome P450 to the reactive intermediate N-acetyl-p-benzoquinone imine. Enhanced levels of hepatic enzyme may detoxify N-acetyl-p-benzoquinone imine by reducing it back to acetaminophen
medicine
-
antitumour quinones 2,5-diaziridinyl-3-hydroxymethyl-6-methyl-1,4-benzoquinone and 2,5-dimethyl-3,6-diaziridinyl-1,4-benzoquinone, i.e. RH1 and MeDZQ resp., induce apoptosis via enzyme-linked formation of alkylating species rather than via enzyme-linked redox cycling
medicine
-
ascorbic acid may potentiate the therapeutic efficacy of As3+ in treatment of acute promyelotic leukemia by enhancing the expression of enzyme together with heme oxygenase-1 and glutathione S-transferase Ya
medicine
-
clofibrate-mediated hepatoprotection against acetaminophen does not appear to be dependent upon enhanced expression of enzyme. Conditions of 94% inhobition of enzyme do not increase the susceptibility of hepatocytes from clofibrate treated mice to acetaminophen
medicine
-
enzyme is highly upregulated in active and chronic multiple sclerosis lesions, particularly in hypertrophic astrocytes and myelin-laden macrophages
medicine
-
enzyme protein is low in normal liver. Livers from patients with damage due to acetaminophen overdose or primary biliary cirrhosis show a strong induction of enzyme protein and activity
medicine
-
higher levels of enzyme expression in pancreatic adenocarcinomas compared to nontumourous tissues from nonsmokers. High levels are also found in pancreas of smokers and in pancreatitis tissues. No differences are found in genotype distribution and frequencies of the variant alleles between normal and cancer tissues. Use of enzyme expression as a biomarker for pancreatic cancer
medicine
-
presence of significant interethnic differences in polymorphic hepatic enzyme activity. Black donors show about twofold higher enzyme activity than white donors, and cytosolic enzyme activities differ significantly by enzyme genotype status in white, but not in black donors
medicine
-
statistically significant risk for colorectal cancer is associated with variant enzyme genotypes
medicine
-
NQO1 guards against oxidative stress and carcinogenesis and stabilizes p53, a homozygous common missense variant, NQO1*2, P187S that disables NQO1 predicts poor survival of women with breast cancer, NQO1 deficiency implicates cancer progression and treatment resistance to epirubicin, the NQO1 status is important for the response to epirubicin, ionizing radiation or 5-FU is not, NQO1 genotype is a prognostic and predictive marker for breast cancer
medicine
-
NQO1 polymorphism analysis is performed to investigate the relationship between prostate cancer and NQO1 C609T polymorphism in a turkish population, no correlation is found
medicine
-
NQO1 polymorphism analysis is performed using genomic DNA from blood samples, NQO1 polymorphisms, C/T and T/T genotypes, are associated with the risk of urothelial cancer, particularly among those who have ever smoked
medicine
-
NQO1 polymorphism analysis is performed using genomic DNA from buccal cell samples, anthracycline-related congestive heart failure is an important long-term complication among childhood cancer survivors, NQO1 polymorphism analysis indicated no association between the NQO1 polymorphism and the risk of anthracycline-related congestive heart failure
medicine
NQO1 polymorphism analysis is performed using genomic DNA from rectal biopsy samples, genotypes of C609T, T609T and C609C, G718G, A718A and A718G polymorphisms of NQO1 are compared, C609C genotype shows higher activity, C609T polymorphism is a important predictor for rectal NQO1 activity, fruit and vegetable consumption have no influence on NQO1 activity
medicine
-
series of indolequinones are synthesized and tested as inhibitors for NQO1 in pancreatic tumor cells, NQO1 inhibition does not correlate with growth inhibitory activity in MiaPaCa-2 cells
medicine
-
3-nitrobenzanthrone is capable to induce NQO1 and CYP1A1 in lungs and kidney of rats thereby enhancing its own genotoxic and carcinogenic potential
medicine
-
3H-1,2-dithiole-3-thione potently induces neuronal cellular GSH and NQO1 as well as mitochondrial GSH. Such upregulated endogenous defenses are accompanied by increased resistance to oxidative and electrophilic neurocytotoxicity, e.g. in Parkinson's disease
medicine
-
acute manganese intoxication, similarly to that of cadmium and other heavy metals, increases both the hepatic level of Nrf2 and its transfer from the cytoplasm to the nucleus where it actively regulates the induction of phase II enzymes, e.g. NQO1
medicine
-
dependence of copper neurotoxicity on DT-diaphorase inhibition
medicine
-
exposed workers to benzene in the petroleum refining industry with the T/T genotype for NQO1 show significant 1.9fold and 2.6fold increases in micronuclei and chromosome aberrations frequencies, respectively, compared to controls with C/C and C/T genotypes, after adjusting for age, smoking status, and alcohol intake
medicine
genetic variation, especially the NQO1 609CT polymorphism, is a more important predictor of rectal NQO1 phenotype than fruit and vegetable consumption. White blood cell NQO1 activity is not a good surrogate for rectal activity
medicine
individuals with the NQO1*2 allele are more susceptible to the toxic effects of benzene metabolites. Quinones that are good substrates for human NQO1 are more toxic to the NQO1 containing or expressing tumour cell lines than the NQO1-deficient cell lines. Quinones such as the biphenyl and naphthyl derivatives that are poor substrates show no selectivity or have no measurable cytotoxicity
medicine
-
main function of QR1 is probably the detoxification of dietary quinones but it may also contribute to the reduction of vitamin K for its involvement in blood coagluation
medicine
-
main function of QR1 is probably the detoxification of dietary quinones but it may also contribute to the reduction of vitamin K for its involvement in blood coagluation
medicine
-
main function of QR1 is probably the detoxification of dietary quinones but it may also contribute to the reduction of vitamin K for its involvement in blood coagluation
medicine
-
neuroprotective role of DT-diaphorase against aminochrome neurotoxicity
medicine
-
no association between NQO1 polymorphism and the risk of anthracycline-related congestive heart failure among childhood cancer survivors
medicine
-
NQO1 and SULT1A1 polymorphisms are associated with the risk of urothelial cancer, particularly among those who have ever smoked
medicine
-
NQO1 gene polymorphism influences interleukin-6 levels and therefore attenuates the inflammatory response after cardiopulmonary bypass
medicine
-
NQO1-induced bioreduction of beta-lap is an essential step in beta-lap-induced cell death. Combined radiotherapy and beta-lap treatment can have a significant effect on human tumor xenografts
medicine
-
plays a protective role against the induction of renal tumors by diethylstilbestrol
medicine
-
strain difference where Sprague Dawley rats possess a sex-dependent expression and activity of Nqo1 and August Copenhagen x Irish rats exhibit no sexual dimorphism may provide an important tool when using these rat models for oxidative stress and cancer studies
medicine
-
synthesis of novel heterocyclic quinones (benzimidazole- and benzothiazole-quinones) as excellent substrates for recombinant human NQO1
medicine
-
there is no significant relationship between NQO1 gene C609kT polymorphism and prostate cancer in a Turkish population, but an increased frequency of the TT genotype in patients compared to controls. Carrying the T allele may have an effect on serum prostate specific antigen and alkaline phosphatase levels in prostate cancer patients
medicine
-
trend toward lower drug response in patients with the NQO1 null genotype. Inhibiting NQO1 activity decreases p53 levels and drug induced apoptosis in chronic lymphocytic leukemia cells. NQO1 polymorphism may be a risk factor for chronic lymphocytic leukemia especially in males, and a predictor of response to chemotherapy
medicine
-
combination therapy employing a member of the group of non-cytotoxic NQO1 inhibitors together with a 2,6-dichlorophenolindophenol-like molecule may provide therapeutic efficacy against tumors that display high NQO1 enzymatic activity
medicine
isoform NQO1-KO mice exhibit a marked increase of permeability and spontaneous inflammation in the gut. In the dextran sulfate sodium salt-induced colitis model, NQO1-KO mice show more severe inflammatory responses than NQO1-wild-type mice. The transcript levels of claudin and occludin, the major tight junction molecules of gut epithelial cells, are significantly decreased in NQO1-KO mice. The colons of NQO1-KO mice also show high levels of reactive oxygen species and histone deacetylase activity
medicine
protein expression but not activity of NQO1 is weakly negatively correlated with age. No sex differences are observed for either protein expression or activity and for ethnicity. Caucasians have greater NQO1 activity than Asians. Overweight children have statistically significantly higher NQO1 activity as compared with ideal weight children
medicine
(+-)-dunnione and its ortho-quinone analogues act as substrates. The biological activity is favored by the presence of methyl group at the C ring and methoxy group at the A ring. The ortho-quinones exert their antitumor activity through NQO1-mediated reactive oxygen species production by redox cycling
medicine
development of an NQO1-targeted radiolabeled agent to establish an internal radiation therapy that amplifies the therapeutic effects when combined with external radiation therapy. The uptake of [125I]-marked compound 3-([[4-iodophenyl]thio]methyl)-5-methoxy-1,2-dimethyl-1H-indole-4,7-dione is specific and is dependent on the expression of NQO1. In NQO1-expressing tumor cells, over 85% of the initial radioactivity of [125I]-marked 3-([[4-iodophenyl]thio]methyl)-5-methoxy-1,2-dimethyl-1H-indole-4,7-dione is observed as an intact form at 1 h after incubation
medicine
in sub-chronic studies upon oral exposure to sulphoraphane for 30 days a 2- to 3fold increase in GSTM1, Gclc and NQO1 transcript levels, and a 2fold increase in NQO1 activity in adult livers is observed
medicine
levels of NQO1 protein and mRNA are significantly elevated in fresh tissue samples of small cell lung cancer. The rate of strong positive NQO1 protein expression is significantly higher in small cell lung cancer when compared with the rate in either adjacent non-cancerous or normal lung tissues and correlated with large tumor size, late pathologic stage and the presence of lymph node metastasis. High?level expression of NQO1 protein is significantly correlated with lower disease-free survival and 5-year survival rates in patients
medicine
low hepatic expression of the active glutathione S-transferases and NQO1 may increase the susceptibility of patients to amodiaquine idiosyncratic hepatotoxicity. NQO1 inactivates protein reactive quinonimines such as amodiaquine by reduction
medicine
natural polymorphism C609T may affect amrubicin-related pharmacokinetics and clinical outcomes in lung cancer treatment. At a dose of 40 mg/m2, the T/T genotype exhibits a tendency toward a relationship with decreased concentrations of amrubicinol on days 2 and 4 of treatment. The genotype also shows a significant decrease of hematological toxicities
medicine
NQO1 is highly expressed in normal melanocytes and in several melanoma cell lines in the presence of wild-type KEAP1, whose mutation elicits constitutive NRF2 activation and resistance to cisplatin. NQO1 expression is dependent on NRF2 activation. Synergistic cytotoxicity of HSP90 inhibitor 17-AAG, i.e. 17-(allylamino)-17-demethoxygeldanamycin, and cisplatin is detected in four out of five NQO1-low cell lines, but not in a cell line with KEAP1 mutation
medicine
NQO1 overexpression induces hepatocellular carcinoma cell apoptosis and proliferation inhibition through the AMPK/PGC-1a pathway
medicine
NQO1 overexpression is a main determinant for a potential chemotherapy resistance or an increased sensitivity to quinone-bearing compounds
medicine
-
clofibrate-mediated hepatoprotection against acetaminophen does not appear to be dependent upon enhanced expression of enzyme. Conditions of 94% inhobition of enzyme do not increase the susceptibility of hepatocytes from clofibrate treated mice to acetaminophen
-
additional information
-
ERbeta and hPMC2 are required for trans-hydroxytamoxifen-dependent recruitment of coactivators such as PARP-1 to the electrophile response element of NQO1 resulting in the induction of the antioxidative enzyme and subsequent protection against oxidative DNA damage
additional information
-
oxidative stress-type cytotoxicity of chromate in FLK cells may be partly attributed to its reduction by NQO1, but not by glutathione reductase
additional information
-
PIFI is a novel component essential for NDH-mediated nonphotochemical reduction of the plastoquinone pool in chlororespiratory electron transport
additional information
-
WrbA bridges flavodoxins and oxidoreductases. WrbA shows a close relationship to mammalian Nqo1