Information on EC 1.6.5.2 - NAD(P)H dehydrogenase (quinone)

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The expected taxonomic range for this enzyme is: Eukaryota, Archaea, Bacteria

EC NUMBER
COMMENTARY hide
1.6.5.2
-
RECOMMENDED NAME
GeneOntology No.
NAD(P)H dehydrogenase (quinone)
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
NAD(P)H + H+ + a quinone = NAD(P)+ + a hydroquinone
show the reaction diagram
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
oxidation
redox reaction
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-
-
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reduction
PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
Biosynthesis of secondary metabolites
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non-pathway related
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superpathway of photosynthetic hydrogen production
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Ubiquinone and other terpenoid-quinone biosynthesis
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-
SYSTEMATIC NAME
IUBMB Comments
NAD(P)H:quinone oxidoreductase
A flavoprotein. The enzyme catalyses a two-electron reduction and has a preference for short-chain acceptor quinones, such as ubiquinone, benzoquinone, juglone and duroquinone [6]. The animal, but not the plant, form of the enzyme is inhibited by dicoumarol.
CAS REGISTRY NUMBER
COMMENTARY hide
9032-20-6
-
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
ecotypes Col-0 and Col-gl1 wild-type, mutant line Salk_085656
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-
Manually annotated by BRENDA team
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Manually annotated by BRENDA team
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UniProt
Manually annotated by BRENDA team
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-
Manually annotated by BRENDA team
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-
Manually annotated by BRENDA team
amitochondriate eukaryote
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Manually annotated by BRENDA team
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-
Manually annotated by BRENDA team
strain ATCC51449
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Manually annotated by BRENDA team
strain ATCC51449
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-
Manually annotated by BRENDA team
Müll.-Arg.
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-
Manually annotated by BRENDA team
Hevea brasiliensis Mull.-Arg.
Müll.-Arg.
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Manually annotated by BRENDA team
C3H mice
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Manually annotated by BRENDA team
strain CD-1
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Manually annotated by BRENDA team
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Manually annotated by BRENDA team
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Manually annotated by BRENDA team
strain KT2440, gene chrR
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Manually annotated by BRENDA team
castor bean, enzymes DI and DII
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-
Manually annotated by BRENDA team
Sporotrichum pulverulentum
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Manually annotated by BRENDA team
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-
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Manually annotated by BRENDA team
Tinca vulgaris
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Manually annotated by BRENDA team
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UniProt
Manually annotated by BRENDA team
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Manually annotated by BRENDA team
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
physiological function
additional information
-
the homodimeric flavoprotein is unique among reductases, as it catalyzes the direct two-electron reduction of a wide variety quinones using NADH or NADPH as cofactor. Substrate docking studies, overview
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
1,4-benzoquinone + NAD(P)+
1,4-benzoquinol + NAD(P)+
show the reaction diagram
1,4-benzoquinone + NADPH
1,4-benzoquinol + NADP+
show the reaction diagram
-
-
-
-
?
1,4-dimethoxymethylbenzoquinone + NAD(P)H
1,4-dimethoxymethylhydrobenzoquinone + NAD(P)+
show the reaction diagram
-
-
-
?
1,4-naphthoquinone + NAD(P)H
1,4-naphthohydroquinone + NAD(P)+
show the reaction diagram
1,4-naphthoquinone + NAD(P)H
1,4-naphthohydroquinone + NADP+
show the reaction diagram
1,4-naphthoquinone + NADPH
1,4-naphthohydroquinol + NADP+
show the reaction diagram
-
-
-
-
?
1,4-naphthoquinone + NADPH
1,4-naphthoquinol
show the reaction diagram
-
-
-
-
?
1,4-naphthoquinone + NADPH
1,4-naphthoquinol + NADP+
show the reaction diagram
-
-
-
-
?
1,4-tetramethylbenzoquinone + NAD(P)H
1,4-tetramethylhydrobenzoquinone + NAD(P)+
show the reaction diagram
-
-
-
?
1,8-dihydroxy-9,10-anthraquinone + NADPH
1,8-dihydroxy-9,10-anthraquinol + NADP+
show the reaction diagram
-
-
-
-
?
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)+
show the reaction diagram
-
-
ratio kcat to Km value is 52000 per M and s
-
?
1-hydroxy-9,10-anthraquinone + NADPH
1-hydroxy-9,10-anthraquinol + NADP+
show the reaction diagram
-
-
-
-
?
17-(2-dimethylylamino)ethylamino-17-demethoxygeldanamycin + NAD(P)H + H+
reduced 17-(2-dimethylylamino)ethylamino-17-demethoxygeldanamycin + NADP+
show the reaction diagram
-
-
reduced component is a more potent Hsp90 inhibitor than parent benzoquinone ansamycin
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?
17-(2-pyrrolidin-1-yl)ethylamino-17-demethoxygeldanamycin + NAD(P)H + H+
reduced 17-(2-pyrrolidin-1-yl)ethylamino-17-demethoxygeldanamycin + NADP+
show the reaction diagram
-
-
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+
show the reaction diagram
-
-
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+
show the reaction diagram
-
-
reduced component is a more potent Hsp90 inhibitor than parent benzoquinone ansamycin
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?
2 ferricyanide + NAD(P)H
2 ferrocyanide + NAD(P)+ + H+
show the reaction diagram
2 ferricyanide + NADH
2 ferrocyanide + NAD+ + H+
show the reaction diagram
-
60% activity compared to the reactions of NADPH or NADH with 2,3-dimethoxy-5-methyl-1,4-benzoquinone
-
-
?
2,3,5,6-tetramethyl-1,4-benzoquinone + NAD(P)H
reduced 2,3,5,6-tetramethyl-1,4-benzoquinone + NAD(P)+
show the reaction diagram
-
-
-
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?
2,3-diglutathionyl-1,4-naphthoquinone + NADPH
2,3-diglutathionyl-1,4-naphthoquinol + NADP+
show the reaction diagram
-
-
-
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?
2,3-dihydroxy-5-methyl-1,4-benzoquinone + NAD(P)H
2,3-dihydroxy-5-methyl-1,4-benzoquinol + NAD(P)+
show the reaction diagram
2,3-dimethyl-1,4-naphthoquinone + NAD(P)H
2,3-dimethyl-1,4-hydronaphthoquinone + NAD(P)+
show the reaction diagram
-
-
-
?
2,4,6-trinitrotoluene + NAD(P)H +
reduced 2,4,6-trinitrotoluene + NAD(P)+
show the reaction diagram
-
-
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)+
show the reaction diagram
-
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)+
show the reaction diagram
-
excellent substrate
-
-
?
2,5-bis(ethylamine)-3,6-diaziridinyl-1,4-benzoquinone + NADPH
2,5-bis(ethylamine)-3,6-diaziridinyl-1,4-benzoquinol + NADP+
show the reaction diagram
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-
-
-
?
2,5-diaziridinyl-1,4-benzoquinone + NADPH
2,5-diaziridinyl-1,4-benzoquinol + NADP+
show the reaction diagram
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-
-
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?
2,5-diaziridinyl-3-(hydroxymethyl)-6-methyl-1,4-benzoquinone + NADPH
2,5-diaziridinyl-3-(hydroxymethyl)-6-methyl-1,4-benzoquinol + NADP+
show the reaction diagram
-
-
-
-
?
2,5-dihydroxy-1,4-naphthoquinone + NADPH
2,5-dihydroxy-1,4-naphthoquinol + NADP+
show the reaction diagram
-
-
-
-
?
2,5-dimethoxy-1,3-benzothiazole-4,7-dione + NAD(P)H
2,5-dimethoxy-1,3-benzothiazole-4,7-diol + NAD(P)+
show the reaction diagram
-
-
-
-
?
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)+
show the reaction diagram
-
-
-
-
?
2,5-dimethyl-1,4-benzoquinone + NADPH
2,5-dimethyl-1,4-benzoquinol + NADP+
show the reaction diagram
-
-
-
-
?
2,5-dimethyl-1,4-naphthoquinone + NADPH
2,5-dimethyl-1,4-naphthoquinol + NADP+
show the reaction diagram
-
-
-
-
?
2,5-dimethyl-3,6-diaziridinyl-1,4-benzoquinone + NADPH
2,5-dimethyl-3,6-diaziridinyl-1,4-benzoquinol + NADP+
show the reaction diagram
-
-
-
-
?
2,6-dimethoxybenzoquinone + NAD(P)H
2,6-dimethoxyhydrobenzoquinone + NAD(P)+
show the reaction diagram
-
-
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?
2,6-dimethyl-1,4-benzoquinone + NADPH
2,6-dimethyl-1,4-benzoquinol + NADP+
show the reaction diagram
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-
-
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?
2-acetoxymethyl-6-methoxy-1-methylbenzimidazole-4,7-dione + NADH
? + NAD+
show the reaction diagram
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-
-
-
?
2-chloro-6-hydroxy-1,4-benzoquinone + NADH
6-chlorobenzene-1,2,4-triol + NAD+
show the reaction diagram
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-
-
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?
2-ethyl-1,4-naphthoquinone + NAD(P)H
2-ethyl-1,4-hydronaphthoquinone + NAD(P)+
show the reaction diagram
-
-
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?
2-hydroxy-1,4-naphthoquinone + NADPH
2-hydroxy-1,4-naphthoquinol + NADP+
show the reaction diagram
-
-
-
-
?
2-hydroxymethyl-5-methoxy-1-methylbenzimidazole-4,7-dione + NADH
? + NAD+
show the reaction diagram
-
-
-
-
?
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)+
show the reaction diagram
-
-
-
?
2-hydroxymethyl-5-methoxybenzothiazole-4,7-dione + NADH
? + NAD+
show the reaction diagram
-
-
-
-
?
2-hydroxymethyl-6-methoxy-1-methylbenzimidazole-4,7-dione + NADH
? + NAD+
show the reaction diagram
-
-
-
-
?
2-methoxy-2,5-cyclohexadiene-1,4-dione + NAD(P)H
2-methoxy-2,5-cyclohexadiene-1,4-diol + NAD(P)+
show the reaction diagram
-
-
-
?
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)+
show the reaction diagram
-
-
-
?
2-methoxyquinone + NAD(P)H
2-methoxyhydroquinone + NAD(P)+
show the reaction diagram
Sporotrichum pulverulentum
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-
-
?
2-methyl-1,4-benzoquinone + NADPH
2-methyl-1,4-benzoquinol + NADP+
show the reaction diagram
-
-
-
-
?
2-methyl-1,4-naphthoquinone + NAD(P)H
2-methyl-1,4-dihydronaphthoquinone + NAD(P)+
show the reaction diagram
-
-
-
?
2-methyl-1,4-naphthoquinone + NAD(P)H
2-methyl-1,4-naphthoquinol + NAD(P)+
show the reaction diagram
2-methyl-1,4-naphthoquinone + NADH
2-methyl-1,4-naphthoquinol + NAD+
show the reaction diagram
2-methyl-1,4-naphthoquinone + NADPH
2-methyl-1,4-naphthoquinol + NADp+
show the reaction diagram
2-methyl-3-glutathionyl-5-hydroxy-1,4-naphthoquinone + NADPH
2-methyl-3-glutathionyl-5-hydroxy-1,4-naphthoquinol + NADP+
show the reaction diagram
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-
-
-
?
2-methyl-3-hydroxy-1,4-naphthoquinone + NADPH
2-methyl-3-hydroxy-1,4-naphthoquinol + NADP+
show the reaction diagram
-
-
-
-
?
2-methyl-3-phythyl-1,4-naphthoquinone + NAD(P)H
2-methyl-3-phythyl-1,4-naphthohydroquinone + NAD(P)+
show the reaction diagram
2-methyl-5-aziridinyl-1,4-benzoquinone + NADPH
2-methyl-5-aziridinyl-1,4-benzoquinol + NADP+
show the reaction diagram
-
-
-
-
?
2-methyl-5-hydroxy-1,4-naphthoquinone + NADPH
2-methyl-5-hydroxy-1,4-naphthoquinol + NADP+
show the reaction diagram
-
-
-
-
?
2-[nitro(2,4,6-trinitrophenyl)amino]ethyl nitrate + NAD(P)H +
reduced 2-[nitro(2,4,6-trinitrophenyl)amino]ethyl nitrate + NAD(P)+
show the reaction diagram
-
-
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)+
show the reaction diagram
-
trivial name beta-lapachone, potent cytotoxic agent against various cancer cell lines
-
?
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)+
show the reaction diagram
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)+
show the reaction diagram
-
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)+
show the reaction diagram
-
-
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)+
show the reaction diagram
-
-
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)+
show the reaction diagram
-
-
-
?
5,8-dihydroxy-1,4-naphthoquinone + NADPH
5,8-dihydroxy-1,4-naphthoquinol + NADP+
show the reaction diagram
-
-
-
-
?
5,8-dihydroxynaphthoquinone + NAD(P)H
5,8-dihydroxynaphthohydroquinone + NAD(P)+
show the reaction diagram
-
-
-
?
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)+
show the reaction diagram
5-(aziridin-1-yl)-2,4-dinitrobenzamide + NAD(P)H
5-(aziridin-1-yl)-4-hydroxylamino-2-nitrobenzamide + NAD(P)+
show the reaction diagram
5-(aziridin-1-yl)-2,4-dinitrobenzamide + reduced dihydronicotineamide riboside
5-(aziridin-1-yl)-4-hydroxylamino-2-nitrobenzamide + oxidized dihydronicotineamide riboside
show the reaction diagram
5-aziridin-1-yl-2,4-dinitrobenzamide + NAD(P)H + H+
5-aziridin-1-yl-4-(hydroxyamino)-2-nitrobenzamide
show the reaction diagram
-
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)+
show the reaction diagram
-
-
-
-
?
5-hydroxy-1,4-naphthoquinone + NADPH
5-hydroxy-1,4-naphthoquinol + NADP+
show the reaction diagram
-
-
-
-
?
5-methoxy-1,2-dimethyl-3-(hydroxymethyl)indole-4,7-dione + NADH
? + NAD+
show the reaction diagram
-
is efficiently metabolized by NQO1
-
-
?
5-methoxy-1,2-dimethyl-3-[(phenoxy)methyl]indole-4,7-dione + NADH
? + NAD+
show the reaction diagram
-
inefficient indolequinone substrate
-
-
?
5-methoxy-2-methylbenzothiazole-4,7-dione + NADH
? + NAD+
show the reaction diagram
-
-
-
-
?
6-hydroxydopaminequinone + NAD(P)H
6-hydroxydopaminehydroquinone + NAD(P)+
show the reaction diagram
-
-
-
?
6-hydroxydopaquinone + NAD(P)H
6-hydroxydopahydroquinone + NAD(P)+
show the reaction diagram
-
-
-
?
6-methoxy-1,2-dimethyl-3-(hydroxymethyl)indole-4,7-dione + NADH
? + NAD+
show the reaction diagram
-
is efficiently metabolized by NQO1
-
-
?
6-methoxy-1,2-dimethyl-3-[(phenoxy)methyl]indole-4,7-dione + NADH
? + NAD+
show the reaction diagram
-
inefficient indolequinone substrate
-
-
?
6-methoxy-1-methyl-2-(4-nitrophenoxymethyl)benzimidazole-4,7-dione + NADH
? + NAD+
show the reaction diagram
-
-
-
-
?
6-methoxy-1-methylbenzimidazole-4,7-dione + NADH
? + NAD+
show the reaction diagram
-
-
-
-
?
7-N-(2-furoyl)demethyllavendamycin methyl ester + NADH
? + NAD+
show the reaction diagram
poor substrate
-
-
?
7-N-acetyldemethyllavendamycin n-butyl amide + NADH
? + NAD+
show the reaction diagram
good substrate
-
-
?
7-N-acetyldemethyllavendamycin sec-butyl amide + NADH
? + NAD+
show the reaction diagram
poor substrate
-
-
?
9,10-anthraquinone-2,6-disulfonate + NADPH
? + NADP+
show the reaction diagram
-
-
-
-
?
9,10-anthraquinone-2-sulfonate + NADPH
? + NADP+
show the reaction diagram
-
-
-
-
?
9,10-phenanthrene quinone + NADPH
9,10-phenanthrene quinol + NADP+
show the reaction diagram
-
-
-
-
?
acetaminophen + NAD(P)H + H+
N-acetyl-p-benzoquinone imine + NAD(P)+
show the reaction diagram
-
-
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)+
show the reaction diagram
benzoquinone + NAD(P)+
benzohydroquinone + NAD(P)+
show the reaction diagram
benzoquinone + NADH
?
show the reaction diagram
-
-
-
-
?
benzo[a]pyrene 3,6-quinone + NAD(P)H
benzo[a]pyrene 3,6-quinol
show the reaction diagram
-
-
-
?
beta-lapachone + NAD(P)H
reduced beta-lapachone + NAD(P)+
show the reaction diagram
-
-
-
-
?
chromate(IV) + H2O
chromate(III) + H2O2
show the reaction diagram
-
-
-
-
?
chromate(VI) + H2O
chromate(III) + H2O2
show the reaction diagram
coenzyme Q0 + NAD(P)H
reduced coenzyme Q0 + NADP+
show the reaction diagram
coenzyme Q1 + NAD(P)H
reduced coenzyme Q1 + NADP+
show the reaction diagram
coenzyme Q1 + NADH
?
show the reaction diagram
-
-
-
-
?
coenzyme Q10 + NAD(P)H
reduced coenzyme Q10 + NAD(P)+
show the reaction diagram
-
-
-
?
cyclized-dopamine o-quinone + NAD(P)H
cyclized-dopamine o-hydroquinone + NADP+
show the reaction diagram
-
-
-
?
cytochrome C + menadione + NADH
? + reduced menadione + NAD+
show the reaction diagram
-
-
-
-
?
deamino-NADH + H+ + 2,3-dimethoxy-5-methyl-1,4-benzoquinone
deamino-NAD+ + 2,3-dimethoxy-5-methyl-1,4-benzoquinol
show the reaction diagram
-
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)+
show the reaction diagram
-
-
-
-
?
duroquinone + NAD(P)H
reduced duroquinone + NAD(P)+
show the reaction diagram
-
-
-
-
?
duroquinone + NADH
?
show the reaction diagram
-
-
-
-
?
duroquinone + NADH
? + NAD+
show the reaction diagram
duroquinone + NADPH
? + NADP+
show the reaction diagram
duroquinone + NADPH
durohydroquinone + NADP+
show the reaction diagram
-
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)+
show the reaction diagram
-
-
ratio kcat to Km value is 20000 per M and s
-
?
FAD + NADH
?
show the reaction diagram
-
-
-
-
?
ferricyanide + FAD + NADH
?
show the reaction diagram
-
-
-
-
?
ferricyanide + FMN + NADH
?
show the reaction diagram
-
-
-
-
?
FMN + NADH
?
show the reaction diagram
-
-
-
-
?
geldanamycin + NAD(P)H
reduced geldanamycin + NAD(P)+
show the reaction diagram
-
excellent substrate
-
-
?
geldanamycin + NAD(P)H + H+
reduced geldanamycin + NADP+
show the reaction diagram
-
-
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)+
show the reaction diagram
-
-
ratio kcat to Km value is 500000 per M and s
-
?
indolequinones + NAD(P)H
indolehydroquinones + NAD(P)+
show the reaction diagram
-
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)+
show the reaction diagram
juglone + NADH
dihydrojuglone + NAD+
show the reaction diagram
juglone + NADPH
dihydrojuglone + NADP+
show the reaction diagram
-
-
-
-
?
K3[Fe(CN)6] + NAD(P)H
K4[Fe(CN)6] + NAD(P)+
show the reaction diagram
lavendamycin beta-hydroxyethyl ester + NADH
? + NAD+
show the reaction diagram
good substrate
-
-
?
menadione + FAD + NADH
?
show the reaction diagram
-
-
-
-
?
menadione + FMN + NADH
?
show the reaction diagram
-
-
-
-
?
menadione + NAD(P)H
reduced menadione + NAD(P)+
show the reaction diagram
menadione + NAD(P)H
reduced menadione + NADP+
show the reaction diagram
-
-
-
-
?
menadione + NADH
?
show the reaction diagram
-
-
-
-
?
menadione + NADH
reduced menadione + NAD+
show the reaction diagram
menadione + NADH + H+
? + NAD+
show the reaction diagram
-
-
-
?
menadione + NADPH
reduced menadione + NADP+
show the reaction diagram
-
-
-
-
?
menadione + NADPH + H+
? + NADP+
show the reaction diagram
-
-
-
?
menadione + reduced nicotinamide 2-azidoadenine dinucleotide
reduced menadione + oxidized nicotinamide 2-azidoadenine dinucleotide
show the reaction diagram
-
-
-
?
menadione + reduced nicotinamide 8-azidoadenine dinucleotide
reduced menadione + oxidized nicotinamide 8-azidoadenine dinucleotide
show the reaction diagram
-
-
-
?
methoxyquinone + NAD(P)H
methoxyhydroquinone + NAD(P)+
show the reaction diagram
Sporotrichum pulverulentum
-
-
-
?
methyl red + NAD(P)H
reduced methyl red + NAD(P)+
show the reaction diagram
methyl-1,4-benzoquinone + NADPH + H+
methyl-1,4-benzoquinol + NADP+
show the reaction diagram
two-electron mechanism
-
-
?
methylene blue + NAD(P)H
reduced methylene blue + NAD(P)+
show the reaction diagram
-
-
-
?
mitomycin C + NAD(P)H
reduced mitomycin C + NAD(P)+
show the reaction diagram
-
poor substrate
-
-
?
mitomycin C + NADPH
? + NADP+
show the reaction diagram
-
-
-
-
?
N-methyl-N,2,4,6-tetranitroaniline + NAD(P)H +
reduced N-methyl-N,2,4,6-tetranitroaniline + NAD(P)+
show the reaction diagram
-
-
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)+
show the reaction diagram
-
-
ratio kcat to Km value is 52000 per M and s
-
?
NAD(P)H + H+ + 17-allylamino-demethoxygeldanamycin
NAD(P)+ + reduced 17-allylamino-demethoxygeldanamycin
show the reaction diagram
-
-
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
show the reaction diagram
-
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
show the reaction diagram
-
i.e. MeDZQ, induction of apoptosis via enzyme-linked formation of alkylating species
-
-
?
NAD(P)H + H+ + a quinone
NAD(P)+ + a hydroquinone
show the reaction diagram
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+ + oxidized 2,6-dichlorophenolindophenol
NAD(P)+ + reduced 2,6-dichlorophenolindophenol
show the reaction diagram
NAD(P)H + H+ + quinone
NAD(P)+ + hydroquinone
show the reaction diagram
-
-
-
-
?
NADH + decylubiquinone
NAD+ + decylubiquinol
show the reaction diagram
-
-
-
-
?
NADH + H+ + 1-[3,5-dinitro-2-(1,2,3,4-tetrahydronaphthalen-2-yl)phenyl]-1-oxohydrazinium
?
show the reaction diagram
-
-
-
-
?
NADH + H+ + 10-nitro-5,6-dihydrobenzimidazo[2,1-a]isoquinoline 12-oxide
?
show the reaction diagram
-
-
-
-
?
NADH + H+ + 10-nitro-5,6-dihydrobenzimidazo[2,1-a]isoquinoline-8-carboxamide 12-oxide
?
show the reaction diagram
-
-
-
-
?
NADH + H+ + 10-nitro-5,6-dihydrobenzimidazo[2,1-a]isoquinoline-9-carboxamide 12-oxide
?
show the reaction diagram
-
-
-
-
?
NADH + H+ + 17-(allylamino)-17-demethoxygeldanamycin
?
show the reaction diagram
NADH + H+ + 2,10-dinitro-5,6-dihydrobenzimidazo[2,1-a]isoquinoline 12-oxide
?
show the reaction diagram
-
-
-
-
?
NADH + H+ + 2,3-dimethoxy-5-methyl-1,4-benzoquinone
NAD+ + 2,3-dimethoxy-5-methyl-1,4-benzoquinol
show the reaction diagram
-
-
-
-
?
NADH + H+ + 2,4-dinitro-5-(1,2,3,4-tetrahydronaphthalen-2-yl)benzamide
?
show the reaction diagram
-
-
-
-
?
NADH + H+ + 2,4-dinitro-5-(5-nitro-1,2,3,4-tetrahydronaphthalen-2-yl)benzamide
?
show the reaction diagram
-
-
-
-
?
NADH + H+ + 2,4-dinitro-5-(7-nitro-1,2,3,4-tetrahydronaphthalen-2-yl)benzamide
?
show the reaction diagram
-
-
-
-
?
NADH + H+ + 2-(2,4,6-trinitrophenyl)-1,2,3,4-tetrahydronaphthalene
?
show the reaction diagram
-
-
-
-
?
NADH + H+ + 2-(2,4-dinitrophenyl)-1,2,3,4-tetrahydronaphthalene
?
show the reaction diagram
-
-
-
-
?
NADH + H+ + 2-(2,4-dinitrophenyl)-5-nitro-1,2,3,4-tetrahydronaphthalene
?
show the reaction diagram
-
-
-
-
?
NADH + H+ + 2-(3,5-dinitropyridin-2-yl)-1,2,3,4-tetrahydroisoquinoline
?
show the reaction diagram
-
-
-
-
?
NADH + H+ + 2-methyl-1,4-naphthoquinone
NAD+ + 2-methyl-1,4-naphthoquinol
show the reaction diagram
-
-
-
-
?
NADH + H+ + 2-[2,4-dinitro-6-(trifluoromethyl)phenyl]-1,2,3,4-tetrahydronaphthalene
?
show the reaction diagram
-
-
-
-
?
NADH + H+ + 2-[2,4-dinitro-6-(trifluoromethyl)phenyl]-5-nitro-1,2,3,4-tetrahydronaphthalene
?
show the reaction diagram
-
-
-
-
?
NADH + H+ + 2-[2,4-dinitro-6-(trifluoromethyl)phenyl]-7-nitro-1,2,3,4-tetrahydronaphthalene
?
show the reaction diagram
-
-
-
-
?
NADH + H+ + 3,5-dinitro-2-(1,2,3,4-tetrahydronaphthalen-2-yl)benzamide
?
show the reaction diagram
-
-
-
-
?
NADH + H+ + 3,5-dinitro-2-(1,2,3,4-tetrahydronaphthalen-2-yl)benzoic acid
?
show the reaction diagram
-
-
-
-
?
NADH + H+ + 3,5-dinitro-2-(7-nitro-1,2,3,4-tetrahydronaphthalen-2-yl)benzoic acid
?
show the reaction diagram
-
-
-
-
?
NADH + H+ + 4,10-dinitro-5,6-dihydrobenzimidazo[2,1-a]isoquinoline 12-oxide
?
show the reaction diagram
-
-
-
-
?
NADH + H+ + 4,10-dinitro-5,6-dihydrobenzimidazo[2,1-a]isoquinoline-9-carboxamide 12-oxide
?
show the reaction diagram
-
-
-
-
?
NADH + H+ + 4,10-dinitro-8-(trifluoromethyl)-5,6-dihydrobenzimidazo[2,1-a]isoquinoline 12-oxide
?
show the reaction diagram
-
-
-
-
?
NADH + H+ + 5,6-dihydro-10-nitropyrido[3'',2'':4',5']imidazo[2',1'-a]isoquinoline 12-oxide
?
show the reaction diagram
-
-
-
-
?
NADH + H+ + 5-(aziridin-1-yl)-2,4-dinitrobenzamide
?
show the reaction diagram
-
i.e. CB-1954
-
-
?
NADH + H+ + a quinone
NAD+ + a hydroquinone
show the reaction diagram
-
-
-
-
?
NADH + H+ + atovaquone
NAD+ + reduced atovaquone
show the reaction diagram
-
atovaquone is 2-[4-(4-chlorophenyl)cyclohexyl]-3-hydroxynaphthalene-1,4-dione
-
-
?
NADH + H+ + benzoquinone
NAD+ + benzoquinol
show the reaction diagram
-
-
-
-
?
NADH + H+ + coenzyme Q0
NAD+ + reduced coenzyme Q0
show the reaction diagram
-
-
-
-
?
NADH + H+ + coenzyme Q1
NAD+ + reduced coenzyme Q1
show the reaction diagram
-
-
-
-
?
NADH + H+ + dichlorophenolindophenol
NAD+ + reduced dichlorophenolindophenol
show the reaction diagram
-
-
-
-
?
NADH + H+ + duroquinone
NAD+ + duroquinol
show the reaction diagram
-
-
-
-
?
NADH + H+ + ubiquinone
NAD+ + ubiquinone
show the reaction diagram
-
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
show the reaction diagram
-
-
-
-
?
NADH + H+ + ubiquinone-1
NAD+ + ubiquinol-1
show the reaction diagram
-
-
-
-
?
NADH + H+ + ubiquinone-10
NAD+ + ubiquinol-10
show the reaction diagram
-
-
-
-
?
NADPH + H+ + 17-(allylamino)-17-demethoxygeldanamycin
?
show the reaction diagram
NADPH + H+ + 2,3-dimethoxy-5-methyl-1,4-benzoquinone
NADP+ + 2,3-dimethoxy-5-methyl-1,4-benzoquinol
show the reaction diagram
-
100% activity
-
-
?
NADPH + H+ + 2-methyl-1,4-naphthoquinone
NADP+ + 2-methyl-1,4-naphthoquinol
show the reaction diagram
-
-
-
-
?
NADPH + H+ + a quinone
NADP+ + a hydroquinone
show the reaction diagram
-
-
-
-
?
NADPH + H+ + benzoquinone
NADP+ + benzoquinol
show the reaction diagram
-
-
-
-
?
NADPH + H+ + duroquinone
NADP+ + duroquinol
show the reaction diagram
-
-
-
-
?
NADPH + H+ + oxidized 2,6-dichlorophenolindophenol
NADP+ + reduced 2,6-dichlorophenolindophenol
show the reaction diagram
NADPH + H+ + quinone
NADP+ + ?
show the reaction diagram
NADPH + H+ + ubiquinone-1
NADP+ + ubiquinol-1
show the reaction diagram
-
-
-
-
?
NADPH + H+ + ubiquinone-10
NADP+ + ubiquinol-10
show the reaction diagram
-
-
-
-
?
nitracrine + NAD(P)H +
reduced nitracrine + NAD(P)+
show the reaction diagram
-
-
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 dichlorophenol-indophenol + NAD(P)H
reduced dichlorophenol-indophenol + NADP+
show the reaction diagram
p-benzoquinone + NADH
benzohydroquinone + NAD+
show the reaction diagram
-
-
-
-
?
p-benzoquinone + NADPH
p-benzohydroquinone + NADP+
show the reaction diagram
-
-
-
-
?
plumbagin + NADH
? + NAD+
show the reaction diagram
-
-
-
-
?
plumbagin + NADPH
? + NADP+
show the reaction diagram
-
-
-
-
?
quinone + NAD(P)H
hydroquinone + NAD(P)+
show the reaction diagram
riboflavin + NADPH
? + NADP+
show the reaction diagram
-
-
-
-
?
streptonigrin + NAD(P)H
reduced streptonigrin + NAD(P)+
show the reaction diagram
-
one of the best substrates for NQO1
-
-
?
tetramethyl-1,4-benzoquinone + NADPH
tetramethyl-1,4-benzoquinol + NADP+
show the reaction diagram
-
-
-
-
?
toluquinone + NAD(P)H
toluhydroquinone + NAD(P)+
show the reaction diagram
Sporotrichum pulverulentum
-
-
-
?
ubiquinone + NAD(P)H
reduced ubiquinone + NAD(P)+
show the reaction diagram
ubiquinone-1 + NADPH + H+
ubiquinol-1 + NADP+
show the reaction diagram
-
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
reduced vitamin K + NAD(P)+
show the reaction diagram
-
-
-
?
vitamin K2 + NAD(P)H
reduced vitamin K2 + NAD(P)+
show the reaction diagram
-
-
-
?
[Fe(CN)6]3- + NAD(P)H
[Fe(CN)6]4- + NAD(P)+
show the reaction diagram
additional information
?
-
NATURAL SUBSTRATES
NATURAL PRODUCTS
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
NAD(P)H + H+ + a quinone
NAD(P)+ + a hydroquinone
show the reaction diagram
P15559
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
-
-
?
NADH + H+ + 17-(allylamino)-17-demethoxygeldanamycin
?
show the reaction diagram
-
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+ + 2-methyl-1,4-naphthoquinone
NAD+ + 2-methyl-1,4-naphthoquinol
show the reaction diagram
-
-
-
-
?
NADH + H+ + a quinone
NAD+ + a hydroquinone
show the reaction diagram
-
-
-
-
?
NADH + H+ + atovaquone
NAD+ + reduced atovaquone
show the reaction diagram
-
atovaquone is 2-[4-(4-chlorophenyl)cyclohexyl]-3-hydroxynaphthalene-1,4-dione
-
-
?
NADH + H+ + duroquinone
NAD+ + duroquinol
show the reaction diagram
-
-
-
-
?
NADH + H+ + ubiquinone
NAD+ + ubiquinone
show the reaction diagram
-
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
-
-
?
NADPH + H+ + 17-(allylamino)-17-demethoxygeldanamycin
?
show the reaction diagram
-
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+ + 2-methyl-1,4-naphthoquinone
NADP+ + 2-methyl-1,4-naphthoquinol
show the reaction diagram
-
-
-
-
?
NADPH + H+ + a quinone
NADP+ + a hydroquinone
show the reaction diagram
-
-
-
-
?
NADPH + H+ + duroquinone
NADP+ + duroquinol
show the reaction diagram
-
-
-
-
?
quinone + NAD(P)H
hydroquinone + NAD(P)+
show the reaction diagram
vitamin K + NAD(P)H
reduced vitamin K + NAD(P)+
show the reaction diagram
-
-
-
?
additional information
?
-
COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
deamino-NADH
-
-
flavin
-
flavoenzyme
NAD(P)H
Gly149, Tyr155 and His161 are directly involved in the electron transfer from NAD(P)H to FAD and from FADH2 to the quinone
NAD+
-
-
nicotinamide riboside
-
recombinant NAD(P)H:quinone acceptor oxidoreductase 2
additional information
-
trans-hydroxytamoxifen-dependent recruitment of coactivators ERbeta and hPMC2 to the electrophile response element sequence of NQO1. Trans-hydroxytamoxifen-dependent corecruitment of the coactivators Nrf2, PARP-1 and topoisomerase IIbeta, both in the presence and absence of ERalpha. Absence of either ERbeta or hPMC2 results in nonrecruitment of PARP-1 and topoisomerase IIbeta, loss of antioxidative enzyme induction and attenuated protection against oxidative DNA damage by trans-hydroxytamoxifen even in the presence of Nrf2 and ERalpha
-
METALS and IONS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
As3+
-
induction of enzyme together with heme oxygenase-1 and glutathione S-transferase Ya
Hg2+
-
increase of enzyme mRNA expression, via a transcriptional mechanism
Mn2+
-
strongly stimulates NQO1 in the liver of intoxicated rats
Pb2+
-
increase of enzyme mRNA expression, via a transcriptional mechanism
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
(A)-2-Azido-NAD+
-
photodependent inhibition
(A)-8-azido-NAD+
-
photodependent inhibition
1,10-phenanthroline
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
-
-
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
2,4-Dinitrophenol
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-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-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-Hydroxycoumarin
-
-
4-hydroxymercuribenzoate
-
0.067 mM, 50% inhibition
4-Methoxycoumarin
-
-
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
5,7-dihydroxyflavone
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
7,8-dihydroxyflavone
-
-
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-hydroxyflavone
-
-
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
acid blue 25
-
-
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
-
-
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
bis-3,3'-(4-hydroxycoumarinyl)acetoacetate
bromaminic acid
-
-
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
chrysin
Cibacron blue
Cibacron Blue F3G-A
-
0.04 mM, 75% inhibition
cis-stilbene
-
-
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
Dicoumarol dimethylether
-
0.0005, 50% inhibition
dicumarol
diphenylene iodonium chloride
-
-
EGTA
-
95% residual activity at 5 mM
ES 936
-
-
ethyl 5-aziridin-1-yl-2,4-dinitrobenzoate
-
competitive
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
iodoacetic acid
-
-
isorhamnetin
-
-
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
mitomycin C
morin
-
0.01 mM, 95% inhibition, recombinant NAD(P)H:quinone acceptor oxidoreductase 2
N-ethyl maleimide
-
0.33 mM, complete inhibition
N-ethylmaleimide
-
-
N-methyl-N,2,4,6-tetranitroaniline
-
competitive
N-methyl-N,2,4-trinitroaniline
-
competitive
nitracrine
-
competitive
p-chloromercuribenzoate
-
-
Phenindione
-
0.1 mM, 92% inhibition
phenylmercuric acetate
-
-
pinosylvin
-
-
Procion blue M-3GS
-
-
Procion blue MX-R
-
0.04 mM, 75% inhibition
quercetin
quinacrine dihydrochloride
-
0.05 mM, 65-95% inhibition depending on substrate
reserpine
-
competitive inhibitor of DT-diaphorase
resveratrol
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
-
-
trans-stilbene
-
-
-
vitamin E
-
-
warfarin
-
1 mM, 70% inhibition
additional information
ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
1,1'-(E)-ethene-1,2-diylbis(2-methoxybenzene)
-
at 12.5 micromol, induces quinone reductase to a greater extent than resveratrol
1,2-dithiole-3-thione
-
induces enzyme expression
1,3-dimethoxy-2-[(E)-2-(4-methoxyphenyl)ethenyl]benzene
-
at 12.5 micromol, induces quinone reductase to a greater extent than resveratrol
1-(3,4-dihydroxybenzyl)-1,2,3,4-tetrahydro-6,7-isoquinolinediol
-
up-regulation of enzyme upon exposure to L-dopa and tetrahydropapaveroline
1-methoxy-2-[(E)-2-(4-methoxyphenyl)ethenyl]benzene
-
at 6.3 micromol is 1.8 times more effective than resveratrol as a quinone reductase inducer
1-methoxy-3-[(E)-2-(4-methoxyphenyl)ethenyl]benzene
-
at 12.5 micromol, induces quinone reductase to a greater extent than resveratrol
2-mercaptoethanol
-
stimulates
2-methoxy-5-[(E)-2-(4-methoxyphenyl)ethenyl]phenol
-
at 12.5 micromol, induces quinone reductase to a greater extent than resveratrol
3-nitrobenzanthrone
-
increases protein level and enzymatic activity of NQO1. Up to a 2.5fold increase in NQO1 activity with menadione as substrate in tissues of rats treated with 3-nitrobenzanthrone
3H-1,2-dithiole-3-thione
-
significantly increases cellular NQO1 activity and mRNA levels. Induces NQO1 in a concentration-dependent manner. In SH-SY5Y cells, 2fold induction of cellular NQO1 with 0.01 mM and 3-5.5fold induction of NQO1 with 0.05 and 0.1 mM. 4.5fold increase of NQO1 mRNA between 12 and 24 h after treatment. 40% induction of cellular NQO1 after treatment of primary human neurons at a concentration of 0.01 mM
actinomycin D
-
treatment of the cells with actinomycin D alone for 6 h significantly inhibits the constitutive NQO1 mRNA level by approximately 80%. KTZ- and ITZ-mediated Nqo1 induction is completely inhibited
alpha-methylbenzyl isothiocyanate
-
in vivo, the organ most susceptible to the inductive activity of the isothiocyanates is the urinary bladder, with alpha-methylbenzyl isothiocyanate and cyclohexylmethyl isothiocyanate being the most effective. Inductive activity in the bladder in vivo does not correlate with that in bladder cells in vitro
ascorbic acid
-
superinduction of the enzyme induction by As3+
beta-napthoflavone
-
-
bromocriptine
-
significantly upregulates expression and activity (911% of untreated control) of NQO1, attenuates increase in protein-bound quinone in H2O2-treated PC12 cells, and protects PC12 cells against oxidative damage. Bromocriptine increases the expression and nuclear translocation of a basic leucine zipper transcription factor Nrf2, involved in the regulation of the enzyme
butylated hydroxyanisole
-
inducer
Clofibrate
cyclohexylmethyl isothiocyanate
-
in vivo, the organ most susceptible to the inductive activity of the isothiocyanates is the urinary bladder, with alpha-methylbenzyl isothiocyanate and cyclohexylmethyl isothiocyanate being the most effective. Inductive activity in the bladder in vivo does not correlate with that in bladder cells in vitro
cysteine
-
stimulates
desferrioxamine
-
stimulates the NADPH:chromate reductase reaction of NQO1
duroquinone
-
stimulates NQO1 activity
Eugenol
-
increases expression and activity of enzyme by NF-E2 related factor2 binding to antioxidant response element in enzyme gene; increases the expression and activity of NAD(P)H:quinone oxidoreductase through NF-E2 related factor2 binding to antioxidant response element in QR gene in a dose-dependent manner
GSH
-
maximal stimulation with 0.5 mM, approx. 3fold activity
isorhamnetin
-
-
itraconazole
-
induces NQO1 mRNA and enzymatic activity levels in a concentration- and time-dependent manner in wild-type but not aryl hydrocarbon receptor-deficient Hepa-1c1c7 cells. Increases NQO1 de novo RNA synthesis without significantly affecting the levels of existing RNA. 50 micromol shows maximum NQO1 mRNA induction
ketoconazole
-
induces NQO1 mRNA and enzymatic activity levels in a concentration- and time-dependent manner in wild-type but not aryl hydrocarbon receptor-deficient Hepa-1c1c7 cells. Increases NQO1 de novo RNA synthesis without significantly affecting the levels of existing RNA. 25 micromol shows maximum NQO1 mRNA induction
L-Dopa
-
up-regulation of enzyme upon exposure to L-dopa and tetrahydropapaveroline
oltipraz
quercetin
-
induces enzyme expression
resveratrol
-
at 25 micromol increases quinone reductase activity by 1.5fold. Resveratrol induces quinone reductase activity of the wild type Hepa-1c1c7 cells to the same extent as the mutant c1 cells that lack a phase I enzyme
rutaecarpine
-
induces enzyme activity and gene expression by transactivation of activator protein-1 in a dose-dependent manner; isolated from Evodia rutaecarpa, induces QR gene expression and activity through increase of activator protein-1, Evodia rutaecarpa is used in traditional Chinese medicine
sulforaphane
tert-butylhydroxy-anisole
-
induces enzyme expression
vitamin C
-
-
additional information
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.0058 - 0.037
1,4-benzoquinone
0.0233
2,6-dichloroindophenol
-
-