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Information on EC 1.6.5.2 - NAD(P)H dehydrogenase (quinone) and Organism(s) Homo sapiens
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1.6.5.2 NAD(P)H dehydrogenase (quinone)IUBMB Comments
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 . The animal, but not the plant, form of the enzyme is inhibited by dicoumarol.
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Word Map
- 1.6.5.2
- s-transferase
- dismutase
- oxygenase-1
- catalase
- gst
-
chemopreventive
-
detoxify
-
two-electron
- dicoumarol
-
2-related
-
erythroid
-
cytoprotective
- hydroquinone
-
bioreductive
- mitomycin
- sulforaphane
- isothiocyanate
- cyp1a1
- nitroreductase
-
decolor
- hepa
-
one-electron
-
glutamate-cysteine
-
benzoapyrene
-
nrf2-mediated
- semiquinone
-
chemoprotective
-
nadph-cytochrome
-
nrf2-dependent
-
kelch-like
-
drug-metabolizing
-
nf-e2-related
-
anticarcinogenic
- medicine
- glucosinolates
- plastoquinone
- nadph-d
-
textile
-
ech-associated
- 3-methylcholanthrene
-
xenobiotic-metabolizing
-
nrf2-are
-
udp-glucuronosyltransferase
-
erythroid-derived
-
ethoxyresorufin
- beta-naphthoflavone
- tert-butylhydroquinone
-
ferredoxin-nadp+
-
peitc
- pharmacology
- drug development
- analysis
- degradation
- methemoglobinemia
-
pentoxyresorufin
- biotechnology
The taxonomic range for the selected organisms is: Homo sapiens
The expected taxonomic range for this enzyme is: Bacteria, Eukaryota, Archaea
The expected taxonomic range for this enzyme is: Bacteria, Eukaryota, Archaea
Synonyms
dt-diaphorase, diaphorase, quinone reductase, azoreductase, nad(p)h:quinone oxidoreductase 1, nad(p)h:quinone oxidoreductase, nad(p)h dehydrogenase, nad(p)h quinone oxidoreductase 1, ndh complex, nad(p)h quinone oxidoreductase, 
more
topSYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
azoreductase
-
-
-
-
dehydrogenase, reduced nicotinamide adenine dinucleotide (phosphate, quinone)
-
-
-
-
diaphorase
-
-
-
-
DT-diaphorase
DTD
-
-
-
-
EC 1.6.99.2
flavoprotein NAD(P)H-quinone reductase
-
-
-
-
Menadione oxidoreductase
-
-
-
-
Menadione reductase
-
-
-
-
NAD(P)H dehydrogenase
-
-
-
-
NAD(P)H menadione reductase
-
-
-
-
NAD(P)H-quinone dehydrogenase
-
-
-
-
NAD(P)H-quinone oxidoreductase
NAD(P)H: (quinone-acceptor)oxidoreductase
-
-
-
-
NAD(P)H: menadione oxidoreductase
-
-
-
-
NAD(P)H: quinone oxidoreductase 1
NAD(P)H:quinone oxidoreductase
NAD(P)H:quinone oxidoreductase 1
NADH-menadione reductase
-
-
-
-
NADPH:quinone oxidoreductase 1
Naphthoquinone reductase
-
-
-
-
NQO1
p-Benzoquinone reductase
-
-
-
-
Phylloquinone reductase
-
-
-
-
QR1
QR2
-
-
-
-
Quinone reductase
-
-
-
-
quinone reductase 1
Reduced NAD(P)H dehydrogenase
-
-
-
-
reduced nicotinamide-adenine dinucleotide (phosphate) dehydrogenase
-
-
-
-
Viologen accepting pyridine nucleotide oxidoreductase
-
-
-
-
Vitamin K reductase
vitamin-K reductase
-
-
-
-
DT-diaphorase
-
-
-
-
NAD(P)H-quinone oxidoreductase
-
-
-
-
NAD(P)H:quinone oxidoreductase 1
-
-
NADPH:quinone oxidoreductase 1
-
wild type NQO1, variant NQO1*2 induces an amino acid change P187S
NQO1
-
-
QR1
-
-
-
-
Vitamin K reductase
-
-
-
-
REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
NAD(P)H + H+ + a quinone = NAD(P)+ + a hydroquinone
specific conformations of Y128 and F232 on the surface of the catalytic pocket are important for interaction of enzyme with p53 and other client proteins
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
oxidation
-
-
-
-
redox reaction
-
-
-
-
reduction
-
-
-
-
PATHWAY SOURCE
PATHWAYS
-
-, -
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
9032-20-6
-
SUBSTRATE
PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
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
-
?
2,3,3-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)+
-
-
-
?
2,5-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-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-(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-hydroxymethyl-5-methoxy-1-methylbenzimidazole-4,7-dione + NADH
? + NAD+
-
-
-
-
?
2-hydroxymethyl-6-methoxy-1-methylbenzimidazole-4,7-dione + NADH
? + NAD+
-
-
-
-
?
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 + NADPH
2-methyl-1,4-naphthoquinol + NADp+
-
-
-
-
?
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-(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
-
-
?
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-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-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-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+
-
-
-
-
?
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-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)+
-
-
-
?
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)+
-
-
-
?
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
-
?
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
-
?
lavendamycin beta-hydroxyethyl ester + NADH
? + NAD+
good substrate
-
-
?
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+
-
-
-
?
N-desethylamodiaquine + NAD+
N-desethylamodiaquine quinoneimine + NADH + H+
-
-
-
r
N-desethylamodiaquine quinoneimine + NADH + H+
N-desethylamodiaquine + NAD+
-
-
-
r
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+ + 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+ + oxidized 2,6-dichlorophenolindophenol
NAD(P)+ + reduced 2,6-dichlorophenolindophenol
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+ + 2,10-dinitro-5,6-dihydrobenzimidazo[2,1-a]isoquinoline 12-oxide
?
-
-
-
-
?
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-(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-[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
?
-
-
-
-
?
NADPH + H+ + oxidized 2,6-dichlorophenolindophenol
NADP+ + reduced 2,6-dichlorophenolindophenol
-
-
-
-
?
oxidized 2,6-dichlorophenolindophenol + NADH + H+
reduced 2,6-dichlorophenolindophenol + NAD+
-
-
-
-
r
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 dichlorophenolindophenol + NADH + H+
reduced dichlorophenolindophenol + NAD+
-
-
-
?
oxidized methyl red + reduced dihydronicotinamide riboside + H+
reduced methyl red + oxidized dihydronicotinamide riboside
-
-
-
-
r
streptonigrin + NAD(P)H
reduced streptonigrin + NAD(P)+
one of the best substrates for NQO1
-
-
?
menadione + NADH
reduced menadione + NAD+
-
-
-
-
?
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
-
-
-
-
?
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
-
-
?
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
-
-
?
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
-
-
?
NATURAL SUBSTRATE
NATURAL PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
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
-
-
?
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
-
-
?
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
-
-
?
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
-
-
?
COFACTOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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
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
-
FAD
absorption spectra of wild-type and mutant R139W with maxima at 375 and 450 nm
NADH
C-terminal domain forms part of the binding site for the hydrophilic regions of NADH
NADPH
C-terminal domain forms part of the binding site for the hydrophilic regions of NADPH
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
1-[3,5-dinitro-2-(1,2,3,4-tetrahydronaphthalen-2-yl)phenyl]-1-oxohydrazinium
-
-
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
-
-
3,3'-([4-[(E)-2-phenylethenyl]phenyl]methanediyl)bis(4-hydroxy-2H-chromen-2-one)
-
3,3'-[(4-hydroxy-3-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-(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)-6-methoxy-1,2-dimethylindole-4,7-dione
-
effective inhibitor of the growth of MiaPaCa-2 cells
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-([[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-[[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-9-carboxamide 12-oxide
-
-
4,10-dinitro-8-(trifluoromethyl)-5,6-dihydrobenzimidazo[2,1-a]isoquinoline 12-oxide
-
-
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
-
5,6-dimethylxanthenone-4-acetic acid
-
tumour blood flow inhibitor, competitive vs. NADH
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-(pyridin-2-yloxymethyl)indole-4,7-dione
-
indolequinone derivative 11, mechanism based 90% inhibition
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-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-(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-(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-(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-N-acetyldemethyllavendamycin n-butyl amide
lavendamycin analogue 12, selective toxic toward NQO1-rich cells
alpha-naphthoflavone
-
0.01 mM, 75% inhibition, recombinant NAD(P)H:quinone acceptor oxidoreductase 2
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
galangin
-
0.01 mM, 100% inhibition, recombinant NAD(P)H:quinone acceptor oxidoreductase 2
lavendamycin beta-hydroxyethyl ester
lavendamycin analogue 12, selective toxic toward NQO1-rich cells
morin
-
0.01 mM, 95% inhibition, recombinant NAD(P)H:quinone acceptor oxidoreductase 2
3,3'-methylene-bis(4-hydroxycoumarin)
-
0.01 mM, 25% inhibition, recombinant NAD(P)H:quinone acceptor oxidoreductase 2
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
chrysin
-
0.01 mM, 100% inhibition, recombinant NAD(P)H:quinone acceptor oxidoreductase 2
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
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
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
quercetin
-
0.01 mM, 100% inhibition, recombinant NAD(P)H:quinone acceptor oxidoreductase 2
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
-
ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
1-(3,4-dihydroxybenzyl)-1,2,3,4-tetrahydro-6,7-isoquinolinediol
up-regulation of enzyme upon exposure to L-dopa and tetrahydropapaveroline
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
Clofibrate
-
administration to animals for 5 to 10 days, increase in enzyme protein and activity
L-Dopa
up-regulation of enzyme upon exposure to L-dopa and tetrahydropapaveroline
eugenol
-
increases expression and activity of enzyme by NF-E2 related factor2 binding to antioxidant response element in enzyme gene
eugenol
-
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
additional information
-
heating at 42°C for 1 h significantly increases the expression of NQO1 in cancer cells
-
additional information
-
irradiation with 4 Gy causes a long-lasting upregulation of NQO1, thereby increasing NQO1-mediated beta-lap-induced cell deaths
-
additional information
-
vegetable consumption only is not associated with NQO1 mRNA level or NQO1 activity
-
additional information
vegetable consumption only is not associated with NQO1 mRNA level or NQO1 activity
-
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.025
5-(1-aziridinyl)-3-(hydroxymethyl)-2-(3-hydroxy-1-propenyl)-1-methyl-1H-indole-4,7-dione
-
-
0.012
oxidized 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium
-
recombinant NAD(P)H:quinone acceptor oxidoreductase 2
-
additional information
additional information
-
Michaelis-Menten kinetics and first-order rate constants with NADH and quinone substrates, overview
-
0.26
5-(aziridin-1-yl)-2,4-dinitrobenzamide
-
recombinant NAD(P)H:quinone acceptor oxidoreductase 2
1.37
5-(aziridin-1-yl)-2,4-dinitrobenzamide
-
recombinant NAD(P)H:quinone acceptor oxidoreductase 2
0.007
oxidized 2,6-dichloroindophenol
-
recombinant NAD(P)H:quinone acceptor oxidoreductase 2
0.018
oxidized 2,6-dichloroindophenol
-
recombinant NAD(P)H:quinone acceptor oxidoreductase 1
0.028
reduced dihydronicotinamide riboside
-
recombinant NAD(P)H:quinone acceptor oxidoreductase 2
-
0.07
reduced dihydronicotinamide riboside
-
recombinant NAD(P)H:quinone acceptor oxidoreductase 1
-
TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
11
oxidized 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium
-
recombinant NAD(P)H:quinone acceptor oxidoreductase 2
-
0.01
5-(aziridin-1-yl)-2,4-dinitrobenzamide
-
recombinant NAD(P)H:quinone acceptor oxidoreductase 2
6
5-(aziridin-1-yl)-2,4-dinitrobenzamide
-
recombinant NAD(P)H:quinone acceptor oxidoreductase 2
46.7
oxidized 2,6-dichlorophenolindophenol
-
recombinant NAD(P)H:quinone acceptor oxidoreductase 2
600
oxidized 2,6-dichlorophenolindophenol
-
recombinant NAD(P)H:quinone acceptor oxidoreductase 1
43.3
reduced dihydronicotinamide riboside
-
recombinant NAD(P)H:quinone acceptor oxidoreductase 2
-
517
reduced dihydronicotinamide riboside
-
recombinant NAD(P)H:quinone acceptor oxidoreductase 1
-
kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
1900
2,3,3-trimethyl-2,3-dihydronaphtho[1,2-b]furan-4,5-dione
pH not specified in the publication, temperature not specified in the publication
-
3100
8-methoxy-2,3,3-trimethyl-2,3-dihydronaphtho[1,2-b]furan-4,5-dione
pH not specified in the publication, temperature not specified in the publication
-
2400
9-methoxy-2,3,3-trimethyl-2,3-dihydronaphtho[1,2-b]furan-4,5-dione
pH not specified in the publication, temperature not specified in the publication
-
Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.00045
5-methoxy-1,2-dimethyl-3-[(4-nitrophenoxy)methyl]indole-4,7-dione
-
IC50 VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.00035 - 0.06
3,3'-([4-[(E)-2-phenylethenyl]phenyl]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)
0.00125 - 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)
0.000255
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
-
-
0.0005 - 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
0.000427
5-methoxy-1,2-dimethyl-3-(2,4,6-trifluorophenoxymethyl)indole-4,7-dione
Homo sapiens
-
-
0.000452
6-methoxy-1,2-dimethyl-3-(2,4,6-trifluorophenoxymethyl)indole-4,7-dione
Homo sapiens
-
-
0.000496
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
0.0000063
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
0.0023
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
0.000015
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
0.0445
3,3'-(biphenyl-4-ylmethanediyl)bis(4-hydroxy-2H-chromen-2-one)
Homo sapiens
in the presence of bovine serum albumin
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
0.082
3,3'-(phenylmethanediyl)bis(4,7-dihydroxy-2H-chromen-2-one)
Homo sapiens
in the presence of bovine serum albumin
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
0.018
3,3'-(quinolin-3-ylmethanediyl)bis(4-hydroxy-2H-chromen-2-one)
Homo sapiens
in the presence of bovine serum albumin
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
0.00035
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
0.0023
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
0.007
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
0.00016
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
0.00012
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
0.0011
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
0.0057
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
0.0005
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
0.0000063
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
0.021
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
0.000404
dicoumarol
Homo sapiens
with 0.002 mM bovine serum albumin, in 50 mM phosphate buffer, at pH 7.5 and 25°C
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
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
0.001
0.0014
-
recombinant enzyme NQO1, substrate 10k, pH not specified in the publication, 37°C
0.0062
-
recombinant enzyme NQO1, substrate 5-(aziridin-1-yl)-2,4-dinitrobenzamide, i.e. CB-1954, pH not specified in the publication, 37°C
0.011
-
recombinant enzyme NQO1, substrate 10c, pH not specified in the publication, 37°C
0.013
-
recombinant enzyme NQO1, substrate 2-(3,5-dinitropyridin-2-yl)-1,2,3,4-tetrahydroisoquinoline, pH not specified in the publication, 37°C
0.016
-
recombinant enzyme NQO1, substrate 11a, pH not specified in the publication, 37°C
0.02
-
recombinant enzyme NQO1, substrate 10n, pH not specified in the publication, 37°C
0.038
-
recombinant enzyme NQO1, substrate 10j, pH not specified in the publication, 37°C
0.042
-
recombinant enzyme NQO1, substrate 10e, pH not specified in the publication, 37°C
0.053
-
recombinant enzyme NQO1, substrate 10d, pH not specified in the publication, 37°C
0.076
-
recombinant enzyme NQO1, substrate 10m, pH not specified in the publication, 37°C
0.11
-
recombinant enzyme NQO1, substrate 10b, pH not specified in the publication, 37°C
0.17
-
recombinant enzyme NQO1, substrate 5,6-dihydro-10-nitropyrido[3'',2'':4',5']imidazo[2',1'-a]isoquinoline 12-oxide, pH not specified in the publication, 37°C
280
pH not specified in the publication, temperature not specified in the publication
38.1
substrate 3-(hydroxymethyl)-5-methoxy-1-methyl-1H-indazole-4,7-dione, pH 7.4, 22°C
53.9
substrate methyl 5-methoxy-4,7-dioxo-4,7-dihydro-1-benzothiophene-2-carboxylate, pH 7.4, 22°C
63.8
substrate 5-methoxy-4,7-dioxo-4,7-dihydro-1-benzothiophene-2-carboxylic acid, pH 7.4, 22°C
80.8
substrate 2-(1-hydroxyethyl)-5-methoxy-3-methyl-1-benzofuran-4,7-dione, pH 7.4, 22°C
87.9
substrate 3-(1-hydroxyethyl)-5-methoxy-2-methyl-1-benzofuran-4,7-dione, pH 7.4, 22°C
0.001
-
below, recombinant enzyme NQO1, substrate 10a, pH not specified in the publication, 37°C
0.001
-
below, recombinant enzyme NQO1, substrate 10f, pH not specified in the publication, 37°C
0.001
-
below, recombinant enzyme NQO1, substrate 10g, pH not specified in the publication, 37°C
0.001
-
below, recombinant enzyme NQO1, substrate 10h, pH not specified in the publication, 37°C
0.001
-
below, recombinant enzyme NQO1, substrate 10o, pH not specified in the publication, 37°C
0.001
-
below, recombinant enzyme NQO1, substrate 11d, pH not specified in the publication, 37°C
0.001
-
below, recombinant enzyme NQO1, substrate 11e, pH not specified in the publication, 37°C
0.001
-
below, recombinant enzyme NQO1, substrate 11h, pH not specified in the publication, 37°C
0.001
-
below, recombinant enzyme NQO1, substrate 11i, pH not specified in the publication, 37°C
0.001
-
below, recombinant enzyme NQO1, substrate 11k, pH not specified in the publication, 37°C
0.001
-
below, recombinant enzyme NQO1, substrate 11l, pH not specified in the publication, 37°C
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
-
SwissProt
patients with congestive heart failure after anthracycline treatment during childhood
-
-
patients with liver damage due to acetaminophen overdose or primary biliary cirrhosis
-
-
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
SOURCE
-
low NQO1 activity. The redox dye 2,6-dichlorophenolindophenol may serve as a prooxidant chemotherapeutic targeting human melanoma cells in vitro and in vivo. DCPIP-apoptogenicity observed in the human melanoma cell lines A375 and G361 is inversely correlated with NAD(P)H:quinone oxidoreductase (NQO1) expression levels. 2,6-Dichlorophenolindophenol apoptogenic potency observed in human A375 and G361 melanoma cells is a function of cellular NQO1 expression levels
-
enzyme is highly upregulated in active and chronic multiple sclerosis lesions, particularly in hypertrophic astrocytes and myelin-laden macrophages
-
wild-type p53immortalized B-cell lymphoblasts from individuals with heterozygous NQO1; homozygous NQO1+/- and missing NQO1, LBL51
-
the ratio of frontal to cerebellar NQO1 activity is significantly increased in patients with Alzheimers disease versus controls, specific localization to astrocytes and neurites surrounding senile plaques. Neuronal NQO1 staining seen in frontal cortex of Alzheimers disease patients is absent in frontal cortex of controls, but is found to the same extent in neurons of the substantia nigra of both Alzheimers disease patients and controls
-
the ratio of frontal to cerebellar NQO1 activity is significantly increased in patients with Alzheimers disease versus controls
-
the ratio of frontal to cerebellar NQO1 activity is significantly increased in patients with Alzheimers disease versus controls
-
the redox dye 2,6-dichlorophenolindophenol may serve as a prooxidant chemotherapeutic targeting human melanoma cells in vitro and in vivo. DCPIP-apoptogenicity observed in the human melanoma cell lines A375 and G361 is inversely correlated with NAD(P)H:quinone oxidoreductase (NQO1) expression levels. 2,6-Dichlorophenolindophenol apoptogenic potency observed in human A375 and G361 melanoma cells is a function of cellular NQO1 expression levels
up-regulation of enzyme upon exposure to L-dopa and tetrahydropapaveroline
no correlation between NQO1 activity in rectal biopsies and NQO1 activity in total lymphocytes. No correlation between total leukocyte and lymphocyte NQO1 activity
-
enzyme is highly upregulated in active and chronic multiple sclerosis lesions, particularly in hypertrophic astrocytes and myelin-laden macrophages
-
human breast cancer cell line lacking enzyme due to genetic polymorphism
additional information
BE human colon adenocarcinoma cells, stably NQO1-transfected BE-NQ cells69
no correlation between NQO1 activity in rectal biopsies and NQO1 activity in total leukocytes. No correlation between total leukocyte and lymphocyte NQO1 activity
-
patients with liver damage due to acetaminophen overdose or primary biliary cirrhosis
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
-
wild-type p53 breast cancer cell lines MCF7 transfected with MCF7-NQO1 to overexpress NQO1, MCF7-SUP8 to knockdown NQO1
oxidative stress-resistant MCF-7 breast cancer cells, derived from MCF-7 cells, which were rendered resistant by chronic exposure to an H2O2-generating system made by mixing a redox cycler (menadione) with a reducing agent such as ascorbate.
-
The stably transfected Panc-1/C5 cell line expressing NQO1 was generated from Panc-1 cells by electroporation with an elongation factor 1alpha-driven internal ribosome entry site expression vector containing full-length human NQO1-1 cDNA.
upregulation or overexpression of the enzyme in tumours
rectal activity is higher among NQO1 609CC-genotypes as compared to 609CT-genotypes, whereas mRNA is higher among 609CT-genotypes. Activity and mRNA correlate among NQO1 609CC-genotypes but not among 609CT-genotypes
additional information
-
NQO1 is not detected in the acute myelogenous leukemia cell line MV4:11 or in the non-small cell lung cancer cell line HCC-4006
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY
GeneOntology No.
LITERATURE
SOURCE
additional information
-
NQO1 is located mainly in the cytosol of cells, but can be found also in the nucleus, endoplasmic reticulum, cellular membrane, and mitochondria, as well as extracellularly
-
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY
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
physiological function
-
artificial overexpression of NQO1 is able to increase the level of hydroquinone and cell sensitivity to IPI-504. NQO1 activity is not a determinant of IPI-504 activity
physiological function
-
NQO1, a 20S proteasome gatekeeper, binds and induces robust c-Fos accumulation by blocking the ubiquitin-independent degradation pathway. NQO1 protects monomeric c-Fos from proteasomal ubiquitin-independent degradation. NQO1 is important to ensure immediate c-Fos accumulation in response to serum
physiological function
NQO1 overexpression inhibits apoptosis-associated gene Bcl-2 expression and promotes apoptosis-associated gene Bax and caspase-3 expression, whereas NQO1 silencing plays a contrasting role. NQO1 activates AMP-activated protein kinase AMPK and proliferator-activated receptor gamma coactivator PGC-1a, and the AMPK inhibitor compound C blocks NQO1-induced PGC-1a activationand partially abolishes NQO1-induced cell apoptosis and proliferation inhibition in hepatocellular carcinoma cells
physiological function
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
physiological function
treatment of normal human melanocytes with carnosic acid, a transcriptional inducer of the NQO1 gene, notably suppresses the cell killing effect of tyrosinase inhibitor rhododendrol. The effect is mostly abolished by ES936, a highly specific NQO1 inhibitor. Conditional overexpression of the human NQO1 transgene in mouse B16BL6 cells leads to an expression-dependent increase of cell survival after rhododendrol treatment
UNIPROT
ENTRY NAME
ORGANISM
NO. OF AA
NO. OF TRANSM. HELICES
MOLECULAR WEIGHT[Da]
SOURCE
SEQUENCE
LOCALIZATION PREDICTION
The reliability class of the localization prediction ranges from 1 (very reliable) to 5 (not reliable).
The reliability class of the localization prediction ranges from 1 (very reliable) to 5 (not reliable). NQO1_HUMAN
274
0
30868
Swiss-Prot
Mitochondrion (Reliability: 3), Secretory Pathway (Reliability: 1)
PDB
SCOP
CATH
UNIPROT
ORGANISM
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
SUBUNIT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
dimer
homodimer
CRYSTALLIZATION (Commentary)
ORGANISM
UNIPROT
LITERATURE
1H69 crystal structure-based in silico model of NQO1 active site, NQO1 complex with bound FAD and indolequinone
crystal structure of enzyme complexed with 5-methoxy-1,2-dimethyl-3-[(4-nitrophenoxy)methyl]indole-4,7-dione, 1.8 A resolution
hanging drop vapor diffusion from a solution containing 10-15 mg/ml enzyme in 25 mM Tris-HCl, pH 8.0, 0.005 mM FAD, mixed with equal volumes of reservoir solution consisting of 30% polyethylene glycol 3350, 200 mM sodium acetate and 100 mM sodium tricine, pH 8.5, x-ray structure, 1.7 A resolution
in complex with 4-hydroxy-6,7-dimethyl-3-(1-naphthylmethyl)-2H-chromen-2-one, hanging drop vapor diffusion method, using 2.4 M ammonium sulfate and 0.1 M Tris buffer pH 8.5
PROTEIN VARIANTS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
C609T
medicine
-
use of endogenous NQO1 enzyme for nanocarrier-based drug delivery in tumors. The rotaxane nanovalve system is composed of a linear stalk anchoring on the surface of mesoporous silica nanoparticles, an alpha-cyclodextrin ring that encircles it and locks the payload cargo molecules in the mesopores, and a benzoquinone stopper incorporated at the end of the stalk. The gate opening and controlled release of the cargo are triggered by cleavage of the benzoquinone stopper using an endogenous NQO1 enzyme
P187S
naturally occurring single-nucleotide polymorphism implicated in the development of various cancers. Crystal structure is almost identcal to wild-type, the amino acid exchange destabilizes interactions between the core and C-terminus, leading to depopulation of the native structure in solution and severely compromising the catalytic capacity of the variant protein
R139W
single nucleotide polymorphism, variant protein adopts the same structure both in the crystal as in solution, and kinetic parameters are similar to those reported for the wild-type protein. Thermostability of the variant is only slightly affected
additional information
C609T
-
during cardiopulmonary bypass, interleukin-6 concentrations are increased in NQO1 T carriers compared to T non-carriers, i. e. non-laminar flow during during cardiopulmonary bypass is more deleterious in patients with NQO1 T carriers
C609T
-
no significant differences between distributions of NQO1 C609T genotypes in patients with prostate cancer and controls
C609T
natural polymorphism which 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
additional information
-
P187S protein undergoes rapid turnover via the ubiquitin proteasomal pathway, cells with the homozygous NQO1*2 genotype have no measurable NQO1 activity
additional information
-
QR1-deficient individuals exposed to occupational benzene are at a substantially higher risk of contracting leukemia than normal individuals
TEMPERATURE STABILITY
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
PURIFICATION (Commentary)
ORGANISM
UNIPROT
LITERATURE
by affinity chromatography
recombinant NAD(P)H:quinone acceptor oxidoreductase 2, affinity chromatography on Affi-gel blue
-
CLONED (Commentary)
ORGANISM
UNIPROT
LITERATURE
expressed in Escherichia coli
expression in Escherichia coli
EXPRESSION
ORGANISM
UNIPROT
LITERATURE
docosahexaenoic acid, DHA, activates transcription factor Nrf2, possibly through modification of a critical Keap1 cysteine288 residue and protein kinase delta-mediated phosphorylation of Nrf2, leading to upregulation of heme oxygenase HO-1 and NQO1 expression
APPLICATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
analysis
drug development
medicine
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
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
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
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
design of novel lavendamycin analogues with enhanced, selective, and potent antitumor activity
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
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
-
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
-
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
-
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
-
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
-
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
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
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
REF.
AUTHORS
TITLE
JOURNAL
VOL.
PAGES
YEAR
ORGANISM (UNIPROT)
PUBMED ID
SOURCE
Chen, S.; Clarke, P.E.; Martino, P.A.; Deng, P.S.K.; Yeh, C.H.; Lee, T.D.; Prochaska, H.J.; Talalay, P.
Mouse liver NAD(P)H:quinone acceptor oxidoreductase: protein sequence analysis by tandem mass spectrometry, cDNA cloning, expression in Escherichia coli, and enzyme activity analysis
Protein Sci.
3
1296-1304
1994
Homo sapiens, Mus musculus, Rattus norvegicus
Chen, S.; Knox, R.; Lewis, A.D.; Friedlos, F.; Workman, P.; Deng, P.S.K.; Fung, M.; Ebenstein, D.; Wu, K.; Tsai, T.M.
Catalytic properties of NAD(P)H:quinone acceptor oxidoreductase: study involving mouse, rat, human, and mouse-rat chimeric enzymes
Mol. Pharmacol.
47
934-939
1995
Homo sapiens, Mus musculus, Rattus norvegicus
Wu, K.; Knox, R.; Sun, X.Z.; Joseph, P.; Jaiswal, A.K.; Zhang, D.; Deng, P.S.K.; Chen, S.
Catalytic properties of NAD(P)H:quinone oxidoreductase-2 (NQO2), a dihydronicotinamide riboside dependent oxidoreductase
Arch. Biochem. Biophys.
347
221-228
1997
Homo sapiens
Phillips, R.M.
Inhibition of DT-diaphorase (NAD(P)H:quinone oxidoreductase, EC 1.6.99.2) by 5,6-dimethylxanthenone-4-acetic acid (DMXAA) and flavone-8-acetic acid (FAA): implications for bioreductive drug development
Biochem. Pharmacol.
58
303-310
1999
Homo sapiens
Faig, M.; Bianchet, M.A.; Talalay, P.; Chen, S.; Winski, S.; Ross, D.; Amzel, L.M.
Structures of recombinant human and mouse NAD(P)H:quinone oxidoreductases: species comparison and structural changes with substrate binding and release
Proc. Natl. Acad. Sci. USA
97
3177-3182
2000
Homo sapiens (P15559), Homo sapiens, Mus musculus (Q64669), Mus musculus
Pink, J.J.; Planchon, S.M.; Tagliarino, C.; Varnes, M.E.; Siegel, D.; Boothman, D.A.
NAD(P)H:quinone oxidoreductase activity is the principal determinant of beta-lapachone cytotoxicity
J. Biol. Chem.
275
5416-5424
2000
Homo sapiens
Swann, E.; Barraja, P.; Oberlander, A.M.; Gardipee, W.T.; Hudnott, A.R.; Beall, H.D.; Moody, C.J.
Indolequinone antitumor agents: correlation between quinone structure and rate of metabolism by recombinant human NAD(P)H:quinone oxidoreductase. Part 2
J. Med. Chem.
44
3311-3319
2001
Homo sapiens
Winski, S.L.; Faig, M.; Bianchet, M.A.; Siegel, D.; Swann, E.; Fung, K.; Duncan, M.W.; Moody, C.J.; Amzel, L.M.; Ross, D.
Characterization of a mechanism-based inhibitor of NAD(P)H:quinone oxidoreductase 1 by biochemical, X-ray crystallographic, and mass spectrometric approaches
Biochemistry
40
15135-15142
2001
Homo sapiens (P15559)
Vella, F.; Ferry, G.; Delagrange, P.; Boutin, J.A.
NRH:quinone reductase 2: an enzyme of surprises and mysteries
Biochem. Pharmacol.
71
1-12
2005
Homo sapiens (P15559)
Stiborova, M.; Frei, E.; Sopko, B.; Sopkova, K.; Markova, V.; Lankova, M.; Kumstyrova, T.; Wiessler, M.; Schmeiser, H.H.
Human cytosolic enzymes involved in the metabolic activation of carcinogenic aristolochic acid: evidence for reductive activation by human NAD(P)H:quinone oxidoreductase
Carcinogenesis
24
1695-1703
2003
Homo sapiens, Rattus norvegicus
Gustafson, D.L.; Siegel, D.; Rastatter, J.C.; Merz, A.L.; Parpal, J.C.; Kepa, J.K.; Ross, D.; Long, M.E.
Kinetics of NAD(P)H:quinone oxidoreductase I (NQO1) inhibition by mitomycin C in vitro and in vivo
J. Pharmacol. Exp. Ther.
305
1079-1086
2003
Homo sapiens, Mus musculus, Rattus norvegicus
SantaCruz, K.S.; Yazlovitskaya, E.; Collins, J.; Johnson, J.; DeCarli, C.
Regional NAD(P)H:quinone oxidoreductase activity in Alzheimer's disease
Neurobiol. Aging
25
63-69
2004
Homo sapiens
Asher, G.; Dym, O.; Tsvetkov, P.; Adler, J.; Shaul, Y.
The crystal structure of NAD(P)H quinone oxidoreductase 1 in complex with its potent inhibitor dicoumarol
Biochemistry
45
6372-6378
2006
Homo sapiens (P15559), Homo sapiens
Guo, W.; Reigan, P.; Siegel, D.; Zirrolli, J.; Gustafson, D.; Ross, D.
Formation of 17-allylamino-demethoxygeldanamycin (17-AAG) hydroquinone by NAD(P)H:quinone oxidoreductase 1: role of 17-AAG hydroquinone in heat shock protein 90 inhibition
Cancer Res.
65
10006-10015
2005
Homo sapiens
Lyn-Cook, B.D.; Yan-Sanders, Y.; Moore, S.; Taylor, S.; Word, B.; Hammons, G.J.
Increased levels of NAD(P)H: quinone oxidoreductase 1 (NQO1) in pancreatic tissues from smokers and pancreatic adenocarcinomas: A potential biomarker of early damage in the pancreas
Cell Biol. Toxicol.
22
73-80
2006
Homo sapiens
Han, E.H.; Hwang, Y.P.; Jeong, T.C.; Lee, S.S.; Shin, J.G.; Jeong, H.G.
Eugenol inhibit 7,12-dimethylbenz[a]anthracene-induced genotoxicity in MCF-7 cells: Bifunctional effects on CYP1 and NAD(P)H:quinone oxidoreductase
FEBS Lett.
581
749-756
2007
Homo sapiens
Lee, Y.Y.; Westphal, A.H.; de Haan, L.H.; Aarts, J.M.; Rietjens, I.M.; van Berkel, W.J.
Human NAD(P)H:quinone oxidoreductase inhibition by flavonoids in living cells
Free Radic. Biol. Med.
39
257-265
2005
Homo sapiens
van Horssen, J.; Schreibelt, G.; Bo, L.; Montagne, L.; Drukarch, B.; van Muiswinkel, F.L.; de Vries, H.E.
NAD(P)H:quinone oxidoreductase 1 expression in multiple sclerosis lesions
Free Radic. Biol. Med.
41
311-317
2006
Homo sapiens
Foppoli, C.; De Marco, F.; Blarzino, C.; Perluigi, M.; Cini, C.; Coccia, R.
Biological response of human diploid keratinocytes to quinone-producing compounds: role of NAD(P)H:quinone oxidoreductase 1
Int. J. Biochem. Cell Biol.
37
852-863
2005
Homo sapiens (P15559), Homo sapiens
AbuKhader, M.; Heap, J.; De Matteis, C.; Kellam, B.; Doughty, S.W.; Minton, N.; Paoli, M.
Binding of the anticancer prodrug CB1954 to the activating enzyme NQO2 revealed by the crystal structure of their complex
J. Med. Chem.
48
7714-7719
2005
Homo sapiens
Guo, W.; Reigan, P.; Siegel, D.; Zirrolli, J.; Gustafson, D.; Ross, D.
The bioreduction of a series of benzoquinone ansamycins by NAD(P)H:quinone oxidoreductase 1 to more potent heat shock protein 90 inhibitors, the hydroquinone ansamycins
Mol. Pharmacol.
70
1194-1203
2006
Homo sapiens
van der Logt, E.M.; Bergevoet, S.M.; Roelofs, H.M.; Te Morsche, R.H.; Dijk, Y.; Wobbes, T.; Nagengast, F.M.; Peters, W.H.
Role of epoxide hydrolase, NAD(P)H:quinone oxidoreductase, cytochrome P450 2E1 or alcohol dehydrogenase genotypes in susceptibility to colorectal cancer
Mutat. Res.
593
39-49
2006
Homo sapiens
Covarrubias, V.G.; Lakhman, S.S.; Forrest, A.; Relling, M.V.; Blanco, J.G.
Higher activity of polymorphic NAD(P)H:quinone oxidoreductase in liver cytosols from blacks compared to whites
Toxicol. Lett.
164
249-258
2006
Homo sapiens
Moffit, J.S.; Aleksunes, L.M.; Kardas, M.J.; Slitt, A.L.; Klaassen, C.D.; Manautou, J.E.
Role of NAD(P)H:quinone oxidoreductase 1 in clofibrate-mediated hepatoprotection from acetaminophen
Toxicology
230
197-206
2007
Homo sapiens, Mus musculus, Mus musculus CD-1
Aleksunes, L.M.; Goedken, M.; Manautou, J.E.
Up-regulation of NAD(P)H quinone oxidoreductase 1 during human liver injury
World J. Gastroenterol.
12
1937-1940
2006
Homo sapiens
Ergen, H.A.; Gormus, U.; Narter, F.; Zeybek, U.; Bulgurcuoglu, S.; Isbir, T.
Investigation of NAD(P)H:quinone oxidoreductase 1 (NQO1) C609T polymorphism in prostate cancer
Anticancer Res.
27
4107-4110
2008
Homo sapiens
Joung, E.J.; Li, M.H.; Lee, H.G.; Somparn, N.; Jung, Y.S.; Na, H.K.; Kim, S.H.; Cha, Y.N.; Surh, Y.J.
Capsaicin induces heme oxygenase-1 expression in HepG2 cells via activation of PI3K-Nrf2 signaling: NAD(P)H:quinone oxidoreductase as a potential target
Antioxid. Redox Signal.
9
2087-2098
2007
Homo sapiens
Blanco, J.G.; Leisenring, W.M.; Gonzalez-Covarrubias, V.M.; Kawashima, T.I.; Davies, S.M.; Relling, M.V.; Robison, L.L.; Sklar, C.A.; Stovall, M.; Bhatia, S.
Genetic polymorphisms in the carbonyl reductase 3 gene CBR3 and the NAD(P)H:quinone oxidoreductase 1 gene NQO1 in patients who developed anthracycline-related congestive heart failure after childhood cancer
Cancer
112
2789-2795
2008
Homo sapiens
Wang, Y.H.; Lee, Y.H.; Tseng, P.T.; Shen, C.H.; Chiou, H.Y.
Human NAD(P)H:quinone oxidoreductase 1 (NQO1) and sulfotransferase 1A1 (SULT1A1) polymorphisms and urothelial cancer risk in Taiwan
J. Cancer Res. Clin. Oncol.
134
203-209
2008
Homo sapiens
Colucci, M.A.; Reigan, P.; Siegel, D.; Chilloux, A.; Ross, D.; Moody, C.J.
Synthesis and evaluation of 3-aryloxymethyl-1,2-dimethylindole-4,7-diones as mechanism-based inhibitors of NAD(P)H:quinone oxidoreductase 1 (NQO1) activity
J. Med. Chem.
50
5780-5789
2007
Homo sapiens
Hassani, M.; Cai, W.; Koelsch, K.H.; Holley, D.C.; Rose, A.S.; Olang, F.; Lineswala, J.P.; Holloway, W.G.; Gerdes, J.M.; Behforouz, M.; Beall, H.D.
Lavendamycin antitumor agents: structure-based design, synthesis, and NAD(P)H:quinone oxidoreductase 1 (NQO1) model validation with molecular docking and biological studies
J. Med. Chem.
51
3104-3115
2008
Homo sapiens (P15559), Homo sapiens
Fagerholm, R.; Hofstetter, B.; Tommiska, J.; Aaltonen, K.; Vrtel, R.; Syrjaekoski, K.; Kallioniemi, A.; Kilpivaara, O.; Mannermaa, A.; Kosma, V.M.; Uusitupa, M.; Eskelinen, M.; Kataja, V.; Aittomaeki, K.; von Smitten, K.; Heikkilae, P.; Lukas, J.; Holli, K.; Bartkova, J.; Blomqvist, C.; Bartek, J.
NAD(P)H:quinone oxidoreductase 1 NQO1*2 genotype (P187S) is a strong prognostic and predictive factor in breast cancer
Nat. Genet.
40
844-853
2008
Homo sapiens
Tijhuis, M.J.; Boerboom, A.M.; Visker, M.H.; Op den Camp, L.; Nagengast, F.M.; Tan, A.C.; Rietjens, I.M.; Kok, F.J.; Aarts, J.M.; Kampman, E.
The influence of fruit and vegetable consumption and genetic variation on NAD(P)H:quinone oxidoreductase (NQO1) phenotype in an endoscopy-based population
Nutr. Cancer
60
204-215
2008
Homo sapiens, Homo sapiens (P15559)
Reigan, P.; Colucci, M.A.; Siegel, D.; Chilloux, A.; Moody, C.J.; Ross, D.
Development of indolequinone mechanism-based inhibitors of NAD(P)H:quinone oxidoreductase 1 (NQO1): NQO1 inhibition and growth inhibitory activity in human pancreatic MIA PaCa-2 cancer cells
Biochemistry
46
5941-5950
2007
Homo sapiens (P15559), Homo sapiens
Jia, Z.; Zhu, H.; Misra, H.P.; Li, Y.
Potent induction of total cellular GSH and NQO1 as well as mitochondrial GSH by 3H-1,2-dithiole-3-thione in SH-SY5Y neuroblastoma cells and primary human neurons: protection against neurocytotoxicity elicited by dopamine, 6-hydroxydopamine, 4-hydroxy-2-no
Brain Res.
1197
159-169
2008
Homo sapiens
Isbir, C.S.; Ergen, A.; Tekeli, A.; Zeybek, U.; Gormus, U.; Arsan, S.
The effect of NQO1 polymorphism on the inflammatory response in cardiopulmonary bypass
Cell Biochem. Funct.
26
534-538
2008
Homo sapiens
Song, C.W.; Chae, J.J.; Choi, E.K.; Hwang, T.S.; Kim, C.; Lim, B.U.; Park, H.J.
Anti-cancer effect of bio-reductive drug beta-lapachon is enhanced by activating NQO1 with heat shock
Int. J. Hyperthermia
24
161-169
2008
Homo sapiens, Mus musculus, Mus musculus C3H
Nolan, K.A.; Zhao, H.; Faulder, P.F.; Frenkel, A.D.; Timson, D.J.; Siegel, D.; Ross, D.; Burke, T.R.; Stratford, I.J.; Bryce, R.A.
Coumarin-based inhibitors of human NAD(P)H:quinone oxidoreductase-1. Identification, structure-activity, off-target effects and in vitro human pancreatic cancer toxicity
J. Med. Chem.
50
6316-6325
2007
Homo sapiens (P15559), Homo sapiens
Kim, Y.J.; Choi, J.Y.; Paek, D.; Chung, H.W.
Association of the NQO1, MPO, and XRCC1 polymorphisms and chromosome damage among workers at a petroleum refinery
J. Toxicol. Environ. Health A
71
333-341
2008
Homo sapiens
Begleiter, A.; Hewitt, D.; Gibson, S.B.; Johnston, J.B.
Investigation of an NQO1 polymorphism as a possible risk and prognostic factor for chronic lymphocytic leukemia
Leuk. Res.
33
74-81
2008
Homo sapiens
Choi, E.K.; Terai, K.; Ji, I.M.; Kook, Y.H.; Park, K.H.; Oh, E.T.; Griffin, R.J.; Lim, B.U.; Kim, J.S.; Lee, D.S.; Boothman, D.A.; Loren, M.; Song, C.W.; Park, H.J.
Upregulation of NAD(P)H:quinone oxidoreductase by radiation potentiates the effect of bioreductive beta-lapachone on cancer cells
Neoplasia
9
634-642
2007
Homo sapiens
Sripathy, S.P.; Chaplin, L.J.; Gaikwad, N.W.; Rogan, E.G.; Montano, M.M.
hPMC2 is required for recruiting an ERbeta coactivator complex to mediate transcriptional upregulation of NQO1 and protection against oxidative DNA damage by tamoxifen
Oncogene
27
6376-6384
2008
Homo sapiens
Newsome, J.J.; Colucci, M.A.; Hassani, M.; Beall, H.D.; Moody, C.J.
Benzimidazole- and benzothiazole-quinones: excellent substrates for NAD(P)H:quinone oxidoreductase 1
Org. Biomol. Chem.
5
3665-3673
2007
Homo sapiens
Colucci, M.A.; Moody, C.J.; Couch, G.D.
Natural and synthetic quinones and their reduction by the quinone reductase enzyme NQO1: from synthetic organic chemistry to compounds with anticancer potential
Org. Biomol. Chem.
6
637-656
2008
Mus musculus, Rattus norvegicus, Homo sapiens (P15559), Homo sapiens
Bianchet, M.A.; Erdemli, S.B.; Amzel, L.M.
Structure, function, and mechanism of cytosolic quinone reductases
Vitam. Horm.
78
63-84
2008
Homo sapiens, Mesocricetus auratus, Mus musculus, Rattus norvegicus
Cabello, C.M.; Bair, W.B.; Bause, A.S.; Wondrak, G.T.
Antimelanoma activity of the redox dye DCPIP (2,6-dichlorophenolindophenol) is antagonized by NQO1
Biochem. Pharmacol.
78
344-354
2009
Homo sapiens
Nolan, K.A.; Scott, K.A.; Barnes, J.; Doncaster, J.; Whitehead, R.C.; Stratford, I.J.
Pharmacological inhibitors of NAD(P)H quinone oxidoreductase, NQO1: structure/activity relationships and functional activity in tumour cells
Biochem. Pharmacol.
80
977-981
2010
Homo sapiens
Gonzalez-Aragon, D.; Alcain, F.J.; Ariza, J.; Jodar, L.; Barbarroja, N.; Lopez-Pedrera, C.; Villalba, J.M.
ES936 stimulates DNA synthesis in HeLa cells independently on NAD(P)H:quinone oxidoreductase 1 inhibition, through a mechanism involving p38 MAPK
Chem. Biol. Interact.
186
174-183
2010
Homo sapiens
Nolan, K.A.; Doncaster, J.R.; Dunstan, M.S.; Scott, K.A.; Frenkel, A.D.; Siegel, D.; Ross, D.; Barnes, J.; Levy, C.; Leys, D.; Whitehead, R.C.; Stratford, I.J.; Bryce, R.A.
Synthesis and biological evaluation of coumarin-based inhibitors of NAD(P)H: quinone oxidoreductase-1 (NQO1)
J. Med. Chem.
52
7142-7156
2009
Homo sapiens (P15559), Homo sapiens
Douglas, M.; Lim, A.R.; Porter, J.R.; West, K.; Pink, M.M.; Ge, J.; Wylie, A.A.; Tibbits, T.T.; Biggs, K.; Curtis, M.; Palombella, V.J.; Adams, J.; Fritz, C.C.; Normant, E.
The antiproliferative activity of the heat shock protein 90 inhibitor IPI-504 is not dependent on NAD(P)H:quinone oxidoreductase 1 activity in vivo
Mol. Cancer Ther.
8
3369-3378
2009
Homo sapiens
Adler, J.; Reuven, N.; Kahana, C.; Shaul, Y.
c-Fos proteasomal degradation is activated by a default mechanism, and its regulation by NAD(P)H:quinone oxidoreductase 1 determines c-Fos serum response kinetics
Mol. Cell. Biol.
30
3767-3778
2010
Homo sapiens
Mendoza, M.F.; Hollabaugh, N.M.; Hettiarachchi, S.U.; McCarley, R.L.
Human NAD(P)H:quinone oxidoreductase type I (hNQO1) activation of quinone propionic acid trigger groups
Biochemistry
51
8014-8026
2012
Homo sapiens
Zhang, W.; Go, M.L.
Methoxylation of resveratrol: effects on induction of NAD(P)H quinone-oxidoreductase 1 (NQO1) activity and growth inhibitory properties
Bioorg. Med. Chem. Lett.
21
1032-1035
2011
Homo sapiens, Mus musculus
Burke, P.J.; Wong, L.C.; Jenkins, T.C.; Knox, R.J.; Stanforth, S.P.
The 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 and E. coli
Bioorg. Med. Chem. Lett.
21
7447-7450
2011
Homo sapiens
Siegel, D.; Shieh, B.; Yan, C.; Kepa, J.K.; Ross, D.
Role for NAD(P)H:quinone oxidoreductase 1 and manganese-dependent superoxide dismutase in 17-(allylamino)-17-demethoxygeldanamycin-induced heat shock protein 90 inhibition in pancreatic cancer cells
J. Pharmacol. Exp. Ther.
336
874-880
2011
Homo sapiens
Rougee, L.R.; Riches, Z.; Berman, J.M.; Collier, A.C.
The ontogeny and population variability of human hepatic NADPH dehydrogenase quinone oxido-reductase 1 (NQO1)
Drug Metab. Dispos.
44
967-974
2016
Homo sapiens, Homo sapiens (P15559)
Newsome, J.J.; Hassani, M.; Swann, E.; Bibby, J.M.; Beall, H.D.; Moody, C.J.
Benzofuran-, benzothiophene-, indazole- and benzisoxazole-quinones excellent substrates for NAD(P)H quinone oxidoreductase 1
Bioorg. Med. Chem.
21
2999-3009
2013
Homo sapiens (P15559), Homo sapiens
Sasaki, J.; Sano, K.; Hagimori, M.; Yoshikawa, M.; Maeda, M.; Mukai, T.
Synthesis and in vitro evaluation of radioiodinated indolequinones targeting NAD(P)H quinone oxidoreductase 1 for internal radiation therapy
Bioorg. Med. Chem.
22
6039-6046
2014
Homo sapiens (P15559), Homo sapiens
Bian, J.; Xu, L.; Deng, B.; Qian, X.; Fan, J.; Yang, X.; Liu, F.; Xu, X.; Guo, X.; Li, X.; Sun, H.; You, Q.; Zhang, X.
Synthesis and evaluation of (+-)-dunnione and its ortho-quinone analogues as substrates for NAD(P)H quinone oxidoreductase 1 (NQO1)
Bioorg. Med. Chem. Lett.
25
1244-1248
2015
Homo sapiens (P15559)
Nagata, M.; Kimura, T.; Suzumura, T.; Kira, Y.; Nakai, T.; Umekawa, K.; Tanaka, H.; Matsuura, K.; Mitsuoka, S.; Yoshimura, N.; Oka, T.; Kudoh, S.; Hirata, K.
C609T polymorphism of NADPH quinone oxidoreductase 1 correlates clinical hematological toxicities in lung cancer patients treated with amrubicin
Clin. Med. Insights Oncol.
7
31-39
2013
Homo sapiens (P15559)
Zhang, X.; Han, K.; Yuan, D.H.; Meng, C.Y.
Overexpression of NAD(P)H quinone oxidoreductase 1 inhibits hepatocellular carcinoma cell proliferation and induced apoptosis by activating AMPK/PGC-1alpha pathway
DNA Cell Biol.
36
256-263
2017
Homo sapiens (P15559), Homo sapiens
Bian, J.; Li, X.; Xu, L.; Wang, N.; Qian, X.; You, Q.; Zhang, X.
Affinity-based small fluorescent probe for NAD(P)H quinone oxidoreductase 1 (NQO1). Design, synthesis and pharmacological evaluation
Eur. J. Med. Chem.
127
828-839
2017
Homo sapiens (P15559), Homo sapiens
Lienhart, W.D.; Gudipati, V.; Uhl, M.K.; Binter, A.; Pulido, S.A.; Saf, R.; Zangger, K.; Gruber, K.; Macheroux, P.
Collapse of the native structure caused by a single amino acid exchange in human NAD(P)H quinone oxidoreductase
FEBS J.
281
4691-4704
2014
Homo sapiens (P15559)
Lienhart, W.D.; Strandback, E.; Gudipati, V.; Koch, K.; Binter, A.; Uhl, M.K.; Rantasa, D.M.; Bourgeois, B.; Madl, T.; Zangger, K.; Gruber, K.; Macheroux, P.
Catalytic competence, structure and stability of the cancer-associated R139W variant of the human NAD(P)H quinone oxidoreductase 1 (NQO1)
FEBS J.
284
1233-1245
2017
Homo sapiens (P15559), Homo sapiens
Glorieux, C.; Sandoval, J.M.; Dejeans, N.; Ameye, G.; Poirel, H.A.; Verrax, J.; Calderon, P.B.
Overexpression of NAD(P)H quinone oxidoreductase 1 (NQO1) and genomic gain of the NQO1 locus modulates breast cancer cell sensitivity to quinones
Life Sci.
145
57-65
2016
Homo sapiens (P15559), Homo sapiens
Bang, H.; Park, S.; Saeidi, S.; Na, H.; Surh, Y.
Docosahexaenoic acid induces expression of heme oxygenase-1 and NAD(P)H Quinone oxidoreductase through activation of Nrf2 in human mammary epithelial cells
Molecules
22
E969
2017
Homo sapiens (P15559), Homo sapiens
Gayam, S.R.; Venkatesan, P.; Sung, Y.M.; Sung, S.Y.; Hu, S.H.; Hsu, H.Y.; Wu, S.P.
An NAD(P)H quinone oxidoreductase 1 (NQO1) enzyme responsive nanocarrier based on mesoporous silica nanoparticles for tumor targeted drug delivery in vitro and in vivo
Nanoscale
8
12307-12317
2016
Homo sapiens
Cui, X.; Jin, T.; Wang, X.; Jin, G.; Li, Z.; Lin, L.
NAD(P)H quinone oxidoreductase-1 overexpression predicts poor prognosis in small cell lung cancer
Oncol. Rep.
32
2589-2595
2014
Homo sapiens (P15559), Homo sapiens
Okubo, A.; Yasuhira, S.; Shibazaki, M.; Takahashi, K.; Akasaka, T.; Masuda, T.; Maesawa, C.
NAD(P)H dehydrogenase, quinone 1 (NQO1), protects melanin-producing cells from cytotoxicity of rhododendrol
Pigment cell Melanoma Res.
29
309-316
2016
Homo sapiens (P15559), Homo sapiens, Mus musculus (Q64669), Mus musculus
Kasai, S.; Arakawa, N.; Okubo, A.; Shigeeda, W.; Yasuhira, S.; Masuda, T.; Akasaka, T.; Shibazaki, M.; Maesawa, C.
NAD(P)H quinone oxidoreductase-1 expression sensitizes malignant melanoma cells to the HSP90 inhibitor 17-AAG
PLoS ONE
11
e0153181
2016
Homo sapiens (P15559), Homo sapiens
Zhang, Y.; den Braver-Sewradj, S.P.; Vos, J.C.; Vermeulen, N.P.E.; Commandeur, J.N.M.
Human glutathione S-transferases- and NAD(P)H quinone oxidoreductase 1-catalyzed inactivation of reactive quinoneimines of amodiaquine and N-desethylamodiaquine Possible implications for susceptibility to amodiaquine-induced liver toxicity
Toxicol. Lett.
275
83-91
2017
Homo sapiens (P15559), Homo sapiens
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