HOME
login
history
all enzymes
BRENDA home
History
Enzyme Nomenclature
Information on EC 1.6.5.2 - NAD(P)H dehydrogenase (quinone)
Word Map on EC 1.6.5.2
- 1.6.5.2
- superoxide
- hepatic
-
carcinogen
- catalase
-
chemopreventive
-
detoxify
- gsh
- dicoumarol
-
two-electron
- carcinogenesis
-
xenobiotic
- hydroquinone
-
oxygenase-1
- mitomycin
-
cytoprotective
-
bioreductive
- isothiocyanate
- cyp1a1
- sulforaphane
-
one-electron
-
benzoapyrene
-
nadph-cytochrome
- nitroreductase
- hepa
- semiquinone
-
2-related
-
chemoprotective
- 3-methylcholanthrene
-
drug-metabolizing
-
anticarcinogenic
-
decolor
-
detox
- nadph-d
-
nf-e2-related
-
cruciferous
- glucosinolates
-
udp-glucuronosyltransferase
- broccoli
-
xenobiotic-metabolizing
- plastoquinone
-
glutamate-cysteine
-
nrf2-mediated
-
ferredoxin-nadp+
- hydroxyanisole
-
ethoxyresorufin
- medicine
-
nrf2-dependent
-
kelch-like
- myrosinase
- o-quinone
- methemoglobinemia
- degradation
- pharmacology
- analysis
- drug development
- biotechnology
Please wait a moment until all data is loaded. This message will disappear when all data is loaded.
Specify your search results
The expected taxonomic range for this enzyme is: Eukaryota, Archaea, Bacteria
topPlease wait a moment until the data is sorted. This message will disappear when the data is sorted.
EC NUMBER 
COMMENTARY 
1.6.5.2
-
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
RECOMMENDED NAME
GeneOntology No.
NAD(P)H dehydrogenase (quinone)
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
NAD(P)H + H+ + a quinone = NAD(P)+ + a hydroquinone
-
-
-
-
NAD(P)H + H+ + a quinone = NAD(P)+ + a hydroquinone
ping-pong mechanism
-
NAD(P)H + H+ + a quinone = NAD(P)+ + a hydroquinone
ordered bi-bi mechanism
-
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
-
NAD(P)H + H+ + a quinone = NAD(P)+ + a hydroquinone
ping-pong reaction mechanism
-
NAD(P)H + H+ + a quinone = NAD(P)+ + a hydroquinone
ping-pong mechanism with substrate inhibition
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
oxidation
redox reaction
-
-
-
-
reduction
oxidation
-
-
-
-
reduction
-
-
-
-
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
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.
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
CAS REGISTRY NUMBER
COMMENTARY
9032-20-6
-
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
-
394372, 394375, 394379, 394384, 658402, 659782, 660005, 672967, 673704, 677204, 684502, 691553, 691669, 692674, 693895, 693945, 694350, 694497, 694511, 695265, 696140, 711167, 711730, 713005, 713018, 724356, 724516, 724531, 725775
-
-
-
SwissProt
; patients with congestive heart failure after anthracycline treatment during childhood
-
-
patients with liver damage due to acetaminophen overdose or primary biliary cirrhosis
-
-
-
394365, 394375, 655164, 659782, 673294, 689700, 691592, 692171, 692722, 694519, 695265, 701308, 724516
-
-
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
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
-
isoform NQO1-KO mice exhibit a marked increase of permeability and spontaneous inflammation in the gut. In the dextran sulfate sodium salt-induced colitis model, NQO1-KO mice show more severe inflammatory responses than NQO1-wild-type mice. The transcript levels of claudin and occludin, the major tight junction molecules of gut epithelial cells, are significantly decreased in NQO1-KO mice. The colons of NQO1-KO mice also show high levels of reactive oxygen species and histone deacetylase activity
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
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
1,4-dimethoxymethylbenzoquinone + NAD(P)H
1,4-dimethoxymethylhydrobenzoquinone + NAD(P)+
-
-
-
?
1,4-tetramethylbenzoquinone + NAD(P)H
1,4-tetramethylhydrobenzoquinone + NAD(P)+
-
-
-
?
1,8-dihydroxy-9,10-anthraquinone + NADPH
1,8-dihydroxy-9,10-anthraquinol + NADP+
-
-
-
-
?
1-hydroxy-2-[2-(nitrooxy)ethyl]-1-oxo-2-(2,4,6-trinitro-3-(nitro[2-(nitrooxy)ethyl]amino)phenyl)diazanium + NAD(P)H + H+
reduced 1-hydroxy-2-[2-(nitrooxy)ethyl]-1-oxo-2-(2,4,6-trinitro-3-(nitro[2-(nitrooxy)ethyl]amino)phenyl)diazanium + NAD(P)+
-
-
ratio kcat to Km value is 52000 per M and s
-
?
1-hydroxy-9,10-anthraquinone + NADPH
1-hydroxy-9,10-anthraquinol + NADP+
-
-
-
-
?
17-(2-dimethylylamino)ethylamino-17-demethoxygeldanamycin + NAD(P)H + H+
reduced 17-(2-dimethylylamino)ethylamino-17-demethoxygeldanamycin + NADP+
-
-
reduced component is a more potent Hsp90 inhibitor than parent benzoquinone ansamycin
-
?
17-(2-pyrrolidin-1-yl)ethylamino-17-demethoxygeldanamycin + NAD(P)H + H+
reduced 17-(2-pyrrolidin-1-yl)ethylamino-17-demethoxygeldanamycin + NADP+
-
-
reduced component is a more potent Hsp90 inhibitor than parent benzoquinone ansamycin
-
?
17-allylamino-17-demethoxygeldanamycin + NAD(P)H + H+
reduced 17-allylamino-17-demethoxygeldanamycin + NADP+
-
-
reduced component is a more potent Hsp90 inhibitor than parent benzoquinone ansamycin
-
?
17-amino-17-demethoxygeldanamycin + NAD(P)H + H+
reduced 17-amino-17-demethoxygeldanamycin + NADP+
-
-
reduced component is a more potent Hsp90 inhibitor than parent benzoquinone ansamycin
-
?
2 ferricyanide + NADH
2 ferrocyanide + NAD+ + H+
-
60% activity compared to the reactions of NADPH or NADH with 2,3-dimethoxy-5-methyl-1,4-benzoquinone
-
-
?
2,3,5,6-tetramethyl-1,4-benzoquinone + NAD(P)H
reduced 2,3,5,6-tetramethyl-1,4-benzoquinone + NAD(P)+
-
-
-
-
?
2,3-diglutathionyl-1,4-naphthoquinone + NADPH
2,3-diglutathionyl-1,4-naphthoquinol + NADP+
-
-
-
-
?
2,3-dihydroxy-5-methyl-1,4-benzoquinone + NAD(P)H
2,3-dihydroxy-5-methyl-1,4-benzoquinol + NAD(P)+
2,3-dimethyl-1,4-naphthoquinone + NAD(P)H
2,3-dimethyl-1,4-hydronaphthoquinone + NAD(P)+
-
-
-
?
2,4,6-trinitrotoluene + NAD(P)H +
reduced 2,4,6-trinitrotoluene + NAD(P)+
-
-
ratio kcat to Km value is 670 per M and s
-
?
2,5-bis(aziridin-1-yl)-3,6-dimethylcyclohexa-2,5-diene-1,4-dione + NAD(P)H
2,5-bis(aziridin-1-yl)-3,6-dimethylbenzene-1,4-diol + NAD(P)+
-
excellent substrate
-
-
?
2,5-bis(aziridin-1-yl)-3-(hydroxymethyl)-6-methylcyclohexane-1,4-dione + NAD(P)H
2,5-bis(aziridin-1-yl)-3-(hydroxymethyl)-6-methylbenzene-1,4-diol + NAD(P)+
-
excellent substrate
-
-
?
2,5-bis(ethylamine)-3,6-diaziridinyl-1,4-benzoquinone + NADPH
2,5-bis(ethylamine)-3,6-diaziridinyl-1,4-benzoquinol + NADP+
-
-
-
-
?
2,5-diaziridinyl-1,4-benzoquinone + NADPH
2,5-diaziridinyl-1,4-benzoquinol + NADP+
-
-
-
-
?
2,5-diaziridinyl-3-(hydroxymethyl)-6-methyl-1,4-benzoquinone + NADPH
2,5-diaziridinyl-3-(hydroxymethyl)-6-methyl-1,4-benzoquinol + NADP+
-
-
-
-
?
2,5-dihydroxy-1,4-naphthoquinone + NADPH
2,5-dihydroxy-1,4-naphthoquinol + NADP+
-
-
-
-
?
2,5-dimethoxy-1,3-benzothiazole-4,7-dione + NAD(P)H
2,5-dimethoxy-1,3-benzothiazole-4,7-diol + NAD(P)+
-
-
-
-
?
2,5-dimethoxy-1-methyl-1H-benzimidazole-4,7-dione + NAD(P)H
2,5-dimethoxy-1-methyl-1H-benzimidazole-4,7-diol + NAD(P)+
-
-
-
-
?
2,5-dimethyl-1,4-benzoquinone + NADPH
2,5-dimethyl-1,4-benzoquinol + NADP+
-
-
-
-
?
2,5-dimethyl-1,4-naphthoquinone + NADPH
2,5-dimethyl-1,4-naphthoquinol + NADP+
-
-
-
-
?
2,5-dimethyl-3,6-diaziridinyl-1,4-benzoquinone + NADPH
2,5-dimethyl-3,6-diaziridinyl-1,4-benzoquinol + NADP+
-
-
-
-
?
2,6-dimethoxybenzoquinone + NAD(P)H
2,6-dimethoxyhydrobenzoquinone + NAD(P)+
-
-
-
?
2,6-dimethyl-1,4-benzoquinone + NADPH
2,6-dimethyl-1,4-benzoquinol + NADP+
-
-
-
-
?
2-acetoxymethyl-6-methoxy-1-methylbenzimidazole-4,7-dione + NADH
? + NAD+
-
-
-
-
?
2-chloro-6-hydroxy-1,4-benzoquinone + NADH
6-chlorobenzene-1,2,4-triol + NAD+
-
-
-
-
?
2-ethyl-1,4-naphthoquinone + NAD(P)H
2-ethyl-1,4-hydronaphthoquinone + NAD(P)+
-
-
-
?
2-hydroxy-1,4-naphthoquinone + NADPH
2-hydroxy-1,4-naphthoquinol + NADP+
-
-
-
-
?
2-hydroxymethyl-5-methoxy-1-methylbenzimidazole-4,7-dione + NADH
? + NAD+
-
-
-
-
?
2-hydroxymethyl-5-methoxy-2,5-cyclohexadiene-1,4-dione + NAD(P)H
2-hydroxymethyl-5-methoxy-2,5-cyclohexadiene-1,4-diol + NAD(P)+
-
-
-
?
2-hydroxymethyl-6-methoxy-1-methylbenzimidazole-4,7-dione + NADH
? + NAD+
-
-
-
-
?
2-methoxy-2,5-cyclohexadiene-1,4-dione + NAD(P)H
2-methoxy-2,5-cyclohexadiene-1,4-diol + NAD(P)+
-
-
-
?
2-methoxy-5-(methoxymethyl)-2,5-cyclohexadiene-1,4-dione + NAD(P)H
2-methoxy-5-methoxymethyl-2,5-cyclohexadiene-1,4-diol + NAD(P)+
-
-
-
?
2-methoxyquinone + NAD(P)H
2-methoxyhydroquinone + NAD(P)+
Sporotrichum pulverulentum
-
-
-
?
2-methyl-1,4-benzoquinone + NADPH
2-methyl-1,4-benzoquinol + NADP+
-
-
-
-
?
2-methyl-1,4-naphthoquinone + NAD(P)H
2-methyl-1,4-dihydronaphthoquinone + NAD(P)+
-
-
-
?
2-methyl-3-glutathionyl-5-hydroxy-1,4-naphthoquinone + NADPH
2-methyl-3-glutathionyl-5-hydroxy-1,4-naphthoquinol + NADP+
-
-
-
-
?
2-methyl-3-hydroxy-1,4-naphthoquinone + NADPH
2-methyl-3-hydroxy-1,4-naphthoquinol + NADP+
-
-
-
-
?
2-methyl-3-phythyl-1,4-naphthoquinone + NAD(P)H
2-methyl-3-phythyl-1,4-naphthohydroquinone + NAD(P)+
2-methyl-5-aziridinyl-1,4-benzoquinone + NADPH
2-methyl-5-aziridinyl-1,4-benzoquinol + NADP+
-
-
-
-
?
2-methyl-5-hydroxy-1,4-naphthoquinone + NADPH
2-methyl-5-hydroxy-1,4-naphthoquinol + NADP+
-
-
-
-
?
2-[nitro(2,4,6-trinitrophenyl)amino]ethyl nitrate + NAD(P)H +
reduced 2-[nitro(2,4,6-trinitrophenyl)amino]ethyl nitrate + NAD(P)+
-
-
ratio kcat to Km value is 570000 per M and s
-
?
3,4-dihydro-2,2-dimethyl-2H-naphthol[1,2-b]pyran-5,6-dione + NAD(P)H
3,4-dihydro-2,2-dimethyl-2H-naphthol[1,2-b]pyran-5,6-diol + NAD(P)+
-
trivial name beta-lapachone, potent cytotoxic agent against various cancer cell lines
-
?
3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide + NAD(P)H
reduced 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide + NAD(P)+
3-(hydroxymethyl)-5-methoxy-1-methyl-2-phenyl-1H-indole-4,7-dione + NAD(P)H
3-(hydroxymethyl)-5-methoxy-1-methyl-2-phenyl-1H-indole-4,7-diol + NAD(P)+
-
excellent substrate
-
-
?
4,5,6,7-tetranitro-1,3-dihydro-2H-benzimidazol-2-one + NAD(P)H +
reduced 4,5,6,7-tetranitro-1,3-dihydro-2H-benzimidazol-2-one + NAD(P)+
-
-
ratio kcat to Km value is 5000000 per M and s
-
?
4,5,6-trinitro-1,3-dihydro-2H-benzimidazol-2-one + NAD(P)H +
reduced 4,5,6-trinitro-1,3-dihydro-2H-benzimidazol-2-one + NAD(P)+
-
-
ratio kcat to Km value is 26000 per M and s
-
?
4,5-dimethoxy-3,5-cyclohexadiene-1,2-dione
4,5-dimethoxy-3,5-cyclohexadiene-1,2-diol + NAD(P)+
-
-
-
?
5,8-dihydroxy-1,4-naphthoquinone + NADPH
5,8-dihydroxy-1,4-naphthoquinol + NADP+
-
-
-
-
?
5,8-dihydroxynaphthoquinone + NAD(P)H
5,8-dihydroxynaphthohydroquinone + NAD(P)+
-
-
-
?
5-(1-aziridinyl)-3-(hydroxymethyl)-2-(3-hydroxy-1-propenyl)-1-methyl-1H-indole-4,7-dione + NAD(P)H
5-(1-aziridinyl)-3-(hydroxymethyl)-2-(3-hydroxy-1-propenyl)-1-methyl-1H-indole-4,7-diol + NAD(P)+
5-(aziridin-1-yl)-2,4-dinitrobenzamide + NAD(P)H
5-(aziridin-1-yl)-4-hydroxylamino-2-nitrobenzamide + NAD(P)+
5-(aziridin-1-yl)-2,4-dinitrobenzamide + reduced dihydronicotineamide riboside
5-(aziridin-1-yl)-4-hydroxylamino-2-nitrobenzamide + oxidized dihydronicotineamide riboside
5-aziridin-1-yl-2,4-dinitrobenzamide + NAD(P)H + H+
5-aziridin-1-yl-4-(hydroxyamino)-2-nitrobenzamide
-
i.e. CB1954, anticancer prodrug
-
-
?
5-aziridin-1-yl-3-(hydroxymethyl)-2-[(1E)-3-hydroxyprop-1-en-1-yl]-1-methyl-1H-indole-4,7-dione + NAD(P)H
5-aziridin-1-yl-3-(hydroxymethyl)-2-[(1E)-3-hydroxyprop-1-en-1-yl]-1-methyl-1H-indole-4,7-diol + NAD(P)+
-
-
-
-
?
5-hydroxy-1,4-naphthoquinone + NADPH
5-hydroxy-1,4-naphthoquinol + NADP+
-
-
-
-
?
5-methoxy-1,2-dimethyl-3-(hydroxymethyl)indole-4,7-dione + NADH
? + NAD+
-
is efficiently metabolized by NQO1
-
-
?
5-methoxy-1,2-dimethyl-3-[(phenoxy)methyl]indole-4,7-dione + NADH
? + NAD+
-
inefficient indolequinone substrate
-
-
?
6-hydroxydopaminequinone + NAD(P)H
6-hydroxydopaminehydroquinone + NAD(P)+
-
-
-
?
6-hydroxydopaquinone + NAD(P)H
6-hydroxydopahydroquinone + NAD(P)+
-
-
-
?
6-methoxy-1,2-dimethyl-3-(hydroxymethyl)indole-4,7-dione + NADH
? + NAD+
-
is efficiently metabolized by NQO1
-
-
?
6-methoxy-1,2-dimethyl-3-[(phenoxy)methyl]indole-4,7-dione + NADH
? + NAD+
-
inefficient indolequinone substrate
-
-
?
6-methoxy-1-methyl-2-(4-nitrophenoxymethyl)benzimidazole-4,7-dione + NADH
? + NAD+
-
-
-
-
?
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
-
-
?
9,10-phenanthrene quinone + NADPH
9,10-phenanthrene quinol + NADP+
-
-
-
-
?
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
benzo[a]pyrene 3,6-quinone + NAD(P)H
benzo[a]pyrene 3,6-quinol
-
-
-
?
cyclized-dopamine o-quinone + NAD(P)H
cyclized-dopamine o-hydroquinone + NADP+
-
-
-
?
deamino-NADH + H+ + 2,3-dimethoxy-5-methyl-1,4-benzoquinone
deamino-NAD+ + 2,3-dimethoxy-5-methyl-1,4-benzoquinol
-
45% activity compared to NADPH or NADH
-
-
?
diethyl [2,5-bis(aziridin-1-yl)-3,6-dioxocyclohexa-1,4-diene-1,4-diyl]biscarbamate + NAD(P)H
diethyl [2,5-bis(aziridin-1-yl)-3,6-dihydroxybenzene-1,4-diyl]biscarbamate + NAD(P)+
-
-
-
-
?
duroquinone + NADPH
durohydroquinone + NADP+
-
in both normoxic and hyperoxia-exposed cells, enzyme is the dominant duroquinone reductase
-
-
?
ethyl 5-aziridin-1-yl-2,4-dinitrobenzoate + NAD(P)H +
reduced ethyl 5-aziridin-1-yl-2,4-dinitrobenzoate + NAD(P)+
-
-
ratio kcat to Km value is 20000 per M and s
-
?
geldanamycin + NAD(P)H
reduced geldanamycin + NAD(P)+
-
excellent substrate
-
-
?
geldanamycin + NAD(P)H + H+
reduced geldanamycin + NADP+
-
-
reduced component is a more potent Hsp90 inhibitor than parent benzoquinone ansamycin
-
?
hydroxy(oxo)(3,6,8-trinitro-9H-carbazol-1-yl)ammonium + NAD(P)H +
reduced 2-[nitro(2,4,6-trinitrophenyl)amino]ethyl nitrate + NAD(P)+
-
-
ratio kcat to Km value is 500000 per M and s
-
?
indolequinones + NAD(P)H
indolehydroquinones + NAD(P)+
-
compounds with electron-withdrawing groups at the indole 3-position are among the best substrates, groups larger than methyl at N-1 are tolerated, compounds with a leaving group at the 3-indolyl methyl position inactivate the enzyme
-
?
lavendamycin beta-hydroxyethyl ester + NADH
? + NAD+
good substrate
-
-
?
menadione + reduced nicotinamide 2-azidoadenine dinucleotide
reduced menadione + oxidized nicotinamide 2-azidoadenine dinucleotide
-
-
-
?
menadione + reduced nicotinamide 8-azidoadenine dinucleotide
reduced menadione + oxidized nicotinamide 8-azidoadenine dinucleotide
-
-
-
?
methoxyquinone + NAD(P)H
methoxyhydroquinone + NAD(P)+
Sporotrichum pulverulentum
-
-
-
?
methyl-1,4-benzoquinone + NADPH + H+
methyl-1,4-benzoquinol + NADP+
two-electron mechanism
-
-
?
N-methyl-N,2,4,6-tetranitroaniline + NAD(P)H +
reduced N-methyl-N,2,4,6-tetranitroaniline + NAD(P)+
-
-
ratio kcat to Km value is 260000 per M and s
-
?
N-methyl-N,2,4-trinitroaniline + NAD(P)H +
reduced N-methyl-N,2,4-trinitroaniline + NAD(P)+
-
-
ratio kcat to Km value is 52000 per M and s
-
?
NAD(P)H + H+ + 17-allylamino-demethoxygeldanamycin
NAD(P)+ + reduced 17-allylamino-demethoxygeldanamycin
-
-
product exhibits superior Hsp90 inhibition and is involved in Hsp70 induction and Raf-1 degradation
-
?
NAD(P)H + H+ + 2,5-diaziridinyl-3-hydroxymethyl-6-methyl-1,4-benzoquinone
NAD(P)+ + reduced 2,5-diaziridinyl-3-hydroxymethyl-6-methyl-1,4-benzoquinone
-
i.e. RH1, induction of apoptosis via enzyme-linked formation of alkylating species
-
-
?
NAD(P)H + H+ + 2,5-dimethyl-3,6-diaziridinyl-1,4-benzoquinone
NAD(P)+ + reduced 2,5-dimethyl-3,6-diaziridinyl-1,4-benzoquinone
-
i.e. MeDZQ, induction of apoptosis via enzyme-linked formation of alkylating species
-
-
?
NAD(P)H + H+ + a quinone
NAD(P)+ + a hydroquinone
the enzyme catalyzes a detoxification process. QR1 gene expression is induced in response to xenobiotics, oxidants, heavy metals, UV light, and ionisation radiation. The enzyme is part of an electrophilic-induced and/or oxidative stress-induced cellular defense mechanism that includes the induction of more than two dozen defensive genes
-
-
?
NAD(P)H + H+ + 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+ + 2,3-dimethoxy-5-methyl-1,4-benzoquinone
NAD+ + 2,3-dimethoxy-5-methyl-1,4-benzoquinol
-
-
-
-
?
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-methyl-1,4-naphthoquinone
NAD+ + 2-methyl-1,4-naphthoquinol
-
-
-
-
?
NADH + H+ + 2-[2,4-dinitro-6-(trifluoromethyl)phenyl]-1,2,3,4-tetrahydronaphthalene
?
-
-
-
-
?
NADH + H+ + 2-[2,4-dinitro-6-(trifluoromethyl)phenyl]-5-nitro-1,2,3,4-tetrahydronaphthalene
?
-
-
-
-
?
NADH + H+ + 2-[2,4-dinitro-6-(trifluoromethyl)phenyl]-7-nitro-1,2,3,4-tetrahydronaphthalene
?
-
-
-
-
?
NADH + H+ + 3,5-dinitro-2-(1,2,3,4-tetrahydronaphthalen-2-yl)benzamide
?
-
-
-
-
?
NADH + H+ + 3,5-dinitro-2-(1,2,3,4-tetrahydronaphthalen-2-yl)benzoic acid
?
-
-
-
-
?
NADH + H+ + 3,5-dinitro-2-(7-nitro-1,2,3,4-tetrahydronaphthalen-2-yl)benzoic acid
?
-
-
-
-
?
NADH + H+ + 4,10-dinitro-5,6-dihydrobenzimidazo[2,1-a]isoquinoline 12-oxide
?
-
-
-
-
?
NADH + H+ + 4,10-dinitro-5,6-dihydrobenzimidazo[2,1-a]isoquinoline-9-carboxamide 12-oxide
?
-
-
-
-
?
NADH + H+ + 4,10-dinitro-8-(trifluoromethyl)-5,6-dihydrobenzimidazo[2,1-a]isoquinoline 12-oxide
?
-
-
-
-
?
NADH + H+ + 5,6-dihydro-10-nitropyrido[3'',2'':4',5']imidazo[2',1'-a]isoquinoline 12-oxide
?
-
-
-
-
?
NADH + H+ + atovaquone
NAD+ + reduced atovaquone
-
atovaquone is 2-[4-(4-chlorophenyl)cyclohexyl]-3-hydroxynaphthalene-1,4-dione
-
-
?
NADH + H+ + dichlorophenolindophenol
NAD+ + reduced dichlorophenolindophenol
-
-
-
-
?
NADH + H+ + ubiquinone
NAD+ + ubiquinone
-
the enzyme plays an essential role in maintaining a reduced ubiquinone-pool during infection (Plasmodium falciparum is the causative agents of malaria). The enzyme is not only essential to parasite survival in vivo but may also contribute to the severity and outcome of disease. Type II NADH:quinone oxidoreductase the membrane-bound respiratory enzyme differs from the canonical NADH:dehydrogenase (complex I), because it is not involved in the vectorial transfer of protons across membranes. In the electron transport chain of Plasmodium, the canonical multimeric complex I (NADH:dehydrogenase) found in mammalian mitochondria is absent, and, instead, the parasite possesses five quinone-dependent oxidoreductases, namely a type II NADH:quinone oxidoreductase (PfNDH2), a malate: quinone oxidoreductase (MQO), a dihydroorotate dehydrogenase (DHOD), a glycerol-3-phosphate dehydrogenase (G3PDH), and a succinate: quinone oxidoreductase (SDH). These enzymes link cytosolic metabolism to mitochondrial metabolism, generating reducing power (ubiquinol) for the bc1 complex and an aa3-type cytochrome oxidase, enabling proton pumping and energy conservation
-
-
?
NADPH + H+ + 2,3-dimethoxy-5-methyl-1,4-benzoquinone
NADP+ + 2,3-dimethoxy-5-methyl-1,4-benzoquinol
-
100% activity
-
-
?
NADPH + H+ + 2-methyl-1,4-naphthoquinone
NADP+ + 2-methyl-1,4-naphthoquinol
-
-
-
-
?
NADPH + H+ + oxidized 2,6-dichlorophenolindophenol
NADP+ + reduced 2,6-dichlorophenolindophenol
nitracrine + NAD(P)H +
reduced nitracrine + NAD(P)+
-
-
i.e. N,N-dimethyl-N'-(1-nitro-9,10-dihydroacridin-9-yl)propane-1,3-diamine, ratio kcat to Km value is 1800 per M and s
-
?
streptonigrin + NAD(P)H
reduced streptonigrin + NAD(P)+
-
one of the best substrates for NQO1
-
-
?
tetramethyl-1,4-benzoquinone + NADPH
tetramethyl-1,4-benzoquinol + NADP+
-
-
-
-
?
ubiquinone-1 + NADPH + H+
ubiquinol-1 + NADP+
-
the protein shows NADH-ubiquinone-1 oxidoreductase activity (EC 1.6.5.3), NADPH oxidase (EC 1.6.3.1) and NADPH-ubiquinone-1 oxidoreductase (EC 1.6.5.2) activities
-
-
?
1,4-naphthoquinone + NAD(P)H
1,4-naphthohydroquinone + NAD(P)+
-
-
-
?
1,4-naphthoquinone + NAD(P)H
1,4-naphthohydroquinone + NAD(P)+
-
-
-
?
1,4-naphthoquinone + NAD(P)H
1,4-naphthohydroquinone + NAD(P)+
-
-
-
?
1,4-naphthoquinone + NAD(P)H
1,4-naphthohydroquinone + NAD(P)+
-
-
-
?
1,4-naphthoquinone + NAD(P)H
1,4-naphthohydroquinone + NADP+
-
-
-
-
?
1,4-naphthoquinone + NAD(P)H
1,4-naphthohydroquinone + NADP+
-
-
-
-
?
2 ferricyanide + NAD(P)H
2 ferrocyanide + NAD(P)+ + H+
-
-
-
-
?
2,3-dihydroxy-5-methyl-1,4-benzoquinone + NAD(P)H
2,3-dihydroxy-5-methyl-1,4-benzoquinol + NAD(P)+
-
-
-
?
2,3-dihydroxy-5-methyl-1,4-benzoquinone + NAD(P)H
2,3-dihydroxy-5-methyl-1,4-benzoquinol + NAD(P)+
-
-
-
?
2-methyl-1,4-naphthoquinone + NAD(P)H
2-methyl-1,4-naphthoquinol + NAD(P)+
-
artificial acceptor, trivial name menadione
-
?
2-methyl-1,4-naphthoquinone + NAD(P)H
2-methyl-1,4-naphthoquinol + NAD(P)+
-
artificial acceptor, trivial name menadione
-
?
2-methyl-1,4-naphthoquinone + NAD(P)H
2-methyl-1,4-naphthoquinol + NAD(P)+
-
artificial acceptor, trivial name menadione
-
?
2-methyl-1,4-naphthoquinone + NAD(P)H
2-methyl-1,4-naphthoquinol + NAD(P)+
-
artificial acceptor, trivial name menadione
-
?
2-methyl-1,4-naphthoquinone + NAD(P)H
2-methyl-1,4-naphthoquinol + NAD(P)+
-
-
-
?
2-methyl-1,4-naphthoquinone + NAD(P)H
2-methyl-1,4-naphthoquinol + NAD(P)+
-
involved in the process of reductive activation of several cytotoxic antitumor quinones, such as mitomycins, anthracyclines and azaridinylbenzoquinones
-
?
2-methyl-1,4-naphthoquinone + NAD(P)H
2-methyl-1,4-naphthoquinol + NAD(P)+
-
-
-
-
-
2-methyl-1,4-naphthoquinone + NAD(P)H
2-methyl-1,4-naphthoquinol + NAD(P)+
-
-
-
?
2-methyl-1,4-naphthoquinone + NAD(P)H
2-methyl-1,4-naphthoquinol + NAD(P)+
-
artificial acceptor, trivial name menadione
-
?
2-methyl-1,4-naphthoquinone + NAD(P)H
2-methyl-1,4-naphthoquinol + NAD(P)+
-
-
-
?
2-methyl-1,4-naphthoquinone + NAD(P)H
2-methyl-1,4-naphthoquinol + NAD(P)+
-
microsomal enzyme
-
-
2-methyl-1,4-naphthoquinone + NAD(P)H
2-methyl-1,4-naphthoquinol + NAD(P)+
-
artificial acceptor, trivial name menadione
-
?
2-methyl-1,4-naphthoquinone + NAD(P)H
2-methyl-1,4-naphthoquinol + NAD(P)+
-
artificial acceptor, trivial name menadione
-
?
2-methyl-1,4-naphthoquinone + NAD(P)H
2-methyl-1,4-naphthoquinol + NAD(P)+
-
artificial acceptor, trivial name menadione
-
?
2-methyl-1,4-naphthoquinone + NAD(P)H
2-methyl-1,4-naphthoquinol + NAD(P)+
-
artificial acceptor, trivial name menadione
-
?
2-methyl-1,4-naphthoquinone + NAD(P)H
2-methyl-1,4-naphthoquinol + NAD(P)+
-
-
-
?
2-methyl-1,4-naphthoquinone + NADH
2-methyl-1,4-naphthoquinol + NAD+
-
-
-
-
?
2-methyl-1,4-naphthoquinone + NADH
2-methyl-1,4-naphthoquinol + NAD+
-
-
-
-
?
2-methyl-1,4-naphthoquinone + NADH
2-methyl-1,4-naphthoquinol + NAD+
-
-
-
-
?
2-methyl-1,4-naphthoquinone + NADPH
2-methyl-1,4-naphthoquinol + NADp+
-
-
-
-
?
2-methyl-1,4-naphthoquinone + NADPH
2-methyl-1,4-naphthoquinol + NADp+
-
-
-
-
?
2-methyl-1,4-naphthoquinone + NADPH
2-methyl-1,4-naphthoquinol + NADp+
-
-
-
-
?
2-methyl-1,4-naphthoquinone + NADPH
2-methyl-1,4-naphthoquinol + NADp+
-
-
-
-
?
2-methyl-3-phythyl-1,4-naphthoquinone + NAD(P)H
2-methyl-3-phythyl-1,4-naphthohydroquinone + NAD(P)+
-
-
-
-
-
2-methyl-3-phythyl-1,4-naphthoquinone + NAD(P)H
2-methyl-3-phythyl-1,4-naphthohydroquinone + NAD(P)+
-
trivial name vitamin K1
-
?
2-methyl-3-phythyl-1,4-naphthoquinone + NAD(P)H
2-methyl-3-phythyl-1,4-naphthohydroquinone + NAD(P)+
-
no activity with vitamin K1 diphosphate, menadione diphosphate, vitamin K1 oxide, d-alpha-tocopherol and d-alpha-tocoquinone
-
?
2-methyl-3-phythyl-1,4-naphthoquinone + NAD(P)H
2-methyl-3-phythyl-1,4-naphthohydroquinone + NAD(P)+
-
trivial name vitamin K1
-
?
2-methyl-3-phythyl-1,4-naphthoquinone + NAD(P)H
2-methyl-3-phythyl-1,4-naphthohydroquinone + NAD(P)+
-
trivial name vitamin K1
-
?
3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide + NAD(P)H
reduced 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide + NAD(P)+
-
-
-
?
3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide + NAD(P)H
reduced 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide + NAD(P)+
-
-
-
-
?
5-(1-aziridinyl)-3-(hydroxymethyl)-2-(3-hydroxy-1-propenyl)-1-methyl-1H-indole-4,7-dione + NAD(P)H
5-(1-aziridinyl)-3-(hydroxymethyl)-2-(3-hydroxy-1-propenyl)-1-methyl-1H-indole-4,7-diol + NAD(P)+
-
-
-
?
5-(1-aziridinyl)-3-(hydroxymethyl)-2-(3-hydroxy-1-propenyl)-1-methyl-1H-indole-4,7-dione + NAD(P)H
5-(1-aziridinyl)-3-(hydroxymethyl)-2-(3-hydroxy-1-propenyl)-1-methyl-1H-indole-4,7-diol + NAD(P)+
-
-
-
?
5-(1-aziridinyl)-3-(hydroxymethyl)-2-(3-hydroxy-1-propenyl)-1-methyl-1H-indole-4,7-dione + NAD(P)H
5-(1-aziridinyl)-3-(hydroxymethyl)-2-(3-hydroxy-1-propenyl)-1-methyl-1H-indole-4,7-diol + NAD(P)+
-
-
-
?
5-(aziridin-1-yl)-2,4-dinitrobenzamide + NAD(P)H
5-(aziridin-1-yl)-4-hydroxylamino-2-nitrobenzamide + NAD(P)+
-
-
-
?
5-(aziridin-1-yl)-2,4-dinitrobenzamide + NAD(P)H
5-(aziridin-1-yl)-4-hydroxylamino-2-nitrobenzamide + NAD(P)+
-
-
-
?
5-(aziridin-1-yl)-2,4-dinitrobenzamide + NAD(P)H
5-(aziridin-1-yl)-4-hydroxylamino-2-nitrobenzamide + NAD(P)+
-
-
-
?
5-(aziridin-1-yl)-2,4-dinitrobenzamide + reduced dihydronicotineamide riboside
5-(aziridin-1-yl)-4-hydroxylamino-2-nitrobenzamide + oxidized dihydronicotineamide riboside
-
-
-
?
5-(aziridin-1-yl)-2,4-dinitrobenzamide + reduced dihydronicotineamide riboside
5-(aziridin-1-yl)-4-hydroxylamino-2-nitrobenzamide + oxidized dihydronicotineamide riboside
-
-
-
?
5-(aziridin-1-yl)-2,4-dinitrobenzamide + reduced dihydronicotineamide riboside
5-(aziridin-1-yl)-4-hydroxylamino-2-nitrobenzamide + oxidized dihydronicotineamide riboside
-
-
-
?
alpha-tocopherolquinone + NAD(P)H
reduced alpha-tocopherolquinone + NAD(P)+
-
-
-
-
?
alpha-tocopherolquinone + NAD(P)H
reduced alpha-tocopherolquinone + NAD(P)+
-
-
-
-
?
benzoquinone + NAD(P)+
benzohydroquinone + NAD(P)+
-
no activity with coenzyme Q6 and vitamin K1
-
?
benzoquinone + NAD(P)+
benzohydroquinone + NAD(P)+
-
no reaction with p-benzoquinone
-
-
?
K3[Fe(CN)6] + NAD(P)H
K4[Fe(CN)6] + NAD(P)+
-
no activity with coenzyme Q10
-
?
K3[Fe(CN)6] + NAD(P)H
K4[Fe(CN)6] + NAD(P)+
-
no activity with lipoic acid, cytochrome c and vitamin K1
-
?
K3[Fe(CN)6] + NAD(P)H
K4[Fe(CN)6] + NAD(P)+
-
no activity with lipoic acid, cytochrome c and vitamin K1
-
?
K3[Fe(CN)6] + NAD(P)H
K4[Fe(CN)6] + NAD(P)+
-
no activity with O2, vitamin K3, ubiquinone-30 and 2-p-iodophenyl-3-p-nitrophenyl-5-phenyltetrazolium chloride
-
?
K3[Fe(CN)6] + NAD(P)H
K4[Fe(CN)6] + NAD(P)+
-
no activity with lipoic acid, cytochrome c and vitamin K1
-
?
menadione + 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
-
-
-
?
NAD(P)H + H+ + oxidized 2,6-dichlorophenolindophenol
NAD(P)+ + reduced 2,6-dichlorophenolindophenol
-
-
-
?
NAD(P)H + H+ + oxidized 2,6-dichlorophenolindophenol
NAD(P)+ + reduced 2,6-dichlorophenolindophenol
-
-
-
?
NAD(P)H + H+ + oxidized 2,6-dichlorophenolindophenol
NAD(P)+ + reduced 2,6-dichlorophenolindophenol
-
low activity
-
?
NAD(P)H + H+ + oxidized 2,6-dichlorophenolindophenol
NAD(P)+ + reduced 2,6-dichlorophenolindophenol
-
-
-
?
NAD(P)H + H+ + oxidized 2,6-dichlorophenolindophenol
NAD(P)+ + reduced 2,6-dichlorophenolindophenol
-
-
-
?
NAD(P)H + H+ + oxidized 2,6-dichlorophenolindophenol
NAD(P)+ + reduced 2,6-dichlorophenolindophenol
-
-
-
-
?
NAD(P)H + H+ + oxidized 2,6-dichlorophenolindophenol
NAD(P)+ + reduced 2,6-dichlorophenolindophenol
-
-
-
?
NAD(P)H + H+ + oxidized 2,6-dichlorophenolindophenol
NAD(P)+ + reduced 2,6-dichlorophenolindophenol
-
-
-
-
?
NAD(P)H + H+ + oxidized 2,6-dichlorophenolindophenol
NAD(P)+ + reduced 2,6-dichlorophenolindophenol
-
low activity
-
?
NAD(P)H + H+ + oxidized 2,6-dichlorophenolindophenol
NAD(P)+ + reduced 2,6-dichlorophenolindophenol
-
-
-
?
NAD(P)H + H+ + oxidized 2,6-dichlorophenolindophenol
NAD(P)+ + reduced 2,6-dichlorophenolindophenol
-
-
-
?
NAD(P)H + H+ + oxidized 2,6-dichlorophenolindophenol
NAD(P)+ + reduced 2,6-dichlorophenolindophenol
-
-
-
?
NAD(P)H + H+ + oxidized 2,6-dichlorophenolindophenol
NAD(P)+ + reduced 2,6-dichlorophenolindophenol
-
-
-
-
?
NAD(P)H + H+ + oxidized 2,6-dichlorophenolindophenol
NAD(P)+ + reduced 2,6-dichlorophenolindophenol
-
microsomal enzyme
-
-
NADH + H+ + 17-(allylamino)-17-demethoxygeldanamycin
?
-
NAD(P)H:quinone oxidoreductase 1 in pancreatic cell lines metabolizes the heat shock protein 90 inhibitor 17-(allylamino)-17-demethoxygeldanamycin to the corresponding hydroquinone
-
-
?
NADH + H+ + 17-(allylamino)-17-demethoxygeldanamycin
?
-
NAD(P)H:quinone oxidoreductase 1 metabolizes the heat shock protein 90 inhibitor 17-(allylamino)-17-demethoxygeldanamycin to the corresponding hydroquinone
-
-
?
NADPH + H+ + 17-(allylamino)-17-demethoxygeldanamycin
?
-
NAD(P)H:quinone oxidoreductase 1 in pancreatic cell lines metabolizes the heat shock protein 90 inhibitor 17-(allylamino)-17-demethoxygeldanamycin to the corresponding hydroquinone
-
-
?
NADPH + H+ + 17-(allylamino)-17-demethoxygeldanamycin
?
-
NAD(P)H:quinone oxidoreductase 1 metabolizes the heat shock protein 90 inhibitor 17-(allylamino)-17-demethoxygeldanamycin to the corresponding hydroquinone
-
-
?
NADPH + H+ + oxidized 2,6-dichlorophenolindophenol
NADP+ + reduced 2,6-dichlorophenolindophenol
-
-
-
-
?
NADPH + H+ + oxidized 2,6-dichlorophenolindophenol
NADP+ + reduced 2,6-dichlorophenolindophenol
-
-
-
-
?
NADPH + H+ + quinone
NADP+ + ?
-
TNF alpha and LPS induce Nqo1 mRNA expression
-
-
?
oxidized dichlorophenol-indophenol + NAD(P)H
reduced dichlorophenol-indophenol + NADP+
-
-
-
-
?
oxidized dichlorophenol-indophenol + NAD(P)H
reduced dichlorophenol-indophenol + NADP+
-
-
-
-
?
quinone + NAD(P)H
hydroquinone + NAD(P)+
-
protection of cells against damage by reactive oxygen species generated during oxidative cycling of quinones and semiquinone radicals
-
?
quinone + NAD(P)H
hydroquinone + NAD(P)+
-
possible role in seed germination
-
?
additional information
?
-
-
role of enzyme in protecting against environmental stressors
-
-
-
additional information
?
-
role of enzyme in protecting against environmental stressors
-
-
-
additional information
?
-
role of enzyme in protecting against environmental stressors
-
-
-
additional information
?
-
-
NQO1 activity colocalizes closely with Alzheimer‘s disease pathology supporting a presumed role as an antioxidant system upregulated in response to the oxidative stress of the Alzheimer‘s 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
?
-
-
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
?
-
-
lack of NQO1 in male mice increases benzene-induced hematotoxicity but not genotoxicity or the DNA damage response. NQO1 appears critical in female mice for detoxifying the metabolites of benzene responsible for genotoxicity, hematotoxicity, and induction of the DNA damage response
-
-
-
additional information
?
-
-
V5+ down-regulates Nqo1 at the transcriptional level, possibly through inhibiting the ATP-dependent activation of Nrf2
-
-
-
additional information
?
-
-
ChrR minimizes intracellular H2O2 stress
-
-
-
additional information
?
-
-
ChrR reduces quinones by simultaneous two-electron transfer, avoiding formation of highly reactive semiquinone intermediates and producing quinols that promote tolerance of H2O2
-
-
-
additional information
?
-
-
plays one of the main roles in the bioactivation of quinoidal drugs
-
-
-
additional information
?
-
-
the enzyme is involved in the metabolic activation of carcinogenic aristolochic acid
-
-
-
additional information
?
-
-
the main cytotoxicity mechanism of antitumour aziridinyl-benzoquinones is their two-electron reduction to alkylating products by NAD(P)H:quinone oxidoreductase. In addition to the activation of NQO1 the oxidative stress, presumably initiated by single-electron enzymatic reduction, plays an important role in the cytotoxicity of aziridinyl-substituted quinones
-
-
-
additional information
?
-
-
naphthoquinone-based vitamin (vitamin K1) is not a substrate for purified rat NQO1
-
-
-
additional information
?
-
-
regeneration of alpha-tocopherol may be one of the physiologic functions of this enzyme
-
-
-
additional information
?
-
TmQR2 could play a role in protecting the infected epidermis
-
-
-
additional information
?
-
-
TmQR2 could play a role in protecting the infected epidermis
-
-
-
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
NATURAL SUBSTRATES
NATURAL PRODUCTS
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
P15559
the enzyme catalyzes a detoxification process. QR1 gene expression is induced in response to xenobiotics, oxidants, heavy metals, UV light, and ionisation radiation. The enzyme is part of an electrophilic-induced and/or oxidative stress-induced cellular defense mechanism that includes the induction of more than two dozen defensive genes
-
-
?
NADH + H+ + 17-(allylamino)-17-demethoxygeldanamycin
?
-
NAD(P)H:quinone oxidoreductase 1 in pancreatic cell lines metabolizes the heat shock protein 90 inhibitor 17-(allylamino)-17-demethoxygeldanamycin to the corresponding hydroquinone
-
-
?
NADH + H+ + 2-methyl-1,4-naphthoquinone
NAD+ + 2-methyl-1,4-naphthoquinol
-
-
-
-
?
NADH + H+ + atovaquone
NAD+ + reduced atovaquone
-
atovaquone is 2-[4-(4-chlorophenyl)cyclohexyl]-3-hydroxynaphthalene-1,4-dione
-
-
?
NADH + H+ + ubiquinone
NAD+ + ubiquinone
-
the enzyme plays an essential role in maintaining a reduced ubiquinone-pool during infection (Plasmodium falciparum is the causative agents of malaria). The enzyme is not only essential to parasite survival in vivo but may also contribute to the severity and outcome of disease. Type II NADH:quinone oxidoreductase the membrane-bound respiratory enzyme differs from the canonical NADH:dehydrogenase (complex I), because it is not involved in the vectorial transfer of protons across membranes. In the electron transport chain of Plasmodium, the canonical multimeric complex I (NADH:dehydrogenase) found in mammalian mitochondria is absent, and, instead, the parasite possesses five quinone-dependent oxidoreductases, namely a type II NADH:quinone oxidoreductase (PfNDH2), a malate: quinone oxidoreductase (MQO), a dihydroorotate dehydrogenase (DHOD), a glycerol-3-phosphate dehydrogenase (G3PDH), and a succinate: quinone oxidoreductase (SDH). These enzymes link cytosolic metabolism to mitochondrial metabolism, generating reducing power (ubiquinol) for the bc1 complex and an aa3-type cytochrome oxidase, enabling proton pumping and energy conservation
-
-
?
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+ + 2-methyl-1,4-naphthoquinone
NADP+ + 2-methyl-1,4-naphthoquinol
-
-
-
-
?
quinone + NAD(P)H
hydroquinone + NAD(P)+
-
protection of cells against damage by reactive oxygen species generated during oxidative cycling of quinones and semiquinone radicals
-
?
quinone + NAD(P)H
hydroquinone + NAD(P)+
-
possible role in seed germination
-
?
additional information
?
-
-
role of enzyme in protecting against environmental stressors
-
-
-
additional information
?
-
P58795
role of enzyme in protecting against environmental stressors
-
-
-
additional information
?
-
P0A8G6
role of enzyme in protecting against environmental stressors
-
-
-
additional information
?
-
-
NQO1 activity colocalizes closely with Alzheimer‘s disease pathology supporting a presumed role as an antioxidant system upregulated in response to the oxidative stress of the Alzheimer‘s 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
?
-
-
increased enzyme expression reflects an endogenous defense response against reactive oxygen species-mediated cellular toxicity
-
-
-
additional information
?
-
-
lack of NQO1 in male mice increases benzene-induced hematotoxicity but not genotoxicity or the DNA damage response. NQO1 appears critical in female mice for detoxifying the metabolites of benzene responsible for genotoxicity, hematotoxicity, and induction of the DNA damage response
-
-
-
additional information
?
-
-
V5+ down-regulates Nqo1 at the transcriptional level, possibly through inhibiting the ATP-dependent activation of Nrf2
-
-
-
additional information
?
-
-
ChrR minimizes intracellular H2O2 stress
-
-
-
additional information
?
-
-
plays one of the main roles in the bioactivation of quinoidal drugs
-
-
-
additional information
?
-
-
the enzyme is involved in the metabolic activation of carcinogenic aristolochic acid
-
-
-
additional information
?
-
-
the main cytotoxicity mechanism of antitumour aziridinyl-benzoquinones is their two-electron reduction to alkylating products by NAD(P)H:quinone oxidoreductase. In addition to the activation of NQO1 the oxidative stress, presumably initiated by single-electron enzymatic reduction, plays an important role in the cytotoxicity of aziridinyl-substituted quinones
-
-
-
additional information
?
-
-
regeneration of alpha-tocopherol may be one of the physiologic functions of this enzyme
-
-
-
additional information
?
-
Q5EI63
TmQR2 could play a role in protecting the infected epidermis
-
-
-
additional information
?
-
-
TmQR2 could play a role in protecting the infected epidermis
-
-
-
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
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
-
purified recombinant enzyme contains FAD whereas purified native enzyme does not contain FAD
NADH
-
C-terminal domain forms part of the binding site for the hydrophilic regions of NADH
NADH
-
NDH2 can use both NADH and NADPH as electron donor; PfNDH2 can use both NADH and NADPH as electron donor
NADPH
-
C-terminal domain forms part of the binding site for the hydrophilic regions of NADPH
NADPH
-
NDH2 can use both NADH and NADPH as electron donor; PfNDH2 can use both NADH and NADPH as electron donor
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
METALS and IONS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
As3+
-
induction of enzyme together with heme oxygenase-1 and glutathione S-transferase Ya
Cd2+
Cd2+
-
induction of enzyme together with heme oxygenase-1 and glutathione S-transferase Ya
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
1,4-Naphthohydroquinone
-
competitive vs. 1,4-naphthohydroquinone, noncompetitive vs. NADPH
1-hydroxy-2-[2-(nitrooxy)ethyl]-1-oxo-2-(2,4,6-trinitro-3-(nitro[2-(nitrooxy)ethyl]amino)phenyl)diazanium
-
competitive
1-[3,5-dinitro-2-(1,2,3,4-tetrahydronaphthalen-2-yl)phenyl]-1-oxohydrazinium
-
-
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-(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-[alpha-(4'-nitrophenyl)-beta-acetylethyl]-4-hydroxycoumarin
-
0.02 mM, 50% inhibition
3-[[3-[bis(4-hydroxy-2-oxo-2H-chromen-3-yl)methyl]phenyl](4-hydroxy-2-oxo-4a,8a-dihydro-2H-chromen-3-yl)methyl]-4-hydroxy-2H-chromen-2-one
-
-
3-[[4-[bis(4-hydroxy-2-oxo-2H-chromen-3-yl)methyl]phenyl](4,7-dihydroxy-2-oxo-4a,8a-dihydro-2H-chromen-3-yl)methyl]-4,7-dihydroxy-2H-chromen-2-one
-
-
3-[[4-[bis(4-hydroxy-2-oxo-2H-chromen-3-yl)methyl]phenyl](4-hydroxy-2-oxo-4a,8a-dihydro-2H-chromen-3-yl)methyl]-4-hydroxy-2H-chromen-2-one
-
-
4',5,7-trihydroxyflavone
-
0.01 mM, 61% inhibition, recombinant NAD(P)H:quinone acceptor oxidoreductase 2
4,10-dinitro-5,6-dihydrobenzimidazo[2,1-a]isoquinoline-9-carboxamide 12-oxide
-
-
4,10-dinitro-8-(trifluoromethyl)-5,6-dihydrobenzimidazo[2,1-a]isoquinoline 12-oxide
-
-
5,6-dimethylxanthenone-4-acetic acid
-
tumour blood flow inhibitor, competitive vs. NADH
5-hydroxy-7-bromoacetylflavone
-
0.00018 mM, 50% inhibition, irreversible, useful as affinity label
5-methoxy-1,2-dimethyl-3-(2,4,6-trifluorophenoxymethyl)indole-4,7-dione
-
effective inhibitor of the growth of MiaPaCa-2 cells; indolequinone derivative 10, mechanism based 80% inhibition
5-methoxy-1,2-dimethyl-3-(2-nitrophenoxymethyl)indole-4,7-dione
-
effective inhibitor of the growth of MiaPaCa-2 cells
5-methoxy-1,2-dimethyl-3-(3-nitrophenoxymethyl)indole-4,7-dione
-
effective inhibitor of the growth of MiaPaCaa-2 cells; indolequinone derivative 6, dose dependent inhibition of NQO1 activity in MiaPaCa-2
5-methoxy-1,2-dimethyl-3-(3-pyridyloxymethyl)indole-4,7-dione
-
indolequinone derivative 12, dose dependent inhibition of NQO1 activity in MiaPaCa-2
5-methoxy-1,2-dimethyl-3-(4-nitrophenoxymethyl)indole-4,7-dione
-
effective inhibitor of the growth of MiaPaCa-2 cells
5-methoxy-1,2-dimethyl-3-(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-bromoacetylflavone
-
time-dependent inactivation within 30 s, 0.00074 mM, 50% inhibition
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
benzoquinol
-
shows noncompetitive inhibition in all conditions, it can bind to multiple enzyme forms or sites, even when either of the substrates (NADH or benzoquinone) is present at high concentrations
beta-naphthoflavone
-
0.01 mM, 76% inhibition, recombinant NAD(P)H:quinone acceptor oxidoreductase 2
capsaicin
-
activity is decreased after the treatment with capsaicin or dicoumarol. Quinone metabolites or other reactive forms of capsaicin may bind covalently to NQO1 and thereby inhibit its activity, leading to production of reactive oxygen species; suppresses NQO1 expression and activity. Quinone metabolites or other reactive forms of capsaicin may bind covalently to NQO1 and thereby inhibit its activity, leading to production of reactive oxygen species
Cr6+
-
decrease of enzyme mRNA level together with heme oxygenase-1 and glutathione S-transferase Ya
curcumin
-
inhibition of enzyme activity in vivo and in vitro. Inducues dissociation of complexes of enzyme with tumor suppressor protein p53 leading to degradation of p53, but not of p53 cancer hot-spot mutant R273H
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
quinacrine dihydrochloride
-
0.05 mM, 65-95% inhibition depending on substrate
3,3'-methylene-bis(4-hydroxycoumarin)
-
0.01 mM, 25% inhibition, recombinant NAD(P)H:quinone acceptor oxidoreductase 2
3,3'-methylene-bis(4-hydroxycoumarin)
-
trivial name dicoumarol, slight inhibition
3,3'-methylene-bis(4-hydroxycoumarin)
-
competitive vs. NADH, uncompetitive vs. vitamin K1
5,5'-dithiobis(2-nitrobenzoic acid)
-
1 mM, 67% inhibition, 10 mM, complete inhibition
5-methoxy-1,2-dimethyl-3-[(4-nitrophenoxy)methyl]indole-4,7-dione
-
mechanism-based inhibitor, time- and concentration dependent inhibition that requires the presence of NAD(P)H, 0.0015 mM, complete inhibition after 4 min
5-methoxy-1,2-dimethyl-3-[(4-nitrophenoxy)methyl]indole-4,7-dione
-
ES936, potent inhibitor of NQO1 activity and cell proliferation. Approximately 90% inhibition of enzyme activity after 4 h. Inactivation is dependent upon NADH
bis-3,3'-(4-hydroxycoumarinyl)acetoacetate
-
trivial tromexan, 0.1 mM, 79% inhibition
-
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
dicoumarol
-
lack of effect of inhibition of DT-diaphorase by dicoumarol, when the cells are incubated with dopamine and reserpine. Significant cell death only when RCSN-3 cells are incubated with reserpine and dopamine together with the DT-diaphorase inhibitor dicoumarol
dicoumarol
-
in the presence of 0.050 mM of dicoumarol, the protective effect of bromocriptine against H2O2 is completely abolished
dicumarol
-
most potent competitive inhibitor of QO1. Disadvantages with dicumarol in that it is not selective and can inhibit other enzymes in addition to NQO1 and it can also be extensively protein bound complicating its use in cellular assays
dicumarol
-
inhibits the reduction of chromate by the digiton-permeabilized FLK cells in the presence of NADPH regeneration system. Protects against cytotoxicity by inhibiting NQO1
ES936
-
i.e. 5-methoxy-1,2-dimethyl-3-[(4-nitrophenoxy)methyl]indole-4,7-dione, suicide inhibitor
ES936
-
effective mechanism-based inhibitor. Inhibits NQO1 in a time- and concentration-dependent manner. In agreement with its role as mechanism-based (suicide substrate) inhibitor, requires the presence of cofactor NADH, and therefore a catalytic turnover, for effective enzyme inhibition. At 100 nanomol concentration, ES936 inhibits more than 95% of NQO1 activity in cells within 30 min, and since it is specific, appears to be a more useful biochemical tool than dicumarol for use in routine NQO1 assays
ES936
-
pancreatic tumour xenografts in mice grow significantly slower following treatment with ES936
NAD+
-
noncompetitive inhibition with either substrate when the other substrate is at low concentrations. At high NADH concentrations, NAD and benzoquinone are competitive, indicating they bind to a common site or sites
quercetin
-
0.01 mM, 100% inhibition, recombinant NAD(P)H:quinone acceptor oxidoreductase 2
additional information
-
insensitive to rotenone, Ca2+, platanetin and flavone have no effect on the NADH:2,3-dimethoxy-5-methyl-1,4-benzoquinone reductase activity of the purified enzyme
-
additional information
-
not inhibited by iodoacetate, 4-chloromercuribenzoate, Cu2+, FeSO4, FeCl3, CdSO4, ZnSO4, CuSO4, EDTA, alpha,alpha'-dipyridiyl, o-phenanthroline, dimethylglyoxime, dithizon, NaCN, amytal, veronal, antimycin, 2,4-dinitrophenol and thyroxin
-
additional information
-
not inhibited by o-phenanthroline, KCN, quinacrine, EDTA and 2,3-dimercapto-1-propanol
-
additional information
-
compounds 5-methoxy-1,2-dimethyl-3-(phenoxymethyl)indole-4,7-dione, 6-methoxy-1,2-dimethyl-3-(phenoxymethyl)indole-4,7-dione, 5-methoxy-1,2-dimethyl-3-(2,4-dinitrophenoxymethyl)indole-4,7-dione, 6-methoxy-1,2-dimethyl-3-(2,4-dinitrophenoxymethyl)indole-4,7-dione, 3-(2-fluoro-4-nitrophenoxymethyl)-5-methoxy-1,2-dimethylindole-4,7-dione, 3-(4-fluorophenoxymethyl)-6-methoxy-1,2-dimethylindole-4,7-dione, 5-methoxy-1,2-dimethyl-3-(pyridin-2-yloxymethyl)indole-4,7-dione, 6-methoxy-1,2-dimethyl-3-(pyridin-2-yloxymethyl)indole-4,7-dione, 5-methoxy-1,2-dimethyl-3-(3-pyridyloxymethyl)indole-4,7-dione, 3-methoxy-1,2-dimethyl-3-(3-pyridyloxymethyl)indole-4,7-dione, 5-methoxy-1,2-dimethyl-3-(pyridin-4-yloxymethyl)indole-4,7-dione, 6-methoxy-1,2-dimethyl-3-(pyridin-4-yloxymethyl)indole-4,7-dione, and 5-methoxy-1,2-dimethyl-3-[1-(4-nitrophenoxy)ethyl]indole-4,7-dione are relatively ineffective at inducing growth inhibition. Inhibition of recombinant NQO1 is related to the pKa of the leaving group: compounds with poorer phenolic leaving groups are poor inhibitors whereas those with more acidic leaving groups are more efficient inhibitors
-
additional information
-
fruit and vegetable consumption may repress rather than induce rectal NQO1 phenotype. Consumption of Compositae is associated with lower rectal NQO1 mRNA level. Consumption of Apiaceae is associated with lower rectal NQO1 activity
-
additional information
-
indolequinones with 4-nitrophenoxy, 4-pyridinyloxy, and acetoxy substituents at the (indol-3-yl)methyl position are NADH-dependent inhibitors of recombinant human NQO1, indicative of mechanism-based inhibition. However, those with hydroxy and phenoxy substituents are poor inhibitors of NQO1 enzyme activity, due to attenuated elimination of the leaving group. 4-pyridinyloxy and acetoxy compounds are potent inhibitors of NQO1 activity but relatively poor inhibitors of cell proliferation. Phenoxy compounds, which are not inhibitors of NQO1 enzymatic activity, demonstrate potent growth inhibition
-
additional information
-
growth inhibitory effects of series of methoxystilbenes (E and Z isomers) related to resveratrol on human cancer cell lines, overview
-
additional information
-
synthesis of 2-nitroaryl-1,2,3,4-tetrahydroisoquinolines, nitro-substituted 5,6-dihydrobenzimidazo[2,1-a]isoquinoline N-oxides and related heterocycles as potential bioreducible substrates for the enzymes NAD(P)H: quinone oxidoreductase 1, NQO1, overview
-
additional information
-
almond skin polyphenol extracted with agastrointestinal juice mimic decreases quinone reductase activity. Combining almond skin polyphenol extracted with agastrointestinal juice mimic plus vitamin C has an antagonistic effect
-
additional information
-
enzyme induction effects of series of methoxystilbenes (E and Z isomers) related to resveratrol on murine hepatoma cells, overview
-
additional information
-
microsomal enzyme: not inhibited by dicoumarol, lapachol and p-chloromercuribenzoate
-
additional information
-
the product inhibition pattern expected if WrbA follows a ping pong mechanism is that the pairs NAD/BQ and NADH/BQH2 display competitive inhibition, whereas the pairs NAD/NADH and BQ/BQH2 display non-competitive inhibition
-
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
1,1'-(E)-ethene-1,2-diylbis(2-methoxybenzene)
-
at 12.5 micromol, induces quinone reductase to a greater extent than resveratrol
1,3-dimethoxy-2-[(E)-2-(4-methoxyphenyl)ethenyl]benzene
-
at 12.5 micromol, induces quinone reductase to a greater extent than resveratrol
1-(3,4-dihydroxybenzyl)-1,2,3,4-tetrahydro-6,7-isoquinolinediol
-
up-regulation of enzyme upon exposure to L-dopa and tetrahydropapaveroline
1-methoxy-2-[(E)-2-(4-methoxyphenyl)ethenyl]benzene
-
at 6.3 micromol is 1.8 times more effective than resveratrol as a quinone reductase inducer
1-methoxy-3-[(E)-2-(4-methoxyphenyl)ethenyl]benzene
-
at 12.5 micromol, induces quinone reductase to a greater extent than resveratrol
2-methoxy-5-[(E)-2-(4-methoxyphenyl)ethenyl]phenol
-
at 12.5 micromol, induces quinone reductase to a greater extent than resveratrol
3-nitrobenzanthrone
-
increases protein level and enzymatic activity of NQO1. Up to a 2.5fold increase in NQO1 activity with menadione as substrate in tissues of rats treated with 3-nitrobenzanthrone
3H-1,2-dithiole-3-thione
-
significantly increases cellular NQO1 activity and mRNA levels. Induces NQO1 in a concentration-dependent manner. In SH-SY5Y cells, 2fold induction of cellular NQO1 with 0.01 mM and 3-5.5fold induction of NQO1 with 0.05 and 0.1 mM. 4.5fold increase of NQO1 mRNA between 12 and 24 h after treatment. 40% induction of cellular NQO1 after treatment of primary human neurons at a concentration of 0.01 mM
actinomycin D
-
treatment of the cells with actinomycin D alone for 6 h significantly inhibits the constitutive NQO1 mRNA level by approximately 80%. KTZ- and ITZ-mediated Nqo1 induction is completely inhibited
alpha-methylbenzyl isothiocyanate
-
in vivo, the organ most susceptible to the inductive activity of the isothiocyanates is the urinary bladder, with alpha-methylbenzyl isothiocyanate and cyclohexylmethyl isothiocyanate being the most effective. Inductive activity in the bladder in vivo does not correlate with that in bladder cells in vitro
bromocriptine
-
significantly upregulates expression and activity (911% of untreated control) of NQO1, attenuates increase in protein-bound quinone in H2O2-treated PC12 cells, and protects PC12 cells against oxidative damage. Bromocriptine increases the expression and nuclear translocation of a basic leucine zipper transcription factor Nrf2, involved in the regulation of the enzyme
cyclohexylmethyl isothiocyanate
-
in vivo, the organ most susceptible to the inductive activity of the isothiocyanates is the urinary bladder, with alpha-methylbenzyl isothiocyanate and cyclohexylmethyl isothiocyanate being the most effective. Inductive activity in the bladder in vivo does not correlate with that in bladder cells in vitro
Eugenol
-
increases expression and activity of enzyme by NF-E2 related factor2 binding to antioxidant response element in enzyme gene; increases the expression and activity of NAD(P)H:quinone oxidoreductase through NF-E2 related factor2 binding to antioxidant response element in QR gene in a dose-dependent manner
itraconazole
-
induces NQO1 mRNA and enzymatic activity levels in a concentration- and time-dependent manner in wild-type but not aryl hydrocarbon receptor-deficient Hepa-1c1c7 cells. Increases NQO1 de novo RNA synthesis without significantly affecting the levels of existing RNA. 50 micromol shows maximum NQO1 mRNA induction
ketoconazole
-
induces NQO1 mRNA and enzymatic activity levels in a concentration- and time-dependent manner in wild-type but not aryl hydrocarbon receptor-deficient Hepa-1c1c7 cells. Increases NQO1 de novo RNA synthesis without significantly affecting the levels of existing RNA. 25 micromol shows maximum NQO1 mRNA induction
L-Dopa
-
up-regulation of enzyme upon exposure to L-dopa and tetrahydropapaveroline
resveratrol
-
at 25 micromol increases quinone reductase activity by 1.5fold. Resveratrol induces quinone reductase activity of the wild type Hepa-1c1c7 cells to the same extent as the mutant c1 cells that lack a phase I enzyme
rutaecarpine
-
induces enzyme activity and gene expression by transactivation of activator protein-1 in a dose-dependent manner; isolated from Evodia rutaecarpa, induces QR gene expression and activity through increase of activator protein-1, Evodia rutaecarpa is used in traditional Chinese medicine
Clofibrate
-
administration to animals for 5 to 10 days, increase in enzyme protein and activity
Clofibrate
-
administration to animals for 5 to 10 days, increase in enzyme protein and activity
sulforaphane
-
at a concentration of 5 micromol significantly induces NQO1 mRNA in both wild-type and C12 cells
additional information
-
vegetable consumption only is not associated with NQO1 mRNA level or NQO1 activity
-
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
-
compared to resveratrol, analogues with ortho-methoxy substituents are more potent inducers of quinone reductase and exert their activity in a qualitatively different manner
-
additional information
-
heating at 42°C for 1 h significantly increases the expression of NQO1 in cancer cells
-
additional information
-
almond skin polyphenol extracted with methanol increases quinone reductase activity. Combining almond skin polyphenol extracted with methanol plus vitamin C results in a synergistic interaction
-
additional information
-
about 10fold induction of enzyme expression by H2O2
-
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.115
2-methoxy-5-(methoxymethyl)-2,5-cyclohexadiene-1,4-dione
-
-
0.012
3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium
-
recombinant NAD(P)H:quinone acceptor oxidoreductase 2
0.025 - 0.04
5-(1-aziridinyl)-3-(hydroxymethyl)-2-(3-hydroxy-1-propenyl)-1-methyl-1H-indole-4,7-dione
0.007
2,6-dichlorophenolindophenol
-
recombinant NAD(P)H:quinone acceptor oxidoreductase 2
0.018
2,6-dichlorophenolindophenol
-
recombinant NAD(P)H:quinone acceptor oxidoreductase 1
0.025
5-(1-aziridinyl)-3-(hydroxymethyl)-2-(3-hydroxy-1-propenyl)-1-methyl-1H-indole-4,7-dione
-
-
0.027
5-(1-aziridinyl)-3-(hydroxymethyl)-2-(3-hydroxy-1-propenyl)-1-methyl-1H-indole-4,7-dione
-
-
0.04
5-(1-aziridinyl)-3-(hydroxymethyl)-2-(3-hydroxy-1-propenyl)-1-methyl-1H-indole-4,7-dione
-
-
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
0.028
dihydronicotinamide riboside
-
recombinant NAD(P)H:quinone acceptor oxidoreductase 2
0.07
dihydronicotinamide riboside
-
recombinant NAD(P)H:quinone acceptor oxidoreductase 1
0.04 - 0.05
menadione
-
in untreated vesicles, in low salt disrupted membranes and in French-press treated preparations
0.0625
NADPH
mutant Y140F, pH 7.5, temperature not specified in the publication
0.0656
NADPH
wild-type, pH 7.5, temperature not specified in the publication
0.0915
NADPH
mutant W139F, pH 7.5, temperature not specified in the publication
0.195
NADPH
mutant W139I, pH 7.5, temperature not specified in the publication
0.225
NADPH
mutant W139A, pH 7.5, temperature not specified in the publication
0.395
NADPH
mutant N143A, pH 7.5, temperature not specified in the publication
0.403
NADPH
mutant N143L, pH 7.5, temperature not specified in the publication
additional information
additional information
-
steady-state kinetic analysis of the quinone reductase activity
-
additional information
additional information
-
WrbA steady-state kinetics, overview. Initial velocity as a function of either NADH or benzoquinone concentration present one or two Michaelis-Menten phases depends on the temperature at which the enzyme is held prior to assay. The effect of temperature is reversible, suggesting an intramolecular conformational process
-
additional information
additional information
-
Michaelis-Menten kinetics and first-order rate constants with NADH and quinone substrates, overview
-
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
2000
2,5-diaziridinyl-3-(hydroxymethyl)-6-methyl-1,4-benzoquinone
Rattus norvegicus
-
pH 7.0, 25°C
11
3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium
Homo sapiens
-
recombinant NAD(P)H:quinone acceptor oxidoreductase 2
46.7
2,6-dichlorophenolindophenol
Homo sapiens
-
recombinant NAD(P)H:quinone acceptor oxidoreductase 2
600
2,6-dichlorophenolindophenol
Homo sapiens
-
recombinant NAD(P)H:quinone acceptor oxidoreductase 1
0.01
5-(aziridin-1-yl)-2,4-dinitrobenzamide
Homo sapiens
-
recombinant NAD(P)H:quinone acceptor oxidoreductase 2
6
5-(aziridin-1-yl)-2,4-dinitrobenzamide
Homo sapiens
-
recombinant NAD(P)H:quinone acceptor oxidoreductase 2
43.3
dihydronicotinamide riboside
Homo sapiens
-
recombinant NAD(P)H:quinone acceptor oxidoreductase 2
517
dihydronicotinamide riboside
Homo sapiens
-
recombinant NAD(P)H:quinone acceptor oxidoreductase 1
18.7
NADPH
Escherichia coli
P39315
mutant N143A, pH 7.5, temperature not specified in the publication
25.2
NADPH
Escherichia coli
P39315
mutant N143L, pH 7.5, temperature not specified in the publication
32.3
NADPH
Escherichia coli
P39315
mutant W139A, pH 7.5, temperature not specified in the publication
34.2
NADPH
Escherichia coli
P39315
wild-type, pH 7.5, temperature not specified in the publication
37.1
NADPH
Escherichia coli
P39315
mutant W139F, pH 7.5, temperature not specified in the publication
45.2
NADPH
Escherichia coli
P39315
mutant Y140F, pH 7.5, temperature not specified in the publication
53.5
NADPH
Escherichia coli
P39315
mutant W139I, pH 7.5, temperature not specified in the publication
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
48
NADPH
Escherichia coli
P39315
mutant N143A, pH 7.5, temperature not specified in the publication
5
63
NADPH
Escherichia coli
P39315
mutant N143L, pH 7.5, temperature not specified in the publication
5
144
NADPH
Escherichia coli
P39315
mutant W139A, pH 7.5, temperature not specified in the publication
5
278
NADPH
Escherichia coli
P39315
mutant W139I, pH 7.5, temperature not specified in the publication
5
407
NADPH
Escherichia coli
P39315
mutant W139F, pH 7.5, temperature not specified in the publication
5
522
NADPH
Escherichia coli
P39315
wild-type, pH 7.5, temperature not specified in the publication
5
727
NADPH
Escherichia coli
P39315
mutant Y140F, pH 7.5, temperature not specified in the publication
5
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.00005
1,amino-4-[(4-amino-3-sulfophenyl)amino]-anthraquinone-2-sulfonic acid
-
-
0.000077
1-amino-4-[(3-carboxyphenyl)amino]-anthraquinone-2-sulfonic acid
-
-
0.095
1-hydroxy-2-[2-(nitrooxy)ethyl]-1-oxo-2-(2,4,6-trinitro-3-(nitro[2-(nitrooxy)ethyl]amino)phenyl)diazanium
-
pH 7.0, 25°C
0.0001 - 0.001
2-Heptyl-4-hydroxyquinoline-N-oxide
-
depending on enzyme solubilization
0.0031
hydroxy(oxo)(3,6,8-trinitro-9H-carbazol-1-yl)ammonium
-
pH 7.0, 25°C
0.001 - 0.002
phenylmercuric acetate
-
depending on enzyme solubilization
0.0075
1,4-Naphthohydroquinone
-
vs. 1,4-naphthoquinone, value derived from from intercept
0.008
1,4-Naphthohydroquinone
-
vs. NADPH, value derived from from slope
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
IC50 VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.025
2,2'-dimethoxy-trans-stilbene
Mus musculus
-
above, pH not specified in the publication, 37°C
0.025
2,4'-dimethoxy-trans-stilbene
Mus musculus
-
above, pH not specified in the publication, 37°C
0.025
2,4,4'-trimethoxy-trans-stilbene
Mus musculus
-
above, pH not specified in the publication, 37°C
0.0103
2,6,4'-trimethoxy-trans-stilbene
Mus musculus
-
pH not specified in the publication, 37°C
0.025
2-hydroxy-4'-methoxy-trans-stilbene
Mus musculus
-
above, pH not specified in the publication, 37°C
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)
0.025
3,4'-dimethoxy-trans-stilbene
Mus musculus
-
above, pH not specified in the publication, 37°C
0.025
3,4,4'-trimethoxy-trans-stilbene
Mus musculus
-
above, pH not specified in the publication, 37°C
0.025
3,5-dihydroxy-4'-methoxy-cis-stilbene
Mus musculus
-
above, pH not specified in the publication, 37°C
0.025
3,5-dihydroxy-4'-methoxy-trans-stilbene
Mus musculus
-
above, pH not specified in the publication, 37°C
0.000255
3-(2,4-difluorophenoxymethyl)-6-methoxy-1,2-dimethylindole-4,7-dione
Homo sapiens
-
-
0.004654
3-(2-fluoro-4-nitrophenoxymethyl)-5-methoxy-1,2-dimethylindole-4,7-dione
Homo sapiens
-
-
0.000529
3-(2-fluoro-4-nitrophenoxymethyl)-6-methoxy-1,2-dimethylindole-4,7-dione
Homo sapiens
-
-
0.025
3-hydroxy-4'-methoxy-cis-stilbene
Mus musculus
-
above, pH not specified in the publication, 37°C
0.025
3-hydroxy-4'-methoxy-trans-stilbene
Mus musculus
-
above, pH not specified in the publication, 37°C
0.025
3-hydroxy-4,4'-dimethoxy-trans-stilbene
Mus musculus
-
above, pH not specified in the publication, 37°C
0.0005 - 0.0225
3-[[3-[bis(4-hydroxy-2-oxo-2H-chromen-3-yl)methyl]phenyl](4-hydroxy-2-oxo-4a,8a-dihydro-2H-chromen-3-yl)methyl]-4-hydroxy-2H-chromen-2-one
0.00025 - 0.055
3-[[4-[bis(4-hydroxy-2-oxo-2H-chromen-3-yl)methyl]phenyl](4,7-dihydroxy-2-oxo-4a,8a-dihydro-2H-chromen-3-yl)methyl]-4,7-dihydroxy-2H-chromen-2-one
0.00011 - 0.02
3-[[4-[bis(4-hydroxy-2-oxo-2H-chromen-3-yl)methyl]phenyl](4-hydroxy-2-oxo-4a,8a-dihydro-2H-chromen-3-yl)methyl]-4-hydroxy-2H-chromen-2-one
0.025
4,4'-dimethoxy-cis-stilbene
Mus musculus
-
above, pH not specified in the publication, 37°C
0.025
4,4'-dimethoxy-trans-stilbene
Mus musculus
-
above, pH not specified in the publication, 37°C
0.000427
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
0.0081
2,4,4'-trimethoxy-cis-stilbene
Mus musculus
-
pH not specified in the publication, 37°C
0.000015
2-benzyl-1-hydroxy-3H-benzo[f]chromen-3-one
Homo sapiens
-
without bovine serum albumin, in 50 mM phosphate buffer, at pH 7.5 and 25°C
0.000465
2-benzyl-1-hydroxy-3H-benzo[f]chromen-3-one
Homo sapiens
-
with 0.002 mM bovine serum albumin, in 50 mM phosphate buffer, at pH 7.5 and 25°C
0.041
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
0.0085
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
0.024
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 0.14% (v/v) bovine serum albumin, at pH 7.5, 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
0.000062
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 0.14% (v/v) bovine serum albumin, at pH 7.5, 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
0.00000041
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 0.14% (v/v) bovine serum albumin, at pH 7.5, 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
0.0000049
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 0.14% (v/v) bovine serum albumin, at pH 7.5, 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
0.00000042
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 0.14% (v/v) bovine serum albumin, at pH 7.5, 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
0.000014
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
0.028
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
0.035
3,3'-[(4-hydroxyphenyl)methanediyl]bis(4-hydroxy-2H-chromen-2-one)
Homo sapiens
-
in the presence of bovine serum albumin
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
0.0051
3,4,4'-trimethoxy-cis-stilbene
Mus musculus
-
pH not specified in the publication, 37°C
0.007
3,4,4'-trimethoxy-cis-stilbene
Homo sapiens
-
pH not specified in the publication, 37°C, IMR-90 cells
0.000015
3,4,5,4'-tetramethoxy-cis-stilbene
Homo sapiens
-
pH not specified in the publication, 37°C, MCF-7 cells
0.00002
3,4,5,4'-tetramethoxy-cis-stilbene
Homo sapiens
-
pH not specified in the publication, 37°C, HCT-116 cells; pH not specified in the publication, 37°C, IMR-90 cells
0.000034
3,4,5,4'-tetramethoxy-cis-stilbene
Mus musculus
-
pH not specified in the publication, 37°C
0.00016
3,4,5,4'-tetramethoxy-trans-stilbene
Homo sapiens
-
pH not specified in the publication, 37°C, IMR-90 cells
0.00022
3,4,5,4'-tetramethoxy-trans-stilbene
Homo sapiens
-
pH not specified in the publication, 37°C, MCF-7 cells
0.00053
3,4,5,4'-tetramethoxy-trans-stilbene
Homo sapiens
-
pH not specified in the publication, 37°C, HCT-116 cells
0.001
3,4,5,4'-tetramethoxy-trans-stilbene
Mus musculus
-
pH not specified in the publication, 37°C
0.00012
3,5,4'-trimethoxy-cis-stilbene
Homo sapiens
-
pH not specified in the publication, 37°C, MCF-7 cells
0.00022
3,5,4'-trimethoxy-cis-stilbene
Homo sapiens
-
pH not specified in the publication, 37°C, HCT-116 cells
0.00023
3,5,4'-trimethoxy-cis-stilbene
Homo sapiens
-
pH not specified in the publication, 37°C, IMR-90 cells
0.00059
3,5,4'-trimethoxy-cis-stilbene
Mus musculus
-
pH not specified in the publication, 37°C
0.0011
3,5,4'-trimethoxy-trans-stilbene
Homo sapiens
-
pH not specified in the publication, 37°C, MCF-7 cells
0.0021
3,5,4'-trimethoxy-trans-stilbene
Homo sapiens
-
pH not specified in the publication, 37°C, IMR-90 cells
0.0052
3,5,4'-trimethoxy-trans-stilbene
Mus musculus
-
pH not specified in the publication, 37°C
0.0057
3,5,4'-trimethoxy-trans-stilbene
Homo sapiens
-
pH not specified in the publication, 37°C, HCT-116 cells
0.000031
3-(3,4-dimethylbenzyl)-4-hydroxy-2H-chromen-2-one
Homo sapiens
-
without bovine serum albumin, in 50 mM phosphate buffer, at pH 7.5 and 25°C
0.0016
3-(3,4-dimethylbenzyl)-4-hydroxy-2H-chromen-2-one
Homo sapiens
-
with 0.002 mM bovine serum albumin, in 50 mM phosphate buffer, at pH 7.5 and 25°C
0.0000099
3-(3,4-dimethylbenzyl)-4-hydroxy-6,7-dimethyl-2H-chromen-2-one
Homo sapiens
-
without bovine serum albumin, at pH 7.5, 25°C
0.0000099
3-(3,4-dimethylbenzyl)-4-hydroxy-6,7-dimethyl-2H-chromen-2-one
Homo sapiens
-
without bovine serum albumin, in 50 mM phosphate buffer, at pH 7.5 and 25°C
0.000192
3-(3,4-dimethylbenzyl)-4-hydroxy-6,7-dimethyl-2H-chromen-2-one
Homo sapiens
-
with 0.14% (v/v) bovine serum albumin, at pH 7.5, 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
0.000035
3-benzyl-4-hydroxy-2H-benzo[h]chromen-2-one
Homo sapiens
-
without bovine serum albumin, in 50 mM phosphate buffer, at pH 7.5 and 25°C
0.00088
3-benzyl-4-hydroxy-2H-benzo[h]chromen-2-one
Homo sapiens
-
with 0.002 mM bovine serum albumin, in 50 mM phosphate buffer, at pH 7.5 and 25°C
0.000144
3-benzyl-4-hydroxy-2H-chromen-2-one
Homo sapiens
-
without bovine serum albumin, in 50 mM phosphate buffer, at pH 7.5 and 25°C
0.0032
3-benzyl-4-hydroxy-2H-chromen-2-one
Homo sapiens
-
with 0.002 mM bovine serum albumin, in 50 mM phosphate buffer, at pH 7.5 and 25°C
0.000039
3-benzyl-4-hydroxy-6,7-dimethyl-2H-chromen-2-one
Homo sapiens
-
without bovine serum albumin, in 50 mM phosphate buffer, at pH 7.5 and 25°C
0.00066
3-benzyl-4-hydroxy-6,7-dimethyl-2H-chromen-2-one
Homo sapiens
-
with 0.002 mM bovine serum albumin, in 50 mM phosphate buffer, at pH 7.5 and 25°C
0.0034
3-hydroxy-4,4'-dimethoxy-cis-stilbene
Homo sapiens
-
pH not specified in the publication, 37°C, HCT-116 cells
0.0042
3-hydroxy-4,4'-dimethoxy-cis-stilbene
Homo sapiens
-
pH not specified in the publication, 37°C, MCF-7 cells
0.006
3-hydroxy-4,4'-dimethoxy-cis-stilbene
Homo sapiens
-
pH not specified in the publication, 37°C, IMR-90 cells
0.025
3-hydroxy-4,4'-dimethoxy-cis-stilbene
Mus musculus
-
above, pH not specified in the publication, 37°C
0.0005
3-[[3-[bis(4-hydroxy-2-oxo-2H-chromen-3-yl)methyl]phenyl](4-hydroxy-2-oxo-4a,8a-dihydro-2H-chromen-3-yl)methyl]-4-hydroxy-2H-chromen-2-one
Homo sapiens
-
-
0.0225
3-[[3-[bis(4-hydroxy-2-oxo-2H-chromen-3-yl)methyl]phenyl](4-hydroxy-2-oxo-4a,8a-dihydro-2H-chromen-3-yl)methyl]-4-hydroxy-2H-chromen-2-one
Homo sapiens
-
in the presence of bovine serum albumin
0.00025
3-[[4-[bis(4-hydroxy-2-oxo-2H-chromen-3-yl)methyl]phenyl](4,7-dihydroxy-2-oxo-4a,8a-dihydro-2H-chromen-3-yl)methyl]-4,7-dihydroxy-2H-chromen-2-one
Homo sapiens
-
-
0.055
3-[[4-[bis(4-hydroxy-2-oxo-2H-chromen-3-yl)methyl]phenyl](4,7-dihydroxy-2-oxo-4a,8a-dihydro-2H-chromen-3-yl)methyl]-4,7-dihydroxy-2H-chromen-2-one
Homo sapiens
-
in the presence of bovine serum albumin
0.00011
3-[[4-[bis(4-hydroxy-2-oxo-2H-chromen-3-yl)methyl]phenyl](4-hydroxy-2-oxo-4a,8a-dihydro-2H-chromen-3-yl)methyl]-4-hydroxy-2H-chromen-2-one
Homo sapiens
-
-
0.02
3-[[4-[bis(4-hydroxy-2-oxo-2H-chromen-3-yl)methyl]phenyl](4-hydroxy-2-oxo-4a,8a-dihydro-2H-chromen-3-yl)methyl]-4-hydroxy-2H-chromen-2-one
Homo sapiens
-
in the presence of bovine serum albumin
0.0000063
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
0.02233
ethyl bis(4-hydroxy-2-oxo-2H-chromen-3-yl)acetate
Homo sapiens
-
with 0.002 mM bovine serum albumin, in 50 mM phosphate buffer, at pH 7.5 and 25°C
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
0.00024
-
24 h after after oral administration of vitamin E; 48 h after oral administration of manganese; control, 24 h
0.001
-
below, recombinant enzyme NQO1, substrate 10a, pH not specified in the publication, 37°C; below, recombinant enzyme NQO1, substrate 10f, pH not specified in the publication, 37°C; below, recombinant enzyme NQO1, substrate 10g, pH not specified in the publication, 37°C; below, recombinant enzyme NQO1, substrate 10h, pH not specified in the publication, 37°C; below, recombinant enzyme NQO1, substrate 10o, pH not specified in the publication, 37°C; below, recombinant enzyme NQO1, substrate 11d, pH not specified in the publication, 37°C; below, recombinant enzyme NQO1, substrate 11e, pH not specified in the publication, 37°C; below, recombinant enzyme NQO1, substrate 11h, pH not specified in the publication, 37°C; below, recombinant enzyme NQO1, substrate 11i, pH not specified in the publication, 37°C; below, recombinant enzyme NQO1, substrate 11k, pH not specified in the publication, 37°C; below, recombinant enzyme NQO1, substrate 11l, pH not specified in the publication, 37°C
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
0.039
-
activity in liver microsomes, reduction of menadione, cofactor NADPH
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
0.09
-
in kidney of control rats and in lung of rats treated with 40 mg/kg of 3-nitrobenzanthrone
0.11
-
recombinant enzyme NQO1, substrate 10b, pH not specified in the publication, 37°C
0.121
-
activity in liver cytosol, reduction of 2,6-dichlorophenolindophenol, cofactor NADPH
0.128
-
activity in liver cytosol, reduction of 2,6-dichlorophenolindophenol, cofactor NADH
0.15
-
in kidney of rats treated with 0.4 or 4 mg/kg of 3-nitrobenzanthrone
0.153
-
activity in liver microsomes, reduction of menadione, cofactor NADH
0.157
-
activity in liver microsomes, reduction of 2,6-dichlorophenolindophenol, cofactor NADPH
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
0.63
-
activity in liver microsomes, reduction of 2,6-dichlorophenolindophenol, cofactor NADH
1400
substrate 2,6-dichlorophenolindophenol, pH 7.2, 37°C; substrate [Fe(CN)6]3-, pH 7.2, 37°C
6700
substrate 2,3-dihydroxy-5-methyl-1,4-benzoquinone, pH 7.2, 37°C
additional information
additional information
-
230000.0 units/mg, 1 unit is defined as the amount of enzyme causing a decrease in absorbance at 340 nm of 0.001/min
additional information
-
1400000.0, 1 unit is defined as the amount of enzyme causing a decrease in absorbance at 340 nm of 0.001/min
additional information
-
quinone or quinone-like compounds reduction assay with a specific activity ranging from 0.92-4.6 U/mg of protein
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
7.4
7.5
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
pH RANGE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
3.7 - 4.8
-
pH 3.7: about 45% of maximal activity, pH 4.8: about 55% of maximal activity
5 - 9
-
pH 5.0: about 45% of maximal activity, pH 9.0: about 55% of maximal activity
5.5 - 7.5
-
the enzyme maintains greater than 90% of its maximal activity between pH 5.5 and 7.5
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
25
37
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
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
-
pulmonary arterial endothelial cell. Increase in enzyme protein and activity upon hyperoxia, i.e. exposure to 95% O2 for 48 h
-
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
-
H2O2-scavenging and growth of wild-type, overexpressing, and knockout cells, overview
-
the ratio of frontal to cerebellar NQO1 activity is significantly increased in patients with Alzheimer‘s disease versus controls
-
the ratio of frontal to cerebellar NQO1 activity is significantly increased in patients with Alzheimer‘s disease versus controls
the gene for QR2 is isolated from an expressed sequence tag collection derived from the epidermis of a diploid Triticum monococcum L. 24 h after inoculation with the powdery mildew fungus Blumeria graminis EO Speer f. sp. tritici Em. Marchal. TmQR1 is repressed while TmQR2 is induced in the epidermis during powdery mildew infection. TmQR2 can play a role in protecting the infected epidermis
-
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
-
; 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.
-
; 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
-
the ratio of frontal to cerebellar NQO1 activity is significantly increased in patients with Alzheimer‘s disease versus controls, specific localization to astrocytes and neurites surrounding senile plaques. Neuronal NQO1 staining seen in frontal cortex of Alzheimer‘s disease patients is absent in frontal cortex of controls, but is found to the same extent in neurons of the substantia nigra of both Alzheimer‘s disease patients and controls
BE human colon adenocarcinoma cells, stably NQO1-transfected BE-NQ cells69
-
pulmonary arterial endothelial cell. Increase in enzyme protein and activity upon hyperoxia, i.e. exposure to 95% O2 for 48 h
-
; 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
-
in the Sprague Dawley strain, gender dimorphic expression of Nqo1 with female mRNA, protein, and activity levels being significantly higher than in males. Minimal differences in Nqo1 mRNA, protein, and activity levels between August Copenhagen x Irish males and females
-
-
14080, 394352, 394354, 394356, 394357, 394362, 394363, 394366, 394371, 394382, 657644, 657654, 658402, 671034, 690145, 695280, 724747
-
wild-type p53 breast cancer cell lines MCF7 transfected with MCF7-NQO1 to overexpress NQO1, MCF7-SUP8 to knockdown NQO1
-
upregulation or overexpression of the enzyme in tumours
additional information
-
the enzyme is present in a wide range of tissue and cell types including the pulmonary endothelium and other lung cells
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
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
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
-
-
-
-
the membrane-bound respiratory enzymes differs from the canonical NADH: dehydrogenase (complex I), because it is not involved in the vectorial transfer of protons across membranes. The enzyme possesses an amphipathic alpha-helix, which is likely to anchor the enzyme into the lipid bilayer
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
PDB
SCOP
CATH
ORGANISM
UNIPROT
Deinococcus radiodurans (strain ATCC 13939 / DSM 20539 / JCM 16871 / LMG 4051 / NBRC 15346 / NCIMB 9279 / R1 / VKM B-1422)
Deinococcus radiodurans (strain ATCC 13939 / DSM 20539 / JCM 16871 / LMG 4051 / NBRC 15346 / NCIMB 9279 / R1 / VKM B-1422)
Pseudomonas aeruginosa (strain ATCC 15692 / DSM 22644 / CIP 104116 / JCM 14847 / LMG 12228 / 1C / PRS 101 / PAO1)
Pseudomonas aeruginosa (strain ATCC 15692 / DSM 22644 / CIP 104116 / JCM 14847 / LMG 12228 / 1C / PRS 101 / PAO1)
Pseudomonas aeruginosa (strain ATCC 15692 / DSM 22644 / CIP 104116 / JCM 14847 / LMG 12228 / 1C / PRS 101 / PAO1)
Streptococcus mutans serotype c (strain ATCC 700610 / UA159)
Streptococcus mutans serotype c (strain ATCC 700610 / UA159)
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
21000
30835
32000
52000
55000
60000
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
dimer
homodimer
monomer
tetramer
additional information
-
dimer-tetramer assembly equilibrium documented for apoWrbA by analytical ultracentrifugation, large effect of temperature on the subunit assembly state of both apo- and holoWrbA, overview
tetramer
-
three subunits of the tetrameric enzyme contribute to each of four identical, cavernous active sites that appear to accommodate NAD(P)H or various quinones, but not simultaneously, suggesting an obligate tetramer with a ping-pong mechanism in which NAD departs before oxidized quinone binds
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
POSTTRANSLATIONAL MODIFICATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
no glycoprotein
no glycoprotein
-
very unstable posttranslational modification is suggested that is not detectable by mass spectrometry
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
Crystallization/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
native enzyme and in complex with NADPH. The N-terminal domain, which adopts the Rossmann fold, provides a platform for NADPH binding, whereas the C-terminal domain, which contains a hydrophobic pocket connected to the NADPH-binding site, plays important roles in substrate binding. Asn143 near the NADPH-binding site is involved in substrate binding and catalysis
with and without FMN using the sitting drop vapor-diffusion technique
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
-
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, 2.8 A resolution
-
hydrophilic isoform in the presence of FAD, hanging drop diffusion, 10 mg/ml enzyme, in 200 mM potassium phosphate, 0.5 mM EDTA, 0.5 mM, FAD, pH 8.0, 45-50% saturation of ammonium sulfate
-
hanging drop method, crystals from a solution of 10 mg/ml enzyme, 1.45 M ammonium sulfate, 0.5% polyethylene glycol 8000, 30 mM Cibacron blue and 150 mM imidazole, pH 7.0, complex with NADP+ or duroquinone, 2.1 A resolution, structure and substrate binding mechanism
-
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
TEMPERATURE STABILITY
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
GENERAL STABILITY
ORGANISM
UNIPROT
LITERATURE
stable to dialysis against 0.01 M potassium phosphate buffer, pH 7.5 and 0.01 M Tris buffer, pH 8.2 and 8.9, 16 h or more at 3°C
-
sucrose, 0.25 M, essential for stabilization during storage at -20°C and purification
-
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
STORAGE STABILITY
ORGANISM
UNIPROT
LITERATURE
5°C, 0.05 M sodium phosphate, pH 8, enzyme D-II is stable for 1 month, enzyme D-I loses 30% of its activity after 1 week
-
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
blue affinity column chromatography, Resource Q column chromatography, and Superdex 200 gel filtration
-
by affinity chromatography
by affinity chromatography; of the recombinant protein by cibacron blue affinity chromatography
-
purified as a C-terminal His tag fusion by ultracentrifugation and gel filtration, to apparent homogeneity
-
recombinant enzyme
recombinant NAD(P)H:quinone acceptor oxidoreductase 2, affinity chromatography on Affi-gel blue
-
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
expressed in Escherichia coli NADH dehydrogenase knockout strain ANN0222; expression in Escherichia coli
-
expression in Escherichia coli
full-length cDNA of PIFI without a stop codon inserted into the pRZ238 vector, encoding a carboxy-terminal fusion of PIFI onto GFP under control of a cauliflower mosaic virus 35S promoter
-
into pET21a, His-tagged version overexpressed in Escherichia coli BL21 Origami competent cells
-
into the pET30-LIC vector, overexpressed in Escherichia coli BL21(DE3)
-
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
EXPRESSION
ORGANISM
UNIPROT
LITERATURE
Sudan I induces NQO1 expression in rat liver, kidney, and lung, real-time polymerase chain reaction expression analysis
-
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
ENGINEERING
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
N143A
residue near NADPH-binding site. About 10% of wild-type activity
N143L
residue near NADPH-binding site. About 10% of wild-type activity
W139A
residue near NADPH-binding site. About 30% of wild-type activity
W139F
residue near NADPH-binding site. Activity comparable to wild-type
W139I
residue near NADPH-binding site. About 50% of wild-type activity
Y140A
residue near NADPH-binding site. Almost complete loss of activity
Y140F
residue near NADPH-binding site. Activity comparable to wild-type
Y140I
residue near NADPH-binding site. Almost complete loss of activity
C609T
additional information
C609T
-
no significant differences between distributions of NQO1 C609T genotypes in patients with prostate cancer and controls
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
additional information
-
T-DNA insertion mutant pifi (for postillumination chlorophyll fluorescence increase), which possesses an intact NDH complex, but lacks the NDH-dependent chlorophyll fluorescence increase after turning off actinic light. Pifi mutant exhibits a lower capacity for nonphotochemical quenching, but similar CO2 assimilation rates, photosystem II quantum efficiencies, and reduction levels of the primary electron acceptor of PSII (1 2 qL) as compared with the wild-type. Pifi mutant grows normally under optimal conditions, but exhibits greater sensitivity to photoinhibition and long-term mild heat stress than wild-type plants
additional information
enzyme knockout mutant, no phenotypes, but N-trichloromethyl-mercapto-4-cyclohexen-1,2-dicarboximide and 8-hydroxyquinoline significantly inhibit growth of mutant relative to growth of wild-type
additional information
-
mdaB mutant can be grown in microaerophilic conditions. The mutant is more sensitive to oxidative stress reagents such as H2O2, cumene hydroperoxide, t-butyl hydroperoxide, and paraquat. Protein (migration mass of about 26 kDa) is significantly upexpressed in the mutant compared to the wild-type
additional information
-
mdaB mutant can be grown in microaerophilic conditions. The mutant is more sensitive to oxidative stress reagents such as H2O2, cumene hydroperoxide, t-butyl hydroperoxide, and paraquat. Protein (migration mass of about 26 kDa) is significantly upexpressed in the mutant compared to the wild-type
-
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
additional information
-
construction of ChrR overexpressing and knockout mutant strains showing increased and abolished tolerance of H2O2, respectively, enhancing the activity of ChrR in a chromate-remediating bacterial strain may not only increase the rate of chromate transformation, it may also augment the capacity of these cells to withstand the unavoidable production of H2O2 that accompanies chromate reduction, overview
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
APPLICATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
analysis
biotechnology
the flavoprotein WrbA from Escherichia coli represents a new family of multimeric flavodoxin-like proteins implicated in cell protection against oxidative stress, WrbA has NAD(P)H: quinone reductase activity, forms multimers and binds FMN only weakly
degradation
-
TcpB is acting as a quinone reductase for 6-chlorohydroxyquinone reduction during 2,4,6-trichlorophenol degradation, a toxic pollutant
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
analysis
-
method to measure enzyme inhibition in intact cells based on the resorufin reductase activity of enzyme. Values for 50% inhibition of enzyme by several reported in vivo inhibitors is at least three orders of magnitude higher for intact cells than for cell lysates
analysis
the enzyme is a catalyst for 1,4-dihydronicotinamide adenine dinucleotide-dependent amperometric biosensors and biofuel cells. For NADH detection, a linear range between 0.005 mM and 1 mM, a limit of detection of 0.003 mM, and a high sensitivity can be reached
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
design of novel lavendamycin analogues with enhanced, selective, and potent antitumor activity
drug development
-
ability of ketoconazole and itraconazole to induce NQO1 gene expression at the transcriptional level through an aryl hydrocarbon receptor-dependent mechanism
drug development
-
greater induction activities of the phase II enzyme quinone reductase associated with stilbenoids serve as a useful starting point for the design of improved chemopreventive agents
drug development
-
mild temperature heat shock elevates the NQO1 expression in cancer cells, which in turn markedly increases the sensitivity of the cells to the bioreductive drug beta-lapachone in vitro and in vivo
drug development
-
mild temperature heat shock elevates the NQO1 expression in cancer cells, which in turn markedly increases the sensitivity of the cells to the bioreductive drug beta-lapachone in vitro and in vivo
drug development
-
in vitro, almond skin polyphenols act as antioxidants and induce quinone reductase activity, but these actions are dependent upon their dose, method of extraction, and interaction with antioxidant vitamins
drug development
-
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
-
induction of phase 2 enzymes, e.g. NQO1 increases resistance to chemical carcinogenesis. Isothiocyanates can therefore be valuable chemopreventative agents, and the specificity of these substances toward the urinary bladder suggest that they may be particularly useful for protecting against bladder cancer
drug development
-
cytoprotective effect of bromocriptine involving PI3K- and Nrf2-mediated upregulation of the antioxidant enzyme NQO1, which may be a therapeutic strategy to protect cells from oxidative damage in Parkinson’s disease
drug development
-
the enzyme is a valuable target for activating stimuli-responsive drug delivery systems based on quinone derivatives, such as prodrugs and liposomes
drug development
-
mild temperature heat shock elevates the NQO1 expression in cancer cells, which in turn markedly increases the sensitivity of the cells to the bioreductive drug beta-lapachone in vitro and in vivo
-
medicine
-
antitumour quinones 2,5-diaziridinyl-3-hydroxymethyl-6-methyl-1,4-benzoquinone and 2,5-dimethyl-3,6-diaziridinyl-1,4-benzoquinone, i.e. RH1 and MeDZQ resp., induce apoptosis via enzyme-linked formation of alkylating species rather than via enzyme-linked redox cycling
medicine
-
ascorbic acid may potentiate the therapeutic efficacy of As3+ in treatment of acute promyelotic leukemia by enhancing the expression of enzyme together with heme oxygenase-1 and glutathione S-transferase Ya
medicine
-
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
-
enzyme is highly upregulated in active and chronic multiple sclerosis lesions, particularly in hypertrophic astrocytes and myelin-laden macrophages
medicine
-
statistically significant risk for colorectal cancer is associated with variant enzyme genotypes
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
-
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
-
clofibrate-mediated hepatoprotection against acetaminophen does not appear to be dependent upon enhanced expression of enzyme. Conditions of 94% inhobition of enzyme do not increase the susceptibility of hepatocytes from clofibrate treated mice to acetaminophen
medicine
-
enzyme 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
-
NQO1 polymorphism analysis is performed to investigate the relationship between prostate cancer and NQO1 C609T polymorphism in a turkish population, no correlation is found; 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
-
no association between NQO1 polymorphism and the risk of anthracycline-related congestive heart failure among childhood cancer survivors; 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 and SULT1A1 polymorphisms are associated with the risk of urothelial cancer, particularly among those who have ever smoked; 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
-
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
-
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
-
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; 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
-
acute manganese intoxication, similarly to that of cadmium and other heavy metals, increases both the hepatic level of Nrf2 and its transfer from the cytoplasm to the nucleus where it actively regulates the induction of phase II enzymes, e.g. NQO1
medicine
-
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
-
NQO1 gene polymorphism influences interleukin-6 levels and therefore attenuates the inflammatory response after cardiopulmonary bypass
medicine
-
neuroprotective role of DT-diaphorase against aminochrome neurotoxicity
medicine
-
strain difference where Sprague Dawley rats possess a sex-dependent expression and activity of Nqo1 and August Copenhagen x Irish rats exhibit no sexual dimorphism may provide an important tool when using these rat models for oxidative stress and cancer studies
medicine
-
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
-
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
-
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
-
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
-
3-nitrobenzanthrone is capable to induce NQO1 and CYP1A1 in lungs and kidney of rats thereby enhancing its own genotoxic and carcinogenic potential
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
-
plays a protective role against the induction of renal tumors by diethylstilbestrol
medicine
-
main function of QR1 is probably the detoxification of dietary quinones but it may also contribute to the reduction of vitamin K for its involvement in blood coagluation
medicine
-
main function of QR1 is probably the detoxification of dietary quinones but it may also contribute to the reduction of vitamin K for its involvement in blood coagluation
medicine
-
combination therapy employing a member of the group of non-cytotoxic NQO1 inhibitors together with a 2,6-dichlorophenolindophenol-like molecule may provide therapeutic efficacy against tumors that display high NQO1 enzymatic activity
medicine
-
isoform NQO1-KO mice exhibit a marked increase of permeability and spontaneous inflammation in the gut. In the dextran sulfate sodium salt-induced colitis model, NQO1-KO mice show more severe inflammatory responses than NQO1-wild-type mice. The transcript levels of claudin and occludin, the major tight junction molecules of gut epithelial cells, are significantly decreased in NQO1-KO mice. The colons of NQO1-KO mice also show high levels of reactive oxygen species and histone deacetylase activity
medicine
-
clofibrate-mediated hepatoprotection against acetaminophen does not appear to be dependent upon enhanced expression of enzyme. Conditions of 94% inhobition of enzyme do not increase the susceptibility of hepatocytes from clofibrate treated mice to acetaminophen
-
additional information
-
ERbeta and hPMC2 are required for trans-hydroxytamoxifen-dependent recruitment of coactivators such as PARP-1 to the electrophile response element of NQO1 resulting in the induction of the antioxidative enzyme and subsequent protection against oxidative DNA damage
additional information
-
PIFI is a novel component essential for NDH-mediated nonphotochemical reduction of the plastoquinone pool in chlororespiratory electron transport
additional information
-
WrbA bridges flavodoxins and oxidoreductases. WrbA shows a close relationship to mammalian Nqo1
additional information
-
oxidative stress-type cytotoxicity of chromate in FLK cells may be partly attributed to its reduction by NQO1, but not by glutathione reductase
Show AA Sequence (5378 entries)
Longer loading times are possible. Please use the Sequence Search for a specific query.
Longer loading times are possible. Please use the Sequence Search for a specific query.
LINKS TO OTHER DATABASES (specific for EC-Number 1.6.5.2)
html completed
Information
