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

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

EC NUMBER
COMMENTARY
1.6.5.2
-
RECOMMENDED NAME
GeneOntology No.
NAD(P)H dehydrogenase (quinone)
REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
NAD(P)H + H+ + a quinone = NAD(P)+ + a hydroquinone
show the reaction diagram
-
-
-
-
NAD(P)H + H+ + a quinone = NAD(P)+ + a hydroquinone
show the reaction diagram
ping-pong mechanism
-
NAD(P)H + H+ + a quinone = NAD(P)+ + a hydroquinone
show the reaction diagram
reaction mechanism
-
NAD(P)H + H+ + a quinone = NAD(P)+ + a hydroquinone
show the reaction diagram
ordered bi-bi mechanism
-
NAD(P)H + H+ + a quinone = NAD(P)+ + a hydroquinone
show the reaction diagram
ping-pong reaction mechanism
-
NAD(P)H + H+ + a quinone = NAD(P)+ + a hydroquinone
show the reaction diagram
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
show the reaction diagram
ping-pong mechanism with substrate inhibition
P39315
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
oxidation
-
-
-
-
oxidation
Q8CHK7
-
oxidation
-
-
oxidation
P05982
-
oxidation
Q07923
-
redox reaction
-
-
-
-
reduction
-
-
-
-
reduction
Q8CHK7
-
reduction
-
-
reduction
P05982
-
reduction
Q07923
-
PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
Biosynthesis of secondary metabolites
-
-
conversions
-
-
hydrogen production VIII
-
-
Ubiquinone and other terpenoid-quinone biosynthesis
-
-
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.
SYNONYMS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
azoreductase
-
-
-
-
azoreductase
Q8CHK7
-
azoreductase
Q64669
-
azoreductase
P05982
-
azoreductase
Q07923
-
chromate reductase
-
-
dehydrogenase, reduced nicotinamide adenine dinucleotide (phosphate, quinone)
-
-
-
-
diaphorase
-
-
-
-
DPNH-diaphorase
-
-
DT-diaphorase
-
-
-
-
DT-diaphorase
-
-
DT-diaphorase
P15559
-
DT-diaphorase
-
-
DT-diaphorase
-
-
DT-diaphorase
-
-
DTD
-
-
-
-
EC 1.6.99.2
P15559
formerly
EC 1.6.99.2
-
formerly
EC 1.6.99.2
-
formerly
EC 1.6.99.2
-
formerly
flavoprotein NAD(P)H-quinone reductase
-
-
-
-
FMN-dependent NAD(P)H:quinone oxidoreductase
-
-
Internal NADH dehydrogenase
-
-
MdaB
Helicobacter hepaticus ATCC51449
-
-
-
Menadione oxidoreductase
-
-
-
-
Menadione reductase
-
-
-
-
NAD(P)H dehydrogenase
-
-
-
-
NAD(P)H dehydrogenase complex
-
-
NAD(P)H menadione reductase
-
-
-
-
NAD(P)H quinone oxidoreductase
-
-
NAD(P)H quinone oxidoreductase-1
-
-
NAD(P)H quinone oxidoreductase-1
P15559
-
NAD(P)H quinone oxidoreductase1
-
-
NAD(P)H quinone reductase
-
-
NAD(P)H quinone reductase
Hevea brasiliensis Mull.-Arg.
-
-
-
NAD(P)H quinone-oxidoreductase 1
-
-
NAD(P)H-QR
-
-
NAD(P)H-QR
Hevea brasiliensis Mull.-Arg.
-
-
-
NAD(P)H-quinone dehydrogenase
-
-
-
-
NAD(P)H-quinone oxidoreductase
-
-
-
-
NAD(P)H-quinone oxidoreductase
-
-
NAD(P)H: (quinone acceptor) oxidoreductase
-
-
NAD(P)H: (quinone-acceptor)oxidoreductase
-
-
-
-
NAD(P)H: menadione oxidoreductase
-
-
-
-
NAD(P)H: Quinone oxidoreductase
-
-
NAD(P)H: Quinone oxidoreductase
Mus musculus C3H
-
-
-
NAD(P)H: quinone oxidoreductase 1
-
-
NAD(P)H: quinone oxidoreductase 1
-
-
NAD(P)H: quinone oxidoreductase-1
P15559
-
NAD(P)H: quinone reductase
-
-
NAD(P)H:quinone acceptor oxidoreductase
-
-
NAD(P)H:quinone oxidoreducatase 1
-
-
NAD(P)H:quinone oxidoreductase
-
-
NAD(P)H:quinone oxidoreductase
-
-
NAD(P)H:quinone oxidoreductase
P15559
-
NAD(P)H:quinone oxidoreductase
-
-
NAD(P)H:quinone oxidoreductase
-
-
NAD(P)H:quinone oxidoreductase 1
-
-
NAD(P)H:quinone oxidoreductase 1
-
-
NAD(P)H:quinone oxidoreductase 1
-
-
NAD(P)H:quinone oxidoreductase I
-
-
NAD(P)H:quinone oxidoreductase-1
-
-
NAD(P)H:quinone reductase
-
-
NAD(P)H:quinone reductase
-
-
NAD(P)H:quinoneoxidoreductase 1
-
-
NADH-menadione reductase
-
-
-
-
NADPH quinone reductase
-
-
NADPH quinone reductase
Helicobacter hepaticus ATCC51449
-
-
-
NADPH: quinone oxidoreductase-1
-
-
NADPH:quinone oxidoreductase
P15559
-
NADPH:quinone oxidoreductase
-
-
NADPH:quinone oxidoreductase 1
-
-
NADPH:quinone oxidoreductase 1
-
wild type NQO1, variant NQO1*2 induces an amino acid change P187S
NADPH:quinone oxidoreductase 1
-
QR
NADPH:quinone oxidoreductase 1
-
-
NAD[P]H:quinone acceptor oxidoreductase 1
-
-
Naphthoquinone reductase
-
-
-
-
Ndh complex
-
-
nicotinamide adenine dinucleotide phosphate:quinone oxidoreductase 1
-
-
NQO1
-
-
NQO1
-
; NQO1*2 gene
NQO1
P15559
-
NQO1
Mus musculus C3H
-
-
-
NQO1
-
-
NQO1
-
-
NRH:quinone reductase 1
P15559
-
p-Benzoquinone reductase
-
-
-
-
Phylloquinone reductase
-
-
-
-
QOR2
P39315
-
QR1
-
-
-
-
QR1
P15559
-
QR2
-
-
-
-
Quinone reductase
-
-
-
-
Quinone reductase
-
-
Quinone reductase
-
-
Quinone reductase
-
-
quinone reductase 1
-
-
quinone reductase 1
P15559
-
quinone reductase 1
-
-
Reduced NAD(P)H dehydrogenase
-
-
-
-
reduced nicotinamide-adenine dinucleotide (phosphate) dehydrogenase
-
-
-
-
TmQR2
Q5EI63
-
type II NADH: quinone oxidoreductase
-
-
Viologen accepting pyridine nucleotide oxidoreductase
-
-
-
-
Vitamin K reductase
-
-
-
-
Vitamin K reductase
-
-
vitamin-K reductase
-
-
-
-
WrbA
P0A8G6
-
WrbA
P15559
has NAD(P)H:quinone reductase activity
CAS REGISTRY NUMBER
COMMENTARY
9032-20-6
-
ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
ecotypes Col-0 and Col-gl1 wild-type, mutant line Salk_085656
-
-
Manually annotated by BRENDA team
tryptophan repressor-binding protein
SwissProt
Manually annotated by BRENDA team
tryptophan repressor-binding protein
SwissProt
Manually annotated by BRENDA team
amitochondriate eukaryote
-
-
Manually annotated by BRENDA team
strain ATCC51449
-
-
Manually annotated by BRENDA team
Helicobacter hepaticus ATCC51449
strain ATCC51449
-
-
Manually annotated by BRENDA team
Mll.-Arg.
-
-
Manually annotated by BRENDA team
Hevea brasiliensis Mull.-Arg.
Mll.-Arg.
-
-
Manually annotated by BRENDA team
; patients with congestive heart failure after anthracycline treatment during childhood
-
-
Manually annotated by BRENDA team
; patients with urothelial cancer in Taiwan
-
-
Manually annotated by BRENDA team
; prostatic adenocarcinoma patients
-
-
Manually annotated by BRENDA team
; recombinant protein
-
-
Manually annotated by BRENDA team
; recombinant protein and in human colon adenocarcinoma cells
SwissProt
Manually annotated by BRENDA team
breast cancer cell lines
-
-
Manually annotated by BRENDA team
breast cancer patients
-
-
Manually annotated by BRENDA team
comparison with quinone reductase 2
SwissProt
Manually annotated by BRENDA team
isoform NQO2
-
-
Manually annotated by BRENDA team
NAD(P)H:quinone acceptor oxidoreductase 2
-
-
Manually annotated by BRENDA team
patients with liver damage due to acetaminophen overdose or primary biliary cirrhosis
-
-
Manually annotated by BRENDA team
patients with multiple sclerosis
-
-
Manually annotated by BRENDA team
patients with sporadic colorectal cancer
-
-
Manually annotated by BRENDA team
recombiant isoform NQO1
-
-
Manually annotated by BRENDA team
recombinant enzyme
-
-
Manually annotated by BRENDA team
recombinant enzyme expressed in Chinese hamster ovary cells
-
-
Manually annotated by BRENDA team
recombinant enzyme, stably transfected to breast cancer cell line MDA468
-
-
Manually annotated by BRENDA team
simoidoscopy patients
-
-
Manually annotated by BRENDA team
2 forms have the same primary sequence
-
-
Manually annotated by BRENDA team
C3H mice
-
-
Manually annotated by BRENDA team
hydrophilic and hydrophobic isoform
-
-
Manually annotated by BRENDA team
isoform Nqo1
-
-
Manually annotated by BRENDA team
recombinant and native enzyme
-
-
Manually annotated by BRENDA team
strain CD-1
-
-
Manually annotated by BRENDA team
Mus musculus C3H
C3H mice
-
-
Manually annotated by BRENDA team
Mus musculus CD-1
strain CD-1
-
-
Manually annotated by BRENDA team
strain KT2440, gene chrR
-
-
Manually annotated by BRENDA team
3 to 4fold induction by 3-methylcholanthrene
-
-
Manually annotated by BRENDA team
female Sprague-Dawley rats
-
-
Manually annotated by BRENDA team
isoforms II, III, IV, V, VI and VII in liver
-
-
Manually annotated by BRENDA team
male Wistar rats
-
-
Manually annotated by BRENDA team
male, Wistar; male Wistar rats
-
-
Manually annotated by BRENDA team
Sprague Dawley and August Copenhagen x Irish strains
-
-
Manually annotated by BRENDA team
castor bean, enzymes DI and DII
-
-
Manually annotated by BRENDA team
Sporotrichum pulverulentum
-
-
-
Manually annotated by BRENDA team
Tinca vulgaris
-
-
-
Manually annotated by BRENDA team
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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
additional information
-
the homodimeric flavoprotein is unique among reductases, as it catalyzes the direct two-electron reduction of a wide variety quinones using NADH or NADPH as cofactor. Substrate docking studies, overview
SUBSTRATE
PRODUCT                      
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
LITERATURE
(Substrate)
COMMENTARY
(Product)
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
1,4-benzoquinone + NAD(P)+
1,4-benzoquinol + NAD(P)+
show the reaction diagram
P0A8G6
-
-
-
?
1,4-benzoquinone + NAD(P)+
1,4-benzoquinol + NAD(P)+
show the reaction diagram
P58795
-
-
-
?
1,4-benzoquinone + NADPH
1,4-benzoquinol + NADP+
show the reaction diagram
-
-
-
-
?
1,4-dimethoxymethylbenzoquinone + NAD(P)H
1,4-dimethoxymethylhydrobenzoquinone + NAD(P)+
show the reaction diagram
-
-
-
?
1,4-naphthoquinone + NAD(P)H
1,4-naphthohydroquinone + NAD(P)+
show the reaction diagram
-
-
-
?
1,4-naphthoquinone + NAD(P)H
1,4-naphthohydroquinone + NAD(P)+
show the reaction diagram
-
-
-
?
1,4-naphthoquinone + NAD(P)H
1,4-naphthohydroquinone + NAD(P)+
show the reaction diagram
-
-
-
?
1,4-naphthoquinone + NAD(P)H
1,4-naphthohydroquinone + NAD(P)+
show the reaction diagram
-
-
-
?
1,4-naphthoquinone + NAD(P)H
1,4-naphthohydroquinone + NAD(P)+
show the reaction diagram
P0A8G6
-
-
-
?
1,4-naphthoquinone + NAD(P)H
1,4-naphthohydroquinone + NAD(P)+
show the reaction diagram
P58795
-
-
-
?
1,4-naphthoquinone + NAD(P)H
1,4-naphthohydroquinone + NADP+
show the reaction diagram
Helicobacter hepaticus, Helicobacter hepaticus ATCC51449
-
-
-
-
?
1,4-naphthoquinone + NADPH
1,4-naphthoquinol + NADP+
show the reaction diagram
-
-
-
-
?
1,4-naphthoquinone + NADPH
1,4-naphthohydroquinol + NADP+
show the reaction diagram
-
-
-
-
?
1,4-naphthoquinone + NADPH
1,4-naphthoquinol
show the reaction diagram
-
-
-
-
?
1,4-tetramethylbenzoquinone + NAD(P)H
1,4-tetramethylhydrobenzoquinone + NAD(P)+
show the reaction diagram
-
-
-
?
1,8-dihydroxy-9,10-anthraquinone + NADPH
1,8-dihydroxy-9,10-anthraquinol + NADP+
show the reaction diagram
-
-
-
-
?
1-hydroxy-2-[2-(nitrooxy)ethyl]-1-oxo-2-(2,4,6-trinitro-3-(nitro[2-(nitrooxy)ethyl]amino)phenyl)diazanium + NAD(P)H + H+
reduced 1-hydroxy-2-[2-(nitrooxy)ethyl]-1-oxo-2-(2,4,6-trinitro-3-(nitro[2-(nitrooxy)ethyl]amino)phenyl)diazanium + NAD(P)+
show the reaction diagram
-
-
ratio kcat to Km value is 52000 per M and s
-
?
1-hydroxy-9,10-anthraquinone + NADPH
1-hydroxy-9,10-anthraquinol + NADP+
show the reaction diagram
-
-
-
-
?
17-(2-dimethylylamino)ethylamino-17-demethoxygeldanamycin + NAD(P)H + H+
reduced 17-(2-dimethylylamino)ethylamino-17-demethoxygeldanamycin + NADP+
show the reaction diagram
-
-
reduced component is a more potent Hsp90 inhibitor than parent benzoquinone ansamycin
-
?
17-(2-pyrrolidin-1-yl)ethylamino-17-demethoxygeldanamycin + NAD(P)H + H+
reduced 17-(2-pyrrolidin-1-yl)ethylamino-17-demethoxygeldanamycin + NADP+
show the reaction diagram
-
-
reduced component is a more potent Hsp90 inhibitor than parent benzoquinone ansamycin
-
?
17-allylamino-17-demethoxygeldanamycin + NAD(P)H + H+
reduced 17-allylamino-17-demethoxygeldanamycin + NADP+
show the reaction diagram
-
-
reduced component is a more potent Hsp90 inhibitor than parent benzoquinone ansamycin
-
?
17-amino-17-demethoxygeldanamycin + NAD(P)H + H+
reduced 17-amino-17-demethoxygeldanamycin + NADP+
show the reaction diagram
-
-
reduced component is a more potent Hsp90 inhibitor than parent benzoquinone ansamycin
-
?
2 ferricyanide + NAD(P)H
2 ferrocyanide + NAD(P)+ + H+
show the reaction diagram
Helicobacter hepaticus, Helicobacter hepaticus ATCC51449
-
-
-
-
?
2 ferricyanide + NADH
2 ferrocyanide + NAD+ + H+
show the reaction diagram
-
60% activity compared to the reactions of NADPH or NADH with 2,3-dimethoxy-5-methyl-1,4-benzoquinone
-
-
?
2,3,5,6-tetramethyl-1,4-benzoquinone + NAD(P)H
reduced 2,3,5,6-tetramethyl-1,4-benzoquinone + NAD(P)+
show the reaction diagram
-
-
-
-
?
2,3-diglutathionyl-1,4-naphthoquinone + NADPH
2,3-diglutathionyl-1,4-naphthoquinol + NADP+
show the reaction diagram
-
-
-
-
?
2,3-dihydroxy-5-methyl-1,4-benzoquinone + NAD(P)H
2,3-dihydroxy-5-methyl-1,4-benzoquinol + NAD(P)+
show the reaction diagram
P0A8G6
-
-
-
?
2,3-dihydroxy-5-methyl-1,4-benzoquinone + NAD(P)H
2,3-dihydroxy-5-methyl-1,4-benzoquinol + NAD(P)+
show the reaction diagram
P58795
-
-
-
?
2,3-dimethyl-1,4-naphthoquinone + NAD(P)H
2,3-dimethyl-1,4-hydronaphthoquinone + NAD(P)+
show the reaction diagram
-
-
-
?
2,4,6-trinitrotoluene + NAD(P)H +
reduced 2,4,6-trinitrotoluene + NAD(P)+
show the reaction diagram
-
-
ratio kcat to Km value is 670 per M and s
-
?
2,5-bis(aziridin-1-yl)-3,6-dimethylcyclohexa-2,5-diene-1,4-dione + NAD(P)H
2,5-bis(aziridin-1-yl)-3,6-dimethylbenzene-1,4-diol + NAD(P)+
show the reaction diagram
-
excellent substrate
-
-
?
2,5-bis(aziridin-1-yl)-3-(hydroxymethyl)-6-methylcyclohexane-1,4-dione + NAD(P)H
2,5-bis(aziridin-1-yl)-3-(hydroxymethyl)-6-methylbenzene-1,4-diol + NAD(P)+
show the reaction diagram
-
excellent substrate
-
-
?
2,5-bis(ethylamine)-3,6-diaziridinyl-1,4-benzoquinone + NADPH
2,5-bis(ethylamine)-3,6-diaziridinyl-1,4-benzoquinol + NADP+
show the reaction diagram
-
-
-
-
?
2,5-diaziridinyl-1,4-benzoquinone + NADPH
2,5-diaziridinyl-1,4-benzoquinol + NADP+
show the reaction diagram
-
-
-
-
?
2,5-diaziridinyl-3-(hydroxymethyl)-6-methyl-1,4-benzoquinone + NADPH
2,5-diaziridinyl-3-(hydroxymethyl)-6-methyl-1,4-benzoquinol + NADP+
show the reaction diagram
-
-
-
-
?
2,5-dihydroxy-1,4-naphthoquinone + NADPH
2,5-dihydroxy-1,4-naphthoquinol + NADP+
show the reaction diagram
-
-
-
-
?
2,5-dimethoxy-1,3-benzothiazole-4,7-dione + NAD(P)H
2,5-dimethoxy-1,3-benzothiazole-4,7-diol + NAD(P)+
show the reaction diagram
-
-
-
-
?
2,5-dimethoxy-1-methyl-1H-benzimidazole-4,7-dione + NAD(P)H
2,5-dimethoxy-1-methyl-1H-benzimidazole-4,7-diol + NAD(P)+
show the reaction diagram
-
-
-
-
?
2,5-dimethyl-1,4-benzoquinone + NADPH
2,5-dimethyl-1,4-benzoquinol + NADP+
show the reaction diagram
-
-
-
-
?
2,5-dimethyl-1,4-naphthoquinone + NADPH
2,5-dimethyl-1,4-naphthoquinol + NADP+
show the reaction diagram
-
-
-
-
?
2,5-dimethyl-3,6-diaziridinyl-1,4-benzoquinone + NADPH
2,5-dimethyl-3,6-diaziridinyl-1,4-benzoquinol + NADP+
show the reaction diagram
-
-
-
-
?
2,6-dimethoxybenzoquinone + NAD(P)H
2,6-dimethoxyhydrobenzoquinone + NAD(P)+
show the reaction diagram
-
-
-
?
2,6-dimethyl-1,4-benzoquinone + NADPH
2,6-dimethyl-1,4-benzoquinol + NADP+
show the reaction diagram
-
-
-
-
?
2-acetoxymethyl-6-methoxy-1-methylbenzimidazole-4,7-dione + NADH
? + NAD+
show the reaction diagram
-
-
-
-
?
2-chloro-6-hydroxy-1,4-benzoquinone + NADH
6-chlorobenzene-1,2,4-triol + NAD+
show the reaction diagram
-
-
-
-
?
2-ethyl-1,4-naphthoquinone + NAD(P)H
2-ethyl-1,4-hydronaphthoquinone + NAD(P)+
show the reaction diagram
-
-
-
?
2-hydroxy-1,4-naphthoquinone + NADPH
2-hydroxy-1,4-naphthoquinol + NADP+
show the reaction diagram
-
-
-
-
?
2-hydroxymethyl-5-methoxy-1-methylbenzimidazole-4,7-dione + NADH
? + NAD+
show the reaction diagram
-
-
-
-
?
2-hydroxymethyl-5-methoxy-2,5-cyclohexadiene-1,4-dione + NAD(P)H
2-hydroxymethyl-5-methoxy-2,5-cyclohexadiene-1,4-diol + NAD(P)+
show the reaction diagram
-
-
-
?
2-hydroxymethyl-5-methoxybenzothiazole-4,7-dione + NADH
? + NAD+
show the reaction diagram
-
-
-
-
?
2-hydroxymethyl-6-methoxy-1-methylbenzimidazole-4,7-dione + NADH
? + NAD+
show the reaction diagram
-
-
-
-
?
2-methoxy-2,5-cyclohexadiene-1,4-dione + NAD(P)H
2-methoxy-2,5-cyclohexadiene-1,4-diol + NAD(P)+
show the reaction diagram
-
-
-
?
2-methoxy-5-(methoxymethyl)-2,5-cyclohexadiene-1,4-dione + NAD(P)H
2-methoxy-5-methoxymethyl-2,5-cyclohexadiene-1,4-diol + NAD(P)+
show the reaction diagram
-
-
-
?
2-methoxyquinone + NAD(P)H
2-methoxyhydroquinone + NAD(P)+
show the reaction diagram
Sporotrichum pulverulentum
-
-
-
?
2-methyl-1,4-benzoquinone + NADPH
2-methyl-1,4-benzoquinol + NADP+
show the reaction diagram
-
-
-
-
?
2-methyl-1,4-naphthoquinone + NAD(P)H
2-methyl-1,4-naphthoquinol + NAD(P)+
show the reaction diagram
-
-
-
-
-
2-methyl-1,4-naphthoquinone + NAD(P)H
2-methyl-1,4-naphthoquinol + NAD(P)+
show the reaction diagram
-
-
-
?
2-methyl-1,4-naphthoquinone + NAD(P)H
2-methyl-1,4-naphthoquinol + NAD(P)+
show the reaction diagram
-
-
-
?
2-methyl-1,4-naphthoquinone + NAD(P)H
2-methyl-1,4-naphthoquinol + NAD(P)+
show the reaction diagram
-
-
-
?
2-methyl-1,4-naphthoquinone + NAD(P)H
2-methyl-1,4-naphthoquinol + NAD(P)+
show the reaction diagram
-
microsomal enzyme
-
-
2-methyl-1,4-naphthoquinone + NAD(P)H
2-methyl-1,4-naphthoquinol + NAD(P)+
show the reaction diagram
-
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)+
show the reaction diagram
-
artificial acceptor, trivial name menadione
-
?
2-methyl-1,4-naphthoquinone + NAD(P)H
2-methyl-1,4-naphthoquinol + NAD(P)+
show the reaction diagram
-
artificial acceptor, trivial name menadione
-
?
2-methyl-1,4-naphthoquinone + NAD(P)H
2-methyl-1,4-naphthoquinol + NAD(P)+
show the reaction diagram
-
artificial acceptor, trivial name menadione
-
?
2-methyl-1,4-naphthoquinone + NAD(P)H
2-methyl-1,4-naphthoquinol + NAD(P)+
show the reaction diagram
-
artificial acceptor, trivial name menadione
-
?
2-methyl-1,4-naphthoquinone + NAD(P)H
2-methyl-1,4-naphthoquinol + NAD(P)+
show the reaction diagram
-
artificial acceptor, trivial name menadione
-
?
2-methyl-1,4-naphthoquinone + NAD(P)H
2-methyl-1,4-naphthoquinol + NAD(P)+
show the reaction diagram
-
artificial acceptor, trivial name menadione
-
?
2-methyl-1,4-naphthoquinone + NAD(P)H
2-methyl-1,4-naphthoquinol + NAD(P)+
show the reaction diagram
-
artificial acceptor, trivial name menadione
-
?
2-methyl-1,4-naphthoquinone + NAD(P)H
2-methyl-1,4-naphthoquinol + NAD(P)+
show the reaction diagram
-
artificial acceptor, trivial name menadione
-
?
2-methyl-1,4-naphthoquinone + NAD(P)H
2-methyl-1,4-naphthoquinol + NAD(P)+
show the reaction diagram
-
artificial acceptor, trivial name menadione
-
?
2-methyl-1,4-naphthoquinone + NAD(P)H
2-methyl-1,4-dihydronaphthoquinone + NAD(P)+
show the reaction diagram
-
-
-
?
2-methyl-1,4-naphthoquinone + NADH
2-methyl-1,4-naphthoquinol + NAD+
show the reaction diagram
-
-
-
-
?
2-methyl-1,4-naphthoquinone + NADH
2-methyl-1,4-naphthoquinol + NAD+
show the reaction diagram
Hevea brasiliensis, Hevea brasiliensis Mull.-Arg.
-
-
-
-
?
2-methyl-1,4-naphthoquinone + NADPH
2-methyl-1,4-naphthoquinol + NADp+
show the reaction diagram
-
-
-
-
?
2-methyl-1,4-naphthoquinone + NADPH
2-methyl-1,4-naphthoquinol + NADp+
show the reaction diagram
-
-
-
-
?
2-methyl-1,4-naphthoquinone + NADPH
2-methyl-1,4-naphthoquinol + NADp+
show the reaction diagram
Hevea brasiliensis, Hevea brasiliensis Mull.-Arg.
-
-
-
-
?
2-methyl-3-glutathionyl-5-hydroxy-1,4-naphthoquinone + NADPH
2-methyl-3-glutathionyl-5-hydroxy-1,4-naphthoquinol + NADP+
show the reaction diagram
-
-
-
-
?
2-methyl-3-hydroxy-1,4-naphthoquinone + NADPH
2-methyl-3-hydroxy-1,4-naphthoquinol + NADP+
show the reaction diagram
-
-
-
-
?
2-methyl-3-phythyl-1,4-naphthoquinone + NAD(P)H
2-methyl-3-phythyl-1,4-naphthohydroquinone + NAD(P)+
show the reaction diagram
-
-
-
-
-
2-methyl-3-phythyl-1,4-naphthoquinone + NAD(P)H
2-methyl-3-phythyl-1,4-naphthohydroquinone + NAD(P)+
show the reaction diagram
-
trivial name vitamin K1
-
?
2-methyl-3-phythyl-1,4-naphthoquinone + NAD(P)H
2-methyl-3-phythyl-1,4-naphthohydroquinone + NAD(P)+
show the reaction diagram
-
trivial name vitamin K1
-
?
2-methyl-3-phythyl-1,4-naphthoquinone + NAD(P)H
2-methyl-3-phythyl-1,4-naphthohydroquinone + NAD(P)+
show the reaction diagram
-
trivial name vitamin K1, no activity with vitamin K1 diphosphate, menadione diphosphate, vitamin K1 oxide, d-alpha-tocopherol and d-alpha-tocoquinone
-
?
2-methyl-5-aziridinyl-1,4-benzoquinone + NADPH
2-methyl-5-aziridinyl-1,4-benzoquinol + NADP+
show the reaction diagram
-
-
-
-
?
2-methyl-5-hydroxy-1,4-naphthoquinone + NADPH
2-methyl-5-hydroxy-1,4-naphthoquinol + NADP+
show the reaction diagram
-
-
-
-
?
2-[nitro(2,4,6-trinitrophenyl)amino]ethyl nitrate + NAD(P)H +
reduced 2-[nitro(2,4,6-trinitrophenyl)amino]ethyl nitrate + NAD(P)+
show the reaction diagram
-
-
ratio kcat to Km value is 570000 per M and s
-
?
3,4-dihydro-2,2-dimethyl-2H-naphthol[1,2-b]pyran-5,6-dione + NAD(P)H
3,4-dihydro-2,2-dimethyl-2H-naphthol[1,2-b]pyran-5,6-diol + NAD(P)+
show the reaction diagram
-
trivial name beta-lapachone, potent cytotoxic agent against various cancer cell lines
-
?
3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide + NAD(P)H
reduced 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide + NAD(P)+
show the reaction diagram
-
-
-
-
?
3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide + NAD(P)H
reduced 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide + NAD(P)+
show the reaction diagram
-
-
-
?
3-(hydroxymethyl)-5-methoxy-1-methyl-2-phenyl-1H-indole-4,7-dione + NAD(P)H
3-(hydroxymethyl)-5-methoxy-1-methyl-2-phenyl-1H-indole-4,7-diol + NAD(P)+
show the reaction diagram
-
excellent substrate
-
-
?
4,5,6,7-tetranitro-1,3-dihydro-2H-benzimidazol-2-one + NAD(P)H +
reduced 4,5,6,7-tetranitro-1,3-dihydro-2H-benzimidazol-2-one + NAD(P)+
show the reaction diagram
-
-
ratio kcat to Km value is 5000000 per M and s
-
?
4,5,6-trinitro-1,3-dihydro-2H-benzimidazol-2-one + NAD(P)H +
reduced 4,5,6-trinitro-1,3-dihydro-2H-benzimidazol-2-one + NAD(P)+
show the reaction diagram
-
-
ratio kcat to Km value is 26000 per M and s
-
?
4,5-dimethoxy-3,5-cyclohexadiene-1,2-dione
4,5-dimethoxy-3,5-cyclohexadiene-1,2-diol + NAD(P)+
show the reaction diagram
-
-
-
?
5,8-dihydroxy-1,4-naphthoquinone + NADPH
5,8-dihydroxy-1,4-naphthoquinol + NADP+
show the reaction diagram
-
-
-
-
?
5,8-dihydroxynaphthoquinone + NAD(P)H
5,8-dihydroxynaphthohydroquinone + NAD(P)+
show the reaction diagram
-
-
-
?
5-(1-aziridinyl)-3-(hydroxymethyl)-2-(3-hydroxy-1-propenyl)-1-methyl-1H-indole-4,7-dione + NAD(P)H
5-(1-aziridinyl)-3-(hydroxymethyl)-2-(3-hydroxy-1-propenyl)-1-methyl-1H-indole-4,7-diol + NAD(P)+
show the reaction diagram
-
-
-
?
5-(aziridin-1-yl)-2,4-dinitrobenzamide + NAD(P)H
5-(aziridin-1-yl)-4-hydroxylamino-2-nitrobenzamide + NAD(P)+
show the reaction diagram
-
-
-
?
5-(aziridin-1-yl)-2,4-dinitrobenzamide + reduced dihydronicotineamide riboside
5-(aziridin-1-yl)-4-hydroxylamino-2-nitrobenzamide + oxidized dihydronicotineamide riboside
show the reaction diagram
-
-
-
?
5-aziridin-1-yl-2,4-dinitrobenzamide + NAD(P)H + H+
5-aziridin-1-yl-4-(hydroxyamino)-2-nitrobenzamide
show the reaction diagram
-
i.e. CB1954, anticancer prodrug
-
-
?
5-aziridin-1-yl-3-(hydroxymethyl)-2-[(1E)-3-hydroxyprop-1-en-1-yl]-1-methyl-1H-indole-4,7-dione + NAD(P)H
5-aziridin-1-yl-3-(hydroxymethyl)-2-[(1E)-3-hydroxyprop-1-en-1-yl]-1-methyl-1H-indole-4,7-diol + NAD(P)+
show the reaction diagram
-
-
-
-
?
5-hydroxy-1,4-naphthoquinone + NADPH
5-hydroxy-1,4-naphthoquinol + NADP+
show the reaction diagram
-
-
-
-
?
5-methoxy-1,2-dimethyl-3-(hydroxymethyl)indole-4,7-dione + NADH
? + NAD+
show the reaction diagram
-
is efficiently metabolized by NQO1
-
-
?
5-methoxy-1,2-dimethyl-3-[(phenoxy)methyl]indole-4,7-dione + NADH
? + NAD+
show the reaction diagram
-
inefficient indolequinone substrate
-
-
?
5-methoxy-2-methylbenzothiazole-4,7-dione + NADH
? + NAD+
show the reaction diagram
-
-
-
-
?
6-hydroxydopaminequinone + NAD(P)H
6-hydroxydopaminehydroquinone + NAD(P)+
show the reaction diagram
-
-
-
?
6-hydroxydopaquinone + NAD(P)H
6-hydroxydopahydroquinone + NAD(P)+
show the reaction diagram
-
-
-
?
6-methoxy-1,2-dimethyl-3-(hydroxymethyl)indole-4,7-dione + NADH
? + NAD+
show the reaction diagram
-
is efficiently metabolized by NQO1
-
-
?
6-methoxy-1,2-dimethyl-3-[(phenoxy)methyl]indole-4,7-dione + NADH
? + NAD+
show the reaction diagram
-
inefficient indolequinone substrate
-
-
?
6-methoxy-1-methyl-2-(4-nitrophenoxymethyl)benzimidazole-4,7-dione + NADH
? + NAD+
show the reaction diagram
-
-
-
-
?
6-methoxy-1-methylbenzimidazole-4,7-dione + NADH
? + NAD+
show the reaction diagram
-
-
-
-
?
7-N-(2-furoyl)demethyllavendamycin methyl ester + NADH
? + NAD+
show the reaction diagram
P15559
poor substrate
-
-
?
7-N-acetyldemethyllavendamycin n-butyl amide + NADH
? + NAD+
show the reaction diagram
P15559
good substrate
-
-
?
7-N-acetyldemethyllavendamycin sec-butyl amide + NADH
? + NAD+
show the reaction diagram
P15559
poor substrate
-
-
?
9,10-anthraquinone-2,6-disulfonate + NADPH
? + NADP+
show the reaction diagram
-
-
-
-
?
9,10-anthraquinone-2-sulfonate + NADPH
? + NADP+
show the reaction diagram
-
-
-
-
?
9,10-phenanthrene quinone + NADPH
9,10-phenanthrene quinol + NADP+
show the reaction diagram
-
-
-
-
?
acetaminophen + NAD(P)H + H+
N-acetyl-p-benzoquinone imine + NAD(P)+
show the reaction diagram
-
-
enhanced levels of hepatic enzyme may detoxify N-acetyl-p-benzoquinone imine by reducing it back to acetaminophen
-
r
alpha-tocopherolquinone + NAD(P)H
reduced alpha-tocopherolquinone + NAD(P)+
show the reaction diagram
-
-
-
-
?
benzoquinone + NAD(P)+
benzohydroquinone + NAD(P)+
show the reaction diagram
-
-
-
?
benzoquinone + NAD(P)+
benzohydroquinone + NAD(P)+
show the reaction diagram
-
-
-
?
benzoquinone + NAD(P)+
benzohydroquinone + NAD(P)+
show the reaction diagram
-
-
-
?
benzoquinone + NAD(P)+
benzohydroquinone + NAD(P)+
show the reaction diagram
-
no activity with coenzyme Q6 and vitamin K1
-
?
benzoquinone + NAD(P)+
benzohydroquinone + NAD(P)+
show the reaction diagram
-
no reaction with p-benzoquinone
-
-
?
benzoquinone + NADH
?
show the reaction diagram
-
-
-
-
?
benzo[a]pyrene 3,6-quinone + NAD(P)H
benzo[a]pyrene 3,6-quinol
show the reaction diagram
-
-
-
?
beta-lapachone + NAD(P)H
reduced beta-lapachone + NAD(P)+
show the reaction diagram
-
-
-
-
?
chromate(IV) + H2O
chromate(III) + H2O2
show the reaction diagram
-
-
-
-
?
chromate(VI) + H2O
chromate(III) + H2O2
show the reaction diagram
-
-
-
-
?
chromate(VI) + H2O
chromate(III) + H2O2
show the reaction diagram
-
extremely poor substrate
-
-
?
coenzyme Q0 + NAD(P)H
reduced coenzyme Q0 + NADP+
show the reaction diagram
Helicobacter hepaticus, Helicobacter hepaticus ATCC51449
-
-
-
-
?
coenzyme Q1 + NAD(P)H
reduced coenzyme Q1 + NADP+
show the reaction diagram
Helicobacter hepaticus, Helicobacter hepaticus ATCC51449
-
-
-
-
?
coenzyme Q1 + NADH
?
show the reaction diagram
-
-
-
-
?
coenzyme Q10 + NAD(P)H
reduced coenzyme Q10 + NAD(P)+
show the reaction diagram
-
-
-
?
cyclized-dopamine o-quinone + NAD(P)H
cyclized-dopamine o-hydroquinone + NADP+
show the reaction diagram
-
-
-
?
cytochrome C + menadione + NADH
? + reduced menadione + NAD+
show the reaction diagram
-
-
-
-
?
deamino-NADH + H+ + 2,3-dimethoxy-5-methyl-1,4-benzoquinone
deamino-NAD+ + 2,3-dimethoxy-5-methyl-1,4-benzoquinol
show the reaction diagram
-
45% activity compared to NADPH or NADH
-
-
?
diethyl [2,5-bis(aziridin-1-yl)-3,6-dioxocyclohexa-1,4-diene-1,4-diyl]biscarbamate + NAD(P)H
diethyl [2,5-bis(aziridin-1-yl)-3,6-dihydroxybenzene-1,4-diyl]biscarbamate + NAD(P)+
show the reaction diagram
-
-
-
-
?
duroquinone + NAD(P)H
reduced duroquinone + NAD(P)+
show the reaction diagram
-
-
-
-
?
duroquinone + NADH
? + NAD+
show the reaction diagram
Hevea brasiliensis, Hevea brasiliensis Mull.-Arg.
-
-
-
-
?
duroquinone + NADH
?
show the reaction diagram
-
-
-
-
?
duroquinone + NADPH
? + NADP+
show the reaction diagram
Hevea brasiliensis, Hevea brasiliensis Mull.-Arg.
-
-
-
-
?
duroquinone + NADPH
durohydroquinone + NADP+
show the reaction diagram
-
in both normoxic and hyperoxia-exposed cells, enzyme is the dominant duroquinone reductase
-
-
?
ethyl 5-aziridin-1-yl-2,4-dinitrobenzoate + NAD(P)H +
reduced ethyl 5-aziridin-1-yl-2,4-dinitrobenzoate + NAD(P)+
show the reaction diagram
-
-
ratio kcat to Km value is 20000 per M and s
-
?
FAD + NADH
?
show the reaction diagram
-
-
-
-
?
ferricyanide + FAD + NADH
?
show the reaction diagram
-
-
-
-
?
ferricyanide + FMN + NADH
?
show the reaction diagram
-
-
-
-
?
FMN + NADH
?
show the reaction diagram
-
-
-
-
?
geldanamycin + NAD(P)H
reduced geldanamycin + NAD(P)+
show the reaction diagram
-
excellent substrate
-
-
?
geldanamycin + NAD(P)H + H+
reduced geldanamycin + NADP+
show the reaction diagram
-
-
reduced component is a more potent Hsp90 inhibitor than parent benzoquinone ansamycin
-
?
hydroxy(oxo)(3,6,8-trinitro-9H-carbazol-1-yl)ammonium + NAD(P)H +
reduced 2-[nitro(2,4,6-trinitrophenyl)amino]ethyl nitrate + NAD(P)+
show the reaction diagram
-
-
ratio kcat to Km value is 500000 per M and s
-
?
indolequinones + NAD(P)H
indolehydroquinones + NAD(P)+
show the reaction diagram
-
compounds with electron-withdrawing groups at the indole 3-position are among the best substrates, groups larger than methyl at N-1 are tolerated, compounds with a leaving group at the 3-indolyl methyl position inactivate the enzyme
-
?
juglone + NAD(P)H
dihydrojuglone + NAD(P)+
show the reaction diagram
-
-
-
?
juglone + NAD(P)H
dihydrojuglone + NAD(P)+
show the reaction diagram
-
-
-
?
juglone + NADH
dihydrojuglone + NAD+
show the reaction diagram
Hevea brasiliensis, Hevea brasiliensis Mull.-Arg.
-
-
-
-
?
juglone + NADPH
dihydrojuglone + NADP+
show the reaction diagram
-
-
-
-
?
K3[Fe(CN)6] + NAD(P)H
K4[Fe(CN)6] + NAD(P)+
show the reaction diagram
-
-
-
?
K3[Fe(CN)6] + NAD(P)H
K4[Fe(CN)6] + NAD(P)+
show the reaction diagram
-
-
-
?
K3[Fe(CN)6] + NAD(P)H
K4[Fe(CN)6] + NAD(P)+
show the reaction diagram
-
no activity with coenzyme Q10
-
?
K3[Fe(CN)6] + NAD(P)H
K4[Fe(CN)6] + NAD(P)+
show the reaction diagram
-
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)+
show the reaction diagram
-
no activity with lipoic acid, cytochrome c and vitamin K1
-
?
K3[Fe(CN)6] + NAD(P)H
K4[Fe(CN)6] + NAD(P)+
show the reaction diagram
-
no activity with lipoic acid, cytochrome c and vitamin K1
-
?
K3[Fe(CN)6] + NAD(P)H
K4[Fe(CN)6] + NAD(P)+
show the reaction diagram
-
no activity with lipoic acid, cytochrome c and vitamin K1
-
?
lavendamycin beta-hydroxyethyl ester + NADH
? + NAD+
show the reaction diagram
P15559
good substrate
-
-
?
menadione + FAD + NADH
?
show the reaction diagram
-
-
-
-
?
menadione + FMN + NADH
?
show the reaction diagram
-
-
-
-
?
menadione + NAD(P)H
reduced menadione + NAD(P)+
show the reaction diagram
P0A8G6
-
-
-
?
menadione + NAD(P)H
reduced menadione + NAD(P)+
show the reaction diagram
P58795
-
-
-
?
menadione + NAD(P)H
reduced menadione + NADP+
show the reaction diagram
-
-
-
-
?
menadione + NADH
?
show the reaction diagram
-
-
-
-
?
menadione + NADH
reduced menadione + NAD+
show the reaction diagram
-
-
-
-
?
menadione + NADH
reduced menadione + NAD+
show the reaction diagram
-
-
-
-
?
menadione + NADH + H+
? + NAD+
show the reaction diagram
Q5EI63
-
-
-
?
menadione + NADPH
reduced menadione + NADP+
show the reaction diagram
-
-
-
-
?
menadione + NADPH + H+
? + NADP+
show the reaction diagram
Q5EI63
-
-
-
?
menadione + reduced nicotinamide 2-azidoadenine dinucleotide
reduced menadione + oxidized nicotinamide 2-azidoadenine dinucleotide
show the reaction diagram
-
-
-
?
menadione + reduced nicotinamide 8-azidoadenine dinucleotide
reduced menadione + oxidized nicotinamide 8-azidoadenine dinucleotide
show the reaction diagram
-
-
-
?
methoxyquinone + NAD(P)H
methoxyhydroquinone + NAD(P)+
show the reaction diagram
Sporotrichum pulverulentum
-
-
-
?
methyl red + NAD(P)H
reduced methyl red + NAD(P)+
show the reaction diagram
-
-
-
-
-
methyl red + NAD(P)H
reduced methyl red + NAD(P)+
show the reaction diagram
-
-
-
?
methyl-1,4-benzoquinone + NADPH + H+
methyl-1,4-benzoquinol + NADP+
show the reaction diagram
P39315
two-electron mechanism
-
-
?
methylene blue + NAD(P)H
reduced methylene blue + NAD(P)+
show the reaction diagram
-
-
-
?
mitomycin C + NAD(P)H
reduced mitomycin C + NAD(P)+
show the reaction diagram
-
poor substrate
-
-
?
N-methyl-N,2,4,6-tetranitroaniline + NAD(P)H +
reduced N-methyl-N,2,4,6-tetranitroaniline + NAD(P)+
show the reaction diagram
-
-
ratio kcat to Km value is 260000 per M and s
-
?
N-methyl-N,2,4-trinitroaniline + NAD(P)H +
reduced N-methyl-N,2,4-trinitroaniline + NAD(P)+
show the reaction diagram
-
-
ratio kcat to Km value is 52000 per M and s
-
?
NAD(P)H + H+ + 17-allylamino-demethoxygeldanamycin
NAD(P)+ + reduced 17-allylamino-demethoxygeldanamycin
show the reaction diagram
-
-
product exhibits superior Hsp90 inhibition and is involved in Hsp70 induction and Raf-1 degradation
-
?
NAD(P)H + H+ + 2,5-diaziridinyl-3-hydroxymethyl-6-methyl-1,4-benzoquinone
NAD(P)+ + reduced 2,5-diaziridinyl-3-hydroxymethyl-6-methyl-1,4-benzoquinone
show the reaction diagram
-
i.e. RH1, induction of apoptosis via enzyme-linked formation of alkylating species
-
-
?
NAD(P)H + H+ + 2,5-dimethyl-3,6-diaziridinyl-1,4-benzoquinone
NAD(P)+ + reduced 2,5-dimethyl-3,6-diaziridinyl-1,4-benzoquinone
show the reaction diagram
-
i.e. MeDZQ, induction of apoptosis via enzyme-linked formation of alkylating species
-
-
?
NAD(P)H + H+ + a quinone
NAD(P)+ + a hydroquinone
show the reaction diagram
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
-
-
?
NAD(P)H + H+ + oxidized 2,6-dichlorophenolindophenol
NAD(P)+ + reduced 2,6-dichlorophenolindophenol
show the reaction diagram
-
-
-
?
NAD(P)H + H+ + oxidized 2,6-dichlorophenolindophenol
NAD(P)+ + reduced 2,6-dichlorophenolindophenol
show the reaction diagram
-
-
-
-
?
NAD(P)H + H+ + oxidized 2,6-dichlorophenolindophenol
NAD(P)+ + reduced 2,6-dichlorophenolindophenol
show the reaction diagram
-
-
-
?
NAD(P)H + H+ + oxidized 2,6-dichlorophenolindophenol
NAD(P)+ + reduced 2,6-dichlorophenolindophenol
show the reaction diagram
-
-
-
?
NAD(P)H + H+ + oxidized 2,6-dichlorophenolindophenol
NAD(P)+ + reduced 2,6-dichlorophenolindophenol
show the reaction diagram
-
-
-
?
NAD(P)H + H+ + oxidized 2,6-dichlorophenolindophenol
NAD(P)+ + reduced 2,6-dichlorophenolindophenol
show the reaction diagram
-
-
-
-
?
NAD(P)H + H+ + oxidized 2,6-dichlorophenolindophenol
NAD(P)+ + reduced 2,6-dichlorophenolindophenol
show the reaction diagram
-
-
-
?
NAD(P)H + H+ + oxidized 2,6-dichlorophenolindophenol
NAD(P)+ + reduced 2,6-dichlorophenolindophenol
show the reaction diagram
-
-
-
?
NAD(P)H + H+ + oxidized 2,6-dichlorophenolindophenol
NAD(P)+ + reduced 2,6-dichlorophenolindophenol
show the reaction diagram
-
-
-
?
NAD(P)H + H+ + oxidized 2,6-dichlorophenolindophenol
NAD(P)+ + reduced 2,6-dichlorophenolindophenol
show the reaction diagram
-
-
-
?
NAD(P)H + H+ + oxidized 2,6-dichlorophenolindophenol
NAD(P)+ + reduced 2,6-dichlorophenolindophenol
show the reaction diagram
-
-
-
-
?
NAD(P)H + H+ + oxidized 2,6-dichlorophenolindophenol
NAD(P)+ + reduced 2,6-dichlorophenolindophenol
show the reaction diagram
P0A8G6
-
-
-
?
NAD(P)H + H+ + oxidized 2,6-dichlorophenolindophenol
NAD(P)+ + reduced 2,6-dichlorophenolindophenol
show the reaction diagram
P58795
-
-
-
?
NAD(P)H + H+ + oxidized 2,6-dichlorophenolindophenol
NAD(P)+ + reduced 2,6-dichlorophenolindophenol
show the reaction diagram
-
low activity
-
?
NAD(P)H + H+ + oxidized 2,6-dichlorophenolindophenol
NAD(P)+ + reduced 2,6-dichlorophenolindophenol
show the reaction diagram
-
low activity
-
?
NAD(P)H + H+ + oxidized 2,6-dichlorophenolindophenol
NAD(P)+ + reduced 2,6-dichlorophenolindophenol
show the reaction diagram
-
microsomal enzyme
-
-
NAD(P)H + H+ + quinone
NAD(P)+ + hydroquinone
show the reaction diagram
-
-
-
-
?
NADH + decylubiquinone
NAD+ + decylubiquinol
show the reaction diagram
-
-
-
-
?
NADH + H+ + 1-[3,5-dinitro-2-(1,2,3,4-tetrahydronaphthalen-2-yl)phenyl]-1-oxohydrazinium
?
show the reaction diagram
-
-
-
-
?
NADH + H+ + 10-nitro-5,6-dihydrobenzimidazo[2,1-a]isoquinoline 12-oxide
?
show the reaction diagram
-
-
-
-
?
NADH + H+ + 10-nitro-5,6-dihydrobenzimidazo[2,1-a]isoquinoline-8-carboxamide 12-oxide
?
show the reaction diagram
-
-
-
-
?
NADH + H+ + 10-nitro-5,6-dihydrobenzimidazo[2,1-a]isoquinoline-9-carboxamide 12-oxide
?
show the reaction diagram
-
-
-
-
?
NADH + H+ + 17-(allylamino)-17-demethoxygeldanamycin
?
show the reaction diagram
-
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, NAD(P)H:quinone oxidoreductase 1 metabolizes the heat shock protein 90 inhibitor 17-(allylamino)-17-demethoxygeldanamycin to the corresponding hydroquinone
-
-
?
NADH + H+ + 2,10-dinitro-5,6-dihydrobenzimidazo[2,1-a]isoquinoline 12-oxide
?
show the reaction diagram
-
-
-
-
?
NADH + H+ + 2,3-dimethoxy-5-methyl-1,4-benzoquinone
NAD+ + 2,3-dimethoxy-5-methyl-1,4-benzoquinol
show the reaction diagram
-
-
-
-
?
NADH + H+ + 2,4-dinitro-5-(1,2,3,4-tetrahydronaphthalen-2-yl)benzamide
?
show the reaction diagram
-
-
-
-
?
NADH + H+ + 2,4-dinitro-5-(5-nitro-1,2,3,4-tetrahydronaphthalen-2-yl)benzamide
?
show the reaction diagram
-
-
-
-
?
NADH + H+ + 2,4-dinitro-5-(7-nitro-1,2,3,4-tetrahydronaphthalen-2-yl)benzamide
?
show the reaction diagram
-
-
-
-
?
NADH + H+ + 2-(2,4,6-trinitrophenyl)-1,2,3,4-tetrahydronaphthalene
?
show the reaction diagram
-
-
-
-
?
NADH + H+ + 2-(2,4-dinitrophenyl)-1,2,3,4-tetrahydronaphthalene
?
show the reaction diagram
-
-
-
-
?
NADH + H+ + 2-(2,4-dinitrophenyl)-5-nitro-1,2,3,4-tetrahydronaphthalene
?
show the reaction diagram
-
-
-
-
?
NADH + H+ + 2-(3,5-dinitropyridin-2-yl)-1,2,3,4-tetrahydroisoquinoline
?
show the reaction diagram
-
-
-
-
?
NADH + H+ + 2-methyl-1,4-naphthoquinone
NAD+ + 2-methyl-1,4-naphthoquinol
show the reaction diagram
-
-
-
-
?
NADH + H+ + 2-[2,4-dinitro-6-(trifluoromethyl)phenyl]-1,2,3,4-tetrahydronaphthalene
?
show the reaction diagram
-
-
-
-
?
NADH + H+ + 2-[2,4-dinitro-6-(trifluoromethyl)phenyl]-5-nitro-1,2,3,4-tetrahydronaphthalene
?
show the reaction diagram
-
-
-
-
?
NADH + H+ + 2-[2,4-dinitro-6-(trifluoromethyl)phenyl]-7-nitro-1,2,3,4-tetrahydronaphthalene
?
show the reaction diagram
-
-
-
-
?
NADH + H+ + 3,5-dinitro-2-(1,2,3,4-tetrahydronaphthalen-2-yl)benzamide
?
show the reaction diagram
-
-
-
-
?
NADH + H+ + 3,5-dinitro-2-(1,2,3,4-tetrahydronaphthalen-2-yl)benzoic acid
?
show the reaction diagram
-
-
-
-
?
NADH + H+ + 3,5-dinitro-2-(7-nitro-1,2,3,4-tetrahydronaphthalen-2-yl)benzoic acid
?
show the reaction diagram
-
-
-
-
?
NADH + H+ + 4,10-dinitro-5,6-dihydrobenzimidazo[2,1-a]isoquinoline 12-oxide
?
show the reaction diagram
-
-
-
-
?
NADH + H+ + 4,10-dinitro-5,6-dihydrobenzimidazo[2,1-a]isoquinoline-9-carboxamide 12-oxide
?
show the reaction diagram
-
-
-
-
?
NADH + H+ + 4,10-dinitro-8-(trifluoromethyl)-5,6-dihydrobenzimidazo[2,1-a]isoquinoline 12-oxide
?
show the reaction diagram
-
-
-
-
?
NADH + H+ + 5,6-dihydro-10-nitropyrido[3'',2'':4',5']imidazo[2',1'-a]isoquinoline 12-oxide
?
show the reaction diagram
-
-
-
-
?
NADH + H+ + 5-(aziridin-1-yl)-2,4-dinitrobenzamide
?
show the reaction diagram
-
i.e. CB-1954
-
-
?
NADH + H+ + a quinone
NAD+ + a hydroquinone
show the reaction diagram
-
-
-
-
?
NADH + H+ + atovaquone
NAD+ + reduced atovaquone
show the reaction diagram
-
atovaquone is 2-[4-(4-chlorophenyl)cyclohexyl]-3-hydroxynaphthalene-1,4-dione
-
-
?
NADH + H+ + benzoquinone
NAD+ + benzoquinol
show the reaction diagram
-
-
-
-
?
NADH + H+ + coenzyme Q0
NAD+ + reduced coenzyme Q0
show the reaction diagram
-
-
-
-
?
NADH + H+ + coenzyme Q1
NAD+ + reduced coenzyme Q1
show the reaction diagram
-
-
-
-
?
NADH + H+ + dichlorophenolindophenol
NAD+ + reduced dichlorophenolindophenol
show the reaction diagram
-
-
-
-
?
NADH + H+ + durooquinone
NAD+ + durooquinol
show the reaction diagram
-
-
-
-
?
NADH + H+ + ubiquinone
NAD+ + ubiquinone
show the reaction diagram
-
the enzyme plays an essential role in maintaining a reduced ubiquinone-pool during infection (Plasmodium falciparum is the causative agents of malaria). The enzyme is not only essential to parasite survival in vivo but may also contribute to the severity and outcome of disease. Type II NADH:quinone oxidoreductase the membrane-bound respiratory enzyme differs from the canonical NADH:dehydrogenase (complex I), because it is not involved in the vectorial transfer of protons across membranes. In the electron transport chain of Plasmodium, the canonical multimeric complex I (NADH:dehydrogenase) found in mammalian mitochondria is absent, and, instead, the parasite possesses five quinone-dependent oxidoreductases, namely a type II NADH:quinone oxidoreductase (PfNDH2), a malate: quinone oxidoreductase (MQO), a dihydroorotate dehydrogenase (DHOD), a glycerol-3-phosphate dehydrogenase (G3PDH), and a succinate: quinone oxidoreductase (SDH). These enzymes link cytosolic metabolism to mitochondrial metabolism, generating reducing power (ubiquinol) for the bc1 complex and an aa3-type cytochrome oxidase, enabling proton pumping and energy conservation
-
-
?
NADH + H+ + ubiquinone-0
NAD+ + ubiquinol-0
show the reaction diagram
-
-
-
-
?
NADH + H+ + ubiquinone-1
NAD+ + ubiquinol-1
show the reaction diagram
-
-
-
-
?
NADH + H+ + ubiquinone-10
NAD+ + ubiquinol-10
show the reaction diagram
-
-
-
-
?
NADPH + H+ + 17-(allylamino)-17-demethoxygeldanamycin
?
show the reaction diagram
-
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, NAD(P)H:quinone oxidoreductase 1 metabolizes the heat shock protein 90 inhibitor 17-(allylamino)-17-demethoxygeldanamycin to the corresponding hydroquinone
-
-
?
NADPH + H+ + 2,3-dimethoxy-5-methyl-1,4-benzoquinone
NADP+ + 2,3-dimethoxy-5-methyl-1,4-benzoquinol
show the reaction diagram
-
100% activity
-
-
?
NADPH + H+ + 2-methyl-1,4-naphthoquinone
NADP+ + 2-methyl-1,4-naphthoquinol
show the reaction diagram
-
-
-
-
?
NADPH + H+ + a quinone
NADP+ + a hydroquinone
show the reaction diagram
-
-
-
-
?
NADPH + H+ + benzoquinone
NADP+ + benzoquinol
show the reaction diagram
-
-
-
-
?
NADPH + H+ + durooquinone
NADP+ + durooquinol
show the reaction diagram
-
-
-
-
?
NADPH + H+ + oxidized 2,6-dichlorophenolindophenol
NADP+ + reduced 2,6-dichlorophenolindophenol
show the reaction diagram
-
-
-
-
?
NADPH + H+ + oxidized 2,6-dichlorophenolindophenol
NADP+ + reduced 2,6-dichlorophenolindophenol
show the reaction diagram
-
-
-
-
?
NADPH + H+ + quinone
NADP+ + ?
show the reaction diagram
-
-
-
-
?
NADPH + H+ + quinone
NADP+ + ?
show the reaction diagram
-
TNF alpha and LPS induce Nqo1 mRNA expression
-
-
?
NADPH + H+ + ubiquinone-1
NADP+ + ubiquinol-1
show the reaction diagram
-
-
-
-
?
NADPH + H+ + ubiquinone-10
NADP+ + ubiquinol-10
show the reaction diagram
-
-
-
-
?
nitracrine + NAD(P)H +
reduced nitracrine + NAD(P)+
show the reaction diagram
-
-
i.e. N,N-dimethyl-N'-(1-nitro-9,10-dihydroacridin-9-yl)propane-1,3-diamine, ratio kcat to Km value is 1800 per M and s
-
?
oxidized dichlorophenol-indophenol + NAD(P)H
reduced dichlorophenol-indophenol + NADP+
show the reaction diagram
Helicobacter hepaticus, Helicobacter hepaticus ATCC51449
-
-
-
-
?
p-benzoquinone + NADH
benzohydroquinone + NAD+
show the reaction diagram
-
-
-
-
?
p-benzoquinone + NADPH
p-benzohydroquinone + NADP+
show the reaction diagram
-
-
-
-
?
plumbagin + NADH
? + NAD+
show the reaction diagram
-
-
-
-
?
plumbagin + NADPH
? + NADP+
show the reaction diagram
-
-
-
-
?
quinone + NAD(P)H
hydroquinone + NAD(P)+
show the reaction diagram
-
possible role in seed germination
-
?
quinone + NAD(P)H
hydroquinone + NAD(P)+
show the reaction diagram
-
protection of cells against damage by reactive oxygen species generated during oxidative cycling of quinones and semiquinone radicals
-
?
riboflavin + NADPH
? + NADP+
show the reaction diagram
-
-
-
-
?
streptonigrin + NAD(P)H
reduced streptonigrin + NAD(P)+
show the reaction diagram
-
one of the best substrates for NQO1
-
-
?
tetramethyl-1,4-benzoquinone + NADPH
tetramethyl-1,4-benzoquinol + NADP+
show the reaction diagram
-
-
-
-
?
toluquinone + NAD(P)H
toluhydroquinone + NAD(P)+
show the reaction diagram
Sporotrichum pulverulentum
-
-
-
?
ubiquinone + NAD(P)H
reduced ubiquinone + NAD(P)+
show the reaction diagram
-
-
-
-
?
ubiquinone-1 + NADPH + H+
ubiquinol-1 + NADP+
show the reaction diagram
-
the protein shows NADH-ubiquinone-1 oxidoreductase activity (EC 1.6.5.3), NADPH oxidase (EC 1.6.3.1) and NADPH-ubiquinone-1 oxidoreductase (EC 1.6.5.2) activities
-
-
?
vitamin K + NAD(P)H
reduced vitamin K + NAD(P)+
show the reaction diagram
-
-
-
?
vitamin K2 + NAD(P)H
reduced vitamin K2 + NAD(P)+
show the reaction diagram
-
-
-
?
[Fe(CN)6]3- + NAD(P)H
[Fe(CN)6]4- + NAD(P)+
show the reaction diagram
P0A8G6
-
-
-
?
[Fe(CN)6]3- + NAD(P)H
[Fe(CN)6]4- + NAD(P)+
show the reaction diagram
P58795
-
-
-
?
mitomycin C + NADPH
? + NADP+
show the reaction diagram
-
-
-
-
?
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
?
-
-
NQO1 activity colocalizes closely with Alzheimers disease pathology supporting a presumed role as an antioxidant system upregulated in response to the oxidative stress of the Alzheimers disease process
-
-
-
additional information
?
-
-
plays one of the main roles in the bioactivation of quinoidal drugs
-
-
-
additional information
?
-
-
regeneration of alpha-tocopherol may be one of the physiologic functions of this enzyme
-
-
-
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
?
-
-
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
?
-
P0A8G6
role of enzyme in protecting against environmental stressors
-
-
-
additional information
?
-
P58795
role of enzyme in protecting against environmental stressors
-
-
-
additional information
?
-
-
ChrR minimizes intracellular H2O2 stress, 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
?
-
-
naphthoquinone-based vitamin (vitamin K1) is not a substrate for purified rat NQO1
-
-
-
additional information
?
-
Q5EI63
TmQR2 could play a role in protecting the infected epidermis
-
-
-
additional information
?
-
-
V5+ down-regulates Nqo1 at the transcriptional level, possibly through inhibiting the ATP-dependent activation of Nrf2
-
-
-
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
-
-
-
NATURAL SUBSTRATES
NATURAL PRODUCTS
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
LITERATURE
(Substrate)
COMMENTARY
(Product)
LITERATURE
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
NAD(P)H + H+ + a quinone
NAD(P)+ + a hydroquinone
show the reaction diagram
P15559
the enzyme catalyzes a detoxification process. QR1 gene expression is induced in response to xenobiotics, oxidants, heavy metals, UV light, and ionisation radiation. The enzyme is part of an electrophilic-induced and/or oxidative stress-induced cellular defense mechanism that includes the induction of more than two dozen defensive genes
-
-
?
NADH + H+ + 17-(allylamino)-17-demethoxygeldanamycin
?
show the reaction diagram
-
NAD(P)H:quinone oxidoreductase 1 in pancreatic cell lines metabolizes the heat shock protein 90 inhibitor 17-(allylamino)-17-demethoxygeldanamycin to the corresponding hydroquinone
-
-
?
NADH + H+ + 2-methyl-1,4-naphthoquinone
NAD+ + 2-methyl-1,4-naphthoquinol
show the reaction diagram
-
-
-
-
?
NADH + H+ + a quinone
NAD+ + a hydroquinone
show the reaction diagram
-
-
-
-
?
NADH + H+ + atovaquone
NAD+ + reduced atovaquone
show the reaction diagram
-
atovaquone is 2-[4-(4-chlorophenyl)cyclohexyl]-3-hydroxynaphthalene-1,4-dione
-
-
?
NADH + H+ + durooquinone
NAD+ + durooquinol
show the reaction diagram
-
-
-
-
?
NADH + H+ + ubiquinone
NAD+ + ubiquinone
show the reaction diagram
-
the enzyme plays an essential role in maintaining a reduced ubiquinone-pool during infection (Plasmodium falciparum is the causative agents of malaria). The enzyme is not only essential to parasite survival in vivo but may also contribute to the severity and outcome of disease. Type II NADH:quinone oxidoreductase the membrane-bound respiratory enzyme differs from the canonical NADH:dehydrogenase (complex I), because it is not involved in the vectorial transfer of protons across membranes. In the electron transport chain of Plasmodium, the canonical multimeric complex I (NADH:dehydrogenase) found in mammalian mitochondria is absent, and, instead, the parasite possesses five quinone-dependent oxidoreductases, namely a type II NADH:quinone oxidoreductase (PfNDH2), a malate: quinone oxidoreductase (MQO), a dihydroorotate dehydrogenase (DHOD), a glycerol-3-phosphate dehydrogenase (G3PDH), and a succinate: quinone oxidoreductase (SDH). These enzymes link cytosolic metabolism to mitochondrial metabolism, generating reducing power (ubiquinol) for the bc1 complex and an aa3-type cytochrome oxidase, enabling proton pumping and energy conservation
-
-
?
NADPH + H+ + 17-(allylamino)-17-demethoxygeldanamycin
?
show the reaction diagram
-
NAD(P)H:quinone oxidoreductase 1 in pancreatic cell lines metabolizes the heat shock protein 90 inhibitor 17-(allylamino)-17-demethoxygeldanamycin to the corresponding hydroquinone
-
-
?
NADPH + H+ + 2-methyl-1,4-naphthoquinone
NADP+ + 2-methyl-1,4-naphthoquinol
show the reaction diagram
-
-
-
-
?
NADPH + H+ + a quinone
NADP+ + a hydroquinone
show the reaction diagram
-
-
-
-
?
NADPH + H+ + durooquinone
NADP+ + durooquinol
show the reaction diagram
-
-
-
-
?
quinone + NAD(P)H
hydroquinone + NAD(P)+
show the reaction diagram
-
possible role in seed germination
-
?
quinone + NAD(P)H
hydroquinone + NAD(P)+
show the reaction diagram
-
protection of cells against damage by reactive oxygen species generated during oxidative cycling of quinones and semiquinone radicals
-
?
vitamin K + NAD(P)H
reduced vitamin K + NAD(P)+
show the reaction diagram
-
-
-
?
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
?
-
-
NQO1 activity colocalizes closely with Alzheimers disease pathology supporting a presumed role as an antioxidant system upregulated in response to the oxidative stress of the Alzheimers disease process
-
-
-
additional information
?
-
-
plays one of the main roles in the bioactivation of quinoidal drugs
-
-
-
additional information
?
-
-
regeneration of alpha-tocopherol may be one of the physiologic functions of this enzyme
-
-
-
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
?
-
-
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
?
-
P0A8G6
role of enzyme in protecting against environmental stressors
-
-
-
additional information
?
-
P58795
role of enzyme in protecting against environmental stressors
-
-
-
additional information
?
-
-
ChrR minimizes intracellular H2O2 stress
-
-
-
additional information
?
-
Q5EI63
TmQR2 could play a role in protecting the infected epidermis
-
-
-
additional information
?
-
-
V5+ down-regulates Nqo1 at the transcriptional level, possibly through inhibiting the ATP-dependent activation of Nrf2
-
-
-
COFACTOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
deamino-NADH
-
-
FAD
-
enzyme contains FAD; stimulates
FAD
-
stimulates
FAD
-
contains 1 mol of FAD per mol of enzyme; enzyme contains FAD
FAD
-
contains 1 mol of FAD per mol of enzyme; enzyme contains FAD
FAD
-
enzyme contains FAD
FAD
-
required
FAD
-
purified recombinant enzyme contains FAD whereas purified native enzyme does not contain FAD
FAD
-
NAD(P)H:quinone acceptor oxidoreductase 2, contains 1 FAD per subunit
FAD
-
each subunit contains a non-covalently bound molecule of FAD
FAD
Q8CHK7
-
flavin
-
flavoenzyme
FMN
-
stimulation
FMN
-
stimulation
FMN
-
contains FNN as prosthetic group
FMN
-
contains FNN as prosthetic group
FMN
P58795
one molecule per monomer
FMN
P0A8G6
one molecule per monomer
NAD(P)H
P15559
Gly149, Tyr155 and His161 are directly involved in the electron transfer from NAD(P)H to FAD and from FADH2 to the quinone
NAD+
-
-
NADH
Sporotrichum pulverulentum
-
-
NADH
-
-
NADH
Q5EI63
can use either NADH or NADPH as an electron donor
NADH
-
C-terminal domain forms part of the binding site for the hydrophilic regions of NADH
NADH
Q8CHK7
-
NADH
-
NDH2 can use both NADH and NADPH as electron donor; PfNDH2 can use both NADH and NADPH as electron donor
NADP+
-
-
NADPH
Sporotrichum pulverulentum
-
-
NADPH
P0A8G6
-
NADPH
Q5EI63
can use either NADH or NADPH as an electron donor
NADPH
-
C-terminal domain forms part of the binding site for the hydrophilic regions of NADPH
NADPH
Q8CHK7
-
NADPH
-
NDH2 can use both NADH and NADPH as electron donor; PfNDH2 can use both NADH and NADPH as electron donor
NADPH
-
-
Nicotinamide riboside
-
recombinant NAD(P)H:quinone acceptor oxidoreductase 2
FMN
O29904
oligomeric flavoprotein binding one FMN per monomer
additional information
-
trans-hydroxytamoxifen-dependent recruitment of coactivators ERbeta and hPMC2 to the electrophile response element sequence of NQO1. Trans-hydroxytamoxifen-dependent corecruitment of the coactivators Nrf2, PARP-1 and topoisomerase IIbeta, both in the presence and absence of ERalpha. Absence of either ERbeta or hPMC2 results in nonrecruitment of PARP-1 and topoisomerase IIbeta, loss of antioxidative enzyme induction and attenuated protection against oxidative DNA damage by trans-hydroxytamoxifen even in the presence of Nrf2 and ERalpha
-
METALS and IONS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
As3+
-
induction of enzyme together with heme oxygenase-1 and glutathione S-transferase Ya
Cd2+
-
induction of enzyme together with heme oxygenase-1 and glutathione S-transferase Ya
Cd2+
-
strongly stimulates NQO1 in the liver of intoxicated rats
Hg2+
-
increase of enzyme mRNA expression, via a transcriptional mechanism
Mn2+
-
strongly stimulates NQO1 in the liver of intoxicated rats
Pb2+
-
increase of enzyme mRNA expression, via a transcriptional mechanism
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
(A)-2-Azido-NAD+
-
photodependent inhibition
(A)-8-azido-NAD+
-
photodependent inhibition
1,10-phenanthroline
-
-
1,10-phenanthroline
-
1 mM, 50% inhibition
1,10-phenanthroline
-
-
1,4-diaminoanthraquinone-2-sulfonic acid
-
-
1,4-Naphthohydroquinone
-
competitive vs. 1,4-naphthohydroquinone, noncompetitive vs. NADPH
1-amino-4-[(3-carboxyphenyl)amino]-anthraquinone-2-sulfonic acid
-
-
1-amino-4-[(4-amino-3-sulfophenyl)amino]-anthraquinone-2-sulfonic acid
-
-
1-aminoanthraquinone
-
-
1-aminoanthraquinone-2-carboxylic acid
-
-
1-hydroxy-2-(1-naphthylmethyl)-3H-benzo[f]chromen-3-one
-
-
1-hydroxy-2-(2-naphthylmethyl)-3H-benzo[f]chromen-3-one
-
-
1-hydroxy-2-dodecyl-4(1H)-quinolone
-
-
1-hydroxy-2-dodecyl-4(1H)quinolone
-
-
1-hydroxy-2-octyl-4(1H)quinolone
-
-
1-hydroxy-2-[2-(nitrooxy)ethyl]-1-oxo-2-(2,4,6-trinitro-3-(nitro[2-(nitrooxy)ethyl]amino)phenyl)diazanium
-
competitive
1-[3,5-dinitro-2-(1,2,3,4-tetrahydronaphthalen-2-yl)phenyl]-1-oxohydrazinium
-
-
10-nitro-5,6-dihydrobenzimidazo[2,1-a]isoquinoline 12-oxide
-
-
10-nitro-5,6-dihydrobenzimidazo[2,1-a]isoquinoline-8-carboxamide 12-oxide
-
-
10-nitro-5,6-dihydrobenzimidazo[2,1-a]isoquinoline-9-carboxamide 12-oxide
-
-
2,10-dinitro-5,6-dihydrobenzimidazo[2,1-a]isoquinoline 12-oxide
-
-
2,2'-dimethoxy-trans-stilbene
-
-
-
2,4'-dimethoxy-cis-stilbene
-
-
2,4'-dimethoxy-trans-stilbene
-
-
-
2,4,4'-trimethoxy-cis-stilbene
-
-
2,4,4'-trimethoxy-trans-stilbene
-
-
-
2,4,6-trinitrotoluene
-
competitive
2,4-dinitro-5-(1,2,3,4-tetrahydronaphthalen-2-yl)benzamide
-
-
2,4-dinitro-5-(5-nitro-1,2,3,4-tetrahydronaphthalen-2-yl)benzamide
-
-
2,4-dinitro-5-(7-nitro-1,2,3,4-tetrahydronaphthalen-2-yl)benzamide
-
-
2,4-Dinitroaniline
-
0.1 mM, 33% inhibition
2,4-Dinitronaphthol
-
0.1 mM, 90% inhibition
2,4-Dinitrophenol
-
0.067 mM, 56% inhibition
2,4-Dinitrophenol
-
0.1 mM, 39% inhibition
2,4-Dinitrophenol
-
-
2,6,4'-trimethoxy-trans-stilbene
-
-
-
2-(2,4,6-trinitrophenyl)-1,2,3,4-tetrahydronaphthalene
-
-
2-(2,4-dinitrophenyl)-1,2,3,4-tetrahydronaphthalene
-
-
2-(2,4-dinitrophenyl)-5-nitro-1,2,3,4-tetrahydronaphthalene
-
-
2-(2,4-dinitrophenyl)-7-nitro-1,2,3,4-tetrahydronaphthalene
-
-
2-(4'-chlorophenyl)-indan-1,3-dione
-
0.0002 mM, 50% inhibition
2-benzyl-1-hydroxy-3H-benzo[f]chromen-3-one
-
-
2-Heptyl-4-hydroxyquinoline-N-oxide
-
-
2-hydroxy-4'-methoxy-trans-stilbene
-
-
-
2-Pivaloyl-1,3-indanedione
-
-
2-[2,4-dinitro-6-(trifluoromethyl)phenyl]-1,2,3,4-tetrahydronaphthalene
-
-
2-[2,4-dinitro-6-(trifluoromethyl)phenyl]-5-nitro-1,2,3,4-tetrahydronaphthalene
-
-
2-[2,4-dinitro-6-(trifluoromethyl)phenyl]-7-nitro-1,2,3,4-tetrahydronaphthalene
-
-
2-[nitro(2,4,6-trinitrophenyl)amino]ethyl nitrate
-
competitive
3,3'-(9H-fluoren-3-ylmethanediyl)bis(4-hydroxy-2H-chromen-2-one)
-
-
3,3'-(biphenyl-4-ylmethanediyl)bis(4-hydroxy-2H-chromen-2-one)
-
-
3,3'-(furan-2-ylmethanediyl)bis(4-hydroxy-2H-chromen-2-one)
-
-
3,3'-(naphthalen-2-ylmethanediyl)bis(4-hydroxy-2H-chromen-2-one)
-
-
3,3'-(phenylmethanediyl)bis(4,7-dihydroxy-2H-chromen-2-one)
-
-
3,3'-(phenylmethanediyl)bis(4-hydroxy-2H-chromen-2-one)
-
-
3,3'-(pyridin-2-ylmethanediyl)bis(4,7-dihydroxy-2H-chromen-2-one)
-
-
3,3'-(quinolin-3-ylmethanediyl)bis(4-hydroxy-2H-chromen-2-one)
-
-
3,3'-(thiophen-2-ylmethanediyl)bis(4-hydroxy-2H-chromen-2-one)
-
-
3,3'-([4-[(E)-2-phenylethenyl]phenyl]methanediyl)bis(4-hydroxy-2H-chromen-2-one)
-
-
3,3'-butane-1,1-diylbis(4-hydroxy-2H-chromen-2-one)
-
-
3,3'-methanediylbis(4,7-dihydroxy-2H-chromen-2-one)
-
-
3,3'-methanediylbis(4-hydroxy-2H-benzo[h]chromen-2-one)
-
-
3,3'-methanediylbis(4-hydroxy-2H-chromen-2-one)
-
-
3,3'-methanediylbis(4-hydroxy-5-methoxy-2H-chromen-2-one)
-
-
3,3'-methanediylbis(4-hydroxy-6,7-dimethoxy-2H-chromen-2-one)
-
-
3,3'-methanediylbis(4-hydroxy-6,7-dimethyl-2H-chromen-2-one)
-
-
3,3'-methanediylbis(4-hydroxy-6,8-dibromo-2H-chromen-2-one)
-
-
3,3'-methanediylbis(4-hydroxy-6-chloro-2H-chromen-2-one)
-
-
3,3'-methanediylbis(4-hydroxy-6-fluoro-2H-chromen-2-one)
-
-
3,3'-methanediylbis(4-hydroxy-6-methoxy-2H-chromen-2-one)
-
-
3,3'-methanediylbis(4-hydroxy-7,8-dimethyl-2H-chromen-2-one)
-
-
3,3'-methanediylbis(4-hydroxy-7-fluoro-2H-chromen-2-one)
-
-
3,3'-methanediylbis(4-hydroxy-7-methoxy-2H-chromen-2-one)
-
-
3,3'-methylene-bis(4-hydroxycoumarin)
-
0.000033 mM, 56% inhibition
3,3'-methylene-bis(4-hydroxycoumarin)
-
0.1 mM, 97% inhibition
3,3'-methylene-bis(4-hydroxycoumarin)
-
only in the presence of glutathione
3,3'-methylene-bis(4-hydroxycoumarin)
-
-
3,3'-methylene-bis(4-hydroxycoumarin)
-
-
3,3'-methylene-bis(4-hydroxycoumarin)
-
competitive vs. NADH, uncompetitive vs. vitamin K1
3,3'-methylene-bis(4-hydroxycoumarin)
-
trivial name dicoumarol, slight inhibition
3,3'-methylene-bis(4-hydroxycoumarin)
-
competitive vs. NADH
3,3'-methylene-bis(4-hydroxycoumarin)
-
0.04 mM, complete inhibition
3,3'-methylene-bis(4-hydroxycoumarin)
-
-
3,3'-methylene-bis(4-hydroxycoumarin)
-
-
3,3'-methylene-bis(4-hydroxycoumarin)
-
-
3,3'-methylene-bis(4-hydroxycoumarin)
-
0.01 mM, 25% inhibition, recombinant NAD(P)H:quinone acceptor oxidoreductase 2
3,3'-methylene-bis(4-hydroxycoumarin)
-
competitive vs. NADH
3,3'-methylene-bis(4-hydroxycoumarin)
-
-
3,3'-methylenebis(4-hydroxy-6-methyl-2H-chromen-2-one)
-
-
3,3'-[(4-chlorophenyl)methanediyl]bis(4-hydroxy-2H-chromen-2-one)
-
-
3,3'-[(4-hydroxy-3-methoxyphenyl)methanediyl]bis(4-hydroxy-2H-chromen-2-one)
-
-
3,3'-[(4-hydroxyphenyl)methanediyl]bis(4-hydroxy-2H-chromen-2-one)
-
-
3,3'-[(4-methoxyphenyl)methanediyl]bis(4-hydroxy-2H-chromen-2-one)
-
-
3,3'-[[3,5-bis(benzyloxy)phenyl]methanediyl]bis(4-hydroxy-2H-chromen-2-one)
-
-
3,3'-[[4-(1-methylethyl)phenyl]methanediyl]bis(4-hydroxy-2H-chromen-2-one)
-
-
3,3'-[[4-(dimethylamino)phenyl]methanediyl]bis(4-hydroxy-2H-chromen-2-one)
-
-
3,4'-dimethoxy-cis-stilbene
-
-
3,4'-dimethoxy-trans-stilbene
-
-
-
3,4,4'-trimethoxy-cis-stilbene
-
-
3,4,4'-trimethoxy-trans-stilbene
-
-
-
3,4,5,4'-tetramethoxy-cis-stilbene
-
-
3,4,5,4'-tetramethoxy-trans-stilbene
-
-
3,5,4'-trimethoxy-cis-stilbene
-
-
3,5,4'-trimethoxy-trans-stilbene
-
-
-
3,5-dihydroxy-4'-methoxy-cis-stilbene
-
-
-
3,5-dihydroxy-4'-methoxy-trans-stilbene
-
-
-
3,5-dinitro-2-(1,2,3,4-tetrahydronaphthalen-2-yl)benzamide
-
-
3,5-dinitro-2-(1,2,3,4-tetrahydronaphthalen-2-yl)benzoic acid
-
-
3,5-dinitro-2-(5-nitro-1,2,3,4-tetrahydronaphthalen-2-yl)benzoic acid
-
-
3,5-dinitro-2-(7-nitro-1,2,3,4-tetrahydronaphthalen-2-yl)benzoic acid
-
-
3-(2,4-difluorophenoxymethyl)-6-methoxy-1,2-dimethylindole-4,7-dione
-
effective inhibitor of the growth of MiaPaCa-2 cells
3-(2-fluoro-4-nitrophenoxymethyl)-5-methoxy-1,2-dimethylindole-4,7-dione
-
-
3-(2-fluoro-4-nitrophenoxymethyl)-6-methoxy-1,2-dimethylindole-4,7-dione
-
effective inhibitor of the growth of MiaPaCa-2 cells
3-(3,4-dimethylbenzyl)-4-hydroxy-2H-chromen-2-one
-
-
3-(3,4-dimethylbenzyl)-4-hydroxy-6,7-dimethyl-2H-chromen-2-one
-
-
3-(4-aminophenoxymethyl)-6-methoxy-1,2-dimethylindole-4,7-dione
-
effective inhibitor of the growth of MiaPaCa-2 cells
3-(4-cyanophenoxymethyl)-6-methoxy-1,2-dimethylindole-4,7-dione
-
effective inhibitor of the growth of MiaPaCa-2 cells; indolequinone derivative 22, dose dependent inhibition of NQO1 activity in MiaPaCa-2
3-(4-fluorophenoxymethyl)-6-methoxy-1,2-dimethylindole-4,7-dione
-
indolequinone derivative 24, dose dependent inhibition of NQO1 activity in MiaPaCa-2
3-(alpha-phenylpropyl)-4-hydroxycoumarin
-
0.01 mM, 50% inhibition
3-benzyl-4-hydroxy-2H-benzo[h]chromen-2-one
-
-
3-benzyl-4-hydroxy-2H-chromen-2-one
-
-
3-benzyl-4-hydroxy-6,7-dimethyl-2H-chromen-2-one
-
-
3-hydroxy-4'-methoxy-cis-stilbene
-
-
-
3-hydroxy-4'-methoxy-trans-stilbene
-
-
-
3-hydroxy-4,4'-dimethoxy-cis-stilbene
-
-
3-hydroxy-4,4'-dimethoxy-trans-stilbene
-
-
-
3-methoxy-1,2-dimethyl-3-(3-pyridyloxymethyl)indole-4,7-dione
-
-
3-[alpha-(4'-nitrophenyl)-beta-acetylethyl]-4-hydroxycoumarin
-
0.02 mM, 50% inhibition
3-[[3-[bis(4-hydroxy-2-oxo-2H-chromen-3-yl)methyl]phenyl](4-hydroxy-2-oxo-4a,8a-dihydro-2H-chromen-3-yl)methyl]-4-hydroxy-2H-chromen-2-one
-
-
3-[[4-[bis(4-hydroxy-2-oxo-2H-chromen-3-yl)methyl]phenyl](4,7-dihydroxy-2-oxo-4a,8a-dihydro-2H-chromen-3-yl)methyl]-4,7-dihydroxy-2H-chromen-2-one
-
-
3-[[4-[bis(4-hydroxy-2-oxo-2H-chromen-3-yl)methyl]phenyl](4-hydroxy-2-oxo-4a,8a-dihydro-2H-chromen-3-yl)methyl]-4-hydroxy-2H-chromen-2-one
-
-
4',5,7-trihydroxyflavone
-
0.01 mM, 61% inhibition, recombinant NAD(P)H:quinone acceptor oxidoreductase 2
4,10-dinitro-5,6-dihydrobenzimidazo[2,1-a]isoquinoline 12-oxide
-
-
4,10-dinitro-5,6-dihydrobenzimidazo[2,1-a]isoquinoline-9-carboxamide 12-oxide
-
-
4,10-dinitro-8-(trifluoromethyl)-5,6-dihydrobenzimidazo[2,1-a]isoquinoline 12-oxide
-
-
4,4'-dichlorodicoumarol
-
0.001 mM, 50% inhibition
4,4'-dimethoxy-cis-stilbene
-
-
-
4,4'-dimethoxy-trans-stilbene
-
-
-
4,5,6,7-tetranitro-1,3-dihydro-2H-benzimidazol-2-one
-
competitive
4,5,6-trinitro-1,3-dihydro-2H-benzimidazol-2-one
-
competitive
4-amino-2H-chromen-2-one
-
-
4-chloromercuribenzoate
-
74% residual activity at 0.15 mM
4-hydroxy-3-(1-naphthylmethyl)-2H-benzo[h]chromen-2-one
-
-
4-hydroxy-3-(1-naphthylmethyl)-2H-chromen-2-one
-
-
4-hydroxy-3-(2-naphthylmethyl)-2H-benzo[h]chromen-2-one
-
-
4-hydroxy-3-(2-naphthylmethyl)-2H-chromen-2-one
-
-
4-hydroxy-3-(naphthalen-1-yl)cyclohepta[h]chromen-2(7H)-one
-
-
4-hydroxy-3-(naphthalen-2-yl)cyclohepta[h]chromen-2(7H)-one
-
-
4-hydroxy-3-phenylcyclohepta[h]chromen-2(7H)-one
-
-
4-hydroxy-6,7-dimethyl-3-(1-naphthylmethyl)-2H-chromen-2-one
-
-
4-hydroxy-6,7-dimethyl-3-(2-naphthylmethyl)-2H-chromen-2-one
-
-
4-hydroxy-6,7-dimethyl-3-(naphthalen-1-yl)-2H-chromen-2-one
-
-
4-hydroxy-6,7-dimethyl-3-(naphthalen-2-yl)-2H-chromen-2-one
-
-
4-hydroxy-6,7-dimethyl-3-phenyl-2H-chromen-2-one
-
-
4-Hydroxycoumarin
-
-
4-hydroxymercuribenzoate
-
0.067 mM, 50% inhibition
4-Methoxycoumarin
-
-
4-[bis(4-hydroxy-2-oxo-2H-chromen-3-yl)methyl]benzoic acid
-
-
5,5'-dithiobis(2-nitrobenzoic acid)
-
-
5,5'-dithiobis(2-nitrobenzoic acid)
-
1 mM, 67% inhibition, 10 mM, complete inhibition
5,6-dimethylxanthenone-4-acetic acid
-
tumour blood flow inhibitor, competitive vs. NADH
5,7-dihydroxyflavone
-
0.009 mM, approx. 90% inhibition
5,7-dihydroxyflavone
-
0.009 mM, approx. 20% inhibition
5,7-dihydroxyflavone
-
0.009 mM, approx. 80% inhibition
5,7-dihydroxyflavone
-
0.00018 mM, 50% inhibition
5-hydroxy-7-bromoacetylflavone
-
0.00018 mM, 50% inhibition, irreversible, useful as affinity label
5-methoxy-1,2-dimethyl-3-(2,4,6-trifluorophenoxymethyl)indole-4,7-dione
-
effective inhibitor of the growth of MiaPaCa-2 cells; indolequinone derivative 10, mechanism based 80% inhibition
5-methoxy-1,2-dimethyl-3-(2-nitrophenoxymethyl)indole-4,7-dione
-
effective inhibitor of the growth of MiaPaCa-2 cells
5-methoxy-1,2-dimethyl-3-(3-nitrophenoxymethyl)indole-4,7-dione
-
effective inhibitor of the growth of MiaPaCaa-2 cells; indolequinone derivative 6, dose dependent inhibition of NQO1 activity in MiaPaCa-2
5-methoxy-1,2-dimethyl-3-(3-pyridyloxymethyl)indole-4,7-dione
-
indolequinone derivative 12, dose dependent inhibition of NQO1 activity in MiaPaCa-2
5-methoxy-1,2-dimethyl-3-(4-nitrophenoxymethyl)indole-4,7-dione
-
effective inhibitor of the growth of MiaPaCa-2 cells
5-methoxy-1,2-dimethyl-3-(phenoxymethyl)indole-4,7-dione
-
-
5-methoxy-1,2-dimethyl-3-(pyridin-2-yloxymethyl)indole-4,7-dione
-
indolequinone derivative 11, mechanism based 90% inhibition
5-methoxy-1,2-dimethyl-3-(pyridin-4-yloxymethyl)indole-4,7-dione
-
-
5-methoxy-1,2-dimethyl-3-[(4-nitrophenoxy)methyl]-indole-4,7-dione
-
ES936, potent mechanism-based inhibitor of NQO1, complete inhibition at 0.001 mM
5-methoxy-1,2-dimethyl-3-[(4-nitrophenoxy)methyl]indole-4,7-dione
-
mechanism-based inhibitor, time- and concentration dependent inhibition that requires the presence of NAD(P)H, 0.0015 mM, complete inhibition after 4 min
5-methoxy-1,2-dimethyl-3-[(4-nitrophenoxy)methyl]indole-4,7-dione
-
ES936, potent inhibitor of NQO1 activity and cell proliferation. Approximately 90% inhibition of enzyme activity after 4 h. Inactivation is dependent upon NADH
5-methoxy-1,2-dimethyl-3-[(4-pyridinyloxy)methyl]indole-4,7-dione
-
approximately 90% inhibition of enzyme activity after 4 h, and this inactivation is dependent upon NADH
5-methoxy-1,2-dimethyl-3-[1-(4-nitrophenoxy)ethyl]indole-4,7-dione
-
-
5-methoxy-1,2-dimethyl-[(4-nitrophenoxy)methyl]indole-4,7-dione
-
-
6-methoxy-1,2-dimethyl-3-(2,4,6-trifluorophenoxymethyl)indole-4,7-dione
-
effective inhibitor of the growth of MiaPaCa-2 cells; indolequinone derivative 26, mechanism based 90% inhibition
6-methoxy-1,2-dimethyl-3-(2-nitrophenoxymethyl)indole-4,7-dione
-
effective inhibitor of the growth of MiaPaCaa-2 cells
6-methoxy-1,2-dimethyl-3-(3-nitrophenoxymethyl)indole-4,7-dione
-
effective inhibitor of the growth of MiaPaCa-2 cells
6-methoxy-1,2-dimethyl-3-(4-nitrophenoxymethyl)indole-4,7-dione
-
effective inhibitor of the growth of MiaPaCa-2 cells; indolequinone derivative 15, mechanism based 85% inhibition
6-methoxy-1,2-dimethyl-3-(phenoxymethyl)indole-4,7-dione
-
-
6-methoxy-1,2-dimethyl-3-(pyridin-2-yloxymethyl)indole-4,7-dione
-
indolequinone derivative 27, mechanism based 90% inhibition
6-methoxy-1,2-dimethyl-3-(pyridin-4-yloxymethyl)indole-4,7-dione
-
indolequinone derivative 29, mechanism based 95% inhibition
6-methoxy-1,2-dimethyl-3-[(4-nitrophenoxy)methyl]indole-4,7-dione
-
approximately 90% inhibition of enzyme activity after 4 h, and this inactivation is dependent upon NADH
6-methoxy-1,2-dimethyl-3-[(4-pyridinyloxy)methyl]indole-4,7-dione
-
approximately 90% inhibition of enzyme activity after 4 h, and this inactivation is dependent upon NADH
6-methoxy-1,2-dimethyl-3-[(acetoxy)methyl]indole-4,7-dione
-
approximately 90% inhibition of enzyme activity after 4 h, and this inactivation is dependent upon NADH
6-methoxy-1,2-dimethyl-3-[2-nitrophenoxymethyl]indole-4,7-dione
-
indolequinone derivative 19, mechanism based 95% inhibition, dose dependent inhibition of NQO1 activity in MiaPaCa-2
6-methoxy-1,2-dimethyl-3-[4-(trifluoromethyl)phenoxymethyl]-indole-4,7-dione
-
effective inhibitor of the growth of MiaPaCa-2 cells; indolequinone derivative 23, dose dependent inhibition of NQO1 activity in MiaPaCa-2
7,8-dibromoacetylflavone
-
0.00003 mM, 50% inhibition
7,8-dihydroxyflavone
-
-
7-(4-hydroxy-2-oxo-2H-chromen-3-yl)-6a,7-dihydro-4aH,6H,8H-pyrano[3,2-c:5,6-c']dichromene-6,8-dione
-
-
7-(4-hydroxy-2-oxo-2H-chromen-3-yl)-6H,7H-chromeno[4,3-b]chromen-6-one
-
-
7-bromoacetylflavone
-
time-dependent inactivation within 30 s, 0.00074 mM, 50% inhibition
7-hydroxyflavone
-
-
7-hydroxylflavone
-
competitive inhibition, 0.00074 mM, 50% inhibition
7-N-acetyldemethyllavendamycin n-butyl amide
P15559
lavendamycin analogue 12, selective toxic toward NQO1-rich cells
8-hydroxyquinoline
-
1 mM, 50% inhibition
acid blue 25
-
-
ADP
-
86% residual activity at 0.2 mM
Alizarin Red S
-
0.04 mM, 38% inhibition
alpha,alpha'-dipyridyl
-
IC50: 1 mM
alpha-Naphthoflavone
-
0.01 mM, 75% inhibition, recombinant NAD(P)H:quinone acceptor oxidoreductase 2
Amytal
-
6.6 mM, 55% inhibition
anthraquinone
-
-
anthraquinone-2-carboxylic acid
-
-
anthraquinone-2-sulfonic acid
-
-
ATP
-
91% residual activity at 0.2 mM
benzoquinol
-
shows noncompetitive inhibition in all conditions, it can bind to multiple enzyme forms or sites, even when either of the substrates (NADH or benzoquinone) is present at high concentrations
beta-Naphthoflavone
-
0.01 mM, 76% inhibition, recombinant NAD(P)H:quinone acceptor oxidoreductase 2
bis-3,3'-(4-hydroxycoumarinyl)acetoacetate
-
trivial tromexan, 0.1 mM, 79% inhibition
-
bis-3,3'-(4-hydroxycoumarinyl)acetoacetate
-
-
-
bromaminic acid
-
-
capsaicin
-
activity is decreased after the treatment with capsaicin or dicoumarol. Quinone metabolites or other reactive forms of capsaicin may bind covalently to NQO1 and thereby inhibit its activity, leading to production of reactive oxygen species; suppresses NQO1 expression and activity. Quinone metabolites or other reactive forms of capsaicin may bind covalently to NQO1 and thereby inhibit its activity, leading to production of reactive oxygen species
chrysin
-
0.01 mM, 100% inhibition, recombinant NAD(P)H:quinone acceptor oxidoreductase 2
chrysin
-
-
Cibacron blue
-
and related anthraquinone dyes
Cibacron blue
-
-
Cibacron Blue F3G-A
-
0.04 mM, 75% inhibition
cis-stilbene
-
-
-
Cr6+
-
decrease of enzyme mRNA level together with heme oxygenase-1 and glutathione S-transferase Ya
Cu2+
-
decrease of enzyme mRNA expression, via a transcriptional mechanism
curcumin
-
inhibition of enzyme activity in vivo and in vitro. Inducues dissociation of complexes of enzyme with tumor suppressor protein p53 leading to degradation of p53, but not of p53 cancer hot-spot mutant R273H
dicoumarol
-
binding of dicoumarol induces conformational changes involving Y128 and F232 on the surface of enzyme catalytic pocket
dicoumarol
Q5EI63
-
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
-
inhibitor of NQO1, inhibits clonogenic cell death caused by beta-lap
dicoumarol
-
in the presence of 0.050 mM of dicoumarol, the protective effect of bromocriptine against H2O2 is completely abolished
dicoumarol
-
-
dicoumarol
-
i.e. 3,3'-methylenebis(4-hydroxycoumarin), potent competitive inhibitor of NQO1
Dicoumarol dimethylether
-
0.0005, 50% inhibition
dicumarol
-
-
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
dicumarol
-
most potent inhibitor, 12% residual activity at 0.15 mM
diphenylene iodonium chloride
-
-
EGTA
-
95% residual activity at 5 mM
ES 936
-
-
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
ES936
-
is an irreversible mechanism-based inhibitor of QR1
ethyl 5-aziridin-1-yl-2,4-dinitrobenzoate
-
competitive
ethyl bis(4-hydroxy-2-oxo-2H-chromen-3-yl)acetate
-
-
flavone-8-acetic acid
-
tumour blood flow inhibitor, competitive vs. NADH
galangin
-
0.01 mM, 100% inhibition, recombinant NAD(P)H:quinone acceptor oxidoreductase 2
HgCl2
-
0.2 mM, 94% inhibition
hydroxy(oxo)(3,6,8-trinitro-9H-carbazol-1-yl)ammonium
-
competitive
iodoacetic acid
-
-
isorhamnetin
-
-
lavendamycin beta-hydroxyethyl ester
P15559
lavendamycin analogue 12, selective toxic toward NQO1-rich cells
Mersalyl
-
68% residual activity at 0.15 mM
methylene-5,5'-bis(4,6-dioxo-2-methyldihydropyran)
-
0.003 mM, 50% inhibition
morin
-
0.01 mM, 95% inhibition, recombinant NAD(P)H:quinone acceptor oxidoreductase 2
N-ethyl maleimide
-
0.33 mM, complete inhibition
N-ethylmaleimide
-
-
N-methyl-N,2,4,6-tetranitroaniline
-
competitive
N-methyl-N,2,4-trinitroaniline
-
competitive
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
NAD+
-
96% residual activity at 0.2 mM
NADP+
-
noncompetitive vs. NADPH
NADP+
-
95% residual activity at 0.2 mM
nitracrine
-
competitive
p-chloromercuribenzoate
-
-
Phenindione
-
0.1 mM, 92% inhibition
phenylmercuric acetate
-
-
pinosylvin
-
-
Procion blue M-3GS
-
-
Procion blue MX-R
-
0.04 mM, 75% inhibition
quercetin
-
0.01 mM, 100% inhibition, recombinant NAD(P)H:quinone acceptor oxidoreductase 2
quercetin
-
-
quinacrine dihydrochloride
-
0.05 mM, 65-95% inhibition depending on substrate
reserpine
-
competitive inhibitor of DT-diaphorase
resveratrol
-
-
salicylate
-
1 mM, 62% inhibition
siRNA
-
siRNA for NQO1 inhibits clonogenic cell death caused by beta-lap
-
SOD
-
inhibits the NADPH:chromate reductase reaction of NQO1
-
Thenoyltrifluoroacetone
-
-
trans-stilbene
-
-
-
vitamin E
-
-
Warfarin
-
1 mM, 70% inhibition
mitomycin C
-
mechanism-based inhibitor, in a pH-dependent manner
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
-
-
-
additional information
-
not inhibited by o-phenanthroline, KCN, quinacrine, EDTA and 2,3-dimercapto-1-propanol
-
additional information
-
microsomal enzyme: not inhibited by dicoumarol, lapachol and p-chloromercuribenzoate
-
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
-
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
-
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
-
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
-
growth inhibitory effects of series of methoxystilbenes (E and Z isomers) related to resveratrol on human cancer cell lines, overview
-
additional information
-
enzyme induction effects of series of methoxystilbenes (E and Z isomers) related to resveratrol on murine hepatoma cells, overview
-
additional information
-
synthesis of 2-nitroaryl-1,2,3,4-tetrahydroisoquinolines, nitro-substituted 5,6-dihydrobenzimidazo[2,1-a]isoquinoline N-oxides and related heterocycles as potential bioreducible substrates for the enzymes NAD(P)H: quinone oxidoreductase 1, NQO1, overview
-
ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
1,1'-(E)-ethene-1,2-diylbis(2-methoxybenzene)
-
at 12.5 micromol, induces quinone reductase to a greater extent than resveratrol
1,2-dithiole-3-thione
-
induces enzyme expression
1,3-dimethoxy-2-[(E)-2-(4-methoxyphenyl)ethenyl]benzene
-
at 12.5 micromol, induces quinone reductase to a greater extent than resveratrol
1-(3,4-dihydroxybenzyl)-1,2,3,4-tetrahydro-6,7-isoquinolinediol
-
up-regulation of enzyme upon exposure to L-dopa and tetrahydropapaveroline
1-methoxy-2-[(E)-2-(4-methoxyphenyl)ethenyl]benzene
-
at 6.3 micromol is 1.8 times more effective than resveratrol as a quinone reductase inducer
1-methoxy-3-[(E)-2-(4-methoxyphenyl)ethenyl]benzene
-
at 12.5 micromol, induces quinone reductase to a greater extent than resveratrol
2-mercaptoethanol
-
stimulates
2-methoxy-5-[(E)-2-(4-methoxyphenyl)ethenyl]phenol
-
at 12.5 micromol, induces quinone reductase to a greater extent than resveratrol
3-nitrobenzanthrone
-
increases protein level and enzymatic activity of NQO1. Up to a 2.5fold increase in NQO1 activity with menadione as substrate in tissues of rats treated with 3-nitrobenzanthrone
3H-1,2-dithiole-3-thione
-
significantly increases cellular NQO1 activity and mRNA levels. Induces NQO1 in a concentration-dependent manner. In SH-SY5Y cells, 2fold induction of cellular NQO1 with 0.01 mM and 3-5.5fold induction of NQO1 with 0.05 and 0.1 mM. 4.5fold increase of NQO1 mRNA between 12 and 24 h after treatment. 40% induction of cellular NQO1 after treatment of primary human neurons at a concentration of 0.01 mM
actinomycin D
-
treatment of the cells with actinomycin D alone for 6 h significantly inhibits the constitutive NQO1 mRNA level by approximately 80%. KTZ- and ITZ-mediated Nqo1 induction is completely inhibited
alpha-methylbenzyl isothiocyanate
-
in vivo, the organ most susceptible to the inductive activity of the isothiocyanates is the urinary bladder, with alpha-methylbenzyl isothiocyanate and cyclohexylmethyl isothiocyanate being the most effective. Inductive activity in the bladder in vivo does not correlate with that in bladder cells in vitro
ascorbic acid
-
superinduction of the enzyme induction by As3+
beta-napthoflavone
-
-
bromocriptine
-
significantly upregulates expression and activity (911% of untreated control) of NQO1, attenuates increase in protein-bound quinone in H2O2-treated PC12 cells, and protects PC12 cells against oxidative damage. Bromocriptine increases the expression and nuclear translocation of a basic leucine zipper transcription factor Nrf2, involved in the regulation of the enzyme
butylated hydroxyanisole
-
inducer
Clofibrate
-
administration to animals for 5 to 10 days, increase in enzyme protein and activity
cyclohexylmethyl isothiocyanate
-
in vivo, the organ most susceptible to the inductive activity of the isothiocyanates is the urinary bladder, with alpha-methylbenzyl isothiocyanate and cyclohexylmethyl isothiocyanate being the most effective. Inductive activity in the bladder in vivo does not correlate with that in bladder cells in vitro
cysteine
-
stimulates
Desferrioxamine
-
stimulates the NADPH:chromate reductase reaction of NQO1
duroquinone
-
stimulates NQO1 activity
Eugenol
-
increases expression and activity of enzyme by NF-E2 related factor2 binding to antioxidant response element in enzyme gene; increases the expression and activity of NAD(P)H:quinone oxidoreductase through NF-E2 related factor2 binding to antioxidant response element in QR gene in a dose-dependent manner
GSH
-
maximal stimulation with 0.5 mM, approx. 3fold activity
isorhamnetin
-
-
itraconazole
-
induces NQO1 mRNA and enzymatic activity levels in a concentration- and time-dependent manner in wild-type but not aryl hydrocarbon receptor-deficient Hepa-1c1c7 cells. Increases NQO1 de novo RNA synthesis without significantly affecting the levels of existing RNA. 50 micromol shows maximum NQO1 mRNA induction
ketoconazole
-
induces NQO1 mRNA and enzymatic activity levels in a concentration- and time-dependent manner in wild-type but not aryl hydrocarbon receptor-deficient Hepa-1c1c7 cells. Increases NQO1 de novo RNA synthesis without significantly affecting the levels of existing RNA. 25 micromol shows maximum NQO1 mRNA induction
oltipraz
-
inducer
oltipraz
-
induces enzyme expression
quercetin
-
induces enzyme expression
resveratrol
-
at 25 micromol increases quinone reductase activity by 1.5fold. Resveratrol induces quinone reductase activity of the wild type Hepa-1c1c7 cells to the same extent as the mutant c1 cells that lack a phase I enzyme
rutaecarpine
-
induces enzyme activity and gene expression by transactivation of activator protein-1 in a dose-dependent manner; isolated from Evodia rutaecarpa, induces QR gene expression and activity through increase of activator protein-1, Evodia rutaecarpa is used in traditional Chinese medicine
sulforaphane
-
at a concentration of 5 micromol significantly induces NQO1 mRNA in both wild-type and C12 cells
sulforaphane
-
induces enzyme expression
tert-butylhydroxy-anisole
-
induces enzyme expression
vitamin C
-
-
L-Dopa
-
up-regulation of enzyme upon exposure to L-dopa and tetrahydropapaveroline
additional information
-
about 10fold induction of enzyme expression by H2O2
-
additional information
-
vegetable consumption only is not associated with NQO1 mRNA level or NQO1 activity
-
additional information
-
fluconazole does not induce NQO1
-
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 42C 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
-
irradiation with 4 Gy causes a long-lasting upregulation of NQO1, thereby increasing NQO1-mediated beta-lap-induced cell deaths
-
additional information
-
is elevated in many tumors
-
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.0058
1,4-benzoquinone
P0A8G6
pH 7.2, 37C
0.037
1,4-benzoquinone
P58795
pH 7.2, 37C
0.0233
2,6-dichloroindophenol
-
-
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
0.115
2-methoxy-5-(methoxymethyl)-2,5-cyclohexadiene
-
-
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
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
0.84
5-(aziridin-1-yl)-4-hydroxylamino-2-benzamide
-
-
1.28
5-(aziridin-1-yl)-4-hydroxylamino-2-benzamide
-
-
1.37
5-(aziridin-1-yl)-4-hydroxylamino-2-benzamide
-
-
0.11
benzoquinone
-
pH 7.5, 70C
14.9
benzoquinone
-
at 0.02 mM, pH 6.0, 23C
19
benzoquinone
-
at 0.01 mM, pH 6.0, 23C
19.3
benzoquinone
-
at 0.05 mM, pH 6.0, 23C
36.3
benzoquinone
-
at 0.1 mM, pH 6.0, 23C
0.26
chromate(IV)
-
pH 5.0, 70C
0.12
coenzyme Q1
-
pH 8.5, 60C
0.028
dihydronicotinamide riboside
-
recombinant NAD(P)H:quinone acceptor oxidoreductase 2
0.07
dihydronicotinamide riboside
-
recombinant NAD(P)H:quinone acceptor oxidoreductase 1
0.21
duroquinone
-
pH 8.0, 70C
0.435
duroquinone
-
pH 8.0, reaction with duroquinone
0.0000017
FAD
-
hydrophobic isoform
0.0000027
FAD
-
hydrophilic isoform
0.000188
menadione
-
cofactor NADH
0.00024
menadione
-
cofactor NADPH
0.00196
menadione
-
hydrophilic isoform
0.002
menadione
-
-
0.002
menadione
-
-
0.0023
menadione
-
recombinant NAD(P)H:quinone acceptor oxidoreductase 2
0.00247
menadione
-
hydrophobic isoform
0.0025
menadione
-
cofactor NADH
0.0026
menadione
-
-
0.0027
menadione
-
recombinant NAD(P)H:quinone acceptor oxidoreductase 1
0.00336
menadione
Q5EI63
pH 7.5, 25C
0.0041
menadione
-
-
0.035
menadione
-
cofactor NADH
0.04 - 0.05
menadione
-
in untreated vesicles, in low salt disrupted membranes and in French-press treated preparations
0.04
menadione
-
cofactor NADPH
0.0863
menadione
-
-
0.125
menadione
-
in low-salt and detergent-solubilized fractions
0.23
menadione
-
pH 8.0, 60C
0.0047
Methyl red
-
recombinant NAD(P)H:quinone acceptor oxidoreductase 2
0.028
Methyl red
-
recombinant NAD(P)H:quinone acceptor oxidoreductase 1
0.0051
NADH
-
cosubstrate: decylubiquinone
0.0062
NADH
-
-
0.014
NADH
P0A8G6
pH 7.2, 37C
0.0167
NADH
-
cosubstrate: ubiquinone-1
0.0175
NADH
-
-
0.019
NADH
P58795
pH 7.2, 37C
0.02 - 0.05
NADH
-
-
0.0305
NADH
-
in the presence of 0.026 mM dicoumarol
0.034
NADH
-
-
0.045
NADH
-
-
0.045
NADH
-
reduction of naphthoquinone
0.0643
NADH
-
hydrophilic isoform
0.074
NADH
-
-
0.0881
NADH
-
hydrophobic isoform
0.1
NADH
-
-
0.11
NADH
-
-
0.12
NADH
-
-
0.19
NADH
-
-
0.2
NADH
-
pH 8.0, reaction with plumbagin
0.204
NADH
-
pH 8.0, reaction with menadione
0.223
NADH
-
cofactor menadione
0.25
NADH
-
pH 8.0, reaction with juglone
0.29
NADH
-
-
0.32
NADH
-
-
0.333
NADH
-
pH 8.0, reaction with p-benzoquinone
0.34
NADH
-
in 10 mM bis-Tris-propane buffer (pH 7.2), at 25C
0.341
NADH
-
-
0.375
NADH
-
pH 8.0, reaction with duroquinone
0.549
NADH
-
reduction of menadione
16.2
NADH
-
at 0.02 mM, pH 6.0, 23C
19
NADH
-
at 0.01 mM, pH 6.0, 23C
20.7
NADH
-
at 0.05 mM, pH 6.0, 23C
28.2
NADH
-
at 0.1 mM, pH 6.0, 23C
125
NADH
-
-
0.03
NADPH
-
reduction of menadione
0.031
NADPH
P58795
pH 7.2, 37C
0.033
NADPH
-
reduction of naphthoquinone
0.0581
NADPH
-
hydrophobic isoform
0.0625
NADPH
P39315
mutant Y140F, pH 7.5, temperature not specified in the publication
0.0656
NADPH
P39315
wild-type, pH 7.5, temperature not specified in the publication
0.066
NADPH
-
hydrophilic isoform
0.085
NADPH
-
-
0.0915
NADPH
P39315
mutant W139F, pH 7.5, temperature not specified in the publication
0.12
NADPH
-
-
0.17
NADPH
-
-
0.17
NADPH
P0A8G6
pH 7.2, 37C
0.19
NADPH
-
-
0.195
NADPH
P39315
mutant W139I, pH 7.5, temperature not specified in the publication
0.22
NADPH
-
-
0.225
NADPH
P39315
mutant W139A, pH 7.5, temperature not specified in the publication
0.24
NADPH
-
-
0.27
NADPH
-
pH 8.0, reaction with plumbagin
0.286
NADPH
-
pH 8.0, reaction with juglone
0.322
NADPH
-
pH 8.0, reaction with menadione
0.34
NADPH
-
acceptor menadione
0.384
NADPH
-
pH 8.0, reaction with p-benzoquinone
0.395
NADPH
P39315
mutant N143A, pH 7.5, temperature not specified in the publication
0.403
NADPH
P39315
mutant N143L, pH 7.5, temperature not specified in the publication
0.000437
naphthoquinone
-
cofactor NADH
0.00059
naphthoquinone
-
cofactor NADPH
1.4
potassium ferricyanide
-
cofactor NADPH
1.7
potassium ferricyanide
-
cofactor NADH
0.0143
reduced nicotinamide 2-azidoadenine dinucleotide
-
-
0.0185
reduced nicotinamide 8-azidoadenine dinucleotide
-
-
0.0065
ubiquinone-0
-
in 10 mM bis-Tris-propane buffer (pH 7.2), at 25C
0.0641
vitamin K1
-
-
0.3
vitamin K1
-
cofactor NADPH
0.33
vitamin K1
-
cofactor NADH
0.024
methylene blue
-
cofactor NADPH
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
-
TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
370
1,4-benzoquinone
P0A8G6
pH 7.2, 37C
769
1,4-benzoquinone
-
pH 7.0
3200
1,4-benzoquinone
P58795
pH 7.2, 37C
431
1,4-Naphthoquinone
-
pH 7.0
431
1,4-Naphthoquinone
-
pH 7.0, 25C
0.5
1,8-dihydroxy-9,10-anthraquinone
-
pH 7.0, 25C
4.4
2,3-diglutathionyl-1,4-naphthoquinone
-
pH 7.0
40
2,5-bis(ethylamine)-3,6-diaziridinyl-1,4-benzoquinone
-
pH 7.0, 25C
1550
2,5-diaziridinyl-1,4-benzoquinone
-
pH 7.0, 25C
2331
2,5-diaziridinyl-1,4-benzoquinone
-
pH 7.0
2000
2,5-diaziridinyl-3-(hydroxymethyl)-6-methyl-1,4-benzoquinone
-
pH 7.0, 25C
500
2,5-dimethyl-1,4-benzoquinone
-
pH 7.0
500
2,5-dimethyl-1,4-naphthoquinone
-
pH 7.0, 25C
111
2,5-dimethyl-3,6-diaziridinyl-1,4-benzoquinone
-
pH 7.0, 25C
222
2,5-dimethyl-3,6-diaziridinyl-1,4-benzoquinone
-
pH 7.0
46.7
2,6-dichlorophenolindophenol
-
recombinant NAD(P)H:quinone acceptor oxidoreductase 2
600
2,6-dichlorophenolindophenol
-
recombinant NAD(P)H:quinone acceptor oxidoreductase 1
625
2,6-dimethyl-1,4-benzoquinone
-
pH 7.0
232
2-Hydroxy-1,4-naphthoquinone
-
pH 7.0, 25C
287
2-methyl-1,4-benzoquinone
-
pH 7.0
287
2-methyl-1,4-benzoquinone
-
pH 7.0, 25C
380
2-methyl-1,4-naphthoquinone
-
pH 7.0
380
2-methyl-1,4-naphthoquinone
-
pH 7.0, 25C
26.3
2-methyl-3-glutathionyl-5-hydroxy-1,4-naphthoquinone
-
pH 7.0
1540
2-methyl-5-aziridinyl-1,4-benzoquinone
-
pH 7.0, 25C
500
2-methyl-5-hydroxy-1,4-naphthoquinone
-
pH 7.0
500
2-methyl-5-hydroxy-1,4-naphthoquinone
-
pH 7.0, 25C
11
3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium
-
recombinant NAD(P)H:quinone acceptor oxidoreductase 2
71
5,8-Dihydroxy-1,4-naphthoquinone
-
pH 7.0
71
5,8-Dihydroxy-1,4-naphthoquinone
-
pH 7.0, 25C
0.01
5-(aziridin-1-yl)-2,4-dinitrobenzamide
-
recombinant NAD(P)H:quinone acceptor oxidoreductase 2
6
5-(aziridin-1-yl)-2,4-dinitrobenzamide
-
recombinant NAD(P)H:quinone acceptor oxidoreductase 2
242
5-hydroxy-1,4-naphthoquinone
-
pH 7.0
242
5-hydroxy-1,4-naphthoquinone
-
pH 7.0, 25C
2.3
9,10-anthraquinone-2,6-disulfonate
-
pH 7.0
52
9,10-phenanthrene quinone
-
pH 7.0
52
9,10-phenanthrene quinone
-
pH 7.0, 25C
930
benzoquinone
-
pH 7.5, 70C
1.8
chromate
-
at pH 7.0 and 27C
5.8
chromate(IV)
-
pH 5.0, 70C
6.4
coenzyme Q1
-
pH 8.5, 60C
43.3
dihydronicotinamide riboside
-
recombinant NAD(P)H:quinone acceptor oxidoreductase 2
517
dihydronicotinamide riboside
-
recombinant NAD(P)H:quinone acceptor oxidoreductase 1
25
duroquinone
-
pH 8.0, 70C
0.11
menadione
-
at pH 7.0 and 27C
23.1
menadione
-
cofactor NADH
34.8
menadione
-
cofactor NADPH
38.3
menadione
-
recombinant NAD(P)H:quinone acceptor oxidoreductase 2
350.7
menadione
-
-
440
menadione
-
pH 8.0, 60C
550
menadione
-
recombinant NAD(P)H:quinone acceptor oxidoreductase 1
11700
menadione
-
-
0.333
Methyl red
-
recombinant NAD(P)H:quinone acceptor oxidoreductase 1
3.83
Methyl red
-
recombinant NAD(P)H:quinone acceptor oxidoreductase 2
8.9
NADH
P0A8G6
pH 7.2, 37C
31.7
NADH
-
reduction of menadione
62.7
NADH
-
reduction of naphthoquinone
120
NADH
P58795
pH 7.2, 37C
192
NADH
-
-
6
NADPH
P0A8G6
pH 7.2, 37C
18.7
NADPH
P39315
mutant N143A, pH 7.5, temperature not specified in the publication
25.2
NADPH
P39315
mutant N143L, pH 7.5, temperature not specified in the publication
32.3
NADPH
P39315
mutant W139A, pH 7.5, temperature not specified in the publication
34.2
NADPH
P39315
wild-type, pH 7.5, temperature not specified in the publication
37.1
NADPH
P39315
mutant W139F, pH 7.5, temperature not specified in the publication
45.2
NADPH
P39315
mutant Y140F, pH 7.5, temperature not specified in the publication
47.5
NADPH
-
reduction of naphthoquinone
52.7
NADPH
-
reduction of menadione
53.5
NADPH
P39315
mutant W139I, pH 7.5, temperature not specified in the publication
170
NADPH
P58795
pH 7.2, 37C
29.9
naphthoquinone
-
cofactor NADH
39.3
naphthoquinone
-
cofactor NADPH
167
reduced nicotinamide 2-azidoadenine dinucleotide
-
-
91
reduced nicotinamide 8-azidoadenine dinucleotide
-
-
1000
tetramethyl-1,4-benzoquinone
-
pH 7.0, 25C
kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
48
NADPH
P39315
mutant N143A, pH 7.5, temperature not specified in the publication
5
63
NADPH
P39315
mutant N143L, pH 7.5, temperature not specified in the publication
5
144
NADPH
P39315
mutant W139A, pH 7.5, temperature not specified in the publication
5
278
NADPH
P39315
mutant W139I, pH 7.5, temperature not specified in the publication
5
407
NADPH
P39315
mutant W139F, pH 7.5, temperature not specified in the publication
5
522
NADPH
P39315
wild-type, pH 7.5, temperature not specified in the publication
5
727
NADPH
P39315
mutant Y140F, pH 7.5, temperature not specified in the publication
5
Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.00046
1,4-diaminoanthraquinone-2-sulfonic acid
-
-
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
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
-
-
0.0015
1-aminoanthraquinone
-
-
0.00011
1-aminoanthraquinone-2-carboxylic acid
-
-
0.00046
1-aminoanthraquinone-2-carboxylic 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, 25C
0.08
2,4,6-trinitrotoluene
-
pH 7.0, 25C
0.0001 - 0.001
2-Heptyl-4-hydroxyquinoline-N-oxide
-
depending on enzyme solubilization
0.01
4,5,6,7-tetranitro-1,3-dihydro-2H-benzimidazol-2-one
-
pH 7.0, 25C
0.017
4,5,6-trinitro-1,3-dihydro-2H-benzimidazol-2-one
-
pH 7.0, 25C
0.02
5,6-dimethylxanthenone-4-acetic acid
-
-
0.07
5,7-dihydroxyflavone
-
-
0.08
5,7-dihydroxyflavone
-
-
0.68
5,7-dihydroxyflavone
-
-
0.00045
5-methoxy-1,2-dimethyl-3-[(4-nitrophenoxy)methyl]indole-4,7-dione
-
-
0.016
7,8-dihydroxyflavone
-
value for lysed cells
0.309
7-hydroxyflavone
-
value for lysed cells
0.000022
acid blue 25
-
-
0.05
anthraquinone
-
-
0.0013
anthraquinone-2-carboxylic acid
-
-
0.0036
anthraquinone-2-sulfonic acid
-
-
0.00012
bromoaminic acid
-
-
-
0.017
chrysin
-
value for lysed cells
0.0000062
Cibacron blue
-
-
0.00017
Cibacron blue
-
competitive vs. NADH
0.00054
Cibacron blue
-
noncompetitive vs. menadione
0.000131
dicoumarol
-
hydrophilic isoform
0.000288
dicoumarol
-
hydrophobic isoform
0.0005
dicoumarol
-
value for lysed cells
0.00095
dicoumarol
-
cofactor NADH
0.00109
dicoumarol
-
cofactor NADH
0.00412
dicoumarol
-
cofactor NADPH
0.00511
dicoumarol
-
cofactor NADPH
0.0106
dicoumarol
-
-
0.058
dicoumarol
-
cofactor NADH
0.062
dicoumarol
-
cofactor NADPH
0.05
ethyl 5-aziridin-1-yl-2,4-dinitrobenzoate
-
pH 7.0, 25C
0.075
flavone-8-acetic acid
-
-
0.0031
hydroxy(oxo)(3,6,8-trinitro-9H-carbazol-1-yl)ammonium
-
pH 7.0, 25C
1.03
isorhamnetin
-
value for lysed cells
0.0254
mitomycin C
-
-
0.0648
mitomycin C
-
-
0.0832
mitomycin C
-
-
0.04
N-methyl-N,2,4,6-tetranitroaniline
-
pH 7.0, 25C
0.06
N-methyl-N,2,4-trinitroaniline
-
pH 7.0, 25C
0.039
NADP+
-
vs. NADPH, value derived from from intercept
0.058
NADP+
-
vs. NADPH, value derived from from slope
0.077
NADP+
-
vs. 1,4-naphthoquinone, value derived from from slope
0.14
NADP+
-
vs. 1,4-naphthoquinone, value derived from intercept
0.04
nitracrine
-
pH 7.0, 25C
0.001 - 0.002
phenylmercuric acetate
-
depending on enzyme solubilization
0.000028
Procion blue M-3GS
-
-
6.19
quercetin
-
value for lysed cells
0.024
reserpine
-
-
IC50 VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.0000063
1-hydroxy-2-(1-naphthylmethyl)-3H-benzo[f]chromen-3-one
-
without bovine serum albumin, in 50 mM phosphate buffer, at pH 7.5 and 25C
0.00061
1-hydroxy-2-(1-naphthylmethyl)-3H-benzo[f]chromen-3-one
-
with 0.002 mM bovine serum albumin, in 50 mM phosphate buffer, at pH 7.5 and 25C
0.000006
1-hydroxy-2-(2-naphthylmethyl)-3H-benzo[f]chromen-3-one
-
without bovine serum albumin, in 50 mM phosphate buffer, at pH 7.5 and 25C
0.002366
1-hydroxy-2-(2-naphthylmethyl)-3H-benzo[f]chromen-3-one
-
with 0.002 mM bovine serum albumin, in 50 mM phosphate buffer, at pH 7.5 and 25C
0.025
2,2'-dimethoxy-trans-stilbene
-
above, pH not specified in the publication, 37C
-
0.0051
2,4'-dimethoxy-cis-stilbene
-
pH not specified in the publication, 37C, MCF-7 cells
0.0059
2,4'-dimethoxy-cis-stilbene
-
pH not specified in the publication, 37C, HCT-116 cells
0.0104
2,4'-dimethoxy-cis-stilbene
-
pH not specified in the publication, 37C, IMR-90 cells
0.0115
2,4'-dimethoxy-cis-stilbene
-
pH not specified in the publication, 37C
0.025
2,4'-dimethoxy-trans-stilbene
-
above, pH not specified in the publication, 37C
-
0.0023
2,4,4'-trimethoxy-cis-stilbene
-
pH not specified in the publication, 37C, HCT-116 cells
0.0025
2,4,4'-trimethoxy-cis-stilbene
-
pH not specified in the publication, 37C, MCF-7 cells
0.0056
2,4,4'-trimethoxy-cis-stilbene
-
pH not specified in the publication, 37C, IMR-90 cells
0.0081
2,4,4'-trimethoxy-cis-stilbene
-
pH not specified in the publication, 37C
0.025
2,4,4'-trimethoxy-trans-stilbene
-
above, pH not specified in the publication, 37C
-
0.0103
2,6,4'-trimethoxy-trans-stilbene
-
pH not specified in the publication, 37C
-
0.000015
2-benzyl-1-hydroxy-3H-benzo[f]chromen-3-one
-
without bovine serum albumin, in 50 mM phosphate buffer, at pH 7.5 and 25C
0.000465
2-benzyl-1-hydroxy-3H-benzo[f]chromen-3-one
-
with 0.002 mM bovine serum albumin, in 50 mM phosphate buffer, at pH 7.5 and 25C
0.025
2-hydroxy-4'-methoxy-trans-stilbene
-
above, pH not specified in the publication, 37C
-
0.00015
3,3'-(9H-fluoren-3-ylmethanediyl)bis(4-hydroxy-2H-chromen-2-one)
-
-
0.041
3,3'-(9H-fluoren-3-ylmethanediyl)bis(4-hydroxy-2H-chromen-2-one)
-
in the presence of bovine serum albumin
0.00088
3,3'-(biphenyl-4-ylmethanediyl)bis(4-hydroxy-2H-chromen-2-one)
-
-
0.0445
3,3'-(biphenyl-4-ylmethanediyl)bis(4-hydroxy-2H-chromen-2-one)
-
in the presence of bovine serum albumin
0.0013
3,3'-(furan-2-ylmethanediyl)bis(4-hydroxy-2H-chromen-2-one)
-
-
0.0059
3,3'-(furan-2-ylmethanediyl)bis(4-hydroxy-2H-chromen-2-one)
-
in the presence of bovine serum albumin
0.000014
3,3'-(naphthalen-2-ylmethanediyl)bis(4-hydroxy-2H-chromen-2-one)
-
-
0.0085
3,3'-(naphthalen-2-ylmethanediyl)bis(4-hydroxy-2H-chromen-2-one)
-
in the presence of bovine serum albumin
0.0075
3,3'-(phenylmethanediyl)bis(4,7-dihydroxy-2H-chromen-2-one)
-
-
0.082
3,3'-(phenylmethanediyl)bis(4,7-dihydroxy-2H-chromen-2-one)
-
in the presence of bovine serum albumin
0.0042
3,3'-(phenylmethanediyl)bis(4-hydroxy-2H-chromen-2-one)
-
-
0.021
3,3'-(phenylmethanediyl)bis(4-hydroxy-2H-chromen-2-one)
-
in the presence of bovine serum albumin
0.008
3,3'-(pyridin-2-ylmethanediyl)bis(4,7-dihydroxy-2H-chromen-2-one)
-
-
0.024
3,3'-(pyridin-2-ylmethanediyl)bis(4,7-dihydroxy-2H-chromen-2-one)
-
in the presence of bovine serum albumin
0.00038
3,3'-(quinolin-3-ylmethanediyl)bis(4-hydroxy-2H-chromen-2-one)
-
-
0.018
3,3'-(quinolin-3-ylmethanediyl)bis(4-hydroxy-2H-chromen-2-one)
-
in the presence of bovine serum albumin
0.00055
3,3'-(thiophen-2-ylmethanediyl)bis(4-hydroxy-2H-chromen-2-one)
-
-
0.01
3,3'-(thiophen-2-ylmethanediyl)bis(4-hydroxy-2H-chromen-2-one)
-
in the presence of bovine serum albumin
0.00035
3,3'-([4-[(E)-2-phenylethenyl]phenyl]methanediyl)bis(4-hydroxy-2H-chromen-2-one)
-
-
0.06
3,3'-([4-[(E)-2-phenylethenyl]phenyl]methanediyl)bis(4-hydroxy-2H-chromen-2-one)
-
in the presence of bovine serum albumin
0.00058
3,3'-butane-1,1-diylbis(4-hydroxy-2H-chromen-2-one)
-
without bovine serum albumin, in 50 mM phosphate buffer, at pH 7.5 and 25C
0.005322
3,3'-butane-1,1-diylbis(4-hydroxy-2H-chromen-2-one)
-
with 0.002 mM bovine serum albumin, in 50 mM phosphate buffer, at pH 7.5 and 25C
0.000005
3,3'-methanediylbis(4,7-dihydroxy-2H-chromen-2-one)
-
-
0.00035
3,3'-methanediylbis(4,7-dihydroxy-2H-chromen-2-one)
-
in the presence of bovine serum albumin
0.00000018
3,3'-methanediylbis(4-hydroxy-2H-benzo[h]chromen-2-one)
-
with 0.002 mM bovine serum albumin, in 50 mM phosphate buffer, at pH 7.5 and 25C
0.00037
3,3'-methanediylbis(4-hydroxy-2H-benzo[h]chromen-2-one)
-
with 0.002 mM bovine serum albumin, in 50 mM phosphate buffer, at pH 7.5 and 25C
0.0000026
3,3'-methanediylbis(4-hydroxy-2H-chromen-2-one)
-
without bovine serum albumin, at pH 7.5, 25C
0.000404
3,3'-methanediylbis(4-hydroxy-2H-chromen-2-one)
-
with 0.14% (v/v) bovine serum albumin, at pH 7.5, 25C
0.0000028
3,3'-methanediylbis(4-hydroxy-5-methoxy-2H-chromen-2-one)
-
without bovine serum albumin, at pH 7.5, 25C
0.0000028
3,3'-methanediylbis(4-hydroxy-5-methoxy-2H-chromen-2-one)
-
without bovine serum albumin, in 50 mM phosphate buffer, at pH 7.5 and 25C
0.000038
3,3'-methanediylbis(4-hydroxy-5-methoxy-2H-chromen-2-one)
-
with 0.14% (v/v) bovine serum albumin, at pH 7.5, 25C
0.000038
3,3'-methanediylbis(4-hydroxy-5-methoxy-2H-chromen-2-one)
-
with 0.002 mM bovine serum albumin, in 50 mM phosphate buffer, at pH 7.5 and 25C
0.000062
3,3'-methanediylbis(4-hydroxy-6,7-dimethoxy-2H-chromen-2-one)
-
without bovine serum albumin, at pH 7.5, 25C
0.000062
3,3'-methanediylbis(4-hydroxy-6,7-dimethoxy-2H-chromen-2-one)
-
without bovine serum albumin, in 50 mM phosphate buffer, at pH 7.5 and 25C
0.001497
3,3'-methanediylbis(4-hydroxy-6,7-dimethoxy-2H-chromen-2-one)
-
with 0.14% (v/v) bovine serum albumin, at pH 7.5, 25C
0.001497
3,3'-methanediylbis(4-hydroxy-6,7-dimethoxy-2H-chromen-2-one)
-
with 0.002 mM bovine serum albumin, in 50 mM phosphate buffer, at pH 7.5 and 25C
0.00000041
3,3'-methanediylbis(4-hydroxy-6,7-dimethyl-2H-chromen-2-one)
-
without bovine serum albumin, at pH 7.5, 25C
0.00000041
3,3'-methanediylbis(4-hydroxy-6,7-dimethyl-2H-chromen-2-one)
-
without bovine serum albumin, in 50 mM phosphate buffer, at pH 7.5 and 25C
0.000233
3,3'-methanediylbis(4-hydroxy-6,7-dimethyl-2H-chromen-2-one)
-
with 0.14% (v/v) bovine serum albumin, at pH 7.5, 25C
0.000233
3,3'-methanediylbis(4-hydroxy-6,7-dimethyl-2H-chromen-2-one)
-
with 0.002 mM bovine serum albumin, in 50 mM phosphate buffer, at pH 7.5 and 25C
0.0000049
3,3'-methanediylbis(4-hydroxy-6,8-dibromo-2H-chromen-2-one)
-
without bovine serum albumin, in 50 mM phosphate buffer, at pH 7.5 and 25C
0.063
3,3'-methanediylbis(4-hydroxy-6,8-dibromo-2H-chromen-2-one)
-
with 0.002 mM bovine serum albumin, in 50 mM phosphate buffer, at pH 7.5 and 25C
0.000009
3,3'-methanediylbis(4-hydroxy-6-chloro-2H-chromen-2-one)
-
without bovine serum albumin, in 50 mM phosphate buffer, at pH 7.5 and 25C
0.00625
3,3'-methanediylbis(4-hydroxy-6-chloro-2H-chromen-2-one)
-
with 0.002 mM bovine serum albumin, in 50 mM phosphate buffer, at pH 7.5 and 25C
0.0000045
3,3'-methanediylbis(4-hydroxy-6-fluoro-2H-chromen-2-one)
-
without bovine serum albumin, in 50 mM phosphate buffer, at pH 7.5 and 25C
0.0016
3,3'-methanediylbis(4-hydroxy-6-fluoro-2H-chromen-2-one)
-
with 0.002 mM bovine serum albumin, in 50 mM phosphate buffer, at pH 7.5 and 25C
0.000011
3,3'-methanediylbis(4-hydroxy-6-methoxy-2H-chromen-2-one)
-
without bovine serum albumin, at pH 7.5, 25C
0.000011
3,3'-methanediylbis(4-hydroxy-6-methoxy-2H-chromen-2-one)
-
without bovine serum albumin, in 50 mM phosphate buffer, at pH 7.5 and 25C
0.0033
3,3'-methanediylbis(4-hydroxy-6-methoxy-2H-chromen-2-one)
-
with 0.14% (v/v) bovine serum albumin, at pH 7.5, 25C
0.0033
3,3'-methanediylbis(4-hydroxy-6-methoxy-2H-chromen-2-one)
-
with 0.002 mM bovine serum albumin, in 50 mM phosphate buffer, at pH 7.5 and 25C
0.00000042
3,3'-methanediylbis(4-hydroxy-7,8-dimethyl-2H-chromen-2-one)
-
without bovine serum albumin, at pH 7.5, 25C
0.00000042
3,3'-methanediylbis(4-hydroxy-7,8-dimethyl-2H-chromen-2-one)
-
without bovine serum albumin, in 50 mM phosphate buffer, at pH 7.5 and 25C
0.000096
3,3'-methanediylbis(4-hydroxy-7,8-dimethyl-2H-chromen-2-one)
-
with 0.002 mM bovine serum albumin, in 50 mM phosphate buffer, at pH 7.5 and 25C
0.000149
3,3'-methanediylbis(4-hydroxy-7,8-dimethyl-2H-chromen-2-one)
-
with 0.14% (v/v) bovine serum albumin, at pH 7.5, 25C
0.0000038
3,3'-methanediylbis(4-hydroxy-7-fluoro-2H-chromen-2-one)
-
without bovine serum albumin, in 50 mM phosphate buffer, at pH 7.5 and 25C
0.00115
3,3'-methanediylbis(4-hydroxy-7-fluoro-2H-chromen-2-one)
-
with 0.002 mM bovine serum albumin, in 50 mM phosphate buffer, at pH 7.5 and 25C
0.000006
3,3'-methanediylbis(4-hydroxy-7-methoxy-2H-chromen-2-one)
-
without bovine serum albumin, at pH 7.5, 25C
0.000006
3,3'-methanediylbis(4-hydroxy-7-methoxy-2H-chromen-2-one)
-
without bovine serum albumin, in 50 mM phosphate buffer, at pH 7.5 and 25C
0.00079
3,3'-methanediylbis(4-hydroxy-7-methoxy-2H-chromen-2-one)
-
with 0.14% (v/v) bovine serum albumin, at pH 7.5, 25C
0.00079
3,3'-methanediylbis(4-hydroxy-7-methoxy-2H-chromen-2-one)
-
with 0.002 mM bovine serum albumin, in 50 mM phosphate buffer, at pH 7.5 and 25C
0.000014
3,3'-methylenebis(4-hydroxy-6-methyl-2H-chromen-2-one)
-
without bovine serum albumin, in 50 mM phosphate buffer, at pH 7.5 and 25C
0.0055
3,3'-methylenebis(4-hydroxy-6-methyl-2H-chromen-2-one)
-
with 0.002 mM bovine serum albumin, in 50 mM phosphate buffer, at pH 7.5 and 25C
0.0022
3,3'-[(4-chlorophenyl)methanediyl]bis(4-hydroxy-2H-chromen-2-one)
-
-
0.028
3,3'-[(4-chlorophenyl)methanediyl]bis(4-hydroxy-2H-chromen-2-one)
-
in the presence of bovine serum albumin
0.00065
3,3'-[(4-hydroxy-3-methoxyphenyl)methanediyl]bis(4-hydroxy-2H-chromen-2-one)
-
-
0.01
3,3'-[(4-hydroxy-3-methoxyphenyl)methanediyl]bis(4-hydroxy-2H-chromen-2-one)
-
in the presence of bovine serum albumin
0.0023
3,3'-[(4-hydroxyphenyl)methanediyl]bis(4-hydroxy-2H-chromen-2-one)
-
-
0.035
3,3'-[(4-hydroxyphenyl)methanediyl]bis(4-hydroxy-2H-chromen-2-one)
-
in the presence of bovine serum albumin
0.00022
3,3'-[(4-methoxyphenyl)methanediyl]bis(4-hydroxy-2H-chromen-2-one)
-
-
0.0087
3,3'-[(4-methoxyphenyl)methanediyl]bis(4-hydroxy-2H-chromen-2-one)
-
in the presence of bovine serum albumin
0.00125
3,3'-[[3,5-bis(benzyloxy)phenyl]methanediyl]bis(4-hydroxy-2H-chromen-2-one)
-
-
0.05
3,3'-[[3,5-bis(benzyloxy)phenyl]methanediyl]bis(4-hydroxy-2H-chromen-2-one)
-
in the presence of bovine serum albumin
0.00035
3,3'-[[4-(1-methylethyl)phenyl]methanediyl]bis(4-hydroxy-2H-chromen-2-one)
-
-
0.0029
3,3'-[[4-(1-methylethyl)phenyl]methanediyl]bis(4-hydroxy-2H-chromen-2-one)
-
in the presence of bovine serum albumin
0.0001
3,3'-[[4-(dimethylamino)phenyl]methanediyl]bis(4-hydroxy-2H-chromen-2-one)
-
-
0.005
3,3'-[[4-(dimethylamino)phenyl]methanediyl]bis(4-hydroxy-2H-chromen-2-one)
-
in the presence of bovine serum albumin
0.0044
3,4'-dimethoxy-cis-stilbene
-
pH not specified in the publication, 37C, MCF-7 cells
0.0051
3,4'-dimethoxy-cis-stilbene
-
pH not specified in the publication, 37C, HCT-116 cells
0.0095
3,4'-dimethoxy-cis-stilbene
-
pH not specified in the publication, 37C, IMR-90 cells
0.0097
3,4'-dimethoxy-cis-stilbene
-
pH not specified in the publication, 37C
0.025
3,4'-dimethoxy-trans-stilbene
-
above, pH not specified in the publication, 37C
-
0.0023
3,4,4'-trimethoxy-cis-stilbene
-
pH not specified in the publication, 37C, HCT-116 cells
0.0024
3,4,4'-trimethoxy-cis-stilbene
-
pH not specified in the publication, 37C, MCF-7 cells
0.0051
3,4,4'-trimethoxy-cis-stilbene
-
pH not specified in the publication, 37C
0.007
3,4,4'-trimethoxy-cis-stilbene
-
pH not specified in the publication, 37C, IMR-90 cells
0.025
3,4,4'-trimethoxy-trans-stilbene
-
above, pH not specified in the publication, 37C
-
0.000015
3,4,5,4'-tetramethoxy-cis-stilbene
-
pH not specified in the publication, 37C, MCF-7 cells
0.00002
3,4,5,4'-tetramethoxy-cis-stilbene
-
pH not specified in the publication, 37C, HCT-116 cells; pH not specified in the publication, 37C, IMR-90 cells
0.000034
3,4,5,4'-tetramethoxy-cis-stilbene
-
pH not specified in the publication, 37C
0.00016
3,4,5,4'-tetramethoxy-trans-stilbene
-
pH not specified in the publication, 37C, IMR-90 cells
0.00022
3,4,5,4'-tetramethoxy-trans-stilbene
-
pH not specified in the publication, 37C, MCF-7 cells
0.00053
3,4,5,4'-tetramethoxy-trans-stilbene
-
pH not specified in the publication, 37C, HCT-116 cells
0.001
3,4,5,4'-tetramethoxy-trans-stilbene
-
pH not specified in the publication, 37C
0.00012
3,5,4'-trimethoxy-cis-stilbene
-
pH not specified in the publication, 37C, MCF-7 cells
0.00022
3,5,4'-trimethoxy-cis-stilbene
-
pH not specified in the publication, 37C, HCT-116 cells
0.00023
3,5,4'-trimethoxy-cis-stilbene
-
pH not specified in the publication, 37C, IMR-90 cells
0.00059
3,5,4'-trimethoxy-cis-stilbene
-
pH not specified in the publication, 37C
0.0011
3,5,4'-trimethoxy-trans-stilbene
-
pH not specified in the publication, 37C, MCF-7 cells
-
0.0021
3,5,4'-trimethoxy-trans-stilbene
-
pH not specified in the publication, 37C, IMR-90 cells
-
0.0052
3,5,4'-trimethoxy-trans-stilbene
-
pH not specified in the publication, 37C
-
0.0057
3,5,4'-trimethoxy-trans-stilbene
-
pH not specified in the publication, 37C, HCT-116 cells
-
0.025
3,5-dihydroxy-4'-methoxy-cis-stilbene, 3,5-dihydroxy-4'-methoxy-trans-stilbene
-
above, pH not specified in the publication, 37C
-
0.000255
3-(2,4-difluorophenoxymethyl)-6-methoxy-1,2-dimethylindole-4,7-dione
-
-
0.004654
3-(2-fluoro-4-nitrophenoxymethyl)-5-methoxy-1,2-dimethylindole-4,7-dione
-
-
0.000529
3-(2-fluoro-4-nitrophenoxymethyl)-6-methoxy-1,2-dimethylindole-4,7-dione
-
-
0.000031
3-(3,4-dimethylbenzyl)-4-hydroxy-2H-chromen-2-one
-
without bovine serum albumin, in 50 mM phosphate buffer, at pH 7.5 and 25C
0.0016
3-(3,4-dimethylbenzyl)-4-hydroxy-2H-chromen-2-one
-
with 0.002 mM bovine serum albumin, in 50 mM phosphate buffer, at pH 7.5 and 25C
0.0000099
3-(3,4-dimethylbenzyl)-4-hydroxy-6,7-dimethyl-2H-chromen-2-one
-
without bovine serum albumin, at pH 7.5, 25C
0.0000099
3-(3,4-dimethylbenzyl)-4-hydroxy-6,7-dimethyl-2H-chromen-2-one
-
without bovine serum albumin, in 50 mM phosphate buffer, at pH 7.5 and 25C
0.000192
3-(3,4-dimethylbenzyl)-4-hydroxy-6,7-dimethyl-2H-chromen-2-one
-
with 0.14% (v/v) bovine serum albumin, at pH 7.5, 25C
0.000192
3-(3,4-dimethylbenzyl)-4-hydroxy-6,7-dimethyl-2H-chromen-2-one
-
with 0.002 mM bovine serum albumin, in 50 mM phosphate buffer, at pH 7.5 and 25C
0.000504
3-(4-aminophenoxymethyl)-6-methoxy-1,2-dimethylindole-4,7-dione
-
-
0.000463
3-(4-cyanophenoxymethyl)-6-methoxy-1,2-dimethylindole-4,7-dione
-
-
0.000905
3-(4-fluorophenoxymethyl)-6-methoxy-1,2-dimethylindole-4,7-dione
-
-
0.000035
3-benzyl-4-hydroxy-2H-benzo[h]chromen-2-one
-
without bovine serum albumin, in 50 mM phosphate buffer, at pH 7.5 and 25C
0.00088
3-benzyl-4-hydroxy-2H-benzo[h]chromen-2-one
-
with 0.002 mM bovine serum albumin, in 50 mM phosphate buffer, at pH 7.5 and 25C
0.000144
3-benzyl-4-hydroxy-2H-chromen-2-one
-
without bovine serum albumin, in 50 mM phosphate buffer, at pH 7.5 and 25C
0.0032
3-benzyl-4-hydroxy-2H-chromen-2-one
-
with 0.002 mM bovine serum albumin, in 50 mM phosphate buffer, at pH 7.5 and 25C
0.000039
3-benzyl-4-hydroxy-6,7-dimethyl-2H-chromen-2-one
-
without bovine serum albumin, in 50 mM phosphate buffer, at pH 7.5 and 25C
0.00066
3-benzyl-4-hydroxy-6,7-dimethyl-2H-chromen-2-one
-
with 0.002 mM bovine serum albumin, in 50 mM phosphate buffer, at pH 7.5 and 25C
0.025
3-hydroxy-4'-methoxy-cis-stilbene, 3-hydroxy-4'-methoxy-trans-stilbene
-
above, pH not specified in the publication, 37C
-
0.0034
3-hydroxy-4,4'-dimethoxy-cis-stilbene
-
pH not specified in the publication, 37C, HCT-116 cells
0.0042
3-hydroxy-4,4'-dimethoxy-cis-stilbene
-
pH not specified in the publication, 37C, MCF-7 cells
0.006
3-hydroxy-4,4'-dimethoxy-cis-stilbene
-
pH not specified in the publication, 37C, IMR-90 cells
0.025
3-hydroxy-4,4'-dimethoxy-cis-stilbene
-
above, pH not specified in the publication, 37C
0.025
3-hydroxy-4,4'-dimethoxy-trans-stilbene
-
above, pH not specified in the publication, 37C
-
0.002475
3-methoxy-1,2-dimethyl-3-(3-pyridyloxymethyl)indole-4,7-dione
-
-
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
-
-
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
-
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
-
-
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
-
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
-
-
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
-
in the presence of bovine serum albumin
0.025
4,4'-dimethoxy-cis-stilbene, 4,4'-dimethoxy-trans-stilbene
-
above, pH not specified in the publication, 37C
-
0.00325
4-amino-2H-chromen-2-one
-
-
0.013
4-amino-2H-chromen-2-one
-
in the presence of bovine serum albumin
0.0000063
4-hydroxy-3-(1-naphthylmethyl)-2H-benzo[h]chromen-2-one
-
without bovine serum albumin, in 50 mM phosphate buffer, at pH 7.5 and 25C
0.00045
4-hydroxy-3-(1-naphthylmethyl)-2H-benzo[h]chromen-2-one
-
with 0.002 mM bovine serum albumin, in 50 mM phosphate buffer, at pH 7.5 and 25C
0.000024
4-hydroxy-3-(1-naphthylmethyl)-2H-chromen-2-one
-
without bovine serum albumin, in 50 mM phosphate buffer, at pH 7.5 and 25C
0.001522
4-hydroxy-3-(1-naphthylmethyl)-2H-chromen-2-one
-
with 0.002 mM bovine serum albumin, in 50 mM phosphate buffer, at pH 7.5 and 25C
0.0000022
4-hydroxy-3-(2-naphthylmethyl)-2H-benzo[h]chromen-2-one
-
without bovine serum albumin, in 50 mM phosphate buffer, at pH 7.5 and 25C
0.000255
4-hydroxy-3-(2-naphthylmethyl)-2H-benzo[h]chromen-2-one
-
with 0.002 mM bovine serum albumin, in 50 mM phosphate buffer, at pH 7.5 and 25C
0.000014
4-hydroxy-3-(2-naphthylmethyl)-2H-chromen-2-one
-
without bovine serum albumin, in 50 mM phosphate buffer, at pH 7.5 and 25C
0.001452
4-hydroxy-3-(2-naphthylmethyl)-2H-chromen-2-one
-
with 0.002 mM bovine serum albumin, in 50 mM phosphate buffer, at pH 7.5 and 25C
0.0000063
4-hydroxy-3-(naphthalen-1-yl)cyclohepta[h]chromen-2(7H)-one
-
without bovine serum albumin, at pH 7.5, 25C
0.00045
4-hydroxy-3-(naphthalen-1-yl)cyclohepta[h]chromen-2(7H)-one
-
with 0.14% (v/v) bovine serum albumin, at pH 7.5, 25C
0.0000022
4-hydroxy-3-(naphthalen-2-yl)cyclohepta[h]chromen-2(7H)-one
-
without bovine serum albumin, at pH 7.5, 25C
0.000225
4-hydroxy-3-(naphthalen-2-yl)cyclohepta[h]chromen-2(7H)-one
-
with 0.14% (v/v) bovine serum albumin, at pH 7.5, 25C
0.000035
4-hydroxy-3-phenylcyclohepta[h]chromen-2(7H)-one
-
without bovine serum albumin, at pH 7.5, 25C
0.00088
4-hydroxy-3-phenylcyclohepta[h]chromen-2(7H)-one
-
with 0.14% (v/v) bovine serum albumin, at pH 7.5, 25C
0.0000077
4-hydroxy-6,7-dimethyl-3-(1-naphthylmethyl)-2H-chromen-2-one
-
without bovine serum albumin, in 50 mM phosphate buffer, at pH 7.5 and 25C
0.001095
4-hydroxy-6,7-dimethyl-3-(1-naphthylmethyl)-2H-chromen-2-one
-
with 0.002 mM bovine serum albumin, in 50 mM phosphate buffer, at pH 7.5 and 25C
0.0000025
4-hydroxy-6,7-dimethyl-3-(2-naphthylmethyl)-2H-chromen-2-one
-
without bovine serum albumin, in 50 mM phosphate buffer, at pH 7.5 and 25C
0.000167
4-hydroxy-6,7-dimethyl-3-(2-naphthylmethyl)-2H-chromen-2-one
-
with 0.002 mM bovine serum albumin, in 50 mM phosphate buffer, at pH 7.5 and 25C
0.0000077
4-hydroxy-6,7-dimethyl-3-(naphthalen-1-yl)-2H-chromen-2-one
-
without bovine serum albumin, at pH 7.5, 25C
0.001095
4-hydroxy-6,7-dimethyl-3-(naphthalen-1-yl)-2H-chromen-2-one
-
with 0.14% (v/v) bovine serum albumin, at pH 7.5, 25C
0.0000025
4-hydroxy-6,7-dimethyl-3-(naphthalen-2-yl)-2H-chromen-2-one
-
without bovine serum albumin, at pH 7.5, 25C
0.000167
4-hydroxy-6,7-dimethyl-3-(naphthalen-2-yl)-2H-chromen-2-one
-
with 0.14% (v/v) bovine serum albumin, at pH 7.5, 25C
0.000039
4-hydroxy-6,7-dimethyl-3-phenyl-2H-chromen-2-one
-
without bovine serum albumin, at pH 7.5, 25C
0.00066
4-hydroxy-6,7-dimethyl-3-phenyl-2H-chromen-2-one
-
with 0.14% (v/v) bovine serum albumin, at pH 7.5, 25C
0.0017
4-[bis(4-hydroxy-2-oxo-2H-chromen-3-yl)methyl]benzoic acid
-
-
0.021
4-[bis(4-hydroxy-2-oxo-2H-chromen-3-yl)methyl]benzoic acid
-
in the presence of bovine serum albumin
0.000427
5-methoxy-1,2-dimethyl-3-(2,4,6-trifluorophenoxymethyl)indole-4,7-dione
-
-
0.000345
5-methoxy-1,2-dimethyl-3-(2-nitrophenoxymethyl)indole-4,7-dione
-
-
0.000352
5-methoxy-1,2-dimethyl-3-(3-nitrophenoxymethyl)indole-4,7-dione
-
-
0.000904
5-methoxy-1,2-dimethyl-3-(3-pyridyloxymethyl)indole-4,7-dione
-
-
0.000629
5-methoxy-1,2-dimethyl-3-(4-nitrophenoxymethyl)indole-4,7-dione
-
-
0.001385
5-methoxy-1,2-dimethyl-3-(phenoxymethyl)indole-4,7-dione
-
-
0.002007
5-methoxy-1,2-dimethyl-3-(pyridin-4-yloxymethyl)indole-4,7-dione
-
-
0.001829
5-methoxy-1,2-dimethyl-3-[1-(4-nitrophenoxy)ethyl]indole-4,7-dione
-
-
0.000452
6-methoxy-1,2-dimethyl-3-(2,4,6-trifluorophenoxymethyl)indole-4,7-dione
-
-
0.000363
6-methoxy-1,2-dimethyl-3-(2-nitrophenoxymethyl)indole-4,7-dione
-
-
0.000351
6-methoxy-1,2-dimethyl-3-(3-nitrophenoxymethyl)indole-4,7-dione
-
-
0.000638
6-methoxy-1,2-dimethyl-3-(4-nitrophenoxymethyl)indole-4,7-dione
-
-
0.004563
6-methoxy-1,2-dimethyl-3-(phenoxymethyl)indole-4,7-dione
-
-
0.009579
6-methoxy-1,2-dimethyl-3-(pyridin-2-yloxymethyl)indole-4,7-dione
-
-
0.00256
6-methoxy-1,2-dimethyl-3-(pyridin-4-yloxymethyl)indole-4,7-dione
-
-
0.000496
6-methoxy-1,2-dimethyl-3-[4-(trifluoromethyl)phenoxymethyl]-indole-4,7-dione
-
-
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
-
-
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
-
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
-
-
0.00065
7-(4-hydroxy-2-oxo-2H-chromen-3-yl)-6H,7H-chromeno[4,3-b]chromen-6-one
-
in the presence of bovine serum albumin
1
alpha,alpha'-dipyridyl
-
IC50: 1 mM
0.0000026
dicoumarol
-
without bovine serum albumin, in 50 mM phosphate buffer, at pH 7.5 and 25C
0.000005
dicoumarol
-
without bovine serum albumin
0.000404
dicoumarol
-
with 0.002 mM bovine serum albumin, in 50 mM phosphate buffer, at pH 7.5 and 25C
0.00045
dicoumarol
-
in the presence of bovine serum albumin
0.001221
ethyl bis(4-hydroxy-2-oxo-2H-chromen-3-yl)acetate
-
without bovine serum albumin, in 50 mM phosphate buffer, at pH 7.5 and 25C
0.02233
ethyl bis(4-hydroxy-2-oxo-2H-chromen-3-yl)acetate
-
with 0.002 mM bovine serum albumin, in 50 mM phosphate buffer, at pH 7.5 and 25C
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
0.0000199
-
in total leucocytes
0.0000239
-
in lymphocytes
0.000072
-
in rectal biopsies of the C609T genotype
0.00011
-
in rectal biopsies of the C609C genotype
0.00022
-
48 h after after oral administration of vitamin E
0.00023
-
control, 24 h
0.00024
-
24 h after after oral administration of vitamin E; 48 h after oral administration of manganese; control, 24 h
0.00025
-
48 h after oral administration of cadmium and vitamin E
0.00026
-
48 h after after oral administration of cadmium
0.00055
-
24 h after oral administration of manganese
0.00056
-
24 h after oral administration of cadmium and vitamin E
0.00059
-
24 h after after oral administration of cadmium
0.001
-
below, recombinant enzyme NQO1, substrate 10a, pH not specified in the publication, 37C; below, recombinant enzyme NQO1, substrate 10f, pH not specified in the publication, 37C; below, recombinant enzyme NQO1, substrate 10g, pH not specified in the publication, 37C; below, recombinant enzyme NQO1, substrate 10h, pH not specified in the publication, 37C; below, recombinant enzyme NQO1, substrate 10o, pH not specified in the publication, 37C; below, recombinant enzyme NQO1, substrate 11d, pH not specified in the publication, 37C; below, recombinant enzyme NQO1, substrate 11e, pH not specified in the publication, 37C; below, recombinant enzyme NQO1, substrate 11h, pH not specified in the publication, 37C; below, recombinant enzyme NQO1, substrate 11i, pH not specified in the publication, 37C; below, recombinant enzyme NQO1, substrate 11k, pH not specified in the publication, 37C; below, recombinant enzyme NQO1, substrate 11l, pH not specified in the publication, 37C
0.0014
-
recombinant enzyme NQO1, substrate 10k, pH not specified in the publication, 37C
0.0062
-
recombinant enzyme NQO1, substrate 5-(aziridin-1-yl)-2,4-dinitrobenzamide, i.e. CB-1954, pH not specified in the publication, 37C
0.011
-
recombinant enzyme NQO1, substrate 10c, pH not specified in the publication, 37C
0.013
-
recombinant enzyme NQO1, substrate 2-(3,5-dinitropyridin-2-yl)-1,2,3,4-tetrahydroisoquinoline, pH not specified in the publication, 37C
0.016
-
recombinant enzyme NQO1, substrate 11a, pH not specified in the publication, 37C
0.02
-
recombinant enzyme NQO1, substrate 10n, pH not specified in the publication, 37C
0.038
-
recombinant enzyme NQO1, substrate 10j, pH not specified in the publication, 37C
0.039
-
activity in liver microsomes, reduction of menadione, cofactor NADPH
0.041
-
activity in liver cytosol, reduction of menadione, cofactor NADH
0.042
-
recombinant enzyme NQO1, substrate 10e, pH not specified in the publication, 37C
0.05
-
in lung of control rats
0.051
-
activity in liver cytosol, reduction of menadione, cofactor NADPH
0.053
-
recombinant enzyme NQO1, substrate 10d, pH not specified in the publication, 37C
0.06
-
in lung of rats treated with 0.4 or 4 mg/kg of 3-nitrobenzanthrone
0.076
-
recombinant enzyme NQO1, substrate 10m, pH not specified in the publication, 37C
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, 37C
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, 37C
0.23
-
in kidney of rats treated with 40 mg/kg of 3-nitrobenzanthrone
0.63
-
activity in liver microsomes, reduction of 2,6-dichlorophenolindophenol, cofactor NADH
3.5
-
with FMN as substrate
4
-
menadione-cytochrome c reduction assay
8.1
-
with ferricyanide and FAD as substrates
35.3
-
with menadione and FAD as substrates
50
P0A8G6
substrate [Fe(CN)6]3-, pH 7.2, 37C
160
P0A8G6
substrate 2,6-dichlorophenolindophenol, pH 7.2, 37C
179.1
-
with ferricyanide and FMN as substrates
430
P0A8G6
substrate menadione, pH 7.2, 37C
435.3
-
recombinant enzyme
505
-
isoform III, towards menadione
560
P0A8G6
substrate 1,4-naphthoquinone, pH 7.2, 37C
634
-
isoform IV, towards menadione
710
-
cytosol
800
-
purified enzyme
830
-
microsomes
911.4
-
with menadione and FMN as substrates
930
P0A8G6
substrate 2,3-dihydroxy-5-methyl-1,4-benzoquinone, pH 7.2, 37C
990
P0A8G6
substrate 1,4-benzoquinone, pH 7.2, 37C
1129
-
isoform VII, towards menadione
1186
-
isoform V, towards menadione
1212
-
dichloroindophenol
1300
P58795
substrate menadione, pH 7.2, 37C
1400
P58795
substrate 2,6-dichlorophenolindophenol, pH 7.2, 37C; substrate [Fe(CN)6]3-, pH 7.2, 37C
1720
-
hydrophilic isoform
1770
-
hydrophobic isoform
2228
-
isoform II, towards menadione
2452
-
2-methyl-1,4-naphthoquinone
2459
-
isoform VIb, towards menadione
2469
-
-
5860
-
isoform VIa, towards menadione
6700
P58795
substrate 2,3-dihydroxy-5-methyl-1,4-benzoquinone, pH 7.2, 37C
8900
P58795
substrate 1,4-naphthoquinone, pH 7.2, 37C
25000
P58795
substrate 1,4-benzoquinone, pH 7.2, 37C
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
-
-
additional information
-
quinone or quinone-like compounds reduction assay with a specific activity ranging from 0.92-4.6 U/mg of protein
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
4.4
-
plateau region from pH 6.0-7.5 with 70% activity
5
-
chromate reductase activity
5.7
-
menadione
7 - 8.5
-
-
7 - 8.8
-
-
7.1
-
assay at
7.4
-
assay at
7.4
-
assay at
7.5 - 8.5
-
quinone reductase activity
7.5
-
60% activity at pH 9.0
7.5
Q5EI63
assay at
7.5
-
assay at
8
-
2-methoxy-5-(methoxymethyl)-2,5-cyclohexadiene
8.5
-
2-hydroxymethyl-5-methoxy-2,5-cyclohexadiene-1,4-dione
9.7
-
decrease above
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
4.8 - 9.8
-
-
5 - 8.5
P58795
more than 95% of maximum activity within this range
5 - 9
-
pH 5.0: about 45% of maximal activity, pH 9.0: about 55% of maximal activity
5 - 9.5
-
-
5.5 - 7.5
-
the enzyme maintains greater than 90% of its maximal activity between pH 5.5 and 7.5
5.5 - 9
-
reduction of 2,6-dimethoxybenzoquinone
6 - 10.2
-
inactive above or below
6 - 8
P0A8G6
more than 95% of maximum activity within this range
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
22 - 26
-
assay at
23
-
assay at room temperature
25
-
assay at
25
Q5EI63
assay at
27
-
assay at
30 - 43
-
decrease above
37
-
assay at
37
-
assay at
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
Manually annotated by BRENDA team
-
pulmonary arterial endothelial cell. Increase in enzyme protein and activity upon hyperoxia, i.e. exposure to 95% O2 for 48 h
Manually annotated by BRENDA team
-
enzyme is highly upregulated in active and chronic multiple sclerosis lesions, particularly in hypertrophic astrocytes and myelin-laden macrophages
Manually annotated by BRENDA team
-
wild-type p53immortalized B-cell lymphoblasts from individuals with heterozygous NQO1; homozygous NQO1+/- and missing NQO1, LBL51
Manually annotated by BRENDA team
-
the ratio of frontal to cerebellar NQO1 activity is significantly increased in patients with Alzheimers disease versus controls, specific localization to astrocytes and neurites surrounding senile plaques. Neuronal NQO1 staining seen in frontal cortex of Alzheimers disease patients is absent in frontal cortex of controls, but is found to the same extent in neurons of the substantia nigra of both Alzheimers disease patients and controls
Manually annotated by BRENDA team
-
H2O2-scavenging and growth of wild-type, overexpressing, and knockout cells, overview
Manually annotated by BRENDA team
-
the ratio of frontal to cerebellar NQO1 activity is significantly increased in patients with Alzheimers disease versus controls
Manually annotated by BRENDA team
-
the ratio of frontal to cerebellar NQO1 activity is significantly increased in patients with Alzheimers disease versus controls
Manually annotated by BRENDA team
P15559
NQO1-deficient BE and NQO1-rich BE-NQ
Manually annotated by BRENDA team
P15559
BE human colon adenocarcinoma cells, stably NQO1-transfected BE-NQ cells69
Manually annotated by BRENDA team
-
recombinant human NQO1
Manually annotated by BRENDA team
-
pulmonary arterial, sulforaphane-treated
Manually annotated by BRENDA team
-
pulmonary arterial endothelial cell. Increase in enzyme protein and activity upon hyperoxia, i.e. exposure to 95% O2 for 48 h
Manually annotated by BRENDA team
Q5EI63
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
Manually annotated by BRENDA team
Mus musculus C3H
-
-
-
Manually annotated by BRENDA team
-
bovine leukemia virus-transformed lamb kidney fibroblast cell line
Manually annotated by BRENDA team
-
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
Manually annotated by BRENDA team
-
up-regulation of enzyme upon exposure to L-dopa and tetrahydropapaveroline
Manually annotated by BRENDA team
Hevea brasiliensis Mull.-Arg.
-
-
-
Manually annotated by BRENDA team
-
for genotyping
Manually annotated by BRENDA team
-
no correlation between NQO1 activity in rectal biopsies and NQO1 activity in total leukocytes. No correlation between total leukocyte and lymphocyte NQO1 activity
Manually annotated by BRENDA team
Xenopus laevis, Tinca vulgaris
-
-
Manually annotated by BRENDA team
P15559
traces
Manually annotated by BRENDA team
-
patients with liver damage due to acetaminophen overdose or primary biliary cirrhosis
Manually annotated by BRENDA team
-
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
Manually annotated by BRENDA team
-
no correlation between NQO1 activity in rectal biopsies and NQO1 activity in total lymphocytes. No correlation between total leukocyte and lymphocyte NQO1 activity
Manually annotated by BRENDA team
-
enzyme is highly upregulated in active and chronic multiple sclerosis lesions, particularly in hypertrophic astrocytes and myelin-laden macrophages
Manually annotated by BRENDA team
-
wild-type p53 breast cancer cell lines MCF7 transfected with MCF7-NQO1 to overexpress NQO1, MCF7-SUP8 to knockdown NQO1
Manually annotated by BRENDA team
-
human breast cancer cell line lacking enzyme due to genetic polymorphism
Manually annotated by BRENDA team
Sporotrichum pulverulentum
-
-
Manually annotated by BRENDA team
-
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.
Manually annotated by BRENDA team
-
pancreatic tissues from smokers and pancreatic adenocarcinomas
Manually annotated by BRENDA team
-
upregulation or overexpression of the enzyme in tumours
Manually annotated by BRENDA team
-
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
Manually annotated by BRENDA team
-
p53 mutant MDA-MB-157 and MDAMB-231, dominant negative p53
Manually annotated by BRENDA team
-
human pancreatic carcinoma cells
Manually annotated by BRENDA team
additional information
P15559
no expression in erythrocytes
Manually annotated by BRENDA team
additional information
-
lung epithelial cancer cell
Manually annotated by BRENDA team
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
Manually annotated by BRENDA team
additional information
-
the enzyme is present in a wide range of tissue and cell types including the pulmonary endothelium and other lung cells
Manually annotated by BRENDA team
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY
GeneOntology No.
LITERATURE
SOURCE
Sporotrichum pulverulentum
-
-
Manually annotated by BRENDA team
-
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
Manually annotated by BRENDA team
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
-
Manually annotated by BRENDA team
PDB
SCOP
CATH
ORGANISM
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)
Escherichia coli (strain K12)
Escherichia coli (strain K12)
Escherichia coli (strain K12)
Escherichia coli (strain K12)
Escherichia coli (strain K12)
Escherichia coli (strain K12)
Escherichia coli (strain K12)
Escherichia coli (strain K12)
Escherichia coli (strain K12)
Escherichia coli (strain K12)
Pseudomonas aeruginosa (strain ATCC 15692 / PAO1 / 1C / PRS 101 / LMG 12228)
Pseudomonas aeruginosa (strain ATCC 15692 / PAO1 / 1C / PRS 101 / LMG 12228)
Pseudomonas aeruginosa (strain ATCC 15692 / PAO1 / 1C / PRS 101 / LMG 12228)
Pseudomonas sp. (strain WBC-3)
Pseudomonas sp. (strain WBC-3)
Streptococcus mutans serotype c (strain ATCC 700610 / UA159)
Streptococcus mutans serotype c (strain ATCC 700610 / UA159)
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
21000
P15559
SDS-PAGE
688795
32000
-
Western blot analysis
692928
36000
-
gel filtration
394369
47000 - 69000
-
gel filtration, SDS-PAGE
394370
50000
-
NAD(P)H:quinone acceptor oxidoreductase 2, gel filtration
394377
52000
-
sedimentation equilibrium, sedimentation velocity
394352
52000
-
hydrophilic and hydrophobic isoforms, gel filtration
394364
52000
P58795
gel filtration
674276
55000
-
gel filtration
394354
60000
-
gel filtration
394353
60000
-
-
694519
60260
-
enzyme DII, gel filtration, SDS-PAGE, amino acid analysis
394368
61000
-
cytosolic and microsomal enzyme, gel filtration
14080
61600
-
gel filtration
394373
66070
-
enzyme DI, gel filtration, SDS-PAGE, amino acid analysis
394368
79000
P0A8G6
dynamic light scattering
674276
83000
-
gel filtration
660087
86000
-
gel filtration
715428
89000
P58795
dynamic light scattering
674276
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
?
-
x * 60000, SDS-PAGE
?
-
x * 55000, SDS-PAGE
?
-
x * 25000, recombinant enzyme, SDS-PAGE
?
-
x * 21-22000, SDS-PAGE
?
Helicobacter hepaticus ATCC51449
-
x * 21-22000, SDS-PAGE
-
dimer
-
2 * 27000, SDS-PAGE
dimer
-
2 * 21000, SDS-PAGE
dimer
-
2 * 21900, SDS-PAGE
dimer
-
2 * 30835, electrospray mass spectrometry
dimer
-
2 * 26000, NAD(P)H:quinone acceptor oxidoreductase 2, SDS-PAGE
dimer
-
2 * 32000, cytosolic and microsomal enzyme, SDS-PAGE
dimer
-
2 * 30000, hydrophilic and hydrophobic isoform, SDS-PAGE
dimer
P58795
2 * 22100, SDS-PAGE
homodimer
-
-
homodimer
-
-
homodimer
-
2 * 43000, SDS-PAGE
monomer
-
1 * 60000, SDS-PAGE
oligomer
O29904
-
tetramer
-
-
tetramer
-
4 * 21000, SDS-PAGE
tetramer
-
2 * 18000 + 2 * 8000-9000, SDS-PAGE
tetramer
P0A8G6
4 * 21200, SDS-PAGE
tetramer
P58795
4 * 22100, SDS-PAGE
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
tetramer
Hevea brasiliensis Mull.-Arg.
-
4 * 21000, SDS-PAGE
-
monomer
-
1 * 67000, enzyme DI, SDS-PAGE, 1 * 63000, enzyme DII, SDS-PAGE
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
POSTTRANSLATIONAL MODIFICATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
no glycoprotein
-
very unstable posttranslational modification is suggested that is not detectable by mass spectrometry
glycoprotein
-
all 6 isoforms are glycoproteins
no glycoprotein
-
-
Crystallization/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
crystal structure of WrbA with oxidized FMN
-
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
P39315
with and without FMN using the sitting drop vapor-diffusion technique
P15559
1H69 crystal structure-based in silico model of NQO1 active site, NQO1 complex with bound FAD and indolequinone
P15559
apo QR1 and QR1 in complex with duroquinone, to 2.0 A resolution
-
crystal structure of enzyme complexed with 5-methoxy-1,2-dimethyl-3-[(4-nitrophenoxy)methyl]indole-4,7-dione, 1.8 A resolution
-
dicumarol, RH1, E09 or ARH019 co-crystallized with NQO1
-
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
-
in complex with anticancer prodrug CB1954
-
in complex with inhibitor dicoumarol
-
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
-
1.6 M ammonium sulfate, 150 mM imidazole, pH 7.0, small needles
-
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
-
QR1 in complex with NADP+ or QR1 in complex with duroquinone
-
TEMPERATURE STABILITY
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
0
-
some days
394350
20
-
several h
394350
57
-
5 min, 90% loss of activity
394350
80
-
10 h, more than 70% of the latex enzyme activity is retained
660087
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 3C
-
not stable to repeated freeze-thaw cycles
-
sucrose, 0.25 M, essential for stabilization during storage at -20C and purification
-
STORAGE STABILITY
ORGANISM
UNIPROT
LITERATURE
-20C, some weeks
-
-80C, stable for at least 6 months
-
-80C, KPi buffer, 10% glycerol, several months
-
-20C, 0.25 M sucrose, several months
-
5C, 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
-
Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
blue affinity column chromatography, Resource Q column chromatography, and Superdex 200 gel filtration
-
for crystallization
P15559
recombinant enzyme
-
Agarose cibacron blue, AH-Sepharose, CM-cellulose, Sephacryl S-200 HR
-
by affinity chromatography
-
by affinity chromatography; of the recombinant protein by cibacron blue affinity chromatography
-
recombinant enzyme
-
recombinant NAD(P)H:quinone acceptor oxidoreductase 2, affinity chromatography on Affi-gel blue
-
affinity chromatography on Cibacron blue-Agarose
-
recombinant enzyme
-
purified as a C-terminal His tag fusion by ultracentrifugation and gel filtration, to apparent homogeneity
-
affinity chromatography on Cibacron blue F3GA
-
affinity chromatography on dicoumarol-Sepharose 4B
-
by affinity chromatography
-
microsomal enzyme, partial
-
partial, isoforms
-
recombinant enzyme
-
2 isoenzymes: D-I, D-II
-
recombinant enzyme
-
Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
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
-
expression in Escherichia coli
P15559
expression in Escherichia coli
-
into pET21a, His-tagged version overexpressed in Escherichia coli BL21 Origami competent cells
-
expressed in Escherichia coli
-
expressed in Escherichia coli; expression in Escherichia coli
-
expression in Escherichia coli
-
NAD(P)H:quinone acceptor oxidoreductase 2
-
QR-ARE-luciferase reporter plasmid expressed in MCF-7 cells
-
expression in Escherichia coli
-
expressed in Escherichia coli NADH dehydrogenase knockout strain ANN0222; expression in Escherichia coli
-
gene chrR, quantitative expression analysis and profile
-
into the pET30-LIC vector, overexpressed in Escherichia coli BL21(DE3)
-
expression in Escherichia coli
-
heterologous expression in Pichia pastoris
-
expression in Escherichia coli
Q5EI63
EXPRESSION
ORGANISM
UNIPROT
LITERATURE
NQO1 is inducible
-
Sudan I induces NQO1 expression in rat liver, kidney, and lung, real-time polymerase chain reaction expression analysis
-
ENGINEERING
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
N143A
P39315
residue near NADPH-binding site. About 10% of wild-type activity
N143L
P39315
residue near NADPH-binding site. About 10% of wild-type activity
W139A
P39315
residue near NADPH-binding site. About 30% of wild-type activity
W139F
P39315
residue near NADPH-binding site. Activity comparable to wild-type
W139I
P39315
residue near NADPH-binding site. About 50% of wild-type activity
Y140A
P39315
residue near NADPH-binding site. Almost complete loss of activity
Y140F
P39315
residue near NADPH-binding site. Activity comparable to wild-type
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
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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
P0A8G6
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
Y140I
P39315
residue near NADPH-binding site. Almost complete loss of activity
additional information
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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
Helicobacter hepaticus ATCC51449
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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
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C609T
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no significant differences between distributions of NQO1 C609T genotypes in patients with prostate cancer and controls
additional information
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P187S protein undergoes rapid turnover via the ubiquitin proteasomal pathway, cells with the homozygous NQO1*2 genotype have no measurable NQO1 activity
additional information
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QR1-deficient individuals exposed to occupational benzene are at a substantially higher risk of contracting leukemia than normal individuals
additional information
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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
APPLICATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
analysis
O29904
the enzyme is a catalyst for 1,4-dihydronicotinamide adenine dinucleotide-dependent amperometric biosensors and biofuel cells. For NADH detection, a linear range between 0.005 mM and 1 mM, a limit of detection of 0.003 mM, and a high sensitivity can be reached
analysis
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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
drug development
P15559
design of novel lavendamycin analogues with enhanced, selective, and potent antitumor activity
drug development
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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
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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
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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
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the enzyme is a valuable target for activating stimuli-responsive drug delivery systems based on quinone derivatives, such as prodrugs and liposomes
medicine
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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
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enzyme is highly upregulated in active and chronic multiple sclerosis lesions, particularly in hypertrophic astrocytes and myelin-laden macrophages
medicine
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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
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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
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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
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statistically significant risk for colorectal cancer is associated with variant enzyme genotypes
medicine
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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
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NQO1 polymorphism analysis is performed to investigate the relationship between prostate cancer and NQO1 C609T polymorphism in a turkish population, no correlation is found
medicine
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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
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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
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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
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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
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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
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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
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genetic variation, especially the NQO1 609CT polymorphism, is a more important predictor of rectal NQO1 phenotype than fruit and vegetable consumption. White blood cell NQO1 activity is not a good surrogate for rectal activity
medicine
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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
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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
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no association between NQO1 polymorphism and the risk of anthracycline-related congestive heart failure among childhood cancer survivors
medicine
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NQO1 and SULT1A1 polymorphisms are associated with the risk of urothelial cancer, particularly among those who have ever smoked
medicine
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NQO1 gene polymorphism influences interleukin-6 levels and therefore attenuates the inflammatory response after cardiopulmonary bypass
medicine
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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
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synthesis of novel heterocyclic quinones (benzimidazole- and benzothiazole-quinones) as excellent substrates for recombinant human NQO1
medicine
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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
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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
pharmacology
P15559
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
medicine
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plays a protective role against the induction of renal tumors by diethylstilbestrol
drug development
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ability of ketoconazole and itraconazole to induce NQO1 gene expression at the transcriptional level through an aryl hydrocarbon receptor-dependent mechanism
drug development
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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
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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
-
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
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activation of antitumor prodrugs
medicine
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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
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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
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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
drug development
Mus musculus C3H
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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
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medicine
Mus musculus CD-1
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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
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degradation
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TcpB is acting as a quinone reductase for 6-chlorohydroxyquinone reduction during 2,4,6-trichlorophenol degradation, a toxic pollutant
drug development
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cytoprotective effect of bromocriptine involving PI3K- and Nrf2-mediated upregulation of the antioxidant enzyme NQO1, which may be a therapeutic strategy to protect cells from oxidative damage in Parkinsons disease
drug development
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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
medicine
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3-nitrobenzanthrone is capable to induce NQO1 and CYP1A1 in lungs and kidney of rats thereby enhancing its own genotoxic and carcinogenic potential
medicine
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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
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dependence of copper neurotoxicity on DT-diaphorase inhibition
medicine
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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
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neuroprotective role of DT-diaphorase against aminochrome neurotoxicity
medicine
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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
additional information
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PIFI is a novel component essential for NDH-mediated nonphotochemical reduction of the plastoquinone pool in chlororespiratory electron transport
biotechnology
P15559
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
additional information
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WrbA bridges flavodoxins and oxidoreductases. WrbA shows a close relationship to mammalian Nqo1
medicine
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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
additional information
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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
medicine
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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
additional information
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oxidative stress-type cytotoxicity of chromate in FLK cells may be partly attributed to its reduction by NQO1, but not by glutathione reductase