Information on EC 1.10.99.2 - ribosyldihydronicotinamide dehydrogenase (quinone)

Please wait a moment until all data is loaded. This message will disappear when all data is loaded.
Specify your search results
Mark a special word or phrase in this record:
Select one or more organisms in this record:
Show additional data
Do not include text mining results
Include (text mining) results (more...)
Include results (AMENDA + additional results, but less precise; more...)


The expected taxonomic range for this enzyme is: Eutheria

EC NUMBER
COMMENTARY
1.10.99.2
-
RECOMMENDED NAME
GeneOntology No.
ribosyldihydronicotinamide dehydrogenase (quinone)
REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT ACCESSION NO.
LITERATURE
1-(beta-D-ribofuranosyl)-1,4-dihydronicotinamide + a quinone = 1-(beta-D-ribofuranosyl)nicotinamide + a hydroquinone
show the reaction diagram
-
-
-
-
REACTION TYPE
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
oxidation
-
-
redox reaction
-
-
reduction
-
-
SYSTEMATIC NAME
IUBMB Comments
1-(beta-D-ribofuranosyl)-1,4-dihydronicotinamide:quinone oxidoreductase
A flavoprotein. Unlike EC 1.6.5.2, NAD(P)H dehydrogenase (quinone), this quinone reductase cannot use NADH or NADPH; instead it uses N-ribosyl- and N-alkyldihydronicotinamides. Polycyclic aromatic hydrocarbons, such as benz[a]anthracene, and the oestrogens 17beta-estradiol and diethylstilbestrol are potent inhibitors, but dicoumarol is only a very weak inhibitor [2]. This enzyme can catalyse both 2-electron and 4-electron reductions, but one-electron acceptors, such as potassium ferricyanide, cannot be reduced [3].
SYNONYMS
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
bQR2
-
-
dihydronicotinamide riboside:quinone oxidoreductase 2
-
-
dihydronicotinamide riboside:quinone reductase 2
-
-
melatonin-binding site MT3
-
-
MT3
P16083
-
MT3/NQO2
-
-
N-ribosyldihydronicotinamide dehydrogenase (quinone)
-
-
N-ribosyldihydronicotinamide:quinone oxidoreductase 2
-
-
NQO2
-
-
NQO2
Q9JI75
-
NRH-oxidizing enzyme
-
-
NRH:QR2
-
-
NRH:quinone oxidoreductase
-
-
NRH:quinone oxidoreductase
Q9JI75
-
NRH:quinone oxidoreductase 2
-
-
NRH:quinone oxidoreductase 2
P16083
-
NRH:quinone oxidoreductase 2
-
-
NRH:quinone oxidoreductase 2
-
-
NRH:quinone oxireductase 2
-
-
NRH:quinone reductase 2
P16083
-
NRH:quinone reductase 2
-
-
QR2
-
-
QR2
P16083
-
quinone oxidoreductase 2
-
-
quinone reductase 2
-
-
quinone reductase 2
P16083
-
quinone reductase 2
-
-
quinone reductase 2
-
-
quinone reductase 2
-
-
quinone reductase type 2
-
-
CAS REGISTRY NUMBER
COMMENTARY
667919-86-0
-
ORGANISM
COMMENTARY
LITERATURE
SEQUENCE CODE
SEQUENCE DB
SOURCE
comparison with quinone reductase 1
SwissProt
Manually annotated by BRENDA team
expressed in CHO cells
-
-
Manually annotated by BRENDA team
recombinant
SwissProt
Manually annotated by BRENDA team
recombinant
-
-
Manually annotated by BRENDA team
stably expressed in CHO cells
-
-
Manually annotated by BRENDA team
GENERAL INFORMATION
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
malfunction
-
adult QR2 knock-out mice demonstrate enhanced learning abilities in various tasks, including Morris water maze, object recognition, and rotarod performance test, while other behaviors related to anxiety (elevated plus maze), depression (forced swim), and schizophrenia (prepulse inhibition) are not affected in QR2-deficient mice. QR2 inhibition protects hippocampal cells against menadione-induced toxicity and serum deprivation and can reverse cognitive deficits
physiological function
-
QR2 plays a role in cognitive behaviors
physiological function
-
the enzyme functions in metabolic reduction and detoxification processes. Evidence exists linking QR2 to the metabolic activation of quinones, which can lead to cell toxicity. Inhibition of the enzymme by resveratrol may protect cells against reactive intermediates and eventually cancer
physiological function
-
quinone reductase 2 is an FAD-linked enzyme and the only known human target of two antimalarial drugs, primaquine and chloroquine, a functional role for NQO2 as a flavin redox switch
physiological function
-
ribosyldihydronicotinamide dehydrogenase is a detoxification oxidoreductase, it is a flavoprotein that catalyzes the 2-electron reduction of various quinones, redox dyes, and the vitamin K menadione. NQO2 predominantly uses dihydronicotinamide riboside as the electron donor
malfunction
-
specific inhibitors of QR2, tested in vivo, show outstanding properties impairing memory loss
additional information
-
comparison of isoenzymes Qr1 and QR2, overview
additional information
-
QR2 does not share many features with QR1. Particularly, it does not seem to have a similar detoxifying function in cells. QR2 is overexpressed in neurodegenerative diseases
SUBSTRATE
PRODUCT                      
REACTION DIAGRAM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
(Substrate)
LITERATURE
(Substrate)
COMMENTARY
(Product)
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
1-(beta-D-ribofuranosyl)-1,4-dihydronicotinamide + a quinone
1-(beta-D-ribofuranosyl)nicotinamide + a hydroquinone
show the reaction diagram
-
-
-
-
?
1-(beta-D-ribofuranosyl)-1,4-dihydronicotinamide + co-enzyme Q
1-(beta-D-ribofuranosyl)nicotinamide + reduced co-enzyme Q
show the reaction diagram
-
natural substrate nicotinamide riboside, NRH
-
-
?
1-(beta-D-ribofuranosyl)-1,4-dihydronicotinamide + menadione
1-(beta-D-ribofuranosyl)nicotinamide + menadiol
show the reaction diagram
-
-
-
-
?
1-(beta-D-ribofuranosyl)-1,4-dihydronicotinamide + menadione
1-(beta-D-ribofuranosyl)nicotinamide + menadiol
show the reaction diagram
-
natural substrate nicotinamide riboside, NRH
-
-
?
1-(carbamoylmethyl)dihydronicotinamide + 3-hydroxy-1-methylindoline-5,6-dione
1-(carbamoylmethyl)nicotinamide + 3-hydroxy-1-methylindoline-5,6-diol
show the reaction diagram
-
3-hydroxy-1-methylindoline-5,6-dione i.e. adrenochrome
-
-
?
1-carbamoylmethyl-3-carbamoyl-1,4-dihydropyrimidine + menadione
1-carbamoylmethyl-3-carbamoylpyrimidine + menadiol
show the reaction diagram
-
-
-
-
?
17beta-17-hydroxyestr-1(10)-ene-3,4-dione + benzyldihydronicotinamide riboside
17beta-estra-1(10),2,4-triene-3,4,17-triol + benzylnicotinamide riboside
show the reaction diagram
-
ping-pong mechanism, NQO2 is faster in reducing estrogen quinones than its homologue NQO1
-
-
?
2,6-dichloroindophenol + dihydronicotinamide riboside
? + nicotinamide riboside
show the reaction diagram
-
-
-
-
?
5-(aziridin-1-yl)-2,4-dinitrobenzamide + dihydronicotinamide riboside
? + nicotinamide riboside
show the reaction diagram
-
-
-
-
?
5-(aziridin-1-yl)-2,4-dinitrobenzamide + menadiol
? + reduced menadiol
show the reaction diagram
-
-
-
-
?
benzo(a)pyrene-3,6-quinone + dihydronicotinamide riboside
? + nicotinamide riboside
show the reaction diagram
-
-
-
-
?
dihydrobenzylnicotinamide + menadione
?
show the reaction diagram
-
-
-
-
?
dihydronicotinamide riboside + 2,6-dichlorophenolindophenol
nicotinamide riboside + reduced 2,6-dichlorophenolindophenol
show the reaction diagram
-
-
-
-
?
dihydronicotinamide riboside + 3-(4,5-dimethylthiazaol-2-yl)-2,5-diphenyltetrazolium
nicotinamide riboside + ?
show the reaction diagram
-
-
-
-
?
dihydronicotinamide riboside + CB 1954
nicotinamide riboside + ?
show the reaction diagram
-
-
-
-
?
dihydronicotinamide riboside + menadione
ribosyl nicotinamide + menadiol
show the reaction diagram
-
-
-
-
?
dihydronicotinamide riboside + menadione/3-(4,5-dimethylthiazaol-2-yl)-2,5-diphenyltetrazolium
nicotinamide riboside + ?
show the reaction diagram
-
-
-
-
?
dihydronicotinamide riboside + methyl red
nicotinamide riboside + ?
show the reaction diagram
-
-
-
-
?
estrone-3,4-quinone + N-benzyldihydronicotinamide
estrone-3,4-quinol + N-benzylnicotinamide
show the reaction diagram
-
ping-pong mechanism, NQO2 is faster in reducing estrogen quinones than its homologue NQO1
-
-
?
menadione + 1-(2-hydroxyethyl)dihydronicotinamide
?
show the reaction diagram
P16083
-
-
-
?
menadione + dihydrobenzylnicotinamide
?
show the reaction diagram
-
-
-
-
?
menadione + dihydronicotinamide riboside
menadiol + nicotinamide riboside
show the reaction diagram
-
-
-
-
?
N -benzyldihydronicotinamide + a quinone
N-benzylnicotinamide + a hydroquinone
show the reaction diagram
-
synthetic substrate
-
-
?
N-benzyldihydronicotinamide + 2,6-dichlorophenolindophenol
N-benzylnicotinamide + reduced 2,6-dichlorophenolindophenol
show the reaction diagram
-
-
-
-
?
N-benzyldihydronicotinamide + 2,6-dichlorophenolindophenol
N-benzylnicotamide + reduced 2,6-dichlorophenolindophenol
show the reaction diagram
-
-
-
-
?
N-benzyldihydronicotinamide + coenzyme Q0
?
show the reaction diagram
-
-
-
-
?
N-benzyldihydronicotinamide + coenzyme Q0
N-benzylnicotinamide + ?
show the reaction diagram
-
-
-
-
?
N-benzyldihydronicotinamide + coenzyme Q1
N-benzylnicotinamide + ?
show the reaction diagram
-
-
-
-
?
N-benzyldihydronicotinamide + menadione
?
show the reaction diagram
-
-
-
-
?
N-benzyldihydronicotinamide + menadione
?
show the reaction diagram
-
-
-
-
?
N-benzyldihydronicotinamide + menadione
N-benzylnicotinamide + menadiol
show the reaction diagram
-
-
-
-
?
N-benzyldihydronicotinamide + menadione
N-benzylnicotamide + menadiol
show the reaction diagram
-
-
-
-
?
N-benzyldihydronicotinamide + oxidized coenzyme Q0
N-benzylnicotinamide + reduced coenzyme Q20
show the reaction diagram
-
-
-
-
?
N-benzyldihydronicotinamide + oxidized coenzyme Q1
N-benzylnicointamide + reduced coenzyme Q1
show the reaction diagram
-
-
-
-
?
N-benzyldihydronicotinamide + oxidized coenzyme Q2
N-benzylnicotinamide + reduced coenzyme Q2
show the reaction diagram
-
-
-
-
?
N-benzylnicotinamide + menadiol
?
show the reaction diagram
-
-
-
-
?
N-methyldihydronicotinamide + 3-(4,5-dimethylthiazol-2-yl)-2,5-dipenyltetrazolium bromide
N-methylnicotinamide + ?
show the reaction diagram
-
-
-
-
?
N-methyldihydronicotinamide + 3-hydroxy-1-methylindoline-5,6-dione
N-methylnicotinamide + 3-hydroxy-1-methylindoline-5,6-diol
show the reaction diagram
-
3-hydroxy-1-methylindoline-5,6-dione i.e. adrenochrome. When NADH is used as the electron donor, quinone reductase 2 possesses no activity for the reduction of adrenochrome
-
-
?
N-methyldihydronicotinamide + menadione
?
show the reaction diagram
-
-
-
-
?
N-methyldihydronicotinamide + menadione
?
show the reaction diagram
P16083
-
-
-
?
N-methyldihydronicotinamide + menadione
N-methylnicotinamide + menadiol
show the reaction diagram
-
-
-
-
?
N-ribosylnicotinamide + menadiol
?
show the reaction diagram
-
N-ribosylnicotinamide is a poor substrate
-
-
?
nicotinamide riboside + menadiol
dihydronicotinamide riboside + menadione
show the reaction diagram
-
-
-
-
?
nicotinamide riboside + reduced 2,6-dichlorophenolindophenol
dihydronicotinamide riboside + 2,6-dichlorophenolindophenol
show the reaction diagram
-
-
-
-
?
nicotinamide riboside + reduced coenzyme Q0
dihydronicotinamide riboside + coenzyme Q0
show the reaction diagram
-
-
-
-
?
nicotinamide riboside + reduced coenzyme Q1
dihydronicotinamide riboside + coenzyme Q1
show the reaction diagram
-
-
-
-
?
nicotinamide riboside + reduced coenzyme Q2
dihydronicotinamide riboside + coenzyme Q2
show the reaction diagram
-
-
-
-
?
reduced N-methyldihydronicotinamide + menadione
? + menadiol
show the reaction diagram
-
-
-
-
?
reduced N1-(benzyl)-nicotinamide + menadione
N1-(benzyl)-nicotinamide + menadiol
show the reaction diagram
-
-
-
-
?
reduced N1-(methyl)-nicotinamide + menadione
N1-(methyl)-nicotinamide + reduced menadiol
show the reaction diagram
-
-
-
-
?
reduced N1-(n-propyl)-nicotinamide + menadione
N1-(n-propyl)-nicotinamide + menadiol
show the reaction diagram
-
-
-
-
?
tetrahydrofolate + menadiol
?
show the reaction diagram
-
-
-
-
?
mitomycin C + dihydronicotinamide riboside
? + nicotinamide riboside
show the reaction diagram
-
-
-
-
?
additional information
?
-
-
by deleting QR2 it seems that mice become increasingly susceptible to polycyclic aromatic hydrocarbon-induced skin carcinogenesis
-
-
-
additional information
?
-
-
enzyme exhibits melatonin-binding activity
-
-
-
additional information
?
-
P16083
high QR2 activity might make individuals more susceptible to Parkinsons disease. By inhibiting QR2, it seems that anti-malarial compounds such as quinacrine favour the red blood cell oxidative stress leading to the death of the parasite
-
-
-
additional information
?
-
P16083
knockdown K562 cells exhibit increased antioxidant and detoxification enzyme expression and reduced proliferation rates
-
-
-
additional information
?
-
-
organs of mice deleted for NQO2 are depleted of MT3 binding sites. NQO2 is part of the melatonin receptor MT3 binding sites
-
-
-
additional information
?
-
-
the expression of the NQO2 gene is induced in response to 2,3,7,8-tetrachlorodibenzo-p-dioxin
-
-
-
additional information
?
-
P16083
enzyme cannot use NADH or NADPH as reducing agent
-
-
-
additional information
?
-
-
no activity with NADH, NADPH, NMNH, reduced 3-acetylpyridine adenine dinucleotide, xanthine or hypoxanthine. No activity with 1,4-benzoquinone and potassium ferricyanide
-
-
-
additional information
?
-
-
no activity with one-electron acceptors such as potassium ferricyanide
-
-
-
additional information
?
-
-
the D allele in the promoter is associated with higher NQO2 activity and increases levels of ROS in the presence of dopamine, which would then increase susceptibility to Parkinson's disease
-
-
-
additional information
?
-
-
NQO2 catalyzes the reduction of electrophilic estrogen quinones and thereby may act as a detoxification enzyme
-
-
-
additional information
?
-
-
quinone reductase 2 is a target of resveratrol in vascular smooth muscle cells. Resveratrol reduces quinone reductase protein levels and suppresses quinone reductase 2 mRNA expression in cultured vascular smooth muscle cell. The inhibition of vascular smooth muscle cell proliferation by resveratrol is effected via the negative regulation of quinone reductase 2. Quinone reductase 2 may be the main target for resveratrol and may be used to mediate the potential therapeutic role of resveratrol in atherosclerosis and restenosis after injury
-
-
-
additional information
?
-
-
the enzyme does not accept conventional phosphorylated nicotinamides as hydride donors
-
-
-
additional information
?
-
-
NQO2 can function as a nitroreductase in activating the antitumor drug 5-aziridinyl-2,4-dinitrobenzamide
-
-
-
additional information
?
-
-
the enzyme catalyzes the reduction of quinones, such as menadione and co-enzyme Q, QR2 produces free radicals with pro-drug CB1954, i.e. 5-(aziridin-1-yl)-2,4-dinitrobenzamide. The anti-cancer pro-drug CB1954 (5-(aziridin-1-yl)-2,4-dinitrobenzamide) is transformed into a potent cytotoxic drug upon reduction of its 4-nitro group to a 4-hydroxylamine by quinone reductases or nitroreductase
-
-
-
additional information
?
-
-
quinone reductase 2 (QR2) is implicated in the reduction of quinone in the presence of natural derivatives of NADH such as N-ribosyldihydronicotinamide. QR2 does not recognize NADH or NADPH as co-substrates, unlike quinone reductase 1 (QR1)
-
-
-
NATURAL SUBSTRATES
NATURAL PRODUCTS
REACTION DIAGRAM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
(Substrate)
LITERATURE
(Substrate)
COMMENTARY
(Product)
LITERATURE
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
1-(beta-D-ribofuranosyl)-1,4-dihydronicotinamide + a quinone
1-(beta-D-ribofuranosyl)nicotinamide + a hydroquinone
show the reaction diagram
-
-
-
-
?
1-(beta-D-ribofuranosyl)-1,4-dihydronicotinamide + co-enzyme Q
1-(beta-D-ribofuranosyl)nicotinamide + reduced co-enzyme Q
show the reaction diagram
-
natural substrate nicotinamide riboside, NRH
-
-
?
1-(beta-D-ribofuranosyl)-1,4-dihydronicotinamide + menadione
1-(beta-D-ribofuranosyl)nicotinamide + menadiol
show the reaction diagram
-
-
-
-
?
1-(beta-D-ribofuranosyl)-1,4-dihydronicotinamide + menadione
1-(beta-D-ribofuranosyl)nicotinamide + menadiol
show the reaction diagram
-
natural substrate nicotinamide riboside, NRH
-
-
?
additional information
?
-
-
by deleting QR2 it seems that mice become increasingly susceptible to polycyclic aromatic hydrocarbon-induced skin carcinogenesis
-
-
-
additional information
?
-
-
enzyme exhibits melatonin-binding activity
-
-
-
additional information
?
-
P16083
high QR2 activity might make individuals more susceptible to Parkinsons disease. By inhibiting QR2, it seems that anti-malarial compounds such as quinacrine favour the red blood cell oxidative stress leading to the death of the parasite
-
-
-
additional information
?
-
P16083
knockdown K562 cells exhibit increased antioxidant and detoxification enzyme expression and reduced proliferation rates
-
-
-
additional information
?
-
-
organs of mice deleted for NQO2 are depleted of MT3 binding sites. NQO2 is part of the melatonin receptor MT3 binding sites
-
-
-
additional information
?
-
-
the expression of the NQO2 gene is induced in response to 2,3,7,8-tetrachlorodibenzo-p-dioxin
-
-
-
additional information
?
-
-
the D allele in the promoter is associated with higher NQO2 activity and increases levels of ROS in the presence of dopamine, which would then increase susceptibility to Parkinson's disease
-
-
-
additional information
?
-
-
NQO2 catalyzes the reduction of electrophilic estrogen quinones and thereby may act as a detoxification enzyme
-
-
-
additional information
?
-
-
quinone reductase 2 is a target of resveratrol in vascular smooth muscle cells. Resveratrol reduces quinone reductase protein levels and suppresses quinone reductase 2 mRNA expression in cultured vascular smooth muscle cell. The inhibition of vascular smooth muscle cell proliferation by resveratrol is effected via the negative regulation of quinone reductase 2. Quinone reductase 2 may be the main target for resveratrol and may be used to mediate the potential therapeutic role of resveratrol in atherosclerosis and restenosis after injury
-
-
-
additional information
?
-
-
NQO2 can function as a nitroreductase in activating the antitumor drug 5-aziridinyl-2,4-dinitrobenzamide
-
-
-
additional information
?
-
-
the enzyme catalyzes the reduction of quinones, such as menadione and co-enzyme Q
-
-
-
COFACTOR
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
IMAGE
FAD
-
one prosthetic group per subunit
FAD
P16083
contains 1 FAD per monomer firmly bound to the enzyme through multiple interactions
FAD
-
the enzyme contains FAD as the sole bound flavin. The prosthetic group can be removed by treatment with acid in ammonium sulfate, and the resolved enzyme may be reactivated by FAD or by higher concentrations FMN
FAD
-
very tightly bound to the enzyme. Activity of the purified enzyme is not further increased by added FAD
FAD
-
mediates hydride transfer, very tightly bound to the enzyme. Activity of the purified enzyme is not further increased by added FAD
FAD
-
dstabilisation of the cofactor FAD by mutation N18E shows that 2-[125I]-iodo-5-methoxycarbonylamino-N-acetyltryptamine binding is closely linked to the conformational integrity of quinone oxidoreductase 2
FAD
-
dependent on
FAD
-
1 molecule per subunit, binds to the active site of each subunit
FAD
-
flavoenzyme, binding structure, overview. 2 molecules per enzyme dimer, quantification, overview
FAD
-
flavin redox switch, structural changes, overview
NADH
-
very poor electron donor
Nicotinamide riboside
-
reduced nicotinamide riboside
Nicotinamide riboside
-
-
Nicotinamide riboside
-
-
FMN
-
the enzyme contains FAD as the sole bound flavin. The prosthetic group can be removed by treatment with acid in ammonium sulfate, and the resolved enzyme may be reactivated by FAD or by higher concentrations FMN
additional information
P16083
enzyme cannot use NADH or NADPH as reducing agent
-
additional information
-
completely inert to NADPH, NADH and NMNH
-
METALS and IONS
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
Zn2+
-
-
INHIBITORS
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
IMAGE
(E)-3-(3,5-dihydroxyphenyl)-2-(4-hydroxyphenyl)acrylaldehyde
-
-
(E)-3-(3,5-dimethoxyphenyl)-2-(4-methoxyphenyl)prop-2-en-1-ol
-
-
(Z)-3-(3,5-dihydroxyphenyl)-2-(4-hydroxyphenyl)-acrylamide
-
-
(Z)-3-(3,5-dihydroxyphenyl)-2-(4-hydroxyphenyl)acrylonitrile
-
-
(Z)-3-(3,5-dimethoxyphenyl)-2-(4-methoxyphenyl)acrylaldehyde
-
-
(Z)-3-(3,5-dimethoxyphenyl)-2-(4-methoxyphenyl)acrylonitrile
-
-
(Z)-5-(3-hydroxy-2-(4-hydroxyphenyl)prop-1-en-1-yl)benzene-1,3-diol
-
-
1,1'-(1E)-but-1-ene-1,2-diylbis(3,5-dimethoxybenzene)
-
-
1,2-dimethoxy-4-[(1E)-2-(4-methoxyphenyl)prop-1-en-1-yl]benzene
-
-
1,2-dimethoxy-4-[(E)-2-(3-methoxyphenyl)ethenyl]benzene
-
-
1,2-dimethoxy-4-{(1Z)-3,3,3-trifluoro-2-[3-(trifluoromethyl)phenyl]prop-1-en-1-yl}benzene
-
-
1,3-dimethoxy-5-[(1E)-2-(4-methoxyphenyl)prop-1-en-1-yl]benzene
-
-
1,3-dimethoxy-5-[(1Z)-3,3,3-trifluoro-1-(4-methoxyphenyl)prop-1-en-2-yl]benzene
-
-
1,3-dimethoxy-5-[(E)-2-(4-methoxyphenyl)ethenyl]benzene
-
-
1,4-dimethylphenanthrene
-
0.00001 mM, 15% inhibition of the reaction with N1-(n-propyl)-nicotinamide
1,4-dimethylquinolin-2(1H)-one
-
-
1-[(E)-2-(4-fluorophenyl)ethenyl]-3,5-dimethoxybenzene
-
-
12-methylbenz[a]anthracene
-
0.00001 mM, 51% inhibition of the reaction with N1-(n-propyl)-nicotinamide
2-(2-methoxy-6H-pyrido[2',3':4,5]pyrrolo[2,1-a]isoindol-11-yl)ethylamine
-
IC50: 0.00087 mM
2-hydroxyestradiol
-
0.01 mM, 17% inhibition
2-iodo-5-methoxycarbonylamino-N-acetyltryptamine
-
-
2-iodo-melatonin
-
IC50: 0.016 mM
2-iodomelatonin
-
-
2-iodomelatonin
-
-
2-[(E)-2-(3,4-dimethoxyphenyl)ethenyl]naphthalene
-
-
2-[(E)-2-(3,5-dimethoxyphenyl)ethenyl]naphthalene
-
-
3-{[4-(dihydroxyamino)phenoxy]methyl}-5-methoxy-1,2-dimethyl-1H-indole-4,7-dione
-
-
4',5,7-trihydroxyflavone
-
0.01 mM, 61% inhibition
4-hydroxyestradiol
-
0.01 mM, 18% inhibition
4-hydroxyestrone
-
0.01 mM, 22% inhibition
4-[(1E)-1-(3,5-dimethoxyphenyl)prop-1-en-2-yl]-1,2-dimethoxybenzene
-
-
4-[(E)-2-(3,4-dimethoxyphenyl)ethenyl]-N,N-dimethylaniline
-
-
4-[(E)-2-(3,5-dimethoxyphenyl)ethenyl]-1,2-dimethoxybenzene
-
-
4-[(E)-2-(3,5-dimethoxyphenyl)ethenyl]phenol
-
-
4-[(E)-2-(3-fluorophenyl)ethenyl]benzene-1,2-diol
-
-
4-[(E)-2-(4-hydroxyphenyl)ethenyl]benzene-1,2-diol
-
-
4-[(E)-2-(4-methoxyphenyl)ethenyl]benzene-1,2-diol
-
-
4-{(1E)-1-[4-(trifluoromethyl)phenyl]prop-1-en-2-yl}phenol
-
-
4-{(E)-2-[3-(trifluoromethyl)phenyl]ethenyl}benzene-1,2-diol
-
-
5,6,8-trimethoxy-1,4-dimethylquinolin-2(1H)-one
-
-
5,6,8-trimethoxy-4-methylquinolin-2(1H)-one
-
-
5,8-dimethoxy-1,4-dimethylquinolin-2(1H)-one
-
-
5,8-dimethoxy-4-methylquinolin-2(1H)-one
-
-
5-(2-(dimethylamino)ethylamino)-6H-[1,2,3]triazolo[4,5,1-de]acridin-6-one
-
-
-
5-(2-(dimethylamino)ethylamino)-6H-[1,2,3]triazolo[4,5,1-de]acridin-6-one N-oxide
-
-
-
5-(2-(dimethylamino)ethylamino)-8-bromo-6H-[1,2,3]triazolo[4,5,1-de]acridin-6-one
-
-
-
5-(2-(dimethylamino)ethylamino)-8-bromo-6H-[1,2,3]triazolo[4,5,1-de]acridin-6-one N-oxide
-
-
-
5-(2-(dimethylamino)ethylamino)-8-fluoro-6H-[1,2,3]triazolo[4,5,1-de]acridin-6-one
-
-
-
5-(2-(dimethylamino)ethylamino)-8-methoxy-6H-[1,2,3]triazolo[4,5,1-de]acridin-6-one
-
-
-
5-(2-(dimethylamino)ethylamino)-8-methoxy-6H-[1,2,3]triazolo[4,5,1-de]acridin-6-one N-oxide
-
-
-
5-(3-dydroxypropylamino)-6H-[1,2,3]triazolo[4,5,1-de]acridin-6-one
-
-
-
5-(3-hydroxypropylamino)-8-bromo-6H-[1,2,3]triazolo[4,5,1-de]acridin-6-one
-
-
-
5-(3-hydroxypropylamino)-8-methoxy-6H-[1,2,3]triazolo[4,5,1-de]acridin-6-one
-
-
-
5-(4-methoxyphenylamino)-6H-[1,2,3]triazolo[4,5,1-de]acridin-6-one
-
-
-
5-(isopentylamino)-6H-[1,2,3]triazolo[4,5,1-de]acridin-6-one
-
-
-
5-(phenethylamino)-6H-[1,2,3]triazolo[4,5,1-de]acridin-6-one
-
-
-
5-amino-1,2-dimethyl-3-[(2,4,6-trifluorophenoxy)methyl]-1H-indole-4,7-dione
-
-
5-hydroxyflavone
-
IC50: 340 nM
5-hydroxytryptamine
-
-
5-methoxy-carbonylamino-N-acetyltryptamine
-
IC50: 0.295 mM
5-methoxycarbonylamino-N-acetyltryptamine
-
-
5-[(1E)-1-(4-hydroxyphenyl)prop-1-en-2-yl]benzene-1,3-diol
-
-
5-[(1E)-2-(3,4-dimethoxyphenyl)prop-1-en-1-yl]benzene-1,3-diol
-
-
5-[(1E)-2-(4-hydroxyphenyl)prop-1-en-1-yl]benzene-1,3-diol
-
-
5-[(1E)-2-(4-methoxyphenyl)prop-1-en-1-yl]benzene-1,3-diol
-
-
5-[(4-aminobutyl)amino]-1,2-dimethyl-3-[(2,4,6-trifluorophenoxy)methyl]-1H-indole-4,7-dione
-
-
5-[(4-aminobutyl)amino]-1,2-dimethyl-3-[(4-nitrophenoxy)methyl]-1H-indole-4,7-dione
-
-
5-[(8-aminooctyl)amino]-1,2-dimethyl-3-[(2,4,6-trifluorophenoxy)methyl]-1H-indole-4,7-dione
-
-
5-[butyl(methyl)amino]-1,2-dimethyl-3-[(2,4,6-trifluorophenoxy)methyl]-1H-indole-4,7-dione
-
-
5-[[4-(diethylamino)butyl]amino]-10-methoxy-6H-imidazo[4,5,1-de]acridin-6-one
-
-
5-[[4-(diethylamino)butyl]amino]-6H-imidazo[4,5,1-de]acridin-6-one
-
-
5-[[4-(diethylamino)butyl]amino]-7,10-dimethoxy-6H-imidazo[4,5,1-de]acridin-6-one
-
-
5-[[4-(diethylamino)butyl]amino]-7-hydroxy-10-methoxy-6H-imidazo[4,5,1-de]acridin-6-one
-
-
5-[[4-(diethylamino)butyl]amino]-7-hydroxy-8,9-dimethoxy-6H-imidazo[4,5,1-de]acridin-6-one
-
most potent inhibitor of NQO2
5-[[4-(diethylamino)butyl]amino]-8-hydroxy-1-methyl-6H-imidazo[4,5,1-de]acridin-6-one
-
-
5-[[4-(diethylamino)butyl]amino]-8-hydroxy-6H-imidazo[4,5,1-de]acridin-6-one
-
-
5-[[4-(diethylamino)butyl]amino]-8-methoxy-1-methyl-6H-imidazo[4,5,1-de]acridin-6-one
-
-
5-[[4-(diethylamino)butyl]amino]-8-methoxy-6H-imidazo[4,5,1-de]acridin-6-one
-
-
5-[[4-(diethylamino)butyl]amino]-9-hydroxy-6H-imidazo[4,5,1-de]acridin-6-one
-
-
5-[[4-(dimethylamino)butyl]amino]-1-ethyl-6H-imidazo[4,5,1-de]acridin-6-one
-
-
5-[[4-(dimethylamino)butyl]amino]-1-methyl-6H-imidazo[4,5,1-de]acridin-6-one
-
-
5-[[4-(dimethylamino)butyl]amino]-6H-imidazo[4,5,1-de]acridin-6-one
-
-
5-[[4-(dimethylamino)butyl]amino]-8-hydroxy-1-methyl-6H-imidazo[4,5,1-de]acridin-6-one
-
-
5-[[4-(dimethylamino)butyl]amino]-8-hydroxy-6H-imidazo[4,5,1-de]acridin-6-one
-
-
5-[[6-(diethylamino)hexyl]amino]-8-hydroxy-6H-imidazo[4,5,1-de]acridin-6-one
-
-
5-[[6-(dimethylamino)hexyl]amino]-6H-imidazo[4,5,1-de]acridin-6-one
-
-
5-{(1E)-1-[4-(dimethylamino)phenyl]but-1-en-2-yl}benzene-1,3-diol
-
-
5-{[2-(dimethylamino)ethyl]amino}-1,2-dimethyl-3-(phenoxymethyl)-1H-indole-4,7-dione
-
-
5-{[2-(dimethylamino)ethyl]amino}-1,2-dimethyl-3-[(2,4,6-trifluorophenoxy)methyl]-1H-indole-4,7-dione
-
-
5-{[2-(dimethylamino)ethyl]amino}-1-methyl-2-phenyl-3-[(2,4,6-trifluorophenoxy)methyl]-1H-indole-4,7-dione
-
-
5-{[2-(dimethylamino)ethyl]amino}-1-methyl-3-[(2,4,6-trifluorophenoxy)methyl]-1H-indole-4,7-dione
-
-
5-{[3-(dimethylamino)propyl]amino}-1,2-dimethyl-3-[(2,4,6-trifluorophenoxy)methyl]-1H-indole-4,7-dione
-
-
6,7,8-trimethoxy-1,4-dimethylquinolin-2(1H)-one
-
-
6,7,8-trimethoxy-4-methylquinolin-2(1H)-one
-
-
6,8-dimethoxy-1,4-dimethylquinolin-2(1H)-one
-
-
6,8-dimethoxy-4-methylquinolin-2(1H)-one
-
-
6,9-dimethyl-[1,3]dioxolo[4,5-h]quinolin-8(9H)-one
-
-
6-methoxy-9-methyl-[1,3]dioxolo[4,5-h]quinolin-8(9H)-one
-
-
6-methyl-[1,3]dioxolo[4,5-h]quinolin-8(9H)-one
-
-
7,12-dimethylbenz[a]anthracene
-
0.00001 mM, 51% inhibition of the reaction with N1-(n-propyl)-nicotinamide
7,8-dihydroxyflavone
-
0.01 mM, 7% inhibition
7,8-dimethoxy-1,4-dimethylquinolin-2(1H)-one
-
-
7,8-dimethoxy-4-methylquinolin-2(1H)-one
-
-
7-methylbenz[a]anthracene
-
0.00001 mM, 66% inhibition of the reaction with N1-(n-propyl)-nicotinamide
8-bromo-5-[(3-methylbutyl)amino]-6H-[1,2,3]triazolo[4,5,1-de]acridin-6-one
-
-
8-methoxy-1,4-dimethylquinolin-2(1H)-one
-
-
8-methoxy-4-methylquinolin-2(1H)-one
-
-
8-methoxy-5-(phenethylamino)-6H-[1,2,3]triazolo[4,5,1-de]acridin-6-one
-
-
-
9,10-dimethylanthracene
-
0.00001 mM, 25% inhibition of the reaction with N1-(n-propyl)-nicotinamide
9-methylanthracene
-
0.00001 mM, 26% inhibition of the reaction with N1-(n-propyl)-nicotinamide
alpha-Naphthoflavone
-
0.01 mM, 75% inhibition
apigenin
-
IC50: 430 nM
benzo(a)pyrene
-
20 mM, 90% inhibition
benzo(a)pyrene
-
-
benzo[a]pyrene
-
0.0001 mM, 75% inhibition
benz[a]anthracene
-
0.00001 mM, 40% inhibition of the reaction with N1-(n-propyl)-nicotinamide
beta-Naphthoflavone
-
0.01 mM, 76% inhibition
Chloroquine
-
-
Chloroquine
-
binds preferentially to reduced NQO2, binding mode, closure of a flexible loop (Phe126-Leu136) over the active site, overview
chrysin
-
0.01 mM, complete inhibition
chrysin-dimethylether
-
IC50: 0.0013 mM
chrysoeriol
-
IC50: 300 nM
chrysoeriol
-
-
dabigatran
-
; specific binding to the enzyme, protein interaction analysis, overview
dabigatran ethyl ester
-
-
-
dicoumarol
-
0.01 mM, 25% inhibition
dicoumarol
-
IC50: 0.59 mM
dicoumarol
-
0.01 mM, marginal inhibition
estradiol
-
0.01 mM, 13% inhibition
ethyl 3-(2-((4-(N-(4-(tert-butoxycarbonylamino)butyl)-carbamimidoyl)phenylamino)methyl)-1-methyl-N-(pyridin-2-yl)-1H-benzo[d]imidazole-5-carboxamido)propanoate
-
-
ethyl N-[(2-{[(4-carbamimidoylphenyl)amino]methyl}-1H-benzimidazol-5-yl)carbonyl]-N-pyridin-2-yl-b-alaninate
-
-
flavone
-
0.01 mM, 14% inhibition
galangin
-
0.01 mM, complete inhibition
genistein
-
-
imatinib
-
the structure of the imatinib-NQO2 complex demonstrates that imatinib inhibits NQO2 activity by competing with substrate for the active site
isorhamnetin
-
IC50: 860 nM
kaempferol
-
IC50: 380 nM
luteolin
-
IC50: 780 nM
mefloquine
-
-
melagatran
-
-
Melatonin
-
IC50: 0.13 mM
Melatonin
-
competitive inhibitor against N-methyldihydronicotinamide, uncompetitive against menadione. Melatonin and its analogues bind to and inhibit QR2 within the active site and not at an allosteric site
Melatonin
-
QR2 is inhibited in the micromolar range by melatonin, but not when using N-benzyl dihydronicotinamide and coenzyme Q2 are used as substrates
methyl 2-((S)-1-cyclohexyl-2-((R)-2-(4-(4-(4-nitrophenylsulfonamido)butylcarbamoyl)benzylcarbamoyl)-azetidin-1-yl)-2-oxoethylamino)acetate
-
-
methyl N-{(1R)-1-cyclohexyl-2-oxo-2-[(2S)-2-{[4-({4-[(N-{17-oxo-21-[(3aS,4S,6aR)-2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl]-4,8,12-trioxa-16-azahenicos-1-yl}-N2-{4-[3-(trifluoromethyl)-3H-diaziren-3-yl]benzoyl}-L-alpha-asparaginyl)amino]butyl}carbamoyl)benzyl]carbamoyl}azetidin-1-yl]ethyl}glycinate
-
-
morin
-
0.01 mM, 95% inhibition
N-(3,5-dihydroxyphenyl)-4-hydroxybenzamide
-
-
N-acetyl-5-hydroxytryptamine
-
-
N-acetylserotonin
-
IC50: 0.099 mM
N-[2-(2-iodo-5-methoxy-1-methyl-4-nitroindol-3-yl)ethyl]acetamide
-
inhibits enzymatic mechanism of the enzyme through the MT3 binding site, IC50: 0.0003 mM
N-[2-(2-methoxy-6H-dipyrido[2,3-a:3,2-e]pyrrolizin-11-yl)ethyl]-2-furamide
-
IC50: 14 nM
N-[2-(2-methoxy-6H-pyrido[2',3':4,5]pyrrolo[2,1-a]isoindol-11-yl)ethyl]2-furamide
-
IC50: 0.0002 mM
N-[2-(5-methoxy-4-nitro-1H-indol-3-yl)ethyl]acetamide
-
IC50: 0.0015 mM
N-[2-(5-methoxy-7-nitro-1H-indol-3-yl)ethyl]acetamide
-
IC50: 0.044 mM
N-[2-(7-methylaminosulfonyl-1-naphthyl)ethyl]acetamide
-
IC50: 0.038 mM
N-[2-(8-methoxy-3,4-dihydro-2H-pyrido[2',3':4,5]pyrrolo[2,1-b][1,3]oxazin-10-yl)ethyl]-2-furamide
-
IC50: 0.005 mM
N-{(1R)-1-cyclohexyl-2-oxo-2-[(2S)-2-{[4-({4-[(N-{17-oxo-21-[(3aS,4S,6aR)-2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl]-4,8,12-trioxa-16-azahenicos-1-yl}-N2-{4-[3-(trifluoromethyl)-3H-diaziren-3-yl]benzoyl}-L-alpha-asparaginyl)amino]butyl}carbamoyl)benzyl]carbamoyl}azetidin-1-yl]ethyl}glycine
-
-
N-{[1-methyl-2-({[4-(N-{3-[(N-{17-oxo-21-[(3aS,4S,6aR)-2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl]-4,8,12-trioxa-16-azahenicos-1-yl}-N2-{4-[3-(trifluoromethyl)-3H-diaziren-3-yl]benzoyl}-L-alpha-asparaginyl)amino]propyl}carbamimidoyl)phenyl]amino}methyl)-1H-benzimidazol-5-yl]carbonyl}-N-pyridin-2-yl-beta-alanine
-
-
N1-[2-(2-methoxy-6H-pyrido[2',3':4,5]pyrrolo[2,1-a]isoindol-11-yl)ethyl]-acetamide
-
IC50: 0.0019 mM
N4-[2-(4-{4-[(4-methyl-3-{[4-(pyridin-3-yl)pyrimidin-2-yl]amino}phenyl)carbamoyl]benzyl}piperazin-1-yl)ethyl]-N1-{17-oxo-21-[(3aS,4S,6aR)-2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl]-4,8,12-trioxa-16-azahenicos-1-yl}-N2-{4-[3-(trifluoromethyl)-3H-diaziren-3-yl]benzoyl}-L-aspartamide
-
-
N4-[3-({N-[(2-{[(4-carbamimidoylphenyl)amino]methyl}-1-methyl-1H-benzimidazol-5-yl)carbonyl]-N-phenyl-b-alanyl}amino)propyl]-N1-{17-oxo-21-[(3aS,4S,6aR)-2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl]-4,8,12-trioxa-16-azahenicos-1-yl}-N2-{4-[3-(trifluoromethyl)-3H-diaziren-3-yl]benzoyl}-L-aspartamide
-
-
N4-[4-({N-[(1R)-2-{(2R)-2-[(4-carbamimidoylbenzyl)carbamoyl]cyclobutyl}-1-cyclohexylprop-2-en-1-yl]glycyl}amino)butyl]-N1-{17-oxo-21-[(3aS,4S,6aR)-2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl]-4,8,12-trioxa-16-azahenicos-1-yl}-N2-{4-[3-(trifluoromethyl)-3H-diaziren-3-yl]benzoyl}-L-aspartamide
-
-
NSC106080
-
i.e. bis(2-hydroxyphenyl)methanone phenylhydrazone
-
NSC115890
-
i.e. 1,3-naphthalenediol
-
NSC180969
-
i.e. 7,8-dimethoxy-4-(3,4,5-trimethoxyphenyl)-1,2-dihydro-3H-benzo[e]isoindol-3-one
-
NSC187208
-
i.e. N4-(7-chloro-4-quinolinyl)-N1,N1-diethyl-1,4-pentanediamine, chloroquine
-
NSC204996
-
i.e. 7,8-dimethoxy-4-(3,4,5-trimethoxyphenyl)-2,3-dihydro-1H-benzo[e]isoindole
-
NSC238146
-
i.e. N4-(6-((6-amino-2-methyl-4-quinolinyl)amino)hexyl)-2-methyl-4,6-quinolinediamine acetate
-
NSC27296
-
i.e. N4-(6-methoxy-8-quinolinyl)-1,4-pentanediamine, primaquine
-
NSC300853
-
i.e. 3-amino-9-ethyl-2-((4-(hydroxy(oxido)amino)phenyl)diazenyl)-9H-carbazole
-
NSC306843
-
i.e. 1-methyl-4(1H)-quinolinone (1-methyl-4(1H)-quinolinylidene)hydrazone
-
NSC332172
-
i.e. 2-(4-methoxyphenyl)-3-(3,4,5-trimethoxyphenyl)acrylonitrile
-
NSC356819
-
i.e. 4-((2-hydroxy-5-(phenyldiazenyl)phenyl)diazenyl)benzenecarboximidamide
-
NSC356820
-
i.e. 4-((2-hydroxy-5-(2-phenylvinyl)phenyl)diazenyl)benzenecarboximidamide
-
NSC359466
-
i.e. 4-((4-(amino(imino)methyl)phenyl)diazenyl)-3-hydroxy-N-phenyl-2-naphthamide
-
NSC381864
-
i.e. 5-(2-(3,5-dimethoxyphenyl)vinyl)-2-methoxyphenol
-
NSC621351
-
i.e. 2-(2-fluorophenyl)-4-(2-naphthyl)-2,3-dihydro-1,5-benzothiazepine
-
NSC623234
-
i.e. 3-chloro-3-(3,4-dimethoxyphenyl)-2-(3,4,5-trimethoxyphenyl)acrylaldehyde
-
NSC637991
-
-
NSC637992
-
-
NSC637993
-
-
NSC637994
-
-
NSC640353
-
i.e. 1-(2-(3,5-diphenyl-1H-pyrazol-1-yl)-4-methyl-1,3-thiazol-5-yl)-4-methyl-5-phenyl-2,4-pentadien-1-one
-
NSC640556
-
i.e. 1-(2-(3,5-diphenyl-1H-pyrazol-1-yl)-4-methyl-1,3-thiazol-5-yl)-3-(4-(hydroxy(oxido)amino)phenyl)-2-propen-1-one
-
NSC640558
-
i.e 1-(2-(3,5-diphenyl-1H-pyrazol-1-yl)-4-methyl-1,3-thiazol-5-yl)-3-phenyl-2-propen-1-one
-
NSC640559
-
i.e. 1-(2-(3,5-diphenyl-1H-pyrazol-1-yl)-4-methyl-1,3-thiazol-5-yl)-3-(3-(hydroxy(oxido)amino)phenyl)-2-propen-1-one
-
NSC640566
-
i.e. 3-(4-chlorophenyl)-1-(2-(3,5-diphenyl-1H-pyrazol-1-yl)-4-methyl-1,3-thiazol-5-yl)-2-propen-1-one
-
NSC640583
-
i.e. 1-(2-(3,5-diphenyl-1H-pyrazol-1-yl)-4-methyl-1,3-thiazol-5-yl)-3-(4-methylphenyl)-2-propen-1-one
-
NSC640584
-
i.e. 3-(3,4-dichlorophenyl)-1-(2-(3,5-diphenyl-1H-pyrazol-1-yl)-4-methyl-1,3-thiazol-5-yl)-2-propen-1-one
-
NSC645808
-
-
NSC645809
-
-
NSC645811
-
-
NSC645812
-
-
NSC645831
-
-
NSC645833
-
-
NSC645834
-
-
NSC645835
-
-
NSC645836
-
-
NSC648420
-
i.e. 1,2,3-trimethoxyphenanthro[2,3-d][1,3]dioxol-6-yl acetate
-
NSC648422
-
i.e. 5-(1-methyl-2-(3,4,5-trimethoxyphenyl)vinyl)-1,3-benzodioxole
-
NSC649091
-
i.e. 2-((diethylamino)methyl)-4-((10-methyl-10H-indolo[3,2-b]quinolin-11-yl)amino)phenol hydrochloride
-
NSC65069
-
i.e. [1,1'-biphenyl]-2,3',4,5',6-pentol
-
NSC660838
-
-
-
NSC660839
-
-
NSC660840
-
-
NSC660841
-
most potent inhibitor of NQO2
NSC660841
-
one of the most potent inhibitors of NQO2
NSC66167
-
i.e. [1,1'-biphenyl]-2,2',4,4'-tetrol
-
NSC665126
-
i.e. 1-(2-(4-(hydroxy(oxido)amino)phenyl)vinyl)-3-phenylbenzo[f]quinoline
-
NSC669977
-
i.e. 6-imino-1-methyl-3-phenyl-2,6-dihydro-5(1H)-quinolinone hydrazone
-
NSC676468
-
i.e. N-(3-([1,10-biphenyl]-4-ylimino)-1-propenyl)[1,10-biphenyl]-4-amine
-
NSC677939
-
i.e. 14H-diindolo[2,3-a:3,2-h]quinolizine
-
NSC693571
-
i.e. trifluoromethanesulfonic acid compound with N,N-dimethyl-4-((1-methyl-2-phenyl-4H-1lambda5-pyrazolo[1,5-a]indol-4-ylidene)methyl)aniline
-
NSC720622
-
i.e. trifluoromethanesulfonic acid compound with N,N-dimethyl-4-((1-methyl-6-nitro-2-phenylpyrazolo[1,5-a]indol-1-ium-4-ylidene)methyl)aniline
-
NSC77833
-
i.e. 1-(2-(1H-indol-3-yl)vinyl)isoquinoline
-
NSC78017
-
i.e. 2,6-dimethyl-3H-pyrrolo[3,2-f]quinoline
-
NSC78021
-
i.e. 4,7-dimethyl-7H-pyrido[2,3-c]carbazole
-
NSC86715
-
i.e. 5-methyl-1-phenyl-6H-pyrido[4,3-b]carbazole
-
NSC97374
-
i.e. 1-ethyl-2-((1-ethyl-2(1H)-quinolinylidene)methyl)-1lambda5-quinoline
-
NSC99495
-
i.e. 3-benzo[a]anthracen-12-ylthiophene
-
NSC99528
-
i.e. 2-benzo[a]anthracen-12-yl-1-benzothiophene
-
primaquine
-
-
primaquine
-
binding mode, overview
quercetin
-
0.01 mM, complete inhibition
quercetin
-
IC50: 0.0014 mM
quercetin
-
-
quercetin-3-O-beta-glucopyranosyl
-
IC50: 0.0015 mM
Quinacrine
-
-
resveratrol
-
the chemopreventive and cardioprotective properties of resveratrol are possibly the results of QR2 activity inhibition, which in turn, up-regulates the expression of cellular antioxidant enzymes and cellular resistance to oxidative stress. All three resveratrol hydroxyl groups form hydrogen bonds with amino acids from QR2, anchoring a flat resveratrol molecule in parallel with the isoalloxazine ring of FAD
resveratrol
-
i.e. 3,5,4'-trihydroxylstilbene, resveratrol binds tightly to the oxidized, FAD-form of the enzyme, and it acts as a competitive inhibitor against N-methyldihydronicotinamide. The amount of resveratrol consumed from dietary sources may be sufficient for effective inhibition of QR2
S26553
-
i.e. N-methyl-[1-[2-(acetylamino)ethyl]napthalen-7-yl]-carbamate
S26695
-
i.e. N-[2-(7-methylaminosulfonyl-1-naphthyl)ethyl]acetamide
-
S26695
-
selective inhibitor of QR2
-
S26695
-
-
-
S28128
-
IC50: 0.00091 mM
S29434
-
i.e. N-[2-(2-methoxy-6H-dipyrido[2,3-a:3,2-e]pyrrolizin-11-yl)ethyl]-2-furamide, inhibits QR2 activity with an IC50 in the low nanomolar range from 0.7 to 80 nM, depending on the substrates and co-substrates used
-
S29434
-
selective inhibitor of QR2
-
S29434
-
synthetic compound, complete inhibition
-
serotonin
-
-
tert-butyl 4-(4-(4-nitrophenylsulfonamido)butylcarbamoyl)-benzylcarbamate
-
-
tert-butyl(S)-1-cyclohexyl -2-((R)-2-(4-(4-(4-nitrophenylsulfonamido)butylcarbamoyl)benzylcarbamoyl)-azetidin-1-yl)-2-oxoethylcarbamate
-
-
-
methyl-1-(2-acetamidoethyl)-7-naphthylcarbamate
-
IC50: 0.015 mM
additional information
-
not inhibited by dicoumarol, Cibacron blue, phenindone
-
additional information
-
melatonin has no effect
-
additional information
-
no inhibition by 4-methylquinolin-2(1H)-one. 6-Methoxy-9-methyl-[1,3]dioxolo[4,5-h]quinolin-8(9H)-one and its analogues merit further investigation as potential chemopreventive or chemotherapeutic agents
-
additional information
-
dicoumarol is inactive up to 0.1 mM
-
additional information
-
enzyme inhibitor design, synthesiis, and evaluation, inhibitory potencies of resveratrol analogues, overview. Inhibitor binding structure, modelling, overview
-
additional information
-
development of potent and selective mechanism-based inhibitors centered on the indolequinone pharmacophore. The compounds show remarkable selectivity for NQO2 over the closely related flavoprotein NQO1, with small structural changes defining selectivity, detailed overview. The inhibitor's mode of action involving alkylation of the flavin cofactor, provides significant advantages over existing competitive inhibitors in terms of potency and irreversibility
-
additional information
-
inhibitor binding structures, overview
-
additional information
-
molecular dockings predicts and biological experiments confirm that dabigatran ethyl ester inhibits NQO2 even more effectively than the parent compound itself, usage of capture compounds, overview
-
KM VALUE [mM]
KM VALUE [mM] Maximum
SUBSTRATE
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
IMAGE
0.00075
-
17beta-17-hydroxyestr-1(10)-ene-3,4-dione
-
-
0.007
-
2,6-dichlorophenolindophenol
-
-
0.0102
-
2,6-dichlorophenolindophenol
-
using N-benzyl dihydronicotinamide as cosubstrate, at 25C, in 50 mM Tris-HCl, pH 8.5
0.019
-
2,6-dichlorophenolindophenol
-
chimeric enzyme of the human NQO2 with 43 amino acids from the carboxyl terminus of human DT-diaphorase
0.012
-
3-(4,5-dimethylthiazaol-2-yl)-2,5-diphenyltetrazolium
-
-
0.061
-
5-(aziridin-1-yl)-2,4-dinitrobenzamide
-
at 25C in pH 8.5 buffer (50 mM Tris, 140 mM NaCl, and 0.1% Tween 20) with 0.1 mM menadione as co-substrate
0.26
-
CB 1954
-
-
0.0137
-
coenzyme Q0
-
using N-benzyl dihydronicotinamide as cosubstrate, at 25C, in 50 mM Tris-HCl, pH 8.5
0.0517
-
coenzyme Q1
-
using N-benzyl dihydronicotinamide as cosubstrate, at 25C, in 50 mM Tris-HCl, pH 8.5
0.0387
-
Coenzyme Q2
-
using N-benzyl dihydronicotinamide as cosubstrate, at 25C, in 50 mM Tris-HCl, pH 8.5
0.02
-
dihydrobenzylnicotinamide
-
pH 8.5, 25C, fluorescence assay
0.04
-
dihydrobenzylnicotinamide
-
pH 8.5, HPLC approach
0.0576
-
dihydrobenzylnicotinamide
-
pH 7.5
0.0608
-
dihydrobenzylnicotinamide
-
pH 7.5
0.028
-
dihydronicotinamide riboside
-
-
3.3e-05
-
estradiol-3,4-quinone
-
-
0.0016
-
menadione
-
pH 7.6, with reduced N1-(n-propyl)-nicotinamide as acceptor
0.0067
-
menadione
-
pH 8.5, 25C, fluorescence assay
0.0067
-
menadione
-
-
0.0089
-
menadione
-
pH 7.5
0.0111
-
menadione
-
using N-benzyl dihydronicotinamide as cosubstrate, at 25C, in 50 mM Tris-HCl, pH 8.5
0.017
-
menadione
-
pH 8.5, HPLC approach
0.0252
-
menadione
-
pH 7.5
0.0023
-
menadione/3-(4,5-dimethylthiazaol-2-yl)-2,5-diphenyltetrazolium
-
-
0.0113
-
N-benzyl dihydronicotinamide
-
using menadione as cosubstrate, at 25C, in 50 mM Tris-HCl, pH 8.5
0.0361
-
N-benzyl dihydronicotinamide
-
using coenzyme Q0 as cosubstrate, at 25C, in 50 mM Tris-HCl, pH 8.5
0.0404
-
N-benzyl dihydronicotinamide
-
using 2,6-dichlorophenolindophenol as cosubstrate, at 25C, in 50 mM Tris-HCl, pH 8.5
0.0451
-
N-benzyl dihydronicotinamide
-
using coenzyme Q1 as cosubstrate, at 25C, in 50 mM Tris-HCl, pH 8.5
0.0602
-
N-benzyl dihydronicotinamide
-
using coenzyme Q2 as cosubstrate, at 25C, in 50 mM Tris-HCl, pH 8.5
0.02
-
N-benzyldihydronicotinamide
-
-
0.252
-
NADH
-
-
0.023
-
reduced N1-(n-propyl)-nicotinamide
-
pH 7.6
2
-
tetrahydrofolate
-
-
0.0047
-
Methyl red
-
-
additional information
-
additional information
-
steady-state kinetic, overview
-
TURNOVER NUMBER [1/s]
TURNOVER NUMBER MAXIMUM[1/s]
SUBSTRATE
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
IMAGE
46.67
-
2,6-dichlorophenolindophenol
-
-
91.8
-
2,6-dichlorophenolindophenol
-
chimeric enzyme of the human NQO2 with 43 amino acids from the carboxyl terminus of human DT-diaphorase
11
-
3-(4,5-dimethylthiazaol-2-yl)-2,5-diphenyltetrazolium
-
-
6
-
5-(aziridin-1-yl)-2,4-dinitrobenzamide
-
at 25C in pH 8.5 buffer (50 mM Tris, 140 mM NaCl, and 0.1% Tween 20) with 0.1 mM menadione as co-substrate
6
-
CB 1954
-
-
43.33
-
dihydronicotinamide riboside
-
-
38.33
-
menadione/3-(4,5-dimethylthiazaol-2-yl)-2,5-diphenyltetrazolium
-
-
3.83
-
Methyl red
-
-
2.6
-
NADH
-
-
Ki VALUE [mM]
Ki VALUE [mM] Maximum
INHIBITOR
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
IMAGE
0.012
-
2-iodo-5-methoxycarbonylamino-N-acetyltryptamine
-
oxidized form hQR2-FAD
0.033
-
2-iodo-5-methoxycarbonylamino-N-acetyltryptamine
-
reduced form hQR2-FADH2
0.004
-
2-iodo-melatonin
-
reduced form hQR2-FADH2
0.05
-
2-iodo-melatonin
-
oxidized form hQR2-FAD
0.0012
-
2-iodomelatonin
-
pH 7.5
0.029
-
2-iodomelatonin
-
pH 7.5
0.0435
-
5-methoxycarbonylamino-N-acetyltryptamine
-
pH 7.5
0.376
-
5-methoxycarbonylamino-N-acetyltryptamine
-
pH 7.5
0.00061
-
Chloroquine
-
-
0.07
-
dabigatran
-
pH and temperature not specified in the publication
0.0009
-
dabigatran ethyl ester
-
pH and temperature not specified in the publication
-
0.566
-
dicoumarol
-
pH 7.5
0.62
-
dicoumarol
-
pH 7.5
0.017
-
mefloquine
-
-
0.0072
-
Melatonin
-
pH 8, 25C, competitive inhibitor against N-methyldihydronicotinamide
0.043
-
Melatonin
-
pH 7.5
0.092
-
Melatonin
-
pH 8, 25C, uncompetitive against menadione
0.15
-
Melatonin
-
reduced form hQR2-FADH2
0.092
-
N-acetylserotonin
-
pH 7.5
0.204
-
N-acetylserotonin
-
pH 7.5
8e-05
-
N-[2-(2-iodo-5-methoxy-1-methyl-4-nitroindol-3-yl)ethyl]acetamide
-
oxidized form hQR2-FAD
0.00031
-
N-[2-(2-iodo-5-methoxy-1-methyl-4-nitroindol-3-yl)ethyl]acetamide
-
reduced form hQR2-FADH2
3e-05
-
N-[2-(2-methoxy-6H-dipyrido[2,3-a:3,2-e]pyrrolizin-11-yl)ethyl]-2-furamide
-
reduced form hQR2-FADH2
4e-05
-
N-[2-(2-methoxy-6H-dipyrido[2,3-a:3,2-e]pyrrolizin-11-yl)ethyl]-2-furamide
-
oxidized form hQR2-FAD
0.00104
-
primaquine
-
-
2.1e-05
-
quercetin
-
-
0.00051
-
Quinacrine
-
-
0.252
-
Quinine
-
-
5e-05
-
resveratrol
-
-
8.8e-05
-
resveratrol
-
versus N-methyldihydronicotinamide, pH and temperature not specified in the publication
0.0028
-
S26553
-
pH 7.5
0.0414
-
S26553
-
pH 7.5
0.00018
-
S28128
-
oxidized form hQR2-FAD
0.0009
-
S28128
-
reduced form hQR2-FADH2
2.933
-
serotonin
-
-
0.246
-
Melatonin
-
pH 7.5
additional information
-
additional information
-
Michaelis-Menten inhibition kinetics
-
IC50 VALUE [mM]
IC50 VALUE [mM] Maximum
INHIBITOR
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
IMAGE
0.0182
-
1,4-dimethylquinolin-2(1H)-one
-
23C
0.00087
-
2-(2-methoxy-6H-pyrido[2',3':4,5]pyrrolo[2,1-a]isoindol-11-yl)ethylamine
-
IC50: 0.00087 mM
0.016
-
2-iodo-melatonin
-
IC50: 0.016 mM
0.0011
-
2-iodomelatonin
-
pH 8, 25C
0.0108
-
5,6,8-trimethoxy-1,4-dimethylquinolin-2(1H)-one
-
23C
0.006
-
5,6,8-trimethoxy-4-methylquinolin-2(1H)-one
-
23C
0.0041
-
5,8-dimethoxy-1,4-dimethylquinolin-2(1H)-one
-
23C
0.0108
-
5,8-dimethoxy-4-methylquinolin-2(1H)-one
-
23C
0.001833
-
5-(2-(dimethylamino)ethylamino)-6H-[1,2,3]triazolo[4,5,1-de]acridin-6-one
-
in 50 mM phosphate buffer at pH 7.4, at 37C
-
0.000167
-
5-(2-(dimethylamino)ethylamino)-6H-[1,2,3]triazolo[4,5,1-de]acridin-6-one N-oxide
-
in 50 mM phosphate buffer at pH 7.4, at 37C
-
0.001483
-
5-(2-(dimethylamino)ethylamino)-8-bromo-6H-[1,2,3]triazolo[4,5,1-de]acridin-6-one
-
in 50 mM phosphate buffer at pH 7.4, at 37C
-
0.000117
-
5-(2-(dimethylamino)ethylamino)-8-bromo-6H-[1,2,3]triazolo[4,5,1-de]acridin-6-one N-oxide
-
in 50 mM phosphate buffer at pH 7.4, at 37C
-
0.000783
-
5-(2-(dimethylamino)ethylamino)-8-fluoro-6H-[1,2,3]triazolo[4,5,1-de]acridin-6-one
-
in 50 mM phosphate buffer at pH 7.4, at 37C
-
0.001333
-
5-(2-(dimethylamino)ethylamino)-8-methoxy-6H-[1,2,3]triazolo[4,5,1-de]acridin-6-one
-
in 50 mM phosphate buffer at pH 7.4, at 37C
-
9.8e-05
-
5-(2-(dimethylamino)ethylamino)-8-methoxy-6H-[1,2,3]triazolo[4,5,1-de]acridin-6-one N-oxide
-
in 50 mM phosphate buffer at pH 7.4, at 37C
-
0.000483
-
5-(3-dydroxypropylamino)-6H-[1,2,3]triazolo[4,5,1-de]acridin-6-one
-
in 50 mM phosphate buffer at pH 7.4, at 37C
-
0.000987
-
5-(3-hydroxypropylamino)-8-bromo-6H-[1,2,3]triazolo[4,5,1-de]acridin-6-one
-
in 50 mM phosphate buffer at pH 7.4, at 37C
-
0.000517
-
5-(3-hydroxypropylamino)-8-methoxy-6H-[1,2,3]triazolo[4,5,1-de]acridin-6-one
-
in 50 mM phosphate buffer at pH 7.4, at 37C
-
9.8e-05
-
5-(4-methoxyphenylamino)-6H-[1,2,3]triazolo[4,5,1-de]acridin-6-one
-
in 50 mM phosphate buffer at pH 7.4, at 37C
-
0.000427
-
5-(isopentylamino)-6H-[1,2,3]triazolo[4,5,1-de]acridin-6-one
-
in 50 mM phosphate buffer at pH 7.4, at 37C
-
0.000567
-
5-(phenethylamino)-6H-[1,2,3]triazolo[4,5,1-de]acridin-6-one
-
in 50 mM phosphate buffer at pH 7.4, at 37C
-
0.00034
-
5-hydroxyflavone
-
IC50: 340 nM
0.0539
-
5-hydroxytryptamine
-
pH 8, 25C
0.295
-
5-methoxy-carbonylamino-N-acetyltryptamine
-
IC50: 0.295 mM
9.9e-05
-
5-[[4-(diethylamino)butyl]amino]-10-methoxy-6H-imidazo[4,5,1-de]acridin-6-one
-
pH and temperature not specified in the publication
0.000427
-
5-[[4-(diethylamino)butyl]amino]-6H-imidazo[4,5,1-de]acridin-6-one
-
pH and temperature not specified in the publication
1.7e-05
-
5-[[4-(diethylamino)butyl]amino]-7,10-dimethoxy-6H-imidazo[4,5,1-de]acridin-6-one
-
pH and temperature not specified in the publication
3.1e-05
-
5-[[4-(diethylamino)butyl]amino]-7-hydroxy-10-methoxy-6H-imidazo[4,5,1-de]acridin-6-one
-
pH and temperature not specified in the publication
6e-06
-
5-[[4-(diethylamino)butyl]amino]-7-hydroxy-8,9-dimethoxy-6H-imidazo[4,5,1-de]acridin-6-one
-
pH and temperature not specified in the publication
1.6e-05
-
5-[[4-(diethylamino)butyl]amino]-8-hydroxy-1-methyl-6H-imidazo[4,5,1-de]acridin-6-one
-
pH and temperature not specified in the publication
0.000148
-
5-[[4-(diethylamino)butyl]amino]-8-hydroxy-6H-imidazo[4,5,1-de]acridin-6-one
-
pH and temperature not specified in the publication
9e-06
-
5-[[4-(diethylamino)butyl]amino]-8-methoxy-1-methyl-6H-imidazo[4,5,1-de]acridin-6-one
-
pH and temperature not specified in the publication
0.001
-
5-[[4-(diethylamino)butyl]amino]-8-methoxy-6H-imidazo[4,5,1-de]acridin-6-one
-
pH and temperature not specified in the publication
0.000953
-
5-[[4-(diethylamino)butyl]amino]-9-hydroxy-6H-imidazo[4,5,1-de]acridin-6-one
-
pH and temperature not specified in the publication
0.000693
-
5-[[4-(dimethylamino)butyl]amino]-1-ethyl-6H-imidazo[4,5,1-de]acridin-6-one
-
pH and temperature not specified in the publication
0.000323
-
5-[[4-(dimethylamino)butyl]amino]-1-methyl-6H-imidazo[4,5,1-de]acridin-6-one
-
pH and temperature not specified in the publication
0.00083
-
5-[[4-(dimethylamino)butyl]amino]-6H-imidazo[4,5,1-de]acridin-6-one
-
pH and temperature not specified in the publication
5e-05
-
5-[[4-(dimethylamino)butyl]amino]-8-hydroxy-1-methyl-6H-imidazo[4,5,1-de]acridin-6-one
-
pH and temperature not specified in the publication
0.000296
-
5-[[4-(dimethylamino)butyl]amino]-8-hydroxy-6H-imidazo[4,5,1-de]acridin-6-one
-
pH and temperature not specified in the publication
0.000597
-
5-[[6-(diethylamino)hexyl]amino]-8-hydroxy-6H-imidazo[4,5,1-de]acridin-6-one
-
pH and temperature not specified in the publication
0.000172
-
5-[[6-(dimethylamino)hexyl]amino]-6H-imidazo[4,5,1-de]acridin-6-one
-
pH and temperature not specified in the publication
0.007
-
6,7,8-trimethoxy-1,4-dimethylquinolin-2(1H)-one
-
23C
0.01
-
6,7,8-trimethoxy-4-methylquinolin-2(1H)-one
-
23C
0.0019
-
6,8-dimethoxy-1,4-dimethylquinolin-2(1H)-one
-
23C
0.0088
-
6,8-dimethoxy-4-methylquinolin-2(1H)-one
-
23C
0.0062
-
6,9-dimethyl-[1,3]dioxolo[4,5-h]quinolin-8(9H)-one
-
23C
0.0541
-
6-methoxy-9-methyl-[1,3]dioxolo[4,5-h]quinolin-8(9H)-one
-
23C
0.0108
-
6-methyl-[1,3]dioxolo[4,5-h]quinolin-8(9H)-one
-
23C
0.0093
-
7,8-dimethoxy-1,4-dimethylquinolin-2(1H)-one
-
23C
0.0293
-
7,8-dimethoxy-4-methylquinolin-2(1H)-one
-
23C
0.000767
-
8-bromo-5-[(3-methylbutyl)amino]-6H-[1,2,3]triazolo[4,5,1-de]acridin-6-one
-
in 50 mM phosphate buffer at pH 7.4, at 37C
0.0058
-
8-methoxy-1,4-dimethylquinolin-2(1H)-one
-
23C
0.0241
-
8-methoxy-4-methylquinolin-2(1H)-one
-
23C
0.00035
-
8-methoxy-5-(phenethylamino)-6H-[1,2,3]triazolo[4,5,1-de]acridin-6-one
-
in 50 mM phosphate buffer at pH 7.4, at 37C
-
0.00043
-
apigenin
-
IC50: 430 nM
0.0013
-
chrysin-dimethylether
-
IC50: 0.0013 mM
1.6e-05
-
chrysoeriol
-
using nicotinamide riboside and menadione as substrates, at 25C, in 50 mM Tris-HCl, pH 8.5
7.6e-05
-
chrysoeriol
-
using nicotinamide riboside and coenzyme Q2 as substrates, at 25C, in 50 mM Tris-HCl, pH 8.5
0.00016
-
chrysoeriol
-
using N-benzyl dihydronicotinamide and menadione as substrates, at 25C, in 50 mM Tris-HCl, pH 8.5
0.0003
-
chrysoeriol
-
IC50: 300 nM
0.00082
-
chrysoeriol
-
using N-benzyl dihydronicotinamide and coenzyme Q2 as substrates, at 25C, in 50 mM Tris-HCl, pH 8.5
0.06
-
dabigatran
-
pH and temperature not specified in the publication
0.0008
-
dabigatran ethyl ester
-
pH and temperature not specified in the publication
-
0.59
-
dicoumarol
-
IC50: 0.59 mM
0.00086
-
isorhamnetin
-
IC50: 860 nM
0.00038
-
kaempferol
-
IC50: 380 nM
0.00078
-
luteolin
-
IC50: 780 nM
0.0028
-
Melatonin
-
using nicotinamide riboside and menadione as substrates, at 25C, in 50 mM Tris-HCl, pH 8.5
0.0113
-
Melatonin
-
pH 8, 25C
0.0113
-
Melatonin
-
23C
0.0397
-
Melatonin
-
using nicotinamide riboside and coenzyme Q2 as substrates, at 25C, in 50 mM Tris-HCl, pH 8.5
0.0415
-
Melatonin
-
using N-benzyl dihydronicotinamide and menadione as substrates, at 25C, in 50 mM Tris-HCl, pH 8.5
0.13
-
Melatonin
-
IC50: 0.13 mM
0.015
-
methyl-1-(2-acetamidoethyl)-7-naphthylcarbamate
-
IC50: 0.015 mM
0.0099
-
N-acetyl-5-hydroxytryptamine
-
pH 8, 25C
0.099
-
N-acetylserotonin
-
IC50: 0.099 mM
0.0003
-
N-[2-(2-iodo-5-methoxy-1-methyl-4-nitroindol-3-yl)ethyl]acetamide
-
inhibits enzymatic mechanism of the enzyme through the MT3 binding site, IC50: 0.0003 mM
1.4e-05
-
N-[2-(2-methoxy-6H-dipyrido[2,3-a:3,2-e]pyrrolizin-11-yl)ethyl]-2-furamide
-
IC50: 14 nM
0.0002
-
N-[2-(2-methoxy-6H-pyrido[2',3':4,5]pyrrolo[2,1-a]isoindol-11-yl)ethyl]2-furamide
-
IC50: 0.0002 mM
0.0015
-
N-[2-(5-methoxy-4-nitro-1H-indol-3-yl)ethyl]acetamide
-
IC50: 0.0015 mM
0.044
-
N-[2-(5-methoxy-7-nitro-1H-indol-3-yl)ethyl]acetamide
-
IC50: 0.044 mM
0.038
-
N-[2-(7-methylaminosulfonyl-1-naphthyl)ethyl]acetamide
-
IC50: 0.038 mM
0.005
-
N-[2-(8-methoxy-3,4-dihydro-2H-pyrido[2',3':4,5]pyrrolo[2,1-b][1,3]oxazin-10-yl)ethyl]-2-furamide
-
IC50: 0.005 mM
0.0019
-
N1-[2-(2-methoxy-6H-pyrido[2',3':4,5]pyrrolo[2,1-a]isoindol-11-yl)ethyl]-acetamide
-
IC50: 0.0019 mM
0.0039
-
NSC106080
-
in 50 mM phosphate buffer at pH 7.4, at 37C
-
0.0033
-
NSC115890
-
in 50 mM phosphate buffer at pH 7.4, at 37C
-
0.002
-
NSC180969
-
in 50 mM phosphate buffer at pH 7.4, at 37C
-
0.0015
-
NSC187208
-
in 50 mM phosphate buffer at pH 7.4, at 37C
-
0.0027
-
NSC204996
-
in 50 mM phosphate buffer at pH 7.4, at 37C
-
0.0019
-
NSC238146
-
in 50 mM phosphate buffer at pH 7.4, at 37C
-
0.0075
-
NSC27296
-
in 50 mM phosphate buffer at pH 7.4, at 37C
-
0.005
-
NSC300853
-
in 50 mM phosphate buffer at pH 7.4, at 37C
-
0.0062
-
NSC306843
-
in 50 mM phosphate buffer at pH 7.4, at 37C
-
0.02
-
NSC332172
-
in 50 mM phosphate buffer at pH 7.4, at 37C
-
0.0018
-
NSC356819
-
in 50 mM phosphate buffer at pH 7.4, at 37C
-
0.0014
-
NSC356820
-
in 50 mM phosphate buffer at pH 7.4, at 37C
-
0.006
-
NSC359466
-
in 50 mM phosphate buffer at pH 7.4, at 37C
-
0.015
-
NSC381864
-
in 50 mM phosphate buffer at pH 7.4, at 37C
-
0.022
-
NSC623234
-
in 50 mM phosphate buffer at pH 7.4, at 37C
-
5e-05
-
NSC637991
-
pH and temperature not specified in the publication
1.6e-05
-
NSC637992
-
pH and temperature not specified in the publication
9e-06
-
NSC637993
-
pH and temperature not specified in the publication
0.000597
-
NSC637994
-
pH and temperature not specified in the publication
0.0038
-
NSC640353
-
in 50 mM phosphate buffer at pH 7.4, at 37C
-
0.006
-
NSC640556
-
in 50 mM phosphate buffer at pH 7.4, at 37C
-
0.0058
-
NSC640558
-
in 50 mM phosphate buffer at pH 7.4, at 37C
-
0.0065
-
NSC640559
-
in 50 mM phosphate buffer at pH 7.4, at 37C
-
0.0053
-
NSC640566
-
in 50 mM phosphate buffer at pH 7.4, at 37C
-
0.0032
-
NSC640583
-
in 50 mM phosphate buffer at pH 7.4, at 37C
-
0.0049
-
NSC640584
-
in 50 mM phosphate buffer at pH 7.4, at 37C
-
0.000296
-
NSC645808
-
pH and temperature not specified in the publication
0.000148
-
NSC645809
-
pH and temperature not specified in the publication
0.000953
-
NSC645811
-
pH and temperature not specified in the publication
0.001
-
NSC645812
-
pH and temperature not specified in the publication
0.000427
-
NSC645831
-
pH and temperature not specified in the publication
0.00083
-
NSC645833
-
pH and temperature not specified in the publication
0.000323
-
NSC645834
-
pH and temperature not specified in the publication
0.000693
-
NSC645835
-
pH and temperature not specified in the publication
0.000172
-
NSC645836
-
pH and temperature not specified in the publication
0.0035
-
NSC649091
-
in 50 mM phosphate buffer at pH 7.4, at 37C
-
9.9e-05
-
NSC660838
-
pH and temperature not specified in the publication
-
1.7e-05
-
NSC660839
-
pH and temperature not specified in the publication
3.1e-05
-
NSC660840
-
pH and temperature not specified in the publication
6e-06
-
NSC660841
-
pH and temperature not specified in the publication
0.0058
-
NSC66167
-
in 50 mM phosphate buffer at pH 7.4, at 37C
-
0.0096
-
NSC665126
-
in 50 mM phosphate buffer at pH 7.4, at 37C
-
0.002
-
NSC669977
-
in 50 mM phosphate buffer at pH 7.4, at 37C
-
0.0097
-
NSC676468
-
in 50 mM phosphate buffer at pH 7.4, at 37C
-
0.0029
-
NSC677939
-
in 50 mM phosphate buffer at pH 7.4, at 37C
-
0.0017
-
NSC693571
-
in 50 mM phosphate buffer at pH 7.4, at 37C
-
0.005
-
NSC720622
-
in 50 mM phosphate buffer at pH 7.4, at 37C
-
0.0018
-
NSC77833
-
in 50 mM phosphate buffer at pH 7.4, at 37C
-
0.0021
-
NSC78017
-
in 50 mM phosphate buffer at pH 7.4, at 37C
-
0.0055
-
NSC78021
-
in 50 mM phosphate buffer at pH 7.4, at 37C
-
0.0021
-
NSC86715
-
in 50 mM phosphate buffer at pH 7.4, at 37C
-
0.0027
-
NSC97374
-
in 50 mM phosphate buffer at pH 7.4, at 37C
-
0.0051
-
NSC99495
-
in 50 mM phosphate buffer at pH 7.4, at 37C
-
0.006
-
NSC99528
-
in 50 mM phosphate buffer at pH 7.4, at 37C
-
0.0014
-
quercetin
-
IC50: 0.0014 mM
0.0015
-
quercetin-3-O-beta-glucopyranosyl
-
IC50: 0.0015 mM
0.000129
-
resveratrol
-
using nicotinamide riboside and menadione as substrates, at 25C, in 50 mM Tris-HCl, pH 8.5
0.000143
-
resveratrol
-
using N-benzyl dihydronicotinamide and menadione as substrates, at 25C, in 50 mM Tris-HCl, pH 8.5
0.00096
-
resveratrol
-
pH 8, 25C
0.00096
-
resveratrol
-
23C
0.0029
-
resveratrol
-
using nicotinamide riboside and coenzyme Q2 as substrates, at 25C, in 50 mM Tris-HCl, pH 8.5
0.07
-
resveratrol
-
using N-benzyl dihydronicotinamide and coenzyme Q2 as substrates, at 25C, in 50 mM Tris-HCl, pH 8.5
0.0012
-
S26695
-
using nicotinamide riboside and menadione as substrates, at 25C, in 50 mM Tris-HCl, pH 8.5
-
0.0025
-
S26695
-
using N-benzyl dihydronicotinamide and coenzyme Q2 as substrates, at 25C, in 50 mM Tris-HCl, pH 8.5
-
0.0126
-
S26695
-
using nicotinamide riboside and coenzyme Q2 as substrates, at 25C, in 50 mM Tris-HCl, pH 8.5
-
0.0151
-
S26695
-
using N-benzyl dihydronicotinamide and menadione as substrates, at 25C, in 50 mM Tris-HCl, pH 8.5
-
0.00091
-
S28128
-
IC50: 0.00091 mM
7e-07
-
S29434
-
using nicotinamide riboside and menadione as substrates, at 25C, in 50 mM Tris-HCl, pH 8.5
-
5e-06
-
S29434
-
using nicotinamide riboside and coenzyme Q2 as substrates, at 25C, in 50 mM Tris-HCl, pH 8.5
-
6.7e-06
-
S29434
-
using N-benzyl dihydronicotinamide and menadione as substrates, at 25C, in 50 mM Tris-HCl, pH 8.5
-
7.9e-05
-
S29434
-
using N-benzyl dihydronicotinamide and coenzyme Q2 as substrates, at 25C, in 50 mM Tris-HCl, pH 8.5
-
SPECIFIC ACTIVITY [µmol/min/mg]
SPECIFIC ACTIVITY MAXIMUM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
242
-
-
-
additional information
-
-
-
pH OPTIMUM
pH MAXIMUM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
7.5
-
-
assay at
8.5
-
-
assay at
TEMPERATURE OPTIMUM
TEMPERATURE OPTIMUM MAXIMUM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
25
-
-
assay at
25
-
-
-
25
-
-
assay at
30
-
-
assay at
37
-
-
assay at
SOURCE TISSUE
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
SOURCE
-
no significant difference in expression in normal and malignant biliary tissue. Activity of NQO2 is significatly lower than in hepatocellular tissue
Manually annotated by BRENDA team
-
minimal expression
Manually annotated by BRENDA team
P16083
modest level
Manually annotated by BRENDA team
P16083
; high expression level
Manually annotated by BRENDA team
-
in normal hepatocellular tissue, the two NQO isoforms are differentially regulated with a higher expression of NQO2 than NQO1. In malignant hepatocellular tissue NQO1 is up-regulated and NQO2 is down-regulated
Manually annotated by BRENDA team
-
the high NQO2 activity of intraperitoneal ovarian metastases relative to other tissues indicates a potential for tretazicar therapy in the treatment of this disease
Manually annotated by BRENDA team
-
minimal expression
Manually annotated by BRENDA team
P16083
high expression level
Manually annotated by BRENDA team
-
highest expression
Manually annotated by BRENDA team
-
suppression of vascular smooth muscle cell proliferation mediated by resveratrol correlates with vascular smooth muscle cell downregulation
Manually annotated by BRENDA team
additional information
P16083
no expression in placenta
Manually annotated by BRENDA team
additional information
-
no expression in skeletal muscle
Manually annotated by BRENDA team
additional information
-
no activity in placenta
Manually annotated by BRENDA team
additional information
-
no activity in blood plasma
Manually annotated by BRENDA team
additional information
-
QR2 is overexpressed in neurodegenerative diseases
Manually annotated by BRENDA team
LOCALIZATION
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
GeneOntology No.
LITERATURE
SOURCE
PDB
SCOP
CATH
ORGANISM
MOLECULAR WEIGHT
MOLECULAR WEIGHT MAXIMUM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
40000
-
-
gel filtration
50000
-
-
gel filtration
SUBUNITS
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
?
-
x * 24600, SDS-PAGE
dimer
-
2 * 26000, SDS-PAGE
dimer
-
-
homodimer
-
the enzyme forms homodimers with two independent and equivalent active sites each containing a FAD cofactor
homodimer
-
-
Crystallization/COMMENTARY
ORGANISM
UNIPROT ACCESSION NO.
LITERATURE
2.1 A resolution
P16083
crystal structure of the enzyme in complex with resveratrol. Crystals of the native QR2 and QR2-resveratrol complex all belong to the P2(1)2(1)2(1) space group
-
purified NQO2 in complex with primaquine and chloroquine, hanging drop vapor diffusion method, against reservoirs containing 0.1 M HEPES, pH 7.5, and 1.3-2.0 M (NH4)2SO4, crystals of NQO2-CQ are soaked in 0.001 ml of reducing-soak solution consisting of 0.1 M HEPES, pH 7.5, 2.0 M (NH4)2SO4, 10 mM 1-(3-sulfonatopropyl)-3-carbamoyl-1,4-dihydropyrimidine and 1 mM chloroquine, X-ray diffraction structure determination and analysis at 1.2-1.4 A resolution
-
purified recombinant enzyme, hanging-drop, vapor-diffusion method, mixing of 0.001 ml of 4 mg/ml protein solution with 0.001 ml of reservoir solution containing 1.3-1.7 M ammonium sulfate, 0.1 M Bis-Tris buffer, pH 6.0-7.0, 0.1 M NaCl, 5 mM DTT, 0.012 mM FAD, and resveratrol, complexed with different inhibitors, X-ray diffraction structure determination and analysis at resolutions of 1.40-1.63 A
-
the crystal structure of melatonin and 2-iodomelatonin in complex with quinone reductase 2 provide a detailed description of the enzyme active site that can now be utilized in the design of new and potent inhibitors of the enzyme, hanging-drop vapour-diffusion method
-
X-ray crystal structure of NQO2 bound to imatinib to 1.75 A resolution. The X-ray structure provides an explanation for the binding specificity of NQO2 for imatinib and nilotinib, as well as for the effects of mutation of the reported phosphorylation sites on NQO2
-
X-ray crystallography studies of QR2 in complex with 6-methoxy-9-methyl-[1,3]dioxolo[4,5-h]quinolin-8(9H)-one
-
crystal structure of quinone reductase 2 in complexes with dopamine and adrenochrome
-
Purification/COMMENTARY
ORGANISM
UNIPROT ACCESSION NO.
LITERATURE
DEAE Sepharose, Superdex 75 column chromatography and Mono-Q column chromatography
-
Ni-NTA column chromatography
-
recombinant enzyme from Escherichia coli strain BL21(DE3)
-
recombinant His-tagged OR2 from Spodoptera frugiperda Sf9 cells by nickel affinity chromatography
-
Cloned/COMMENTARY
ORGANISM
UNIPROT ACCESSION NO.
LITERATURE
CHO-K1 cells transiently expressing the mutated form of hQR2
-
expressed in Escherichia coli
-
expressed in Hep-G2 cells
-
expression in CHO cells
-
expression in Escherichia coli strain BL21(DE3)
-
expression of His-tagged OR2 in Spodoptera frugiperda Sf9 cells
-
expression of recombinant QR2 in Spodoptera frugiperda Sf9 cells using the baculovirus transfection method
-
overexpression in Escherichia coli
-
the His-tagged enzyme is expressed in the Sf9 Spodoptera frugiperda ovarian cell line ATCC CRL-1711
-
expressed in Chinese hamster ovary cells and Escherichia coli
-
the mouse NQO2 cDNA is subcloned into the pMT2 eukaryotic expression vector which, upon transfection in monkey kidney COS1 cells, produce a significant increase in NQO2 activity. Deletion of 54 amino acids from the N-terminus of the mouse NQO2 protein results in the loss of NQO2 expression and activity in transfected COS1 cells
-
expressed in Sf9 insect cells
-
ENGINEERING
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
C222F
-
mutation, which is distant from the determined binding site of the ligand, increases the affinity of [125I]-iodo-5-methoxycarbonylamino-N-acetyltryptamine for the enzyme
F126Y
-
substitution of the hydrophobic residue by tyrosines at the active site significantly increases enzymatic activity and decreases the affinity of a structural analog of melatonin, 2-[125I]-iodo-5-methoxycarbonylamino-N-acetyltryptamine
F131M
-
mutant enzyme is more active than wild-type enzyme
F178Y
-
substitution of the hydrophobic residue by tyrosines at the active site significantly increases enzymatic activity and decreases the affinity of a structural analog of melatonin, 2-[125I]-iodo-5-methoxycarbonylamino-N-acetyltryptamine
H11F
-
mutation of residue in FAD binding site, the enzymatic activity is unchanged
H173Y
-
mutation of residues implicated in zinc chelating (His173 or His177) has no effect on radioligand binding
H177R
-
mutation of residues implicated in zinc chelating (His173 or His177) has no effect on radioligand binding
N161A
-
mutation, which is distant from the determined binding site of the ligand, increases the affinity of [125I]-iodo-5-methoxycarbonylamino-N-acetyltryptamine for the enzyme
N161H
-
results in the total loss of the enzymatic activity towards activation of 5-(aziridin-1-yl)-2,4-dinitrobenzamide, whereas the rates of reduction towards menadione are not altered
N18Q
-
mutation of residue in FAD binding site, the enzymatic activity is diminished
I128Y
-
substitution of the hydrophobic residue by tyrosines at the active site significantly increases enzymatic activity and decreases the affinity of a structural analog of melatonin, 2-[125I]-iodo-5-methoxycarbonylamino-N-acetyltryptamine
additional information
-
construction of a chimeric enzyme of the human NQO2 with 43 amino acids from the carboxyl terminus of human DT-diaphorase. HNQO2-hDT43 still uses dihydronicotinamide riboside as an electron donor. The chimeric enzyme is inhibited by quercetin but not dicoumarol
APPLICATION
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
medicine
-
anti-cancer therapy
medicine
-
the high NQO2 activity of intraperitoneal ovarian metastases relative to other tissues indicates a potential for tretazicar therapy in the treatment of this disease
medicine
-
estrogen quinones, including estradiol estradiol-3,4-quinone, generated by estrogen metabolism, are thought to be responsible for estrogen-initiated carcinogenesis. NQO2 could be a novel target for prevention of breast cancer initiation
medicine
-
quinone reductase 2 can play important roles in the regulation of catecholamine oxidation processes that may be involved in the etiology of Parkinson disease
medicine
-
QR2 inhibitors possibly represent a therapeutic strategy toward the treatment of learning deficits especially observed in the aged brain