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Information on EC 1.10.5.1 - ribosyldihydronicotinamide dehydrogenase (quinone)
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1.10.5.1 ribosyldihydronicotinamide dehydrogenase (quinone)IUBMB Comments
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 estrogens 17beta-estradiol and diethylstilbestrol are potent inhibitors, but dicoumarol is only a very weak inhibitor . This enzyme can catalyse both 2-electron and 4-electron reductions, but one-electron acceptors, such as potassium ferricyanide, cannot be reduced .
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The expected taxonomic range for this enzyme is: Bacteria, Eukaryota
Reaction Schemes
Synonyms
quinone reductase 2, nrh:quinone oxidoreductase 2, quinone oxidoreductase 2, quinone reductase type 2, nrh:quinone oxidoreductase, dihydronicotinamide riboside:quinone oxidoreductase, dihydronicotinamide riboside:quinone reductase 2, dihydronicotinamide riboside:quinone oxidoreductase 2, 
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SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
melatonin-binding site MT3
NQO2
NRH:quinone oxidoreductase
NRH:quinone oxidoreductase 2
NRH:quinone reductase 2
QR2
quinone reductase 2
quinone reductase type 2
NQO2
-
-
NRH:quinone oxidoreductase 2
-
-
QR2
-
-
quinone reductase 2
-
-
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
1-(beta-D-ribofuranosyl)-1,4-dihydronicotinamide + a quinone = 1-(beta-D-ribofuranosyl)nicotinamide + a quinol
-
-
-
-
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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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 estrogens 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].
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CAS REGISTRY NUMBER
COMMENTARY
667919-86-0
-
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SUBSTRATE
PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
1-(beta-D-ribofuranosyl)-1,4-dihydronicotinamide + a quinone
1-(beta-D-ribofuranosyl)nicotinamide + a hydroquinone
-
-
-
-
?
1-(beta-D-ribofuranosyl)-1,4-dihydronicotinamide + a quinone
1-(beta-D-ribofuranosyl)nicotinamide + a quinol
-
-
-
?
1-(beta-D-ribofuranosyl)-1,4-dihydronicotinamide + co-enzyme Q
1-(beta-D-ribofuranosyl)nicotinamide + reduced co-enzyme Q
-
natural substrate nicotinamide riboside, NRH
-
-
?
1-(beta-D-ribofuranosyl)-1,4-dihydronicotinamide + menadione
1-(beta-D-ribofuranosyl)nicotinamide + menadiol
1-(carbamoylmethyl)dihydronicotinamide + 3-hydroxy-1-methylindoline-5,6-dione
1-(carbamoylmethyl)nicotinamide + 3-hydroxy-1-methylindoline-5,6-diol
-
3-hydroxy-1-methylindoline-5,6-dione i.e. adrenochrome
-
-
?
1-benzyl-1,4-dihydronicotinamide + estradiol-3,4-quinone
1-benzyl-3-carbamoylpyridinium + estrone-3,4-quinone
-
-
-
-
r
1-carbamoylmethyl-3-carbamoyl-1,4-dihydropyrimidine + menadione
1-carbamoylmethyl-3-carbamoylpyrimidine + menadiol
-
-
-
?
17beta-17-hydroxyestr-1(10)-ene-3,4-dione + N-benzyldihydronicotinamide
17beta-estra-1(10),2,4-triene-3,4,17-triol + N-benzylnicotinamide
-
ping-pong mechanism, NQO2 is faster in reducing estrogen quinones than its homologue NQO1
-
-
?
2H-dibenzo[b,f]azepin-2-one + dihydronicotinamide riboside
? + nicotinamide riboside
-
-
-
?
5-(aziridin-1-yl)-2,4-dinitrobenzamide + dihydronicotinamide riboside
? + nicotinamide riboside
-
-
-
?
5-(aziridin-1-yl)-2,4-dinitrobenzamide + menadiol
? + reduced menadiol
-
-
-
-
?
amodiaquine quinone imine + dihydronicotinamide riboside
? + nicotinamide riboside
-
-
-
?
benzo(a)pyrene-3,6-quinone + dihydronicotinamide riboside
? + nicotinamide riboside
-
-
-
?
desethylamodiaquine quinone imine + dihydronicotinamide riboside
? + nicotinamide riboside
-
-
-
?
diclofenac-1',4'-quinone imine + dihydronicotinamide riboside
? + nicotinamide riboside
-
-
-
?
diclofenac-2,5-quinone imine + dihydronicotinamide riboside
? + nicotinamide riboside
-
-
-
?
dihydronicotinamide riboside + 2,6-dichlorophenolindophenol
nicotinamide riboside + reduced 2,6-dichlorophenolindophenol
-
-
-
-
?
dihydronicotinamide riboside + 3-(4,5-dimethylthiazaol-2-yl)-2,5-diphenyltetrazolium
nicotinamide riboside + ?
-
-
-
-
?
dihydronicotinamide riboside + menadione
ribosyl nicotinamide + menadiol
-
-
-
-
?
dihydronicotinamide riboside + menadione/3-(4,5-dimethylthiazaol-2-yl)-2,5-diphenyltetrazolium
nicotinamide riboside + ?
-
-
-
-
?
estrone-3,4-quinone + N-benzyldihydronicotinamide
estrone-3,4-quinol + N-benzylnicotinamide
-
ping-pong mechanism, NQO2 is faster in reducing estrogen quinones than its homologue NQO1
-
-
?
mefenamic acid-1',4'-quinone imine + dihydronicotinamide riboside
? + nicotinamide riboside
-
-
-
?
mefenamic acid-2,5-quinone imine + dihydronicotinamide riboside
? + nicotinamide riboside
-
-
-
?
menadione + dihydronicotinamide riboside
menadiol + nicotinamide riboside
-
-
-
?
mitomycin C + dihydronicotinamide riboside
? + nicotinamide riboside
-
-
-
?
N-acetyl-p-benzoquinone imine + dihydronicotinamide riboside
? + nicotinamide riboside
-
-
-
?
N-benzyldihydronicotinamide + 2,6-dichlorophenolindophenol
N-benzylnicotamide + reduced 2,6-dichlorophenolindophenol
-
-
-
?
N-benzyldihydronicotinamide + 2,6-dichlorophenolindophenol
N-benzylnicotinamide + reduced 2,6-dichlorophenolindophenol
-
-
-
-
?
N-benzyldihydronicotinamide + a quinone
N-benzylnicotinamide + a hydroquinone
-
synthetic substrate
-
-
?
N-benzyldihydronicotinamide + menadione
N-benzylnicotamide + menadiol
-
-
-
-
?
N-benzyldihydronicotinamide + menadione
N-benzylnicotinamide + menadiol
-
-
-
-
?
N-benzyldihydronicotinamide + oxidized coenzyme Q0
N-benzylnicotinamide + reduced coenzyme Q20
-
-
-
-
?
N-benzyldihydronicotinamide + oxidized coenzyme Q1
N-benzylnicointamide + reduced coenzyme Q1
-
-
-
-
?
N-benzyldihydronicotinamide + oxidized coenzyme Q2
N-benzylnicotinamide + reduced coenzyme Q2
-
-
-
-
?
N-methyldihydronicotinamide + 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide
N-methylnicotinamide + ?
-
-
-
-
?
N-methyldihydronicotinamide + 3-hydroxy-1-methylindoline-5,6-dione
N-methylnicotinamide + 3-hydroxy-1-methylindoline-5,6-diol
-
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-ribosylnicotinamide + menadiol
?
-
N-ribosylnicotinamide is a poor substrate
-
-
?
nicotinamide riboside + menadiol
dihydronicotinamide riboside + menadione
-
-
-
-
?
nicotinamide riboside + reduced 2,6-dichlorophenolindophenol
dihydronicotinamide riboside + 2,6-dichlorophenolindophenol
-
-
-
-
?
nicotinamide riboside + reduced coenzyme Q0
dihydronicotinamide riboside + coenzyme Q0
-
-
-
-
?
nicotinamide riboside + reduced coenzyme Q1
dihydronicotinamide riboside + coenzyme Q1
-
-
-
-
?
nicotinamide riboside + reduced coenzyme Q2
dihydronicotinamide riboside + coenzyme Q2
-
-
-
-
?
reduced N1-(benzyl)-nicotinamide + menadione
N1-(benzyl)-nicotinamide + menadiol
-
-
-
-
?
reduced N1-(methyl)-nicotinamide + menadione
N1-(methyl)-nicotinamide + reduced menadiol
-
-
-
-
?
reduced N1-(n-propyl)-nicotinamide + menadione
N1-(n-propyl)-nicotinamide + menadiol
-
-
-
-
?
1-(beta-D-ribofuranosyl)-1,4-dihydronicotinamide + menadione
1-(beta-D-ribofuranosyl)nicotinamide + menadiol
-
-
-
-
?
1-(beta-D-ribofuranosyl)-1,4-dihydronicotinamide + menadione
1-(beta-D-ribofuranosyl)nicotinamide + menadiol
-
natural substrate nicotinamide riboside, NRH
-
-
?
2,6-dichloroindophenol + dihydronicotinamide riboside
? + nicotinamide riboside
-
-
-
?
2,6-dichloroindophenol + dihydronicotinamide riboside
? + nicotinamide riboside
-
-
-
?
N-methyldihydronicotinamide + menadione
N-methylnicotinamide + menadiol
-
-
-
-
?
N-methyldihydronicotinamide + menadione
N-methylnicotinamide + menadiol
-
-
-
?
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
?
-
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
?
-
knockdown K562 cells exhibit increased antioxidant and detoxification enzyme expression and reduced proliferation rates
-
-
?
additional information
?
-
-
the expression of the NQO2 gene is induced in response to 2,3,7,8-tetrachlorodibenzo-p-dioxin
-
-
?
additional information
?
-
enzyme cannot use NADH or NADPH as reducing agent
-
-
?
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
?
-
-
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
-
-
?
additional information
?
-
-
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)
-
-
?
additional information
?
-
no substrate: 5-hydroxydiclofenac quinone imine
-
-
-
additional information
?
-
-
no substrate: 5-hydroxydiclofenac quinone imine
-
-
-
additional information
?
-
-
enzyme exhibits melatonin-binding activity
-
-
?
additional information
?
-
-
by deleting QR2 it seems that mice become increasingly susceptible to polycyclic aromatic hydrocarbon-induced skin carcinogenesis
-
-
?
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
?
-
-
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
-
-
?
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NATURAL SUBSTRATE
NATURAL PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
1-(beta-D-ribofuranosyl)-1,4-dihydronicotinamide + a quinone
1-(beta-D-ribofuranosyl)nicotinamide + a hydroquinone
-
-
-
-
?
1-(beta-D-ribofuranosyl)-1,4-dihydronicotinamide + a quinone
1-(beta-D-ribofuranosyl)nicotinamide + a quinol
-
-
-
?
1-(beta-D-ribofuranosyl)-1,4-dihydronicotinamide + co-enzyme Q
1-(beta-D-ribofuranosyl)nicotinamide + reduced co-enzyme Q
-
natural substrate nicotinamide riboside, NRH
-
-
?
1-(beta-D-ribofuranosyl)-1,4-dihydronicotinamide + menadione
1-(beta-D-ribofuranosyl)nicotinamide + menadiol
1-(beta-D-ribofuranosyl)-1,4-dihydronicotinamide + menadione
1-(beta-D-ribofuranosyl)nicotinamide + menadiol
-
-
-
-
?
1-(beta-D-ribofuranosyl)-1,4-dihydronicotinamide + menadione
1-(beta-D-ribofuranosyl)nicotinamide + menadiol
-
natural substrate nicotinamide riboside, NRH
-
-
?
additional information
?
-
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
?
-
knockdown K562 cells exhibit increased antioxidant and detoxification enzyme expression and reduced proliferation rates
-
-
?
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
?
-
-
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
-
-
?
additional information
?
-
-
enzyme exhibits melatonin-binding activity
-
-
?
additional information
?
-
-
by deleting QR2 it seems that mice become increasingly susceptible to polycyclic aromatic hydrocarbon-induced skin carcinogenesis
-
-
?
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
?
-
-
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
-
-
?
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COFACTOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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
FAD
contains 1 FAD per monomer firmly bound to the enzyme through multiple interactions
FAD
-
mediates hydride transfer, very tightly bound to the enzyme. Activity of the purified enzyme is not further increased by added FAD
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
-
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
-
flavoenzyme, binding structure, overview. 2 molecules per enzyme dimer, quantification, overview
additional information
enzyme cannot use NADH or NADPH as reducing agent
-
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METALS and IONS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
1,2-dimethoxy-4-{(1Z)-3,3,3-trifluoro-2-[3-(trifluoromethyl)phenyl]prop-1-en-1-yl}benzene
-
-
1,3-dimethoxy-5-[(1Z)-3,3,3-trifluoro-1-(4-methoxyphenyl)prop-1-en-2-yl]benzene
-
-
1,4-dimethylphenanthrene
-
0.00001 mM, 15% inhibition of the reaction with N1-(n-propyl)-nicotinamide
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-methoxy-6-((2-(6-methoxy-2-methylquinolin-4-yl)hydrazono)methyl)phenol
-
-
3-{[4-(dihydroxyamino)phenoxy]methyl}-5-methoxy-1,2-dimethyl-1H-indole-4,7-dione
-
-
4-(5-phenyl-1,3-oxazol-2-yl)benzene-1-carboximidamide
-
inhibits the growth of Plasmodium falciparum with an IC50 value of 0.3 microM
-
4-[(Z)-[(1H-imidazol-4-yl)methyl]diazenyl]-6-methoxy-2-methylquinoline
-
-
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-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-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]-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-methyl-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
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-
5-[[4-(dimethylamino)butyl]amino]-8-hydroxy-6H-imidazo[4,5,1-de]acridin-6-one
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5-[[6-(diethylamino)hexyl]amino]-8-hydroxy-6H-imidazo[4,5,1-de]acridin-6-one
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5-{[2-(dimethylamino)ethyl]amino}-1,2-dimethyl-3-(phenoxymethyl)-1H-indole-4,7-dione
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5-{[2-(dimethylamino)ethyl]amino}-1,2-dimethyl-3-[(2,4,6-trifluorophenoxy)methyl]-1H-indole-4,7-dione
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5-{[2-(dimethylamino)ethyl]amino}-1-methyl-2-phenyl-3-[(2,4,6-trifluorophenoxy)methyl]-1H-indole-4,7-dione
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5-{[2-(dimethylamino)ethyl]amino}-1-methyl-3-[(2,4,6-trifluorophenoxy)methyl]-1H-indole-4,7-dione
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5-{[3-(dimethylamino)propyl]amino}-1,2-dimethyl-3-[(2,4,6-trifluorophenoxy)meth