1.10.5.1: ribosyldihydronicotinamide dehydrogenase (quinone)
This is an abbreviated version!
For detailed information about ribosyldihydronicotinamide dehydrogenase (quinone), go to the full flat file.
Word Map on EC 1.10.5.1
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1.10.5.1
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nadph:quinone
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resveratrol
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two-electron
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isoalloxazine
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medicine
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bnah
- 1.10.5.1
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nadph:quinone
- resveratrol
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two-electron
- isoalloxazine
- medicine
- bnah
Reaction
Synonyms
bQR2, dihydronicotinamide riboside:quinone oxidoreductase, dihydronicotinamide riboside:quinone oxidoreductase 2, dihydronicotinamide riboside:quinone reductase 2, EC 1.10.99.2, melatonin-binding site MT3, MT3, MT3/NQO2, N-ribosyldihydronicotinamide dehydrogenase (quinone), N-ribosyldihydronicotinamide:quinone oxidoreductase 2, NQO2, NRH-oxidizing enzyme, NRH:QR2, NRH:quinone oxidoreductase, NRH:quinone oxidoreductase 2, NRH:quinone oxireductase 2, NRH:quinone reductase 2, QR2, quinone oxidoreductase 2, quinone reductase 2, quinone reductase type 2
ECTree
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Inhibitors
Inhibitors on EC 1.10.5.1 - ribosyldihydronicotinamide dehydrogenase (quinone)
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1,2-dimethoxy-4-{(1Z)-3,3,3-trifluoro-2-[3-(trifluoromethyl)phenyl]prop-1-en-1-yl}benzene
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1,3-dimethoxy-5-[(1Z)-3,3,3-trifluoro-1-(4-methoxyphenyl)prop-1-en-2-yl]benzene
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1,4-dimethylphenanthrene
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0.00001 mM, 15% inhibition of the reaction with N1-(n-propyl)-nicotinamide
12-methylbenz[a]anthracene
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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
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IC50: 0.00087 mM
2-methoxy-6-((2-(6-methoxy-2-methylquinolin-4-yl)hydrazono)methyl)phenol
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3-{[4-(dihydroxyamino)phenoxy]methyl}-5-methoxy-1,2-dimethyl-1H-indole-4,7-dione
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4-(5-phenyl-1,3-oxazol-2-yl)benzene-1-carboximidamide
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inhibits the growth of Plasmodium falciparum with an IC50 value of 0.3 microM
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4-[(Z)-[(1H-imidazol-4-yl)methyl]diazenyl]-6-methoxy-2-methylquinoline
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5-(2-(dimethylamino)ethylamino)-6H-[1,2,3]triazolo[4,5,1-de]acridin-6-one
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5-(2-(dimethylamino)ethylamino)-6H-[1,2,3]triazolo[4,5,1-de]acridin-6-one N-oxide
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5-(2-(dimethylamino)ethylamino)-8-bromo-6H-[1,2,3]triazolo[4,5,1-de]acridin-6-one
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5-(2-(dimethylamino)ethylamino)-8-bromo-6H-[1,2,3]triazolo[4,5,1-de]acridin-6-one N-oxide
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5-(2-(dimethylamino)ethylamino)-8-fluoro-6H-[1,2,3]triazolo[4,5,1-de]acridin-6-one
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5-(2-(dimethylamino)ethylamino)-8-methoxy-6H-[1,2,3]triazolo[4,5,1-de]acridin-6-one
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5-(2-(dimethylamino)ethylamino)-8-methoxy-6H-[1,2,3]triazolo[4,5,1-de]acridin-6-one N-oxide
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5-(3-hydroxypropylamino)-8-bromo-6H-[1,2,3]triazolo[4,5,1-de]acridin-6-one
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5-(3-hydroxypropylamino)-8-methoxy-6H-[1,2,3]triazolo[4,5,1-de]acridin-6-one
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5-[(4-aminobutyl)amino]-1,2-dimethyl-3-[(2,4,6-trifluorophenoxy)methyl]-1H-indole-4,7-dione
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5-[(4-aminobutyl)amino]-1,2-dimethyl-3-[(4-nitrophenoxy)methyl]-1H-indole-4,7-dione
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5-[(8-aminooctyl)amino]-1,2-dimethyl-3-[(2,4,6-trifluorophenoxy)methyl]-1H-indole-4,7-dione
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5-[butyl(methyl)amino]-1,2-dimethyl-3-[(2,4,6-trifluorophenoxy)methyl]-1H-indole-4,7-dione
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5-[[4-(diethylamino)butyl]amino]-10-methoxy-6H-imidazo[4,5,1-de]acridin-6-one
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5-[[4-(diethylamino)butyl]amino]-7,10-dimethoxy-6H-imidazo[4,5,1-de]acridin-6-one
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5-[[4-(diethylamino)butyl]amino]-7-hydroxy-10-methoxy-6H-imidazo[4,5,1-de]acridin-6-one
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5-[[4-(diethylamino)butyl]amino]-7-hydroxy-8,9-dimethoxy-6H-imidazo[4,5,1-de]acridin-6-one
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most potent inhibitor of NQO2
5-[[4-(diethylamino)butyl]amino]-8-hydroxy-1-methyl-6H-imidazo[4,5,1-de]acridin-6-one
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5-[[4-(diethylamino)butyl]amino]-8-hydroxy-6H-imidazo[4,5,1-de]acridin-6-one
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5-[[4-(diethylamino)butyl]amino]-8-methoxy-1-methyl-6H-imidazo[4,5,1-de]acridin-6-one
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5-[[4-(diethylamino)butyl]amino]-8-methoxy-6H-imidazo[4,5,1-de]acridin-6-one
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5-[[4-(diethylamino)butyl]amino]-9-hydroxy-6H-imidazo[4,5,1-de]acridin-6-one
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5-[[4-(dimethylamino)butyl]amino]-1-methyl-6H-imidazo[4,5,1-de]acridin-6-one
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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)methyl]-1H-indole-4,7-dione
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7,12-dimethylbenz[a]anthracene
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0.00001 mM, 51% inhibition of the reaction with N1-(n-propyl)-nicotinamide
7-methylbenz[a]anthracene
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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
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9,10-dimethylanthracene
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0.00001 mM, 25% inhibition of the reaction with N1-(n-propyl)-nicotinamide
9-methylanthracene
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0.00001 mM, 26% inhibition of the reaction with N1-(n-propyl)-nicotinamide
benz[a]anthracene
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0.00001 mM, 40% inhibition of the reaction with N1-(n-propyl)-nicotinamide
curcumol
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curcumol directly targets NQO2 to cause reactive oxygen species generation, which triggers endoplasmic reticulum stress-C/EBP homologous protein death receptor signaling, sensitizing non-small cell lung cancer cells to tumor-necrosis-factor-related apoptosis-inducing ligand (TRAIl) induced apoptosis. Presence of curcumol increases thermal stability of NQO2. Residue Phe178 in NQO2 is a critical site for curcumol binding
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dabigatran
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specific binding to the enzyme, protein interaction analysis, overview
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
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ethyl N-[(2-{[(4-carbamimidoylphenyl)amino]methyl}-1H-benzimidazol-5-yl)carbonyl]-N-pyridin-2-yl-b-alaninate
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methyl 2-((S)-1-cyclohexyl-2-((R)-2-(4-(4-(4-nitrophenylsulfonamido)butylcarbamoyl)benzylcarbamoyl)-azetidin-1-yl)-2-oxoethylamino)acetate
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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
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N,N'-[methylenedi(4,1-phenylene)]diacetamide
compound is inhibitory, and binding increases the thermal stability of NQO2
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N-[2-(2-iodo-5-methoxy-1-methyl-4-nitroindol-3-yl)ethyl]acetamide
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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
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IC50: 14 nM
N-[2-(2-methoxy-6H-pyrido[2',3':4,5]pyrrolo[2,1-a]isoindol-11-yl)ethyl]2-furamide
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IC50: 0.0002 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
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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
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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
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N1-[2-(2-methoxy-6H-pyrido[2',3':4,5]pyrrolo[2,1-a]isoindol-11-yl)ethyl]-acetamide
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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
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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
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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
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NSC180969
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i.e. 7,8-dimethoxy-4-(3,4,5-trimethoxyphenyl)-1,2-dihydro-3H-benzo[e]isoindol-3-one
NSC187208
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i.e. N4-(7-chloro-4-quinolinyl)-N1,N1-diethyl-1,4-pentanediamine, chloroquine
NSC204996
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i.e. 7,8-dimethoxy-4-(3,4,5-trimethoxyphenyl)-2,3-dihydro-1H-benzo[e]isoindole
NSC238146
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i.e. N4-(6-((6-amino-2-methyl-4-quinolinyl)amino)hexyl)-2-methyl-4,6-quinolinediamine acetate
NSC300853
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i.e. 3-amino-9-ethyl-2-((4-(hydroxy(oxido)amino)phenyl)diazenyl)-9H-carbazole
NSC306843
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i.e. 1-methyl-4(1H)-quinolinone (1-methyl-4(1H)-quinolinylidene)hydrazone
NSC356819
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i.e. 4-((2-hydroxy-5-(phenyldiazenyl)phenyl)diazenyl)benzenecarboximidamide
NSC356820
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i.e. 4-((2-hydroxy-5-(2-phenylvinyl)phenyl)diazenyl)benzenecarboximidamide
NSC359466
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i.e. 4-((4-(amino(imino)methyl)phenyl)diazenyl)-3-hydroxy-N-phenyl-2-naphthamide
NSC621351
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i.e. 2-(2-fluorophenyl)-4-(2-naphthyl)-2,3-dihydro-1,5-benzothiazepine
NSC623234
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i.e. 3-chloro-3-(3,4-dimethoxyphenyl)-2-(3,4,5-trimethoxyphenyl)acrylaldehyde
NSC640353
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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
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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
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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
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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
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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
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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
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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
NSC649091
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i.e. 2-((diethylamino)methyl)-4-((10-methyl-10H-indolo[3,2-b]quinolin-11-yl)amino)phenol hydrochloride
NSC665126
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i.e. 1-(2-(4-(hydroxy(oxido)amino)phenyl)vinyl)-3-phenylbenzo[f]quinoline
NSC669977
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i.e. 6-imino-1-methyl-3-phenyl-2,6-dihydro-5(1H)-quinolinone hydrazone
NSC676468
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i.e. N-(3-([1,10-biphenyl]-4-ylimino)-1-propenyl)[1,10-biphenyl]-4-amine
NSC693571
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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
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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
NSC97374
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i.e. 1-ethyl-2-((1-ethyl-2(1H)-quinolinylidene)methyl)-1lambda5-quinoline
tert-butyl (S)-1-cyclohexyl-2-((R)-2-(4-(4-(4-nitrophenylsulfonamido)butylcarbamoyl)benzylcarbamoyl)-azetidin-1-yl)-2-oxoethylcarbamate
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Chloroquine
binds preferentially to reduced NQO2, binding mode, closure of a flexible loop (Phe126-Leu136) over the active site, overview
the structure of the imatinib-NQO2 complex demonstrates that imatinib inhibits NQO2 activity by competing with substrate for the active site
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
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QR2 is inhibited in the micromolar range by melatonin, but not when using N-benzyl dihydronicotinamide and coenzyme Q2 are used as substrates
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
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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
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i.e. N-methyl-[1-[2-(acetylamino)ethyl]naphthalen-7-yl]-carbamate
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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
additional information
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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
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additional information
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enzyme inhibitor design, synthesiis, and evaluation, inhibitory potencies of resveratrol analogues, overview. Inhibitor binding structure, modelling, overview
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additional information
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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
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additional information
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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
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additional information
study on 4-aminoquinoline hydrazone inhibitors. A small substituent at the 2-position of the 4-aminoquinoline ring is important to reduce steric hindrance and improve engagement of the scaffold within the NQO2 active site. Both the hydrazone and hydrazide derivatives are functionally active as inhibitors of NQO2 in the cells
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additional information
not inhibited by dicoumarol, Cibacron blue, phenindone
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additional information
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not inhibited by dicoumarol, Cibacron blue, phenindone
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