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Literature summary extracted from

  • Michaelis, S.; Marais, A.; Schrey, A.K.; Graebner, O.Y.; Schaudt, C.; Sefkow, M.; Kroll, F.; Dreger, M.; Glinski, M.; Koester, H.; Metternich, R.; Fischer, J.J.
    Dabigatran and dabigatran ethyl ester: potent inhibitors of ribosyldihydronicotinamide dehydrogenase (NQO2) (2012), J. Med. Chem., 55, 3934-3944.
    View publication on PubMed

Inhibitors

EC Number Inhibitors Comment Organism Structure
1.10.5.1 dabigatran specific binding to the enzyme, protein interaction analysis, overview Homo sapiens
1.10.5.1 dabigatran ethyl ester
-
 Homo sapiens
1.10.5.1 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
-
 Homo sapiens
1.10.5.1 ethyl N-[(2-{[(4-carbamimidoylphenyl)amino]methyl}-1H-benzimidazol-5-yl)carbonyl]-N-pyridin-2-yl-b-alaninate
-
 Homo sapiens
1.10.5.1 imatinib
-
 Homo sapiens
1.10.5.1 melagatran
-
 Homo sapiens
1.10.5.1 methyl 2-((S)-1-cyclohexyl-2-((R)-2-(4-(4-(4-nitrophenylsulfonamido)butylcarbamoyl)benzylcarbamoyl)-azetidin-1-yl)-2-oxoethylamino)acetate
-
 Homo sapiens
1.10.5.1 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
-
 Homo sapiens
1.10.5.1 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 Homo sapiens
1.10.5.1 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
-
 Homo sapiens
1.10.5.1 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
-
 Homo sapiens
1.10.5.1 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
-
 Homo sapiens
1.10.5.1 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
-
 Homo sapiens
1.10.5.1 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
-
 Homo sapiens
1.10.5.1 resveratrol
-
 Homo sapiens
1.10.5.1 tert-butyl (S)-1-cyclohexyl-2-((R)-2-(4-(4-(4-nitrophenylsulfonamido)butylcarbamoyl)benzylcarbamoyl)-azetidin-1-yl)-2-oxoethylcarbamate
-
 Homo sapiens
1.10.5.1 tert-butyl 4-(4-(4-nitrophenylsulfonamido)butylcarbamoyl)-benzylcarbamate
-
 Homo sapiens

Natural Substrates/ Products (Substrates)

EC Number Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
1.10.5.1 1-(beta-D-ribofuranosyl)-1,4-dihydronicotinamide + a quinone Homo sapiens
-
 1-(beta-D-ribofuranosyl)nicotinamide + a hydroquinone
-
 ?
1.10.5.1 1-(beta-D-ribofuranosyl)-1,4-dihydronicotinamide + menadione Homo sapiens
-
 1-(beta-D-ribofuranosyl)nicotinamide + menadiol
-
 ?

Organism

EC Number Organism UniProt Comment Textmining
1.10.5.1 Homo sapiens
-
-
-

Source Tissue

EC Number Source Tissue Comment Organism Textmining
1.10.5.1 Hep-G2 cell
-
 Homo sapiens
-
1.10.5.1 K-562 cell
-
 Homo sapiens
-

Substrates and Products (Substrate)

EC Number Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
1.10.5.1 1-(beta-D-ribofuranosyl)-1,4-dihydronicotinamide + a quinone
-
 Homo sapiens 1-(beta-D-ribofuranosyl)nicotinamide + a hydroquinone
-
 ?
1.10.5.1 1-(beta-D-ribofuranosyl)-1,4-dihydronicotinamide + menadione
-
 Homo sapiens 1-(beta-D-ribofuranosyl)nicotinamide + menadiol
-
 ?

Synonyms

EC Number Synonyms Comment Organism
1.10.5.1 NQO2
-
 Homo sapiens

Cofactor

EC Number Cofactor Comment Organism Structure
1.10.5.1 FAD
-
 Homo sapiens

Ki Value [mM]

EC Number Ki Value [mM] Ki Value maximum [mM] Inhibitor Comment Organism Structure
1.10.5.1 additional information
-
 additional information Michaelis-Menten inhibition kinetics Homo sapiens
1.10.5.1 0.0009
-
 dabigatran ethyl ester pH and temperature not specified in the publication Homo sapiens
1.10.5.1 0.07
-
 dabigatran pH and temperature not specified in the publication Homo sapiens

IC50 Value

EC Number IC50 Value IC50 Value Maximum Comment Organism Inhibitor Structure
1.10.5.1 0.0008
-
 pH and temperature not specified in the publication Homo sapiens dabigatran ethyl ester
1.10.5.1 0.06
-
 pH and temperature not specified in the publication Homo sapiens dabigatran

General Information

EC Number General Information Comment Organism
1.10.5.1 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 Homo sapiens