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Literature summary extracted from

  • Nolan, K.A.; Doncaster, J.R.; Dunstan, M.S.; Scott, K.A.; Frenkel, A.D.; Siegel, D.; Ross, D.; Barnes, J.; Levy, C.; Leys, D.; Whitehead, R.C.; Stratford, I.J.; Bryce, R.A.
    Synthesis and biological evaluation of coumarin-based inhibitors of NAD(P)H: quinone oxidoreductase-1 (NQO1) (2009), J. Med. Chem., 52, 7142-7156.
    View publication on PubMed

Crystallization (Commentary)

EC Number Crystallization (Comment) Organism
1.6.5.2 in complex with 4-hydroxy-6,7-dimethyl-3-(1-naphthylmethyl)-2H-chromen-2-one, hanging drop vapor diffusion method, using 2.4 M ammonium sulfate and 0.1 M Tris buffer pH 8.5 Homo sapiens

Inhibitors

EC Number Inhibitors Comment Organism Structure
1.6.5.2 1-hydroxy-2-(1-naphthylmethyl)-3H-benzo[f]chromen-3-one
-
 Homo sapiens
1.6.5.2 1-hydroxy-2-(2-naphthylmethyl)-3H-benzo[f]chromen-3-one
-
 Homo sapiens
1.6.5.2 2-benzyl-1-hydroxy-3H-benzo[f]chromen-3-one
-
 Homo sapiens
1.6.5.2 3,3'-butane-1,1-diylbis(4-hydroxy-2H-chromen-2-one)
-
 Homo sapiens
1.6.5.2 3,3'-methanediylbis(4-hydroxy-2H-benzo[h]chromen-2-one)
-
 Homo sapiens
1.6.5.2 3,3'-methanediylbis(4-hydroxy-5-methoxy-2H-chromen-2-one)
-
 Homo sapiens
1.6.5.2 3,3'-methanediylbis(4-hydroxy-6,7-dimethoxy-2H-chromen-2-one)
-
 Homo sapiens
1.6.5.2 3,3'-methanediylbis(4-hydroxy-6,7-dimethyl-2H-chromen-2-one)
-
 Homo sapiens
1.6.5.2 3,3'-methanediylbis(4-hydroxy-6,8-dibromo-2H-chromen-2-one)
-
 Homo sapiens
1.6.5.2 3,3'-methanediylbis(4-hydroxy-6-chloro-2H-chromen-2-one)
-
 Homo sapiens
1.6.5.2 3,3'-methanediylbis(4-hydroxy-6-fluoro-2H-chromen-2-one)
-
 Homo sapiens
1.6.5.2 3,3'-methanediylbis(4-hydroxy-6-methoxy-2H-chromen-2-one)
-
 Homo sapiens
1.6.5.2 3,3'-methanediylbis(4-hydroxy-7,8-dimethyl-2H-chromen-2-one)
-
 Homo sapiens
1.6.5.2 3,3'-methanediylbis(4-hydroxy-7-fluoro-2H-chromen-2-one)
-
 Homo sapiens
1.6.5.2 3,3'-methanediylbis(4-hydroxy-7-methoxy-2H-chromen-2-one)
-
 Homo sapiens
1.6.5.2 3,3'-methylenebis(4-hydroxy-6-methyl-2H-chromen-2-one)
-
 Homo sapiens
1.6.5.2 3-(3,4-dimethylbenzyl)-4-hydroxy-2H-chromen-2-one
-
 Homo sapiens
1.6.5.2 3-(3,4-dimethylbenzyl)-4-hydroxy-6,7-dimethyl-2H-chromen-2-one
-
 Homo sapiens
1.6.5.2 3-benzyl-4-hydroxy-2H-benzo[h]chromen-2-one
-
 Homo sapiens
1.6.5.2 3-benzyl-4-hydroxy-2H-chromen-2-one
-
 Homo sapiens
1.6.5.2 3-benzyl-4-hydroxy-6,7-dimethyl-2H-chromen-2-one
-
 Homo sapiens
1.6.5.2 4-hydroxy-3-(1-naphthylmethyl)-2H-benzo[h]chromen-2-one
-
 Homo sapiens
1.6.5.2 4-hydroxy-3-(1-naphthylmethyl)-2H-chromen-2-one
-
 Homo sapiens
1.6.5.2 4-hydroxy-3-(2-naphthylmethyl)-2H-benzo[h]chromen-2-one
-
 Homo sapiens
1.6.5.2 4-hydroxy-3-(2-naphthylmethyl)-2H-chromen-2-one
-
 Homo sapiens
1.6.5.2 4-hydroxy-6,7-dimethyl-3-(1-naphthylmethyl)-2H-chromen-2-one
-
 Homo sapiens
1.6.5.2 4-hydroxy-6,7-dimethyl-3-(2-naphthylmethyl)-2H-chromen-2-one
-
 Homo sapiens
1.6.5.2 dicoumarol i.e. 3,3'-methylenebis(4-hydroxycoumarin), potent competitive inhibitor of NQO1 Homo sapiens
1.6.5.2 ethyl bis(4-hydroxy-2-oxo-2H-chromen-3-yl)acetate
-
 Homo sapiens

Organism

EC Number Organism UniProt Comment Textmining
1.6.5.2 Homo sapiens P15559
-
-

Source Tissue

EC Number Source Tissue Comment Organism Textmining
1.6.5.2 HCT-116 cell
-
 Homo sapiens
-
1.6.5.2 MiaPaCa-2 cell
-
 Homo sapiens
-

Substrates and Products (Substrate)

EC Number Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
1.6.5.2 NAD(P)H + H+ + oxidized 2,6-dichlorophenolindophenol
-
 Homo sapiens NAD(P)+ + reduced 2,6-dichlorophenolindophenol
-
 ?

Synonyms

EC Number Synonyms Comment Organism
1.6.5.2 DT-diaphorase
-
 Homo sapiens
1.6.5.2 EC 1.6.99.2 formerly Homo sapiens
1.6.5.2 NAD(P)H quinone oxidoreductase-1
-
 Homo sapiens
1.6.5.2 NAD(P)H: quinone oxidoreductase-1
-
 Homo sapiens
1.6.5.2 NQO1
-
 Homo sapiens

Cofactor

EC Number Cofactor Comment Organism Structure
1.6.5.2 NADH
-
 Homo sapiens
1.6.5.2 NADPH
-
 Homo sapiens

IC50 Value

EC Number IC50 Value IC50 Value Maximum Comment Organism Inhibitor Structure
1.6.5.2 0.00000018
-
 with 0.002 mM bovine serum albumin, in 50 mM phosphate buffer, at pH 7.5 and 25°C Homo sapiens 3,3'-methanediylbis(4-hydroxy-2H-benzo[h]chromen-2-one)
1.6.5.2 0.00000041
-
 without bovine serum albumin, in 50 mM phosphate buffer, at pH 7.5 and 25°C Homo sapiens 3,3'-methanediylbis(4-hydroxy-6,7-dimethyl-2H-chromen-2-one)
1.6.5.2 0.00000042
-
 without bovine serum albumin, in 50 mM phosphate buffer, at pH 7.5 and 25°C Homo sapiens 3,3'-methanediylbis(4-hydroxy-7,8-dimethyl-2H-chromen-2-one)
1.6.5.2 0.0000022
-
 without bovine serum albumin, in 50 mM phosphate buffer, at pH 7.5 and 25°C Homo sapiens 4-hydroxy-3-(2-naphthylmethyl)-2H-benzo[h]chromen-2-one
1.6.5.2 0.0000025
-
 without bovine serum albumin, in 50 mM phosphate buffer, at pH 7.5 and 25°C Homo sapiens 4-hydroxy-6,7-dimethyl-3-(2-naphthylmethyl)-2H-chromen-2-one
1.6.5.2 0.0000026
-
 without bovine serum albumin, in 50 mM phosphate buffer, at pH 7.5 and 25°C Homo sapiens dicoumarol
1.6.5.2 0.0000028
-
 without bovine serum albumin, in 50 mM phosphate buffer, at pH 7.5 and 25°C Homo sapiens 3,3'-methanediylbis(4-hydroxy-5-methoxy-2H-chromen-2-one)
1.6.5.2 0.0000038
-
 without bovine serum albumin, in 50 mM phosphate buffer, at pH 7.5 and 25°C Homo sapiens 3,3'-methanediylbis(4-hydroxy-7-fluoro-2H-chromen-2-one)
1.6.5.2 0.0000045
-
 without bovine serum albumin, in 50 mM phosphate buffer, at pH 7.5 and 25°C Homo sapiens 3,3'-methanediylbis(4-hydroxy-6-fluoro-2H-chromen-2-one)
1.6.5.2 0.0000049
-
 without bovine serum albumin, in 50 mM phosphate buffer, at pH 7.5 and 25°C Homo sapiens 3,3'-methanediylbis(4-hydroxy-6,8-dibromo-2H-chromen-2-one)
1.6.5.2 0.000006
-
 without bovine serum albumin, in 50 mM phosphate buffer, at pH 7.5 and 25°C Homo sapiens 3,3'-methanediylbis(4-hydroxy-7-methoxy-2H-chromen-2-one)
1.6.5.2 0.000006
-
 without bovine serum albumin, in 50 mM phosphate buffer, at pH 7.5 and 25°C Homo sapiens 1-hydroxy-2-(2-naphthylmethyl)-3H-benzo[f]chromen-3-one
1.6.5.2 0.0000063
-
 without bovine serum albumin, in 50 mM phosphate buffer, at pH 7.5 and 25°C Homo sapiens 4-hydroxy-3-(1-naphthylmethyl)-2H-benzo[h]chromen-2-one
1.6.5.2 0.0000063
-
 without bovine serum albumin, in 50 mM phosphate buffer, at pH 7.5 and 25°C Homo sapiens 1-hydroxy-2-(1-naphthylmethyl)-3H-benzo[f]chromen-3-one
1.6.5.2 0.0000077
-
 without bovine serum albumin, in 50 mM phosphate buffer, at pH 7.5 and 25°C Homo sapiens 4-hydroxy-6,7-dimethyl-3-(1-naphthylmethyl)-2H-chromen-2-one
1.6.5.2 0.000009
-
 without bovine serum albumin, in 50 mM phosphate buffer, at pH 7.5 and 25°C Homo sapiens 3,3'-methanediylbis(4-hydroxy-6-chloro-2H-chromen-2-one)
1.6.5.2 0.0000099
-
 without bovine serum albumin, in 50 mM phosphate buffer, at pH 7.5 and 25°C Homo sapiens 3-(3,4-dimethylbenzyl)-4-hydroxy-6,7-dimethyl-2H-chromen-2-one
1.6.5.2 0.000011
-
 without bovine serum albumin, in 50 mM phosphate buffer, at pH 7.5 and 25°C Homo sapiens 3,3'-methanediylbis(4-hydroxy-6-methoxy-2H-chromen-2-one)
1.6.5.2 0.000014
-
 without bovine serum albumin, in 50 mM phosphate buffer, at pH 7.5 and 25°C Homo sapiens 3,3'-methylenebis(4-hydroxy-6-methyl-2H-chromen-2-one)
1.6.5.2 0.000014
-
 without bovine serum albumin, in 50 mM phosphate buffer, at pH 7.5 and 25°C Homo sapiens 4-hydroxy-3-(2-naphthylmethyl)-2H-chromen-2-one
1.6.5.2 0.000015
-
 without bovine serum albumin, in 50 mM phosphate buffer, at pH 7.5 and 25°C Homo sapiens 2-benzyl-1-hydroxy-3H-benzo[f]chromen-3-one
1.6.5.2 0.000024
-
 without bovine serum albumin, in 50 mM phosphate buffer, at pH 7.5 and 25°C Homo sapiens 4-hydroxy-3-(1-naphthylmethyl)-2H-chromen-2-one
1.6.5.2 0.000031
-
 without bovine serum albumin, in 50 mM phosphate buffer, at pH 7.5 and 25°C Homo sapiens 3-(3,4-dimethylbenzyl)-4-hydroxy-2H-chromen-2-one
1.6.5.2 0.000035
-
 without bovine serum albumin, in 50 mM phosphate buffer, at pH 7.5 and 25°C Homo sapiens 3-benzyl-4-hydroxy-2H-benzo[h]chromen-2-one
1.6.5.2 0.000038
-
 with 0.002 mM bovine serum albumin, in 50 mM phosphate buffer, at pH 7.5 and 25°C Homo sapiens 3,3'-methanediylbis(4-hydroxy-5-methoxy-2H-chromen-2-one)
1.6.5.2 0.000039
-
 without bovine serum albumin, in 50 mM phosphate buffer, at pH 7.5 and 25°C Homo sapiens 3-benzyl-4-hydroxy-6,7-dimethyl-2H-chromen-2-one
1.6.5.2 0.000062
-
 without bovine serum albumin, in 50 mM phosphate buffer, at pH 7.5 and 25°C Homo sapiens 3,3'-methanediylbis(4-hydroxy-6,7-dimethoxy-2H-chromen-2-one)
1.6.5.2 0.000096
-
 with 0.002 mM bovine serum albumin, in 50 mM phosphate buffer, at pH 7.5 and 25°C Homo sapiens 3,3'-methanediylbis(4-hydroxy-7,8-dimethyl-2H-chromen-2-one)
1.6.5.2 0.000144
-
 without bovine serum albumin, in 50 mM phosphate buffer, at pH 7.5 and 25°C Homo sapiens 3-benzyl-4-hydroxy-2H-chromen-2-one
1.6.5.2 0.000167
-
 with 0.002 mM bovine serum albumin, in 50 mM phosphate buffer, at pH 7.5 and 25°C Homo sapiens 4-hydroxy-6,7-dimethyl-3-(2-naphthylmethyl)-2H-chromen-2-one
1.6.5.2 0.000192
-
 with 0.002 mM bovine serum albumin, in 50 mM phosphate buffer, at pH 7.5 and 25°C Homo sapiens 3-(3,4-dimethylbenzyl)-4-hydroxy-6,7-dimethyl-2H-chromen-2-one
1.6.5.2 0.000233
-
 with 0.002 mM bovine serum albumin, in 50 mM phosphate buffer, at pH 7.5 and 25°C Homo sapiens 3,3'-methanediylbis(4-hydroxy-6,7-dimethyl-2H-chromen-2-one)
1.6.5.2 0.000255
-
 with 0.002 mM bovine serum albumin, in 50 mM phosphate buffer, at pH 7.5 and 25°C Homo sapiens 4-hydroxy-3-(2-naphthylmethyl)-2H-benzo[h]chromen-2-one
1.6.5.2 0.00037
-
 with 0.002 mM bovine serum albumin, in 50 mM phosphate buffer, at pH 7.5 and 25°C Homo sapiens 3,3'-methanediylbis(4-hydroxy-2H-benzo[h]chromen-2-one)
1.6.5.2 0.000404
-
 with 0.002 mM bovine serum albumin, in 50 mM phosphate buffer, at pH 7.5 and 25°C Homo sapiens dicoumarol
1.6.5.2 0.00045
-
 with 0.002 mM bovine serum albumin, in 50 mM phosphate buffer, at pH 7.5 and 25°C Homo sapiens 4-hydroxy-3-(1-naphthylmethyl)-2H-benzo[h]chromen-2-one
1.6.5.2 0.000465
-
 with 0.002 mM bovine serum albumin, in 50 mM phosphate buffer, at pH 7.5 and 25°C Homo sapiens 2-benzyl-1-hydroxy-3H-benzo[f]chromen-3-one
1.6.5.2 0.00058
-
 without bovine serum albumin, in 50 mM phosphate buffer, at pH 7.5 and 25°C Homo sapiens 3,3'-butane-1,1-diylbis(4-hydroxy-2H-chromen-2-one)
1.6.5.2 0.00061
-
 with 0.002 mM bovine serum albumin, in 50 mM phosphate buffer, at pH 7.5 and 25°C Homo sapiens 1-hydroxy-2-(1-naphthylmethyl)-3H-benzo[f]chromen-3-one
1.6.5.2 0.00066
-
 with 0.002 mM bovine serum albumin, in 50 mM phosphate buffer, at pH 7.5 and 25°C Homo sapiens 3-benzyl-4-hydroxy-6,7-dimethyl-2H-chromen-2-one
1.6.5.2 0.00079
-
 with 0.002 mM bovine serum albumin, in 50 mM phosphate buffer, at pH 7.5 and 25°C Homo sapiens 3,3'-methanediylbis(4-hydroxy-7-methoxy-2H-chromen-2-one)
1.6.5.2 0.00088
-
 with 0.002 mM bovine serum albumin, in 50 mM phosphate buffer, at pH 7.5 and 25°C Homo sapiens 3-benzyl-4-hydroxy-2H-benzo[h]chromen-2-one
1.6.5.2 0.001095
-
 with 0.002 mM bovine serum albumin, in 50 mM phosphate buffer, at pH 7.5 and 25°C Homo sapiens 4-hydroxy-6,7-dimethyl-3-(1-naphthylmethyl)-2H-chromen-2-one
1.6.5.2 0.00115
-
 with 0.002 mM bovine serum albumin, in 50 mM phosphate buffer, at pH 7.5 and 25°C Homo sapiens 3,3'-methanediylbis(4-hydroxy-7-fluoro-2H-chromen-2-one)
1.6.5.2 0.001221
-
 without bovine serum albumin, in 50 mM phosphate buffer, at pH 7.5 and 25°C Homo sapiens ethyl bis(4-hydroxy-2-oxo-2H-chromen-3-yl)acetate
1.6.5.2 0.001452
-
 with 0.002 mM bovine serum albumin, in 50 mM phosphate buffer, at pH 7.5 and 25°C Homo sapiens 4-hydroxy-3-(2-naphthylmethyl)-2H-chromen-2-one
1.6.5.2 0.001497
-
 with 0.002 mM bovine serum albumin, in 50 mM phosphate buffer, at pH 7.5 and 25°C Homo sapiens 3,3'-methanediylbis(4-hydroxy-6,7-dimethoxy-2H-chromen-2-one)
1.6.5.2 0.001522
-
 with 0.002 mM bovine serum albumin, in 50 mM phosphate buffer, at pH 7.5 and 25°C Homo sapiens 4-hydroxy-3-(1-naphthylmethyl)-2H-chromen-2-one
1.6.5.2 0.0016
-
 with 0.002 mM bovine serum albumin, in 50 mM phosphate buffer, at pH 7.5 and 25°C Homo sapiens 3,3'-methanediylbis(4-hydroxy-6-fluoro-2H-chromen-2-one)
1.6.5.2 0.0016
-
 with 0.002 mM bovine serum albumin, in 50 mM phosphate buffer, at pH 7.5 and 25°C Homo sapiens 3-(3,4-dimethylbenzyl)-4-hydroxy-2H-chromen-2-one
1.6.5.2 0.002366
-
 with 0.002 mM bovine serum albumin, in 50 mM phosphate buffer, at pH 7.5 and 25°C Homo sapiens 1-hydroxy-2-(2-naphthylmethyl)-3H-benzo[f]chromen-3-one
1.6.5.2 0.0032
-
 with 0.002 mM bovine serum albumin, in 50 mM phosphate buffer, at pH 7.5 and 25°C Homo sapiens 3-benzyl-4-hydroxy-2H-chromen-2-one
1.6.5.2 0.0033
-
 with 0.002 mM bovine serum albumin, in 50 mM phosphate buffer, at pH 7.5 and 25°C Homo sapiens 3,3'-methanediylbis(4-hydroxy-6-methoxy-2H-chromen-2-one)
1.6.5.2 0.005322
-
 with 0.002 mM bovine serum albumin, in 50 mM phosphate buffer, at pH 7.5 and 25°C Homo sapiens 3,3'-butane-1,1-diylbis(4-hydroxy-2H-chromen-2-one)
1.6.5.2 0.0055
-
 with 0.002 mM bovine serum albumin, in 50 mM phosphate buffer, at pH 7.5 and 25°C Homo sapiens 3,3'-methylenebis(4-hydroxy-6-methyl-2H-chromen-2-one)
1.6.5.2 0.00625
-
 with 0.002 mM bovine serum albumin, in 50 mM phosphate buffer, at pH 7.5 and 25°C Homo sapiens 3,3'-methanediylbis(4-hydroxy-6-chloro-2H-chromen-2-one)
1.6.5.2 0.02233
-
 with 0.002 mM bovine serum albumin, in 50 mM phosphate buffer, at pH 7.5 and 25°C Homo sapiens ethyl bis(4-hydroxy-2-oxo-2H-chromen-3-yl)acetate
1.6.5.2 0.063
-
 with 0.002 mM bovine serum albumin, in 50 mM phosphate buffer, at pH 7.5 and 25°C Homo sapiens 3,3'-methanediylbis(4-hydroxy-6,8-dibromo-2H-chromen-2-one)