Literature summary for 1.6.5.2 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.

Crystallization (Commentary)

Crystallization (Comment)	Organism
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

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

Organism

Organism	UniProt	Comment	Textmining
Homo sapiens	P15559	-	-

Source Tissue

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

Substrates and Products (Substrate)

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

Synonyms

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

Cofactor

Cofactor	Comment	Organism	Structure
NADH	-	Homo sapiens
NADPH	-	Homo sapiens

IC50 Value

IC50 Value	IC50 Value Maximum	Comment	Organism	Inhibitor
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)
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)
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)
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
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
0.0000026	-	without bovine serum albumin, in 50 mM phosphate buffer, at pH 7.5 and 25°C	Homo sapiens	dicoumarol
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)
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)
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)
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)
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)
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
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
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
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
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)
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
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)
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)
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
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
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
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
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
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)
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
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)
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)
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
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
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
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)
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
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)
0.000404	-	with 0.002 mM bovine serum albumin, in 50 mM phosphate buffer, at pH 7.5 and 25°C	Homo sapiens	dicoumarol
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
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
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)
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
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
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)
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
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
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)
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
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
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)
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
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)
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
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
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
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)
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)
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)
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)
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
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)