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Literature summary extracted from

  • Nolan, K.A.; Zhao, H.; Faulder, P.F.; Frenkel, A.D.; Timson, D.J.; Siegel, D.; Ross, D.; Burke, T.R.; Stratford, I.J.; Bryce, R.A.
    Coumarin-based inhibitors of human NAD(P)H:quinone oxidoreductase-1. Identification, structure-activity, off-target effects and in vitro human pancreatic cancer toxicity (2007), J. Med. Chem., 50, 6316-6325.
    View publication on PubMed

Application

EC Number Application Comment Organism
1.6.5.2 drug development new coumarin-based competitive inhibitors of NQO1. NQO1 inhibition as an anticancer drug design target and superoxide generation as the dicoumarol-mediated mechanism of cytotoxicity Homo sapiens

Cloned(Commentary)

EC Number Cloned (Comment) Organism
1.6.5.2
-
 Homo sapiens

Inhibitors

EC Number Inhibitors Comment Organism Structure
1.6.5.2 3,3'-(9H-fluoren-3-ylmethanediyl)bis(4-hydroxy-2H-chromen-2-one)
-
 Homo sapiens
1.6.5.2 3,3'-(biphenyl-4-ylmethanediyl)bis(4-hydroxy-2H-chromen-2-one)
-
 Homo sapiens
1.6.5.2 3,3'-(furan-2-ylmethanediyl)bis(4-hydroxy-2H-chromen-2-one)
-
 Homo sapiens
1.6.5.2 3,3'-(naphthalen-2-ylmethanediyl)bis(4-hydroxy-2H-chromen-2-one)
-
 Homo sapiens
1.6.5.2 3,3'-(phenylmethanediyl)bis(4,7-dihydroxy-2H-chromen-2-one)
-
 Homo sapiens
1.6.5.2 3,3'-(phenylmethanediyl)bis(4-hydroxy-2H-chromen-2-one)
-
 Homo sapiens
1.6.5.2 3,3'-(pyridin-2-ylmethanediyl)bis(4,7-dihydroxy-2H-chromen-2-one)
-
 Homo sapiens
1.6.5.2 3,3'-(quinolin-3-ylmethanediyl)bis(4-hydroxy-2H-chromen-2-one)
-
 Homo sapiens
1.6.5.2 3,3'-(thiophen-2-ylmethanediyl)bis(4-hydroxy-2H-chromen-2-one)
-
 Homo sapiens
1.6.5.2 3,3'-([4-[(E)-2-phenylethenyl]phenyl]methanediyl)bis(4-hydroxy-2H-chromen-2-one)
-
 Homo sapiens
1.6.5.2 3,3'-methanediylbis(4,7-dihydroxy-2H-chromen-2-one)
-
 Homo sapiens
1.6.5.2 3,3'-[(4-chlorophenyl)methanediyl]bis(4-hydroxy-2H-chromen-2-one)
-
 Homo sapiens
1.6.5.2 3,3'-[(4-hydroxy-3-methoxyphenyl)methanediyl]bis(4-hydroxy-2H-chromen-2-one)
-
 Homo sapiens
1.6.5.2 3,3'-[(4-hydroxyphenyl)methanediyl]bis(4-hydroxy-2H-chromen-2-one)
-
 Homo sapiens
1.6.5.2 3,3'-[(4-methoxyphenyl)methanediyl]bis(4-hydroxy-2H-chromen-2-one)
-
 Homo sapiens
1.6.5.2 3,3'-[[3,5-bis(benzyloxy)phenyl]methanediyl]bis(4-hydroxy-2H-chromen-2-one)
-
 Homo sapiens
1.6.5.2 3,3'-[[4-(1-methylethyl)phenyl]methanediyl]bis(4-hydroxy-2H-chromen-2-one)
-
 Homo sapiens
1.6.5.2 3,3'-[[4-(dimethylamino)phenyl]methanediyl]bis(4-hydroxy-2H-chromen-2-one)
-
 Homo sapiens
1.6.5.2 3-[[3-[bis(4-hydroxy-2-oxo-2H-chromen-3-yl)methyl]phenyl](4-hydroxy-2-oxo-4a,8a-dihydro-2H-chromen-3-yl)methyl]-4-hydroxy-2H-chromen-2-one
-
 Homo sapiens
1.6.5.2 3-[[4-[bis(4-hydroxy-2-oxo-2H-chromen-3-yl)methyl]phenyl](4,7-dihydroxy-2-oxo-4a,8a-dihydro-2H-chromen-3-yl)methyl]-4,7-dihydroxy-2H-chromen-2-one
-
 Homo sapiens
1.6.5.2 3-[[4-[bis(4-hydroxy-2-oxo-2H-chromen-3-yl)methyl]phenyl](4-hydroxy-2-oxo-4a,8a-dihydro-2H-chromen-3-yl)methyl]-4-hydroxy-2H-chromen-2-one
-
 Homo sapiens
1.6.5.2 4-amino-2H-chromen-2-one
-
 Homo sapiens
1.6.5.2 4-[bis(4-hydroxy-2-oxo-2H-chromen-3-yl)methyl]benzoic acid
-
 Homo sapiens
1.6.5.2 7-(4-hydroxy-2-oxo-2H-chromen-3-yl)-6a,7-dihydro-4aH,6H,8H-pyrano[3,2-c:5,6-c']dichromene-6,8-dione
-
 Homo sapiens
1.6.5.2 7-(4-hydroxy-2-oxo-2H-chromen-3-yl)-6H,7H-chromeno[4,3-b]chromen-6-one
-
 Homo sapiens
1.6.5.2 dicoumarol
-
 Homo sapiens

Organism

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

Purification (Commentary)

EC Number Purification (Comment) Organism
1.6.5.2
-
 Homo sapiens

Source Tissue

EC Number Source Tissue Comment Organism Textmining
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 menadione + NADH
-
 Homo sapiens reduced menadione + NAD+
-
 ?

Synonyms

EC Number Synonyms Comment Organism
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 FAD
-
 Homo sapiens

IC50 Value

EC Number IC50 Value IC50 Value Maximum Comment Organism Inhibitor Structure
1.6.5.2 0.000005
-
-
 Homo sapiens 3,3'-methanediylbis(4,7-dihydroxy-2H-chromen-2-one)
1.6.5.2 0.000005
-
 without bovine serum albumin Homo sapiens dicoumarol
1.6.5.2 0.000014
-
-
 Homo sapiens 3,3'-(naphthalen-2-ylmethanediyl)bis(4-hydroxy-2H-chromen-2-one)
1.6.5.2 0.0001
-
-
 Homo sapiens 3,3'-[[4-(dimethylamino)phenyl]methanediyl]bis(4-hydroxy-2H-chromen-2-one)
1.6.5.2 0.00011
-
-
 Homo sapiens 3-[[4-[bis(4-hydroxy-2-oxo-2H-chromen-3-yl)methyl]phenyl](4-hydroxy-2-oxo-4a,8a-dihydro-2H-chromen-3-yl)methyl]-4-hydroxy-2H-chromen-2-one
1.6.5.2 0.00015
-
-
 Homo sapiens 3,3'-(9H-fluoren-3-ylmethanediyl)bis(4-hydroxy-2H-chromen-2-one)
1.6.5.2 0.0002
-
-
 Homo sapiens 7-(4-hydroxy-2-oxo-2H-chromen-3-yl)-6H,7H-chromeno[4,3-b]chromen-6-one
1.6.5.2 0.00022
-
-
 Homo sapiens 3,3'-[(4-methoxyphenyl)methanediyl]bis(4-hydroxy-2H-chromen-2-one)
1.6.5.2 0.00025
-
-
 Homo sapiens 3-[[4-[bis(4-hydroxy-2-oxo-2H-chromen-3-yl)methyl]phenyl](4,7-dihydroxy-2-oxo-4a,8a-dihydro-2H-chromen-3-yl)methyl]-4,7-dihydroxy-2H-chromen-2-one
1.6.5.2 0.00025
-
-
 Homo sapiens 7-(4-hydroxy-2-oxo-2H-chromen-3-yl)-6a,7-dihydro-4aH,6H,8H-pyrano[3,2-c:5,6-c']dichromene-6,8-dione
1.6.5.2 0.00035
-
-
 Homo sapiens 3,3'-[[4-(1-methylethyl)phenyl]methanediyl]bis(4-hydroxy-2H-chromen-2-one)
1.6.5.2 0.00035
-
-
 Homo sapiens 3,3'-([4-[(E)-2-phenylethenyl]phenyl]methanediyl)bis(4-hydroxy-2H-chromen-2-one)
1.6.5.2 0.00035
-
 in the presence of bovine serum albumin Homo sapiens 3,3'-methanediylbis(4,7-dihydroxy-2H-chromen-2-one)
1.6.5.2 0.00038
-
-
 Homo sapiens 3,3'-(quinolin-3-ylmethanediyl)bis(4-hydroxy-2H-chromen-2-one)
1.6.5.2 0.00045
-
 in the presence of bovine serum albumin Homo sapiens dicoumarol
1.6.5.2 0.0005
-
-
 Homo sapiens 3-[[3-[bis(4-hydroxy-2-oxo-2H-chromen-3-yl)methyl]phenyl](4-hydroxy-2-oxo-4a,8a-dihydro-2H-chromen-3-yl)methyl]-4-hydroxy-2H-chromen-2-one
1.6.5.2 0.00055
-
-
 Homo sapiens 3,3'-(thiophen-2-ylmethanediyl)bis(4-hydroxy-2H-chromen-2-one)
1.6.5.2 0.0006
-
 in the presence of bovine serum albumin Homo sapiens 7-(4-hydroxy-2-oxo-2H-chromen-3-yl)-6a,7-dihydro-4aH,6H,8H-pyrano[3,2-c:5,6-c']dichromene-6,8-dione
1.6.5.2 0.00065
-
-
 Homo sapiens 3,3'-[(4-hydroxy-3-methoxyphenyl)methanediyl]bis(4-hydroxy-2H-chromen-2-one)
1.6.5.2 0.00065
-
 in the presence of bovine serum albumin Homo sapiens 7-(4-hydroxy-2-oxo-2H-chromen-3-yl)-6H,7H-chromeno[4,3-b]chromen-6-one
1.6.5.2 0.00088
-
-
 Homo sapiens 3,3'-(biphenyl-4-ylmethanediyl)bis(4-hydroxy-2H-chromen-2-one)
1.6.5.2 0.00125
-
-
 Homo sapiens 3,3'-[[3,5-bis(benzyloxy)phenyl]methanediyl]bis(4-hydroxy-2H-chromen-2-one)
1.6.5.2 0.0013
-
-
 Homo sapiens 3,3'-(furan-2-ylmethanediyl)bis(4-hydroxy-2H-chromen-2-one)
1.6.5.2 0.0017
-
-
 Homo sapiens 4-[bis(4-hydroxy-2-oxo-2H-chromen-3-yl)methyl]benzoic acid
1.6.5.2 0.0022
-
-
 Homo sapiens 3,3'-[(4-chlorophenyl)methanediyl]bis(4-hydroxy-2H-chromen-2-one)
1.6.5.2 0.0023
-
-
 Homo sapiens 3,3'-[(4-hydroxyphenyl)methanediyl]bis(4-hydroxy-2H-chromen-2-one)
1.6.5.2 0.0029
-
 in the presence of bovine serum albumin Homo sapiens 3,3'-[[4-(1-methylethyl)phenyl]methanediyl]bis(4-hydroxy-2H-chromen-2-one)
1.6.5.2 0.00325
-
-
 Homo sapiens 4-amino-2H-chromen-2-one
1.6.5.2 0.0042
-
-
 Homo sapiens 3,3'-(phenylmethanediyl)bis(4-hydroxy-2H-chromen-2-one)
1.6.5.2 0.005
-
 in the presence of bovine serum albumin Homo sapiens 3,3'-[[4-(dimethylamino)phenyl]methanediyl]bis(4-hydroxy-2H-chromen-2-one)
1.6.5.2 0.0059
-
 in the presence of bovine serum albumin Homo sapiens 3,3'-(furan-2-ylmethanediyl)bis(4-hydroxy-2H-chromen-2-one)
1.6.5.2 0.0075
-
-
 Homo sapiens 3,3'-(phenylmethanediyl)bis(4,7-dihydroxy-2H-chromen-2-one)
1.6.5.2 0.008
-
-
 Homo sapiens 3,3'-(pyridin-2-ylmethanediyl)bis(4,7-dihydroxy-2H-chromen-2-one)
1.6.5.2 0.0085
-
 in the presence of bovine serum albumin Homo sapiens 3,3'-(naphthalen-2-ylmethanediyl)bis(4-hydroxy-2H-chromen-2-one)
1.6.5.2 0.0087
-
 in the presence of bovine serum albumin Homo sapiens 3,3'-[(4-methoxyphenyl)methanediyl]bis(4-hydroxy-2H-chromen-2-one)
1.6.5.2 0.01
-
 in the presence of bovine serum albumin Homo sapiens 3,3'-(thiophen-2-ylmethanediyl)bis(4-hydroxy-2H-chromen-2-one)
1.6.5.2 0.01
-
 in the presence of bovine serum albumin Homo sapiens 3,3'-[(4-hydroxy-3-methoxyphenyl)methanediyl]bis(4-hydroxy-2H-chromen-2-one)
1.6.5.2 0.013
-
 in the presence of bovine serum albumin Homo sapiens 4-amino-2H-chromen-2-one
1.6.5.2 0.018
-
 in the presence of bovine serum albumin Homo sapiens 3,3'-(quinolin-3-ylmethanediyl)bis(4-hydroxy-2H-chromen-2-one)
1.6.5.2 0.02
-
 in the presence of bovine serum albumin Homo sapiens 3-[[4-[bis(4-hydroxy-2-oxo-2H-chromen-3-yl)methyl]phenyl](4-hydroxy-2-oxo-4a,8a-dihydro-2H-chromen-3-yl)methyl]-4-hydroxy-2H-chromen-2-one
1.6.5.2 0.021
-
 in the presence of bovine serum albumin Homo sapiens 3,3'-(phenylmethanediyl)bis(4-hydroxy-2H-chromen-2-one)
1.6.5.2 0.021
-
 in the presence of bovine serum albumin Homo sapiens 4-[bis(4-hydroxy-2-oxo-2H-chromen-3-yl)methyl]benzoic acid
1.6.5.2 0.0225
-
 in the presence of bovine serum albumin Homo sapiens 3-[[3-[bis(4-hydroxy-2-oxo-2H-chromen-3-yl)methyl]phenyl](4-hydroxy-2-oxo-4a,8a-dihydro-2H-chromen-3-yl)methyl]-4-hydroxy-2H-chromen-2-one
1.6.5.2 0.024
-
 in the presence of bovine serum albumin Homo sapiens 3,3'-(pyridin-2-ylmethanediyl)bis(4,7-dihydroxy-2H-chromen-2-one)
1.6.5.2 0.028
-
 in the presence of bovine serum albumin Homo sapiens 3,3'-[(4-chlorophenyl)methanediyl]bis(4-hydroxy-2H-chromen-2-one)
1.6.5.2 0.035
-
 in the presence of bovine serum albumin Homo sapiens 3,3'-[(4-hydroxyphenyl)methanediyl]bis(4-hydroxy-2H-chromen-2-one)
1.6.5.2 0.041
-
 in the presence of bovine serum albumin Homo sapiens 3,3'-(9H-fluoren-3-ylmethanediyl)bis(4-hydroxy-2H-chromen-2-one)
1.6.5.2 0.0445
-
 in the presence of bovine serum albumin Homo sapiens 3,3'-(biphenyl-4-ylmethanediyl)bis(4-hydroxy-2H-chromen-2-one)
1.6.5.2 0.05
-
 in the presence of bovine serum albumin Homo sapiens 3,3'-[[3,5-bis(benzyloxy)phenyl]methanediyl]bis(4-hydroxy-2H-chromen-2-one)
1.6.5.2 0.055
-
 in the presence of bovine serum albumin Homo sapiens 3-[[4-[bis(4-hydroxy-2-oxo-2H-chromen-3-yl)methyl]phenyl](4,7-dihydroxy-2-oxo-4a,8a-dihydro-2H-chromen-3-yl)methyl]-4,7-dihydroxy-2H-chromen-2-one
1.6.5.2 0.06
-
 in the presence of bovine serum albumin Homo sapiens 3,3'-([4-[(E)-2-phenylethenyl]phenyl]methanediyl)bis(4-hydroxy-2H-chromen-2-one)
1.6.5.2 0.082
-
 in the presence of bovine serum albumin Homo sapiens 3,3'-(phenylmethanediyl)bis(4,7-dihydroxy-2H-chromen-2-one)