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Drug-Target Interaction

Drug

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PubChem ID:5281654
Structure:
Synonyms:
17794_FLUKA
17794_SIGMA
3'-Methoxy-3,4',5,7-tetrahydroxyflavone
3'-Methoxyquercetin
3'-O-Methylquercetin
3,4',5,7-tetrahydroxy-3'-methoxy-flavone
3,4',5,7-tetrahydroxy-3'-methoxyflavone
3,5,7,4'-Tetrahydroxy-3'-methoxyflavone
3,5,7-Trihydroxy-2-(3-hydroxy-4-methoxyphenyl)-4-benzopyrone
3,5,7-Trihydroxy-2-(4-hydroxy-3-methoxyphenyl)-4-benzopyrone
3,5,7-trihydroxy-2-(4-hydroxy-3-methoxyphenyl)chromen-4-one
3-methyl-quercetin
3-Methylquercetin
3-Methylquercetine
4'-Methoxy-3,3',5,7-tetrahydroxy-flavone
4'-Methoxyquercetin
4'-Methylquercetin
4'-O-Methylquercetin
480-19-3
4H-1-Benzopyran-4-one, 2-(3-methoxy-4-hydroxyphenyl)-3,5,7-trihydroxy-
4H-1-Benzopyran-4-one, 3,5,7-trihydroxy-2-(3-hydroxy-4-methoxyphenyl)-
4H-1-Benzopyran-4-one, 3,5,7-trihydroxy-2-(3-hydroxy-4-methoxyphenyl)- (9CI)
4H-1-Benzopyran-4-one, 3,5,7-trihydroxy-2-(4-hydroxy-3-methoxyphenyl)-
4H-1-Benzopyran-4-one, 3,5,7-trihydroxy-2-(4-hydroxy-3-methoxyphenyl)- (9CI)
5-18-05-00496 (Beilstein Handbook Reference)
603-61-2
AC-20263
AC1NQYTP
ACon1_000275
AIDS-003060
AIDS003060
BRD-K83977206-001-01-4
BRN 0044723
BRN 0324993
C.I. 75680
C047368
C10084
C16H12O7
CCRIS 3791
CHEMBL379064
CPD-8004
EINECS 207-545-5
EINECS 210-050-7
Flavone, 3'-methoxy-3,4',5,7-tetrahydroxy-
Flavone, 3,3',5,7-tetrahydroxy-4'-methoxy-
FLAVONE, 3,4',5,7-TETRAHYDROXY-3'-METHOXY-
FLAVONE, 4'-METHOXY-3,3',5,7-TETRAHYDROXY-
Flavonoid
iso-rhamnetin
isorhamentin
Isorhamnetin
isorhamnetine
Isorhamnetol
LMPK12110002
LS-69023
LS-69043
MEGxp0_001863
MolPort-001-742-583
NCGC00163572-01
NCGC00163572-02
NCGC00163572-03
NCGC00180719-01
Oprea1_145406
Quercetin 3'-methyl ether
Quercetin, 4'-methyl ether
SBB067248
ST5309356
Tamarixetin
ZINC00517261

Target

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Uniprot ID:CP1A1_HUMAN
Synonyms:
CYPIA1
Cytochrome P450 1A1
P450 form 6
P450-C
P450-P1
EC-Numbers:1.14.14.1
Organism:Homo sapiens
Human
PDB IDs:-

Binding Affinities:

Ki: Kd:Ic 50:Ec50/Ic50:
----
--56-

References:

16226778
Effect of Ginkgo biloba extract on procarcinogen-bioactivating human CYP1 enzymes: identification of isorhamnetin, kaempferol, and quercetin as potent inhibitors of CYP1B1.. Thomas K H Chang; Jie Chen; Eugene Y H Yeung (2006) Toxicology and applied pharmacology display abstract
In the present study, we investigated the effect of Ginkgo biloba extracts and some of its individual constituents on the catalytic activity of human cytochrome P450 enzymes CYP1B1, CYP1A1, and CYP1A2. G. biloba extract of known abundance of terpene trilactones and flavonol glycosides inhibited 7-ethoxyresorufin O-dealkylation catalyzed by human recombinant CYP1B1, CYP1A1, and CYP1A2, and human liver microsomes, with apparent Ki values of 2 +/- 0.3, 5 +/- 0.5, 16 +/- 1.4, and 39 +/- 1.2 microg/ml (mean +/- SE), respectively. In each case, the mode of inhibition was of the mixed type. Bilobalide, ginkgolides A, B, C, and J, quercetin 3-O-rutinoside, kaempferol 3-O-rutinoside, and isorhamentin 3-O-rutinoside were not responsible for the inhibition of CYP1 enzymes by G. biloba extract, as determined by experiments with these individual chemicals at the levels present in the extract. In contrast, the aglycones of quercetin, kaempferol, and isorhamentin inhibited CYP1B1, CYP1A1, and CYP1A2. Among the three flavonol aglycones, isorhamentin was the most potent in inhibiting CYP1B1 (apparent Ki = 3 +/- 0.1 nM), whereas quercetin was the least potent in inhibiting CYP1A2 (apparent Ki = 418 +/- 50 nM). The mode of inhibition was competitive, noncompetitive, or mixed, depending on the enzyme and the flavonol. G. biloba extract also reduced benzo[a]pyrene hydroxylation, and the effect was greater with CYP1B1 than with CYP1A1 as the catalyst. Overall, our novel findings indicate that G. biloba extract and the flavonol aglycones isorhamnetin, kaempferol, and quercetin preferentially inhibit the in vitro catalytic activity of human CYP1B1.