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Drug-Target Interaction

Drug

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PubChem ID:445154
Structure:
Synonyms:
"trans-3,4′,5-trihydroxystilbene"
(E)-5-(2-(4-hydroxyphenyl)ethenyl)-1,3-benzenediol
(E)-5-(p-Hydroxystyryl)resorcinol
(E)-5-[2-(4-hydroxyphenyl)ethenyl]-1,3-benzendiol
(E)-5-[2-(4-Hydroxyphenyl)ethenyl]-1,3-benzenediol
(E)-resveratrol
1,3-Benzenediol, 5-(2-(4-hydroxyphenyl)ethenyl)-, (E)-
1,3-Benzenediol, 5-(2-(4-hydroxyphenyl)ethenyl)-, (E)-;
3,4',5-Stilbenetriol
3,4',5-trihydroxy-stilbene
3,4',5-Trihydroxy-trans-stilbene
3,4',5-Trihydroxystilbene
3,5,4'-Trihydroxy-trans-stilbene
3,5,4'-Trihydroxystilbene
3,5-Dihydroxy-4'-methoxystilbene
31100-06-8
31100-06-8 (DELETED)
34092_FLUKA
34092_RIEDEL
5-((1E)-2-(4-Hydroxyphenyl)ethenyl)-1,3-benzenediol
5-[(1E)-2-(4-Hydroxyphenyl)ethenyl]-1,3-benzenediol
5-[(1E)-2-(4-hydroxyphenyl)ethenyl]benzene-1,3-diol
5-[(1E)-2-(4-hydroxyphenyl)vinyl]benzene-1,3-diol
5-[(E)-2-(4-hydroxyphenyl)ethenyl]benzene-1,3-diol
5-[(E)-2-(4-hydroxyphenyl)vinyl]benzene-1,3-diol
5-[2-(4-hydroxyphenyl)ethenyl]benzene-1,3-diol
501-36-0
533C1DA0-4104-42B5-9D32-9265F40857E4
AC-727
AC1L9HIC
AIDS-025474
AIDS025474
BB_NC-2570
BPBio1_000479
BRD-K25591257-001-01-2
BRD-K80738081-001-06-2
BRD-K80738081-001-10-4
BSPBio_000435
BSPBio_001114
BSPBio_003461
C03582
C059514
C14H12O3
CCG-38874
CCRIS 8952
CHEBI:27881
CHEBI:45713
CHEMBL165
CPD-83
CPD000058206
CU-01000001503-3
DB02709
EU-0101111
FT-0082623
HMS1362H15
HMS1569F17
HMS1792H15
HMS1921N04
HMS1990H15
HMS2052I09
HMS2096F17
HMS2232A18
HMS3263O04
HSDB 7571
I06-0437
IDI1_002152
KSC-10-164
KUC104385N
LMPK13090005
Lopac0_001111
LS-2146
LUKBXSAWLPMMSZ-OWOJBTEDSA-
MLS000069735
MLS001055357
MLS001076538
MLS002207121
MLS002222231
MolPort-002-499-801
NCGC00017352-05
NCGC00017352-06
NCGC00017352-07
NCGC00017352-08
NCGC00017352-09
NCGC00017352-10
NCGC00017352-11
NCGC00017352-12
NCGC00017352-13
NCGC00017352-14
NCGC00017352-15
NCGC00017352-16
NCGC00017352-17
NCGC00017352-18
NCGC00017352-19
NCGC00024003-00
NCGC00024003-04
NCGC00024003-05
NCGC00024003-06
NCGC00024003-07
NCGC00024003-08
NCGC00024003-09
NCGC00024003-10
NCGC00024003-11
NCGC00024003-12
NCGC00024003-13
NCGC00024003-14
nchembio.140-comp2
nchembio.281-comp10
NSC 327430
NSC327430
Prestwick2_000508
Prestwick3_000508
Prestwick_619
PREVENTION 8 (RESVERATROL)
R 5010
R0071
R5010_SIGMA
Resveratrol
Resveratrol, E-
resveratrol-3-sulfate
Resveratrol-Supplied by Selleck Chemicals
Resvida
RM-1812
RV
S1396_Selleck
SAM001246888
SDCCGMLS-0002998.P003
SGCUT00007
SMR000058206
SPECTRUM1502223
Spectrum5_000552
SRT 501
SRT-501
SRT501
ST057251
STL
TL8003323
to_000079
trans-1,2-(3,4',5-Trihydroxydiphenyl)ethylene
trans-3,4′,5-Trihydroxystilbene
trans-3,4',5-trihydroxystilbene
trans-Resveratrol
ZINC00006787

Target

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Uniprot ID:CP1A2_HUMAN
Synonyms:
CYPIA2
Cytochrome P450 1A2
P(3)450
P450 4
P450-P3
EC-Numbers:1.14.14.1
Organism:Homo sapiens
Human
PDB IDs:2HI4
Structure:
2HI4

Binding Affinities:

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

References:

11714871
Differential inhibition and inactivation of human CYP1 enzymes by trans-resveratrol: evidence for mechanism-based inactivation of CYP1A2.. T K Chang; J Chen; W B Lee (2001) The Journal of pharmacology and experimental therapeutics display abstract
trans-Resveratrol (3,5,4'-trihydroxy-trans-stilbene) has been reported to confer chemoprotection against 7,12-dimethylbenz[a]anthracene (DMBA)-induced carcinogenicity in a murine model. A potential mechanism for this effect by trans-resveratrol is inhibition of DMBA-bioactivating cytochrome P450 (CYP) enzymes such as CYP1B1, CYP1A1, and CYP1A2. In the present study, we examined in detail the in vitro inhibitory effects of trans-resveratrol on these three human CYP enzymes. trans-Resveratrol decreased 7-ethoxyresorufin O-dealkylation activity catalyzed by human recombinant CYP1B1, CYP1A1, and CYP1A2 in a concentration-dependent manner and by a mixed type of inhibition. This direct inhibition was enzyme-selective, as judged by the differences in the apparent K(i) values (0.8 +/- 0.1 microM, 1.2 +/- 0.1 microM, and 15.5 +/- 1.1 microM for CYP1B1, CYP1A1, and CYP1A2, respectively). Preincubating recombinant CYP1A2 or human liver microsomes with trans-resveratrol and NADPH prior to the initiation of substrate oxidation resulted in a time- and concentration-dependent decrease in catalytic activity. The inactivation of liver microsomal CYP1A2 by trans-resveratrol required NADPH, was not reversible by dialysis, and was not affected by the trapping agents glutathione, N-acetylcysteine, catalase, or superoxide dismutase, but was attenuated by a CYP1A2 substrate, imipramine. Analysis of a panel of individual human liver microsomes showed intersample differences in the response to the in vitro inactivation by trans-resveratrol. In contrast to CYP1A2, CYP1B1 was not subject to inactivation by this compound and the reduction in CYP1A1 activity was time- but not concentration-dependent. In summary, trans-resveratrol differentially inhibited human CYP1 enzymes and this occurred by two distinct mechanisms: direct inhibition (mainly CYP1B1 and CYP1A1) and mechanism-based inactivation (CYP1A2).