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Drug-Target Interaction

Drug

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PubChem ID:5280934
Structure:
Synonyms:
(9,12,15)-linolenic acid
(9Z,12Z,15Z)-9,12,15-Octadecatrienoic acid
(9Z,12Z,15Z)-octadeca-9,12,15-trienoic acid
(9Z,12Z,15Z)-Octadecatrienoic acid
(9Z,12Z,15Z)octadeca-9,12,15-trienoic acid
(all-Z)-9,12,15-Octadecatrienoic acid
(Z,Z,Z)-9,12,15-Octadecatrienoic acid
(Z,Z,Z)-Octadeca-9,12,15-trienoic acid
2DCD0473-E5CC-47BB-A0A4-95899AFF6C4B
463-40-1
62160_FLUKA
62170_FLUKA
62170_SIGMA
9,12,15-all-cis-Octadecatrienoic acid
9,12,15-Octadecatrienoic acid
9,12,15-octadecatrienoic acid, (9Z,12Z,15Z)-
9,12,15-Octadecatrienoic acid, (9Z,12Z,15Z)- (9CI)
9,12,15-Octadecatrienoic acid, (Z,Z,Z)-
9-cis,12-cis,15-cis-Octadecatrienoic acid
9Z,12Z,15Z-Octadecatrienoic acid
AC1NQXSA
AI3-23986
ALA
all-cis-9,12,15-Octadecatrienoic acid
alpha-Linolenate
alpha-Linolenic acid
alpha-Lnn
BML3-B05
BRD-K33396764-001-02-0
BSPBio_001376
C06427
C18:3n-3,6,9
CCRIS 656
CHEBI:27432
CHEMBL8739
cis,cis,cis-9,12,15-Octadecatrienoic acid
cis-9, cis-12, cis-15-octadecatrienoic acid
cis-9,cis-12,cis-15-Octadecatrienoic acid
cis-Delta(9,12,15)-octadecatrienoic acid
cis-Delta9,12,15-Octadecatrienoic acid
CMC_7371
DB00132
HMS1361E18
HMS1791E18
HMS1989E18
HMS2233C13
IDI1_033846
L000707
L0050
L2376_SIGMA
Linolenate
Linolenic acid
LINOLENIC ACID (18:3 n-3)
Linolenic acid (8CI)
LMFA01030152
LNL
MLS001336029
MLS001336030
MLS002454413
NCGC00091058-01
NCGC00091058-02
NCGC00091058-04
NCGC00091058-05
NCGC00091058-06
NCGC00091058-07
NCGC00091058-08
NCGC00091058-09
NCGC00091058-10
nchembio.161-comp1
Octadecatrienoic acid, 9,12,15-(Z,Z,Z)-
SMR000857336
ST072192

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:

16978661
The inhibitory effect of polyunsaturated fatty acids on human CYP enzymes.. Hsien-Tsung Yao; Yi-Wei Chang; Shih-Jung Lan; Chiung-Tong Chen; John T A Hsu; Teng-Kuang Yeh (2006) Life sciences display abstract
The inhibitory effect of saturated fatty acids (SFAs): palmitic acid (PA), stearic acid (SA) and polyunsaturated fatty acids (PUFAs): linoleic acid (LA), linolenic acid (LN), arachidonic acid (AA), eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA) on six human drug-metabolizing enzymes (CYP1A2, 2C9, 2C19, 2D6, 2E1 and 3A4) was studied. Supersomes from baculovirus-expressing single isoforms were used as the enzyme source. Phenacetin O-deethylation (CYP1A2), diclofenac 4-hydroxylation (CYP2C9), mephenytoin 4-hydroxylation (CYP2C19), dextromethorphan O-demethylation (CYP2D6), chlorzoxazone 6-hydroxylation (CYP2E1) and midazolam 1-hydroxylation (CYP3A4) were used as the probes. Results show that all the five examined PUFAs competitively inhibited CYP2C9- and CYP2C19-catalyzed metabolic reactions, with Ki values ranging from 1.7 to 4.7 microM and 2.3 to 7.4 microM, respectively. Among these, AA, EPA and DHA tended to have greater inhibitory potencies (lower IC(50) and Ki values) than LA and LN. In addition, these five PUFAs also competitively inhibited the metabolic reactions catalyzed by CYP1A2, 2E1 and 3A4 to a lesser extent (Ki values>10 microM). On the other hand, palmitic and stearic acids, the saturated fatty acids, had no inhibitory effect on the activities of six human CYP isozymes at concentrations up to 200 microM. Incubation of PUFAs with CYP2C9 or CYP2C19 in the presence of NADPH resulted in the decrease of PUFA concentrations in the incubation mixtures. These results indicate that the PUFAs are potent inhibitors as well as the substrates of CYP2C9 and CYP2C19.