General Information of Drug (ID: DMDGPY9)

Drug Name
LINOLEIC ACID
Synonyms
linoleic acid; 60-33-3; Linolic acid; Telfairic acid; (9Z,12Z)-octadeca-9,12-dienoic acid; cis,cis-Linoleic acid; Grape seed oil; Linoleate; cis,cis-9,12-Octadecadienoic acid; Emersol 315; cis-9,cis-12-Octadecadienoic acid; 9,12-Linoleic acid; Unifac 6550; 9Z,12Z-Linoleic acid; Extra Linoleic 90; 9-cis,12-cis-Linoleic acid; Polylin 515; Emersol 310; Polylin No. 515; Oils, grape; 9Z,12Z-octadecadienoic acid; alpha-Linoleic acid; all-cis-9,12-Octadecadienoic acid; Linoleic; acide linoleique; (Z,Z)-9,12-Octadecadienoic acid; acido lino
Indication
Disease Entry ICD 11 Status REF
Discovery agent N.A. Investigative [1]
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 2 Molecular Weight (mw) 280.4
Logarithm of the Partition Coefficient (xlogp) 6.8
Rotatable Bond Count (rotbonds) 14
Hydrogen Bond Donor Count (hbonddonor) 1
Hydrogen Bond Acceptor Count (hbondacc) 2
Chemical Identifiers
Formula
C18H32O2
IUPAC Name
(9Z,12Z)-octadeca-9,12-dienoic acid
Canonical SMILES
CCCCC/C=C\\C/C=C\\CCCCCCCC(=O)O
InChI
InChI=1S/C18H32O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h6-7,9-10H,2-5,8,11-17H2,1H3,(H,19,20)/b7-6-,10-9-
InChIKey
OYHQOLUKZRVURQ-HZJYTTRNSA-N
Cross-matching ID
PubChem CID
5280450
ChEBI ID
CHEBI:17351
CAS Number
60-33-3
DrugBank ID
DB14104
TTD ID
D03LOG
INTEDE ID
DR2161

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Fatty acid-binding protein 4 (FABP4) TTHWMFZ FABP4_HUMAN Inhibitor [2]

Drug-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID MOA REF
Linoleate 10-hydratase (10-LAH) DEWD860 A0A1I9RYU9_LACPN Substrate [3]
Linoleate isomerase (lai) DEQ58KF D2BQ64_LACLK Substrate [4], [5]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
Achaete-scute homolog 2 (ASCL2) OT3D62WB ASCL2_HUMAN Gene/Protein Processing [6]
Acyl-CoA 6-desaturase (FADS2) OTUX531P FADS2_HUMAN Gene/Protein Processing [7]
ATP-binding cassette sub-family G member 1 (ABCG1) OT5BG6MK ABCG1_HUMAN Gene/Protein Processing [8]
C-C motif chemokine 2 (CCL2) OTAD2HEL CCL2_HUMAN Gene/Protein Processing [9]
Catalase (CAT) OTHEBX9R CATA_HUMAN Gene/Protein Processing [10]
Cholinesterase (BCHE) OTOH3WQ9 CHLE_HUMAN Gene/Protein Processing [11]
Choriogonadotropin subunit beta 3 (CGB3) OTVM2SU3 CGB3_HUMAN Protein Interaction/Cellular Processes [6]
Cytochrome P450 1A2 (CYP1A2) OTLLBX48 CP1A2_HUMAN Gene/Protein Processing [12]
Cytochrome P450 2A6 (CYP2A6) OT52TWG3 CP2A6_HUMAN Gene/Protein Processing [13]
Cytochrome P450 2C19 (CYP2C19) OTFMJYYE CP2CJ_HUMAN Gene/Protein Processing [12]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

References

1 URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 1052).
2 Discovery of highly selective inhibitors of human fatty acid binding protein 4 (FABP4) by virtual screening. Bioorg Med Chem Lett. 2010 Jun 15;20(12):3675-9.
3 Characterization of linoleate 10-hydratase of Lactobacillus plantarum and novel antifungal metabolites. Front Microbiol. 2016 Oct 4;7:1561. eCollection 2016.
4 Cell-associated alpha-amylases of butyrate-producing Firmicute bacteria from the human colon. Microbiology. 2006 Nov;152(Pt 11):3281-3290.
5 Effect of linoleic acid concentration on conjugated linoleic acid production by Butyrivibrio fibrisolvens A38. Appl Environ Microbiol. 2000 Dec;66(12):5226-30.
6 Expression of cFABP and PPAR in trophoblast cells: effect of PPAR ligands on linoleic acid uptake and differentiation. Biochim Biophys Acta. 2005 Feb 21;1687(1-3):181-94. doi: 10.1016/j.bbalip.2004.11.017.
7 Regulation of stearoyl-coenzyme A desaturase and fatty acid delta-6 desaturase-2 expression by linoleic acid and arachidonic acid in human sebocytes leads to enhancement of proinflammatory activity but does not affect lipogenesis. Br J Dermatol. 2011 Aug;165(2):269-76.
8 Unsaturated fatty acids suppress the expression of the ATP-binding cassette transporter G1 (ABCG1) and ABCA1 genes via an LXR/RXR responsive element. Atherosclerosis. 2007 Mar;191(1):11-21. doi: 10.1016/j.atherosclerosis.2006.04.018. Epub 2006 May 30.
9 Omega-3 fatty acids inhibit an increase of proinflammatory cytokines in patients with active Crohn's disease compared with omega-6 fatty acids. Aliment Pharmacol Ther. 2005 Dec;22(11-12):1121-8. doi: 10.1111/j.1365-2036.2005.02698.x.
10 Lipid peroxides induce expression of catalase in cultured vascular cells. J Lipid Res. 2000 Aug;41(8):1205-13.
11 Butyrylcholinesterase expression is regulated by fatty acids in HepG2 cells. Chem Biol Interact. 2016 Nov 25;259(Pt B):276-281.
12 The inhibitory effect of polyunsaturated fatty acids on human CYP enzymes. Life Sci. 2006 Nov 25;79(26):2432-40.
13 High fat diet-induced hepatic 18-carbon fatty acids accumulation up-regulates CYP2A5/CYP2A6 via NF-E2-related factor 2. Front Pharmacol. 2017 May 15;8:233.