Details of the Drug

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
CHEMBL267476
CAS Number
60-33-3
UNII
9KJL21T0QJ
DrugBank ID
DB14104
TTD ID
D03LOG
INTEDE ID
DR2161
Drug-Molecule Activity Atlas (DMA)NEW Click to Jump to the Detailed DMA Information of This Drug
Drug Pharmacogenomic Perturbation (DPP)NEW Click to Jump to the Detailed DPP Information of This Drug
Drug ADMET Endpoint Profile (DAE)NEW Click to Jump to the Detailed DAE Information of This Drug

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]
C-C motif chemokine 2 (CCL2) OTAD2HEL CCL2_HUMAN Gene/Protein Processing [7]
Choriogonadotropin subunit beta 3 (CGB3) OTVM2SU3 CGB3_HUMAN Protein Interaction/Cellular Processes [6]
Cytochrome P450 2C19 (CYP2C19) OTFMJYYE CP2CJ_HUMAN Gene/Protein Processing [8]
Fatty acid-binding protein, heart (FABP3) OT562DA1 FABPH_HUMAN Gene/Protein Processing [6]
Hepatitis A virus cellular receptor 1 (HAVCR1) OT184CRZ HAVR1_HUMAN Protein Interaction/Cellular Processes [9]
Organic anion transporter 3 (SLC22A8) OT8BY933 S22A8_HUMAN Gene/Protein Processing [10]
Peroxisome proliferator-activated receptor gamma coactivator 1-alpha (PPARGC1A) OTHCDQ22 PRGC1_HUMAN Gene/Protein Processing [11]
Phospholipid-transporting ATPase ABCA1 (ABCA1) OT94G6BQ ABCA1_HUMAN Protein Interaction/Cellular Processes [12]
Solute carrier family 22 member 6 (SLC22A6) OTKRCBVM S22A6_HUMAN Gene/Protein Processing [10]
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 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.
8 The inhibitory effect of polyunsaturated fatty acids on human CYP enzymes. Life Sci. 2006 Nov 25;79(26):2432-40.
9 In vitro toxicological assessment of free 3-MCPD and select 3-MCPD esters on human proximal tubule HK-2 cells. Cell Biol Toxicol. 2020 Jun;36(3):209-221. doi: 10.1007/s10565-019-09498-0. Epub 2019 Nov 5.
10 From the Cover: Identification of Natural Products as Inhibitors of Human Organic Anion Transporters (OAT1 and OAT3) and Their Protective Effect on Mercury-Induced Toxicity. Toxicol Sci. 2018 Feb 1;161(2):321-334. doi: 10.1093/toxsci/kfx216.
11 A cardiac-specific robotized cellular assay identified families of human ligands as inducers of PGC-1 expression and mitochondrial biogenesis. PLoS One. 2012;7(10):e46753. doi: 10.1371/journal.pone.0046753. Epub 2012 Oct 3.
12 Unsaturated fatty acids phosphorylate and destabilize ABCA1 through a phospholipase D2 pathway. J Biol Chem. 2005 Oct 28;280(43):35896-903. doi: 10.1074/jbc.M506210200. Epub 2005 Aug 23.