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]
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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)

Hydrogen Bond Donor Count (hbonddonor)

Hydrogen Bond Acceptor Count (hbondacc)

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
UNII: 9KJL21T0QJ
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]

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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]

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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]

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Molecular Interaction Atlas (MIA)

MIA Detail

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.