Details of the Drug

General Information of Drug (ID: DMY64HE)

Drug Name
alpha-linolenic acid
Synonyms
Linolenic acid; linolenic acid; alpha-Linolenic acid; 463-40-1; linolenate; (9Z,12Z,15Z)-octadeca-9,12,15-trienoic acid; a-Linolenic acid; cis,cis,cis-9,12,15-Octadecatrienoic acid; all-cis-9,12,15-Octadecatrienoic acid; alpha-Linolenate; 9-cis,12-cis,15-cis-Octadecatrienoic acid; (Z,Z,Z)-9,12,15-Octadecatrienoic acid; Linolenic acid (8CI); 9,12,15-Octadecatrienoic acid, (Z,Z,Z)-; (9,12,15)-linolenic acid; alpha-Lnn; 9Z,12Z,15Z-Octadecatrienoic acid; Industrene 120; CCRIS 656; UNII-0RBV727H71; (9Z,12Z,15Z)-Octadecatrienoic acid; linolenate; alpha-LA; C18:3; LINOLENIC ACID
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) 278.4
Logarithm of the Partition Coefficient (xlogp) 5.9
Rotatable Bond Count (rotbonds) 13
Hydrogen Bond Donor Count (hbonddonor) 1
Hydrogen Bond Acceptor Count (hbondacc) 2
Chemical Identifiers
Formula
C18H30O2
IUPAC Name
(9Z,12Z,15Z)-octadeca-9,12,15-trienoic acid
Canonical SMILES
CC/C=C\\C/C=C\\C/C=C\\CCCCCCCC(=O)O
InChI
InChI=1S/C18H30O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h3-4,6-7,9-10H,2,5,8,11-17H2,1H3,(H,19,20)/b4-3-,7-6-,10-9-
InChIKey
DTOSIQBPPRVQHS-PDBXOOCHSA-N
Cross-matching ID
PubChem CID
5280934
ChEBI ID
CHEBI:27432
CAS Number
463-40-1
DrugBank ID
DB00132
TTD ID
D0C5SV
INTEDE ID
DR1988

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Free fatty acid receptor 1 (GPR40) TTB8FUC FFAR1_HUMAN Agonist [2]
G-protein coupled receptor 120 (GPR120) TT08JVB FFAR4_HUMAN Agonist [3]
Prostaglandin G/H synthase 2 (COX-2) TTVKILB PGH2_HUMAN Inhibitor [4]

Drug-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID MOA REF
Prostaglandin G/H synthase 2 (COX-2) DE492CE PGH2_HUMAN Substrate [5]
Prostaglandin G/H synthase 1 (COX-1) DE073H6 PGH1_HUMAN Substrate [5]
Carboxylic ester hydrolase (CEH) DE30GZN A0A317G4I6_BUTFI Substrate [6], [7]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
Bile acid receptor (NR1H4) OTWZLPTB NR1H4_HUMAN Protein Interaction/Cellular Processes [8]
Carnitine O-palmitoyltransferase 1, liver isoform (CPT1A) OTI862QH CPT1A_HUMAN Gene/Protein Processing [8]
Cholinesterase (BCHE) OTOH3WQ9 CHLE_HUMAN Gene/Protein Processing [9]
Cytochrome P450 1A2 (CYP1A2) OTLLBX48 CP1A2_HUMAN Gene/Protein Processing [10]
Cytochrome P450 2A6 (CYP2A6) OT52TWG3 CP2A6_HUMAN Gene/Protein Processing [11]
Cytochrome P450 2C19 (CYP2C19) OTFMJYYE CP2CJ_HUMAN Gene/Protein Processing [10]
Cytochrome P450 2C9 (CYP2C9) OTGLBN29 CP2C9_HUMAN Gene/Protein Processing [10]
Cytochrome P450 2E1 (CYP2E1) OTHQ17JG CP2E1_HUMAN Gene/Protein Processing [10]
Cytochrome P450 3A4 (CYP3A4) OTQGYY83 CP3A4_HUMAN Gene/Protein Processing [10]
Glutamate--cysteine ligase catalytic subunit (GCLC) OTESDI4D GSH1_HUMAN Gene/Protein Processing [12]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

Molecular Expression Atlas of This Drug

The Studied Disease Discovery agent
ICD Disease Classification N.A.
Molecule Name Molecule Type Gene Name p-value Fold-Change Z-score
Prostaglandin G/H synthase 2 (COX-2) DTT PTGS2 7.93E-04 -0.29 -0.34
Prostaglandin G/H synthase 2 (COX-2) DME PTGS2 7.93E-04 -2.88E-01 -3.44E-01
Prostaglandin G/H synthase 1 (COX-1) DME PTGS1 3.97E-03 1.56E-01 4.33E-01
Molecular Expression Atlas (MEA) Jump to Detail Molecular Expression 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: 1049).
2 Free fatty acids regulate insulin secretion from pancreatic beta cells through GPR40. Nature. 2003 Mar 13;422(6928):173-6.
3 Cloning and characterization of the rat free fatty acid receptor GPR120: in vivo effect of the natural ligand on GLP-1 secretion and proliferation of pancreatic beta cells. Naunyn Schmiedebergs Arch Pharmacol. 2008 Jun;377(4-6):515-22.
4 Cox-2 inhibitory effects of naturally occurring and modified fatty acids. J Nat Prod. 2001 Jun;64(6):745-9.
5 Divergent cyclooxygenase responses to fatty acid structure and peroxide level in fish and mammalian prostaglandin H synthases. FASEB J. 2006 Jun;20(8):1097-108.
6 Immunogenic inhibition of prominent ruminal bacteria as a means to reduce lipolysis and biohydrogenation activity in vitro. Food Chem. 2017 Mar 1;218:372-377.
7 Cell-associated alpha-amylases of butyrate-producing Firmicute bacteria from the human colon. Microbiology. 2006 Nov;152(Pt 11):3281-3290.
8 Polyunsaturated fatty acids are FXR ligands and differentially regulate expression of FXR targets. DNA Cell Biol. 2004 Aug;23(8):519-26. doi: 10.1089/1044549041562267.
9 Butyrylcholinesterase expression is regulated by fatty acids in HepG2 cells. Chem Biol Interact. 2016 Nov 25;259(Pt B):276-281.
10 The inhibitory effect of polyunsaturated fatty acids on human CYP enzymes. Life Sci. 2006 Nov 25;79(26):2432-40.
11 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.
12 Conjugated linoleic acid, unlike other unsaturated fatty acids, strongly induces glutathione synthesis without any lipoperoxidation. Br J Nutr. 2006 Nov;96(5):811-9.