Details of the Drug

General Information of Drug (ID: DMSXKYG)

Drug Name
Gamma-homolinolenic acid
Synonyms
DGLA; BML3-B11; Ro 12-1989; Star GLA (GNC); Bishomo-gamma-linolenic acid; C 20:3 n-6; Dihomo-gamma-linolenic acid; Homo-gamma-linolenic acid; Homo-gamma-linolensaeure; Tona-lean 1000 CLA (Action Labs); Cis-8,11,14-Eicosatrienoic Acid; Eicosa-8Z,11Z,14Z-trienoic acid; All-cis-8,11,14-Eicosatrienoic acid; All-cis-8,11,14-icosatrienoic acid; All-cis-Eicosa-8,11,14-triensaeure; Cis,cis,cis-8,11,14-Eicosatrienoic acid; Cis-8,cis-11,cis-14-Eicosatrienoic acid; (8E,11E,14E)-8,11,14-Icosatrienoic acid; (8Z,11Z,14Z)-Icosatrienoic acid; (8Z,11Z,14Z)-icosa-8,11,14-trienoic acid; (Z,Z,Z)-8,11,14-Eicosatrienoate; (Z,Z,Z)-8,11,14-Eicosatrienoic acid; (Z,Z,Z)-8,11,14-Icosatrienoate; (Z,Z,Z)-8,11,14-Icosatrienoicacid; 20:3, n-6,9,12 all-cis; 8, 11, 14-eicosatrienoic acid; 8,11,14-Eicosatrienoate; 8,11,14-Eicosatrienoic acid; 8,11,14-Eicosatrienoic acid, (8Z,11Z,14Z)-(9CI); 8,11,14-Eicosatrienoic acid, (Z,Z,Z)-(8CI); 8,11,14-Icosatrienoate; 8,11,14-all-cis-Eicosatrienoic acid; 8c,11c,14c-Eicosatriensaeure; 8c,11c,14c-eicosatrienoic acid
Indication
Disease Entry ICD 11 Status REF
Malnutrition 5B50-5B71 Approved [1]
Therapeutic Class
Dietary supplement
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 2 Molecular Weight (mw) 306.5
Topological Polar Surface Area (xlogp) 7.2
Rotatable Bond Count (rotbonds) 15
Hydrogen Bond Donor Count (hbonddonor) 1
Hydrogen Bond Acceptor Count (hbondacc) 2
Chemical Identifiers
Formula
C20H34O2
IUPAC Name
(8Z,11Z,14Z)-icosa-8,11,14-trienoic acid
Canonical SMILES
CCCCC/C=C\\C/C=C\\C/C=C\\CCCCCCC(=O)O
InChI
InChI=1S/C20H34O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20(21)22/h6-7,9-10,12-13H,2-5,8,11,14-19H2,1H3,(H,21,22)/b7-6-,10-9-,13-12-
InChIKey
HOBAELRKJCKHQD-QNEBEIHSSA-N
Cross-matching ID
PubChem CID
5280581
ChEBI ID
CHEBI:53486
CAS Number
1783-84-2
DrugBank ID
DB00154
TTD ID
D0O1TC
INTEDE ID
DR1994

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Prostaglandin G/H synthase 1 (COX-1) TT8NGED PGH1_HUMAN Inhibitor [2], [3], [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]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

Molecular Expression Atlas of This Drug

The Studied Disease Malnutrition
ICD Disease Classification 5B50-5B71
Molecule Name Molecule Type Gene Name p-value Fold-Change Z-score
Prostaglandin G/H synthase 1 (COX-1) DTT PTGS1 3.97E-03 0.16 0.43
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 Treatment of rheumatoid arthritis with gammalinolenic acid. Ann Intern Med. 1993 Nov 1;119(9):867-73.
2 Differential metabolism of dihomo-gamma-linolenic acid and arachidonic acid by cyclo-oxygenase-1 and cyclo-oxygenase-2: implications for cellular synthesis of prostaglandin E1 and prostaglandin E2. Biochem J. 2002 Jul 15;365(Pt 2):489-96.
3 Structure of eicosapentaenoic and linoleic acids in the cyclooxygenase site of prostaglandin endoperoxide H synthase-1. J Biol Chem. 2001 Oct 5;276(40):37547-55.
4 Mutational and X-ray crystallographic analysis of the interaction of dihomo-gamma -linolenic acid with prostaglandin endoperoxide H synthases. J Biol Chem. 2001 Mar 30;276(13):10358-65.
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 Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675.
7 Peroxidative free radical formation and O-demethylation of etoposide(VP-16) and teniposide(VM-26). Biochem Biophys Res Commun. 1986 Feb 26;135(1):215-20.
8 Structural basis of fatty acid substrate binding to cyclooxygenase-2. J Biol Chem. 2010 Jul 16;285(29):22152-63.
9 Health implications of high dietary omega-6 polyunsaturated Fatty acids. J Nutr Metab. 2012;2012:539426.
10 PharmGKB summary: very important pharmacogene information for PTGS2. Pharmacogenet Genomics. 2011 Sep;21(9):607-13.
11 The C50T polymorphism of the cyclooxygenase-1 gene and the risk of thrombotic events during low-dose therapy with acetyl salicylic acid. Thromb Haemost. 2008 Jul;100(1):70-5.
12 Comparative inhibitory activity of rofecoxib, meloxicam, diclofenac, ibuprofen, and naproxen on COX-2 versus COX-1 in healthy volunteers. J Clin Pharmacol. 2000 Oct;40(10):1109-20.
13 How many drug targets are there Nat Rev Drug Discov. 2006 Dec;5(12):993-6.
14 Cox-2 inhibitory effects of naturally occurring and modified fatty acids. J Nat Prod. 2001 Jun;64(6):745-9.
15 Comparison of cyclooxygenase inhibitory activity and ocular anti-inflammatory effects of ketorolac tromethamine and bromfenac sodium. Curr Med Res Opin. 2006 Jun;22(6):1133-40.
16 Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services.
17 Ouellet M, Percival MD: Effect of inhibitor time-dependency on selectivity towards cyclooxygenase isoforms. Biochem J. 1995 Feb 15;306 ( Pt 1):247-51.
18 Differential binding mode of diverse cyclooxygenase inhibitors. J Mol Graph Model. 2002 Mar;20(5):359-71.
19 Fenbufen based 3-[5-(substituted aryl)-1,3,4-oxadiazol-2-yl]-1-(biphenyl-4-yl)propan-1-ones as safer antiinflammatory and analgesic agents. Eur J Med Chem. 2009 Sep;44(9):3798-804.