Details of the Drug Metabolized by Drug-Metabolizing Enzyme (DME)

General Information of Drug (ID: DR1995)
Drug Name
Gamma-linolenic acid
Synonyms
Acide gamolenique [French]; Acido gamolenico [Spanish]; Acidum gamolenicum [Latin]; GAMOLENIC ACID; Gamolenic acid [INN:BAN]; gamma-Linolenic acid; (6,9,12)-linolenic acid; (6Z,9Z,12Z)-octadeca-6,9,12-trienoic acid; (Z,Z,Z)-6,9,12-Octadecatrienoic acid; 506-26-3; 6,9,12-Octadecatrienoic acid, (Z,Z,Z)-; 6Z,9Z,12Z-octadecatrienoic acid; 78YC2MAX4O; CCRIS 7668; CHEBI:28661; CHEMBL464982; Ligla; UNII-78YC2MAX4O; all-cis-6,9,12-Octadecatrienoic acid; cis,cis,cis-6,9,12-Octadecatrienoic acid; cis-Delta(6,9,12)-octadecatrienoic acid
Indication Neurodermatitis [ICD11: EA83] Phase 4 [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 278.4 Topological Polar Surface Area 37.3
Heavy Atom Count 20 Rotatable Bond Count 13
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 2
Cross-matching ID
PubChem CID
5280933
PubChem SID
8661 ; 615077 ; 841809 ; 7850008 ; 7979368 ; 8144304 ; 8616448 ; 12014288 ; 14775234 ; 24882200 ; 24896312 ; 26754623 ; 26754624 ; 29216151 ; 39289902 ; 47290899 ; 47885167 ; 49998727 ; 50110102 ; 51068121 ; 51091551 ; 53787075 ; 57260207 ; 57264360 ; 57357934 ; 85787690 ; 87572103 ; 91700727 ; 92298626 ; 92309754 ; 99300668 ; 99302186 ; 103636892 ; 104046527 ; 104115203 ; 113854242 ; 119525823 ; 124799300 ; 126524717 ; 134976478 ; 137006167 ; 141706287 ; 144205388 ; 162180888 ; 163781850 ; 164223441 ; 164816041 ; 175266274 ; 178101421 ; 179117054
ChEBI ID
CHEBI:28661
CAS Number
506-26-3
TTD Drug ID
D0UE9X
Formula
C18H30O2
Canonical SMILES
CCCCCC=CCC=CCC=CCCCCC(=O)O
InChI
1S/C18H30O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h6-7,9-10,12-13H,2-5,8,11,14-17H2,1H3,(H,19,20)/b7-6-,10-9-,13-12-
InChIKey
VZCCETWTMQHEPK-QNEBEIHSSA-N
The Metabolic Roadmap of This Drug
The Full List of Drug Metabolites (DM) of This Drug
DM Name DM ID PubChem ID Reaction DM Level REF
Dihomo-gamma-linolenic acid DM005934
5280581
Other reaction - Elongation 1 [2]
15-HETrE DM006682
44322431
Oxidation - Cyclooxygenation 2 [2]
AA DM003578
444899
Other reaction - Delta-5-desaturation 2 [2]
Prostaglandin E1 DM006683
5280723
Unclear 2 [2]
Thromboxanes DM006681
114873
Oxidation - Cyclooxygenation 3 [2]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR007206 Gamma-linolenic acid Dihomo-gamma-linolenic acid Other reaction - Elongation ELOVL5 [2]
MR007207 Dihomo-gamma-linolenic acid Arachidonic Acid Other reaction - Delta-5-desaturation FADS1 [2]
MR007209 Dihomo-gamma-linolenic acid 15-HETrE Oxidation - Cyclooxygenation ALOX15 [2]
MR007210 Dihomo-gamma-linolenic acid Prostaglandin E1 Unclear PTGS1 ... [2]
MR007208 Arachidonic Acid Thromboxanes Oxidation - Cyclooxygenation PTGS1 ... [2]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Arachidonate 15-lipoxygenase (ALOX15) DME0403 Homo sapiens
LOX15_HUMAN
1.13.11.33
[2]
Elongation of very long chain fatty acids protein 5 (ELOVL5) DMEN300 Homo sapiens
ELOV5_HUMAN
2.3.1.199
[2]
Fatty acid desaturase 1 (FADS1) DME0202 Homo sapiens
FADS1_HUMAN
1.14.19.44
[2]
Prostaglandin G/H synthase 1 (COX-1) DME0091 Homo sapiens
PGH1_HUMAN
1.14.99.1
[3]
Prostaglandin G/H synthase 2 (COX-2) DME0114 Homo sapiens
PGH2_HUMAN
1.14.99.1
[3]
Experimental Enzyme Kinetic Data of This Drug
DME Name DME Info Kinetic Data Uniprot ID REF
Prostaglandin G/H synthase 1 (COX-1) DME0091 Km = 0.0048 microM
PGH1_HUMAN
[3]
Prostaglandin G/H synthase 2 (COX-2) DME0114 Km = 0.0048 microM
PGH2_HUMAN
[3]
References
1 ClinicalTrials.gov (NCT00878670) Investigation of Efficacy and Safety of EPOGAM.
2 Gamma-linolenic acid, Dihommo-gamma linolenic, Eicosanoids and Inflammatory Processes
3 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.

If you find any error in data or bug in web service, please kindly report it to Dr. Yin and Dr. Li.