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

General Information of Drug (ID: DR1994)
Drug Name
Icosatrienoic acid
Synonyms
Bishomo-gamma-linolenic acid; Cis-8,11,14-eicosatrienoic acid; Dihomo-gamma-linolenic acid; Homo-gamma-linolenic acid; Ro 12-1989; cis-8,11,14-Eicosatrienoic Acid; gamma-Homolinolenic acid; (8Z,11Z,14Z)-Icosatrienoic acid; (8Z,11Z,14Z)-icosa-8,11,14-trienoic acid; (Z,Z,Z)-8,11,14-Eicosatrienoic acid; (Z,Z,Z)-8,11,14-Icosatrienoic acid; 1783-84-2; 8,11,14-Eicosatrienoate; 8,11,14-Eicosatrienoic acid; 8,11,14-Icosatrienoate; 8Z,11Z,14Z-eicosatrienoic acid; DGLA; UNII-FC398RK06S; all-cis-8,11,14-Eicosatrienoic acid; cis,cis,cis-8,11,14-Eicosatrienoic acid
Indication Discovery agent Investigative [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 306.5 Topological Polar Surface Area 37.3
Heavy Atom Count 22 Rotatable Bond Count 15
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 2
Cross-matching ID
PubChem CID
5280581
PubChem SID
6112 ; 841844 ; 7850023 ; 7888613 ; 8616330 ; 14849827 ; 24894557 ; 26754937 ; 26754938 ; 39289665 ; 46508866 ; 47364932 ; 47885171 ; 50110840 ; 50834734 ; 57357798 ; 85787438 ; 87322643 ; 92309702 ; 99300616 ; 99302134 ; 103636894 ; 104046532 ; 104115205 ; 113853558 ; 126524681 ; 134222871 ; 134338087 ; 134978911 ; 137205464 ; 139646151 ; 160963503 ; 179150079 ; 184568160 ; 198986692 ; 225022227 ; 227115049 ; 250134279 ; 252368023 ; 252455426 ; 252457617
ChEBI ID
CHEBI:53486
CAS Number
1783-84-2
TTD Drug ID
D0O1TC
Formula
C20H34O2
Canonical SMILES
CCCCCC=CCC=CCC=CCCCCCCC(=O)O
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
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
AA DM003578
444899
Unclear 1 [3]
Deoxycholic acid DM006904
222528
Unclear 1 [4]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR007504 Icosatrienoic acid Arachidonic acid Unclear Unclear [3]
MR007505 Icosatrienoic acid Deoxycholic acid Unclear Unclear [4]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Prostaglandin G/H synthase 1 (COX-1) DME0091 Homo sapiens
PGH1_HUMAN
1.14.99.1
[2]
Prostaglandin G/H synthase 2 (COX-2) DME0114 Homo sapiens
PGH2_HUMAN
1.14.99.1
[2]
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 = 0.002 microM
PGH1_HUMAN
[2]
Prostaglandin G/H synthase 2 (COX-2) DME0114 Km = 0.002 microM
PGH2_HUMAN
[2]
References
1 Uptake and effect on arachidonic acid oxygenation of some icosaenoic acids in human platelets. Biomed Biochim Acta. 1984;43(8-9):S319-22.
2 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.
3 The metabolism of dihomo-gamma-linolenic acid in man
4 The ratio of dihomo--linolenic acid to deoxycholic acid species is a potential biomarker for the metabolic abnormalities in obesity

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