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
• Affected Organisms: Humans and other mammals
• Drug Type: Small molecular drug
• #Ro5 Violations (Lipinski): 2:
  Molecular Weight (mw); 306.5
  Logarithm of the Partition Coefficient (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: CHEMBL465183
  CAS Number: 1783-84-2
  UNII: FC398RK06S
  DrugBank ID: DB00154
  TTD ID: D0O1TC
  INTEDE ID: DR1994
• Drug-Molecule Activity Atlas (DMA)NEW: Click to Jump to the Detailed DMA Information of This Drug
• Drug Pharmacogenomic Perturbation (DPP)NEW: Click to Jump to the Detailed DPP Information of This Drug

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]

Drug-Metabolizing Enzyme (DME)

DME Name	DME ID	UniProt ID	MOA	REF
Prostaglandin G/H synthase 2 (COX-2)	DE492CE	PGH2_HUMAN	Substrate	[3]
Prostaglandin G/H synthase 1 (COX-1)	DE073H6	PGH1_HUMAN	Substrate	[3]

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

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] 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.