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]
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Therapeutic Class

Dietary supplement

Drug Type

Small molecular drug

Structure

3D MOL

2D MOL

#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: 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]

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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]

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Molecular Interaction Atlas (MIA)

MIA Detail

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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)

MEA Detail

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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.