Details of the Drug

General Information of Drug (ID: DMQN30Z)

Drug Name

Gamolenic acid

Synonyms

gamma-Linolenic acid; GAMOLENIC ACID; 506-26-3; (6Z,9Z,12Z)-octadeca-6,9,12-trienoic acid; (Z,Z,Z)-6,9,12-Octadecatrienoic acid; CCRIS 7668; UNII-78YC2MAX4O; Acidum gamolenicum [Latin]; Acido gamolenico [Spanish]; Acide gamolenique [French]; 6,9,12-Octadecatrienoic acid, (Z,Z,Z)-; Gamolenic acid [INN:BAN]; (6,9,12)-linolenic acid; all-cis-6,9,12-Octadecatrienoic acid; cis,cis,cis-6,9,12-Octadecatrienoic acid; 6Z,9Z,12Z-octadecatrienoic acid; 78YC2MAX4O; cis-Delta(6,9,12)-octadecatrienoic acid; CHEMBL464982; CHEBI:28661; Epogam (TN); gamma-linolenic acid

Indication

Disease Entry	ICD 11	Status	REF
Allergy	4A80-4A85	Approved	[1]
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ATC Code

D11AX02: Gamolenic acid

D11AX: Other dermatologicals

D11A: OTHER DERMATOLOGICAL PREPARATIONS

D11: OTHER DERMATOLOGICAL PREPARATIONS

D: DERMATOLOGICALS

Drug Type

Small molecular drug

Structure

3D MOL

2D MOL

#Ro5 Violations (Lipinski): 2

Molecular Weight (mw)

278.4

Logarithm of the Partition Coefficient (xlogp)

5.9

Rotatable Bond Count (rotbonds)

Hydrogen Bond Donor Count (hbonddonor)

Hydrogen Bond Acceptor Count (hbondacc)

ADMET Property

Metabolism: The drug is metabolized via the elongase [2]

Chemical Identifiers

Formula: C18H30O2
IUPAC Name: (6Z,9Z,12Z)-octadeca-6,9,12-trienoic acid
Canonical SMILES: CCCCC/C=C\\C/C=C\\C/C=C\\CCCCC(=O)O
InChI: 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

Cross-matching ID

PubChem CID: 5280933
ChEBI ID: CHEBI:28661
CAS Number: 506-26-3
UNII: 78YC2MAX4O
DrugBank ID: DB13854
TTD ID: D0UE9X
INTEDE ID: DR1995

Molecular Interaction Atlas of This Drug

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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Drug Off-Target (DOT)

DOT Name	DOT ID	UniProt ID	Interaction	REF
Acid ceramidase (ASAH1)	OT1DNGXL	ASAH1_HUMAN	Gene/Protein Processing	[4]
Aldo-keto reductase family 1 member C1 (AKR1C1)	OTQKR4CM	AK1C1_HUMAN	Gene/Protein Processing	[4]
Aldo-keto reductase family 1 member C4 (AKR1C4)	OTW2MMOF	AK1C4_HUMAN	Gene/Protein Processing	[4]
Amino acid transporter heavy chain SLC3A2 (SLC3A2)	OTBR33M9	4F2_HUMAN	Gene/Protein Processing	[4]
Beta-2-glycoprotein 1 (APOH)	OTFMUX6O	APOH_HUMAN	Gene/Protein Processing	[4]
Beta-hexosaminidase subunit beta (HEXB)	OTROYLCR	HEXB_HUMAN	Gene/Protein Processing	[4]
Caspase-3 (CASP3)	OTIJRBE7	CASP3_HUMAN	Gene/Protein Processing	[5]
Clathrin light chain A (CLTA)	OTLHOXMQ	CLCA_HUMAN	Gene/Protein Processing	[4]
Cyclin-A2 (CCNA2)	OTPHHYZJ	CCNA2_HUMAN	Gene/Protein Processing	[6]
Cyclin-dependent kinase 1 (CDK1)	OTW1SC2N	CDK1_HUMAN	Gene/Protein Processing	[6]

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Molecular Interaction Atlas (MIA)

MIA Detail

Jump to Detail Molecular Interaction Atlas of This Drug

References

1	Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services. 2015
2	White JR Jr, Padowski JM, Zhong Y, Chen G, Luo S, Lazarus P, Layton ME, McPherson S: Pharmacokinetic analysis and comparison of caffeine administered rapidly or slowly in coffee chilled or hot versus chilled energy drink in healthy young adults. Clin Toxicol (Phila). 2016;54(4):308-12. doi: 10.3109/15563650.2016.1146740.
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.
4	Antineoplastic effects of gamma linolenic Acid on hepatocellular carcinoma cell lines. J Clin Biochem Nutr. 2010 Jul;47(1):81-90.
5	Induction of apoptosis in K562/ADM cells by gamma-linolenic acid involves lipid peroxidation and activation of caspase-3. Chem Biol Interact. 2006 Aug 25;162(2):140-8. doi: 10.1016/j.cbi.2006.05.019. Epub 2006 Jun 9.
6	A retinoid X receptor (RXR)-selective retinoid reveals that RXR-alpha is potentially a therapeutic target in breast cancer cell lines, and that it potentiates antiproliferative and apoptotic responses to peroxisome proliferator-activated receptor ligands. Breast Cancer Res. 2004;6(5):R546-55. doi: 10.1186/bcr913. Epub 2004 Jul 23.