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]
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) 13
Hydrogen Bond Donor Count (hbonddonor) 1
Hydrogen Bond Acceptor Count (hbondacc) 2
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
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]

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]
Molecular Interaction Atlas (MIA) 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.