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]
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) 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
CHEMBL464982
CAS Number
506-26-3
UNII
78YC2MAX4O
DrugBank ID
DB13854
TTD ID
D0UE9X
INTEDE ID
DR1995
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Drug Pharmacogenomic Perturbation (DPP)NEW Click to Jump to the Detailed DPP Information of This Drug
Drug ADMET Endpoint Profile (DAE)NEW Click to Jump to the Detailed DAE Information of This Drug

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]
Clathrin light chain A (CLTA) OTLHOXMQ CLCA_HUMAN Gene/Protein Processing [4]
Ferritin heavy chain (FTH1) OT6IFS0O FRIH_HUMAN Gene/Protein Processing [4]
Histone H2A type 1-C (H2AC6) OTF3YK7V H2A1C_HUMAN Gene/Protein Processing [4]
Hsc70-interacting protein (ST13) OTNML6UP F10A1_HUMAN Gene/Protein Processing [4]
Metallothionein-1G (MT1G) OTAV1OCR MT1G_HUMAN Gene/Protein Processing [4]
Mitogen-activated protein kinase 3 (MAPK3) OTCYKGKO MK03_HUMAN Gene/Protein Processing [5]
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 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.