General
Preferred name
GAMOLENIC ACID
Synonyms
??-Linolenic acid ()
gamma-Linolenic acid ()
??Linolenic acid ()
Epogam ()
γ-Linolenic acid ()
γ-linolenic acid ()
¦Ã-Linolenic acid ()
.gamma.-Linolenic Acid ()
Epogam 80 ()
Epogam 40 ()
Gamma-linolenate ()
18:3(N-6) ()
Efamast 40 ()
Delta-linolenic acid ()
Epoc ()
Gammolin ()
Epogam Paed ()
(6z,9z,12z-octadecatrienoic acid ()
Unigam ()
Sonova 400 ()
Gammalinolenic acid ()
Kentogam ()
Gamma linolenic acid ()
Efamast 80 ()
Lin-Gam ()
.gamma.-linolenic acid ()
NDI 609 ()
C18:3 (n-6) ()
Gamophase ()
Gamolenic-acid ()
Gam-O ()
P&D ID
PD014105
CAS
506-26-3
Tags
natural product
drug
available
Drug indication
Allergy
Drug Status
investigational
approved
Max Phase
4.0
Probe control
Probe control not defined
Orthogonal probes
0
No orthogonal probes found
Similar probes
0
No structurally similar probes found
Structure
P&D probe-likeness score
Structure formats
[[ format ]]
[[ compound[format === 'MOL' ? 'molblock' : format.toLowerCase()] ]]
Description
(extracted from source data)
METABOLISM
Via elongation mediated by elongase (ELOVL5), gamolenic acid is rapidly converted to dihomo-gamma-linolenic acid (DGLA), which is further cyclooxygenated to prostaglandin E1 (PGE1) via COX-1 or COX-2 enzymatic activity depending on the cell type [A32848]. PGE1 may be metabolized to smaller prostaglandin remnants, primarily dicarboxylic acids, which undergo renal excretion [F27]. DGLA may be converted to 15-(S)-hydroxy-8,11,13-eicosatrienoic acid (15-HETrE) by 15-lipoxygenase enzyme [A32848]. ; ; Although the enzymatic pathway is less predominant relative to ELOVL5 in most cells, DGLA may also be converted to arachidonic acid (AA) via delta-5-desaturate activity [A32852], where hydrogen atoms are selectively removed to create new double bonds F27]. Arachidonic acid is a precursor in the biosynthesis of prostaglandin E2, thromboxanes, and leukotrienes, which are potent inflammatory mediators and play an important role in inflammatory pathways.
MOA
Once gamolenic acid (GLA) is absorbed and converted to dihomo-gamolenic acid (DGLA), circulating DGLA fatty acids are converted to several lipid mediators with predominantly anti-inflammatory properties, such as prostaglandin-E1 (PGE1) and 15-HETrE. The anti-inflammatory effects of DGLA are attributed to both the anti-inflammatory properties of DGLA-derived metabolites and the ability of DGLA and its products to compete with arachidonic acid (AA) in the synthesis of pro-inflammatory potent eicosanoid products, such as prostaglandins, thromboxane and leukotrienes [A32848]. Both PGE1 and 15-HETrE are known to suppress inflammation, promote vasodilation, lower blood pressure, inhibit smooth muscle cell proliferation, inhibit platelet aggregation, and exert anti-neoplastic activities [A32848]. PGE1 is a potent vasodilator that binds to surface receptors on smooth muscle cells, increasing intracellular cAMP [F27]. PGE1 is binds to G protein coupled surface PGE (EP) receptors and prostacyclin (IP) receptors as a natural ligand [A32849]. ; ; GLA is proposed to enhance calcium absorption, reduce excretion and increase calcium deposition in bone [A32862]. It is proposed that GLA may suppress tumor growth _in vivo_ by increasing the expression of E-cadherin, a cell-to-cell adhesion molecule that acts as a suppressor of metastasis. Another possible mechanism of tumour suppression is that GLA also reduces tumor-endothelium adhesion, which is a key factor in the establishment of distant metastases, partly by improving gap junction communication within the endothelium [A32849]. By targeting the inflammatory process involved in the pathogenesis of diabetic nephropathy, GLA inhibits the expression of inflammatory mediators that tend be elevated in diabetes, intracellular adhesion molecule-1 (ICAM-1) and monocyte chemoattractant protein-1 (MCP-1), thereby attenuates the recruitment and infiltration of monocytes or macrophages [A32850].
[[ p.pathway_name ]]
[[ compound.targets[tid].gene_name ]]
Compound Sets
21
Cayman Chemical Bioactives
ChEMBL Approved Drugs
ChEMBL Drugs
Concise Guide to Pharmacology 2017/18
Concise Guide to Pharmacology 2019/20
Concise Guide to Pharmacology 2021/22
Concise Guide to Pharmacology 2023/24
Drug Repurposing Hub
DrugBank
DrugBank Approved Drugs
DrugCentral
DrugCentral Approved Drugs
DrugMAP
DrugMAP Approved Drugs
Guide to Pharmacology
LSP-MoA library (Laboratory of Systems Pharmacology)
MedChem Express Bioactive Compound Library
Natural product-based probes and drugs
NPC Screening Collection
Selleckchem Bioactive Compound Library
TargetMol Bioactive Compound Library
[[ a.name ]]
[[ ligand_id ]]
free of charge
External IDs
49
Molecular Weight
278.22
Hydrogen Bond Acceptors
1
Hydrogen Bond Donors
1
Rotatable Bonds
13
Ring Count
0
Aromatic Ring Count
0
cLogP
5.66
TPSA
37.3
Fraction CSP3
0.61
Chiral centers
0.0
Largest ring
0.0
QED
0.35
Structural alerts
0
No structural alerts detected
Related compounds
Custom attributes
(extracted from source data)
Pathway
Metabolism
Metabolic Enzyme/Protease
Target
Endogenous Metabolite
PTGS1, PTGS2
MOA
cyclooxygenase inhibitor, prostanoid receptor agonist
Biosynthetic Origin
Fatty Acid
Therapeutic Indication
Antiallergic
Therapeutic Class
Antiinflammatory
Source data
