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targets (2) carriers (1)
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Identification
Name gamma-Homolinolenic acid
Accession Number DB00154 (NUTR00032)
Type small molecule
Groups approved, nutraceutical
Description

A 20-carbon-chain fatty acid, unsaturated at positions 8, 11, and 14. It differs from arachidonic acid, 5,8,11,14-eicosatetraenoic acid, only at position 5. [PubChem]
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
(Z,Z,Z)-8,11,14-Eicosatrienoic acid
8,11,14-Eicosatrienoic Acid
cis-8,11,14-Eicosatrienoic acid
DGLA
Dihomo-gamma-linolenic acid
Homo-gamma-linolenic acid
Salts Not Available
Brand names
Name Company
Star GLA (GNC)
Tona-lean 1000 CLA (Action Labs)
Brand mixtures Not Available
Categories
  • Dietary supplement
  • Micronutrient
CAS number 1783-84-2
Weight Average: 306.4828
Monoisotopic: 306.255880332
Chemical Formula C20H34O2
InChI Key InChIKey=HOBAELRKJCKHQD-QNEBEIHSSA-N
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-
Plain Text
IUPAC Name
(8Z,11Z,14Z)-icosa-8,11,14-trienoic acid
SMILES
CCCCC\C=C/C\C=C/C\C=C/CCCCCCC(O)=O
Plain Text
Mass Spec Not Available
Taxonomy
Kingdom Organic
Classes
  • Fatty Acids
Substructures
  • Hydroxy Compounds
  • Alkanes and Alkenes
  • Acetates
  • Carboxylic Acids and Derivatives
  • Fatty Acids
Pharmacology
Indication For nutritional supplementation, also for treating dietary shortage or imbalance
Pharmacodynamics Dihomo gamma-linolenic acid or DHLA is an n-6 (omega-6) polyunsaturated fatty acid. It is comprised of 20 carbon atoms and three double bonds. DHLA is a byproduct of the 18 carbon gamma-linolenic acid (GLA). DHLA is then converted into prostaglandin E1 (PGE1). PGE1 inhibits platelet aggregation and also exerts a vasodilatory effect.
Mechanism of action DHLA (or DGLA) is a precursor in the synthesis of prostaglandin E1 (PGE1) as well as the series-3 prostaglandins. It also serves as a precursor in the synthesis of eicosapentaenoic acid (EPA). EPA is a precursor of the series-3 prostaglandins, the series-5 leukotrienes and the series-3 thromboxanes. These eicosanoids have anti-thrombogenic, anti-inflammatory and anti-atherogenic properties. PGE1 inhibits platelet aggregation and has a vasodilation action. DHLA has also been shown to reduce the production/activity of tumor necrosis factor alpha.
Absorption Not Available
Volume of distribution Not Available
Protein binding Not Available
Metabolism Not Available
Route of elimination Not Available
Half life Not Available
Clearance Not Available
Toxicity Not Available
Affected organisms
  • Humans and other mammals
Pathways Not Available
Pharmacoeconomics
Manufacturers Not Available
Packagers Not Available
Dosage forms
Form Route Strength
Capsule Oral
Prices Not Available
Patents Not Available
Properties
State solid
Experimental Properties
Property Value Source
logP 6.8 Not Available
Predicted Properties
Property Value Source
water solubility 7.71e-05 g/l ALOGPS
logP 7.24 ALOGPS
logP 6.95 ChemAxon
logS -6.6 ALOGPS
pKa (strongest acidic) 4.89 ChemAxon
physiological charge -1 ChemAxon
hydrogen acceptor count 2 ChemAxon
hydrogen donor count 1 ChemAxon
polar surface area 37.3 ChemAxon
rotatable bond count 15 ChemAxon
refractivity 98.84 ChemAxon
polarizability 39.01 ChemAxon
References
Synthesis Reference Not Available
General Reference Not Available
External Links
Resource Link
KEGG Compound C03242 Link_out
PubChem Compound 5280581 Link_out
PubChem Substance 46508866 Link_out
ChemSpider 4444199 Link_out
Therapeutic Targets Database DAP000806 Link_out
PharmGKB PA164743249 Link_out
HET LAX Link_out
PDRhealth http://www.pdrhealth.com/drug_info/nmdrugprofiles/nutsupdrugs/gam_0120.shtml Link_out
ATC Codes Not Available
AHFS Codes Not Available
PDB Entries
FDA label Not Available
MSDS show (71 KB)
Interactions
Drug Interactions Not Available
Food Interactions Not Available
Targets

1. Prostaglandin G/H synthase 1

Pharmacological action: yes
Actions: inhibitor

May play an important role in regulating or promoting cell proliferation in some normal and neoplastically transformed cells

Organism class: human
UniProt ID: P23219 Link_out
Gene: PTGS1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Levin G, Duffin KL, Obukowicz MG, Hummert SL, Fujiwara H, Needleman P, Raz A: 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. Pubmed
  2. Das UN: Can COX-2 inhibitor-induced increase in cardiovascular disease risk be modified by essential fatty acids? J Assoc Physicians India. 2005 Jul;53:623-7. Pubmed
  3. Das UN: COX-2 inhibitors and metabolism of essential fatty acids. Med Sci Monit. 2005 Jul;11(7):RA233-7. Epub 2005 Jun 29. Pubmed
  4. Thuresson ED, Malkowski MG, Lakkides KM, Rieke CJ, Mulichak AM, Ginell SL, Garavito RM, Smith WL: Mutational and X-ray crystallographic analysis of the interaction of dihomo-gamma -linolenic acid with prostaglandin endoperoxide H synthases. J Biol Chem. 2001 Mar 30;276(13):10358-65. Epub 2000 Dec 19. Pubmed
  5. Malkowski MG, Thuresson ED, Lakkides KM, Rieke CJ, Micielli R, Smith WL, Garavito RM: Structure of eicosapentaenoic and linoleic acids in the cyclooxygenase site of prostaglandin endoperoxide H synthase-1. J Biol Chem. 2001 Oct 5;276(40):37547-55. Epub 2001 Jul 27. Pubmed
  6. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. Pubmed

2. Prostaglandin G/H synthase 2

Pharmacological action: yes

May have a role as a major mediator of inflammation and/or a role for prostanoid signaling in activity-dependent plasticity

Organism class: human
UniProt ID: P35354 Link_out
Gene: PTGS2 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Das UN: Can COX-2 inhibitor-induced increase in cardiovascular disease risk be modified by essential fatty acids? J Assoc Physicians India. 2005 Jul;53:623-7. Pubmed
  2. Levin G, Duffin KL, Obukowicz MG, Hummert SL, Fujiwara H, Needleman P, Raz A: 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. Pubmed
  3. Das UN: COX-2 inhibitors and metabolism of essential fatty acids. Med Sci Monit. 2005 Jul;11(7):RA233-7. Epub 2005 Jun 29. Pubmed
  4. Thuresson ED, Malkowski MG, Lakkides KM, Rieke CJ, Mulichak AM, Ginell SL, Garavito RM, Smith WL: Mutational and X-ray crystallographic analysis of the interaction of dihomo-gamma -linolenic acid with prostaglandin endoperoxide H synthases. J Biol Chem. 2001 Mar 30;276(13):10358-65. Epub 2000 Dec 19. Pubmed
Carriers

1. Fatty acid-binding protein, brain

B-FABP could be involved in the transport of a so far unknown hydrophobic ligand with potential morphogenic activity during CNS development. It is required for the establishment of the radial glial fiber system in developing brain, a system that is necessary for the migration of immature neurons to establish cortical layers

UniProt ID: O15540 Link_out
Gene: FABP7 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed
Comments
Drug created on June 13, 2005 07:24 / Updated on February 08, 2013 16:19