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Record Information
Version3.6
Creation Date2006-05-22 15:12:30 UTC
Update Date2013-02-09 00:12:16 UTC
HMDB IDHMDB03073
Secondary Accession NumbersNone
Metabolite Identification
Common NameGamma-Linolenic acid
DescriptionGamma-Linolenic acid is an omega-6 fatty acid produced in the body as the delta 6-desaturase metabolite of linoleic acid. It is converted to dihomo-gamma-linolenic acid, a biosynthetic precursor of monoenoic prostaglandins such as PGE1. (From Merck Index, 11th ed) -- Pubchem.
Structure
Thumb
Synonyms
  1. (6,9,12)-linolenate
  2. (6,9,12)-linolenic acid
  3. (6Z,9Z,12Z)-Octadecatrienoate
  4. (6Z,9Z,12Z)-Octadecatrienoic acid
  5. (Z,Z,Z)-6,9,12-Octadecatrienoate
  6. (Z,Z,Z)-6,9,12-Octadecatrienoic acid
  7. 6(Z),9(Z),12(Z)-Octadecatrienoate
  8. 6(Z),9(Z),12(Z)-Octadecatrienoic acid
  9. 6,9,12-All-cis-Octadecatrienoate
  10. 6,9,12-All-cis-Octadecatrienoic acid
  11. 6,9,12-Octadecatrienoate
  12. 6,9,12-Octadecatrienoic acid
  13. 6Z,9Z,12Z-Octadecatrienoate
  14. 6Z,9Z,12Z-Octadecatrienoic acid
  15. All-cis-6,9,12-octadecatrienoate
  16. All-cis-6,9,12-octadecatrienoic acid
  17. cis-delta(6,9,12)-Octadecatrienoate
  18. cis-delta(6,9,12)-Octadecatrienoic acid
  19. gamma-Linolenate
  20. gamma-Linolenic acid
  21. gamma-Llnolenic acid
  22. Ligla
Chemical FormulaC18H30O2
Average Molecular Weight278.4296
Monoisotopic Molecular Weight278.224580204
IUPAC Name(6Z,9Z,12Z)-octadeca-6,9,12-trienoic acid
Traditional IUPAC Namegamma-linolenic acid
CAS Registry Number506-26-3
SMILES
CCCCC\C=C/C\C=C/C\C=C/CCCCC(O)=O
InChI Identifier
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-
InChI KeyVZCCETWTMQHEPK-QNEBEIHSSA-N
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassLipids
ClassLineolic Acids and Derivatives
Sub ClassN/A
Other Descriptors
  • Aliphatic Acyclic Compounds
  • Organic Compounds
  • Straight Chain Fatty Acids
  • Unsaturated Fatty Acids
Substituents
  • Acyclic Alkene
  • Carboxylic Acid
Direct ParentLineolic Acids and Derivatives
Ontology
StatusDetected and Quantified
Origin
  • Drug
  • Food
  • Plant
Biofunction
  • Cell signaling
  • Fuel and energy storage
  • Fuel or energy source
  • Membrane integrity/stability
Application
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Cytoplasm
  • Extracellular
  • Membrane (predicted from logP)
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
water solubility2.540E-04 g/LALOGPS
logP6.59ALOGPS
logP6.06ChemAxon
logS-6ALOGPS
pKa (strongest acidic)4.92ChemAxon
physiological charge-1ChemAxon
hydrogen acceptor count2ChemAxon
hydrogen donor count1ChemAxon
polar surface area37.3ChemAxon
rotatable bond count13ChemAxon
refractivity89.64ChemAxon
polarizability33.8ChemAxon
Spectra
SpectraGC-MS
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane (predicted from logP)
Biofluid Locations
  • Blood
Tissue Location
  • Adipose Tissue
  • Epidermis
  • Platelet
Pathways
NameSMPDB LinkKEGG Link
Alpha Linolenic Acid and Linoleic Acid MetabolismSMP00018map00592
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified1.08 +/- 1.5 uMAdult (>18 years old)Not SpecifiedNormal details
BloodDetected and Quantified0.310 +/- 0.196 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified1.03 +/- 0.005 uMAdult (>18 years old)BothNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB002943
KNApSAcK IDC00001226
Chemspider ID4444436
KEGG Compound IDC06426
BioCyc ID5Z13E-15S-91115-TRIHYDROXYPROSTA-
BiGG ID48234
Wikipedia Linkgamma-Linolenic acid
NuGOwiki LinkHMDB03073
Metagene LinkHMDB03073
METLIN ID386
PubChem Compound5280933
PDB IDNot Available
ChEBI ID28661
References
Synthesis ReferenceGema H; Kavadia A; Dimou D; Tsagou V; Komaitis M; Aggelis G Production of gamma-linolenic acid by Cunninghamella echinulata cultivated on glucose and orange peel. Applied microbiology and biotechnology (2002), 58(3), 303-7.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Melnik BC, Plewig G: Is the origin of atopy linked to deficient conversion of omega-6-fatty acids to prostaglandin E1? J Am Acad Dermatol. 1989 Sep;21(3 Pt 1):557-63. Pubmed: 2550526
  2. Levy RJ, Lian JB: gamma-Carboxyglutamate excretion and warfarin therapy. Clin Pharmacol Ther. 1979 May;25(5 Pt 1):562-70. Pubmed: 373941
  3. Bolton-Smith C, Woodward M, Tavendale R: Evidence for age-related differences in the fatty acid composition of human adipose tissue, independent of diet. Eur J Clin Nutr. 1997 Sep;51(9):619-24. Pubmed: 9306089
  4. Purasiri P, Mckechnie A, Heys SD, Eremin O: Modulation in vitro of human natural cytotoxicity, lymphocyte proliferative response to mitogens and cytokine production by essential fatty acids. Immunology. 1997 Oct;92(2):166-72. Pubmed: 9415022
  5. Ziboh VA, Miller CC, Cho Y: Metabolism of polyunsaturated fatty acids by skin epidermal enzymes: generation of antiinflammatory and antiproliferative metabolites. Am J Clin Nutr. 2000 Jan;71(1 Suppl):361S-6S. Pubmed: 10617998
  6. Magnusson G, Boberg M, Cederblad G, Meurling S: Plasma and tissue levels of lipids, fatty acids and plasma carnitine in neonates receiving a new fat emulsion. Acta Paediatr. 1997 Jun;86(6):638-44. Pubmed: 9202801
  7. Kankaanpaa PE, Salminen SJ, Isolauri E, Lee YK: The influence of polyunsaturated fatty acids on probiotic growth and adhesion. FEMS Microbiol Lett. 2001 Jan 15;194(2):149-53. Pubmed: 11164299
  8. Whitaker DK, Cilliers J, de Beer C: Evening primrose oil (Epogam) in the treatment of chronic hand dermatitis: disappointing therapeutic results. Dermatology. 1996;193(2):115-20. Pubmed: 8884146
  9. Kankaanpaa P, Nurmela K, Erkkila A, Kalliomaki M, Holmberg-Marttila D, Salminen S, Isolauri E: Polyunsaturated fatty acids in maternal diet, breast milk, and serum lipid fatty acids of infants in relation to atopy. Allergy. 2001 Jul;56(7):633-8. Pubmed: 11421921
  10. Koletzko B, Sauerwald U, Keicher U, Saule H, Wawatschek S, Bohles H, Bervoets K, Fleith M, Crozier-Willi G: Fatty acid profiles, antioxidant status, and growth of preterm infants fed diets without or with long-chain polyunsaturated fatty acids. A randomized clinical trial. Eur J Nutr. 2003 Oct;42(5):243-53. Pubmed: 14569405
  11. Leigh-Firbank EC, Minihane AM, Leake DS, Wright JW, Murphy MC, Griffin BA, Williams CM: Eicosapentaenoic acid and docosahexaenoic acid from fish oils: differential associations with lipid responses. Br J Nutr. 2002 May;87(5):435-45. Pubmed: 12010583

Enzymes

General function:
Involved in thiolester hydrolase activity
Specific function:
Involved in bile acid metabolism. In liver hepatocytes catalyzes the second step in the conjugation of C24 bile acids (choloneates) to glycine and taurine before excretion into bile canaliculi. The major components of bile are cholic acid and chenodeoxycholic acid. In a first step the bile acids are converted to an acyl-CoA thioester, either in peroxisomes (primary bile acids deriving from the cholesterol pathway), or cytoplasmic at the endoplasmic reticulum (secondary bile acids). May catalyze the conjugation of primary or secondary bile acids, or both. The conjugation increases the detergent properties of bile acids in the intestine, which facilitates lipid and fat-soluble vitamin absorption. In turn, bile acids are deconjugated by bacteria in the intestine and are recycled back to the liver for reconjugation (secondary bile acids). May also act as an acyl-CoA thioesterase that regulates intracellular levels of free fatty acids. In vitro, catalyzes the hydrolysis of long- and very long-chain saturated acyl-CoAs to the free fatty acid and coenzyme A (CoASH), and conjugates glycine to these acyl-CoAs.
Gene Name:
BAAT
Uniprot ID:
Q14032
Molecular weight:
46298.865
General function:
Lipid transport and metabolism
Specific function:
Acyl-CoA thioesterases are a group of enzymes that catalyze the hydrolysis of acyl-CoAs to the free fatty acid and coenzyme A (CoASH), providing the potential to regulate intracellular levels of acyl-CoAs, free fatty acids and CoASH. May play an important physiological function in brain. May play a regulatory role by modulating the cellular levels of fatty acyl-CoA ligands for certain transcription factors as well as the substrates for fatty acid metabolizing enzymes, contributing to lipid homeostasis. Has broad specificity, active towards fatty acyl-CoAs with chain-lengths of C8-C18. Has a maximal activity toward palmitoyl-CoA.
Gene Name:
ACOT7
Uniprot ID:
O00154
Molecular weight:
40454.945
Reactions
Gamma-linolenoyl-CoA + Water → Coenzyme A + Gamma-Linolenic aciddetails
General function:
Involved in thiolester hydrolase activity
Specific function:
Acyl-CoA thioesterases are a group of enzymes that catalyze the hydrolysis of acyl-CoAs to the free fatty acid and coenzyme A (CoASH), providing the potential to regulate intracellular levels of acyl-CoAs, free fatty acids and CoASH. Displays high levels of activity on medium- and long chain acyl CoAs.
Gene Name:
ACOT2
Uniprot ID:
P49753
Molecular weight:
53218.02
Reactions
Gamma-linolenoyl-CoA + Water → Coenzyme A + Gamma-Linolenic aciddetails
General function:
Involved in thiolester hydrolase activity
Specific function:
Acyl-CoA thioesterases are a group of enzymes that catalyze the hydrolysis of acyl-CoAs to the free fatty acid and coenzyme A (CoASH), providing the potential to regulate intracellular levels of acyl-CoAs, free fatty acids and CoASH (By similarity). Succinyl-CoA thioesterase that also hydrolyzes long chain saturated and unsaturated monocarboxylic acyl-CoAs.
Gene Name:
ACOT4
Uniprot ID:
Q8N9L9
Molecular weight:
46326.09
Reactions
Gamma-linolenoyl-CoA + Water → Coenzyme A + Gamma-Linolenic aciddetails
General function:
Involved in acyl-CoA thioesterase activity
Specific function:
Acyl-CoA thioesterases are a group of enzymes that catalyze the hydrolysis of acyl-CoAs to the free fatty acid and coenzyme A (CoASH), providing the potential to regulate intracellular levels of acyl-CoAs, free fatty acids and CoASH. May mediate Nef-induced down-regulation of CD4. Major thioesterase in peroxisomes. Competes with BAAT (Bile acid CoA: amino acid N-acyltransferase) for bile acid-CoA substrate (such as chenodeoxycholoyl-CoA). Shows a preference for medium-length fatty acyl-CoAs (By similarity). May be involved in the metabolic regulation of peroxisome proliferation.
Gene Name:
ACOT8
Uniprot ID:
O14734
Molecular weight:
35914.02
General function:
Involved in thiolester hydrolase activity
Specific function:
Acyl-CoA thioesterases are a group of enzymes that catalyze the hydrolysis of acyl-CoAs to the free fatty acid and coenzyme A (CoASH), providing the potential to regulate intracellular levels of acyl-CoAs, free fatty acids and CoASH. Active towards fatty acyl-CoA with chain-lengths of C12-C16 (By similarity).
Gene Name:
ACOT1
Uniprot ID:
Q86TX2
Molecular weight:
46276.96
Reactions
Gamma-linolenoyl-CoA + Water → Coenzyme A + Gamma-Linolenic aciddetails