Human Metabolome Database Version 3.5

Showing metabocard for Gamma-Linolenic acid (HMDB03073)

Record Information
Version 3.5
Creation Date 2006-05-22 09:12:30 -0600
Update Date 2013-02-08 17:12:16 -0700
HMDB ID HMDB03073
Secondary Accession Numbers None
Metabolite Identification
Common Name Gamma-Linolenic acid
Description Gamma-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
Download: MOL | SDF | PDB | SMILES | InChI
Display: 2D Structure | 3D Structure
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 Formula C18H30O2
Average Molecular Weight 278.4296
Monoisotopic Molecular Weight 278.224580204
IUPAC Name (6Z,9Z,12Z)-octadeca-6,9,12-trienoic acid
Traditional IUPAC Name gamma-linolenic acid
CAS Registry Number 506-26-3
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 Key VZCCETWTMQHEPK-QNEBEIHSSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Lipids
Class Lineolic Acids and Derivatives
Sub Class N/A
Other Descriptors
  • Aliphatic Acyclic Compounds
  • Organic Compounds
  • Straight Chain Fatty Acids
  • Unsaturated Fatty Acids
Substituents
  • Acyclic Alkene
  • Carboxylic Acid
Direct Parent Lineolic Acids and Derivatives
Ontology
Status Detected 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
State Solid
Experimental Properties
Property Value Reference
Melting Point Not Available Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
Water Solubility 2.540E-04 g/L ALOGPS
LogP 6.59 ALOGPS
LogP 6.06 ChemAxon
LogS -6.04 ALOGPS
pKa (strongest acidic) 4.92 ChemAxon
Hydrogen Acceptor Count 2 ChemAxon
Hydrogen Donor Count 1 ChemAxon
Polar Surface Area 37.3 A2 ChemAxon
Rotatable Bond Count 13 ChemAxon
Refractivity 89.64 ChemAxon
Polarizability 33.8 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge -1 ChemAxon
Spectra
MS/MS Spectrum GC-MS
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane (predicted from logP)
Biofluid Locations
  • Blood
Tissue Location
  • Epidermis
  • Adipose Tissue
  • Platelet
Pathways
Name SMPDB Link KEGG Link
Alpha Linolenic Acid and Linoleic Acid Metabolism SMP00018 map00592 Link_out
Normal Concentrations
Biofluid Status Value Age Sex Condition Reference
Blood Detected and Quantified
1.08 +/- 1.5 uM Adult (>18 years old) Not Specified Normal
Blood Detected and Quantified
0.310 +/- 0.196 uM Adult (>18 years old) Both Normal
Blood Detected and Quantified
1.03 +/- 0.005 uM Adult (>18 years old) Both Normal
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
DrugBank Metabolite ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB002943
KNApSAcK ID C00001226 Link_out
Chemspider ID 4444436 Link_out
KEGG Compound ID C06426 Link_out
BioCyc ID 5Z13E-15S-91115-TRIHYDROXYPROSTA- Link_out
BiGG ID 48234 Link_out
Wikipedia Link gamma-Linolenic acid Link_out
NuGOwiki Link HMDB03073 Link_out
Metagene Link HMDB03073 Link_out
METLIN ID 386 Link_out
PubChem Compound 5280933 Link_out
PDB ID Not Available
ChEBI ID 28661 Link_out
References
Synthesis Reference Gema 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. Levy RJ, Lian JB: gamma-Carboxyglutamate excretion and warfarin therapy. Clin Pharmacol Ther. 1979 May;25(5 Pt 1):562-70. Pubmed: 373941 Link_out
  2. 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 Link_out
  3. 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 Link_out
  4. 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 Link_out
  5. 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 Link_out
  6. 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 Link_out
  7. 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 Link_out
  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 Link_out
  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 Link_out
  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 Link_out
  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 Link_out

Enzymes
Name: Bile acid-CoA:amino acid N-acyltransferase
Reactions: Not Available
Gene Name: BAAT
Uniprot ID: Q14032 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytosolic acyl coenzyme A thioester hydrolase
Reactions:
Gamma-linolenoyl-CoA + Water unknown Coenzyme A + Gamma-Linolenic acid details
Gene Name: ACOT7
Uniprot ID: O00154 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Acyl-coenzyme A thioesterase 2, mitochondrial
Reactions:
Gamma-linolenoyl-CoA + Water unknown Coenzyme A + Gamma-Linolenic acid details
Gene Name: ACOT2
Uniprot ID: P49753 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Acyl-coenzyme A thioesterase 4
Reactions:
Gamma-linolenoyl-CoA + Water unknown Coenzyme A + Gamma-Linolenic acid details
Gene Name: ACOT4
Uniprot ID: Q8N9L9 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Acyl-coenzyme A thioesterase 8
Reactions: Not Available
Gene Name: ACOT8
Uniprot ID: O14734 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Acyl-coenzyme A thioesterase 1
Reactions:
Gamma-linolenoyl-CoA + Water unknown Coenzyme A + Gamma-Linolenic acid details
Gene Name: ACOT1
Uniprot ID: Q86TX2 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA