Showing metabocard for Gamma-Linolenic acid (BMDB0003073)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (2) Show 2 proteinsXML
Record Information
Version1.0
Creation Date2016-10-03 18:40:48 UTC
Update Date2020-06-04 20:34:00 UTC
BMDB IDBMDB0003073
Secondary Accession Numbers
  • BMDB03073
Metabolite Identification
Common NameGamma-Linolenic acid
DescriptionGamma-Linolenic acid, also known as 18:3 (N-6) or GLA, belongs to the class of organic compounds known as lineolic acids and derivatives. These are derivatives of lineolic acid. Lineolic acid is a polyunsaturated omega-6 18 carbon long fatty acid, with two CC double bonds at the 9- and 12-positions. Gamma-Linolenic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Gamma-Linolenic acid exists in all living organisms, ranging from bacteria to humans. Gamma-Linolenic acid participates in a number of enzymatic reactions, within cattle. In particular, Gamma-Linolenic acid can be biosynthesized from linoleic acid; which is mediated by the enzyme fatty acid desaturase 2. In addition, Gamma-Linolenic acid can be converted into 8,11,14-eicosatrienoic acid; which is mediated by the enzyme elongation OF very long chain fatty acids protein 5. In cattle, Gamma-linolenic acid is involved in the metabolic pathway called the Alpha linolenic Acid and linoleic Acid metabolism pathway. Gamma-Linolenic acid has been found to be associated with several diseases known as colorectal cancer and lung cancer; also gamma-linolenic acid has been linked to the inborn metabolic disorders including isovaleric acidemia.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(6,9,12)-Linolenic acidChEBI
(6Z,9Z,12Z)-Octadecatrienoic acidChEBI
(Z,Z,Z)-6,9,12-Octadecatrienoic acidChEBI
18:3 (N-6)ChEBI
6,9,12-Octadecatrienoic acidChEBI
6-cis,9-cis,12-cis-Octadecatrienoic acidChEBI
all-cis-6,9,12-Octadecatrienoic acidChEBI
C18:3 (N-6)ChEBI
C18:3, N-6,9,12 all-cisChEBI
cis-Delta(6,9,12)-Octadecatrienoic acidChEBI
gamma-LinolensaeureChEBI
Gamoleic acidChEBI
Gamolenic acidChEBI
GLAChEBI
Octadeca-6,9,12-triensaeureChEBI
(6,9,12)-LinolenateGenerator
(6Z,9Z,12Z)-OctadecatrienoateGenerator
(Z,Z,Z)-6,9,12-OctadecatrienoateGenerator
6,9,12-OctadecatrienoateGenerator
6-cis,9-cis,12-cis-OctadecatrienoateGenerator
all-cis-6,9,12-OctadecatrienoateGenerator
cis-delta(6,9,12)-OctadecatrienoateGenerator
cis-Δ(6,9,12)-octadecatrienoateGenerator
cis-Δ(6,9,12)-octadecatrienoic acidGenerator
g-LinolensaeureGenerator
Γ-linolensaeureGenerator
GamoleateGenerator
GamolenateGenerator
g-LinolenateGenerator
g-Linolenic acidGenerator
gamma-LinolenateGenerator
Γ-linolenateGenerator
Γ-linolenic acidGenerator
6(Z),9(Z),12(Z)-OctadecatrienoateHMDB
6(Z),9(Z),12(Z)-Octadecatrienoic acidHMDB
6,9,12-all-cis-OctadecatrienoateHMDB
6,9,12-all-cis-Octadecatrienoic acidHMDB
6Z,9Z,12Z-OctadecatrienoateHMDB
6Z,9Z,12Z-Octadecatrienoic acidHMDB
gamma-Llnolenic acidHMDB
LiglaHMDB
Acid, gamma-linolenicHMDB
Acid, gamolenicHMDB
gamma Linolenic acidHMDB
FA(18:3(6Z,9Z,12Z))HMDB
FA(18:3n6)HMDB
LinolenateHMDB
gamma-Linolenic acidKEGG
(6Z,9Z,12Z)-6,9,12-Octadecatrienoic acidPhytoBank
(Z,Z,Z)-6,9,12-Octatrienoic acidPhytoBank
cis,cis,cis-6,9,12-Octadecatrienoic acidPhytoBank
cis-6,cis-9,cis-12-Octadecatrienoic acidPhytoBank
Chemical FormulaC18H30O2
Average Molecular Weight278.4296
Monoisotopic Molecular Weight278.224580204
IUPAC Name(6Z,9Z,12Z)-octadeca-6,9,12-trienoic acid
Traditional 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
Description belongs to the class of organic compounds known as lineolic acids and derivatives. These are derivatives of lineolic acid. Lineolic acid is a polyunsaturated omega-6 18 carbon long fatty acid, with two CC double bonds at the 9- and 12-positions.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassLineolic acids and derivatives
Direct ParentLineolic acids and derivatives
Alternative Parents
Substituents
  • Octadecanoid
  • Long-chain fatty acid
  • Fatty acid
  • Unsaturated fatty acid
  • Straight chain fatty acid
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
StatusDetected and Quantified
Origin
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cell membrane
  • Cytoplasm
  • Membrane
Physical Properties
StateLiquid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP6.59ALOGPS
logP6.06ChemAxon
logS-6ALOGPS
pKa (Strongest Acidic)4.92ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count13ChemAxon
Refractivity89.64 m³·mol⁻¹ChemAxon
Polarizability33.8 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Biological Properties
Cellular Locations
  • Cell membrane
  • Cytoplasm
  • Membrane
Biospecimen Locations
  • Adipose Tissue
  • Epidermis
  • Milk
  • Oocyte
  • Placenta
  • Platelet
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
Adipose TissueExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
EpidermisExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
MilkDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified2837.338 +/- 682.398 uMNot SpecifiedNot Specified
Normal
    • M. Ferrand et al....
 details
MilkDetected and Quantified2693.675 +/- 574.651 uMNot SpecifiedNot Specified
Normal
    • M. Ferrand et al....
 details
OocyteDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
PlacentaExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
PlateletExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0003073
DrugBank IDDB13854
Phenol Explorer Compound IDNot Available
FooDB IDFDB002943
KNApSAcK IDC00001226
Chemspider ID4444436
KEGG Compound IDC06426
BioCyc IDCPD-8117
BiGG ID48234
Wikipedia LinkGamma-Linolenic_acid
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)Not Available
General References
  1. Jensen RG: The composition of bovine milk lipids: January 1995 to December 2000. J Dairy Sci. 2002 Feb;85(2):295-350. doi: 10.3168/jds.S0022-0302(02)74079-4. [PubMed:11913692 ]
  2. Jensen RG, Ferris AM, Lammi-Keefe CJ: The composition of milk fat. J Dairy Sci. 1991 Sep;74(9):3228-43. doi: 10.3168/jds.S0022-0302(91)78509-3. [PubMed:1779072 ]
  3. Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals (2009). Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375?386. Metabolomics.
  4. M. Ferrand, B. Huquet. S. Barbey, F. Barillet, F. Faucon, H. Larroque, O. Leray, J.M. Trommenschlager, M. Brochard (2011). M. Ferrand et al. Determination of fatty acid profile in cow's milk using mid-infrared spectrometry: Interest of applying a variable selection by genetic algorithms before a PLS regression. Chemometrics and Intelligent Laboratory Systems 106 (2011) 183?189. Chemometrics and Intelligent Laboratory Systems.

Enzymes

Enzyme Details
1. Acyl-CoA 6-desaturase
General function:
Lipid transport and metabolism
Specific function:
Acts as a fatty acyl-coenzyme A (CoA) desaturase that introduces a cis double bond at carbon 6 of the fatty acyl chain. Involved in biosynthesis of highly unsaturated fatty acids (HUFA) from the essential polyunsaturated fatty acids (PUFA) linoleic acid (LA) (18:2n-6) and alpha-linolenic acid (ALA) (18:3n-3) precursors. Catalyzes the first and rate limiting step in this pathway which is the desaturation of LA (18:2n-6) and ALA (18:3n-3) into gamma-linoleate (GLA) (18:3n-6) and stearidonate (18:4n-3), respectively (By similarity). Subsequently, in the biosynthetic pathway of HUFA n-3 series, desaturates tetracosapentaenoate (24:5n-3) to tetracosahexaenoate (24:6n-3), which is then converted to docosahexaenoate (DHA)(22:6n-3), an important lipid for nervous system function (By similarity). Desaturates palmitate to produce the mono-unsaturated fatty acid sapienate, the most abundant fatty acid in sebum (By similarity). Also desaturates (11E)-octadecenoate (trans-vaccenoate)(18:1n-9), a metabolite in the biohydrogenation pathway of LA (18:2n-6) (By similarity).
Gene Name:
FADS2
Uniprot ID:
A4FV48
Molecular weight:
52533.0
Reactions
Linoleic acid → Gamma-Linolenic aciddetails
Enzyme Details
2. Elongation of very long chain fatty acids protein 5
General function:
Not Available
Specific function:
Catalyzes the first and rate-limiting reaction of the four reactions that constitute the long-chain fatty acids elongation cycle. This endoplasmic reticulum-bound enzymatic process allows the addition of 2 carbons to the chain of long- and very long-chain fatty acids (VLCFAs) per cycle. Condensing enzyme that acts specifically toward polyunsaturated acyl-CoA with the higher activity toward C18:3(n-6) acyl-CoA. May participate in the production of monounsaturated and of polyunsaturated VLCFAs of different chain lengths that are involved in multiple biological processes as precursors of membrane lipids and lipid mediators (By similarity). In conditions where the essential linoleic and alpha linoleic fatty acids are lacking it is also involved in the synthesis of Mead acid from oleic acid (By similarity).
Gene Name:
ELOVL5
Uniprot ID:
Q2KJD9
Molecular weight:
35377.0
Reactions
Gamma-Linolenic acid → 8,11,14-Eicosatrienoic aciddetails