Showing metabocard for Gamma-Linolenic acid (BMDB0003073)

IdentificationTaxonomyPhysical propertiesSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-10-03 18:40:48 UTC
Update Date2020-06-04 20:34:00 UTC
MCDB ID BMDB0003073
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
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
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-005c-9800000000-7b6e7a36b048f5ed69bd2014-06-16View Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00b9-9300000000-254ecb989081fdc719d22017-09-12View Spectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-005c-9800000000-7b6e7a36b048f5ed69bd2017-09-12View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9650000000-eec5566c0f0f90bf00492017-09-01View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-007c-9431000000-b239852c91e5676687802017-10-06View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12View Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-005l-0902100000-6fc8730bd28daa779b662017-08-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 30V, Negativesplash10-005l-0902100000-6fc8730bd28daa779b662017-08-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-005l-0902100000-6fc8730bd28daa779b662017-08-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-005l-0902100000-6fc8730bd28daa779b662017-08-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-004i-0090000000-143e6ddfa05656a4c4da2017-09-12View Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 30V, Negativesplash10-004i-0090000000-0b9ba563ad074fe141e82017-09-12View Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-004i-0090000000-63bf7d731625d55779782017-09-12View Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-004i-0090000000-fbc4e202a8b26c91dc9e2017-09-12View Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-004i-0090000000-b56d00321ab0921fe7b72017-09-12View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-004i-0090000000-dcae4273443fd52bbb032017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-004i-0090000000-143e6ddfa05656a4c4da2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-004i-0090000000-0b9ba563ad074fe141e82017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-004i-0090000000-63bf7d731625d55779782017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 10V, positivesplash10-004i-0090000000-370b301c8afc435a0ce12020-07-21View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 20V, positivesplash10-003s-9850000000-54163d6f895368b9032c2020-07-21View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 40V, positivesplash10-001i-9000000000-e6cdb81ac5675944be822020-07-21View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-003s-9750000000-d1947011d4fc6a28a1352021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-004i-0090000000-0b9ba563ad074fe141e82021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-004i-0090000000-370b301c8afc435a0ce12021-09-20View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01t9-0190000000-6b136607b48b316678012016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01q9-4790000000-5046458d5d3e3c2285182016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05mo-8930000000-852d50a19eb0b0df729b2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0090000000-ab643cae783eb66bf1312016-08-04View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0059-1090000000-abce276de392be9d7d3f2016-08-04View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9230000000-40a41feed498373e54d22016-08-04View Spectrum
MSMass Spectrum (Electron Ionization)splash10-00nf-9200000000-cf911df79059a750cb2a2015-03-01View Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, H2O, predicted)Not Available2022-08-22View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Not Available2022-08-22View Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, H2O, predicted)Not Available2022-08-22View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Not Available2022-08-22View Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, H2O, predicted)Not Available2022-08-22View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Not Available2022-08-22View Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, H2O, predicted)Not Available2022-08-22View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Not Available2022-08-22View Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, predicted)Not Available2022-08-22View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Not Available2022-08-22View Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, H2O, predicted)Not Available2022-08-22View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Not Available2022-08-22View Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, H2O, predicted)Not Available2022-08-22View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Not Available2022-08-22View Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, H2O, predicted)Not Available2022-08-22View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Not Available2022-08-22View Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, H2O, predicted)Not Available2022-08-22View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Not Available2022-08-22View Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, H2O, predicted)Not Available2022-08-22View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Not Available2022-08-22View Spectrum
Concentrations
StatusValueReferenceDetails
Detected and Quantified2837 +/- 682 uMTotal fatty acid
  • M. Ferrand et al....
 details
Detected and Quantified2694 +/- 574 uMTotal fatty acid
  • M. Ferrand et al....
 details
Detected but not QuantifiedNot Applicable details
HMDB IDHMDB0003073
DrugBank IDDB13854
Phenol Explorer Compound IDNot Available
FoodDB 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)Download (PDF)
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.