Livestock Metabolome Database: Showing metabocard for Gamma-Linolenic acid (LMDB00415)

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-07-13 19:49:20 UTC

Update Date

2016-07-20 21:04:05 UTC

Lmdb

LMDB00415

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Gamma-Linolenic acid

Description

gamma-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.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(6,9,12)-Linolenic acid	ChEBI
(6Z,9Z,12Z)-Octadecatrienoic acid	ChEBI
(Z,Z,Z)-6,9,12-Octadecatrienoic acid	ChEBI
18:3 (N-6)	ChEBI
6,9,12-Octadecatrienoic acid	ChEBI
6-cis,9-cis,12-cis-Octadecatrienoic acid	ChEBI
all-cis-6,9,12-Octadecatrienoic acid	ChEBI
C18:3 (N-6)	ChEBI
C18:3, N-6,9,12 all-cis	ChEBI
cis-Delta(6,9,12)-Octadecatrienoic acid	ChEBI
gamma-Linolensaeure	ChEBI
Gamoleic acid	ChEBI
Gamolenic acid	ChEBI
GLA	ChEBI
Octadeca-6,9,12-triensaeure	ChEBI
(6,9,12)-Linolenate	Generator
(6Z,9Z,12Z)-Octadecatrienoate	Generator
(Z,Z,Z)-6,9,12-Octadecatrienoate	Generator
6,9,12-Octadecatrienoate	Generator
6-cis,9-cis,12-cis-Octadecatrienoate	Generator
all-cis-6,9,12-Octadecatrienoate	Generator
cis-delta(6,9,12)-Octadecatrienoate	Generator
cis-Δ(6,9,12)-octadecatrienoate	Generator
cis-Δ(6,9,12)-octadecatrienoic acid	Generator
g-Linolensaeure	Generator
Γ-linolensaeure	Generator
Gamoleate	Generator
Gamolenate	Generator
g-Linolenate	Generator
g-Linolenic acid	Generator
gamma-Linolenate	Generator
Γ-linolenate	Generator
Γ-linolenic acid	Generator
6(Z),9(Z),12(Z)-Octadecatrienoate	HMDB
6(Z),9(Z),12(Z)-Octadecatrienoic acid	HMDB
6,9,12-all-cis-Octadecatrienoate	HMDB
6,9,12-all-cis-Octadecatrienoic acid	HMDB
6Z,9Z,12Z-Octadecatrienoate	HMDB
6Z,9Z,12Z-Octadecatrienoic acid	HMDB
gamma-Llnolenic acid	HMDB
Ligla	HMDB
Acid, gamma-linolenic	HMDB
Acid, gamolenic	HMDB
gamma Linolenic acid	HMDB
FA(18:3(6Z,9Z,12Z))	HMDB
FA(18:3n6)	HMDB
Linolenate	HMDB
gamma-Linolenic acid	KEGG
(6Z,9Z,12Z)-6,9,12-Octadecatrienoic acid	PhytoBank
(Z,Z,Z)-6,9,12-Octatrienoic acid	PhytoBank
cis,cis,cis-6,9,12-Octadecatrienoic acid	PhytoBank
cis-6,cis-9,cis-12-Octadecatrienoic acid	PhytoBank

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 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

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.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Lineolic acids and derivatives

Direct Parent

Lineolic 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 Framework

Aliphatic acyclic compounds

External Descriptors

omega-6 fatty acid (CHEBI:28661 )
linolenic acid (CHEBI:28661 )
Unsaturated fatty acids (C06426 )
Polyunsaturated fatty acids (C06426 )
Unsaturated fatty acids (LMFA01030141 )

Ontology

Status

Detected but not Quantified

Origin

Not Available

Biofunction

Not Available

Application

Not Available

Cellular locations

Not Available

Physical Properties

State

Not Available

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
logP	6.59	ALOGPS
logP	6.06	ChemAxon
logS	-6	ALOGPS
pKa (Strongest Acidic)	4.92	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	37.3 Å²	ChemAxon
Rotatable Bond Count	13	ChemAxon
Refractivity	89.64 m³·mol⁻¹	ChemAxon
Polarizability	33.8 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - GC-MS (1 TMS)	splash10-005c-9800000000-7b6e7a36b048f5ed69bd	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00b9-9300000000-254ecb989081fdc719d2	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-005c-9800000000-7b6e7a36b048f5ed69bd	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9650000000-eec5566c0f0f90bf0049	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-007c-9431000000-b239852c91e567668780	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF 20V, Negative	splash10-005l-0902100000-6fc8730bd28daa779b66	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF 30V, Negative	splash10-005l-0902100000-6fc8730bd28daa779b66	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF 10V, Negative	splash10-005l-0902100000-6fc8730bd28daa779b66	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF , Negative	splash10-005l-0902100000-6fc8730bd28daa779b66	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF 20V, Negative	splash10-004i-0090000000-143e6ddfa05656a4c4da	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF 30V, Negative	splash10-004i-0090000000-0b9ba563ad074fe141e8	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF 10V, Negative	splash10-004i-0090000000-63bf7d731625d5577978	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF 10V, Negative	splash10-004i-0090000000-fbc4e202a8b26c91dc9e	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF , Negative	splash10-004i-0090000000-b56d00321ab0921fe7b7	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-004i-0090000000-dcae4273443fd52bbb03	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-TOF , negative	splash10-004i-0090000000-143e6ddfa05656a4c4da	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-TOF , negative	splash10-004i-0090000000-0b9ba563ad074fe141e8	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-TOF , negative	splash10-004i-0090000000-63bf7d731625d5577978	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF 10V, positive	splash10-004i-0090000000-370b301c8afc435a0ce1	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF 20V, positive	splash10-003s-9850000000-54163d6f895368b9032c	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF 40V, positive	splash10-001i-9000000000-e6cdb81ac5675944be82	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-003s-9750000000-d1947011d4fc6a28a135	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-004i-0090000000-0b9ba563ad074fe141e8	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-004i-0090000000-370b301c8afc435a0ce1	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-01t9-0190000000-6b136607b48b31667801	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-01q9-4790000000-5046458d5d3e3c228518	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-05mo-8930000000-852d50a19eb0b0df729b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-0090000000-ab643cae783eb66bf131	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0059-1090000000-abce276de392be9d7d3f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-9230000000-40a41feed498373e54d2	Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-00nf-9200000000-cf911df79059a750cb2a	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum

Biological Properties

Cellular Locations

Not Available

Biofluid Locations and Tissue Locations

Follicular Fluid
Milk
Oocyte
Oocyte (zona-intact oocytes)

Concentrations

Biofluid	Status	Value	Condition	Species	Reference	Details
Follicular Fluid	Detected but not Quantified	Not Applicable	Not Available	Porcine	Warzych, E., Cies...	details
Milk	Detected but not Quantified	Not Applicable	Not Available	Bovine	20855010	details
Milk	Detected but not Quantified	Not Applicable	Not Available	Bovine	11913692	details
Oocyte	Detected but not Quantified	Not Applicable	Not Available	Ovine	10793638	details
Oocyte (zona-intact oocytes)	Detected but not Quantified	Not Applicable	Not Available	Bovine	10793638	details
Oocyte (zona-intact oocytes)	Detected but not Quantified	Not Applicable	Not Available	Porcine	10793638	details