Metabolomics Structure Database

MDLMOL SDF CSV TSV

MW REGNO:	573
Common Name:	gamma-Linolenic acid
Systematic Name:	6Z,9Z,12Z-octadecatrienoic acid
RefMet Name:	gamma-Linolenic acid
Synonyms:	cis-6, cis-9, cis-12-octadecatrienoic acid; C18:3n-6,9,12 [PubChem Synonyms]
Exact Mass:	278.2246 (neutral)    Calculate m/z: (Choose adduct) [M+H]+ [M+H-H2O]+ [M.]+ [M+2H]2+ [M+3H]3+ [M+4H]4+ [M+K]+ [M+2K]2+ [M-H+2K]+ [M+Na]+ [M+2Na]2+ [M-H+2Na]+ [M+Li]+ [M+2Li]2+ [M+NH4]+ [M-H]- [M-2H]2- [M-3H]3- [M-4H]4- [M+Cl]- [M+OAc]- [M+HCOO]- M(neutral)
Formula:	C18H30O2
InChIKey:	VZCCETWTMQHEPK-QNEBEIHSSA-N
LIPID MAPS Category:	Fatty Acyls [FA]
LIPID MAPS mainclass:	Fatty Acids and Conjugates [FA01]
LIPID MAPS subclass:	Unsaturated fatty acids [FA0103]
Massbank MS spectra:	View MS spectra
SMILES:	CCCCC/C=CC/C=CC/C=CCCCCC(=O)O
Studies:	Available studies (via RefMet name)

Select appropriate tab below to view additional details:

All Database Links Calculated Properties Human Pathways

External database links:

PubChem CID:	5280933
LIPID MAPS ID:	LMFA01030141
CHEBI ID:	28661
HMDB ID:	HMDB0003073
KEGG ID:	C06426
Chemspider ID:	4444436
METLIN ID:	386
MetaCyc ID:	CPD-8117
Plant Metabolite Hub(Pmhub):	MS000006107

Calculated physicochemical properties (?):

Heavy Atoms:	20
Rings:	0
Aromatic Rings:	0
Rotatable Bonds:	13
van der Waals Molecular volume:	326.98 Å3 molecule-1
Toplogical Polar Sufrace Area:	37.30 Å2 molecule-1
Hydrogen Bond Donors:	1
Hydrogen Bond Acceptors:	2
logP:	5.66
Molar Refractivity:	86.90
Fraction sp3 Carbons:	0.61
sp3 Carbons:	11

Human Pathway links:

HMDB and KEGG pathways containing this metabolite

REACTOME pathways containing this metabolite

References

LIPID MAPS classification: "Update of the LIPID MAPS comprehensive classification system for lipids", Fahy E, Subramaniam S, Murphy RC, Nishijima M, Raetz CR, Shimizu T, Spener F, van Meer G, Wakelam MJ, and Dennis EA, J. Lipid Res. (2009) 50: S9-S14. DOI: 10.1194/jlr.R800095-JLR200
ClassyFire classification: "ClassyFire: automated chemical classification with a comprehensive, computable taxonomy", Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS, J. Cheminformatics (2016) 8:61. DOI: 10.1186/s13321-016-0174-y