Structure Database (LMSD)

Common Name
gamma-linolenoyl-EA
Systematic Name
N-(6Z,9Z,12Z-octadecatrienoyl)-ethanolamine
Synonyms
  • N-cis-6,9,12-octadecatrienoylethanolamine
  • gamma-linolenoyl ethanolamide
LM ID
LMFA08040003
Formula
C20H35NO2
Exact Mass
Calculate m/z
321.266779
Sum Composition
NAE 18:3
Status
Curated
Show lipids differing only in stereochemistry/bond geometry

Classification

Category
Main Class
Sub Class
Fatty Acyls [FA]
Fatty amides [FA08]
N-acyl ethanolamines (endocannabinoids) [FA0804]
Fatty Acids and Conjugates [FA01]
Unsaturated fatty acids [FA0103]

Biological Context

γ-Linolenoyl ethanolamide is a member of the family of fatty N-acyl ethanolamines collectively called endocannabinoids.1,2,3,4 The relative importance of this ethanolamine metabolite has yet to be determined.

This information has been provided by Cayman Chemical

References

1. Buczynski, M.W., Svensson, C.I., Dumlao, D.S., et al. Inflammatory hyperalgesia induces essential bioactive lipid production in the spinal cord. J. Neurochem. 114(4), 981-993 (2010).
2. Saghatelian, A., Trauger, S.A., Want, E.J., et al. Assignment of endogenous substrates to enzymes by global metabolite profiling. Biochemistry 43(45), 14332-14339 (2004).
3. Doetsch, P.W., Zastawny, T.H., Martin, A.M., et al. Monomeric base damage products from adenine, guanine, and thymine induced by exposure of DNA to ultraviolet radiation. Biochemistry 34(3), 737-742 (1995).
4. Bachur, N.R., and Udenfriend, S. Microsomal synthesis of fatty acid amides. J. Biol. Chem. 241(6), 1308-1313 (1966).

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
synthetic construct (#32630)
Structural requirements for binding of anandamide-type compounds to the brain cannabinoid receptor.,
J Med Chem, 1997
Pubmed ID: 9057852

String Representations

InChiKey (Click to copy)
KRDUNUMTOBLEPM-QNEBEIHSSA-N
InChi (Click to copy)
InChI=1S/C20H35NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-20(23)21-18-19-22/h6-7,9-10,12-13,22H,2-5,8,11,14-19H2,1H3,(H,21,23)/b7-6-,10-9-,13-12-
SMILES (Click to copy)
C(/C/C=C\C/C=C\CCCCC)=C/CCCCC(=O)NCCO

Other Databases

CHEBI ID
165585
LIPIDBANK ID
XPR7003
PubChem CID
5283445
SwissLipids ID
SLM:000598160
Cayman ID
9001747

Calculated Physicochemical Properties

Heavy Atoms 23
Rings 0
Aromatic Rings 0
Rotatable Bonds 15
Van der Waals Molecular Volume 372.58
Topological Polar Surface Area 49.33
Hydrogen Bond Donors 2
Hydrogen Bond Acceptors 3
logP 5.25
Molar Refractivity 100.34

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Created at
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Updated at
7th Feb 2024