Structure Database (LMSD)

Common Name
Alpha-linolenoyl-EA
Systematic Name
N-(9Z,12Z,15Z-octadecatrienoyl)-ethanolamine
Synonyms
  • N-cis-9,12,15-Octadecatrienoylethanolamine
  • alpha-Linolenoyl ethanolamide
LM ID
LMFA08040007
Formula
C20H35NO2
Exact Mass
Calculate m/z
321.266779
Sum Composition
NAE 18:3
Status
Curated
Show lipids differing only in stereochemistry/bond geometry
View MassBank spectra
View NP-MRD ID(NMR) spectrum

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

α-Linolenoyl ethanolamide is an endocannabinoid containing α-linolenic acid in place of the arachidonate moiety of AEA. α-Linolenoyl ethanolamide has been detected in porcine brain, but its specific role and relative importance as a cannabinergic neurotransmitter have not been elucidated.1

This information has been provided by Cayman Chemical

References

1. Hanus, L., Gopher, A., Almog, S., et al. Two new unsaturated fatty acid ethanolamides in brain that bind to the cannabinoid receptor. J. Med. Chem. 36(20), 3032-3034 (1993).

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
Sus scrofa (#9823)
Mammalia (#40674)
Two new unsaturated fatty acid ethanolamides in brain that bind to the cannabinoid receptor.,
J Med Chem, 1993
Pubmed ID: 8411021

String Representations

InChiKey (Click to copy)
HBJXRRXWHSHZPU-PDBXOOCHSA-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/h3-4,6-7,9-10,22H,2,5,8,11-19H2,1H3,(H,21,23)/b4-3-,7-6-,10-9-
SMILES (Click to copy)
C(C/C=C\C/C=C\C/C=C\CC)CCCCCC(=O)NCCO

Other Databases

HMDB ID
HMDB0013624
CHEBI ID
89605
LIPIDBANK ID
XPR7007
PubChem CID
5283449
SwissLipids ID
SLM:000598137
Cayman ID
90215

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