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

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]

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
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
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)
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