Structure Database (LMSD)

OH O N H
Common Name
Oleoyl-EA
Systematic Name
N-(9Z-octadecenoyl)-ethanolamine
Synonyms
  • oleoyl ethanolamide
  • N-(cis-9-octadecenoyl) ethanolamine
  • N-(hydroxyethyl) oleamide
  • OEA
  • oleoylethanolamine
LM ID
LMFA08040015
Formula
C20H39NO2
Exact Mass
Calculate m/z
325.298079
Sum Composition
NAE 18:1
Status
Active
Show lipids differing only in stereochemistry/bond geometry

Main

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]

String Representations

InChiKey (Click to copy)
BOWVQLFMWHZBEF-KTKRTIGZSA-N
InChi (Click to copy)
InChI=1S/C20H39NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-20(23)21-18-19-22/h9-10,22H,2-8,11-19H2,1H3,(H,21,23)/b10-9-
SMILES (Click to copy)
C(CCCCCCC/C=C\CCCCCCCC)(=O)NCCO

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
Rattus norvegicus (#10116)
Mammalia (#40674)
An anorexic lipid mediator regulated by feeding.,
Nature, 2001
Pubmed ID: 11700558
Theobroma cacao (#3641)
Magnoliopsida (#3398)
Brain cannabinoids in chocolate.,
Nature, 1996
Pubmed ID: 8751435

Other Databases

Wikipedia
Oleoylethanolamide
HMDB ID
HMDB0002088
CHEBI ID
71466
PubChem CID
5283454
SwissLipids ID
SLM:000000147
Cayman ID
90265
PDB ID
5YM
GuidePharm ID
2661

Calculated Physicochemical Properties

Heavy Atoms 23
Rings 0
Aromatic Rings 0
Rotatable Bonds 17
Van der Waals Molecular Volume 377.86
Topological Polar Surface Area 49.33
Hydrogen Bond Donors 2
Hydrogen Bond Acceptors 3
logP 5.70
Molar Refractivity 100.53

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Created at
-
Updated at
7th Feb 2024