Structure Database (LMSD)

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
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

Oleoyl ethanolamide (OEA) is an analog of the endocannabinoid AEA found in brain tissue and in chocolate.1 It is one of the long chain fatty acid ethanolamides that accumulates rapidly in infarcted tissue,2 but its biosynthesis is reduced in the intestine of rats following food deprivation.3 OEA is an endogenous, potent agonist for PPARα, exhibiting an EC50 value of 120 nM in a transactivation assay.4 Systemic administration of OEA suppresses food intake and reduces weight gain in rats (10 mg/kg intraperitoneally) and PPARα wild-type mice, but not in PPARα knockout mice.3,4 These data indicate that OEA regulates food intake by a PPARα-mediated mechanism.

This information has been provided by Cayman Chemical

References

1. Fu, J., Gaetani, S., Oveisi, F., et al. Oleylethanolamide regulates feeding and body weight through activation of the nuclear receptor PPAR-α. Nature 425(6953), 90-93 (2003).
2. de Fonseca, F.R., Navarro, M., Gómez, R., et al. An anorexic lipid mediator regulated by feeding. Nature 414(6860), 209-212 (2001).
3. di Tomaso, E., Beltramo, M., and Piomelli, D. Brain cannabinoids in chocolate. Nature 382(6593), 677-678 (1996).
4. Epps, D.E., Palmer, J.W., Schmid, H.H.O., et al. Inhibition of permeability-dependent Ca2+ release from mitochondria by N-acelethanolamines, a class of lipids synthesized in ischemic heart tissue. J. Biol. Chem. 257(3), 1383-1392 (1982).

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

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

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

Admin

Created at
-
Updated at
7th Feb 2024