Structure Database (LMSD)

Common Name
Palmitoleoyl-EA
Systematic Name
N-(9Z-hexadecenoyl)-ethanolamine
Synonyms
  • Palmitoleoyl ethanolamide
  • POEA
LM ID
LMFA08040043
Formula
C18H35NO2
Exact Mass
Calculate m/z
297.266779
Sum Composition
NAE 16:1
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

N-acylethanolamines (NAEs) are lipid-derived signaling compounds. For example, arachidonoyl ethanolamide is an endogenous cannabinoid (CB) that activates the CB1 and CB2 receptors. Palmitoleoyl Ethanolamide (POEA) is an NAE that is produced endogenously from palmitoleic acid.1 Unlike arachidonoyl ethanolamide and palmitoyl ethanolamide, POEA does not have antinociceptive effects, as assessed in the formalin-evoked pain model.2

This information has been provided by Cayman Chemical

References

1. Lucanic, M., Held, J.M., Vantipalli, M.C., et al. N-acylethanolamine signalling mediates the effect of diet on lifespan in Caenorhabditis elegans. Nature 473(7346), 226-229 (2011).
2. Calignano, A., LaRana, G., and Piomelli, D. Antinociceptive activity of the endogenous fatty acid amide, palmitylethanolamide. Eur. J. Pharmacol. 419(2-3), 191-198 (2001).

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
Caenorhabditis elegans (#6239)
Chromadorea (#119089)
N-acylethanolamine signalling mediates the effect of diet on lifespan in Caenorhabditis elegans.,
Nature, 2011
Pubmed ID: 21562563

String Representations

InChiKey (Click to copy)
WFRLANWAASSSFV-FPLPWBNLSA-N
InChi (Click to copy)
InChI=1S/C18H35NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-18(21)19-16-17-20/h7-8,20H,2-6,9-17H2,1H3,(H,19,21)/b8-7-
SMILES (Click to copy)
C(CCCCCCC(=O)NCCO)/C=C\CCCCCC

Other Databases

HMDB ID
HMDB0013648
CHEBI ID
71465
PubChem CID
9835868
SwissLipids ID
SLM:000000410
Cayman ID
10965

Calculated Physicochemical Properties

Heavy Atoms 21
Rings 0
Aromatic Rings 0
Rotatable Bonds 15
Van der Waals Molecular Volume 343.26
Topological Polar Surface Area 49.33
Hydrogen Bond Donors 2
Hydrogen Bond Acceptors 3
logP 4.92
Molar Refractivity 91.29

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Created at
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Updated at
7th Feb 2024