Structure Database (LMSD)

Common Name
Behenoyl-EA
Systematic Name
N-(Docosanoyl)-ethanolamine
Synonyms
  • Behenoyl-ethanolamine
LM ID
LMFA08040052
Formula
C24H49NO2
Exact Mass
Calculate m/z
383.376329
Sum Composition
NAE 22:0
Status
Curated
Show lipids differing only in stereochemistry/bond geometry

Classification

Category
Main Class
Sub Class
Fatty Acyls [FA]
Fatty amides [FA08]
N-acyl ethanolamines (endocannabinoids) [FA0804]

Biological Context

Docosanoyl ethanolamide is a saturated N-acylethanolamide. Non-cannabinoid receptor-mediated pharmacology of the saturated ethanolamides is still being elucidated.1 Other studies indicate they may have a role in the functioning of ion channels.2

This information has been provided by Cayman Chemical

References

1. Oz, M., Alptekin, A., Tchugunova, Y., et al. Effects of saturated long-chain N-acylethanolamines on voltage-dependent Ca2+ fluxes in rabbit T-tubule membranes. Arch. Biochem. Biophys. 434(2), 344-351 (2005).
2. Smart, D., Jonsson, K.O., Vandevoorde, S., et al. “Entourage” effects of N-acyl ethanolamines at human vanilloid receptors. Comparison of effects upon anandamide-induced vanilloid receptor activation and upon anandamide metabolism. Br. J. Pharmacol. 136, 452-458 (2002).

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
Rattus norvegicus (#10116)
Mammalia (#40674)
Inflammatory hyperalgesia induces essential bioactive lipid production in the spinal cord.,
J Neurochem, 2010
Pubmed ID: 20492349

String Representations

InChiKey (Click to copy)
XHFWUECSNJWBJU-UHFFFAOYSA-N
InChi (Click to copy)
InChI=1S/C24H49NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-24(27)25-22-23-26/h26H,2-23H2,1H3,(H,25,27)
SMILES (Click to copy)
C(CCCCCCCCCCCCC(=O)NCCO)CCCCCCCC

Other Databases

CHEBI ID
146186
PubChem CID
3023585
SwissLipids ID
SLM:000598132
Cayman ID
10005823

Calculated Physicochemical Properties

Heavy Atoms 27
Rings 0
Aromatic Rings 0
Rotatable Bonds 22
Van der Waals Molecular Volume 449.70
Topological Polar Surface Area 49.33
Hydrogen Bond Donors 2
Hydrogen Bond Acceptors 3
logP 7.49
Molar Refractivity 119.09

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Updated at
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