Structure Database (LMSD)

Common Name
Eicosanoyl-EA
Systematic Name
N-eicosanoyl-ethanolamine
Synonyms
  • N-eicosanoylethanolamine
  • Arachidoyl Ethanolamide
  • Arachidoyl-EA
LM ID
LMFA08040038
Formula
C22H45NO2
Exact Mass
Calculate m/z
355.345029
Sum Composition
NAE 20:0
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]

Biological Context

Arachidoyl ethanolamide is one of the saturated fatty acyl ethanolamides devoid of classical (CB1/CB2) activity. Arachidoyl ethanolamide does not bind to the murine CB1 receptor and does not compete with anandamide as a substrate for the endocannabinoid hydrolytic enzyme fatty acid amide hydrolase.1,2 Non-CB receptor-mediated pharmacology of the saturated ethanolamides is still being elucidated.3

This information has been provided by Cayman Chemical

References

1. 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).
2. Sheskin, T., Hanus, L., Slager, J., et al. Structural requirements for binding of anandamide-type compounds to the brain cannabinoid receptor. J. Med. Chem. 40(5), 659-667 (1997).
3. Desarnaud, F., Cadas, H., and Piomelli, D. Anandamide amidohydrolase activity in rat brain microsomes. Identification and partial characterization. J. Biol. Chem. 270(11), 6030-6035 (1995).

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)
AUJVQJHODMISJP-UHFFFAOYSA-N
InChi (Click to copy)
InChI=1S/C22H45NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-22(25)23-20-21-24/h24H,2-21H2,1H3,(H,23,25)
SMILES (Click to copy)
C(CCCCCCCCCCC)CCCCCCCC(=O)NCCO

Other Databases

CHEBI ID
85253
PubChem CID
3787294
SwissLipids ID
SLM:000390116
Cayman ID
10005765
PDB ID
A9M

Calculated Physicochemical Properties

Heavy Atoms 25
Rings 0
Aromatic Rings 0
Rotatable Bonds 20
Van der Waals Molecular Volume 415.10
Topological Polar Surface Area 49.33
Hydrogen Bond Donors 2
Hydrogen Bond Acceptors 3
logP 6.71
Molar Refractivity 109.86

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Created at
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Updated at
7th Feb 2024