Structure Database (LMSD)

Common Name
Erucicoyl-EA
Systematic Name
N-(13Z-docosanoyl)-ethanolamine
Synonyms
  • Erucicoyl-ethanolamine
LM ID
LMFA08040050
Formula
C24H47NO2
Exact Mass
Calculate m/z
381.36068
Sum Composition
NAE 22:1
Status
Curated
Show lipids differing only in stereochemistry/bond geometry
View studies deposited in Metabolomics Workbench in which this molecule has been identified

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

Docosaenoyl ethanolamide is a member of the family of fatty N-acyl ethanolamines collectively called endocannabinoids.1,2,3 This long-chain ethanolamine has been detected at relatively high levels in rat cerebrospinal fluid and has been used to examine the function of voltage-dependent Ca2+ channels in skeletal muscle membranes.4,5

This information has been provided by Cayman Chemical

References

1. Bachur, N.R., and Udenfriend, S. Microsomal synthesis of fatty acid amides. The Journal of Biological Chemisty 241(6), 1308-1313 (1966).
2. Doetsch, P.W., Zastawny, T.H., Martin, A.M., et al. Monomeric base damage products from adenine, guanine, and thymine induced by exposure of DNA to ultraviolet radiation. Biochemistry 34(3), 737-742 (1995).
3. Saghatelian, A., Trauger, S.A., Want, E.J., et al. Assignment of endogenous substrates to enzymes by global metabolite profiling. Biochemistry 43(45), 14332-14339 (2004).
4. 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).
5. Buczynski, M.W., Svensson, C.I., Dumlao, D.S., et al. Inflammatory hyperalgesia induces essential bioactive lipid production in the spinal cord. J. Neurochem. 114(4), 981-993 (2010).

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)
UGYSMGXRWBTMRZ-KTKRTIGZSA-N
InChi (Click to copy)
InChI=1S/C24H47NO2/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/h9-10,26H,2-8,11-23H2,1H3,(H,25,27)/b10-9-
SMILES (Click to copy)
C(=C/CCCCCCCCCCCC(=O)NCCO)/CCCCCCCC

Other Databases

CHEBI ID
165584
PubChem CID
6436482
SwissLipids ID
SLM:000598181
Cayman ID
9001745

Calculated Physicochemical Properties

Heavy Atoms 27
Rings 0
Aromatic Rings 0
Rotatable Bonds 21
Van der Waals Molecular Volume 447.06
Topological Polar Surface Area 49.33
Hydrogen Bond Donors 2
Hydrogen Bond Acceptors 3
logP 7.26
Molar Refractivity 119.00

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Updated at
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