Structure Database (LMSD)

Common Name
Nervonoyl-EA
Systematic Name
N-(15Z-tetracosenoyl)-ethanolamine
Synonyms
  • Nervonoyl-ethanolamine
  • cis-selacholeoyl-ethanolamine
LM ID
LMFA08040055
Formula
C26H51NO2
Exact Mass
Calculate m/z
409.391979
Sum Composition
NAE 24:1
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]
Fatty Acids and Conjugates [FA01]
Unsaturated fatty acids [FA0103]

Biological Context

Nervonoyl ethanolamide is a member of the family of fatty N-acyl ethanolamines collectively called endocannabinoids.1,2,3,4 The relative importance of this ethanolamine metabolite has not been determined.

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. 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)
LISKWSFNVJTQKH-KTKRTIGZSA-N
InChi (Click to copy)
InChI=1S/C26H51NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22-23-26(29)27-24-25-28/h9-10,28H,2-8,11-25H2,1H3,(H,27,29)/b10-9-
SMILES (Click to copy)
C(CCCCCCCCCCC(=O)NCCO)CC/C=C\CCCCCCCC

Other Databases

CHEBI ID
146187
PubChem CID
24762162
SwissLipids ID
SLM:000598182
Cayman ID
9001746

Calculated Physicochemical Properties

Heavy Atoms 29
Rings 0
Aromatic Rings 0
Rotatable Bonds 23
Van der Waals Molecular Volume 481.66
Topological Polar Surface Area 49.33
Hydrogen Bond Donors 2
Hydrogen Bond Acceptors 3
logP 8.04
Molar Refractivity 128.23

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Updated at
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