Structure Database (LMSD)

Common Name
Pentadecanoyl-EA
Systematic Name
N-(Pentadecanoyl)-ethanolamine
Synonyms
  • Pentadecanoyl-ethanolamine
LM ID
LMFA08040045
Formula
C17H35NO2
Exact Mass
Calculate m/z
285.266779
Sum Composition
NAE 15:0
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

Pentadecanoyl ethanolamide is a member of the family of fatty N-acyl ethanolamines collectively called endocannabinoids.1,2,3,4,5 The specific role and relative importance of this ethanolamine metabolite have 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. Mulder, A.M., and Cravatt, B.F. Endocannabinoid metabolism in the absence of fatty acid amide hydrolase (FAAH): Discovery of phosphorylcholine derivatives of N-acyl ethanolamines. Biochemistry 45(38), 11267-11277 (2006).
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)
UHPXXKLAACDXGS-UHFFFAOYSA-N
InChi (Click to copy)
InChI=1S/C17H35NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-17(20)18-15-16-19/h19H,2-16H2,1H3,(H,18,20)
SMILES (Click to copy)
C(CCCCCCCCCCCCC)C(=O)NCCO

Other Databases

CHEBI ID
165589
PubChem CID
14455157
SwissLipids ID
SLM:000598190
Cayman ID
9001740

Calculated Physicochemical Properties

Heavy Atoms 20
Rings 0
Aromatic Rings 0
Rotatable Bonds 15
Van der Waals Molecular Volume 328.60
Topological Polar Surface Area 49.33
Hydrogen Bond Donors 2
Hydrogen Bond Acceptors 3
logP 4.76
Molar Refractivity 86.77

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Updated at
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