Structure Database (LMSD)

Common Name
Palmitamide
Systematic Name
Hexadecanamide
Synonyms
LM ID
LMFA08010009
Formula
C16H33NO
Exact Mass
Calculate m/z
255.256214
Status
Curated
Show lipids differing only in stereochemistry/bond geometry
View MassBank spectra
View NP-MRD ID(NMR) spectrum
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]
Primary amides [FA0801]

Biological Context

Hexadecanamide is a primary fatty acid amide that is derived from palmitic acid (C16:0) and belongs to a class of important cell signaling lipids.1 While the physiological significance of this compound is not yet clear, it is reported to demonstrate weak anticonvulsant activity in a maximal electroshock seizure test in mice when compared with the endocannabinoid palmitoyl ethanolamide .2

This information has been provided by Cayman Chemical

References

1. Farrell, E.K., Chen, Y., Barazanji, M., et al. Primary fatty acid amide metabolism: Conversion of fatty acids and an ethanolamine in N18TG2 and SCP cells. J. Lipid. Res. 53(2), 247-256 (2012).
2. Lambert, D.M., Vandevoorde, S., Diepandaele, G., et al. Anticonvulsant activity of N-palmitoylethanolamide, a putative endocannabinoid, in mice. Epilepsia 42(3), 321-327 (2001).

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
Mus musculus (#10090)
Mammalia (#40674)
Primary fatty acid amide metabolism: conversion of fatty acids and an ethanolamine in N18TG2 and SCP cells.,
J Lipid Res, 2012
Pubmed ID: 22095832

String Representations

InChiKey (Click to copy)
HSEMFIZWXHQJAE-UHFFFAOYSA-N
InChi (Click to copy)
InChI=1S/C16H33NO/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16(17)18/h2-15H2,1H3,(H2,17,18)
SMILES (Click to copy)
NC(=O)CCCCCCCCCCCCCCC

Other Databases

HMDB ID
HMDB0012273
CHEBI ID
74475
PubChem CID
69421
Cayman ID
21086

Calculated Physicochemical Properties

Heavy Atoms 18
Rings 0
Aromatic Rings 0
Rotatable Bonds 14
Van der Waals Molecular Volume 302.51
Topological Polar Surface Area 43.09
Hydrogen Bond Donors 1
Hydrogen Bond Acceptors 1
logP 4.95
Molar Refractivity 79.51

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Updated at
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