Structure Database (LMSD)

Common Name
Myristoyl-EA
Systematic Name
N-(Tetradecanoyl)-ethanolamine
Synonyms
  • Myristoyl-ethanolamine
LM ID
LMFA08040042
Formula
C16H33NO2
Exact Mass
Calculate m/z
271.251129
Sum Composition
NAE 14:0
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

Myristoyl ethanolamide is a member of the family of fatty N-acyl ethanolamines collectively called endocannabinoids.1,2,3 Myristic acid is typically detected at low levels in rat cerebrospinal fluid, however the specific role and relative importance of its ethanolamine metabolite have not been yet determined.4

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)
JHIXEZNTXMFXEK-UHFFFAOYSA-N
InChi (Click to copy)
InChI=1S/C16H33NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-16(19)17-14-15-18/h18H,2-15H2,1H3,(H,17,19)
SMILES (Click to copy)
C(CCCCCCCCCCCC)C(=O)NCCO

Other Databases

CHEBI ID
85262
PubChem CID
8890
SwissLipids ID
SLM:000390180
Cayman ID
9001742
GuidePharm ID
5221

Calculated Physicochemical Properties

Heavy Atoms 19
Rings 0
Aromatic Rings 0
Rotatable Bonds 14
Van der Waals Molecular Volume 311.30
Topological Polar Surface Area 49.33
Hydrogen Bond Donors 2
Hydrogen Bond Acceptors 3
logP 4.37
Molar Refractivity 82.15

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Updated at
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