LIPID MAPS

Structure Database (LMSD)

View 3D

Download as... MDLMOL SDF CSV TSV PNG

Common Name

N-oleoyl alanine

Systematic Name

N-(9Z-octadecenoyl)-alanine

Synonyms

LM ID

LMFA08020124

Formula

C₂₁H₃₉NO₃

Exact Mass

Calculate m/z

353.292994

Sum Composition

NAAla 18:1

Status

Curated

Show lipids differing only in stereochemistry/bond geometry

Classification

Biological Context

N-Oleoyl alanine is a natural N-acyl amide that has been detected in insect and animal tissues.^1,2 Several N-acyl amides are bioactive mediators that modulate G protein-coupled receptors or transient receptor potential channels, although the activity of N-oleoyl alanine has not been delineated.^1,2

This information has been provided by Cayman Chemical

References

1. Tan, B., O'Dell, D.K., Yu, Y.W., et al. Identification of endogenous acyl amino acids based on a targeted lipidomics approach. J. Lipid. Res. 51(1), 112-119 (2010).

2. Tortoriello, G., Rhodes, B.P., Takacs, S.M., et al. Targeted lipidomics in Drosophila melanogaster identifies novel 2-monoacylglycerols and N-acyl amides. PLoS One 8(7), e67865 (2013).

References

Taxonomy Information

Curated from

NCBI taxonomy class

Reference

Rattus norvegicus (#10116)

Mammalia (#40674)

Identification of endogenous acyl amino acids based on a targeted lipidomics approach.,
J Lipid Res, 2010

Pubmed ID: 19584404

DOI: 10.1194/jlr.M900198-JLR200

String Representations

InChiKey (Click to copy)

CHQZBIVWDKADIA-GDWUOILNSA-N

InChi (Click to copy)

InChI=1S/C21H39NO3/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-20(23)22-19(2)21(24)25/h10-11,19H,3-9,12-18H2,1-2H3,(H,22,23)(H,24,25)/b11-10-/t19-/m0/s1

SMILES (Click to copy)

C[C@]([H])(NC(CCCCCCC/C=C\CCCCCCCC)=O)C(=O)O