LIPID MAPS

Structure Database (LMSD)

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Common Name

N-oleoyl leucine

Systematic Name

N-(9Z-octadecenoyl)-leucine

Synonyms

LM ID

LMFA08020116

Formula

C₂₄H₄₅NO₃

Exact Mass

Calculate m/z

395.339944

Sum Composition

NALeu 18:1

Status

Curated

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Classification

Biological Context

N-Oleoyl leucine is an N-acyl amide generated by PM20D1 that uncouples mitochondrial respiration independent of uncoupling protein 1 (UCP1) in vitro.{31656} N-Oleoyl leucine (25 mg/kg, i.p.) decreases body weight and food intake, preferentially decreasing fat mass in a diet-induced obesity mouse model. It improves glucose homeostasis in a fasting glucose tolerance test and increases VO2 while slightly decreasing overall locomotor activity.

This information has been provided by Cayman Chemical

References

1. Long, J.Z., Svensson, K.J., Bateman, L.A., et al. The secreted enzyme PM20D1 regulates lipidated amino acid uncouplers of mitochondria. Cell 166(2), 1-12 (2016).

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)

UMOAAMQGRRCHPA-GJCOWUBNSA-N

InChi (Click to copy)

InChI=1S/C24H45NO3/c1-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-23(26)25-22(24(27)28)20-21(2)3/h11-12,21-22H,4-10,13-20H2,1-3H3,(H,25,26)(H,27,28)/b12-11-/t22-/m0/s1

SMILES (Click to copy)

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