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Structure Database (LMSD)

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Common Name

N-oleoyl glutamine

Systematic Name

N-(9Z-octadecenoyl)-glutamine

Synonyms

LM ID

LMFA08020128

Formula

C₂₃H₄₂N₂O₄

Exact Mass

Calculate m/z

410.314458

Sum Composition

NAGln 18:1

Status

Curated

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Classification

Biological Context

N-Oleoyl glutamine is an endogenous N-acyl amine.^1,2 It is both formed and degraded by peptidase M20 domain-containing 1 (PM20D1), a factor secreted by thermogenic adipose cells. N-Oleoyl glutamine (50 µM) induces mitochondrial uncoupling to increase respiration in C2C12 cells by 64%.³ It inhibits capsaicin-induced calcium flux in HEK293A cells co-transfected with transient receptor potential vanilloid 1 (TRPV1) and red fluorescent protein (RFP).² N-Oleoyl glutamine (100 mg/kg) reduces the number of acetic acid-induced abdominal constrictions, as well as formalin-induced paw licking in mice.

This information has been provided by Cayman Chemical

References

1. Lin, H., Long, J.Z., Roche, A.M., et al. Discovery of hydrolysis-resistant isoindoline N-acyl amino acid analogues that stimulate mitochondrial respiration. J. Med. Chem. 61(7), 3224-3230 (2018).

2. Long, J.Z., Roche, A.M., Berdan, C.A., et al. Ablation of PM20D1 reveals N-acyl amino acid control of metabolism and nociception. Proc. Natl. Acad. Sci. USA 115(29), E6937-E6945 (2018).

3. 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)

ZHVSXWCIYWYBQP-QJRAZLAKSA-N

InChi (Click to copy)

InChI=1S/C23H42N2O4/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-22(27)25-20(23(28)29)18-19-21(24)26/h9-10,20H,2-8,11-19H2,1H3,(H2,24,26)(H,25,27)(H,28,29)/b10-9-/t20-/m0/s1

SMILES (Click to copy)

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