LIPID MAPS

Structure Database (LMSD)

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Common Name

N-arachidonoyl glycine

Systematic Name

N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-glycine

Synonyms

N-arachidonoylglycine

LM ID

LMFA08020003

Formula

C₂₂H₃₅NO₃

Exact Mass

Calculate m/z

361.261694

Sum Composition

NAGly 20:4

Status

Curated

Show lipids differing only in stereochemistry/bond geometry

View NP-MRD ID(NMR) spectrum

Classification

Biological Context

Arachidonoyl glycine (N-arachidonyl glycine; NAGly) has been isolated from cell cultures treated with arachidonoyl ethanolamide (AEA; anandamide),1 from extracts of mammalian brain,2,3 and has also been synthesized as an analog of AEA for structure/activity testing.⁴ NAGly may be produced endogenously via oxidation of AEA, or by transacylation of arachidonoyl CoA. NAGly is reported to have analgesic activities in whole animal experiments.^1,2,3 Since it seems to be a very poor ligand for the CB1 receptor,4 these effects are probably mediated via other signaling pathways.

This information has been provided by Cayman Chemical

References

1. Burstein, S.H., Rossetti, R.G., Yagen, B., et al. Oxidative metabolism of anandamide. Prostaglandins Other Lipid Mediat. 61(1-2), 29-41 (2000).

2. Huang, S.M., Bisogno, T., Petros, T.J., et al. Identification and characterization of an endogenous anandamide-like compound: N-Arachidonylglycine (NAGly). ICRS 2001 Symposium on the Cannabinoids 78 (2001).

3. Sheskin, T., Hanus, L., Slager, J., et al. Structural requirements for binding of anandamide-type compounds to the brain cannabinoid receptor. J. Med. Chem. 40(5), 659-667 (1997).

4. Huang, S.M., Bisogno, T., Petros, T.J., et al. Identification of a new class of molecules, the arachidonyl amino acids, and characterization of one member that inhibits pain. The Journal of Biological Chemisty 276(46), 42639-42644 (2001).

References

Taxonomy Information

Curated from

NCBI taxonomy class

Reference

Rattus norvegicus (#10116)

Mammalia (#40674)

The endocannabinoid anandamide is a precursor for the signaling lipid N-arachidonoyl glycine by two distinct pathways.,
BMC Biochem, 2009

Pubmed ID: 19460156

synthetic construct (#32630)

Structural requirements for binding of anandamide-type compounds to the brain cannabinoid receptor.,
J Med Chem, 1997

Pubmed ID: 9057852

String Representations

InChiKey (Click to copy)

YLEARPUNMCCKMP-DOFZRALJSA-N

InChi (Click to copy)

InChI=1S/C22H35NO3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-21(24)23-20-22(25)26/h6-7,9-10,12-13,15-16H,2-5,8,11,14,17-20H2,1H3,(H,23,24)(H,25,26)/b7-6-,10-9-,13-12-,16-15-

SMILES (Click to copy)

C(/C/C=C\C/C=C\CCCCC)=C/C/C=C\CCCC(=O)NCC(=O)O