Structure Database (LMSD)

Common Name
N-oleoyl glycine
Systematic Name
N-(9Z-octadecenoyl)-glycine
Synonyms
  • EMA-1
  • Elmiric acid
LM ID
LMFA08020082
Formula
Exact Mass
Calculate m/z
339.277344
Sum Composition
Status
Curated


Classification

Biological Context

N-Oleoyl glycine is an endogenous lipoamino acid.1,2 It increases triglyceride levels in 3T3-L1 adipocytes, an effect that can be reversed by SR141716 (rimonabant), and selectively induces the expression of mRNA encoding the cannabinoid 1 (CB1) receptor over mRNA encoding the CB2 receptor in the same cells when used at a concentration of 50 µM.2 N-Oleoyl glycine (1 µM) potentiates glycine-induced chloride currents in Xenopus oocytes expressing α1-, α1β-, α2-, α2β-, or α3 subunit-containing glycine receptors but not those expressing α3β subunit-containing glycine receptors.3 It increases c-Fos protein levels, intracellular calcium levels, and Agouti-related protein (AgRP) secretion in mHypoE-38 hypothalamic cells, effects that can be reversed by AM251 .4 N-Oleoyl glycine (60 mg/kg) reduces binge-like ethanol intake in alcohol-preferring mice without affecting total fluid intake and does not affect sucrose intake in the sucrose preference test in mice.5 It reduces balance impairments, thermal hyperalgesia, mechanical allodynia, aggressiveness, and immobility time in the tail suspension test, indicating antidepressant-like activity, in a mouse model of traumatic brain injury when administered at a dose of 50 mg/kg.6

This information has been provided by Cayman Chemical

References

1. Bradshaw, H.B., Rimmerman, N., Hu, S.S.-J., et al. Chapter 8 Novel endogenous N-acyl glycines: Identification and characterization. Vitam. Horm. 81, 191-205 (2009).
4. Wu, J., Zhu, C., Yang, L., et al. N-oleoylglycine-induced hyperphagia is associated with the activation of agouti-related protein (AgRP) neuron by cannabinoid receptor type 1 (CB1R). J. Agric. Food. Chem. 65(5), 1051-1057 (2017).
6. Piscitelli, F., Guida, F., Luongo, L., et al. Protective effects of N-oleoylglycine in a mouse model of mild traumatic brain injury. ACS Chem. Neurosci. 11(8), 1117-1128 (2020).

String Representations

InChiKey (Click to copy)
HPFXACZRFJDURI-KTKRTIGZSA-N
InChi (Click to copy)
InChI=1S/C20H37NO3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-19(22)21-18-20(23)24/h9-10H,2-8,11-18H2,1H3,(H,21,22)(H,23,24)/b10-9-
SMILES (Click to copy)
C(CNC(CCCCCCC/C=C\CCCCCCCC)=O)(=O)O

Other Databases

HMDB ID
CHEBI ID
PubChem CID
Cayman ID

Calculated Physicochemical Properties

Heavy Atoms 24
Rings 0
Aromatic Rings 0
Rotatable Bonds 17
Van der Waals Molecular Volume 384.01
Topological Polar Surface Area 66.40
Hydrogen Bond Donors 2
Hydrogen Bond Acceptors 3
logP 5.51
Molar Refractivity 100.59

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Created at
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Updated at
19th Feb 2024