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
3D model of N-oleoyl glycine
Please note: Where there are chiral atoms but the stereochemistry is undefined, the 3D model takes an arbitrary conformation
Classification
Category
Main Class
Sub Class
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
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
Admin
Created at
-
Updated at
19th Feb 2024