N-oleoylethanolamide   Click here for help

GtoPdb Ligand ID: 2661

Synonyms: N-oleoylethanolamine | NOE | OEA | oleylethanolamide
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 3
Hydrogen bond donors 2
Rotatable bonds 18
Topological polar surface area 49.33
Molecular weight 325.3
XLogP 7.27
No. Lipinski's rules broken 2
SMILES / InChI / InChIKey
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Canonical SMILES CCCCCCCCC=CCCCCCCCC(=O)NCCO
Isomeric SMILES CCCCCCCC/C=C\CCCCCCCC(=O)NCCO
InChI InChI=1S/C20H39NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-20(23)21-18-19-22/h9-10,22H,2-8,11-19H2,1H3,(H,21,23)/b10-9-
InChI Key BOWVQLFMWHZBEF-KTKRTIGZSA-N
References
1. Chu ZL, Carroll C, Chen R, Alfonso J, Gutierrez V, He H, Lucman A, Xing C, Sebring K, Zhou J et al.. (2010)
N-oleoyldopamine enhances glucose homeostasis through the activation of GPR119.
Mol Endocrinol, 24 (1): 161-70. [PMID:19901198]
2. Fu J, Gaetani S, Oveisi F, Lo Verme J, Serrano A, Rodríguez De Fonseca F, Rosengarth A, Luecke H, Di Giacomo B, Tarzia G, Piomelli D. (2003)
Oleylethanolamide regulates feeding and body weight through activation of the nuclear receptor PPAR-alpha.
Nature, 425 (6953): 90-3. [PMID:12955147]
3. Fu J, Oveisi F, Gaetani S, Lin E, Piomelli D. (2005)
Oleoylethanolamide, an endogenous PPAR-alpha agonist, lowers body weight and hyperlipidemia in obese rats.
Neuropharmacology, 48 (8): 1147-53. [PMID:15910890]
4. Overton HA, Babbs AJ, Doel SM, Fyfe MC, Gardner LS, Griffin G, Jackson HC, Procter MJ, Rasamison CM, Tang-Christensen M et al.. (2006)
Deorphanization of a G protein-coupled receptor for oleoylethanolamide and its use in the discovery of small-molecule hypophagic agents.
Cell Metab, 3 (3): 167-75. [PMID:16517404]
5. Ryberg E, Larsson N, Sjögren S, Hjorth S, Hermansson NO, Leonova J, Elebring T, Nilsson K, Drmota T, Greasley PJ. (2007)
The orphan receptor GPR55 is a novel cannabinoid receptor.
Br J Pharmacol, 152 (7): 1092-101. [PMID:17876302]
6. Southern C, Cook JM, Neetoo-Isseljee Z, Taylor DL, Kettleborough CA, Merritt A, Bassoni DL, Raab WJ, Quinn E, Wehrman TS et al.. (2013)
Screening β-Arrestin Recruitment for the Identification of Natural Ligands for Orphan G-Protein-Coupled Receptors.
J Biomol Screen, 18 (5): 599-609. [PMID:23396314]
7. Ueda N, Yamanaka K, Yamamoto S. (2001)
Purification and characterization of an acid amidase selective for N-palmitoylethanolamine, a putative endogenous anti-inflammatory substance.
J Biol Chem, 276 (38): 35552-7. [PMID:11463796]
8. Wei BQ, Mikkelsen TS, McKinney MK, Lander ES, Cravatt BF. (2006)
A second fatty acid amide hydrolase with variable distribution among placental mammals.
J Biol Chem, 281 (48): 36569-78. [PMID:17015445]