N-arachidonoylglycine

Ligand id: 3635

Name: N-arachidonoylglycine

Abbreviated name: NAG

Structure and Physico-chemical Properties

2D Structure
Calculated Physico-chemical Properties
Hydrogen bond acceptors 4
Hydrogen bond donors 2
Rotatable bonds 17
Topological polar surface area 66.4
Molecular weight 361.26
XLogP 7.52
No. Lipinski's rules broken 2

Molecular properties generated using the CDK

References
1. Davenport AP, Alexander SP, Sharman JL, Pawson AJ, Benson HE, Monaghan AE, Liew WC, Mpamhanga CP, Bonner TI, Neubig RR et al.. (2013)
International Union of Basic and Clinical Pharmacology. LXXXVIII. G protein-coupled receptor list: recommendations for new pairings with cognate ligands.
Pharmacol. Rev., 65 (3): 967-86. [PMID:23686350]
2. Kohno M, Hasegawa H, Inoue A, Muraoka M, Miyazaki T, Oka K, Yasukawa M. (2006)
Identification of N-arachidonylglycine as the endogenous ligand for orphan G-protein-coupled receptor GPR18.
Biochem. Biophys. Res. Commun., 347 (3): 827-32. [PMID:16844083]
3. McHugh D, Page J, Dunn E, Bradshaw HB. (2012)
Δ(9) -Tetrahydrocannabinol and N-arachidonyl glycine are full agonists at GPR18 receptors and induce migration in human endometrial HEC-1B cells.
Br. J. Pharmacol., 165 (8): 2414-24. [PMID:21595653]
4. Oh DY, Yoon JM, Moon MJ, Hwang JI, Choe H, Lee JY, Kim JI, Kim S, Rhim H, O'Dell DK, Walker JM, Na HS, Lee MG, Kwon HB, Kim K, Seong JY. (2008)
Identification of farnesyl pyrophosphate and N-arachidonylglycine as endogenous ligands for GPR92.
J. Biol. Chem., 283 (30): 21054-64. [PMID:18499677]
5. 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]
6. Williams JR, Khandoga AL, Goyal P, Fells JI, Perygin DH, Siess W, Parrill AL, Tigyi G, Fujiwara Y. (2009)
Unique ligand selectivity of the GPR92/LPA5 lysophosphatidate receptor indicates role in human platelet activation.
J. Biol. Chem., 284 (25): 17304-19. [PMID:19366702]
7. Yin H, Chu A, Li W, Wang B, Shelton F, Otero F, Nguyen DG, Caldwell JS, Chen YA. (2009)
Lipid G protein-coupled receptor ligand identification using beta-arrestin PathHunter assay.
J Biol Chem, 284: 12328-12338. [PMID:19286662]