arachidonylcyclopropylamide   Click here for help

GtoPdb Ligand ID: 739

Abbreviated name: ACPA
Synonyms: arachidonyl cyclopropylamide
Compound class: Synthetic organic
Comment: A synthetic CB1 receptor agonist.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 2
Hydrogen bond donors 1
Rotatable bonds 16
Topological polar surface area 29.1
Molecular weight 343.29
XLogP 8.68
No. Lipinski's rules broken 2
SMILES / InChI / InChIKey
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Canonical SMILES CCCCCC=CCC=CCC=CCC=CCCCC(=O)NC1CC1
Isomeric SMILES CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)NC1CC1
InChI InChI=1S/C23H37NO/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-23(25)24-22-20-21-22/h6-7,9-10,12-13,15-16,22H,2-5,8,11,14,17-21H2,1H3,(H,24,25)/b7-6-,10-9-,13-12-,16-15-
InChI Key GLGAUBPACOBAMV-DOFZRALJSA-N
References
1. Hillard CJ, Manna S, Greenberg MJ, DiCamelli R, Ross RA, Stevenson LA, Murphy V, Pertwee RG, Campbell WB. (1999)
Synthesis and characterization of potent and selective agonists of the neuronal cannabinoid receptor (CB1).
J Pharmacol Exp Ther, 289 (3): 1427-33. [PMID:10336536]
2. 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]