(5Z,8Z,11Z,14Z)-N-cyclopropylicosa-5,8,11,14-tetraenamide

• ChemBase ID: 160787
• Molecular Formular: C23H37NO
• Molecular Mass: 343.54598
• Monoisotopic Mass: 343.28751481
• SMILES: C(=O)(CCC/C=C\C/C=C\C/C=C\C/C=C\CCCCC)NC1CC1
• Canonical 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-
• InChIKey: GLGAUBPACOBAMV-DOFZRALJSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (5Z,8Z,11Z,14Z)-N-cyclopropylicosa-5,8,11,14-tetraenamide
• IUPAC Traditional name: arachidonylcyclopropylamide
• Synonyms: (5Z,8Z,11Z,14Z)-N-Cyclopropyl-5,8,11,14-eicosatetraenamide; ACPA; Arachidonylcyclopropylamide

Database IDs

• CAS Number: 229021-64-1
• PubChem SID: 162254922
• PubChem CID: 5311007

CALCULATED PROPERTIES

• Acid pKa: 16.036999
• H Acceptors: 1
• H Donor: 1
• LogD (pH = 5.5): 6.4694676
• LogD (pH = 7.4): 6.4694686
• Log P: 6.4694686
• Molar Refractivity: 113.8841 cm^3
• Polarizability: 42.673275 Å^3
• Polar Surface Area: 29.1 Å^2
• Rotatable Bonds: 15
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - A765030

A synthetic agonist of the cannabinoid receptor 1 (CB1R). ACPA is considered to be a selective cannabinoid agonist as it binds primarily to the CB1R and has low affinity to the cannabinoid receptor 2 (CB2R).

REFERENCES

• Hillard, C.J. et al.: J. Pharmacol. Exp. Therap., 289, 1427 (1999)
• Franklin, A. et al.: Eur. J. Pharmacol., 474, 195 (1999)