(5Z,8Z,11Z,14Z)-N-[2-chloro(2H4)ethyl]icosa-5,8,11,14-tetraenamide

• ChemBase ID: 160786
• Molecular Formular: C22H36ClNO
• Molecular Mass: 365.98034
• Monoisotopic Mass: 365.24854246
• SMILES: C(=O)(CCC/C=C\C/C=C\C/C=C\C/C=C\CCCCC)NCCCl
• Canonical SMILES: CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)NCCCl
• InChI: InChI=1S/C22H36ClNO/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-22(25)24-21-20-23/h6-7,9-10,12-13,15-16H,2-5,8,11,14,17-21H2,1H3,(H,24,25)/b7-6-,10-9-,13-12-,16-15-
• InChIKey: SCJNCDSAIRBRIA-DOFZRALJSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (5Z,8Z,11Z,14Z)-N-[2-chloro(^2H₄)ethyl]icosa-5,8,11,14-tetraenamide
• IUPAC Traditional name: (5Z,8Z,11Z,14Z)-N-[2-chloro(^2H₄)ethyl]icosa-5,8,11,14-tetraenamide
• Synonyms: (5Z,8Z,11Z,14Z)-N-(2-Chloroethyl-d4)-5,8,11,14-eicosatetraenamide; ACEA-d4; Arachidonyl-2-(chloroethyl-d4)amide

Database IDs

• PubChem SID: 162254921
• PubChem CID: 71313481

CALCULATED PROPERTIES

• Acid pKa: 14.996904
• H Acceptors: 1
• H Donor: 1
• LogD (pH = 5.5): 6.6683936
• LogD (pH = 7.4): 6.668394
• Log P: 6.668394
• Molar Refractivity: 116.0162 cm^3
• Polarizability: 43.323685 Å^3
• Polar Surface Area: 29.1 Å^2
• Rotatable Bonds: 16
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - A765022

A labelled synthetic agonist of the cannabinoid receptor 1 (CB1R). ACEA 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

• Luszczki, J.J. et al.: Prog. Neuro-Psychopharmacol. Biol. Psych., 34, 18 (1999)
• Hillard, C.J. et al.: J. Pharmacol. Exp. Therap., 289, 1427 (1999)