2-[(1S,3R)-3-hydroxycyclohexyl]-5-[2-(2H3)methyl(1,1,1-2H3)nonan-2-yl]phenol

• ChemBase ID: 170491
• Molecular Formular: C22H36O2
• Molecular Mass: 332.52004
• Monoisotopic Mass: 332.27153039
• SMILES: C1CC[C@@H](C[C@@H]1O)c1ccc(cc1O)C(CCCCCCC)(C)C
• Canonical SMILES: CCCCCCCC(c1ccc(c(c1)O)[C@H]1CCC[C@H](C1)O)(C)C
• InChI: InChI=1S/C22H36O2/c1-4-5-6-7-8-14-22(2,3)18-12-13-20(21(24)16-18)17-10-9-11-19(23)15-17/h12-13,16-17,19,23-24H,4-11,14-15H2,1-3H3/t17-,19+/m0/s1
• InChIKey: HNMJDLVMIUDJNH-PKOBYXMFSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[(1S,3R)-3-hydroxycyclohexyl]-5-[2-(^2H₃)methyl(1,1,1-^2H₃)nonan-2-yl]phenol
• IUPAC Traditional name: 2-[(1S,3R)-3-hydroxycyclohexyl]-5-[2-(^2H₃)methyl(1,1,1-^2H₃)nonan-2-yl]phenol
• Synonyms: rel-5-[1,1-(Dimethyl-d6)octyl]-2-[(1R,3S)-3-hydroxycyclohexyl]phenol; cis-5-[1,1-(Dimethyl-d6)octyl]-2-(3-hydroxycyclohexyl)phenol; Cannabicyclohexanol-d6; (cis)-3-[2-Hydroxy-4-[1,1-(dimethyl-d6)octyl]phenyl]cyclohexanol

Database IDs

• PubChem SID: 164226401
• PubChem CID: 71748994

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 2
• LogD (pH = 5.5): 6.610415
• LogD (pH = 7.4): 6.6100607
• Log P: 6.6104193
• Molar Refractivity: 102.1719 cm^3
• Polarizability: 40.15992 Å^3
• Polar Surface Area: 40.46 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: false
• Acid pKa: 10.480125

DETAILS

Toronto Research Chemicals - H941622

A labelled bicyclic cannabinoid analog with possible analgesic application. Used in the identification and study of receptor binding sites at which canabimimetic effects are initiated.

REFERENCES

• Compton, D.R. et al.: J. Pharmacol. Exp. Therap., 260, 201 (1992)
• Melvin. L.S. et al.: Molec. Pharmacol., 44, 1008 (1992)