(6aR,9R,10aR)-9-(hydroxymethyl)-6,6-dimethyl-3-[2-(2H3)methyl(1,1,1-2H3)octan-2-yl]-6H,6aH,7H,8H,9H,10H,10aH-benzo[c]isochromen-1-ol

• ChemBase ID: 170019
• Molecular Formular: C25H40O3
• Molecular Mass: 388.5833
• Monoisotopic Mass: 388.29774514
• SMILES: C1C[C@@H]2[C@@H](C[C@@H]1CO)c1c(cc(cc1O)C(CCCCCC)(C)C)OC2(C)C
• Canonical SMILES: CCCCCCC(c1cc(O)c2c(c1)OC([C@H]1[C@H]2C[C@H](CO)CC1)(C)C)(C)C
• InChI: InChI=1S/C25H40O3/c1-6-7-8-9-12-24(2,3)18-14-21(27)23-19-13-17(16-26)10-11-20(19)25(4,5)28-22(23)15-18/h14-15,17,19-20,26-27H,6-13,16H2,1-5H3/t17-,19-,20-/m1/s1
• InChIKey: MVEVPDCVOXJVBD-MISYRCLQSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (6aR,9R,10aR)-9-(hydroxymethyl)-6,6-dimethyl-3-[2-(^2H₃)methyl(1,1,1-^2H₃)octan-2-yl]-6H,6aH,7H,8H,9H,10H,10aH-benzo[c]isochromen-1-ol
• IUPAC Traditional name: (6aR,9R,10aR)-9-(hydroxymethyl)-6,6-dimethyl-3-[2-(^2H₃)methyl(1,1,1-^2H₃)octan-2-yl]-6aH,7H,8H,9H,10H,10aH-benzo[c]isochromen-1-ol
• Synonyms: (6aR,9R,10aR)-3-(1,1-Dimethyl-d6-heptyl)-6a,7,8,9,10,10a-hexahydro-1-hydroxy-6,6-dimethyl-6H-dibenzo[b,d]pyran-9-methanol; Canbisol-d6; HU-243-d6; [6aR-(6aα,9α,10aβ)]-3-(1,1-Dimethyl-d6-heptyl)-6a,7,8,9,10,10a-hexahydro-1-hydroxy-6,6-dimethyl-6H-dibenzo[b,d]pyran-9-methanol; AM 4056-d6; HU 243-d6

Database IDs

• PubChem SID: 164225929
• PubChem CID: 71748773

CALCULATED PROPERTIES

• Acid pKa: 10.002438
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 6.4672017
• LogD (pH = 7.4): 6.4661384
• Log P: 6.467215
• Molar Refractivity: 115.9609 cm^3
• Polarizability: 45.614346 Å^3
• Polar Surface Area: 49.69 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - H673512

Labelled analogue of a synthetic cannabinoid derivative that acts as a potent agonist at both the CB1 and CB2 receptors. Controlled Substance.

REFERENCES

• Rhee, M.H. et al.: J. Med. Chem., 40, 3228 (1997)
• Rhee, M.H. et al.: J. Neurochem., 75, 2485 (1997)
• Zhang, R. et al.: Mol. Pharmacol., 68, 69 (1997)