[(1S,4S,5S)-4-[2,6-dimethoxy-4-(2-methyloctan-2-yl)phenyl]-6,6-dimethylbicyclo[3.1.1]hept-2-en-2-yl]methanol

• ChemBase ID: 170020
• Molecular Formular: C27H42O3
• Molecular Mass: 414.62058
• Monoisotopic Mass: 414.3133952
• SMILES: [C@@H]12C([C@@H]([C@H](C=C1CO)c1c(cc(cc1OC)C(CCCCCC)(C)C)OC)C2)(C)C
• Canonical SMILES: CCCCCCC(c1cc(OC)c(c(c1)OC)[C@H]1C=C(CO)[C@@H]2C[C@H]1C2(C)C)(C)C
• InChI: InChI=1S/C27H42O3/c1-8-9-10-11-12-26(2,3)19-14-23(29-6)25(24(15-19)30-7)20-13-18(17-28)21-16-22(20)27(21,4)5/h13-15,20-22,28H,8-12,16-17H2,1-7H3/t20-,21+,22-/m0/s1
• InChIKey: CFMRIVODIXTERW-BDTNDASRSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [(1S,4S,5S)-4-[2,6-dimethoxy-4-(2-methyloctan-2-yl)phenyl]-6,6-dimethylbicyclo[3.1.1]hept-2-en-2-yl]methanol
• IUPAC Traditional name: [(1S,4S,5S)-4-[2,6-dimethoxy-4-(2-methyloctan-2-yl)phenyl]-6,6-dimethylbicyclo[3.1.1]hept-2-en-2-yl]methanol
• Synonyms: (1R,4R,5R)-rel-(+)-4-[4-(1,1-Dimethylheptyl)-2,6-dimethoxyphenyl]-6,6-dimethylbicyclo[3.1.1]hept-2-ene-2-methanol; HU 308

Database IDs

• CAS Number: 256934-39-1
• PubChem SID: 164225930
• PubChem CID: 11553430

CALCULATED PROPERTIES

• Acid pKa: 15.148779
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 6.3942704
• LogD (pH = 7.4): 6.3942704
• Log P: 6.3942704
• Molar Refractivity: 125.7379 cm^3
• Polarizability: 49.21343 Å^3
• Polar Surface Area: 38.69 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - H673525

A specific CB2-specific agonist that inhibits forskolin-stimulated cAMP production in CB2-transfected cells. It reduces blood pressure, blocks defecation, and elicits anti-inflammatory and peripheral analgesic activity and thus may lead to new therapies f

REFERENCES

• Hanus, L. et al.: Proc. Nat. Acad. Sci. USA, 96, 14228 (1999)
• Labud, C.J. et al.: Eur. J. Pharmacol., 527, 172 (1999)
• Martin-Moreno, A.M. et al.: Molec. Pharmacol., 79, 964 (1999)