2-[(1R,6R)-3-methyl-6-(prop-1-en-2-yl)cyclohex-2-en-1-yl]-5-[(2,2,3,3,4,4,5,5,5-2H9)pentyl]benzene-1,3-diol

• ChemBase ID: 163576
• Molecular Formular: C21H30O2
• Molecular Mass: 314.4617
• Monoisotopic Mass: 314.2245802
• SMILES: c1c(cc(c(c1O)[C@H]1[C@@H](CCC(=C1)C)C(=C)C)O)CCCCC
• Canonical SMILES: CCCCCc1cc(O)c(c(c1)O)[C@@H]1C=C(C)CC[C@H]1C(=C)C
• InChI: InChI=1S/C21H30O2/c1-5-6-7-8-16-12-19(22)21(20(23)13-16)18-11-15(4)9-10-17(18)14(2)3/h11-13,17-18,22-23H,2,5-10H2,1,3-4H3/t17-,18+/m0/s1
• InChIKey: QHMBSVQNZZTUGM-ZWKOTPCHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[(1R,6R)-3-methyl-6-(prop-1-en-2-yl)cyclohex-2-en-1-yl]-5-[(2,2,3,3,4,4,5,5,5-^2H₉)pentyl]benzene-1,3-diol
• IUPAC Traditional name: 2-[(1R,6R)-3-methyl-6-(prop-1-en-2-yl)cyclohex-2-en-1-yl]-5-[(2,2,3,3,4,4,5,5,5-^2H₉)pentyl]benzene-1,3-diol
• Synonyms: 2-[(1R,6R)-3-Methyl-6-(1-methylethenyl)-2-cyclohexen-1-yl]-5-(pentyl-d9)-1,3-benzenediol; trans-(-)-(2-p-Mentha-1,8-dien-3-yl-5-(pentyl-d9)resorcinol; (-)-CBD-d9; (-)-trans-Cannabidiol-d9; CBD-d9; Δ1(2)-trans-Cannabidiol-d9; (-)-Cannabidiol-d9

Database IDs

• PubChem SID: 162257711
• PubChem CID: 71314488

CALCULATED PROPERTIES

• Acid pKa: 9.12873
• H Acceptors: 2
• H Donor: 2
• LogD (pH = 5.5): 6.3250995
• LogD (pH = 7.4): 6.3172107
• Log P: 6.325201
• Molar Refractivity: 98.5309 cm^3
• Polarizability: 37.90469 Å^3
• Polar Surface Area: 40.46 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - C175302

Labelled (-)-Cannabidiol (C175300). Major non-psychoactive constituent of Cannabis. Exhibits multiple bioactivities including anticonvulsant, anxiolytic and anti-inflammatory effects. The (+)-isomers were more active than the (-)-isomers.

REFERENCES

• Mechoulam, R., et al.: J. Clin. Pharmacol., 42, 11S (2002)
• Harvey, R., et al.: Science, 304, 884 (2002)
• Haeseler, G., et al.: Br. J. Pharmacol., 145, 916 ( 2005), Betz, H., et al.: J. Neurochem., 97, 1600 (2002)