(6aR,8R,10aR)-6,6,9-trimethyl-3-pentyl-6H,6aH,7H,8H,10aH-benzo[c]isochromene-1,8-diol

• ChemBase ID: 171351
• Molecular Formular: C21H30O3
• Molecular Mass: 330.4611
• Monoisotopic Mass: 330.21949482
• SMILES: C1(=C[C@@H]2[C@@H](C[C@H]1O)C(Oc1c2c(cc(c1)CCCCC)O)(C)C)C
• Canonical SMILES: CCCCCc1cc(O)c2c(c1)OC([C@H]1[C@H]2C=C(C)[C@@H](C1)O)(C)C
• InChI: InChI=1S/C21H30O3/c1-5-6-7-8-14-10-18(23)20-15-9-13(2)17(22)12-16(15)21(3,4)24-19(20)11-14/h9-11,15-17,22-23H,5-8,12H2,1-4H3/t15-,16-,17-/m1/s1
• InChIKey: INKUWBOHCFHXTJ-BRWVUGGUSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (6aR,8R,10aR)-6,6,9-trimethyl-3-pentyl-6H,6aH,7H,8H,10aH-benzo[c]isochromene-1,8-diol
• IUPAC Traditional name: (6aR,8R,10aR)-6,6,9-trimethyl-3-pentyl-6aH,7H,8H,10aH-benzo[c]isochromene-1,8-diol
• Synonyms: (6aR,8R,10aR)-6a,7,8,10a-Tetrahydro-6,6,9-trimethyl-3-pentyl-6H-dibenzo[b,d]pyran-1,8-diol; (-)-8β-Hydroxy-Δ9-tetrahydrocannabinol; 8β-Hydroxy-Δ9-THC; 8β-Hydroxy-Δ9-tetrahydro Cannabinol

Database IDs

• CAS Number: 34984-78-6
• PubChem SID: 164227261
• PubChem CID: 169652

CALCULATED PROPERTIES

• Acid pKa: 9.342395
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 4.713284
• LogD (pH = 7.4): 4.708446
• Log P: 4.713346
• Molar Refractivity: 98.249 cm^3
• Polarizability: 38.074955 Å^3
• Polar Surface Area: 49.69 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - H957100

A metabolite of Δ9-tetrahydrocannabinol (Δ9-THC).

REFERENCES

• Manno, J., et al.: J. Anal. Toxicol., 25, 538 (2001)
• Skopp, G., et al.: Clin. Chem., 48, 301 (2001)
• Nadulski, T., et al.: Ther. Drug Monit., 27, 799 (2001)
• Blake, D., et al.: Rheumatology, 45, 50 (2001)