(6aR,10aR)-1-hydroxy-6,6-dimethyl-3-[(2,2,3,3,4,4,5,5,5-2H9)pentyl]-6H,6aH,7H,10H,10aH-benzo[c]isochromene-9-carboxylic acid

• ChemBase ID: 178297
• Molecular Formular: C21H28O4
• Molecular Mass: 344.44462
• Monoisotopic Mass: 344.19875938
• SMILES: C1(=CC[C@@H]2[C@@H](C1)c1c(OC2(C)C)cc(cc1O)CCCCC)C(=O)O
• Canonical SMILES: CCCCCc1cc(O)c2c(c1)OC([C@H]1[C@H]2CC(=CC1)C(=O)O)(C)C
• InChI: InChI=1S/C21H28O4/c1-4-5-6-7-13-10-17(22)19-15-12-14(20(23)24)8-9-16(15)21(2,3)25-18(19)11-13/h8,10-11,15-16,22H,4-7,9,12H2,1-3H3,(H,23,24)/t15-,16-/m1/s1
• InChIKey: OGXXAQFMAFTSRU-HZPDHXFCSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (6aR,10aR)-1-hydroxy-6,6-dimethyl-3-[(2,2,3,3,4,4,5,5,5-^2H₉)pentyl]-6H,6aH,7H,10H,10aH-benzo[c]isochromene-9-carboxylic acid
• IUPAC Traditional name: (6aR,10aR)-1-hydroxy-6,6-dimethyl-3-[(2,2,3,3,4,4,5,5,5-^2H₉)pentyl]-6aH,7H,10H,10aH-benzo[c]isochromene-9-carboxylic acid
• Synonyms: 6aR,10aR)-6a,7,10,10a-Tetrahydro-1-hydroxy-6,6-dimethyl-3-pentyl-6H-dibenzo[b,d]pyran-9-carboxylic Acid-d9; (6aR-trans)-6a,7,10,10a-Tetrahydro-1-hydroxy-6,6-dimethyl-3-pentyl-6H-dibenzo[b,d]pyran-9-carboxylic Acid-d9; (-)-9-Nor-9-carboxy-Δ8-tetrahydrocannabinol-d9; 11-Nor-Δ8-Tetrahydrocannabinol-8-carboxylic Acid-d9; 9-Carboxy-11-nor-Δ8-tetrahydrocannabinol-d9; Δ1(6)-Tetrahydrocannabinol-7-oic Acid-d9; Δ6-Tetrahydrocannabinol-7-oic Acid-d9; Δ8-THC-11-oic Acid-d9; Δ8-Tetrahydro Cannabinol-11-oic Acid-d9

Database IDs

• PubChem SID: 164234207
• PubChem CID: 71752423

CALCULATED PROPERTIES

• Acid pKa: 4.2535286
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 3.867675
• LogD (pH = 7.4): 2.1385074
• Log P: 5.1358495
• Molar Refractivity: 98.4507 cm^3
• Polarizability: 37.88887 Å^3
• Polar Surface Area: 66.76 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - T293247

Labelled Δ8-Tetrahydro Cannabinol-11-oic Acid (T293245). Δ8-Tetrahydro Cannabinol-11-oic acid is a derivative of Δ8-Tetrahydrocannabinol (T293240) used for decreasing cell proliferation in a mammal (cancer treatment).

REFERENCES

• Hammett-Stabler, C., et al.: Clin. Chim. Acta, 315, 125 (2002)
• Wu, A., et al.: J. Anal. Toxicol., 17, 241 (2002)
• Ferrara, S., et al.: J. Anal. Toxicol., 18, 278 (2002)