(2S,3S,4S,5R,6S)-6-{[(6aR,10aR)-9-carboxy-6,6-dimethyl-3-pentyl-6H,6aH,7H,8H,10aH-benzo[c]isochromen-1-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid

• ChemBase ID: 178293
• Molecular Formular: C27H36O10
• Molecular Mass: 520.56874
• Monoisotopic Mass: 520.23084735
• SMILES: [C@@H]1([C@@H]([C@@H]([C@@H](O[C@H]1C(=O)O)Oc1c2[C@H]3[C@@H](CCC(=C3)C(=O)O)C(Oc2cc(c1)CCCCC)(C)C)O)O)O
• Canonical SMILES: CCCCCc1cc(O[C@@H]2O[C@@H](C(=O)O)[C@H]([C@@H]([C@@H]2O)O)O)c2c(c1)OC([C@H]1[C@H]2C=C(CC1)C(=O)O)(C)C
• InChI: InChI=1S/C27H36O10/c1-4-5-6-7-13-10-17(35-26-22(30)20(28)21(29)23(36-26)25(33)34)19-15-12-14(24(31)32)8-9-16(15)27(2,3)37-18(19)11-13/h10-12,15-16,20-23,26,28-30H,4-9H2,1-3H3,(H,31,32)(H,33,34)/t15-,16-,20+,21+,22-,23+,26-/m1/s1
• InChIKey: BHNZRIZYCGDZNQ-UCEZHQNTSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S,5R,6S)-6-{[(6aR,10aR)-9-carboxy-6,6-dimethyl-3-pentyl-6H,6aH,7H,8H,10aH-benzo[c]isochromen-1-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
• IUPAC Traditional name: (2S,3S,4S,5R,6S)-6-{[(6aR,10aR)-9-carboxy-6,6-dimethyl-3-pentyl-6aH,7H,8H,10aH-benzo[c]isochromen-1-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
• Synonyms: (6aR,10aR)-9-Carboxy-6a,7,8,10a-tetrahydro-6,6-dimethyl-3-pentyl-6H-dibenzo[b,d]pyran-1-yl β-D-Glucopyranosiduronic Acid; 11-Nor-9-Tetrahydrocannabinol-9carboxylicAcid Glucuronide; 11-Δ9-Tetrahydro Cannabinol-9-carboxylic Acid β-D-Glucuronide

Database IDs

• CAS Number: 84376-63-6
• PubChem SID: 164234203
• PubChem CID: 71752420

CALCULATED PROPERTIES

• Acid pKa: 3.0940514
• H Acceptors: 10
• H Donor: 5
• LogD (pH = 5.5): -0.67518973
• LogD (pH = 7.4): -3.4450338
• Log P: 3.1880562
• Molar Refractivity: 130.4625 cm^3
• Polarizability: 51.573296 Å^3
• Polar Surface Area: 162.98 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - T293215

A metabolite of Tetrahydrocannabinol (T293200).

REFERENCES

• Lemberger, L., et al.: Science, 170, 1320 (1970)
• Williams, P., et al.: J. Pharm. Pharmacol., 32, 445 (1970)
• Agurell, S., et al.: Pharmacol. Rev., 38, 21 (1970)
• Carrupt, P., et al.: J. Med. Chem., 34, 1272 (1970)
• Kemp, P., et al.: J. Anal. Toxicol., 1