(2S,3S,4S,5R,6S)-6-[(6aR,10aR)-1-hydroxy-6,6-dimethyl-3-pentyl-6H,6aH,7H,8H,10aH-benzo[c]isochromene-9-carbonyloxy]-3,4,5-trihydroxyoxane-2-carboxylic acid

• ChemBase ID: 178292
• 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)OC(=O)C1=C[C@@H]2[C@@H](CC1)C(Oc1c2c(cc(c1)CCCCC)O)(C)C)O)O)O
• Canonical SMILES: CCCCCc1cc(O)c2c(c1)OC([C@H]1[C@H]2C=C(CC1)C(=O)O[C@@H]1O[C@@H](C(=O)O)[C@H]([C@@H]([C@@H]1O)O)O)(C)C
• InChI: InChI=1S/C27H36O10/c1-4-5-6-7-13-10-17(28)19-15-12-14(8-9-16(15)27(2,3)37-18(19)11-13)25(34)36-26-22(31)20(29)21(30)23(35-26)24(32)33/h10-12,15-16,20-23,26,28-31H,4-9H2,1-3H3,(H,32,33)/t15-,16-,20+,21+,22-,23+,26+/m1/s1
• InChIKey: UWXZAZRSQQLWKH-XUEDFLTMSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S,5R,6S)-6-[(6aR,10aR)-1-hydroxy-6,6-dimethyl-3-pentyl-6H,6aH,7H,8H,10aH-benzo[c]isochromene-9-carbonyloxy]-3,4,5-trihydroxyoxane-2-carboxylic acid
• IUPAC Traditional name: (2S,3S,4S,5R,6S)-6-[(6aR,10aR)-1-hydroxy-6,6-dimethyl-3-pentyl-6aH,7H,8H,10aH-benzo[c]isochromene-9-carbonyloxy]-3,4,5-trihydroxyoxane-2-carboxylic acid
• Synonyms: 1-O-[[(6aR,10aR-6a,7,8,10a-Tetrahydro-1-hydroxy-6,6-dimethyl-3-pentyl-6H-dibenzo[b,d]pyran-9-yl]carbonyl]-β-D-glucopyranuronic Acid; 11-Nor-Δ9-Tetrahydro Cannabinol-9-carboxylate Acyl-β-D-glucuronide

Database IDs

• CAS Number: 76448-35-6
• PubChem SID: 164234202
• PubChem CID: 173519

CALCULATED PROPERTIES

• Acid pKa: 3.2921772
• H Acceptors: 9
• H Donor: 5
• LogD (pH = 5.5): 1.2310513
• LogD (pH = 7.4): -0.011264082
• Log P: 3.4213896
• Molar Refractivity: 130.7493 cm^3
• Polarizability: 51.748344 Å^3
• Polar Surface Area: 162.98 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - T293210

The major 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