(2S,3S,4S,5R,6R)-6-[(2-{4-[(1Z)-1,2-diphenylbut-1-en-1-yl]phenoxy}ethyl)dimethylazaniumyl]-3,4,5-trihydroxyoxane-2-carboxylate

• ChemBase ID: 178051
• Molecular Formular: C32H37NO7
• Molecular Mass: 547.63868
• Monoisotopic Mass: 547.25700253
• SMILES: c1c(ccc(c1)/C(=C(/CC)\c1ccccc1)/c1ccccc1)OCC[N+]([C@@H]1O[C@H]([C@H]([C@@H]([C@@H]1O)O)O)C(=O)[O-])(C)C
• Canonical SMILES: CC/C(=C(\c1ccccc1)/c1ccc(cc1)OCC[N+]([C@@H]1O[C@@H](C(=O)[O-])[C@H]([C@@H]([C@@H]1O)O)O)(C)C)/c1ccccc1
• InChI: InChI=1S/C32H37NO7/c1-4-25(21-11-7-5-8-12-21)26(22-13-9-6-10-14-22)23-15-17-24(18-16-23)39-20-19-33(2,3)31-29(36)27(34)28(35)30(40-31)32(37)38/h5-18,27-31,34-36H,4,19-20H2,1-3H3/b26-25-/t27-,28-,29+,30-,31+/m0/s1
• InChIKey: UKFQQYJAYUAYES-DTMHFWPESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S,5R,6R)-6-[(2-{4-[(1Z)-1,2-diphenylbut-1-en-1-yl]phenoxy}ethyl)dimethylazaniumyl]-3,4,5-trihydroxyoxane-2-carboxylate
• IUPAC Traditional name: (2S,3S,4S,5R,6R)-6-[(2-{4-[(1Z)-1,2-diphenylbut-1-en-1-yl]phenoxy}ethyl)dimethylammonio]-3,4,5-trihydroxyoxane-2-carboxylate
• Synonyms: 2-[4-[(1E/Z)-1,2-Diphenyl-1-buten-1-yl]phenoxy]-N-β-D-glucopyranuronosyl-N,N-dimethylethanaminium; (E,Z)-Tamoxifen N-β-D-Glucuronide (~92%)

Database IDs

• PubChem SID: 164233961
• PubChem CID: 71752308

CALCULATED PROPERTIES

• Acid pKa: 3.176874
• H Acceptors: 7
• H Donor: 3
• LogD (pH = 5.5): 0.86402065
• LogD (pH = 7.4): 0.86566585
• Log P: 0.09519773
• Molar Refractivity: 182.711 cm^3
• Polarizability: 59.556145 Å^3
• Polar Surface Area: 119.28 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: Beige Solid
• Melting Point: 119-121°C (dec.)

Safety Information

• Storage Condition: -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - T006085

Α metabolite of Tamoxifen (T006000).

REFERENCES

• Sun, D., et al.: Breast Cancer Res., 8(4)
• (4)
• Zheng, Y., et al.: Drug Metab. Dispos., 35, 1942 (4)