(2S,3S,4S,5R,6S)-6-{4-[(1E)-1-{4-[2-(dimethylamino)ethoxy]phenyl}-2-phenylbut-1-en-1-yl]phenoxy}-3,4,5-trihydroxyoxane-2-carboxylic acid

• ChemBase ID: 171341
• Molecular Formular: C32H37NO8
• Molecular Mass: 563.63808
• Monoisotopic Mass: 563.25191715
• SMILES: c1cc(ccc1O[C@@H]1O[C@H]([C@H]([C@@H]([C@@H]1O)O)O)C(=O)O)/C(=C(\CC)/c1ccccc1)/c1ccc(cc1)OCCN(C)C
• Canonical SMILES: CC/C(=C(/c1ccc(cc1)OCCN(C)C)\c1ccc(cc1)O[C@@H]1O[C@@H](C(=O)O)[C@H]([C@@H]([C@@H]1O)O)O)/c1ccccc1
• InChI: InChI=1S/C32H37NO8/c1-4-25(20-8-6-5-7-9-20)26(21-10-14-23(15-11-21)39-19-18-33(2)3)22-12-16-24(17-13-22)40-32-29(36)27(34)28(35)30(41-32)31(37)38/h5-17,27-30,32,34-36H,4,18-19H2,1-3H3,(H,37,38)/b26-25+/t27-,28-,29+,30-,32+/m0/s1
• InChIKey: SSRNQFUJUAOPJD-OFKVRPASSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S,5R,6S)-6-{4-[(1E)-1-{4-[2-(dimethylamino)ethoxy]phenyl}-2-phenylbut-1-en-1-yl]phenoxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
• IUPAC Traditional name: (2S,3S,4S,5R,6S)-6-{4-[(1E)-1-{4-[2-(dimethylamino)ethoxy]phenyl}-2-phenylbut-1-en-1-yl]phenoxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
• Synonyms: O-β-D-Glucuronide of (Ζ)-4-Hydroxy Tamoxifen; 4-[(1E)-1-[4-[2-(Dimethylamino)ethoxy]phenyl]-2-phenyl-1-buten-1-yl]phenyl β-D-Glucopyranosiduronic Acid; (E)-4-Hydroxy Tamoxifen O-β-D-Glucuronide

Database IDs

• CAS Number: 152764-51-7
• PubChem SID: 164227251
• PubChem CID: 71749358

CALCULATED PROPERTIES

• Acid pKa: 2.933367
• H Acceptors: 9
• H Donor: 4
• LogD (pH = 5.5): 1.3681712
• LogD (pH = 7.4): 1.3539306
• Log P: 1.3684095
• Molar Refractivity: 162.4235 cm^3
• Polarizability: 60.410072 Å^3
• Polar Surface Area: 128.92 Å^2
• Rotatable Bonds: 11
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: White Solid
• Melting Point: 173-176°C

Safety Information

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

DETAILS

Toronto Research Chemicals - H954760

A glucuronide of (Z)-4-Hydroxy Tamoxifen (or trans-4-hydroxytamoxifen), an active metabolite of Tamoxifen (T006000).

REFERENCES

• Beaulieu, M., et al.: J. Biol. Chem., 271, 22855 (1996)
• Green, M., et al.: Drug Metab. Dispos., 26, 860 (1996)
• Nishiyama, T., et al.: Biochem. Pharmacol., 63, 1817 (1996)