(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{4-[(1E)-1-{4-[2-(methylamino)ethoxy]phenyl}-2-phenyl(2H5)but-1-en-1-yl]phenoxy}oxane-2-carboxylic acid

• ChemBase ID: 166577
• Molecular Formular: C31H35NO8
• Molecular Mass: 549.6115
• Monoisotopic Mass: 549.23626709
• 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)OCCNC
• Canonical SMILES: CNCCOc1ccc(cc1)/C(=C(\c1ccccc1)/CC)/c1ccc(cc1)O[C@@H]1O[C@@H](C(=O)O)[C@H]([C@@H]([C@@H]1O)O)O
• InChI: InChI=1S/C31H35NO8/c1-3-24(19-7-5-4-6-8-19)25(20-9-13-22(14-10-20)38-18-17-32-2)21-11-15-23(16-12-21)39-31-28(35)26(33)27(34)29(40-31)30(36)37/h4-16,26-29,31-35H,3,17-18H2,1-2H3,(H,36,37)/b25-24+/t26-,27-,28+,29-,31+/m0/s1
• InChIKey: HSQYCNXRYHIGKV-QXBBUDDSSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{4-[(1E)-1-{4-[2-(methylamino)ethoxy]phenyl}-2-phenyl(^2H₅)but-1-en-1-yl]phenoxy}oxane-2-carboxylic acid
• IUPAC Traditional name: (2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{4-[(1E)-1-{4-[2-(methylamino)ethoxy]phenyl}-2-phenyl(^2H₅)but-1-en-1-yl]phenoxy}oxane-2-carboxylic acid
• Synonyms: 4-[1-[4-[2-(Methylamino)ethoxy]phenyl]-2-phenyl-1-buten-1-yl]phenyl-d5 β-D-Glucopyranosiduronic Acid; (E/Z)-Endoxifen Glucuronide; N-Desmethyl-4-hydroxy Tamoxifen-d5 β-D-Glucuronide(E/Z Mixture)

Database IDs

• PubChem SID: 162260710
• PubChem CID: 71315789

CALCULATED PROPERTIES

• Acid pKa: 2.9333677
• H Acceptors: 9
• H Donor: 5
• LogD (pH = 5.5): 1.2443446
• LogD (pH = 7.4): 1.2422788
• Log P: 1.2449282
• Molar Refractivity: 157.1288 cm^3
• Polarizability: 58.572308 Å^3
• Polar Surface Area: 137.71 Å^2
• Rotatable Bonds: 11
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO
• Apperance: Off-White Solid
• Melting Point: 228-232°C (dec.)

Safety Information

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

DETAILS

Toronto Research Chemicals - D293862

A novel active labelled metabolite of the anti-cancer drug Tamoxifen (T006000).

REFERENCES

• Furr, B., et al.: Pharmacol. Ther., 25, 127 (1984)
• Leonessa, F., et al.: Cancer Res., 54, 441 (1984)
• Stearns, V., et al.: Lancet, 360, 1851 (1984)
• Rae, J., et al.: Pharmacogenetics, 13, 501 (1984)
• Zheng, Y., et al.: Drug Metab. Dispos., 35, 1942 (2007