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

• ChemBase ID: 166551
• Molecular Formular: C31H35NO8
• Molecular Mass: 549.6115
• Monoisotopic Mass: 549.23626709
• SMILES: c1(cc(ccc1)/C(=C(\CC)/c1ccccc1)/c1ccc(cc1)OCCNC)O[C@@H]1O[C@H]([C@H]([C@@H]([C@@H]1O)O)O)C(=O)O
• Canonical SMILES: CNCCOc1ccc(cc1)/C(=C(\c1ccccc1)/CC)/c1cccc(c1)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(19-8-5-4-6-9-19)25(20-12-14-22(15-13-20)38-17-16-32-2)21-10-7-11-23(18-21)39-31-28(35)26(33)27(34)29(40-31)30(36)37/h4-15,18,26-29,31-35H,3,16-17H2,1-2H3,(H,36,37)/b25-24+/t26-,27-,28+,29-,31+/m0/s1
• InChIKey: BSCUKTJLQVNCRL-QXBBUDDSSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{3-[(1E)-1-{4-[2-(methylamino)ethoxy]phenyl}-2-phenylbut-1-en-1-yl]phenoxy}oxane-2-carboxylic acid
• IUPAC Traditional name: (2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{3-[(1E)-1-{4-[2-(methylamino)ethoxy]phenyl}-2-phenylbut-1-en-1-yl]phenoxy}oxane-2-carboxylic acid
• Synonyms: 3-[(1E)-1-[4-[2-(Methylamino)ethoxy]phenyl]-2-phenyl-1-buten-1-yl]phenyl β-D-Glucopyranosiduronic Acid; N-Desmethyl Droloxifene O-β-D-Glucuronide; 3-[(1E)-1-[4-[2-(Methylamino)ethoxy]phenyl]-2-phenyl-1-butenyl]phenyl β-D-Glucopyranosiduronic Acid; N-Desmethyl-3-hydroxy Tamoxifen O-β-D-Glucuronide

Database IDs

• CAS Number: 206440-83-7
• PubChem SID: 162260684
• PubChem CID: 71315770

CALCULATED PROPERTIES

• Acid pKa: 2.9532847
• H Acceptors: 9
• H Donor: 5
• LogD (pH = 5.5): 1.2443005
• LogD (pH = 7.4): 1.2422782
• Log P: 1.2449152
• Molar Refractivity: 157.1288 cm^3
• Polarizability: 58.57195 Å^3
• Polar Surface Area: 137.71 Å^2
• Rotatable Bonds: 11
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - D292250

N-Desmethyl 3-Hydroxy Tamoxifen O-β-D-Glucuronide is a metabolite of the non-steroidal anti-estrogen (E)-3-Hydroxytamoxifen (H954735).

REFERENCES

• John, B.A. et al.: Xenobiotica, 32, 699 (2002)
• O'Donnell, J.P. et al.: Xenobiotica, 28, 153 (2002)