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

• ChemBase ID: 171337
• Molecular Formular: C32H37NO8
• Molecular Mass: 563.63808
• Monoisotopic Mass: 563.25191715
• SMILES: c1(cc(ccc1)/C(=C(\CC)/c1ccccc1)/c1ccc(cc1)OCCN(C)C)O[C@@H]1O[C@H]([C@H]([C@@H]([C@@H]1O)O)O)C(=O)O
• Canonical SMILES: CC/C(=C(\c1cccc(c1)O[C@@H]1O[C@@H](C(=O)O)[C@H]([C@@H]([C@@H]1O)O)O)/c1ccc(cc1)OCCN(C)C)/c1ccccc1
• InChI: InChI=1S/C32H37NO8/c1-4-25(20-9-6-5-7-10-20)26(21-13-15-23(16-14-21)39-18-17-33(2)3)22-11-8-12-24(19-22)40-32-29(36)27(34)28(35)30(41-32)31(37)38/h5-16,19,27-30,32,34-36H,4,17-18H2,1-3H3,(H,37,38)/b26-25+/t27-,28-,29+,30-,32+/m0/s1
• InChIKey: LLJQVSGWCSTGGW-OFKVRPASSA-N

NAMES AND DATABASE IDS

Names

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

Database IDs

• CAS Number: 165460-33-3
• PubChem SID: 164227247
• PubChem CID: 71749356

CALCULATED PROPERTIES

• Acid pKa: 2.9532833
• H Acceptors: 9
• H Donor: 4
• LogD (pH = 5.5): 1.3681417
• LogD (pH = 7.4): 1.3539338
• Log P: 1.368411
• Molar Refractivity: 162.4235 cm^3
• Polarizability: 60.4107 Å^3
• Polar Surface Area: 128.92 Å^2
• Rotatable Bonds: 11
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - H954735

(E)-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)
• Lien, E.A. et al.: Therap. Drug Mon., 17, 259 (2002)