(2R,3R,4S,5S,6S)-6-carboxy-3,4,5-trihydroxy-N-(2-{4-[1-(4-hydroxyphenyl)-2-phenylbut-1-en-1-yl]phenoxy}ethyl)-N,N-dimethyloxan-2-aminium

• ChemBase ID: 171338
• Molecular Formular: C32H38NO8+
• Molecular Mass: 564.64602
• Monoisotopic Mass: 564.25974218
• SMILES: c1cc(ccc1O)/C(=C(/CC)\c1ccccc1)/c1ccc(cc1)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(/c1ccc(cc1)O)\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/C32H37NO8/c1-4-25(20-8-6-5-7-9-20)26(21-10-14-23(34)15-11-21)22-12-16-24(17-13-22)40-19-18-33(2,3)31-29(37)27(35)28(36)30(41-31)32(38)39/h5-17,27-31,35-37H,4,18-19H2,1-3H3,(H-,34,38,39)/p+1/t27-,28-,29+,30-,31+/m0/s1
• InChIKey: IAUNDDKJZIEYFB-XVEIJSAGSA-O

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3R,4S,5S,6S)-6-carboxy-3,4,5-trihydroxy-N-(2-{4-[1-(4-hydroxyphenyl)-2-phenylbut-1-en-1-yl]phenoxy}ethyl)-N,N-dimethyloxan-2-aminium
• IUPAC Traditional name: (2R,3R,4S,5S,6S)-6-carboxy-3,4,5-trihydroxy-N-(2-{4-[1-(4-hydroxyphenyl)-2-phenylbut-1-en-1-yl]phenoxy}ethyl)-N,N-dimethyloxan-2-aminium
• Synonyms: N-β-D-Glucopyranuronosyl-2-[4-[(1E/Z)-1-(4-hydroxyphenyl)-2-phenyl-1-butenyl]phenoxy]-N,N-dimethylethanaminium; 4-OH-TAM-N-Glucuronide; 4-Hydroxy Tamoxifen N-β-D-Glucuronide(E/Z-Mixture)

Database IDs

• PubChem SID: 164227248
• PubChem CID: 71749357

CALCULATED PROPERTIES

• Acid pKa: 3.1769638
• H Acceptors: 8
• H Donor: 5
• LogD (pH = 5.5): 0.5604
• LogD (pH = 7.4): 0.5573058
• Log P: -0.2083676
• Molar Refractivity: 173.8548 cm^3
• Polarizability: 60.281597 Å^3
• Polar Surface Area: 136.68 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Methanol; Water
• Apperance: White Solid
• Melting Point: 149-151°C (dec.)

Safety Information

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

DETAILS

Toronto Research Chemicals - H954740

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)