(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{[2-(4-hydroxyphenyl)-3-{4-[2-(piperidin-1-yl)ethoxy]benzoyl}-1-benzothiophen-6-yl]oxy}oxane-2-carboxylic acid

• ChemBase ID: 177328
• Molecular Formular: C34H35NO10S
• Molecular Mass: 649.7074
• Monoisotopic Mass: 649.19816733
• SMILES: c1c(ccc2c1sc(c2C(=O)c1ccc(cc1)OCCN1CCCCC1)c1ccc(cc1)O)O[C@@H]1O[C@H]([C@H]([C@@H]([C@@H]1O)O)O)C(=O)O
• Canonical SMILES: OC(=O)[C@@H]1O[C@@H](Oc2ccc3c(c2)sc(c3C(=O)c2ccc(cc2)OCCN2CCCCC2)c2ccc(cc2)O)[C@H]([C@H]([C@@H]1O)O)O
• InChI: InChI=1S/C34H35NO10S/c36-21-8-4-20(5-9-21)32-26(27(37)19-6-10-22(11-7-19)43-17-16-35-14-2-1-3-15-35)24-13-12-23(18-25(24)46-32)44-34-30(40)28(38)29(39)31(45-34)33(41)42/h4-13,18,28-31,34,36,38-40H,1-3,14-17H2,(H,41,42)/t28-,29-,30+,31-,34+/m0/s1
• InChIKey: MZPMSLSINDGEPM-WKRHDJAJSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{[2-(4-hydroxyphenyl)-3-{4-[2-(piperidin-1-yl)ethoxy]benzoyl}-1-benzothiophen-6-yl]oxy}oxane-2-carboxylic acid
• IUPAC Traditional name: (2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{[2-(4-hydroxyphenyl)-3-{4-[2-(piperidin-1-yl)ethoxy]benzoyl}-1-benzothiophen-6-yl]oxy}oxane-2-carboxylic acid
• Synonyms: 2-(4-Hydroxyphenyl)-3-[4-[2-(1-piperidinyl)ethoxybenzoyl]benzo[b]thien-6-yl]-β-D-glucopyranosiduronic Acid; Raloxifene 6-Glucuronide

Database IDs

• CAS Number: 174264-50-7
• PubChem SID: 164233238
• PubChem CID: 10100752

CALCULATED PROPERTIES

• Acid pKa: 3.596919
• H Acceptors: 11
• H Donor: 5
• LogD (pH = 5.5): 1.3812588
• LogD (pH = 7.4): 1.2974415
• Log P: 1.3816078
• Molar Refractivity: 167.4918 cm^3
• Polarizability: 68.150566 Å^3
• Polar Surface Area: 166.22 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMF; DMSO; Hot Methanol
• Apperance: Yellow Solid
• Melting Point: >180°C (dec.)

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - R100025

A metabolite of Raloxifene, a nonsteroidal estrogen receptor mixed agonist/antagonist.

REFERENCES

• Dodge, J., et al.: Bioorg. Med. Chem. Lett., 7, 993 (1997)
• Jeong, E., et al.: Drug Metab. Dispos., 33, 785 (1997)
• Trontelj, J., et al.: Pharmacol. Res., 52, 334 (1997)
• Oswald, S., et al.: Clin. Pharmacol. Ther., 79 206 (1997)