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

• ChemBase ID: 177326
• Molecular Formular: C34H35NO10S
• Molecular Mass: 649.7074
• Monoisotopic Mass: 649.19816733
• SMILES: c1c(ccc2c1sc(c2C(=O)c1ccc(cc1)OCCN1CCCCC1)c1ccc(cc1)O[C@H]1O[C@@H]([C@@H]([C@H]([C@H]1O)O)O)C(=O)O)O
• Canonical SMILES: Oc1ccc2c(c1)sc(c2C(=O)c1ccc(cc1)OCCN1CCCCC1)c1ccc(cc1)O[C@H]1O[C@H](C(=O)O)[C@@H]([C@H]([C@H]1O)O)O
• InChI: InChI=1S/C34H35NO10S/c36-21-8-13-24-25(18-21)46-32(20-6-11-23(12-7-20)44-34-30(40)28(38)29(39)31(45-34)33(41)42)26(24)27(37)19-4-9-22(10-5-19)43-17-16-35-14-2-1-3-15-35/h4-13,18,28-31,34,36,38-40H,1-3,14-17H2,(H,41,42)/t28-,29-,30+,31-,34+/m1/s1
• InChIKey: VHXYPEXOSLGZKH-WVXFORMLSA-N

NAMES AND DATABASE IDS

Names

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

Database IDs

• CAS Number: 182507-22-8
• PubChem SID: 164233236
• PubChem CID: 10372066

CALCULATED PROPERTIES

• Acid pKa: 3.1002958
• H Acceptors: 11
• H Donor: 5
• LogD (pH = 5.5): 1.3783503
• LogD (pH = 7.4): 1.2982998
• Log P: 1.3768045
• Molar Refractivity: 167.4918 cm^3
• Polarizability: 68.149414 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: 209-213°C (dec.)

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - R100020

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)