(2S,3S,4S,5R,6S)-6-{[2-(4-{[(2S,3R,4S,5S,6S)-6-carboxy-3,4,5-trihydroxyoxan-2-yl]oxy}phenyl)-3-{4-[2-(piperidin-1-yl)ethoxy]benzoyl}-1-benzothiophen-6-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid

• ChemBase ID: 177246
• Molecular Formular: C40H43NO16S
• Molecular Mass: 825.83152
• Monoisotopic Mass: 825.2302553
• SMILES: c1c(ccc2c1sc(c2C(=O)c1ccc(cc1)OCCN1CCCCC1)c1ccc(cc1)O[C@H]1[C@@H]([C@@H]([C@@H]([C@H](O1)C(=O)O)O)O)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]2O[C@H](C(=O)O)[C@H]([C@H]([C@H]2O)O)O)[C@H]([C@H]([C@@H]1O)O)O
• InChI: InChI=1S/C40H43NO16S/c42-27(19-4-8-21(9-5-19)53-17-16-41-14-2-1-3-15-41)26-24-13-12-23(55-40-33(48)29(44)31(46)35(57-40)38(51)52)18-25(24)58-36(26)20-6-10-22(11-7-20)54-39-32(47)28(43)30(45)34(56-39)37(49)50/h4-13,18,28-35,39-40,43-48H,1-3,14-17H2,(H,49,50)(H,51,52)/t28-,29-,30-,31-,32+,33+,34-,35-,39+,40+/m0/s1
• InChIKey: PCIAOPAUTIPRHI-SLTHDDBBSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S,5R,6S)-6-{[2-(4-{[(2S,3R,4S,5S,6S)-6-carboxy-3,4,5-trihydroxyoxan-2-yl]oxy}phenyl)-3-{4-[2-(piperidin-1-yl)ethoxy]benzoyl}-1-benzothiophen-6-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
• IUPAC Traditional name: (2S,3S,4S,5R,6S)-6-{[2-(4-{[(2S,3R,4S,5S,6S)-6-carboxy-3,4,5-trihydroxyoxan-2-yl]oxy}phenyl)-3-{4-[2-(piperidin-1-yl)ethoxy]benzoyl}-1-benzothiophen-6-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
• Synonyms: 2-[4-(β-D-Glucopyranuronosyloxy)phenyl]-3-[4-[2-(1-piperidinyl)ethoxy]benzoyl]benzo[b]thien-6-yl β-D-Glucopyranosiduronic Acid; Raloxifene 6,4'-Bis-β-D-glucuronide

Database IDs

• CAS Number: 182507-20-6
• PubChem SID: 164233156
• PubChem CID: 71751917

CALCULATED PROPERTIES

• Acid pKa: 2.9798815
• H Acceptors: 17
• H Donor: 8
• LogD (pH = 5.5): -2.3515298
• LogD (pH = 7.4): -3.9458532
• Log P: -0.8344384
• Molar Refractivity: 199.5036 cm^3
• Polarizability: 81.76515 Å^3
• Polar Surface Area: 262.44 Å^2
• Rotatable Bonds: 13
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO; Water
• Apperance: Light Tan Solid
• Melting Point: >185°C (dec.)

Safety Information

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

DETAILS

Toronto Research Chemicals - R100005

A metabolite of Raloxifene.

REFERENCES

• Nakagawa, M., et al.: Antibiotics, 38, 1622 (1985)
• Chen, T., et al.: J. Antibiot., 46, 131 (1985)
• Dodge, J., et al.: Bioorg. Med. Chem. Lett., 7, 993 (1985)
• Marcus, R., et al.: Endocrine, 6, 207 (1985)