(3R,4s,7S)-7-(4-chlorophenyl)-2-(4-fluorophenyl)-7-hydroxy-3-(4-hydroxyphenyl)-2-azaspiro[3.5]nonan-1-one

• ChemBase ID: 177646
• Molecular Formular: C26H23ClFNO3
• Molecular Mass: 451.9171232
• Monoisotopic Mass: 451.1350495
• SMILES: [C@@H]1(N(C(=O)[C@@]21CC[C@@](CC2)(c1ccc(cc1)Cl)O)c1ccc(cc1)F)c1ccc(cc1)O
• Canonical SMILES: Oc1ccc(cc1)[C@H]1N(c2ccc(cc2)F)C(=O)[C@@]21CC[C@](CC2)(O)c1ccc(cc1)Cl
• InChI: InChI=1S/C26H23ClFNO3/c27-19-5-3-18(4-6-19)26(32)15-13-25(14-16-26)23(17-1-11-22(30)12-2-17)29(24(25)31)21-9-7-20(28)8-10-21/h1-12,23,30,32H,13-16H2/t23-,25-,26+/m1/s1
• InChIKey: DPZUDTYEZMUJDW-ARMFNRFLSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3R,4s,7S)-7-(4-chlorophenyl)-2-(4-fluorophenyl)-7-hydroxy-3-(4-hydroxyphenyl)-2-azaspiro[3.5]nonan-1-one
• IUPAC Traditional name: (3R,4s,7S)-7-(4-chlorophenyl)-2-(4-fluorophenyl)-7-hydroxy-3-(4-hydroxyphenyl)-2-azaspiro[3.5]nonan-1-one
• Synonyms: (3R,4β,7α)-7-(4-Chlorophenyl)-2-(4-fluorophenyl)-7-hydroxy-3-(4-hydroxyphenyl)-2-azaspiro[3.5]nonan-1-one; Sch 58053

Database IDs

• CAS Number: 194423-53-5
• PubChem SID: 164233556
• PubChem CID: 9955498

CALCULATED PROPERTIES

• Acid pKa: 9.484055
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 5.471245
• LogD (pH = 7.4): 5.4677463
• Log P: 5.4712896
• Molar Refractivity: 120.7101 cm^3
• Polarizability: 46.73237 Å^3
• Polar Surface Area: 60.77 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO; Ethanol; Methanol
• Apperance: White Solid
• Melting Point: 211-213°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - S199950

An analog of Ezetimibe (E975000). SCH 58053 is a potent, rapid, and selective inhibitor of lymphatic cholesterol transport in the intestine.

REFERENCES

• Ly, H., et al.: Biochem. J., 286, 937 (1992)
• Dujovne, C., et al.: Am. J. Cardiol., 90, 1092 (1992)
• Repa, J., et al.: J. Lipid Res., 43, 1864 (1992)
• Knopp, R., et al.: Eur. Heart J., 24, 729 (1992)
• Altmann, S., et al.: Science, 303, 1201 (1992)