(2R,5S)-N,5-bis(4-fluorophenyl)-5-hydroxy-2-[(4-hydroxyphenyl)methyl]pentanamide

• ChemBase ID: 170146
• Molecular Formular: C24H23F2NO3
• Molecular Mass: 411.4411264
• Monoisotopic Mass: 411.16460004
• SMILES: c1cc(ccc1[C@H](CC[C@@H](C(=O)Nc1ccc(cc1)F)Cc1ccc(cc1)O)O)F
• Canonical SMILES: Oc1ccc(cc1)C[C@H](C(=O)Nc1ccc(cc1)F)CC[C@@H](c1ccc(cc1)F)O
• InChI: InChI=1S/C24H23F2NO3/c25-19-6-3-17(4-7-19)23(29)14-5-18(15-16-1-12-22(28)13-2-16)24(30)27-21-10-8-20(26)9-11-21/h1-4,6-13,18,23,28-29H,5,14-15H2,(H,27,30)/t18-,23+/m1/s1
• InChIKey: CJMGACWDXHCPAC-JPYJTQIMSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,5S)-N,5-bis(4-fluorophenyl)-5-hydroxy-2-[(4-hydroxyphenyl)methyl]pentanamide
• IUPAC Traditional name: (2R,5S)-N,5-bis(4-fluorophenyl)-5-hydroxy-2-[(4-hydroxyphenyl)methyl]pentanamide
• Synonyms: (αR,δS)-4-Fluoro-N-(4-fluorophenyl)-δ-hydroxy-α-[(4-hydroxyphenyl)methyl]benzenepentanamide; 2-(4-Hydroxybenzyl)-N,5-bis-(4-fluorophenyl)-5-hydroxypentanamide

Database IDs

• CAS Number: 1197811-72-5
• PubChem SID: 164226056
• PubChem CID: 58284448

CALCULATED PROPERTIES

• Acid pKa: 9.505022
• H Acceptors: 3
• H Donor: 3
• LogD (pH = 5.5): 5.2513456
• LogD (pH = 7.4): 5.2480116
• Log P: 5.2513885
• Molar Refractivity: 112.6456 cm^3
• Polarizability: 42.308964 Å^3
• Polar Surface Area: 69.56 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - H809740

2-(4-Hydroxybenzyl)-N,5-bis-(4-fluorophenyl)-5-hydroxypentanamide is an ring-opened impurity of Ezetimibe (E975000).

REFERENCES

• Raman, B. et al.: J. Pharmac. Biomed. Anal., 52, 73 (2010)