(2R,5S)-5-(4-fluorophenyl)-2-[(S)-[(4-fluorophenyl)amino](4-hydroxyphenyl)methyl]-5-hydroxypentanoic acid

• ChemBase ID: 168852
• Molecular Formular: C24H23F2NO4
• Molecular Mass: 427.4405264
• Monoisotopic Mass: 427.15951466
• SMILES: c1cc(ccc1[C@H](CC[C@@H](C(=O)O)[C@H](Nc1ccc(cc1)F)c1ccc(cc1)O)O)F
• Canonical SMILES: Oc1ccc(cc1)[C@H]([C@H](C(=O)O)CC[C@@H](c1ccc(cc1)F)O)Nc1ccc(cc1)F
• InChI: InChI=1S/C24H23F2NO4/c25-17-5-1-15(2-6-17)22(29)14-13-21(24(30)31)23(16-3-11-20(28)12-4-16)27-19-9-7-18(26)8-10-19/h1-12,21-23,27-29H,13-14H2,(H,30,31)/t21-,22+,23-/m1/s1
• InChIKey: XGNDFEVQHMNNOJ-XPWALMASSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,5S)-5-(4-fluorophenyl)-2-[(S)-[(4-fluorophenyl)amino](4-hydroxyphenyl)methyl]-5-hydroxypentanoic acid
• IUPAC Traditional name: (2R,5S)-5-(4-fluorophenyl)-2-[(S)-[(4-fluorophenyl)amino](4-hydroxyphenyl)methyl]-5-hydroxypentanoic acid
• Synonyms: Ezetimibe Azetidinone Ring-opened Impurity

Database IDs

• PubChem SID: 162262984
• PubChem CID: 71316706

CALCULATED PROPERTIES

• Acid pKa: 4.503345
• H Acceptors: 5
• H Donor: 4
• LogD (pH = 5.5): 3.5001647
• LogD (pH = 7.4): 1.7647492
• Log P: 4.345702
• Molar Refractivity: 113.7203 cm^3
• Polarizability: 42.798557 Å^3
• Polar Surface Area: 89.79 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - E975055

A degradation product of the antihyperlipoproteinemic Ezetimibe (E975000).