1,3-thiazol-5-ylmethyl N-[(2S,3S,5S)-5-acetamido-3-hydroxy-1,6-diphenylhexan-2-yl]carbamate

• ChemBase ID: 178523
• Molecular Formular: C25H29N3O4S
• Molecular Mass: 467.58046
• Monoisotopic Mass: 467.18787742
• SMILES: c1sc(cn1)COC(=O)N[C@H]([C@H](C[C@@H](NC(=O)C)Cc1ccccc1)O)Cc1ccccc1
• Canonical SMILES: CC(=O)N[C@@H](Cc1ccccc1)C[C@@H]([C@H](Cc1ccccc1)NC(=O)OCc1cncs1)O
• InChI: InChI=1S/C25H29N3O4S/c1-18(29)27-21(12-19-8-4-2-5-9-19)14-24(30)23(13-20-10-6-3-7-11-20)28-25(31)32-16-22-15-26-17-33-22/h2-11,15,17,21,23-24,30H,12-14,16H2,1H3,(H,27,29)(H,28,31)/t21-,23-,24-/m0/s1
• InChIKey: LGKRKMCCXYIVTI-XWGVYQGASA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1,3-thiazol-5-ylmethyl N-[(2S,3S,5S)-5-acetamido-3-hydroxy-1,6-diphenylhexan-2-yl]carbamate
• IUPAC Traditional name: 1,3-thiazol-5-ylmethyl N-[(2S,3S,5S)-5-acetamido-3-hydroxy-1,6-diphenylhexan-2-yl]carbamate
• Synonyms: Thiazol-5-ylmethyl N-[(2S,3S,5S)-5-Acetamido-3-hydroxy-1,6-diphenylhexan-2-yl Carbamate; Ritonavir USP Impurity A; N-[(1S,2S,4S)-4-(Acetylamino)-2-hydroxy-5-phenyl-1-(phenylmethyl)pentyl]carbamic Acid 5-Thiazolylmethyl Ester; 1,3-Thiazol-5-ylmethyl N-[(1S,2S,4S)-4-(acetylamino)-1-benzyl-2-hydroxy-5-phenylpentyl]carbamate

Database IDs

• CAS Number: 1010808-43-1
• PubChem SID: 164234433
• PubChem CID: 71752515

CALCULATED PROPERTIES

• Acid pKa: 13.753328
• H Acceptors: 4
• H Donor: 3
• LogD (pH = 5.5): 2.9256206
• LogD (pH = 7.4): 2.9256737
• Log P: 2.9256747
• Molar Refractivity: 126.8884 cm^3
• Polarizability: 49.44841 Å^3
• Polar Surface Area: 100.55 Å^2
• Rotatable Bonds: 12
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - T344290

1,3-Thiazol-5-ylmethyl N-[(1S,2S,4S)-4-(acetylamino)-1-benzyl-2-hydroxy-5-phenylpentyl]carbamate is an impurity of the selective HIV protease inhibitor Ritonavir (R535000).