1,3-thiazol-5-ylmethyl N-[(2S,4S,5S)-4-hydroxy-5-[(2S)-3-methyl-2-{[methyl({[2-(propan-2-yl)-1,3-thiazol-4-yl]methyl})carbamoyl]amino}butanamido]-1,6-diphenylhexan-2-yl]carbamate

• ChemBase ID: 165723
• Molecular Formular: C37H48N6O5S2
• Molecular Mass: 720.94422
• Monoisotopic Mass: 720.31276067
• SMILES: n1csc(c1)COC(=O)N[C@@H](Cc1ccccc1)C[C@@H]([C@H](Cc1ccccc1)NC(=O)[C@H](C(C)C)NC(=O)N(Cc1nc(sc1)C(C)C)C)O
• Canonical SMILES: O=C(N[C@@H](Cc1ccccc1)C[C@@H]([C@H](Cc1ccccc1)NC(=O)[C@H](C(C)C)NC(=O)N(Cc1csc(n1)C(C)C)C)O)OCc1cncs1
• InChI: InChI=1S/C37H48N6O5S2/c1-24(2)33(42-36(46)43(5)20-29-22-49-35(39-29)25(3)4)34(45)41-31(17-27-14-10-7-11-15-27)32(44)18-28(16-26-12-8-6-9-13-26)40-37(47)48-21-30-19-38-23-50-30/h6-15,19,22-25,28,31-33,44H,16-18,20-21H2,1-5H3,(H,40,47)(H,41,45)(H,42,46)/t28-,31-,32-,33-/m0/s1
• InChIKey: VRNXMJYSOAQBMK-XGKFQTDJSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1,3-thiazol-5-ylmethyl N-[(2S,4S,5S)-4-hydroxy-5-[(2S)-3-methyl-2-{[methyl({[2-(propan-2-yl)-1,3-thiazol-4-yl]methyl})carbamoyl]amino}butanamido]-1,6-diphenylhexan-2-yl]carbamate
• IUPAC Traditional name: 1,3-thiazol-5-ylmethyl N-[(2S,4S,5S)-4-hydroxy-5-[(2S)-2-({[(2-isopropyl-1,3-thiazol-4-yl)methyl](methyl)carbamoyl}amino)-3-methylbutanamido]-1,6-diphenylhexan-2-yl]carbamate
• Synonyms: (3S,5S,6S,9S)-5-Hydroxy-12-methyl-9-(1-methylethyl)-13-[2-(1-methylethyl)-4-thiazolyl]-8,11-dioxo-3,6-bis(phenylmethyl)-2,7,10,12-tetraazatridecanoic Acid 5-Thiazolylmethyl Ester; Ritonavir Impurity I; (5S,8S,9S,11S)-9-Hydroxy-2-methyl-5-(1-methylethyl)-1-[2-(1-methylethyl)-4-thiazolyl]-3,6-dioxo-8,11-bis(phenylmethyl)-2,4,7,12-tetraazatridecan-13-oic Acid 5-Thiazolylmethyl Ester; 4-Dehydroxy-5-hydroxy Ritonavir

Database IDs

• CAS Number: 202816-62-4
• PubChem SID: 162259856
• PubChem CID: 515815

CALCULATED PROPERTIES

• Acid pKa: 13.31851
• H Acceptors: 6
• H Donor: 4
• LogD (pH = 5.5): 5.221135
• LogD (pH = 7.4): 5.2217736
• Log P: 5.221782
• Molar Refractivity: 194.5924 cm^3
• Polarizability: 75.68044 Å^3
• Polar Surface Area: 145.78 Å^2
• Rotatable Bonds: 18
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - D230645

4-Dehydroxy-5-Hydroxy Ritonavir is an impurity of the selective HIV protease inhibitor Ritonavir (R535000).

REFERENCES

• Kempf, D.J. et al.: J. Med. Chem., 41, 602 (1998)
• Mekapati, S.B. et al.: J. Enzyme Inhib., 16, 185 (1998)