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

• ChemBase ID: 166337
• Molecular Formular: C36H46N6O5S2
• Molecular Mass: 706.91764
• Monoisotopic Mass: 706.2971106
• SMILES: n1csc(c1)COC(=O)N[C@@H](Cc1ccccc1)[C@@H](O)C[C@H](Cc1ccccc1)NC(=O)[C@H](C(C)C)NC(=O)N(Cc1nc(sc1)CC)C
• Canonical SMILES: CCc1scc(n1)CN(C(=O)N[C@H](C(=O)N[C@@H](Cc1ccccc1)C[C@@H]([C@H](Cc1ccccc1)NC(=O)OCc1cncs1)O)C(C)C)C
• InChI: InChI=1S/C36H46N6O5S2/c1-5-32-38-28(22-48-32)20-42(4)35(45)41-33(24(2)3)34(44)39-27(16-25-12-8-6-9-13-25)18-31(43)30(17-26-14-10-7-11-15-26)40-36(46)47-21-29-19-37-23-49-29/h6-15,19,22-24,27,30-31,33,43H,5,16-18,20-21H2,1-4H3,(H,39,44)(H,40,46)(H,41,45)/t27-,30-,31-,33-/m0/s1
• InChIKey: OYEPOHCIXAAUDI-UDRKEFQJSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1,3-thiazol-5-ylmethyl N-[(2S,3S,5S)-5-[(2S)-2-({[(2-ethyl-1,3-thiazol-4-yl)methyl](methyl)carbamoyl}amino)-3-methylbutanamido]-3-hydroxy-1,6-diphenylhexan-2-yl]carbamate
• IUPAC Traditional name: 1,3-thiazol-5-ylmethyl N-[(2S,3S,5S)-5-[(2S)-2-({[(2-ethyl-1,3-thiazol-4-yl)methyl](methyl)carbamoyl}amino)-3-methylbutanamido]-3-hydroxy-1,6-diphenylhexan-2-yl]carbamate
• Synonyms: (5S,8S,10S,11S)-1-(2-Ethyl-4-thiazolyl)-10-hydroxy-2-methyl-5-(1-methylethyl)-3,6-dioxo-8,11-bis(phenylmethyl)-2,4,7,12-tetraazatridecan-13-oic Acid 5-Thiazolylmethyl Ester; Ritonavir USP Impurity F; [5S-(5R*,8R*,10R*,11R*)]-1-(2-Ethyl-4-thiazolyl)-10-hydroxy-2-methyl-5-(1-methylethyl)-3,6-dioxo-8,11-bis(phenylmethyl)-2,4,7,12-tetraazatridecan-13-oic Acid 5-Thiazolylmethyl Ester; 2-Desisopropyl-2-ethyl Ritonavir

Database IDs

• CAS Number: 165315-26-4
• PubChem SID: 162260470
• PubChem CID: 482956

CALCULATED PROPERTIES

• Acid pKa: 13.675409
• H Acceptors: 6
• H Donor: 4
• LogD (pH = 5.5): 4.67798
• LogD (pH = 7.4): 4.6787853
• Log P: 4.678796
• Molar Refractivity: 190.0179 cm^3
• Polarizability: 73.84419 Å^3
• Polar Surface Area: 145.78 Å^2
• Rotatable Bonds: 18
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - D290245

2-Desisopropyl-2-ethyl 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)