1,3-thiazol-5-ylmethyl N-[(2S,3S,5S)-5-[(4R)-2,5-dioxo-4-(propan-2-yl)imidazolidin-1-yl]-3-hydroxy-1,6-diphenylhexan-2-yl]carbamate

• ChemBase ID: 166327
• Molecular Formular: C29H34N4O5S
• Molecular Mass: 550.66906
• Monoisotopic Mass: 550.22499121
• SMILES: C(OC(=O)N[C@H]([C@H](C[C@H](Cc1ccccc1)N1C(=O)N[C@@H](C1=O)C(C)C)O)Cc1ccccc1)c1cncs1
• Canonical SMILES: O=C(N[C@H]([C@H](C[C@@H](N1C(=O)N[C@@H](C1=O)C(C)C)Cc1ccccc1)O)Cc1ccccc1)OCc1scnc1
• InChI: InChI=1S/C29H34N4O5S/c1-19(2)26-27(35)33(28(36)32-26)22(13-20-9-5-3-6-10-20)15-25(34)24(14-21-11-7-4-8-12-21)31-29(37)38-17-23-16-30-18-39-23/h3-12,16,18-19,22,24-26,34H,13-15,17H2,1-2H3,(H,31,37)(H,32,36)/t22-,24-,25-,26+/m0/s1
• InChIKey: CDGZDJUYEAMJKJ-ZCLKUGBOSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1,3-thiazol-5-ylmethyl N-[(2S,3S,5S)-5-[(4R)-2,5-dioxo-4-(propan-2-yl)imidazolidin-1-yl]-3-hydroxy-1,6-diphenylhexan-2-yl]carbamate
• IUPAC Traditional name: 1,3-thiazol-5-ylmethyl N-[(2S,3S,5S)-3-hydroxy-5-[(4R)-4-isopropyl-2,5-dioxoimidazolidin-1-yl]-1,6-diphenylhexan-2-yl]carbamate
• Synonyms: N-[(1S,2S,4S)-2-Hydroxy-4-[(4S)-4-(1-methylethyl)-2,5-dioxo-1-imidazolidinyl]-5-phenyl-1-(phenylmethyl)pentyl]carbamic Acid 5-Thiazolylmethyl Ester; 1,3-Thiazol-5-ylmethyl N-[(1S,2S,4S)-1-benzyl-2-hydroxy-4-((4S)-4-isopropyl-2,5-dioxoimidazolidin-1-yl)-5-phenylpentyl]carbamate; Thiazol-5-ylmethyl (2S,3S,5S)-3-hydroxy-5-[(S)-4-isorpopyl-2,5-dioxoimidazolidin-1-yl]-1,6-diphenylhexan-2-ylcarbamate; Des(isopropylthiazolyl) Hydantoin Ritonavir

Database IDs

• CAS Number: 1010809-61-6
• PubChem SID: 162260460
• PubChem CID: 71315689

CALCULATED PROPERTIES

• Acid pKa: 11.759284
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): 3.9619482
• LogD (pH = 7.4): 3.9619825
• Log P: 3.9620018
• Molar Refractivity: 146.9581 cm^3
• Polarizability: 57.318314 Å^3
• Polar Surface Area: 120.86 Å^2
• Rotatable Bonds: 13
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - D290215

Ritonavir (R535000) derivative with potential use in the treatment of viral infections. Cytochrome P450 oxidase inhibitor.

REFERENCES

• Daluge, S., et al.: Antimicrob. Agents Chemother., 38, 1590 (1994)
• Ammaranond, P., et al.: J. Clin. Virol., 26, 153 (1994)