1,3-thiazol-5-ylmethyl (4S,5S)-4-benzyl-5-[(2S)-2-[(4R)-2,5-dioxo-4-(propan-2-yl)imidazolidin-1-yl]-3-phenylpropyl]-2-oxo-1,3-oxazolidine-3-carboxylate

• ChemBase ID: 166325
• Molecular Formular: C30H32N4O6S
• Molecular Mass: 576.66328
• Monoisotopic Mass: 576.20425576
• SMILES: C(OC(=O)N1C(=O)O[C@H]([C@@H]1Cc1ccccc1)C[C@H](Cc1ccccc1)N1C(=O)N[C@@H](C1=O)C(C)C)c1cncs1
• Canonical SMILES: O=C(N1C(=O)O[C@H]([C@@H]1Cc1ccccc1)C[C@@H](N1C(=O)N[C@@H](C1=O)C(C)C)Cc1ccccc1)OCc1scnc1
• InChI: InChI=1S/C30H32N4O6S/c1-19(2)26-27(35)33(28(36)32-26)22(13-20-9-5-3-6-10-20)15-25-24(14-21-11-7-4-8-12-21)34(30(38)40-25)29(37)39-17-23-16-31-18-41-23/h3-12,16,18-19,22,24-26H,13-15,17H2,1-2H3,(H,32,36)/t22-,24-,25-,26+/m0/s1
• InChIKey: LCTIJBMKZTVMSG-ZCLKUGBOSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1,3-thiazol-5-ylmethyl (4S,5S)-4-benzyl-5-[(2S)-2-[(4R)-2,5-dioxo-4-(propan-2-yl)imidazolidin-1-yl]-3-phenylpropyl]-2-oxo-1,3-oxazolidine-3-carboxylate
• IUPAC Traditional name: 1,3-thiazol-5-ylmethyl (4S,5S)-4-benzyl-5-[(2S)-2-[(4R)-4-isopropyl-2,5-dioxoimidazolidin-1-yl]-3-phenylpropyl]-2-oxo-1,3-oxazolidine-3-carboxylate
• Synonyms: (4S,5S)-4-Benzyl-5-[(2S)-2-((4S)-4-isopropyl-2,5-dioxoimidazolidin-1-yl)-3-phenylpropyl]-2-oxo-1,3-oxazolidine-3-carboxylate thiazol-5-ylmethyl Ester; , (4S,5S)-5-[(2S)-2-[(4S)-4-(1-methylethyl)-2,5-dioxo-1-imidazolidinyl]-3-phenylpropyl]-2-oxo-4-(phenylmethyl)-3-oxazolidinecarboxylic Acid 5-Thiazolylmethyl Ester; (4S,5S)-Thiazol-5-ylmethyl 4-Benzyl-5-[(S)-2-[(s)-4-isopropyl-2,5-dioxoimidazolidin-1-yl]-3-phenylpropyl]-2-oxooxazolidne-3-carboxylate; Des(isopropylthiazolyl) Hydantoin-oxazolidinone Ritonavir

Database IDs

• CAS Number: 1010809-43-4
• PubChem SID: 162260458
• PubChem CID: 71315688

CALCULATED PROPERTIES

• Acid pKa: 11.613547
• H Acceptors: 5
• H Donor: 1
• LogD (pH = 5.5): 5.0884247
• LogD (pH = 7.4): 5.0884514
• Log P: 5.0884786
• Molar Refractivity: 149.8863 cm^3
• Polarizability: 58.611202 Å^3
• Polar Surface Area: 118.14 Å^2
• Rotatable Bonds: 11
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - D290205

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)