1,3-thiazol-5-ylmethyl N-[(2S,3S,5S)-3-hydroxy-5-[(2S)-3-methyl-2-[(methylcarbamoyl)amino]butanamido]-1,6-diphenylhexan-2-yl]carbamate

• ChemBase ID: 166326
• Molecular Formular: C30H39N5O5S
• Molecular Mass: 581.72616
• Monoisotopic Mass: 581.26719037
• 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)NC
• Canonical SMILES: CNC(=O)N[C@H](C(=O)N[C@H](C[C@@H]([C@H](Cc1ccccc1)NC(=O)OCc1scnc1)O)Cc1ccccc1)C(C)C
• InChI: InChI=1S/C30H39N5O5S/c1-20(2)27(35-29(38)31-3)28(37)33-23(14-21-10-6-4-7-11-21)16-26(36)25(15-22-12-8-5-9-13-22)34-30(39)40-18-24-17-32-19-41-24/h4-13,17,19-20,23,25-27,36H,14-16,18H2,1-3H3,(H,33,37)(H,34,39)(H2,31,35,38)/t23-,25-,26-,27-/m0/s1
• InChIKey: UVQJGJZZUNOHCX-MNUOIFNESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1,3-thiazol-5-ylmethyl N-[(2S,3S,5S)-3-hydroxy-5-[(2S)-3-methyl-2-[(methylcarbamoyl)amino]butanamido]-1,6-diphenylhexan-2-yl]carbamate
• IUPAC Traditional name: 1,3-thiazol-5-ylmethyl N-[(2S,3S,5S)-3-hydroxy-5-[(2S)-3-methyl-2-[(methylcarbamoyl)amino]butanamido]-1,6-diphenylhexan-2-yl]carbamate
• Synonyms: (3S,4S,6S,9S)-4-Hydroxy-9-(1-methylethyl)-8,11-dioxo-3,6-bis(phenylmethyl)-2,7,10,12-tetraazatridecanoic Acid 5-Thiazolylmethyl Ester; Des(isopropylthiazolyl) Ritonavir

Database IDs

• CAS Number: 176655-57-5
• PubChem SID: 162260459
• PubChem CID: 66832582

CALCULATED PROPERTIES

• Acid pKa: 13.705565
• H Acceptors: 5
• H Donor: 5
• LogD (pH = 5.5): 3.1667278
• LogD (pH = 7.4): 3.1667805
• Log P: 3.1667814
• Molar Refractivity: 156.7548 cm^3
• Polarizability: 61.022823 Å^3
• Polar Surface Area: 141.68 Å^2
• Rotatable Bonds: 15
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - D290210

A metabolite of Ritonavir (R535000), an orally active HIV-1 protease inhibitor.

REFERENCES

• Jaworski, T., et al.: Xenobiotica, 21, 1451 (1991)
• Balani, S., et al.: Drug Metab. Dispos., 23, 185 (1991)
• Lee, S., et al.: Biochem. Pharmacol., 49, 1567 (1991)