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

• ChemBase ID: 171285
• Molecular Formular: C37H48N6O6S2
• Molecular Mass: 736.94362
• Monoisotopic Mass: 736.30767529
• SMILES: c1ncsc1COC(=O)N[C@H]([C@H](C[C@@H](NC(=O)[C@@H](NC(=O)N(Cc1nc(sc1)C(O)(C)C)C)C(C)C)Cc1ccccc1)O)Cc1ccccc1
• Canonical SMILES: O=C(N[C@H]([C@H](C[C@H](Cc1ccccc1)NC(=O)[C@H](C(C)C)NC(=O)N(Cc1csc(n1)C(O)(C)C)C)O)Cc1ccccc1)OCc1cncs1
• InChI: InChI=1S/C37H48N6O6S2/c1-24(2)32(42-35(46)43(5)20-28-22-50-34(40-28)37(3,4)48)33(45)39-27(16-25-12-8-6-9-13-25)18-31(44)30(17-26-14-10-7-11-15-26)41-36(47)49-21-29-19-38-23-51-29/h6-15,19,22-24,27,30-32,44,48H,16-18,20-21H2,1-5H3,(H,39,45)(H,41,47)(H,42,46)/t27-,30-,31-,32-/m0/s1
• InChIKey: CLEDZMPJHBBTNZ-QJANCWQKSA-N

NAMES AND DATABASE IDS

Names

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

Database IDs

• CAS Number: 176655-56-4
• PubChem SID: 164227195
• PubChem CID: 71749331

CALCULATED PROPERTIES

• Acid pKa: 13.180824
• H Acceptors: 7
• H Donor: 5
• LogD (pH = 5.5): 4.1624722
• LogD (pH = 7.4): 4.1625404
• Log P: 4.162542
• Molar Refractivity: 196.3004 cm^3
• Polarizability: 76.40607 Å^3
• Polar Surface Area: 166.01 Å^2
• Rotatable Bonds: 18
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - H953390

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

REFERENCES

• Eagling, V., et al.: Br. J. Clin. Pharmacol., 48, 543 (1999)
• Eagling, V., et al.: Xenobiotica, 32, 1 (1999)
• Meaden, E., et al.: J. Antimicrob. Chemother., 50, 583 (1999)
• Treijtel, N., et al.: Drug Metab. Dispos., 33, 1325 (1999)