(2S)-N-[(2S,4S,5S)-5-amino-4-hydroxy-1,6-diphenylhexan-2-yl]-3-methyl-2-{[methyl({[2-(propan-2-yl)-1,3-thiazol-4-yl]methyl})carbamoyl]amino}butanamide

• ChemBase ID: 166679
• Molecular Formular: C32H45N5O3S
• Molecular Mass: 579.7964
• Monoisotopic Mass: 579.32431133
• SMILES: C(N(C(=O)N[C@H](C(=O)N[C@H](C[C@@H]([C@H](Cc1ccccc1)N)O)Cc1ccccc1)C(C)C)C)c1nc(sc1)C(C)C
• Canonical SMILES: CC([C@@H](C(=O)N[C@@H](Cc1ccccc1)C[C@@H]([C@H](Cc1ccccc1)N)O)NC(=O)N(Cc1csc(n1)C(C)C)C)C
• InChI: InChI=1S/C32H45N5O3S/c1-21(2)29(36-32(40)37(5)19-26-20-41-31(35-26)22(3)4)30(39)34-25(16-23-12-8-6-9-13-23)18-28(38)27(33)17-24-14-10-7-11-15-24/h6-15,20-22,25,27-29,38H,16-19,33H2,1-5H3,(H,34,39)(H,36,40)/t25-,27-,28-,29-/m0/s1
• InChIKey: IQKWCORIMSRQGZ-AMEOFWRWSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-N-[(2S,4S,5S)-5-amino-4-hydroxy-1,6-diphenylhexan-2-yl]-3-methyl-2-{[methyl({[2-(propan-2-yl)-1,3-thiazol-4-yl]methyl})carbamoyl]amino}butanamide
• IUPAC Traditional name: (2S)-N-[(2S,4S,5S)-5-amino-4-hydroxy-1,6-diphenylhexan-2-yl]-2-({[(2-isopropyl-1,3-thiazol-4-yl)methyl](methyl)carbamoyl}amino)-3-methylbutanamide
• Synonyms: (2S)-N-[(1S,3S,4S)-4-Amino-3-hydroxy-5-phenyl-1-(phenylmethyl)pentyl]-3-methyl-2-[[[methyl[[2-(1-methylethyl)-4-thiazolyl]methyl]amino]carbonyl]amino]butanamide; Desthiazolylmethyloxycarbonyl Ritonavir

Database IDs

• CAS Number: 176655-55-3
• PubChem SID: 162260812
• PubChem CID: 11467322

CALCULATED PROPERTIES

• Acid pKa: 14.284519
• H Acceptors: 5
• H Donor: 4
• LogD (pH = 5.5): 1.3269794
• LogD (pH = 7.4): 2.5268452
• Log P: 4.267939
• Molar Refractivity: 163.9199 cm^3
• Polarizability: 64.135376 Å^3
• Polar Surface Area: 120.58 Å^2
• Rotatable Bonds: 14
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Acetone; Chloroform; Dichloromethane; DMSO; Tetrahydrofuran
• Apperance: Off-White Solid
• Melting Point: 73-74°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - D297430

A labelled metabolite of the selective HIV protease inhibitor Ritonavir (R535000).

REFERENCES

• Jaworski, T., et al.: Xenobiotica, 21, 1451 (1991)
• Lee, S., et al.: Biochem. Pharmacol., 49, 1567 (1991)
• Zhang, X., et al.: Drug Metab. Dispos., 24, 23 (1991)