(2S)-N-[(2S)-1-[(4S,5S)-4-benzyl-2-oxo-1,3-oxazolidin-5-yl]-3-phenylpropan-2-yl]-3-methyl-2-{[methyl({[2-(propan-2-yl)-1,3-thiazol-4-yl]methyl})carbamoyl]amino}butanamide

• ChemBase ID: 166681
• Molecular Formular: C33H43N5O4S
• Molecular Mass: 605.79062
• Monoisotopic Mass: 605.30357588
• SMILES: s1c(nc(c1)CN(C(=O)N[C@H](C(=O)N[C@H](C[C@@H]1OC(=O)N[C@H]1Cc1ccccc1)Cc1ccccc1)C(C)C)C)C(C)C
• Canonical SMILES: O=C1N[C@H]([C@@H](O1)C[C@H](Cc1ccccc1)NC(=O)[C@H](C(C)C)NC(=O)N(Cc1csc(n1)C(C)C)C)Cc1ccccc1
• InChI: InChI=1S/C33H43N5O4S/c1-21(2)29(37-32(40)38(5)19-26-20-43-31(35-26)22(3)4)30(39)34-25(16-23-12-8-6-9-13-23)18-28-27(36-33(41)42-28)17-24-14-10-7-11-15-24/h6-15,20-22,25,27-29H,16-19H2,1-5H3,(H,34,39)(H,36,41)(H,37,40)/t25-,27-,28-,29-/m0/s1
• InChIKey: YIFUFODEQQNFLV-AMEOFWRWSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-N-[(2S)-1-[(4S,5S)-4-benzyl-2-oxo-1,3-oxazolidin-5-yl]-3-phenylpropan-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)-1-[(4S,5S)-4-benzyl-2-oxo-1,3-oxazolidin-5-yl]-3-phenylpropan-2-yl]-2-({[(2-isopropyl-1,3-thiazol-4-yl)methyl](methyl)carbamoyl}amino)-3-methylbutanamide
• Synonyms: (2S)-3-Methyl-2-[[[methyl[[2-(1-methylethyl)-4-thiazolyl]methyl]amino]carbonyl]amino]-N-[(1S)-1-[[(4S,5S)-2-oxo-4-(phenylmethyl)-5-oxazolidinyl]methyl]-2-phenylethyl]-butanamide; Desthiazolylmethyl Ritonavir

Database IDs

• CAS Number: 256328-82-2
• PubChem SID: 162260814
• PubChem CID: 45038913

CALCULATED PROPERTIES

• Acid pKa: 12.955525
• H Acceptors: 4
• H Donor: 3
• LogD (pH = 5.5): 5.2240605
• LogD (pH = 7.4): 5.224645
• Log P: 5.2246537
• Molar Refractivity: 166.726 cm^3
• Polarizability: 65.09245 Å^3
• Polar Surface Area: 112.66 Å^2
• Rotatable Bonds: 13
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Chloroform; DMSO; Methanol
• Apperance: White Solid
• Melting Point: 65-69°C

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - D297450

An analogue of the selective HIV protease inhibitor Ritonavir (R535000).

REFERENCES

• Brittain, H., et al.: Pharm. Res., 8, 963 (1991)
• Sham, H., et al.: J. Med. Chem., 39, 392 (1991)
• Phadnis, N., et al.: J. Pharm. Sci.,86, 1256 (1991)
• Bauer, J., et al.: Pharma. Res., 18, 859 (1991)