(3S)-(2,2,5,5-2H4)oxolan-3-yl N-[(2S,3R)-4-(N-tert-butyl4-aminobenzenesulfonamido)-3-hydroxy-1-phenylbutan-2-yl]carbamate

• ChemBase ID: 160596
• Molecular Formular: C25H35N3O6S
• Molecular Mass: 505.6269
• Monoisotopic Mass: 505.22465686
• SMILES: C1C[C@@H](CO1)OC(=O)N[C@@H](Cc1ccccc1)[C@H](O)CN(C(C)(C)C)S(=O)(=O)c1ccc(cc1)N
• Canonical SMILES: O=C(N[C@H]([C@@H](CN(S(=O)(=O)c1ccc(cc1)N)C(C)(C)C)O)Cc1ccccc1)O[C@H]1CCOC1
• InChI: InChI=1S/C25H35N3O6S/c1-25(2,3)28(35(31,32)21-11-9-19(26)10-12-21)16-23(29)22(15-18-7-5-4-6-8-18)27-24(30)34-20-13-14-33-17-20/h4-12,20,22-23,29H,13-17,26H2,1-3H3,(H,27,30)/t20-,22-,23+/m0/s1
• InChIKey: XRIXPKUVGAADME-ACIOBRDBSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3S)-(2,2,5,5-^2H₄)oxolan-3-yl N-[(2S,3R)-4-(N-tert-butyl4-aminobenzenesulfonamido)-3-hydroxy-1-phenylbutan-2-yl]carbamate
• IUPAC Traditional name: (3S)-(2,2,5,5-^2H₄)oxolan-3-yl N-[(2S,3R)-4-(N-tert-butyl4-aminobenzenesulfonamido)-3-hydroxy-1-phenylbutan-2-yl]carbamate
• Synonyms: 141W94-d4; KVX-478-d4; Agenerase-d4; Prozei-d4; Amprenavir-d4

Database IDs

• PubChem SID: 162254731
• PubChem CID: 46780384

CALCULATED PROPERTIES

• Acid pKa: 13.613749
• H Acceptors: 6
• H Donor: 3
• LogD (pH = 5.5): 2.2362816
• LogD (pH = 7.4): 2.2366047
• Log P: 2.2366092
• Molar Refractivity: 134.1429 cm^3
• Polarizability: 52.79802 Å^3
• Polar Surface Area: 131.19 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Acetone; Chloroform; Dichloromethane; Ethyl Acetate; Methanol
• Apperance: Off-White to Pale Yellow Solid
• Melting Point: 78-80°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - A634402

Labelled Amprenavir, a selective HIV protease inhibitor. An analogue of Ritonavir.

REFERENCES

• Adkins, J.C., et al.: Drugs, 55, 837 (1998)