(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl N-[(2S,3R)-3-hydroxy-4-[N-(2-methylpropyl)4-aminobenzenesulfonamido]-1-phenylbutan-2-yl]carbamate; ethanol

• ChemBase ID: 312876
• Molecular Formular: C29H43N3O8S
• Molecular Mass: 593.73202
• Monoisotopic Mass: 593.27708635
• SMILES: [C@H]12[C@H]([C@H](CO1)OC(=O)N[C@@H](Cc1ccccc1)[C@@H](CN(CC(C)C)S(=O)(=O)c1ccc(cc1)N)O)CCO2.CCO
• Canonical SMILES: CC(CN(S(=O)(=O)c1ccc(cc1)N)C[C@H]([C@H](Cc1ccccc1)NC(=O)O[C@H]1CO[C@@H]2[C@H]1CCO2)O)C.CCO
• InChI: InChI=1S/C27H37N3O7S.C2H6O/c1-18(2)15-30(38(33,34)21-10-8-20(28)9-11-21)16-24(31)23(14-19-6-4-3-5-7-19)29-27(32)37-25-17-36-26-22(25)12-13-35-26;1-2-3/h3-11,18,22-26,31H,12-17,28H2,1-2H3,(H,29,32);3H,2H2,1H3/t22-,23-,24+,25-,26+;/m0./s1
• InChIKey: QWSHKNICRJHQCY-VBTXLZOXSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl N-[(2S,3R)-3-hydroxy-4-[N-(2-methylpropyl)4-aminobenzenesulfonamido]-1-phenylbutan-2-yl]carbamate; ethanol
• IUPAC Traditional name: darunavir; ethyl alcohol
• Synonyms: Prezista; TMC114; Darunavir Ethanolate (Prezista)

Database IDs

• CAS Number: 635728-49-3

CALCULATED PROPERTIES

• Acid pKa: 13.588299
• H Acceptors: 7
• H Donor: 3
• LogD (pH = 5.5): 2.8164854
• LogD (pH = 7.4): 2.8168132
• Log P: 2.8168175
• Molar Refractivity: 142.3406 cm^3
• Polarizability: 56.468124 Å^3
• Polar Surface Area: 140.42 Å^2
• Rotatable Bonds: 11
• Lipinski's Rule of Five: false

PROPERTIES

Pharmacology Properties

• Target: HIV Protease

Product Information

• Salt Data: Ethanolate