(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl N-[(2S,3R)-3-hydroxy-4-{N-[2-(2H3)methyl(2H6)propyl]4-aminobenzenesulfonamido}-1-phenylbutan-2-yl]carbamate

• ChemBase ID: 165414
• Molecular Formular: C27H37N3O7S
• Molecular Mass: 547.66358
• Monoisotopic Mass: 547.23522154
• SMILES: O(C(=O)N[C@H]([C@@H](CN(S(=O)(=O)c1ccc(cc1)N)CC(C)C)O)Cc1ccccc1)[C@H]1CO[C@@H]2[C@H]1CCO2
• 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
• InChI: InChI=1S/C27H37N3O7S/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/h3-11,18,22-26,31H,12-17,28H2,1-2H3,(H,29,32)/t22-,23-,24+,25-,26+/m0/s1
• InChIKey: CJBJHOAVZSMMDJ-HEXNFIEUSA-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-(^2H₃)methyl(^2H₆)propyl]4-aminobenzenesulfonamido}-1-phenylbutan-2-yl]carbamate
• IUPAC Traditional name: (3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl N-[(2S,3R)-3-hydroxy-4-{N-[2-(^2H₃)methyl(^2H₆)propyl]4-aminobenzenesulfonamido}-1-phenylbutan-2-yl]carbamate
• Synonyms: [(1S,2R)-3-[[(4-Aminophenyl)sulfonyl](2-methylpropyl-d9)amino]-2-hydroxy-1-(phenyl-methyl)propyl]carabamic Acid (3R,3aS,6aR)-Hexahydrofuro[2,3-b]-furan-3-yl Ester; TMC-114-d9; UIC-94017-d9; Darunavir-d9

Database IDs

• PubChem SID: 162259547
• PubChem CID: 25265814

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: 56.468235 Å^3
• Polar Surface Area: 140.42 Å^2
• Rotatable Bonds: 11
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Chloroform
• Apperance: Off-White to Plae Yellow Solid
• Melting Point: 74-76°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - D193502

Second generation HIV-1-protease inhibitor; structurally similar to amprenavir. Antiviral.

REFERENCES

• Koh, Y., et al.: Antimicrob. Agents Chemother., 47, 3123 (2003)
• Arasteh, K., et al.: AIDS, 19, 943 (2003)
• Surleraux, D.L.N.G., et al.: J. Med. Chem., 48, 1813 (2003)