3-{[(1R,2S,5S)-3-[(2S)-2-[(tert-butylcarbamoyl)amino]-3,3-dimethylbutanoyl]-6,6-dimethyl-3-azabicyclo[3.1.0]hexan-2-yl]formamido}-4-cyclobutyl-2-oxobutanamide

• ChemBase ID: 162661
• Molecular Formular: C27H45N5O5
• Molecular Mass: 519.6767
• Monoisotopic Mass: 519.34206957
• SMILES: [C@@H]12[C@H]([C@H](N(C1)C(=O)[C@H](C(C)(C)C)NC(=O)NC(C)(C)C)C(=O)NC(C(=O)C(=O)N)CC1CCC1)C2(C)C
• Canonical SMILES: O=C(NC(C)(C)C)N[C@@H](C(C)(C)C)C(=O)N1C[C@H]2[C@H]([C@H]1C(=O)NC(C(=O)C(=O)N)CC1CCC1)C2(C)C
• InChI: InChI=1S/C27H45N5O5/c1-25(2,3)20(30-24(37)31-26(4,5)6)23(36)32-13-15-17(27(15,7)8)18(32)22(35)29-16(19(33)21(28)34)12-14-10-9-11-14/h14-18,20H,9-13H2,1-8H3,(H2,28,34)(H,29,35)(H2,30,31,37)/t15-,16?,17-,18-,20+/m0/s1
• InChIKey: LHHCSNFAOIFYRV-DOVBMPENSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-{[(1R,2S,5S)-3-[(2S)-2-[(tert-butylcarbamoyl)amino]-3,3-dimethylbutanoyl]-6,6-dimethyl-3-azabicyclo[3.1.0]hexan-2-yl]formamido}-4-cyclobutyl-2-oxobutanamide
• IUPAC Traditional name: boceprevir
• Synonyms: (1R,2S,5S)-N-[3-Amino-1-(cyclobutylmethyl)-2,3-dioxopropyl]-3-[(2S)-2-[[[(1,1-dimethylethyl)amino]carbonyl]amino]-3,3-dimethyl-1-oxobutyl]-6,6-dimethyl-3-azabicyclo[3.1.0]hexane-2-carboxamide; EBP 520; Sch 503034; Boceprevir

Database IDs

• CAS Number: 394730-60-0
• PubChem SID: 162256796
• PubChem CID: 10324367

CALCULATED PROPERTIES

• Acid pKa: 12.435855
• H Acceptors: 5
• H Donor: 4
• LogD (pH = 5.5): 1.7752962
• LogD (pH = 7.4): 1.7752934
• Log P: 1.7752964
• Molar Refractivity: 138.202 cm^3
• Polarizability: 54.38069 Å^3
• Polar Surface Area: 150.7 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: Off-White to Pale Yellow Solid
• Melting Point: 110-120°C

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - B674500

An NS3 serine protease inhibitor of hepatitis C virus, for the treatment of HCV infection.

REFERENCES

• Malcolm, B., et al.: Antimicrob. Agents Chemother., 50, 1013 (2006)
• Cubero, M., et al.: Virology, 370, 237 (2006)
• Venkatraman, S., et al.: J. Med. Chem., 49, 6074 (2006)