(1R,2S,5S)-3-[(2S)-2-[(tert-butylcarbamoyl)amino]-3,3-dimethylbutanoyl]-6,6-dimethyl-3-azabicyclo[3.1.0]hexane-2-carboxylic acid

• ChemBase ID: 162664
• Molecular Formular: C19H33N3O4
• Molecular Mass: 367.48302
• Monoisotopic Mass: 367.24710655
• 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)O)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)O)C2(C)C
• InChI: InChI=1S/C19H33N3O4/c1-17(2,3)13(20-16(26)21-18(4,5)6)14(23)22-9-10-11(19(10,7)8)12(22)15(24)25/h10-13H,9H2,1-8H3,(H,24,25)(H2,20,21,26)/t10-,11-,12-,13+/m0/s1
• InChIKey: ODCGBMOBUUHGRG-ZDEQEGDKSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,2S,5S)-3-[(2S)-2-[(tert-butylcarbamoyl)amino]-3,3-dimethylbutanoyl]-6,6-dimethyl-3-azabicyclo[3.1.0]hexane-2-carboxylic acid
• IUPAC Traditional name: (1R,2S,5S)-3-[(2S)-2-[(tert-butylcarbamoyl)amino]-3,3-dimethylbutanoyl]-6,6-dimethyl-3-azabicyclo[3.1.0]hexane-2-carboxylic acid
• Synonyms: (1R,2S,5S)-3-[(2S)-2-[[[[1,1-Dimethylethyl]amino]carbonyl]amino]-3,3-dimethyl-1-oxobutyl]-6,6-dimethyl-3-azabicyclo[3.1.0]hexane-2-carboxylic Acid; Boceprevir Metabolite M4

Database IDs

• CAS Number: 816444-90-3
• PubChem SID: 162256799
• PubChem CID: 11530743

CALCULATED PROPERTIES

• Acid pKa: 3.8093398
• H Acceptors: 4
• H Donor: 3
• LogD (pH = 5.5): -0.09859692
• LogD (pH = 7.4): -1.6634864
• Log P: 1.5945854
• Molar Refractivity: 97.264 cm^3
• Polarizability: 38.382816 Å^3
• Polar Surface Area: 98.74 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - B674520

A metabolite of the Hepatitis C virus NS3 serine protease inhibitor Boceprevir (B675500).

REFERENCES

• Venkatraman, S. et al.: J. Med. Chem., 49, 6074 (2006)
• Morgan, A.J, et al.: J. Lab. Cpd. Radiopharmac., 54, 613 (2006)