methyl (1R,2S,5S)-3-[(2S)-3,3-dimethyl-2-({[2-(2H3)methyl(2H6)propan-2-yl]carbamoyl}amino)butanoyl]-6,6-dimethyl-3-azabicyclo[3.1.0]hexane-2-carboxylate

• ChemBase ID: 162663
• Molecular Formular: C20H35N3O4
• Molecular Mass: 381.5096
• Monoisotopic Mass: 381.26275662
• 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)OC)C2(C)C
• Canonical SMILES: COC(=O)[C@H]1N(C[C@H]2[C@H]1C2(C)C)C(=O)[C@H](C(C)(C)C)NC(=O)NC(C)(C)C
• InChI: InChI=1S/C20H35N3O4/c1-18(2,3)14(21-17(26)22-19(4,5)6)15(24)23-10-11-12(20(11,7)8)13(23)16(25)27-9/h11-14H,10H2,1-9H3,(H2,21,22,26)/t11-,12-,13-,14+/m0/s1
• InChIKey: BOAWSIPWPIUQLQ-XDQVBPFNSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl (1R,2S,5S)-3-[(2S)-3,3-dimethyl-2-({[2-(^2H₃)methyl(^2H₆)propan-2-yl]carbamoyl}amino)butanoyl]-6,6-dimethyl-3-azabicyclo[3.1.0]hexane-2-carboxylate
• IUPAC Traditional name: methyl (1R,2S,5S)-3-[(2S)-3,3-dimethyl-2-({[2-(^2H₃)methyl(^2H₆)propan-2-yl]carbamoyl}amino)butanoyl]-6,6-dimethyl-3-azabicyclo[3.1.0]hexane-2-carboxylate
• Synonyms: (1R,2S,5S)-3-[(2S)-2-[[[[1,1-Di(methyl-d3)ethyl-2,2,2-d3]amino]carbonyl]amino]-3,3-di(methyl-d3)-1-oxobutyl-4,4,4-d3]-6,6-dimethyl-3-azabicyclo[3.1.0]hexane-2-carboxylic Acid Methyl Ester; Boceprevir Metabolite M4-d9 Methyl Ester

Database IDs

• CAS Number: 1158083-48-7
• PubChem SID: 162256798
• PubChem CID: 57386225

CALCULATED PROPERTIES

• Acid pKa: 14.851888
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 1.7404794
• LogD (pH = 7.4): 1.7404795
• Log P: 1.7404795
• Molar Refractivity: 102.0331 cm^3
• Polarizability: 40.46263 Å^3
• Polar Surface Area: 87.74 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Dichloromethane; Ethyl Acetate; Methanol
• Apperance: White Foam

DETAILS

Toronto Research Chemicals - B674517

Protected Boceprevir Metabolite M4-d9 (B674522). A labelled 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)