(2R,3S)-4-cyclobutyl-3-{[(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]hexan-2-yl]formamido}-2-hydroxybutanamide

• ChemBase ID: 167546
• Molecular Formular: C27H47N5O5
• Molecular Mass: 521.69258
• Monoisotopic Mass: 521.35771963
• 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)N[C@H]([C@H](C(=O)N)O)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)N[C@H]([C@H](C(=O)N)O)CC1CCC1)C2(C)C
• InChI: InChI=1S/C27H47N5O5/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/h14-20,33H,9-13H2,1-8H3,(H2,28,34)(H,29,35)(H2,30,31,37)/t15-,16-,17-,18-,19+,20+/m0/s1
• InChIKey: FEBWCINGHXXUCV-GFLQDLJJSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3S)-4-cyclobutyl-3-{[(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]hexan-2-yl]formamido}-2-hydroxybutanamide
• IUPAC Traditional name: (2R,3S)-4-cyclobutyl-3-{[(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]hexan-2-yl]formamido}-2-hydroxybutanamide
• Synonyms: (1R,2S,5S)-N-[(1S,2R)-3-amino-1-(cyclobutylmethyl)-2-hydroxy-3-oxopropyl]-3-[(2S)-2-[[[(1,1-dimethylethyl-d9)amino]carbonyl]amino]-3,3-dimethyl-1-oxobutyl]-6,6-dimethyl-3-azabicyclo[3.1.0]hexane-2-carboxamide; (1'S,2'R)-2'-Dihydro Boceprevir-d9(Boceprevir Metabolite M28-d9)

Database IDs

• PubChem SID: 162261679
• PubChem CID: 71316140

CALCULATED PROPERTIES

• Acid pKa: 12.535312
• H Acceptors: 5
• H Donor: 5
• LogD (pH = 5.5): 0.85574156
• LogD (pH = 7.4): 0.85573864
• Log P: 0.8557418
• Molar Refractivity: 138.8185 cm^3
• Polarizability: 54.922577 Å^3
• Polar Surface Area: 153.86 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - D448642

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