(1S,3aR,6aS)-2-[(2S)-2-[(2S)-2-cyclohexyl-2-(pyrazin-2-ylformamido)acetamido]-3,3-dimethylbutanoyl]-octahydrocyclopenta[c]pyrrole-1-carboxylic acid

• ChemBase ID: 166175
• Molecular Formular: C27H39N5O5
• Molecular Mass: 513.62906
• Monoisotopic Mass: 513.29511937
• SMILES: C1CC[C@H]2[C@@H]1CN([C@@H]2C(=O)O)C(=O)[C@@H](NC(=O)[C@@H](NC(=O)c1nccnc1)C1CCCCC1)C(C)(C)C
• Canonical SMILES: O=C([C@H](C1CCCCC1)NC(=O)c1nccnc1)N[C@@H](C(C)(C)C)C(=O)N1C[C@H]2[C@@H]([C@H]1C(=O)O)CCC2
• InChI: InChI=1S/C27H39N5O5/c1-27(2,3)22(25(35)32-15-17-10-7-11-18(17)21(32)26(36)37)31-24(34)20(16-8-5-4-6-9-16)30-23(33)19-14-28-12-13-29-19/h12-14,16-18,20-22H,4-11,15H2,1-3H3,(H,30,33)(H,31,34)(H,36,37)/t17-,18-,20-,21-,22+/m0/s1
• InChIKey: GUDVCEUDUGFATD-OOOLTRJPSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,3aR,6aS)-2-[(2S)-2-[(2S)-2-cyclohexyl-2-(pyrazin-2-ylformamido)acetamido]-3,3-dimethylbutanoyl]-octahydrocyclopenta[c]pyrrole-1-carboxylic acid
• IUPAC Traditional name: (1S,3aR,6aS)-2-[(2S)-2-[(2S)-2-cyclohexyl-2-(pyrazin-2-ylformamido)acetamido]-3,3-dimethylbutanoyl]-hexahydro-1H-cyclopenta[c]pyrrole-1-carboxylic acid
• Synonyms: (1S,3aR,6aS)-(2S)-2-Cyclohexyl-N-(2-pyrazinylcarbonyl)glycyl-3-methyl-L-valyloctahydrocyclopenta[c]pyrrole-1-carboxylic Acid; (1S,3aR,6aS)-(2S)-2-Cyclohexyl-N-(pyrazinylcarbonyl)glycyl-3-methyl-L-valyloctahydrocyclopenta[c]pyrrole-1-carboxylic Acid; Des[N-[(1S)-1-[2-(cyclopropylamino)-2-oxoacetyl]butyl]carboxamido] 1-Carboxy Telaprevir

Database IDs

• CAS Number: 402958-98-9
• PubChem SID: 162260308
• PubChem CID: 23634852

CALCULATED PROPERTIES

• Acid pKa: 3.8851652
• H Acceptors: 7
• H Donor: 3
• LogD (pH = 5.5): 0.35819474
• LogD (pH = 7.4): -1.2430023
• Log P: 1.9782026
• Molar Refractivity: 134.3418 cm^3
• Polarizability: 52.717667 Å^3
• Polar Surface Area: 141.59 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - D288915

An intermediate in the preparation of Telaprevir (T015650) as hepatitis C virus (HCV) protease inhibitor.