(3S,4aS,8aS)-2-[(3R)-3-amino-2-hydroxy-4-(phenylsulfanyl)butyl]-N-tert-butyl-decahydroisoquinoline-3-carboxamide

• ChemBase ID: 160192
• Molecular Formular: C24H39N3O2S
• Molecular Mass: 433.65036
• Monoisotopic Mass: 433.2762985
• SMILES: C1CC[C@H]2[C@@H](C1)C[C@H](N(C2)CC(O)[C@H](CSc1ccccc1)N)C(=O)NC(C)(C)C
• Canonical SMILES: N[C@H](C(CN1C[C@H]2CCCC[C@H]2C[C@H]1C(=O)NC(C)(C)C)O)CSc1ccccc1
• InChI: InChI=1S/C24H39N3O2S/c1-24(2,3)26-23(29)21-13-17-9-7-8-10-18(17)14-27(21)15-22(28)20(25)16-30-19-11-5-4-6-12-19/h4-6,11-12,17-18,20-22,28H,7-10,13-16,25H2,1-3H3,(H,26,29)/t17-,18+,20-,21-,22?/m0/s1
• InChIKey: FWGHKOLIXLOLBU-JWUYBYNISA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3S,4aS,8aS)-2-[(3R)-3-amino-2-hydroxy-4-(phenylsulfanyl)butyl]-N-tert-butyl-decahydroisoquinoline-3-carboxamide
• IUPAC Traditional name: (3S,4aS,8aS)-2-[(3R)-3-amino-2-hydroxy-4-(phenylsulfanyl)butyl]-N-tert-butyl-octahydro-1H-isoquinoline-3-carboxamide
• Synonyms: (3S,4aS,8aS)-2-((2R,3R)-3-Amino-2-hydroxy-4-phenylthiobutyl)decahydroisoquinoline-3-carboxylic Acid tert-Butylamide; (3S,4aS,8aS)-2-[(2R,3R)-3-Amino-2-hydroxy-4-(phenylthio)butyl]-N-(1,1-dimethylethyl)decahydro-3-isoquinolinecarboxamide

Database IDs

• CAS Number: 159878-05-4
• PubChem SID: 162254327
• PubChem CID: 71313273

CALCULATED PROPERTIES

• Acid pKa: 14.186917
• H Acceptors: 4
• H Donor: 3
• LogD (pH = 5.5): -1.8925734
• LogD (pH = 7.4): 0.8198649
• Log P: 3.0812726
• Molar Refractivity: 125.5381 cm^3
• Polarizability: 49.95138 Å^3
• Polar Surface Area: 78.59 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Acetone; Chloroform; Dichlormethane; Ethyl Acetate; Methanol
• Apperance: Brown Foaming Solid

DETAILS

Toronto Research Chemicals - A611645

An intermediate in the synthesis of Nelfinavir.