benzyl N-[(2R,3R)-4-[(3S,4aS,8aS)-3-[(1-hydroxy-2-methylpropan-2-yl)carbamoyl]-decahydroisoquinolin-2-yl]-3-hydroxy-1-(phenylsulfanyl)butan-2-yl]carbamate

• ChemBase ID: 165489
• Molecular Formular: C32H45N3O5S
• Molecular Mass: 583.7818
• Monoisotopic Mass: 583.30799256
• SMILES: C1CC[C@H]2[C@@H](C1)C[C@H](N(C2)C[C@H]([C@H](CSc1ccccc1)NC(=O)OCc1ccccc1)O)C(=O)NC(CO)(C)C
• Canonical SMILES: OCC(NC(=O)[C@@H]1C[C@@H]2CCCC[C@@H]2CN1C[C@H]([C@@H](NC(=O)OCc1ccccc1)CSc1ccccc1)O)(C)C
• InChI: InChI=1S/C32H45N3O5S/c1-32(2,22-36)34-30(38)28-17-24-13-9-10-14-25(24)18-35(28)19-29(37)27(21-41-26-15-7-4-8-16-26)33-31(39)40-20-23-11-5-3-6-12-23/h3-8,11-12,15-16,24-25,27-29,36-37H,9-10,13-14,17-22H2,1-2H3,(H,33,39)(H,34,38)/t24-,25+,27-,28-,29+/m0/s1
• InChIKey: LGNQXYJOAQQMEH-RIVMDFSBSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: benzyl N-[(2R,3R)-4-[(3S,4aS,8aS)-3-[(1-hydroxy-2-methylpropan-2-yl)carbamoyl]-decahydroisoquinolin-2-yl]-3-hydroxy-1-(phenylsulfanyl)butan-2-yl]carbamate
• IUPAC Traditional name: benzyl N-[(2R,3R)-4-[(3S,4aS,8aS)-3-[(1-hydroxy-2-methylpropan-2-yl)carbamoyl]-octahydro-1H-isoquinolin-2-yl]-3-hydroxy-1-(phenylsulfanyl)butan-2-yl]carbamate
• Synonyms: [(1R,2R)-2-Hydroxy-3-[(3S,4aS,8aS)-octahydro-3-[[(2-hydroxy-1,1-dimethylethyl)amino]carbonyl]-2(1H)-isoquinolinyl]-1-[(phenylthio)methyl]propyl]carbamic Acid Phenylmethyl Ester; (3S,4aS,8aS)-Decahydro-N-(2-hydroxy-1,1-dimethylethyl)-2-[(2R,3R)-2-hydroxy-3-carbobenzyloxyamino-4-phenylthiobutyl]-3-isoquinolinecarboxamide

Database IDs

• CAS Number: 213135-55-8
• PubChem SID: 162259622
• PubChem CID: 45038786

CALCULATED PROPERTIES

• Acid pKa: 13.420612
• H Acceptors: 5
• H Donor: 4
• LogD (pH = 5.5): 1.712691
• LogD (pH = 7.4): 3.4787123
• Log P: 4.1969733
• Molar Refractivity: 162.7618 cm^3
• Polarizability: 64.21431 Å^3
• Polar Surface Area: 111.13 Å^2
• Rotatable Bonds: 13
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Chloroform; Dichloromethane
• Apperance: Off-White to Pale Yellow Solid
• Melting Point: 127-129°C

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - D212050

An intermediate in the synthesis for the metabolite of Nelfinavir

REFERENCES

• Chong, K; J. Med. Chem., 36, 2575 (1993)