(3S,4aS,8aS)-N-(1-hydroxy-2-methylpropan-2-yl)-2-[(2R,3R)-2-hydroxy-3-[(3-hydroxy-2-methylphenyl)formamido]-4-(phenylsulfanyl)butyl]-decahydroisoquinoline-3-carboxamide

• ChemBase ID: 175060
• Molecular Formular: C32H45N3O5S
• Molecular Mass: 583.7818
• Monoisotopic Mass: 583.30799256
• SMILES: c1(cccc(c1C)C(=O)N[C@H]([C@@H](CN1C[C@@H]2[C@H](C[C@H]1C(=O)NC(CO)(C)C)CCCC2)O)CSc1ccccc1)O
• Canonical SMILES: OCC(NC(=O)[C@@H]1C[C@@H]2CCCC[C@@H]2CN1C[C@H]([C@@H](NC(=O)c1cccc(c1C)O)CSc1ccccc1)O)(C)C
• InChI: InChI=1S/C32H45N3O5S/c1-21-25(14-9-15-28(21)37)30(39)33-26(19-41-24-12-5-4-6-13-24)29(38)18-35-17-23-11-8-7-10-22(23)16-27(35)31(40)34-32(2,3)20-36/h4-6,9,12-15,22-23,26-27,29,36-38H,7-8,10-11,16-20H2,1-3H3,(H,33,39)(H,34,40)/t22-,23+,26-,27-,29+/m0/s1
• InChIKey: SLEPDNKZXLVSOH-HKWSIXNMSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3S,4aS,8aS)-N-(1-hydroxy-2-methylpropan-2-yl)-2-[(2R,3R)-2-hydroxy-3-[(3-hydroxy-2-methylphenyl)formamido]-4-(phenylsulfanyl)butyl]-decahydroisoquinoline-3-carboxamide
• IUPAC Traditional name: (3S,4aS,8aS)-N-(1-hydroxy-2-methylpropan-2-yl)-2-[(2R,3R)-2-hydroxy-3-[(3-hydroxy-2-methylphenyl)formamido]-4-(phenylsulfanyl)butyl]-octahydro-1H-isoquinoline-3-carboxamide
• Synonyms: (3S,4aS,8aS)-Decahydro-N-(2-hydroxy-1,1-dimethylethyl)-2-[(2R,3R)-2-hydroxy-3-[(3-hydroxy-2-methylbenzoyl)amino]-4-(phenylthio)butyl]-3-isoquinolinecarboxamide; AG 1402; M 8; Nelfinavir Hydroxy-tert-butylamide

Database IDs

• CAS Number: 213135-56-9
• PubChem SID: 164230970
• PubChem CID: 475066

CALCULATED PROPERTIES

• Acid pKa: 9.30971
• H Acceptors: 6
• H Donor: 5
• LogD (pH = 5.5): 1.3710304
• LogD (pH = 7.4): 3.1368499
• Log P: 3.686051
• Molar Refractivity: 164.2182 cm^3
• Polarizability: 63.839226 Å^3
• Polar Surface Area: 122.13 Å^2
• Rotatable Bonds: 11
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Acetone; Ethanol; Methanol
• Apperance: Off-White Solid
• Melting Point: 102+104°C

Safety Information

• Storage Condition: -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - N389760

A metabolite of Nelfinavir, which is used as an antiviral.

REFERENCES

• Patick, A.K., et al.: Antimicrol Ag. Chemother., 40, 292 (1996)
• Bardsley-Elliot, G.L., et al.: Drugs, 59, 581 (2000)