(3S,4aS,8aS)-N-tert-butyl-2-[(2R,3R)-2-hydroxy-3-{[3-hydroxy-2-(2H3)methylphenyl]formamido}-4-(phenylsulfanyl)butyl]-decahydroisoquinoline-3-carboxamide

• ChemBase ID: 175059
• Molecular Formular: C32H45N3O4S
• Molecular Mass: 567.7824
• Monoisotopic Mass: 567.31307794
• SMILES: c1(cccc(c1C)C(=O)N[C@H]([C@@H](CN1C[C@@H]2[C@H](C[C@H]1C(=O)NC(C)(C)C)CCCC2)O)CSc1ccccc1)O
• Canonical SMILES: O[C@@H]([C@@H](NC(=O)c1cccc(c1C)O)CSc1ccccc1)CN1C[C@H]2CCCC[C@H]2C[C@H]1C(=O)NC(C)(C)C
• InChI: InChI=1S/C32H45N3O4S/c1-21-25(15-10-16-28(21)36)30(38)33-26(20-40-24-13-6-5-7-14-24)29(37)19-35-18-23-12-9-8-11-22(23)17-27(35)31(39)34-32(2,3)4/h5-7,10,13-16,22-23,26-27,29,36-37H,8-9,11-12,17-20H2,1-4H3,(H,33,38)(H,34,39)/t22-,23+,26-,27-,29+/m0/s1
• InChIKey: QAGYKUNXZHXKMR-HKWSIXNMSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3S,4aS,8aS)-N-tert-butyl-2-[(2R,3R)-2-hydroxy-3-{[3-hydroxy-2-(^2H₃)methylphenyl]formamido}-4-(phenylsulfanyl)butyl]-decahydroisoquinoline-3-carboxamide
• IUPAC Traditional name: (3S,4aS,8aS)-N-tert-butyl-2-[(2R,3R)-2-hydroxy-3-{[3-hydroxy-2-(^2H₃)methylphenyl]formamido}-4-(phenylsulfanyl)butyl]-octahydro-1H-isoquinoline-3-carboxamide
• Synonyms: (3S,4aS,8aS)-N-(1,1-Dimethylethyl)decahydro-2-[(2R,3R)-2-hydroxy-3-[(3-hydroxy-2-methylbenzoyl)amino]-4-(phenylthio)butyl]-3-isoquinolinecarboxamide; AG 1341; Nelfinavir-d3

Database IDs

• PubChem SID: 164230969
• PubChem CID: 45040007

CALCULATED PROPERTIES

• Acid pKa: 9.317774
• H Acceptors: 5
• H Donor: 4
• LogD (pH = 5.5): 2.3172343
• LogD (pH = 7.4): 4.085969
• Log P: 4.718828
• Molar Refractivity: 162.6745 cm^3
• Polarizability: 63.29092 Å^3
• Polar Surface Area: 101.9 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: White Solid
• Melting Point: 188-190°C

Safety Information

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

DETAILS

Toronto Research Chemicals - N389752

An antiviral. Labelled HIV protease inhibitor.

REFERENCES

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