(3S,4aS,8aS)-N-tert-butyl-2-[(2R,3R)-2-hydroxy-3-[(3-hydroxy-2-methylphenyl)formamido]-4-(phenylsulfanyl)butyl]-decahydroisoquinoline-3-carboxamide; methanesulfonic acid

• ChemBase ID: 154650
• Molecular Formular: C33H49N3O7S2
• Molecular Mass: 663.88806
• Monoisotopic Mass: 663.30119292
• SMILES: Cc1c(cccc1O)C(=O)N[C@@H](CSc1ccccc1)[C@@H](CN1C[C@H]2CCCC[C@H]2C[C@H]1C(=O)NC(C)(C)C)O.CS(=O)(=O)O
• Canonical SMILES: CS(=O)(=O)O.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.CH4O3S/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;1-5(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);1H3,(H,2,3,4)/t22-,23+,26-,27-,29+;/m0./s1
• InChIKey: NQHXCOAXSHGTIA-SKXNDZRYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3S,4aS,8aS)-N-tert-butyl-2-[(2R,3R)-2-hydroxy-3-[(3-hydroxy-2-methylphenyl)formamido]-4-(phenylsulfanyl)butyl]-decahydroisoquinoline-3-carboxamide; methanesulfonic acid
• IUPAC Traditional name: methanesulfonic acid; nelfinavir
• 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; Nelfin; Nelfinivir; Viracept; Nelfinavir Mesylate; 3S,4aS,8aS)-N-(1,1-Dimethylethyl)decahydro-2-[(2R,3R)-2-hydroxy-3-[(3-hydroxy-2-methylbenzoyl)amino]-4-(phenylthio)butyl]-3-isoquinolinecarboxamide methanesulfonate; AG-1343; Nelfinavir methanesulfonate hydrate; Nelfinavir mesylate hydrate

Database IDs

• CAS Number: 159989-65-8(anhydrous); 159989-65-8
• MDL Number: MFCD00931436
• PubChem SID: 162248788
• PubChem CID: 64142

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: 63.215218 Å^3
• Polar Surface Area: 101.9 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Acetone; Dichloromethane; DMSO: ≥2 mg/mL; Ethanol; Isopropanol; Methanol
• Apperance: White Solid; white to off-white powder
• Melting Point: 131-135°C

Safety Information

• Storage Condition: -20°C Freezer
• German water hazard class: 3
• GHS Hazard statements: H413
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C32H45N3O4S · CH3SO3H · xH2O

DETAILS

Sigma Aldrich - PZ0013

Biochem/physiol Actions
Nelfinavir is a HIV protease inhibitor; antiretroviral; and anti-tumor agent.
Legal Information
Sold for research purposes under agreement from Pfizer Inc.

Toronto Research Chemicals - N389750

An antiviral. HIV protease inhibitor.

REFERENCES

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