(2S)-N-[(2S,3R)-4-[(3S,4aS,8aS)-3-(tert-butylcarbamoyl)-decahydroisoquinolin-2-yl]-3-hydroxy-1-phenylbutan-2-yl]-2-(quinolin-2-ylformamido)butanediamide; methanesulfonic acid

• ChemBase ID: 154946
• Molecular Formular: C39H54N6O8S
• Molecular Mass: 766.94646
• Monoisotopic Mass: 766.37238372
• SMILES: CC(C)(C)NC(=O)[C@@H]1C[C@@H]2CCCC[C@@H]2CN1C[C@H]([C@H](Cc1ccccc1)NC(=O)[C@H](CC(=O)N)NC(=O)c1ccc2ccccc2n1)O.CS(=O)(=O)O
• Canonical SMILES: CS(=O)(=O)O.NC(=O)C[C@@H](C(=O)N[C@H]([C@@H](CN1C[C@H]2CCCC[C@H]2C[C@H]1C(=O)NC(C)(C)C)O)Cc1ccccc1)NC(=O)c1ccc2c(n1)cccc2
• InChI: InChI=1S/C38H50N6O5.CH4O3S/c1-38(2,3)43-37(49)32-20-26-14-7-8-15-27(26)22-44(32)23-33(45)30(19-24-11-5-4-6-12-24)41-36(48)31(21-34(39)46)42-35(47)29-18-17-25-13-9-10-16-28(25)40-29;1-5(2,3)4/h4-6,9-13,16-18,26-27,30-33,45H,7-8,14-15,19-23H2,1-3H3,(H2,39,46)(H,41,48)(H,42,47)(H,43,49);1H3,(H,2,3,4)/t26-,27+,30-,31-,32-,33+;/m0./s1
• InChIKey: IRHXGOXEBNJUSN-YOXDLBRISA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-N-[(2S,3R)-4-[(3S,4aS,8aS)-3-(tert-butylcarbamoyl)-decahydroisoquinolin-2-yl]-3-hydroxy-1-phenylbutan-2-yl]-2-(quinolin-2-ylformamido)butanediamide; methanesulfonic acid
• IUPAC Traditional name: methanesulfonic acid; saquinavir
• Synonyms: (2S)-N1[(1S,2R)-3-[(3S,4aS,8aS)-3-[[(1,1-Dimethylethyl)amino]carbonyl]octahydro-2(1H)-isoquinolinyl]-2-hydroxy-1-(phenylmethyl)propyl]-2-[(2-quinolinylcarbonyl)amino]butanediamide methanesulfonate; Ro-31-8959; Saquinavir mesylate; (2S)-N1[(1S,2R)-3-[(3S,4aS,8aS)-3-[[(1,1-Dimethylethyl)amino]carbonyl]octahydro-2-(1H)-isoquinolinyl]-2-hydroxy-1-(phenylmethyl)propyl]-2-[(2-quinolinylcarbonyl)amino]butanediamide Mesylate; Fortovase; Invirase; Ro 31-8959; Saquinavir Mesylate

Database IDs

• CAS Number: 149845-06-7
• MDL Number: MFCD00944907
• PubChem SID: 162249084
• PubChem CID: 60934

CALCULATED PROPERTIES

• Acid pKa: 13.608145
• H Acceptors: 7
• H Donor: 5
• LogD (pH = 5.5): 0.2937352
• LogD (pH = 7.4): 2.0477285
• Log P: 3.1554067
• Molar Refractivity: 186.6732 cm^3
• Polarizability: 74.205475 Å^3
• Polar Surface Area: 166.75 Å^2
• Rotatable Bonds: 13
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO: ≥5 mg/mL; Methanol; Water
• Apperance: White Solid; white to tan powder
• Melting Point: 232-234°C

Safety Information

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

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C38H50N6O5·CH4O3S

DETAILS

Sigma Aldrich - S8451

Biochem/physiol Actions
Saquinavir is an HIV Protease Inhibitor used in antiretroviral therapy. It inhibits both HIV-1 and HIV-2 proteases. Studies have also looked at saquinavir as a possible anti-cancer agent.

Toronto Research Chemicals - S135000

A selective HIV protease inhibitor. Antiviral.

REFERENCES

• Roberts, N.A., et al.: Science, 248, 358 (1990)
• Craig, J.C., et al.: Antiviral Res., 16, 295 (1990)