(2S)-N-[(2S,3R)-4-[(3S,4aS,8aS)-3-(tert-butylcarbamoyl)-decahydroisoquinolin-2-yl]-3-hydroxy-1-phenylbutan-2-yl]-2-[(2H6)quinolin-2-ylformamido]butanediamide

• ChemBase ID: 177692
• Molecular Formular: C38H50N6O5
• Molecular Mass: 670.8408
• Monoisotopic Mass: 670.38426873
• SMILES: c1cccc2c1ccc(n2)C(=O)N[C@H](C(=O)N[C@H]([C@@H](CN1C[C@@H]2[C@H](C[C@H]1C(=O)NC(C)(C)C)CCCC2)O)Cc1ccccc1)CC(=O)N
• Canonical SMILES: 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/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/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)/t26-,27+,30-,31-,32-,33+/m0/s1
• InChIKey: QWAXKHKRTORLEM-UGJKXSETSA-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-[(^2H₆)quinolin-2-ylformamido]butanediamide
• IUPAC Traditional name: (2S)-N-[(2S,3R)-4-[(3S,4aS,8aS)-3-(tert-butylcarbamoyl)-octahydro-1H-isoquinolin-2-yl]-3-hydroxy-1-phenylbutan-2-yl]-2-[(^2H₆)quinolin-2-ylformamido]butanediamide
• 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-d6; Fortovase-d6; Invirase-d6; Ro 31-8959-d6; Saquinavir-d6

Database IDs

• PubChem SID: 164233602
• PubChem CID: 71752155

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: 74.23516 Å^3
• Polar Surface Area: 166.75 Å^2
• Rotatable Bonds: 13
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - S135003

Labelled Saquinavir (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)