(2S)-N-[(2S,3R)-4-[(3S,4aS,8aS)-3-{[2-(2H3)methyl(2H6)propan-2-yl]carbamoyl}-decahydroisoquinolin-2-yl]-3-hydroxy-1-phenylbutan-2-yl]-2-aminobutanediamide

• ChemBase ID: 159831
• Molecular Formular: C28H45N5O4
• Molecular Mass: 515.688
• Monoisotopic Mass: 515.34715495
• SMILES: 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)N
• InChI: InChI=1S/C28H45N5O4/c1-28(2,3)32-27(37)23-14-19-11-7-8-12-20(19)16-33(23)17-24(34)22(13-18-9-5-4-6-10-18)31-26(36)21(29)15-25(30)35/h4-6,9-10,19-24,34H,7-8,11-17,29H2,1-3H3,(H2,30,35)(H,31,36)(H,32,37)/t19-,20+,21-,22-,23-,24+/m0/s1
• InChIKey: NVJKKZFIMURKNZ-DVZKKUMJSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-N-[(2S,3R)-4-[(3S,4aS,8aS)-3-{[2-(^2H₃)methyl(^2H₆)propan-2-yl]carbamoyl}-decahydroisoquinolin-2-yl]-3-hydroxy-1-phenylbutan-2-yl]-2-aminobutanediamide
• IUPAC Traditional name: (2S)-N-[(2S,3R)-4-[(3S,4aS,8aS)-3-{[2-(^2H₃)methyl(^2H₆)propan-2-yl]carbamoyl}-octahydro-1H-isoquinolin-2-yl]-3-hydroxy-1-phenylbutan-2-yl]-2-aminobutanediamide
• Synonyms: (2S)-2-Amino-N1-[(1S,2R)-3-[(3S,4aS,8aS)-3-[[(1,1-dimethylethyl)amino]carbonyl]octahydro-2(1H)-isoquinolinyl]-2-hydroxy-1-(phenylmethyl)propyl]-butanediamide; 2-Amino-N-[1-benzyl-3-(3-tert-butylcarbamoyl-octahydro-isoquinolin-2-yl)-2-hydropropyl]-succinamide

Database IDs

• PubChem SID: 162253966
• PubChem CID: 46780144

CALCULATED PROPERTIES

• Acid pKa: 13.781811
• H Acceptors: 6
• H Donor: 5
• LogD (pH = 5.5): -3.7477179
• LogD (pH = 7.4): -0.44337887
• Log P: 0.93888074
• Molar Refractivity: 143.0096 cm^3
• Polarizability: 56.68985 Å^3
• Polar Surface Area: 150.78 Å^2
• Rotatable Bonds: 11
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Chloroform; Methanol
• Apperance: White Solid

DETAILS

Toronto Research Chemicals - A596702

Labelled Saquinavir derivative useful in immunoassay for HIV protease inhibitors.

REFERENCES

• Fitzsimmons, M., et al.: Drug Metab. Dispos., 25, 256 (1997)
• Perry, C., et al.: Drugs, 1998, 55, 461 (1998)