(2S)-1-[(2S,4R)-4-benzyl-2-hydroxy-4-{[(1S,2R)-2-hydroxy-2,3-dihydro-1H-inden-1-yl]carbamoyl}butyl]-N-tert-butyl-4-(pyridin-3-ylmethyl)piperazine-2-carboxamide; O-(hydroperoxysulfinyl)oxidanol

• ChemBase ID: 171590
• Molecular Formular: C36H49N5O8S
• Molecular Mass: 711.86796
• Monoisotopic Mass: 711.33018455
• SMILES: c1ccncc1CN1C[C@H](N(CC1)C[C@H](C[C@H](C(=O)N[C@H]1c2c(C[C@H]1O)cccc2)Cc1ccccc1)O)C(=O)NC(C)(C)C.S(=O)(OO)O
• Canonical SMILES: O[C@H](CN1CCN(C[C@H]1C(=O)NC(C)(C)C)Cc1cccnc1)C[C@H](C(=O)N[C@@H]1[C@H](O)Cc2c1cccc2)Cc1ccccc1.OOS(=O)O
• InChI: InChI=1S/C36H47N5O4.H2O4S/c1-36(2,3)39-35(45)31-24-40(22-26-12-9-15-37-21-26)16-17-41(31)23-29(42)19-28(18-25-10-5-4-6-11-25)34(44)38-33-30-14-8-7-13-27(30)20-32(33)43;1-4-5(2)3/h4-15,21,28-29,31-33,42-43H,16-20,22-24H2,1-3H3,(H,38,44)(H,39,45);1H,(H,2,3)/t28-,29+,31+,32-,33+;/m1./s1
• InChIKey: RWRBAGUHAIVYEC-BDEHJDMKSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-1-[(2S,4R)-4-benzyl-2-hydroxy-4-{[(1S,2R)-2-hydroxy-2,3-dihydro-1H-inden-1-yl]carbamoyl}butyl]-N-tert-butyl-4-(pyridin-3-ylmethyl)piperazine-2-carboxamide; O-(hydroperoxysulfinyl)oxidanol
• IUPAC Traditional name: O-(hydroperoxysulfinyl)oxidanol; indinavir
• Synonyms: 2,3,5-Trideoxy-N-[(1S,2R)-2,3-dihydro-2-hydroxy-1H-inden-1-yl]-5-[(2S)-2[[(1,1-dimethylethyl)amino]carbonyl]-4-(3-pyridinylmethyl)-1-piperazinyl]-2-(phenylmethyl)-D-erythro-pentonamide; MK-639; Crixivan; Indinavir Sulfate

Database IDs

• CAS Number: 157810-81-6
• PubChem SID: 164227500
• PubChem CID: 46781952

CALCULATED PROPERTIES

• Acid pKa: 13.191399
• H Acceptors: 7
• H Donor: 4
• LogD (pH = 5.5): 0.94212973
• LogD (pH = 7.4): 2.5233755
• Log P: 2.8099308
• Molar Refractivity: 175.8941 cm^3
• Polarizability: 68.852844 Å^3
• Polar Surface Area: 118.03 Å^2
• Rotatable Bonds: 13
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Water
• Apperance: White Solid
• Melting Point: 150-153°C (dec)

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - I525000

Member of the novel hydroxyaminopentane amide class of HIV-1 protease inhibitors. Antiviral.

REFERENCES

• Vacca, J.P., et al.: Proc. Nat. Acad. Sci. USA, 91, 4096 (1994)
• Dorsey, B. D., et al.: J. Med. Chem., 37, 3443 (1994)
• Balani, S.K., et al.: Drug Metab. Dispos., 23, 266 (1995)