ethyl (2E,4S)-4-[(2R,5S)-2-[(4-fluorophenyl)methyl]-6-methyl-5-[(5-methyl-1,2-oxazol-3-yl)formamido]-4-oxoheptanamido]-5-[(3S)-2-oxopyrrolidin-3-yl]pent-2-enoate

• ChemBase ID: 177657
• Molecular Formular: C31H39FN4O7
• Molecular Mass: 598.6623632
• Monoisotopic Mass: 598.28027783
• SMILES: C(=O)(N[C@H](C(=O)C[C@H](C(=O)N[C@@H](C[C@@H]1CCNC1=O)/C=C/C(=O)OCC)Cc1ccc(cc1)F)C(C)C)c1cc(on1)C
• Canonical SMILES: CCOC(=O)/C=C/[C@H](C[C@@H]1CCNC1=O)NC(=O)[C@H](Cc1ccc(cc1)F)CC(=O)[C@H](C(C)C)NC(=O)c1noc(c1)C
• InChI: InChI=1S/C31H39FN4O7/c1-5-42-27(38)11-10-24(16-21-12-13-33-29(21)39)34-30(40)22(15-20-6-8-23(32)9-7-20)17-26(37)28(18(2)3)35-31(41)25-14-19(4)43-36-25/h6-11,14,18,21-22,24,28H,5,12-13,15-17H2,1-4H3,(H,33,39)(H,34,40)(H,35,41)/b11-10+/t21-,22+,24+,28-/m0/s1
• InChIKey: CAYJBRBGZBCZKO-BHGBQCOSSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: ethyl (2E,4S)-4-[(2R,5S)-2-[(4-fluorophenyl)methyl]-6-methyl-5-[(5-methyl-1,2-oxazol-3-yl)formamido]-4-oxoheptanamido]-5-[(3S)-2-oxopyrrolidin-3-yl]pent-2-enoate
• IUPAC Traditional name: ethyl (2E,4S)-4-[(2R,5S)-2-[(4-fluorophenyl)methyl]-6-methyl-5-[(5-methyl-1,2-oxazol-3-yl)formamido]-4-oxoheptanamido]-5-[(3S)-2-oxopyrrolidin-3-yl]pent-2-enoate
• Synonyms: (2E,4S)-4-[[(2R,5S)-2-[(4-Fluorophenyl)methyl]-6-methyl-5-[[(5-methyl-3-isoxazolyl)carbonyl]amino]-1,4-dioxoheptyl]amino]-5-[(3S)-2-oxo-3-pyrrolidinyl]-2-pentenoic Acid; AG 7088; Rupintrivir

Database IDs

• CAS Number: 223537-30-2
• PubChem SID: 164233567
• PubChem CID: 6440352

CALCULATED PROPERTIES

• Acid pKa: 12.494106
• H Acceptors: 6
• H Donor: 3
• LogD (pH = 5.5): 3.2100778
• LogD (pH = 7.4): 3.210076
• Log P: 3.2100792
• Molar Refractivity: 157.2441 cm^3
• Polarizability: 59.434727 Å^3
• Polar Surface Area: 156.7 Å^2
• Rotatable Bonds: 16
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Chloroform; Methanol
• Apperance: White Solid
• Melting Point: 170-171°C

Safety Information

• Storage Condition: -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - R701700

Rupintrivir (formerly AG7088) is an irreversible inhibitor of the human rhinovirus (HRV) 3C protease that has been demonstrated to have in vitro activity against all HRVs tested, consistent with its interaction with a strictly conserved subset of amino ac

REFERENCES

• Arruda, E., et al.: J. Clin. Microbiol., 35, 2864 ( 1997), Dragovich, P., et al.: J. Med. Chem., 42, 1213 (1999)
• Kaiser, L., et al.: Antivir. Res., 47, 215 (1999)
• Binford, S., et al.: Antimicrob. Agents Chemother., 49, 619 (1999)
• Schmidtke, M., et al.: