(1S,2S,3R,4R)-4-carbamimidamido-3-[(1R)-1-acetamido-2-ethylbutyl]-2-hydroxycyclopentane-1-carboxylic acid

• ChemBase ID: 176360
• Molecular Formular: C15H28N4O4
• Molecular Mass: 328.40722
• Monoisotopic Mass: 328.2110554
• SMILES: C1[C@H]([C@@H]([C@@H]([C@H]1C(=O)O)O)[C@@H](C(CC)CC)NC(=O)C)NC(=N)N
• Canonical SMILES: CCC([C@H]([C@H]1[C@H](NC(=N)N)C[C@@H]([C@H]1O)C(=O)O)NC(=O)C)CC
• InChI: InChI=1S/C15H28N4O4/c1-4-8(5-2)12(18-7(3)20)11-10(19-15(16)17)6-9(13(11)21)14(22)23/h8-13,21H,4-6H2,1-3H3,(H,18,20)(H,22,23)(H4,16,17,19)/t9-,10+,11+,12+,13+/m0/s1
• InChIKey: XRQDFNLINLXZLB-ZOLYEBIHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2S,3R,4R)-4-carbamimidamido-3-[(1R)-1-acetamido-2-ethylbutyl]-2-hydroxycyclopentane-1-carboxylic acid
• IUPAC Traditional name: (1S,2S,3R,4R)-4-carbamimidamido-3-[(1R)-1-acetamido-2-ethylbutyl]-2-hydroxycyclopentane-1-carboxylic acid
• Synonyms: (1S,2S,3R,4R)-3-[(1S)-1-(Acetylamino)-2-ethylbutyl]-4-[(aminoiminomethyl)amino]-2-hydroxycyclopentanecarboxylic Acid; BCX 1812; RWJ 270201; Peramivir

Database IDs

• CAS Number: 330600-85-6
• PubChem SID: 164232270
• PubChem CID: 9883907

CALCULATED PROPERTIES

• Acid pKa: 4.183867
• H Acceptors: 7
• H Donor: 6
• LogD (pH = 5.5): -2.1383579
• LogD (pH = 7.4): -2.121641
• Log P: -2.1214879
• Molar Refractivity: 94.4604 cm^3
• Polarizability: 33.063732 Å^3
• Polar Surface Area: 148.53 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - P285500

A new antiviral agent for influenza treatment; it can be used as neuraminidase inhibitor for treating human and avian influenza.

REFERENCES

• Whitley, R., et al.: Pediatr. Infect. Dis. J., 20, 127 (2001)
• Bright, R., et al.: Lancet., 366, 1175 (2001)
• Deyde, V., et al.: J. Infect. Dis., 196, 249 (2001)
• Lee, N., et al.: Clin. Infect. Dis., 46, 1323 (2001)