(2R,3R,4S)-4-carbamimidamido-2-[(1S,2R)-2,3-dihydroxy-1-methoxypropyl]-3-acetamido-3,4-dihydro-2H-pyran-6-carboxylic acid

• ChemBase ID: 172193
• Molecular Formular: C13H22N4O7
• Molecular Mass: 346.33638
• Monoisotopic Mass: 346.14884906
• SMILES: C1=C(O[C@H]([C@@H]([C@H]1NC(=N)N)NC(=O)C)[C@H]([C@@H](CO)O)OC)C(=O)O
• Canonical SMILES: OC[C@H]([C@@H]([C@@H]1OC(=C[C@@H]([C@H]1NC(=O)C)NC(=N)N)C(=O)O)OC)O
• InChI: InChI=1S/C13H22N4O7/c1-5(19)16-9-6(17-13(14)15)3-8(12(21)22)24-11(9)10(23-2)7(20)4-18/h3,6-7,9-11,18,20H,4H2,1-2H3,(H,16,19)(H,21,22)(H4,14,15,17)/t6-,7+,9+,10-,11+/m0/s1
• InChIKey: QNRRHYPPQFELSF-NVDALUKASA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3R,4S)-4-carbamimidamido-2-[(1S,2R)-2,3-dihydroxy-1-methoxypropyl]-3-acetamido-3,4-dihydro-2H-pyran-6-carboxylic acid
• IUPAC Traditional name: (4S,5R,6R)-4-carbamimidamido-6-[(1S,2R)-2,3-dihydroxy-1-methoxypropyl]-5-acetamido-5,6-dihydro-4H-pyran-2-carboxylic acid
• Synonyms: 5-(Acetylamino)-4-[(aminoiminomethyl)amino]-2,6-anhydro-3,4,5-trideoxy-7-O-methyl-D-glycero-D-galacto-Non-2-enonic Acid; (4S,5R,6R)-5-Acetamido-4-guanidino-6-((1R,2R)-2,3-dihydroxy-1-methoxypropyl)-5,6-dihydro-4H-pyran-2-carboxylic Acid; R 125489; Laninamivir

Database IDs

• CAS Number: 203120-17-6
• PubChem SID: 164228103
• PubChem CID: 71749736

CALCULATED PROPERTIES

• Acid pKa: 3.6169033
• H Acceptors: 10
• H Donor: 7
• LogD (pH = 5.5): -5.135289
• LogD (pH = 7.4): -5.1306763
• Log P: -5.130669
• Molar Refractivity: 91.234 cm^3
• Polarizability: 31.364876 Å^3
• Polar Surface Area: 187.22 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - L174000

A new potent neuraminidase (NA) inhibitor, shows long-acting anti-influenza virus activity.

REFERENCES

• Bantia, S., et al.: Antimicrob. Agents Chemother., 42, 801 (1998)
• Honda, T., et al.: Bioorg. Med. Chem. Lett., 12, 1925 (1998)
• Kiso, M., et al.: Lancet, 364, 759 (1998)
• Macdonald, S., et al.: J. Med. Chem., 48, 2964 (1998)