(2R,3R,4S)-4-carbamimidamido-3-acetamido-2-[(1S,2R)-2-hydroxy-1-methoxy-3-(octanoyloxy)propyl]-3,4-dihydro-2H-pyran-6-carboxylic acid

• ChemBase ID: 172195
• Molecular Formular: C21H36N4O8
• Molecular Mass: 472.53254
• Monoisotopic Mass: 472.25331413
• SMILES: C1=C(O[C@H]([C@@H]([C@H]1NC(=N)N)NC(=O)C)[C@H]([C@@H](COC(=O)CCCCCCC)O)OC)C(=O)O
• Canonical SMILES: CCCCCCCC(=O)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/C21H36N4O8/c1-4-5-6-7-8-9-16(28)32-11-14(27)18(31-3)19-17(24-12(2)26)13(25-21(22)23)10-15(33-19)20(29)30/h10,13-14,17-19,27H,4-9,11H2,1-3H3,(H,24,26)(H,29,30)(H4,22,23,25)/t13-,14+,17+,18-,19+/m0/s1
• InChIKey: UKTIJASCFRNWCB-JCZGSWPSSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3R,4S)-4-carbamimidamido-3-acetamido-2-[(1S,2R)-2-hydroxy-1-methoxy-3-(octanoyloxy)propyl]-3,4-dihydro-2H-pyran-6-carboxylic acid
• IUPAC Traditional name: (4S,5R,6R)-4-carbamimidamido-5-acetamido-6-[(1S,2R)-2-hydroxy-1-methoxy-3-(octanoyloxy)propyl]-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 9-Octanoate; (2R,3R,4S)-3-Acetamido-4-guanidino-2-[(1R,2R)-2-hydroxy-1-methoxy-3-(octanoyloxy)propyl]-3,4-dihydro-2H-pyran-6-carboxylic Acid; (4S,5R,6R)-5-Acetamido-4-guanidino-6-[(1R,2R)-2-hydroxy-1-methoxy-3-(octanoyloxy)propyl]-5,6-dihydro-4H-pyran-2-carboxylic Acid; CS 8958; Laninamivir Octanoate

Database IDs

• CAS Number: 203120-46-1
• PubChem SID: 164228105
• PubChem CID: 12071753

CALCULATED PROPERTIES

• Acid pKa: 3.4489121
• H Acceptors: 10
• H Donor: 6
• LogD (pH = 5.5): -1.7692896
• LogD (pH = 7.4): -1.7661563
• Log P: -1.7661742
• Molar Refractivity: 128.0174 cm^3
• Polarizability: 46.12899 Å^3
• Polar Surface Area: 193.29 Å^2
• Rotatable Bonds: 15
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - L174010

Laninamivir (L174000) prodrug; a novel long-acting neuraminidase inhibitor.

REFERENCES

• Neumann, G., et al.: Nature, 459, 931 (2009)
• Yamashita, M., et al.: Antimicrob. Agents Chemother., 53, 186 (2009)