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

• ChemBase ID: 179621
• Molecular Formular: C12H20N4O7
• Molecular Mass: 332.3098
• Monoisotopic Mass: 332.133199
• SMILES: C1=C(O[C@H]([C@@H]([C@H]1NC(=N)N)NC(=O)C)[C@@H]([C@@H](CO)O)O)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)O)O
• InChI: InChI=1S/C12H20N4O7/c1-4(18)15-8-5(16-12(13)14)2-7(11(21)22)23-10(8)9(20)6(19)3-17/h2,5-6,8-10,17,19-20H,3H2,1H3,(H,15,18)(H,21,22)(H4,13,14,16)/t5-,6+,8+,9+,10+/m0/s1
• InChIKey: ARAIBEBZBOPLMB-UFGQHTETSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3R,4S)-4-carbamimidamido-3-acetamido-2-[(1R,2R)-1,2,3-trihydroxypropyl]-3,4-dihydro-2H-pyran-6-carboxylic acid
• IUPAC Traditional name: relenza
• Synonyms: 5-(Acetylamino)-4-[(aminoiminomethyl)amino]-2,6-anhydro-3,4,5-trideoxy-D-glycero-D-galacto-non-2-enonic Acid; GANA; 4-Guanidino-2,4-dideoxy-2,3-dehydro-N-acetylneuraminic Acid; 4-Guanidino-Neu5Ac2en; GR 121167X; Relenza; Zanamir; Zanamivir; 139110-80-8; Zanamivir (Relenza)

Database IDs

• CAS Number: 139110-80-8
• PubChem SID: 164235531
• PubChem CID: 60855

CALCULATED PROPERTIES

• Acid pKa: 3.556214
• H Acceptors: 10
• H Donor: 8
• LogD (pH = 5.5): -5.7778087
• LogD (pH = 7.4): -5.7737956
• Log P: -5.773796
• Molar Refractivity: 86.4828 cm^3
• Polarizability: 29.490557 Å^3
• Polar Surface Area: 198.22 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Water
• Apperance: White Solid
• Melting Point: >245°C (dec.)

Safety Information

• Storage Condition: -20°C Freezer

Pharmacology Properties

• Target: Others

Product Information

• Salt Data: Free Base

DETAILS

Toronto Research Chemicals - Z148000

Influenza viral neuraminidase inhibitor; structural analog of the sialic acid. Antiviral.

REFERENCES

• Woods, J.M., et al.: Antimicrob. Agents Chemother., 37, 1473 (1993)
• Pegg, M.S., et al.: Biochem. Mol. Biol. Int., 32, 851 (1993)
• Monto, A.S., et al.: J. Am. Med. Assoc., 282, 31 (1993)