5-acetamido-4-hydroxy-2-methoxy-6-(1,2,3-trihydroxypropyl)oxane-2-carboxylic acid

• ChemBase ID: 155338
• Molecular Formular: C12H21NO9
• Molecular Mass: 323.29644
• Monoisotopic Mass: 323.12163126
• SMILES: CC(=O)NC1C(CC(OC1C(C(CO)O)O)(C(=O)O)OC)O
• Canonical SMILES: OCC(C(C1OC(OC)(CC(C1NC(=O)C)O)C(=O)O)O)O
• InChI: InChI=1S/C12H21NO9/c1-5(15)13-8-6(16)3-12(21-2,11(19)20)22-10(8)9(18)7(17)4-14/h6-10,14,16-18H,3-4H2,1-2H3,(H,13,15)(H,19,20)
• InChIKey: NJRVVFURCKKXOD-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-acetamido-4-hydroxy-2-methoxy-6-(1,2,3-trihydroxypropyl)oxane-2-carboxylic acid
• IUPAC Traditional name: 5-acetamido-4-hydroxy-2-methoxy-6-(1,2,3-trihydroxypropyl)oxane-2-carboxylic acid
• Synonyms: α-D-Neu-5-Ac-2→OCH3; 2-O-Methyl-α-D-N-acetylneuraminic acid

Database IDs

• CAS Number: 50930-22-8
• MDL Number: MFCD00084809
• PubChem SID: 162249476; 24897007
• PubChem CID: 5067510

CALCULATED PROPERTIES

• Acid pKa: 3.0656354
• H Acceptors: 9
• H Donor: 6
• LogD (pH = 5.5): -5.3233356
• LogD (pH = 7.4): -6.387094
• Log P: -2.920811
• Molar Refractivity: 68.5326 cm^3
• Polarizability: 28.118418 Å^3
• Polar Surface Area: 165.78 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• German water hazard class: 3
• Storage Temperature: -20°C

Product Information

• Purity: ~95% (TLC)
• Empirical Formula (Hill Notation): C12H21NO9

DETAILS

Sigma Aldrich - M6405

Application
Model compound for studies of binding of influenza virus hemagglutinin1 and metal ions.2