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

• ChemBase ID: 155219
• Molecular Formular: C11H17NO8
• Molecular Mass: 291.25458
• Monoisotopic Mass: 291.09541651
• SMILES: CC(=O)N[C@@H]1[C@H](C=C(O[C@H]1[C@@H]([C@@H](CO)O)O)C(=O)O)O
• Canonical SMILES: OC[C@H]([C@H]([C@@H]1OC(=C[C@@H]([C@H]1NC(=O)C)O)C(=O)O)O)O
• InChI: InChI=1S/C11H17NO8/c1-4(14)12-8-5(15)2-7(11(18)19)20-10(8)9(17)6(16)3-13/h2,5-6,8-10,13,15-17H,3H2,1H3,(H,12,14)(H,18,19)/t5-,6+,8+,9+,10+/m0/s1
• InChIKey: JINJZWSZQKHCIP-UFGQHTETSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3R,4S)-3-acetamido-4-hydroxy-2-[(1R,2R)-1,2,3-trihydroxypropyl]-3,4-dihydro-2H-pyran-6-carboxylic acid
• IUPAC Traditional name: (4S,5R,6R)-5-acetamido-4-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]-5,6-dihydro-4H-pyran-2-carboxylic acid
• Synonyms: 2,3-Dehydro-2-deoxy-N-acetylneuraminic acid; N-Acetyl-2,3-dehydro-2-deoxyneuraminic acid

Database IDs

• CAS Number: 24967-27-9
• EC Number: 246-550-7
• MDL Number: MFCD00135810
• Beilstein Number: 8722455
• PubChem SID: 162249357; 24894248
• PubChem CID: 65309

CALCULATED PROPERTIES

• Acid pKa: 3.4996006
• H Acceptors: 8
• H Donor: 6
• LogD (pH = 5.5): -5.7101603
• LogD (pH = 7.4): -7.0726485
• Log P: -3.688152
• Molar Refractivity: 64.1107 cm^3
• Polarizability: 25.284155 Å^3
• Polar Surface Area: 156.55 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C; 2-8°C

Product Information

• Purity: ~95% (TLC); ≥93%
• Quality Level: PREMIUM
• Empirical Formula (Hill Notation): C11H17NO8

DETAILS

Sigma Aldrich - D9050

Biochem/physiol Actions
Inhibitor of bacterial, viral and animal neuraminidase (sialidase).1,2
Application
N-Acetyl-2,3-dehydro-2-deoxyneuraminic acid (NADNA) is used to study the effects of blocking endogenous neuraminidase on neural activity.

Sigma Aldrich - 01060

Biochem/physiol Actions
Inhibitor of bacterial, viral and animal neuraminidase (sialidase).1,2
Other Notes
Inhibitor of bacterial, viral and animal neuraminidase1