(2S,4S,5R,6R)-5-amino-2,4-dihydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid

• ChemBase ID: 128581
• Molecular Formular: C9H17NO8
• Molecular Mass: 267.23318
• Monoisotopic Mass: 267.09541651
• SMILES: O=C(O)[C@@]1(O)O[C@@H]([C@H](O)[C@H](O)CO)[C@H](N)[C@@H](O)C1
• Canonical SMILES: OC[C@H]([C@H]([C@@H]1O[C@@](O)(C[C@@H]([C@H]1N)O)C(=O)O)O)O
• InChI: InChI=1S/C9H17NO8/c10-5-3(12)1-9(17,8(15)16)18-7(5)6(14)4(13)2-11/h3-7,11-14,17H,1-2,10H2,(H,15,16)/t3-,4+,5+,6+,7+,9-/m0/s1
• InChIKey: CERZMXAJYMMUDR-YOQZMRDMSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,4S,5R,6R)-5-amino-2,4-dihydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid
• IUPAC Traditional name: β-neuraminic acid
• Synonyms: Neuraminic acid

Database IDs

• CAS Number: 114-04-5
• PubChem SID: 162222888
• PubChem CID: 513472
• CHEBI ID: 49022
• CHEMBL: 165084
• Chemspider ID: 447972
• MeSH Name: Neuraminic+Acids
• Wikipedia Title: Neuraminic_acid

CALCULATED PROPERTIES

• Acid pKa: 2.7245193
• H Acceptors: 9
• H Donor: 7
• LogD (pH = 5.5): -5.646465
• LogD (pH = 7.4): -5.699217
• Log P: -5.647269
• Molar Refractivity: 54.3376 cm^3
• Polarizability: 22.814499 Å^3
• Polar Surface Area: 173.7 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: false