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

• ChemBase ID: 165966
• Molecular Formular: C9H16O9
• Molecular Mass: 268.21794
• Monoisotopic Mass: 268.07943209
• SMILES: [C@@H]1([C@@H]([C@@H](C[C@@](O1)(O)C(=O)O)O)O)[C@H]([C@@H](CO)O)O
• Canonical SMILES: OC[C@H]([C@@H]([C@@H]1O[C@@](O)(C[C@H]([C@H]1O)O)C(=O)O)O)O
• InChI: InChI=1S/C9H16O9/c10-2-4(12)6(14)7-5(13)3(11)1-9(17,18-7)8(15)16/h3-7,10-14,17H,1-2H2,(H,15,16)/t3-,4+,5+,6+,7+,9-/m0/s1
• InChIKey: CLRLHXKNIYJWAW-YOQZMRDMSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,4S,5R,6R)-2,4,5-trihydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid
• IUPAC Traditional name: (2S,4S,5R,6R)-2,4,5-trihydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid
• Synonyms: KDN; 3-Deoxy-D-glycero-D-galacto-2-nonulosonic Acid

Database IDs

• CAS Number: 153666-19-4
• PubChem SID: 162260099
• PubChem CID: 10869261

CALCULATED PROPERTIES

• Rotatable Bonds: 4
• Lipinski's Rule of Five: false
• Acid pKa: 2.892075
• H Acceptors: 9
• H Donor: 7
• LogD (pH = 5.5): -5.8357577
• LogD (pH = 7.4): -6.7620726
• Log P: -3.2759023
• Molar Refractivity: 52.6801 cm^3
• Polarizability: 22.021454 Å^3
• Polar Surface Area: 167.91 Å^2

PROPERTIES

Physical Property

• Solubility: Water
• Apperance: White to Off-White Solid
• Melting Point: 26-28°C

Safety Information

• Storage Condition: Hygroscopic, -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - D239500

A naturally occuring deaminated sialic acid, exclusively located at the non-reducing end of the sialyl chains.

REFERENCES

• Nadano, D., et al.: J. Biol. Chem., 261, 11550 (1986)