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

• ChemBase ID: 169693
• Molecular Formular: C11H19NO10
• Molecular Mass: 325.26926
• Monoisotopic Mass: 325.10089581
• SMILES: [C@@H]1([C@@H]([C@@H](C[C@@](O1)(O)C(=O)O)O)NC(=O)CO)C([C@@H](CO)O)O
• Canonical SMILES: OCC(=O)N[C@@H]1[C@H](O)C[C@@](O[C@H]1C([C@@H](CO)O)O)(O)C(=O)O
• InChI: InChI=1S/C11H19NO10/c13-2-5(16)8(18)9-7(12-6(17)3-14)4(15)1-11(21,22-9)10(19)20/h4-5,7-9,13-16,18,21H,1-3H2,(H,12,17)(H,19,20)/t4-,5+,7+,8?,9+,11-/m0/s1
• InChIKey: FDJKUWYYUZCUJX-GETJOPHTSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,4S,5R,6R)-2,4-dihydroxy-5-(2-hydroxyacetamido)-6-[(2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid
• IUPAC Traditional name: (2S,4S,5R,6R)-2,4-dihydroxy-5-(2-hydroxyacetamido)-6-[(2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid
• Synonyms: N-(2-Hydroxyacetyl)neuraminic Acid; 3,5-Dideoxy-5-[(hydroxyacetyl)amino]-D-glycero-D-galacto-2-nonulosonic Acid; Glycolylneuraminic Acid; N-Glycolyl Neuraminic Acid

Database IDs

• CAS Number: 1113-83-3
• PubChem SID: 162263825
• PubChem CID: 71317108

CALCULATED PROPERTIES

• Acid pKa: 2.9169607
• H Acceptors: 10
• H Donor: 8
• LogD (pH = 5.5): -6.918813
• LogD (pH = 7.4): -7.864933
• Log P: -4.3811855
• Molar Refractivity: 65.4836 cm^3
• Polarizability: 26.97869 Å^3
• Polar Surface Area: 197.01 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Water
• Apperance: White Crystalline Solid
• Melting Point: 188-190°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - G650000

Regulation of N-glycolylneuraminic acid biosynthesis in rat and mouse liver.

REFERENCES

• Malykh, Y., et al.: Biochimie, 83, 623 (2001)
• Angata, T., et al.: Chem. Rev., 102, 439 (2001)
• Soh, N., et al.: Anal. Sci., 18, 1159 (2001)
• Taylor, P., et al.: Clin. Biochem., 38, 328 (2001)