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

• ChemBase ID: 154118
• Molecular Formular: C11H19NO10
• Molecular Mass: 325.26926
• Monoisotopic Mass: 325.10089581
• SMILES: C1[C@@H]([C@H]([C@@H](O[C@@]1(C(=O)O)O)[C@@H]([C@@H](CO)O)O)NC(=O)CO)O
• Canonical SMILES: OCC(=O)N[C@@H]1[C@@H](O)C[C@@](O[C@H]1[C@@H]([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-AJKRCSPLSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,4S,5R,6R)-2,4-dihydroxy-5-(2-hydroxyacetamido)-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid
• IUPAC Traditional name: N-glycolylneuraminic acid
• Synonyms: Neu5Glc; NeuNGl; N-Glycolylneuraminic acid

Database IDs

• CAS Number: 1113-83-3
• MDL Number: MFCD00057551
• Beilstein Number: 1716828
• PubChem SID: 24895382; 162248257; 24873386
• PubChem CID: 123802

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

Safety Information

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

Product Information

• Purity: ≥95% (HPLC)
• Biological Source: semisynthetic
• Empirical Formula (Hill Notation): C11H19NO10

DETAILS

Sigma Aldrich - 50644

Other Notes
Regulation of N-glycolylneuraminic acid biosynthesis in rat and mouse liver1
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Application
Glycolylneuraminic acid, a component of non-human milk and colostrums, is used as a reference to analyse changes of the glycome during lactation. Glycolylneuraminic acid, a xenoantigen, is involved in antigenic reactions (antibody-mediated hyperacute rejection) during xenotransplantion.