Showing Metabocard for N-acetyl-alpha-neuraminate (BASm0003699)
| Common Name | N-acetyl-alpha-neuraminate |
|---|---|
| Description | N-Acetyl-alpha-neuraminate is a sialic acid. Sialic acids are an important family of related 9-carbon sugars acids, present on the surface of many different cells and functioning in a wide range of different biological processes. They mediate a variety of cell-cell and cell-molecule interactions in eukaryotes and can be utilized by pathogens to evade the host immune response. N-acetylneuraminic acid is the most common sialic acid, and the predominant form present in humans. It can be found as a terminal sugar on a wide range of surface glycoconjugates. A number of bacteria that can colonize humans (such as E. coli) make use of N-acetylneuraminic acid as a nutrient source. |
| Structure | |
| Molecular Formula | C11H19NO9 |
| Average Mass | 309.26990 |
| Monoisotopic Mass | 309.10598 |
| IUPAC Name | (2R,4S,5R,6R)-5-acetamido-2,4-dihydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid |
| Traditional Name | N-acetylneuraminic acid |
| CAS Registry Number | 21646-00-4 |
| SMILES | CC(=O)N[C@H]1[C@H]([C@H](O)[C@H](O)CO)O[C@@](O)(C(=O)[O-])C[C@@H]1O |
| InChI Identifier | InChI=1S/C11H19NO9/c1-4(14)12-7-5(15)2-11(20,10(18)19)21-9(7)8(17)6(16)3-13/h5-9,13,15-17,20H,2-3H2,1H3,(H,12,14)(H,18,19)/t5-,6+,7+,8+,9+,11+/m0/s1 |
| InChI Key | SQVRNKJHWKZAKO-YRMXFSIDSA-N |
| CHEBI ID | CHEBI:58770 |
| HMDB ID | HMDB0000773 |
| State | Solid |
| Water Solubility | 2.27e+02 g/l |
| logP | -2.78 |
| logS | -0.13 |
| pKa (Strongest Acidic) | 3.00 |
| pKa (Strongest Basic) | -0.38 |
| Hydrogen Acceptor Count | 9 |
| Hydrogen Donor Count | 7 |
| Polar Surface Area | 176.78 Ų |
| Rotatable Bond Count | 5 |
| Physiological Charge | -1 |
| Formal Charge | 0 |
| Refractivity | 63.78 m³·mol⁻¹ |
| Polarizability | 27.95 |