N-Acetylneuraminic acid

N-Acetylneuraminic acid
β anomer
Names
IUPAC name
5-(Acetylamino)-3,5-dideoxy-D-glycero-α-D-galacto-non-2-ulopyranosonic acid
Other names
  • NANA
  • Neu5Ac
  • Aceneuramic acid
  • Acenobel
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.004.568 Edit this at Wikidata
KEGG
MeSH N-Acetylneuraminic+Acid
UNII
  • 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 checkY
    Key: SQVRNKJHWKZAKO-YRMXFSIDSA-N checkY
  • InChI=1/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
    Key: SQVRNKJHWKZAKO-YRMXFSIDBI
  • OC(=O)[C@@]1(O)C[C@H](O)[C@@H](NC(C)=O)[C@@H](O1)[C@H](O)[C@H](O)CO
Properties
C11H19NO9
Molar mass 309.271 g·mol−1
Appearance White crystalline powder
Melting point 186 °C (367 °F; 459 K) (decomposes)
Pharmacology
M09AX05 (WHO)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)

N-Acetylneuraminic acid (Neu5Ac or NANA) is the predominant sialic acid found in human cells, and many mammalian cells. Other forms, such as N-Glycolylneuraminic acid, may also occur in cells.

This residue is negatively charged at physiological pH and is found in complex glycans on mucins and glycoproteins found at the cell membrane. Neu5Ac residues are also found in glycolipids, known as gangliosides, a crucial component of neuronal membranes found in the brain.

Along with involvement in preventing infections (mucus associated with mucous membranes—mouth, nose, GI, respiratory tract), Neu5Ac acts as a receptor for influenza viruses, allowing attachment to mucous cells via hemagglutinin (an early step in acquiring influenzavirus infection).