Specification
Description
N-Acetylneuraminic acid is a nine-carbon, sialic acid monosaccharide commonly found in glycoproteins on cell membranes and in glycolipids such as gangliosides in mammalian cells. Studies suggest that N-Acetylneuraminic acid is useful biologically in neurotransmission, leukocyte extravasation, viral or bacterial infections and carbohydrate-protein recognition.
Synonyms
Galactononulosonic acid
IUPAC Name
(2S,4S,5R,6R)-5-Acetamido-2,4-dihydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid
Canonical SMILES
CC(=O)NC1C(CC(OC1C(C(CO)O)O)(C(=O)O)O)O
InChI
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-PFQGKNLYSA-N
Isomeric SMILES
CC(=O)N[C@@H]1[C@H](C[C@](O[C@H]1[C@@H]([C@@H](CO)O)O)(C(=O)O)O)O
Monoisotopic Mass
309.10598118
Refractive Index
-32 ° (C=1, H₂O)
Solubility In Water
50 g/L (20 ºC)
Stability
Stable. Incompatible with strong oxidizing agents.
Topological Polar Surface Area
177 Ų