SIA

N-acetyl-alpha-neuraminic acid



Chemical Component Summary

NameN-acetyl-alpha-neuraminic acid
SynonymsN-acetylneuraminic acid; sialic acid; alpha-sialic acid; O-SIALIC ACID
Identifiers(2R,4S,5R,6R)-5-acetamido-2,4-dihydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid
FormulaC11 H19 N O9
Molecular Weight309.27
TypeD-SACCHARIDE, ALPHA LINKING
Isomeric SMILESCC(=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
InChIInChI=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
InChIKeySQVRNKJHWKZAKO-YRMXFSIDSA-N

Chemical Details

Formal Charge0
Atom Count40
Chiral Atom Count6
Bond Count40
Aromatic Bond Count0

Drug Info: DrugBank

DrugBank IDDB03721 
NameN-acetyl-alpha-neuraminic acid
Groups experimental
DescriptionAn N-acyl derivative of neuraminic acid. N-acetylneuraminic acid occurs in many polysaccharides, glycoproteins, and glycolipids in animals and bacteria. (From Dorland, 28th ed, p1518)
Synonyms
  • O-sialic acid
  • α-Neu5Ac
  • N-Acetyl-alpha-D-neuraminic acid
  • N-acetyl-alpha-neuraminic acid
CAS number21646-00-4

Drug Targets

NameTarget SequencePharmacological ActionActions
3-deoxy-manno-octulosonate cytidylyltransferaseMSKAVIVIPARYGSSRLPGKPLLDIVGKPMIQHVYERALQVAGVAEVWVA...unknown
Tetanus toxinMPITINNFRYSDPVNNDTIIMMEPPYCKGLDIYYKAFKITDRIWIVPERY...unknown
Cholera enterotoxin subunit BMIKLKFGVFFTVLLSSAYAHGTPQNITDLCAEYHNTQIYTLNDKIFSYTE...unknown
Botulinum neurotoxin type BMPVTINNFNYNDPIDNNNIIMMEPPFARGTGRYYKAFKITDRIWIIPERY...unknown
P-selectinMANCQIAILYQRFQRVVFGISQLLCFSALISELTNQKEVAAWTYHYSTKA...unknown
View More
Drug Info/Drug Targets: DrugBank 3.0: a comprehensive resource for 'omics' research on drugs. Knox C, Law V, Jewison T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS. Nucleic Acids Res. 2011 Jan; 39 (Database issue):D1035-41. | PMID:21059682

Related Resource References

Resource NameReference
PubChem 444885
ChEMBL CHEMBL1234621
ChEBI CHEBI:61599, CHEBI:49026