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N-acetyl-beta-neuraminic acid


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Chemical Component Summary

NameN-acetyl-beta-neuraminic acid
SynonymsN-acetylneuraminic acid; sialic acid; O-sialic acid; 5-N-ACETYL-BETA-D-NEURAMINIC ACID; BETA-SIALIC ACID
Identifiers(2S,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, BETA 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-PFQGKNLYSA-N

Chemical Details

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

Drug Info: DrugBank

DrugBank IDDB04265 
NameN-acetyl-beta-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
  • beta-sialic acid
  • (-)-N-acetyl-beta-neuraminic acid
  • N-acetyl-beta-neuraminic acid
  • β-Neu5Ac
  • N-acetyl-beta-D-neuraminic acid
CAS number19342-33-7

Drug Targets

NameTarget SequencePharmacological ActionActions
Tetanus toxinMPITINNFRYSDPVNNDTIIMMEPPYCKGLDIYYKAFKITDRIWIVPERY...unknown
SialidaseMTANPYLRRLPRRRAVSFLLAPALAAATVAGASPAQAIAGAPVPPGGEPL...unknown
Endo-N-acetylneuraminidaseMSTITQFPSGNTQYRIEFDYLARTFVVVTLVNSSNPTLNRVLEVGRDYRF...unknown
Hemagglutinin-neuraminidaseMEYWKHTNHGKDAGNELETSMATHGNKLTNKIIYILWTIILVLLSIVFII...unknown
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 445063
ChEMBL CHEMBL165084
ChEBI CHEBI:45744