CHEBI:45744 - N-acetyl-β-neuraminic acid

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ChEBI Name N-acetyl-β-neuraminic acid
ChEBI ID CHEBI:45744
ChEBI ASCII Name N-acetyl-beta-neuraminic acid
Definition N-Acetylneuraminic acid with β configuration at the anomeric centre.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C11H19NO9
Net Charge 0
Average Mass 309.26990
Monoisotopic Mass 309.106
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
InChIKey SQVRNKJHWKZAKO-PFQGKNLYSA-N
SMILES [H][C@]1(O[C@@](O)(C[C@H](O)[C@H]1NC(C)=O)C(O)=O)[C@H](O)[C@H](O)CO
Roles Classification
Chemical Role(s): antioxidant
A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides.
(via N-acetylneuraminic acid )
Biological Role(s): epitope
The biological role played by a material entity when bound by a receptor of the adaptive immune system. Specific site on an antigen to which an antibody binds.
human metabolite
Any mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens).
(via N-acetylneuraminic acid )
bacterial metabolite
Any prokaryotic metabolite produced during a metabolic reaction in bacteria.
(via N-acetylneuraminic acid )
mouse metabolite
Any mammalian metabolite produced during a metabolic reaction in a mouse (Mus musculus).
(via N-acetylneuraminic acid )
EC 3.2.1.18 (exo-alpha-sialidase) inhibitor
An antiviral drug targeted at influenza viruses. Its mode of action consists of blocking the function of the viral neuraminidase protein (EC 3.2.1.18), thus preventing the virus from budding from the host cell.
(via N-acetylneuraminic acid )
Application(s): EC 3.2.1.18 (exo-alpha-sialidase) inhibitor
An antiviral drug targeted at influenza viruses. Its mode of action consists of blocking the function of the viral neuraminidase protein (EC 3.2.1.18), thus preventing the virus from budding from the host cell.
(via N-acetylneuraminic acid )
View more via ChEBI Ontology
ChEBI Ontology
Outgoing N-acetyl-β-neuraminic acid (CHEBI:45744) has functional parent β-neuraminic acid (CHEBI:49022)
N-acetyl-β-neuraminic acid (CHEBI:45744) has role epitope (CHEBI:53000)
N-acetyl-β-neuraminic acid (CHEBI:45744) is a N-acetylneuraminic acid (CHEBI:17012)
N-acetyl-β-neuraminic acid (CHEBI:45744) is conjugate acid of N-acetyl-β-neuraminate (CHEBI:58705)
Incoming CMP-N-acetyl-β-neuraminic acid (CHEBI:16556) has functional parent N-acetyl-β-neuraminic acid (CHEBI:45744)
N-acetyl-β-neuraminate (CHEBI:58705) is conjugate base of N-acetyl-β-neuraminic acid (CHEBI:45744)
IUPAC Name
5-acetamido-3,5-dideoxy-D-glycero-β-D-galacto-non-2-ulopyranosonic acid
Synonyms Sources
5-N-ACETYL-BETA-D-NEURAMINIC ACID PDBeChem
β-Neu5Ac ChEBI
Database Link Database
SLB PDBeChem
View more database links
Registry Numbers Types Sources
8134650 Beilstein Registry Number Beilstein
8134650 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
10768179 PubMed citation Europe PMC
19443021 PubMed citation Europe PMC
25568069 PubMed citation Europe PMC
27373998 PubMed citation Europe PMC
6301475 PubMed citation Europe PMC
Last Modified
12 September 2016