CHEBI:49026 - N-acetyl-α-neuraminic acid

Main ChEBI Ontology Automatic Xrefs Reactions Pathways Models
ChEBI Name N-acetyl-α-neuraminic acid
ChEBI ID CHEBI:49026
ChEBI ASCII Name N-acetyl-alpha-neuraminic acid
Definition N-Acetylneuraminic acid with α configuration at the anomeric centre.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:45493, CHEBI:49025
Supplier Information
Download Molfile XML SDF
more structures >>
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-YRMXFSIDSA-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-α-neuraminic acid (CHEBI:49026) has functional parent α-neuraminic acid (CHEBI:49024)
N-acetyl-α-neuraminic acid (CHEBI:49026) has role epitope (CHEBI:53000)
N-acetyl-α-neuraminic acid (CHEBI:49026) is a N-acetylneuraminic acid (CHEBI:17012)
N-acetyl-α-neuraminic acid (CHEBI:49026) is conjugate acid of N-acetyl-α-neuraminate (CHEBI:58770)
Incoming N-acetyl-α-neuraminyl-(2→6)-N-acetyl-α-D-galactosamine (CHEBI:61818) has functional parent N-acetyl-α-neuraminic acid (CHEBI:49026)
N-acetyl-α-neuraminate (CHEBI:58770) is conjugate base of N-acetyl-α-neuraminic acid (CHEBI:49026)
IUPAC Name
5-acetamido-3,5-dideoxy-D-glycero-α-D-galacto-non-2-ulopyranosonic acid
Synonyms Sources
α-Neu5Ac ChEBI
O-SIALIC ACID PDBeChem
Manual Xrefs Databases
DB03721 DrugBank
SIA PDBeChem
View more database links
Registry Numbers Types Sources
1689968 Beilstein Registry Number Beilstein
1689968 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
19443021 PubMed citation Europe PMC
25568069 PubMed citation Europe PMC
Last Modified
11 February 2015