CHEBI:17012 - N-acetylneuraminic acid

Main ChEBI Ontology Automatic Xrefs Reactions Pathways Models
ChEBI Name N-acetylneuraminic acid
ChEBI ID CHEBI:17012
ChEBI ASCII Name N-acetylneuraminic acid
Definition An N-acylneuraminic acid where the N-acyl group is specified as acetyl.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:7214, CHEBI:21620, CHEBI:29087
Supplier Information No supplier information found for this compound.
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N-Acetylneuraminic acid (Neu5Ac or NANA) is the predominant sialic acid found in human cells, and many mammalian cells. Other forms, such as N-Glycolylneuraminic acid, may also occur in cells. This residue is negatively charged at physiological pH and is found in complex glycans on mucins and glycoproteins found at the cell membrane. Neu5Ac residues are also found in glycolipids, known as gangliosides, a crucial component of neuronal membranes found in the brain. Along with involvement in preventing infections (mucus associated with mucous membranes—mouth, nose, GI, respiratory tract), Neu5Ac acts as a receptor for influenza viruses, allowing attachment to mucous cells via hemagglutinin (an early step in acquiring influenzavirus infection).
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Formula C11H19NO9
Net Charge 0
Average Mass 309.26990
Monoisotopic Mass 309.10598
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-LUWBGTNYSA-N
SMILES [H][C@]1(OC(O)(C[C@H](O)[C@H]1NC(C)=O)C(O)=O)[C@H](O)[C@H](O)CO
Metabolite of Species Details
Mus musculus (NCBI:txid10090) Source: BioModels - MODEL1507180067 See: PubMed
Escherichia coli (NCBI:txid562) See: PubMed
Roles Classification
Chemical Role(s): antioxidant
A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides.
Biological Role(s): human metabolite
Any mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens).
bacterial metabolite
Any prokaryotic metabolite produced during a metabolic reaction in bacteria.
mouse metabolite
Any mammalian metabolite produced during a metabolic reaction in a mouse (Mus musculus).
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.
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.
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ChEBI Ontology
Outgoing N-acetylneuraminic acid (CHEBI:17012) has role antioxidant (CHEBI:22586)
N-acetylneuraminic acid (CHEBI:17012) has role bacterial metabolite (CHEBI:76969)
N-acetylneuraminic acid (CHEBI:17012) has role EC 3.2.1.18 (exo-α-sialidase) inhibitor (CHEBI:52425)
N-acetylneuraminic acid (CHEBI:17012) has role human metabolite (CHEBI:77746)
N-acetylneuraminic acid (CHEBI:17012) has role mouse metabolite (CHEBI:75771)
N-acetylneuraminic acid (CHEBI:17012) is a N-acetylneuraminic acids (CHEBI:21622)
N-acetylneuraminic acid (CHEBI:17012) is conjugate acid of N-acetylneuraminate (CHEBI:35418)
Incoming β-D-Galp-(1→9)-Neup5Ac (CHEBI:149010) has functional parent N-acetylneuraminic acid (CHEBI:17012)
3-acetamido-3,5-dideoxy-L-lyxo-hept-6-ulopyranosuronic acid (CHEBI:62323) has functional parent N-acetylneuraminic acid (CHEBI:17012)
5-acetamido-3,5-dideoxy-L-arabino-hept-2-ulopyranosonic acid (CHEBI:62322) has functional parent N-acetylneuraminic acid (CHEBI:17012)
9-deoxy-9-acetamido-N-acetyl-α-neuraminic acid (CHEBI:65188) has functional parent N-acetylneuraminic acid (CHEBI:17012)
N-acetylneuraminamide (CHEBI:62288) has functional parent N-acetylneuraminic acid (CHEBI:17012)
N-acetylneuraminol (CHEBI:62291) has functional parent N-acetylneuraminic acid (CHEBI:17012)
ethyl N-acetylneuraminate (CHEBI:62290) has functional parent N-acetylneuraminic acid (CHEBI:17012)
methyl N-acetylneuraminate (CHEBI:62303) has functional parent N-acetylneuraminic acid (CHEBI:17012)
N-acetyl-α-neuraminic acid (CHEBI:49026) is a N-acetylneuraminic acid (CHEBI:17012)
N-acetyl-β-neuraminic acid (CHEBI:45744) is a N-acetylneuraminic acid (CHEBI:17012)
N-acetylneuraminate (CHEBI:35418) is conjugate base of N-acetylneuraminic acid (CHEBI:17012)
N-acetylneuraminyl group (CHEBI:75133) is substituent group from N-acetylneuraminic acid (CHEBI:17012)
IUPAC Name
5-acetamido-3,5-dideoxy-D-glycero-D-galacto-non-2-ulopyranosonic acid
INNs Sources
aceneuramic acid ChemIDplus
acide aceneuramique ChemIDplus
acidium aceneuramicum ChemIDplus
acido aceneuramico ChemIDplus
Synonyms Sources
5-Acetamido-3,5-dideoxy-D-glycero-D-galacto-2-nonulosonic acid KEGG COMPOUND
Aceneuramic acid ChemIDplus
N-Acetylneuraminic acid KEGG COMPOUND
Neu5Ac KEGG COMPOUND
NeuAc ChEBI
O-sialic acid MetaCyc
WURCS=2.0/1,1,0/[Aad21122h-2x_2-6_5*NCC/3=O]/1/ GlyTouCan
Manual Xrefs Databases
C00019584 KNApSAcK
C00270 KEGG COMPOUND
G81533KY GlyTouCan
G81533KY GlyGen
N-acetylneuraminic_acid Wikipedia
View more database links
Registry Numbers Types Sources
131-48-6 CAS Registry Number KEGG COMPOUND
131-48-6 CAS Registry Number ChemIDplus
1398688 Reaxys Registry Number Reaxys
2951361 Beilstein Registry Number Beilstein
Citations Types Sources
14960498 PubMed citation Europe PMC
16209099 PubMed citation Europe PMC
16624269 PubMed citation Europe PMC
18487279 PubMed citation Europe PMC
19329108 PubMed citation Europe PMC
7508418 PubMed citation Europe PMC
8448384 PubMed citation Europe PMC
Last Modified
07 April 2021