N-acetyl-alpha-neuraminic acid (CHEBI:49026)

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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

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Formula

C11H19NO9

Net Charge

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-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 )

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
5-(acetylamino)-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosonic acid	ChEBI
α-Neu5Ac	ChEBI
D-glycero-α-D-galacto-2-nonulopyranosonic acid, 5-(acetylamino)-3,5-dideoxy-	ChEBI
O-SIALIC ACID	PDBeChem
WURCS=2.0/1,1,0/[Aad21122h-2a_2-6_5*NCC/3=O]/1/	GlyTouCan

Last Modified

27 March 2024