N-acetyl-beta-neuraminic acid (CHEBI:45744)

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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.

Supplier Information	ChemicalBook:CB6713403, eMolecules:713382, eMolecules:29543565, eMolecules:30152347, ZINC000003793840

Download	Molfile XML SDF

more structures >>

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2.9710 1.4562 -0.9536 C 0 0 0 0 0 0 0 0 0 0 0 0

1.9580 0.7646 -0.0790 C 0 0 1 0 0 0 0 0 0 0 0 0

2.4447 -0.6484 0.2455 C 0 0 0 0 0 0 0 0 0 0 0 0

1.4225 -1.3305 1.1619 C 0 0 1 0 0 0 0 0 0 0 0 0

0.0417 -1.2505 0.5024 C 0 0 2 0 0 0 0 0 0 0 0 0

-0.2633 0.2085 0.1574 C 0 0 2 0 0 0 0 0 0 0 0 0

-1.6544 0.3020 -0.4735 C 0 0 1 0 0 0 0 0 0 0 0 0

-1.9642 1.7623 -0.8104 C 0 0 1 0 0 0 0 0 0 0 0 0

-3.3554 1.8562 -1.4403 C 0 0 0 0 0 0 0 0 0 0 0 0

-1.2991 -3.0663 1.4193 C 0 0 0 0 0 0 0 0 0 0 0 0

-2.3437 -3.5886 2.3711 C 0 0 0 0 0 0 0 0 0 0 0 0

-0.9729 -1.7587 1.4273 N 0 0 0 0 0 0 0 0 0 0 0 0

2.6542 1.8466 -2.0530 O 0 0 0 0 0 0 0 0 0 0 0 0

4.2266 1.6368 -0.5144 O 0 0 0 0 0 0 0 0 0 0 0 0

1.7985 1.5024 1.1351 O 0 0 0 0 0 0 0 0 0 0 0 0

1.7840 -2.6994 1.3535 O 0 0 0 0 0 0 0 0 0 0 0 0

0.7072 0.7015 -0.7619 O 0 0 0 0 0 0 0 0 0 0 0 0

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-1.9295 2.5434 0.3850 O 0 0 0 0 0 0 0 0 0 0 0 0

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3.4091 -0.5950 0.7494 H 0 0 0 0 0 0 0 0 0 0 0 0

2.5454 -1.2189 -0.6775 H 0 0 0 0 0 0 0 0 0 0 0 0

1.3978 -0.8209 2.1247 H 0 0 0 0 0 0 0 0 0 0 0 0

0.0371 -1.8487 -0.4081 H 0 0 0 0 0 0 0 0 0 0 0 0

-0.2384 0.8063 1.0678 H 0 0 0 0 0 0 0 0 0 0 0 0

-2.3978 -0.0746 0.2276 H 0 0 0 0 0 0 0 0 0 0 0 0

-1.2208 2.1389 -1.5115 H 0 0 0 0 0 0 0 0 0 0 0 0

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1.4910 2.3855 0.8878 H 0 0 0 0 0 0 0 0 0 0 0 0

2.6571 -2.7026 1.7688 H 0 0 0 0 0 0 0 0 0 0 0 0

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1 2 1 0 0 0 0

1 13 2 0 0 0 0

1 14 1 0 0 0 0

2 3 1 0 0 0 0

2 15 1 0 0 0 0

2 17 1 0 0 0 0

3 4 1 0 0 0 0

3 22 1 0 0 0 0

3 23 1 0 0 0 0

4 5 1 0 0 0 0

4 16 1 0 0 0 0

4 24 1 0 0 0 0

5 6 1 0 0 0 0

5 12 1 0 0 0 0

5 25 1 0 0 0 0

6 7 1 0 0 0 0

6 17 1 0 0 0 0

6 26 1 0 0 0 0

7 8 1 0 0 0 0

7 18 1 0 0 0 0

7 27 1 0 0 0 0

8 9 1 0 0 0 0

8 19 1 0 0 0 0

8 28 1 0 0 0 0

9 20 1 0 0 0 0

9 29 1 0 0 0 0

9 30 1 0 0 0 0

10 11 1 0 0 0 0

10 12 1 0 0 0 0

10 21 2 0 0 0 0

11 31 1 0 0 0 0

11 32 1 0 0 0 0

11 33 1 0 0 0 0

12 34 1 0 0 0 0

14 35 1 0 0 0 0

15 36 1 0 0 0 0

16 37 1 0 0 0 0

18 38 1 0 0 0 0

19 39 1 0 0 0 0

20 40 1 0 0 0 0

M END): 19 ms

reading 40 atoms

ModelSet: haveSymmetry:false haveUnitcells:false haveFractionalCoord:false

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Default Van der Waals type for model set to Babel

40 atoms created

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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-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-(acetylamino)-3,5-dideoxy-D-glycero-β-D-galacto-2-nonulopyranosonic acid	ChEBI
5-N-ACETYL-BETA-D-NEURAMINIC ACID	PDBeChem
β-Neu5Ac	ChEBI
D-glycero-β-D-galacto-2-nonulopyranosonic acid, 5-(acetylamino)-3,5-dideoxy-	ChEBI
WURCS=2.0/1,1,0/[Aad21122h-2b_2-6_5*NCC/3=O]/1/	GlyTouCan

Manual Xrefs	Databases
G76571JT	GlyGen
G76571JT	GlyTouCan
SLB	PDBeChem
View more database links

Registry Number	Type	Source
8134650	Reaxys Registry Number	Reaxys

Citations

Bello-Gil D, Olivera-Ardid S, Tuzikov AB, Costa C, Bovin NV, Mañez R (2023)
Antibodies against hyaluronan oligosaccharides in xenotransplantation.
Xenotransplantation 30, e12799 [PubMed:36988069]
[show Abstract]

Jandus P, Boligan KF, Smith DF, de Graauw E, Grimbacher B, Jandus C, Abdelhafez MM, Despont A, Bovin N, Simon D, Rieben R, Simon HU, Cummings RD, von Gunten S (2019)
The architecture of the IgG anti-carbohydrate repertoire in primary antibody deficiencies.
Blood 134, 1941-1950 [PubMed:31537530]
[show Abstract]

Hurh S, Kang B, Choi I, Cho B, Lee EM, Kim H, Kim YJ, Chung YS, Jeong JC, Hwang JI, Kim JY, Lee BC, Surh CD, Yang J, Ahn C (2016)
Human antibody reactivity against xenogeneic N-glycolylneuraminic acid and galactose-α-1,3-galactose antigen.
Xenotransplantation 23, 279-292 [PubMed:27373998]
[show Abstract]

Schneider C, Smith DF, Cummings RD, Boligan KF, Hamilton RG, Bochner BS, Miescher S, Simon HU, Pashov A, Vassilev T, von Gunten S (2015)
The human IgG anti-carbohydrate repertoire exhibits a universal architecture and contains specificity for microbial attachment sites.
Science translational medicine 7, 269ra1 [PubMed:25568069]
[show Abstract]

von Gunten S, Smith DF, Cummings RD, Riedel S, Miescher S, Schaub A, Hamilton RG, Bochner BS (2009)
Intravenous immunoglobulin contains a broad repertoire of anticarbohydrate antibodies that is not restricted to the IgG2 subclass.
The Journal of allergy and clinical immunology 123, 1268-76.e15 [PubMed:19443021]
[show Abstract]

Li LS, Wu YL, Wu Y (2000)
Total synthesis of fully acetylated N-acetylneuraminic acid (Neu5Ac), 2-deoxy-beta-Neu5Ac, and 4-epi-2-deoxy-beta-Neu5Ac from D-glucose
Organic letters 2, 891-894 [PubMed:10768179]
[show Abstract]

Deijl CM, Vliegenthart JF (1983)
Configuration of substrate and products of N-acetylneuraminate pyruvate-lyase from Clostridium perfringens.
Biochemical and biophysical research communications 111, 668-674 [PubMed:6301475]
[show Abstract]

Last Modified

29 March 2024

ChEBI

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

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Background

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