CMP-N-acetyl-beta-neuraminic acid (CHEBI:16556)

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CHEBI:16556 - CMP-N-acetyl-β-neuraminic acid

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ChEBI Name	CMP-N-acetyl-β-neuraminic acid

ChEBI ID	CHEBI:16556

ChEBI ASCII Name	CMP-N-acetyl-beta-neuraminic acid

Definition	A nucleotide sugar used as a donor by glycosyltransferases for the synthesis of sugar chains

Stars	This entity has been manually annotated by the ChEBI Team.

Submitter	Bijay

Secondary ChEBI IDs	CHEBI:44441, CHEBI:3278, CHEBI:13279, CHEBI:13276, CHEBI:20875, CHEBI:59434

Supplier Information	ZINC000008215638

Download	Molfile XML SDF

more structures >>

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M END): 19 ms

reading 72 atoms

ModelSet: haveSymmetry:false haveUnitcells:false haveFractionalCoord:false

1 model in this collection. Use getProperty "modelInfo" or getProperty "auxiliaryInfo" to inspect them.

Default Van der Waals type for model set to Babel

72 atoms created

ModelSet: not autobonding; use forceAutobond=true to force automatic bond creation

Script completed

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Molfile expand

Formula

C20H31N4O16P

Net Charge

Average Mass

614.45126

Monoisotopic Mass

614.14727

InChI

InChI=1S/C20H31N4O16P/c1-7(26)22-12-8(27)4-20(18(32)33,39-16(12)13(29)9(28)5-25)40-41(35,36)37-6-10-14(30)15(31)17(38-10)24-3-2-11(21)23-19(24)34/h2-3,8-10,12-17,25,27-31H,4-6H2,1H3,(H,22,26)(H,32,33)(H,35,36)(H2,21,23,34)/t8-,9+,10+,12+,13+,14+,15+,16+,17+,20+/m0/s1

InChIKey

TXCIAUNLDRJGJZ-BILDWYJOSA-N

SMILES

[H][C@]1(O[C@](C[C@H](O)[C@H]1NC(C)=O)(OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1O)n1ccc(N)nc1=O)C(O)=O)[C@H](O)[C@H](O)CO

Metabolite of Species	Details
Mus musculus (NCBI:txid10090)	Source: BioModels - MODEL1507180067 See: PubMed

Roles Classification
Biological Role(s):	mouse metabolite Any mammalian metabolite produced during a metabolic reaction in a mouse (Mus musculus).

View more via ChEBI Ontology

ChEBI Ontology
Outgoing	CMP-N-acetyl-β-neuraminic acid (CHEBI:16556) has functional parent N-acetyl-β-neuraminic acid (CHEBI:45744) CMP-N-acetyl-β-neuraminic acid (CHEBI:16556) has role mouse metabolite (CHEBI:75771) CMP-N-acetyl-β-neuraminic acid (CHEBI:16556) is a CMP-N-acyl-β-neuraminic acid (CHEBI:16788) CMP-N-acetyl-β-neuraminic acid (CHEBI:16556) is conjugate acid of CMP-N-acetyl-β-neuraminate(2−) (CHEBI:57812)

Incoming	CMP-N-acetyl-β-neuraminate(2−) (CHEBI:57812) is conjugate base of CMP-N-acetyl-β-neuraminic acid (CHEBI:16556)

IUPAC Name

cytidine 5'-(5-acetamido-3,5-dideoxy-D-glycero-β-D-galacto-non-2-ulopyranosylonic acid monophosphate)

Synonyms	Sources
CMP acetylneuraminic acid	ChemIDplus
CMP-β-Neu5Ac	IUPAC
CMP-N-acetylneuraminate	KEGG COMPOUND
Cmp-nana	ChemIDplus
CMP-Neu5Ac	ChEBI
CMP-NeuNAc	ChEBI
CMP-sialic acid	ChEBI
cytidine monophosphate N-acetylneuraminic acid	ChemIDplus
CYTIDINE-5'-MONOPHOSPHATE-5-N-ACETYLNEURAMINIC ACID	PDBeChem
cytidine-5'-monophospho-N-acetylneuraminic acid	ChEBI
cytidine-5'-monophosphono-N-acetylneuraminic acid	ChEBI

Manual Xrefs	Databases
C00128	KEGG COMPOUND
DB02485	DrugBank
G10616	KEGG GLYCAN
NCC	PDBeChem
View more database links

Registry Numbers	Types	Sources
3063-71-6	CAS Registry Number	ChemIDplus
4224251	Reaxys Registry Number	Reaxys

Citation

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]

Last Modified

12 September 2016

ChEBI

CHEBI:16556 - CMP-N-acetyl-β-neuraminic acid

Background

Methods

Results

Conclusions

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