Page last updated: 2024-12-06

cytidine monophosphate n-acetylneuraminic acid

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth

Description

Cytidine Monophosphate N-Acetylneuraminic Acid: A nucleoside monophosphate sugar which donates N-acetylneuraminic acid to the terminal sugar of a ganglioside or glycoprotein. [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

CMP-N-acetyl-beta-neuraminic acid : A nucleotide sugar used as a donor by glycosyltransferases for the synthesis of sugar chains [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Cross-References

ID SourceID
PubMed CID448209
CHEMBL ID1234647
CHEBI ID16556
SCHEMBL ID122854
MeSH IDM0005576

Synonyms (41)

Synonym
CHEMBL1234647
cmp-sialic acid
cytidine-5'-monophosphono-n-acetylneuraminic acid
CHEBI:16556 ,
cytidine-5'-monophospho-n-acetylneuraminic acid
cytidine monophosphate n-acetylneuraminic acid
cmp-n-acetyl-beta-neuraminic acid
cmp-neunac
cmp-beta-neu5ac
cytidine 5'-(5-acetamido-3,5-dideoxy-d-glycero-beta-d-galacto-non-2-ulopyranosylonic acid monophosphate)
cytidine-5'-monophosphate-5-n-acetylneuraminic acid
NCC ,
cmp-n-acetylneuraminate
C00128
cmp-n-acylneuraminate
DB02485
(2r,4s,5r,6r)-5-acetamido-2-[[(2r,3s,4r,5r)-5-(4-amino-2-oxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-4-hydroxy-6-[(1r,2r)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid
cmp-d-n-acetylneuraminic acid
cytidine-5'-monophospho 5-acetamido-3,5-dideoxy-d-glycero-beta-d-galacto-2-nonulopyranosonic acid
gtpl4663
(2r,4s,5r,6r)-2-[({[(2r,3s,4r,5r)-5-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]-5-acetamido-4-hydroxy-6-[(1r,2r)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid
SCHEMBL122854
22-12-8
cytidine 5'-monophosphate n-acetylneuraminic acid
cytidine monophosphate n-acetylneuraminate
cytidine 5'-monophosphate-n-acetylneuraminic acid
(2r,4s,5r)-5-acetamido-2-((((2r,3s,4r,5r)-5-(4-amino-2-oxopyrimidin-1(2h)-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methoxy)(hydroxy)phosphoryloxy)-4-hydroxy-6-((1r,2r)-1,2,3-trihydroxypropyl)tetrahydro-2h-pyran-2-carboxylic acid
(2r,4s,5r,6r)-5-(acetylamino)-2-{[(s)-{[(2r,3s,4r,5r)-5-(4-amino-2-oxopyrimidin-1(2h)-yl)-3,4-dihydroxytetrahydrofuran-2-yl]methoxy}(hydroxy)phosphoryl]oxy}-4-hydroxy-6-[(1r,2r)-1,2,3-trihydroxypropyl]tetrahydro-2h-pyran-2-carboxylic acid (non-preferred n
TXCIAUNLDRJGJZ-BILDWYJOSA-N
Q27076132
cytidine 5'-monophospho-n-
(2r,4s,5r,6r)-5-acetamido-2-(((((2r,3s,4r,5r)-5-(4-amino-2-oxopyrimidin-1(2h)-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methoxy)(hydroxy)phosphoryl)oxy)-4-hydroxy-6-((1r,2r)-1,2,3-trihydroxypropyl)tetrahydro-2h-pyran-2-carboxylic acid
n-acetyl-.beta.-neuraminic acid 2-(hydrogen 5'-cytidylate)
.beta.-neuraminic acid, n-acetyl-, 2-(hydrogen 5'-cytidylate)
(2s,4s,5s,6s)-5-acetamido-2-(((2r,3s,4s,5r)-5-(4-azanyl-2-oxidanylidene-pyrimidin-1-yl)-3,4-bis(oxidanyl)oxolan-2-yl)methoxy-oxidanyl-phosphoryl)oxy-4-oxidanyl-6-((1s,2s)-1,2,3-tris(oxidanyl)propyl)oxane-2-carboxylic acid
neuraminic acid, n-acetyl-, 2-ester with 5'-cytidylic acid
cmp-neu5ac; cmp-sialic acid, monosodium salt
cytidine-5-monophospho-n-acetylneuraminic acid
CS-0069697
F76225
HY-112942
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (1)

RoleDescription
mouse metaboliteAny mammalian metabolite produced during a metabolic reaction in a mouse (Mus musculus).
[role information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Drug Classes (1)

ClassDescription
CMP-N-acyl-beta-neuraminic acidA CMP-sugar in which the sugar component consists of any N-acyl-beta-neuraminic acid.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Pathways (8)

PathwayProteinsCompounds
Amino Sugar Metabolism1731
Sialuria or French Type Sialuria1731
Salla Disease/Infantile Sialic Acid Storage Disease1731
Tay-Sachs Disease1731
G(M2)-Gangliosidosis: Variant B, Tay-Sachs Disease1731
Aminosugars metabolism ( Aminosugars metabolism )1529
SARS-CoV-1 Infection6019
SARS-CoV-2 Infection7720

Protein Targets (1)

Other Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (11)

Processvia Protein(s)Taxonomy
N-acetylneuraminate metabolic processBeta-galactoside alpha-2,6-sialyltransferase 1Homo sapiens (human)
humoral immune responseBeta-galactoside alpha-2,6-sialyltransferase 1Homo sapiens (human)
O-glycan processingBeta-galactoside alpha-2,6-sialyltransferase 1Homo sapiens (human)
protein N-linked glycosylation via asparagineBeta-galactoside alpha-2,6-sialyltransferase 1Homo sapiens (human)
viral protein processingBeta-galactoside alpha-2,6-sialyltransferase 1Homo sapiens (human)
positive regulation of mononuclear cell proliferationBeta-galactoside alpha-2,6-sialyltransferase 1Homo sapiens (human)
response to ethanolBeta-galactoside alpha-2,6-sialyltransferase 1Homo sapiens (human)
negative regulation of chemotaxisBeta-galactoside alpha-2,6-sialyltransferase 1Homo sapiens (human)
sialylationBeta-galactoside alpha-2,6-sialyltransferase 1Homo sapiens (human)
regulation of substrate adhesion-dependent cell spreadingBeta-galactoside alpha-2,6-sialyltransferase 1Homo sapiens (human)
negative regulation of macrophage apoptotic processBeta-galactoside alpha-2,6-sialyltransferase 1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (4)

Processvia Protein(s)Taxonomy
beta-galactoside alpha-2,6-sialyltransferase activityBeta-galactoside alpha-2,6-sialyltransferase 1Homo sapiens (human)
protein bindingBeta-galactoside alpha-2,6-sialyltransferase 1Homo sapiens (human)
sialyltransferase activityBeta-galactoside alpha-2,6-sialyltransferase 1Homo sapiens (human)
protein homodimerization activityBeta-galactoside alpha-2,6-sialyltransferase 1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (6)

Processvia Protein(s)Taxonomy
Golgi trans cisternaBeta-galactoside alpha-2,6-sialyltransferase 1Homo sapiens (human)
Golgi membraneBeta-galactoside alpha-2,6-sialyltransferase 1Homo sapiens (human)
extracellular regionBeta-galactoside alpha-2,6-sialyltransferase 1Homo sapiens (human)
Golgi medial cisternaBeta-galactoside alpha-2,6-sialyltransferase 1Homo sapiens (human)
Golgi cisterna membraneBeta-galactoside alpha-2,6-sialyltransferase 1Homo sapiens (human)
Golgi apparatusBeta-galactoside alpha-2,6-sialyltransferase 1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (4)

Assay IDTitleYearJournalArticle
AID74253Inhibitory concentration at which there is accumulation of UDP-[3H]-GlcNAc in the lumen of the Golgi membranes.1996Journal of medicinal chemistry, Jul-19, Volume: 39, Issue:15
Inhibition of UDP-N-acetylglucosamine import into Golgi membranes by nucleoside monophosphates.
AID74259In vitro inhibition of UDP-[3H]-GlcNAc import into the lumen of the Golgi membranes from rabbit liver homogenate.1996Journal of medicinal chemistry, Jul-19, Volume: 39, Issue:15
Inhibition of UDP-N-acetylglucosamine import into Golgi membranes by nucleoside monophosphates.
AID1720632Binding affinity to recombinant human N-terminal 6His-tagged ST6Gal-1 (Glu44 to Cys406 residues)2020Bioorganic & medicinal chemistry, 07-15, Volume: 28, Issue:14
Design, synthesis and evaluation of carbamate-linked uridyl-based inhibitors of human ST6Gal I.
AID1853252Substrate activity at recombinant human ST6Gal I incubated for 1 hrs in the presence of LacNAc as acceptor by luminescence based CMP-Glo assay2021RSC medicinal chemistry, Oct-20, Volume: 12, Issue:10
Synthesis and biological evaluation of selective phosphonate-bearing 1,2,3-triazole-linked sialyltransferase inhibitors.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (278)

TimeframeStudies, This Drug (%)All Drugs %
pre-199090 (32.37)18.7374
1990's88 (31.65)18.2507
2000's63 (22.66)29.6817
2010's28 (10.07)24.3611
2020's9 (3.24)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials1 (0.36%)5.53%
Reviews14 (5.02%)6.00%
Case Studies3 (1.08%)4.05%
Observational0 (0.00%)0.25%
Other261 (93.55%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]