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Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2016-02-11 01:03:57 UTC
HMDB IDHMDB01176
Secondary Accession Numbers
  • HMDB01040
Metabolite Identification
Common NameCytidine monophosphate N-acetylneuraminic acid
DescriptionCytidine monophosphate N-acetylneuraminic acid is a nucleoside monophosphate sugar which donates N-acetylneuraminic acid to the terminal sugar of a ganglioside or glycoprotein.
Structure
Thumb
Synonyms
ValueSource
CMP-beta-Neu5acChEBI
CMP-N-AcetylneuraminateChEBI
CMP-Sialic acidChEBI
Cytidine monophosphate N-acetylneuraminic acidChEBI
CYTIDINE-5'-monophosphATE-5-N-acetylneuraminIC ACIDChEBI
CMP-b-Neu5acGenerator
CMP-β-neu5acGenerator
CMP-N-AcylneuraminateHMDB
CMP-NeuNAcHMDB
Cytidine 5'-monophosphate N-acetylneuraminic acidHMDB
Cytidine monophosphate N-acetylneuraminateHMDB
Chemical FormulaC20H31N4O16P
Average Molecular Weight614.4511
Monoisotopic Molecular Weight614.147267476
IUPAC Name(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
Traditional Namecmp-sialic acid
CAS Registry Number22-12-8
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)N1C=CC(N)=NC1=O)C(O)=O)[C@H](O)[C@H](O)CO
InChI Identifier
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
InChI KeyInChIKey=TXCIAUNLDRJGJZ-BILDWYJOSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as pyrimidine nucleotide sugars. These are pyrimidine nucleotides bound to a saccharide derivative through the terminal phosphate group.
KingdomOrganic compounds
Super ClassNucleosides, nucleotides, and analogues
ClassPyrimidine nucleotides
Sub ClassPyrimidine nucleotide sugars
Direct ParentPyrimidine nucleotide sugars
Alternative Parents
Substituents
  • Pyrimidine nucleotide sugar
  • N-acylneuraminic acid or derivatives
  • N-acylneuraminic acid
  • Pyrimidine ribonucleoside monophosphate
  • Neuraminic acid
  • Pyranoid amino acid
  • C-glucuronide
  • Amino sugar
  • N-glycosyl compound
  • Glycosyl compound
  • C-glycosyl compound
  • Monosaccharide phosphate
  • Pyran carboxylic acid
  • Pyran carboxylic acid or derivatives
  • Dialkyl phosphate
  • Amino saccharide
  • Pyrimidone
  • Aminopyrimidine
  • Imidolactam
  • Alkyl phosphate
  • Pyrimidine
  • Pyran
  • Primary aromatic amine
  • Phosphoric acid ester
  • Oxane
  • Organic phosphoric acid derivative
  • Organic phosphate
  • Monosaccharide
  • Hydropyrimidine
  • Heteroaromatic compound
  • Acetamide
  • Oxolane
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Polyol
  • Carboxamide group
  • 1,2-diol
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Carboxylic acid amide
  • Hydrocarbon derivative
  • Primary amine
  • Primary alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Amine
  • Alcohol
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
Biofunction
  • Component of Aminosugars metabolism
ApplicationNot Available
Cellular locations
  • Cytoplasm
  • Nucleus
  • Golgi apparatus
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility36.3 mg/mLALOGPS
logP-2.7ALOGPS
logP-5.9ChemAxon
logS-1.2ALOGPS
pKa (Strongest Acidic)1.48ChemAxon
pKa (Strongest Basic)-0.77ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count16ChemAxon
Hydrogen Donor Count10ChemAxon
Polar Surface Area320.69 Å2ChemAxon
Rotatable Bond Count11ChemAxon
Refractivity125.42 m3·mol-1ChemAxon
Polarizability54.33 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
  • Nucleus
  • Golgi apparatus
Biofluid LocationsNot Available
Tissue LocationNot Available
Pathways
NameSMPDB LinkKEGG Link
Amino Sugar MetabolismSMP00045map00520
G(M2)-Gangliosidosis: Variant B, Tay-sachs diseaseSMP00534Not Available
Salla Disease/Infantile Sialic Acid Storage DiseaseSMP00240Not Available
Sialuria or French Type SialuriaSMP00216Not Available
Sialuria or French Type SialuriaSMP00217Not Available
Tay-Sachs DiseaseSMP00390Not Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB022466
KNApSAcK IDNot Available
Chemspider ID395082
KEGG Compound IDC00128
BioCyc IDCMP-N-ACETYL-NEURAMINATE
BiGG ID33954
Wikipedia LinkNot Available
NuGOwiki LinkHMDB01176
Metagene LinkHMDB01176
METLIN ID6057
PubChem Compound448209
PDB IDNCC
ChEBI ID16556
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Involved in sialyltransferase activity
Specific function:
Catalyzes the formation of the NeuAc-alpha-2,3-Gal-beta-1,4-GlcNAc-, NeuAc-alpha-2,3-Gal-beta-1,3-GlcNAc- or NeuAc-alpha-2,3-Gal-beta-1,3-GalNAc- sequences found in terminal carbohydrate groups of glycoproteins and glycolipids. The highest activity is toward Gal-beta-1,3-GlcNAc and the lowest toward Gal-beta-1,3-GalNAc (By similarity).
Gene Name:
ST3GAL3
Uniprot ID:
Q11203
Molecular weight:
38741.57
Reactions
Cytidine monophosphate N-acetylneuraminic acid + beta-D-galactosyl-(1->4)-N-acetyl-D-glucosaminyl-glycoprotein → Cytidine monophosphate + alpha-N-acetylneuraminyl-(2->3)-beta-D-galactosyl-(1->4)-N-acetyl-D-glucosaminyl-glycoproteindetails
General function:
Involved in sialyltransferase activity
Specific function:
Involved in the production of gangliosides GD3 and GT3 from GM3; gangliosides are a subfamily of complex glycosphinglolipds that contain one or more residues of sialic acid.
Gene Name:
ST8SIA1
Uniprot ID:
Q92185
Molecular weight:
40518.655
Reactions
Cytidine monophosphate N-acetylneuraminic acid + alpha-N-acetylneuraminyl-(2->3)-beta-D-galactosyl-R → Cytidine monophosphate + alpha-N-acetylneuraminyl-(2->8)-alpha-N-acetylneuraminyl-(2->3)-beta-D-galactosyl-Rdetails
General function:
Involved in lipopolysaccharide biosynthetic process
Specific function:
Catalyzes the activation of N-acetylneuraminic acid (NeuNAc) to cytidine 5'-monophosphate N-acetylneuraminic acid (CMP-NeuNAc), a substrate required for the addition of sialic acid. Has some activity toward NeuNAc, N-glycolylneuraminic acid (Neu5Gc) or 2-keto-3-deoxy-D-glycero-D-galacto-nononic acid (KDN).
Gene Name:
CMAS
Uniprot ID:
Q8NFW8
Molecular weight:
48378.835
Reactions
Cytidine triphosphate + N-acylneuraminate → Pyrophosphate + Cytidine monophosphate N-acetylneuraminic aciddetails
Cytidine triphosphate + N-Acetylneuraminic acid → Pyrophosphate + Cytidine monophosphate N-acetylneuraminic aciddetails
General function:
Involved in sialyltransferase activity
Specific function:
Catalyzes the formation of ganglioside GM3 (alpha-N-acetylneuraminyl-2,3-beta-D-galactosyl-1, 4-beta-D-glucosylceramide).
Gene Name:
ST3GAL5
Uniprot ID:
Q9UNP4
Molecular weight:
45584.69
Reactions
Cytidine monophosphate N-acetylneuraminic acid + beta-D-galactosyl-(1->4)-beta-D-glucosyl-(1<->1)-ceramide → Cytidine monophosphate + alpha-N-acetylneuraminyl-(2->3)-beta-D-galactosyl-(1->4)-beta-D-glucosyl-(1<->1)-ceramidedetails
General function:
Involved in sialyltransferase activity
Specific function:
Involved in the synthesis of sialyl-paragloboside, a precursor of sialyl-Lewis X determinant. Has a alpha-2,3- sialyltransferase activity toward Gal-beta1,4-GlcNAc structure on glycoproteins and glycolipids. Has a restricted substrate specificity, it utilizes Gal-beta1,4-GlcNAc on glycoproteins, and neolactotetraosylceramide and neolactohexaosylceramide, but not lactotetraosylceramide, lactosylceramide or asialo-GM1
Gene Name:
ST3GAL6
Uniprot ID:
Q9Y274
Molecular weight:
38213.3
General function:
Involved in beta-galactoside alpha-2,3-sialyltransferas
Specific function:
It may be responsible for the synthesis of the sequence NeuAc-alpha-2,3-Gal-beta-1,3-GalNAc- found on sugar chains O-linked to Thr or Ser and also as a terminal sequence on certain gangliosides. SIAT4A and SIAT4B sialylate the same acceptor substrates but exhibit different Km values.
Gene Name:
ST3GAL1
Uniprot ID:
Q11201
Molecular weight:
39074.745
Reactions
Cytidine monophosphate N-acetylneuraminic acid + beta-D-galactosyl-1,3-N-acetyl-alpha-D-galactosaminyl-R → Cytidine monophosphate + alpha-N-acetylneuraminyl-2,3-beta-D-galactosyl-1,3-N-acetyl-alpha-D-galactosaminyl-Rdetails
General function:
Involved in sialyltransferase activity
Specific function:
It may catalyze the formation of the NeuAc-alpha-2,3-Gal-beta-1,3-GalNAc- or NeuAc-alpha-2,3-Gal-beta-1,3-GlcNAc-sequences found in terminal carbohydrate groups of glycoproteins and glycolipids. It may be involved in the biosynthesis of the sialyl Lewis X determinant. Also acts on the corresponding 1,3-galactosyl derivative.
Gene Name:
ST3GAL4
Uniprot ID:
Q11206
Molecular weight:
38045.1
Reactions
Cytidine monophosphate N-acetylneuraminic acid + beta-D-galactosyl-1,4-N-acetyl-D-glucosaminyl-glycoprotein → Cytidine monophosphate + alpha-N-acetylneuraminyl-2,3-beta-D-galactosyl-1,4-N-acetyl-D-glucosaminyl-glycoproteindetails
General function:
Not Available
Specific function:
Involved in the biosynthesis of ganglioside GD1A from GM1B. Transfers CMP-NeuAc with an alpha-2,6-linkage to GalNAc residue on NeuAc-alpha-2,3-Gal-beta-1,3-GalNAc of glycoproteins and glycolipids. Prefers glycoproteins to glycolipids (By similarity).
Gene Name:
ST6GALNAC4
Uniprot ID:
Q9H4F1
Molecular weight:
34200.255
Reactions
Cytidine monophosphate N-acetylneuraminic acid + N-acetyl-alpha-neuraminyl-(2->3)-beta-D-galactosyl-(1->3)-N-acetyl-D-galactosaminyl-R → Cytidine monophosphate + N-acetyl-alpha-neuraminyl-(2->3)-beta-D-galactosyl-(1->3)-(N-acetyl-alpha-neuraminyl-(2->6))-N-acetyl-D-galactosaminyl-Rdetails
General function:
Not Available
Specific function:
It may be responsible for the synthesis of the sequence NeuAc-alpha-2,3-Gal-beta-1,3-GalNAc- found in terminal carbohydrate groups of certain glycoproteins, oligosaccharides and glycolipids. SIAT4A and SIAT4B sialylate the same acceptor substrates but exhibit different Km values.
Gene Name:
ST3GAL2
Uniprot ID:
Q16842
Molecular weight:
40172.565
Reactions
Cytidine monophosphate N-acetylneuraminic acid + beta-D-galactosyl-1,3-N-acetyl-alpha-D-galactosaminyl-R → Cytidine monophosphate + alpha-N-acetylneuraminyl-2,3-beta-D-galactosyl-1,3-N-acetyl-alpha-D-galactosaminyl-Rdetails
General function:
Not Available
Specific function:
Not Available
Gene Name:
ST6GALNAC1
Uniprot ID:
Q9NSC7
Molecular weight:
68563.845
Reactions
Cytidine monophosphate N-acetylneuraminic acid + glycano-(1->3)-(N-acetyl-alpha-D-galactosaminyl)-glycoprotein → Cytidine monophosphate + glycano-((2->6)-alpha-N-acetylneuraminyl)-(N-acetyl-D-galactosaminyl)-glycoproteindetails
General function:
Not Available
Specific function:
Not Available
Gene Name:
ST6GALNAC2
Uniprot ID:
Q9UJ37
Molecular weight:
41938.815
Reactions
Cytidine monophosphate N-acetylneuraminic acid + glycano-beta-D-galactosyl-1,3-(N-acetyl-D-galactosaminyl)-glycoprotein → Cytidine monophosphate + glycano-beta-D-galactosyl-(2,6-alpha-N-acetylneuraminyl)-(N-acetyl-D-galactosaminyl)-glycoproteindetails
General function:
Not Available
Specific function:
Involved in the biosynthesis of ganglioside GD1A from GM1B. Transfers CMP-NeuAc with an alpha-2,6-linkage to GalNAc residue on NeuAc-alpha-2,3-Gal-beta-1,3-GalNAc of glycoproteins and glycolipids. ST6GalNAcIII prefers glycolipids to glycoproteins (By similarity).
Gene Name:
ST6GALNAC3
Uniprot ID:
Q8NDV1
Molecular weight:
24021.865
Reactions
Cytidine monophosphate N-acetylneuraminic acid + alpha-N-acetylneuraminyl-2,3-beta-D-galactosyl-1,3-(N-acetyl-D-galactosaminyl)-glycoprotein → Cytidine monophosphate + alpha-N-acetylneuraminyl-2,3-beta-D-galactosyl-(2,6-alpha-N-acetylneuraminyl)-(N-acetyl-D-galactosaminyl)-glycoproteindetails
General function:
Not Available
Specific function:
Transfers sialic acid from the donor of substrate CMP-sialic acid to galactose containing acceptor substrates.
Gene Name:
ST6GAL1
Uniprot ID:
P15907
Molecular weight:
46604.235
Reactions
Cytidine monophosphate N-acetylneuraminic acid + beta-D-galactosyl-1,4-N-acetyl-beta-D-glucosamine → Cytidine monophosphate + (N-acetylneuraminosyl(a2-6)lactosamine)details
General function:
Not Available
Specific function:
Transfers sialic acid from the donor of substrate CMP-sialic acid to galactose containing acceptor substrates. Has alpha-2,6-sialyltransferase activity toward oligosaccharides that have the Gal-beta-1,4-GlcNAc sequence at the non-reducing end of their carbohydrate groups, but it has weak or no activities toward glycoproteins and glycolipids.
Gene Name:
ST6GAL2
Uniprot ID:
Q96JF0
Molecular weight:
60157.39
Reactions
Cytidine monophosphate N-acetylneuraminic acid + beta-D-galactosyl-1,4-N-acetyl-beta-D-glucosamine → Cytidine monophosphate + (N-acetylneuraminosyl(a2-6)lactosamine)details