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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2017-12-20 20:29:37 UTC
HMDB IDHMDB0001176
Secondary Accession Numbers
  • HMDB0001040
  • HMDB01040
  • HMDB01176
Metabolite Identification
Common NameCytidine monophosphate N-acetylneuraminic acid
DescriptionCytidine monophosphate n-acetylneuraminic acid, also known as cmp-N-acetylneuraminate or cmp-nana, is a member of the class of compounds known as pyrimidine nucleotide sugars. Pyrimidine nucleotide sugars are pyrimidine nucleotides bound to a saccharide derivative through the terminal phosphate group. Cytidine monophosphate n-acetylneuraminic acid is soluble (in water) and a moderately acidic compound (based on its pKa). Within the cell, cytidine monophosphate n-acetylneuraminic acid is primarily located in the cytoplasm, in the nucleus and in the golgi apparatus. Cytidine monophosphate n-acetylneuraminic acid exists in all living organisms, ranging from bacteria to humans. In humans, cytidine monophosphate n-acetylneuraminic acid is involved in the amino sugar metabolism. Cytidine monophosphate n-acetylneuraminic acid is also involved in few metabolic disorders, which include g(m2)-gangliosidosis: variant B, tay-sachs disease, salla disease/infantile sialic acid storage disease, sialuria or french type sialuria, and tay-sachs disease. Cytidine 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-5'-monophosphATE-5-N-acetylneuraminIC ACIDChEBI
CMP-b-Neu5acGenerator
CMP-β-neu5acGenerator
Cytidine monophosphate N-acetylneuraminateGenerator
Cytidine monophosphoric acid N-acetylneuraminic acidGenerator
CMP-N-Acetylneuraminic acidGenerator
CMP-SialateGenerator
CYTIDINE-5'-monophosphate-5-N-acetylneuraminateGenerator
CYTIDINE-5'-monophosphoric acid-5-N-acetylneuraminic acidGenerator
CMP-N-AcylneuraminateHMDB
CMP-NeuNAcHMDB
Cytidine 5'-monophosphate N-acetylneuraminic acidHMDB
Acetylneuraminic acid, CMPMeSH
Acid, CMP acetylneuraminicMeSH
Acid, CMP-sialicMeSH
CMP Acetylneuraminic acidMeSH
CMP Sialic acidMeSH
CMP-NANAMeSH
Cytidine monophosphate N acetylneuraminic acidMeSH
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 KeyTXCIAUNLDRJGJZ-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
  • Pyrimidine ribonucleoside monophosphate
  • N-acylneuraminic acid
  • N-acylneuraminic acid or derivatives
  • Neuraminic acid
  • Pentose phosphate
  • Pentose-5-phosphate
  • C-glucuronide
  • C-glycosyl compound
  • Glycosyl compound
  • N-glycosyl compound
  • Monosaccharide phosphate
  • Aminopyrimidine
  • Pyrimidone
  • Dialkyl phosphate
  • Hydropyrimidine
  • Monosaccharide
  • Organic phosphoric acid derivative
  • Oxane
  • Phosphoric acid ester
  • Pyran
  • Pyrimidine
  • Imidolactam
  • Alkyl phosphate
  • Tetrahydrofuran
  • Acetamide
  • Heteroaromatic compound
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Amino acid
  • Amino acid or derivatives
  • Polyol
  • Organoheterocyclic compound
  • Azacycle
  • Carboxylic acid derivative
  • Carboxylic acid
  • Oxacycle
  • Monocarboxylic acid or derivatives
  • Organopnictogen compound
  • Organic oxide
  • Carbonyl group
  • Organic oxygen compound
  • Primary amine
  • Alcohol
  • Primary alcohol
  • Hydrocarbon derivative
  • Amine
  • Organic nitrogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Disposition

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

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 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count11ChemAxon
Refractivity125.42 m³·mol⁻¹ChemAxon
Polarizability54.33 ųChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-01ot-9512160000-178f009287639a11dbfdView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-044l-9624017000-8c596d9b4644a97fbb65View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0912020000-9d330aadc1882c503212View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-3902000000-b2c85490ddb7f53db6f4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03di-6910000000-a8d1f94c4661e1dd3097View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-4813091000-d68fb03c5bbe9978f2e5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-4912010000-168821fb3a4dc5a309b1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-08fr-9310000000-5e2455827ac9cc8b0a87View in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
  • Nucleus
  • Golgi apparatus
Biospecimen LocationsNot Available
Tissue LocationNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB022466
KNApSAcK IDNot Available
Chemspider ID395082
KEGG Compound IDC00128
BioCyc IDCMP-N-ACETYL-NEURAMINATE
BiGG ID33954
Wikipedia LinkNot Available
METLIN ID6057
PubChem Compound448209
PDB IDNCC
ChEBI ID16556
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. 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: Human antibody reactivity against xenogeneic N-glycolylneuraminic acid and galactose-alpha-1,3-galactose antigen. Xenotransplantation. 2016 Jul;23(4):279-92. doi: 10.1111/xen.12239. Epub 2016 Jul 4. [PubMed:27373998 ]

Only showing the first 10 proteins. There are 14 proteins in total.

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

Only showing the first 10 proteins. There are 14 proteins in total.