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Record Information
Version1.0
Creation Date2016-09-30 22:42:03 UTC
Update Date2020-05-19 22:00:58 UTC
BMDB IDBMDB0001176
Secondary Accession Numbers
  • BMDB01176
Metabolite Identification
Common NameCytidine monophosphate N-acetylneuraminic acid
DescriptionCytidine monophosphate N-acetylneuraminic acid, also known as CMP acetylneuraminic acid or CMP-nana, 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. Cytidine monophosphate N-acetylneuraminic acid is possibly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). Cytidine monophosphate N-acetylneuraminic acid exists in all living organisms, ranging from bacteria to humans. In cattle, cytidine monophosphate N-acetylneuraminic acid is involved in the metabolic pathway called the amino sugar metabolism pathway.
Structure
Thumb
Synonyms
ValueSource
CMP Acetylneuraminic acidChEBI
CMP-beta-Neu5acChEBI
CMP-N-AcetylneuraminateChEBI
CMP-NanaChEBI
CMP-Neu5acChEBI
CMP-NeuNAcChEBI
CMP-Sialic acidChEBI
Cytidine monophosphate N-acetylneuraminic acidChEBI
CYTIDINE-5'-monophosphATE-5-N-acetylneuraminIC ACIDChEBI
Cytidine-5'-monophospho-N-acetylneuraminic acidChEBI
Cytidine-5'-monophosphono-N-acetylneuraminic acidChEBI
CMP-N-Acetyl-beta-neuraminateKegg
CMP AcetylneuraminateGenerator
CMP-b-Neu5acGenerator
CMP-Β-neu5acGenerator
CMP-N-Acetylneuraminic acidGenerator
CMP-SialateGenerator
Cytidine monophosphate N-acetylneuraminateGenerator
Cytidine monophosphoric acid N-acetylneuraminic acidGenerator
CYTIDINE-5'-monophosphate-5-N-acetylneuraminateGenerator
CYTIDINE-5'-monophosphoric acid-5-N-acetylneuraminic acidGenerator
Cytidine-5'-monophospho-N-acetylneuraminateGenerator
Cytidine-5'-monophosphono-N-acetylneuraminateGenerator
CMP-N-Acetyl-b-neuraminateGenerator
CMP-N-Acetyl-b-neuraminic acidGenerator
CMP-N-Acetyl-beta-neuraminic acidGenerator
CMP-N-Acetyl-β-neuraminateGenerator
CMP-N-Acetyl-β-neuraminic acidGenerator
Cytidine 5'-monophosphate-N-acetylneuraminateGenerator
Cytidine 5'-monophosphoric acid-N-acetylneuraminic acidGenerator
CMP-N-AcylneuraminateHMDB
Cytidine 5'-monophosphate N-acetylneuraminic acidHMDB
Acetylneuraminic acid, CMPHMDB
Acid, CMP acetylneuraminicHMDB
Acid, CMP-sialicHMDB
CMP Sialic acidHMDB
Cytidine monophosphate N acetylneuraminic acidHMDB
CMP-NeuAcHMDB
Cytidine 5'-monophosphic acid-N-acetylneuraminic acidHMDB
Cytidine 5'-monophospho-N-acetylneuraminateHMDB
Cytidine 5'-monophospho-N-acetylneuraminic acidHMDB
Cytidine 5’-monophosphate-N-acetylneuraminateHMDB
Cytidine 5’-monophosphate-N-acetylneuraminic acidHMDB
Cytidine 5’-monophosphic acid-N-acetylneuraminic acidHMDB
Cytidine 5’-monophospho-N-acetylneuraminateHMDB
Cytidine 5’-monophospho-N-acetylneuraminic acidHMDB
Cytidine monophosphic acid N-acetylneuraminic acidHMDB
Cytidine 5'-monophosphate-N-acetylneuraminic acidHMDB
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
Description 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
StatusExpected but not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm
  • Golgi
  • Nucleus
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-2.7ALOGPS
logP-5.7ChemAxon
logS-1.2ALOGPS
pKa (Strongest Acidic)1.48ChemAxon
pKa (Strongest Basic)-0.22ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count16ChemAxon
Hydrogen Donor Count10ChemAxon
Polar Surface Area320.69 ŲChemAxon
Rotatable Bond Count11ChemAxon
Refractivity125.42 m³·mol⁻¹ChemAxon
Polarizability53.81 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
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
  • Golgi
  • Nucleus
Biospecimen Locations
  • Placenta
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
PlacentaExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
Abnormal Concentrations
Not Available
HMDB IDHMDB0001176
DrugBank IDDB02485
Phenol Explorer Compound IDNot Available
FooDB IDFDB022466
KNApSAcK IDNot Available
Chemspider ID395082
KEGG Compound IDC00128
BioCyc IDNot Available
BiGG ID33954
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound448209
PDB IDNot Available
ChEBI ID16556
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Involved in N-acylneuraminate cytidylyltransferase acti
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) (By similarity).
Gene Name:
CMAS
Uniprot ID:
Q3SZM5
Molecular weight:
48438.0
Reactions
N-Acetylneuraminic acid + Cytidine triphosphate → Cytidine monophosphate N-acetylneuraminic acid + Pyrophosphatedetails
General function:
Involved in beta-galactoside alpha-2,6-sialyltransferas
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:
A5D7T4
Molecular weight:
55418.0
General function:
Involved in alpha-N-acetylneuraminate alpha-2,8-sialylt
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:
Q6ZXD2
Molecular weight:
40452.0
General function:
Involved in lactosylceramide alpha-2,3-sialyltransferas
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:
Q70D51
Molecular weight:
48263.0