Record Information
Version1.0
Creation date2011-09-21 00:14:30 UTC
Update date2018-05-28 18:32:51 UTC
Primary IDFDB022466
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameCytidine monophosphate N-acetylneuraminic acid
DescriptionCytidine monophosphate N-acetylneuraminic acid belongs to the class of organic compounds known as pyrimidine ribonucleoside monophosphates. These are pyrimidine ribobucleotides with monophosphate group linked to the ribose moiety. Cytidine monophosphate N-acetylneuraminic acid is an extremely weak basic (essentially neutral) compound (based on its pKa).
CAS Number22-12-8
Structure
Thumb
Synonyms
SynonymSource
Cytidine monophosphate N-acetylneuraminateGenerator
Cytidine monophosphoric acid N-acetylneuraminic acidGenerator
CMP-b-Neu5acGenerator
CMP-beta-Neu5acChEBI
CMP-N-acetylneuraminatehmdb
CMP-N-Acetylneuraminic acidGenerator
CMP-N-acylneuraminatehmdb
CMP-NeuNAchmdb
CMP-SialateGenerator
CMP-Sialic acidChEBI
CMP-β-neu5acGenerator
Cytidine 5'-monoate N-acetylneuraminic acidHMDB
Cytidine 5'-monophosphate N-acetylneuraminic acidhmdb
Cytidine monoate N-acetylneuraminateGenerator
Cytidine monoate N-acetylneuraminic acidChEBI
Cytidine monoic acid N-acetylneuraminic acidGenerator
Cytidine Monophosphate N-Acetylneuraminatehmdb
Cytidine Monophosphate N-Acetylneuraminic acidhmdb
CYTIDINE-5'-monoate-5-N-acetylneuraminateGenerator
CYTIDINE-5'-monoATE-5-N-acetylneuraminIC ACIDChEBI
CYTIDINE-5'-monoic acid-5-N-acetylneuraminic acidGenerator
Predicted Properties
PropertyValueSource
Water Solubility9.55 g/LALOGPS
logP-2.2ALOGPS
logP-5.7ChemAxon
logS-1.8ALOGPS
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
Polarizability54.22 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC20H31N4O16P
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
InChI IdentifierInChI=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-/m1/s1
InChI KeyTXCIAUNLDRJGJZ-GDTVTMGESA-N
Isomeric SMILES[H][C@@](O)(CO)[C@@]([H])(O)[C@]1([H])O[C@](C[C@]([H])(O)[C@@]1([H])NC(C)=O)(OP(O)(=O)OC[C@@]1([H])O[C@@]([H])(N2C=CC(N)=NC2=O)[C@]([H])(O)[C@]1([H])O)C(O)=O
Average Molecular Weight614.4511
Monoisotopic Molecular Weight614.147267476
Classification
Description Belongs to the class of organic compounds known as pyrimidine ribonucleoside monophosphates. These are pyrimidine ribobucleotides with monophosphate group linked to the ribose moiety.
KingdomOrganic compounds
Super ClassNucleosides, nucleotides, and analogues
ClassPyrimidine nucleotides
Sub ClassPyrimidine ribonucleotides
Direct ParentPyrimidine ribonucleoside monophosphates
Alternative Parents
Substituents
  • Pyrimidine ribonucleoside monophosphate
  • Neuraminic acid
  • Pentose-5-phosphate
  • Pentose phosphate
  • C-glucuronide
  • N-glycosyl compound
  • Glycosyl compound
  • C-glycosyl compound
  • Monosaccharide phosphate
  • Hydroxypyrimidine
  • Dialkyl phosphate
  • Alkyl phosphate
  • Pyrimidine
  • Pyran
  • Phosphoric acid ester
  • Oxane
  • Organic phosphoric acid derivative
  • Monosaccharide
  • Hydropyrimidine
  • Heteroaromatic compound
  • Tetrahydrofuran
  • Secondary alcohol
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Polyol
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Carboximidic acid derivative
  • Carboximidic acid
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Alcohol
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
OntologyNo ontology term
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MSNot Available
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0912020000-eee5949b3e008ab58d75Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-2901000000-456a975dbaf46125fac5Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03di-6920000000-c2fae1421ff7753accb9Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-08mi-1901020000-a9efe0a98112c9d1ab04Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03xr-4902000000-e2c39b0c70426e514e5eSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0cfr-9310000000-dbea8fd6d58d7e2c136aSpectrum
NMRNot Available
ChemSpider ID395082
ChEMBL IDNot Available
KEGG Compound IDC00128
Pubchem Compound ID448209
Pubchem Substance IDNot Available
ChEBI ID16556
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB01176
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG ID33954
KNApSAcK IDNot Available
HET IDNCC
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
Enzymes
NameGene NameUniProt ID
N-acylneuraminate cytidylyltransferaseCMASQ8NFW8
CMP-N-acetylneuraminate-beta-1,4-galactoside alpha-2,3-sialyltransferaseST3GAL3Q11203
Alpha-N-acetylneuraminide alpha-2,8-sialyltransferaseST8SIA1Q92185
Lactosylceramide alpha-2,3-sialyltransferaseST3GAL5Q9UNP4
Type 2 lactosamine alpha-2,3-sialyltransferaseST3GAL6Q9Y274
CMP-N-acetylneuraminate-beta-galactosamide-alpha-2,3-sialyltransferase 1ST3GAL1Q11201
CMP-N-acetylneuraminate-beta-galactosamide-alpha-2,3-sialyltransferase 4ST3GAL4Q11206
Alpha-N-acetyl-neuraminyl-2,3-beta-galactosyl-1,3-N-acetyl-galactosaminide alpha-2,6-sialyltransferaseST6GALNAC4Q9H4F1
Pathways
NameSMPDB LinkKEGG Link
Amino Sugar MetabolismSMP00045 map00520
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference