Record Information
Version1.0
Creation date2020-04-20 17:25:18 UTC
Update date2020-04-21 18:02:13 UTC
Primary IDFDB112170
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameCytidine 5'-monophosphate-N-acetylneuraminic acid
DescriptionCytidine 5'-monophosphate-N-acetylneuraminic acid, also known as CMP-N-acetyl-b-neuraminic acid or CMP-beta-neu5ac, 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 5'-monophosphate-N-acetylneuraminic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). Cytidine 5'-monophosphate-N-acetylneuraminic acid exists in all living organisms, ranging from bacteria to humans.
CAS NumberNot Available
Structure
Thumb
Synonyms
SynonymSource
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
Predicted Properties
PropertyValueSource
Water Solubility36.3 g/LALOGPS
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
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+/m0/s1
InChI KeyTXCIAUNLDRJGJZ-BILDWYJOSA-N
Isomeric 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
Average Molecular Weight614.4511
Monoisotopic Molecular Weight614.147267476
Classification
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
OntologyNo ontology term
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
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-MS
TypeDescriptionSplash KeyView
Predicted GC-MSCytidine 5'-monophosphate-N-acetylneuraminic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-01ot-9512160000-178f009287639a11dbfdSpectrum
Predicted GC-MSCytidine 5'-monophosphate-N-acetylneuraminic acid, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-044l-9624017000-8c596d9b4644a97fbb65Spectrum
Predicted GC-MSCytidine 5'-monophosphate-N-acetylneuraminic acid, TMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCytidine 5'-monophosphate-N-acetylneuraminic acid, TMS_1_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCytidine 5'-monophosphate-N-acetylneuraminic acid, TMS_1_4, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCytidine 5'-monophosphate-N-acetylneuraminic acid, TMS_1_5, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCytidine 5'-monophosphate-N-acetylneuraminic acid, TMS_1_6, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCytidine 5'-monophosphate-N-acetylneuraminic acid, TMS_1_7, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCytidine 5'-monophosphate-N-acetylneuraminic acid, TMS_1_8, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCytidine 5'-monophosphate-N-acetylneuraminic acid, TMS_1_9, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCytidine 5'-monophosphate-N-acetylneuraminic acid, TMS_1_10, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCytidine 5'-monophosphate-N-acetylneuraminic acid, TMS_2_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCytidine 5'-monophosphate-N-acetylneuraminic acid, TMS_2_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCytidine 5'-monophosphate-N-acetylneuraminic acid, TMS_2_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCytidine 5'-monophosphate-N-acetylneuraminic acid, TMS_2_4, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCytidine 5'-monophosphate-N-acetylneuraminic acid, TMS_2_5, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCytidine 5'-monophosphate-N-acetylneuraminic acid, TMS_2_6, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCytidine 5'-monophosphate-N-acetylneuraminic acid, TMS_2_7, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCytidine 5'-monophosphate-N-acetylneuraminic acid, TMS_2_8, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCytidine 5'-monophosphate-N-acetylneuraminic acid, TMS_2_9, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCytidine 5'-monophosphate-N-acetylneuraminic acid, TMS_2_10, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCytidine 5'-monophosphate-N-acetylneuraminic acid, TMS_2_11, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCytidine 5'-monophosphate-N-acetylneuraminic acid, TMS_2_12, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCytidine 5'-monophosphate-N-acetylneuraminic acid, TMS_2_13, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCytidine 5'-monophosphate-N-acetylneuraminic acid, TMS_2_14, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0912020000-9d330aadc1882c503212Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-3902000000-b2c85490ddb7f53db6f4Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03di-6910000000-a8d1f94c4661e1dd3097Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-4813091000-d68fb03c5bbe9978f2e5Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-4912010000-168821fb3a4dc5a309b1Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-08fr-9310000000-5e2455827ac9cc8b0a87Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-2004169000-eac426191a551fa0ea5fSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0bvs-9003180000-afd899893a04da29e2e4Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004l-9001310000-a0291ac7ad84d4ba3ecbSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0240369000-cae65d161602c1ecc345Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-1864591000-a0ca8cc5e78443e5226cSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03k9-3943120000-4ac27539b86275883867Spectrum
NMRNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound IDNot Available
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
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
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference