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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2009-04-06 16:21:00 UTC
Update Date2017-12-07 02:36:10 UTC
HMDB IDHMDB0012206
Secondary Accession Numbers
  • HMDB12206
Metabolite Identification
Common NameCMP-N-glycoloylneuraminate
DescriptionCMP-N-glycoloylneuraminate is an intermediate in Aminosugars metabolism. It is generated from CMP-N-acetylneuraminate via the enzyme CMP-N-acetylneuraminate monooxygenase (EC 1.14.18.2). CMP-N-glycoloylneuraminate can be converted to N-Glycolylneuraminate via the enzyme N-acylneuraminate cytidylyltransferase (EC 2.7.7.43).
Structure
Thumb
Synonyms
ValueSource
(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}phosphinato)oxy]-4-hydroxy-5-(2-hydroxyacetamido)-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylateHMDB
CMP-N-GlycolylneuraminateHMDB
CMP-N-Glycolylneuraminic acidHMDB
CMP-Neu5GCHMDB
CMP-NeungcHMDB
Cytidine monophosphate-N-glycoloylneuraminic acidHMDB
Chemical FormulaC20H31N4O17P
Average Molecular Weight630.4505
Monoisotopic Molecular Weight630.142182098
IUPAC Name(2S,4S,6R)-6-[(1S,2S)-3-[({[(2R,3S,4R,5R)-5-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]-1,2-dihydroxypropyl]-2,4-dihydroxy-5-(2-hydroxyacetamido)oxane-2-carboxylic acid
Traditional Name(2S,4S,6R)-6-[(1S,2S)-3-({[(2R,3S,4R,5R)-5-(4-amino-2-oxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy)-1,2-dihydroxypropyl]-2,4-dihydroxy-5-(2-hydroxyacetamido)oxane-2-carboxylic acid
CAS Registry Number98300-80-2
SMILES
NC1=NC(=O)N(C=C1)[C@@H]1O[C@H](COP(O)(=O)OC[C@H](O)[C@H](O)[C@@H]2O[C@@](O)(C[C@H](O)C2NC(=O)CO)C(O)=O)[C@@H](O)[C@H]1O
InChI Identifier
InChI=1S/C20H31N4O17P/c21-10-1-2-24(19(34)22-10)17-15(31)14(30)9(40-17)6-39-42(36,37)38-5-8(27)13(29)16-12(23-11(28)4-25)7(26)3-20(35,41-16)18(32)33/h1-2,7-9,12-17,25-27,29-31,35H,3-6H2,(H,23,28)(H,32,33)(H,36,37)(H2,21,22,34)/t7-,8-,9+,12?,13-,14+,15+,16+,17+,20-/m0/s1
InChI KeyAOOQVSNKZOZOHI-LBTQWYOJSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as pyrimidine ribonucleoside monophosphates. These are pyrimidine ribobucleotides with monophosphate group linked to the ribose moiety.
KingdomChemical entities
Super ClassOrganic compounds
ClassNucleosides, nucleotides, and analogues
Sub ClassPyrimidine nucleotides
Direct ParentPyrimidine ribonucleoside monophosphates
Alternative Parents
Substituents
  • Pyrimidine ribonucleoside monophosphate
  • N-acylneuraminic acid
  • N-acylneuraminic acid or derivatives
  • Neuraminic acid
  • Pentose phosphate
  • Pentose-5-phosphate
  • C-glucuronide
  • N-glycosyl compound
  • Glycosyl compound
  • C-glycosyl compound
  • Monosaccharide phosphate
  • Aminopyrimidine
  • Pyrimidone
  • Dialkyl phosphate
  • Monosaccharide
  • Organic phosphoric acid derivative
  • Hydroxy acid
  • Hydropyrimidine
  • Oxane
  • Alpha-hydroxy acid
  • Phosphoric acid ester
  • Primary aromatic amine
  • Alkyl phosphate
  • Imidolactam
  • Pyrimidine
  • Pyran
  • Tetrahydrofuran
  • Heteroaromatic compound
  • Hemiacetal
  • Carboxamide group
  • Amino acid
  • Amino acid or derivatives
  • Secondary alcohol
  • Secondary carboxylic acid amide
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Primary amine
  • Amine
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Carbonyl group
  • Organopnictogen compound
  • Organic oxide
  • Primary alcohol
  • Alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Source:

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 Solubility29.9 g/LALOGPS
logP-2.9ALOGPS
logP-6.4ChemAxon
logS-1.3ALOGPS
pKa (Strongest Acidic)1.84ChemAxon
pKa (Strongest Basic)-0.77ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count17ChemAxon
Hydrogen Donor Count11ChemAxon
Polar Surface Area340.92 ŲChemAxon
Rotatable Bond Count12ChemAxon
Refractivity127.12 m³·mol⁻¹ChemAxon
Polarizability54.2 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, Positivesplash10-03y0-2339634000-dfbf60ceffde2a26e445View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0910002000-d4f1e52062015dc10b7fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-2910000000-2d4cb8ba80ae2d146166View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03di-3930000000-8a1620c372f90002ef9bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03dj-0943723000-7d8efafe708e2fdb9425View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-9212000000-ad5d3dc896e26dbec3daView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01t9-9301000000-aa2110890252b1fb8388View in MoNA
Biological Properties
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationNot Available
PathwaysNot Available
NameSMPDB/PathwhizKEGG
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 IDFDB028851
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC03691
BioCyc IDCPD-262
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound53481387
PDB IDNot Available
ChEBI ID18098
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

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-Glycolylneuraminic acid → Pyrophosphate + CMP-N-glycoloylneuraminatedetails