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Record Information
Version3.6
Creation Date2009-04-06 16:21:00 UTC
Update Date2013-05-14 17:39:58 UTC
HMDB IDHMDB12206
Secondary Accession NumbersNone
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
  1. (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-carboxylate
  2. CMP-N-Glycolylneuraminate
  3. CMP-N-Glycolylneuraminic acid
  4. CMP-Neu5Gc
  5. CMP-Neungc
  6. Cytidine monophosphate-N-glycoloylneuraminic acid
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 KeyInChIKey=AOOQVSNKZOZOHI-LBTQWYOJSA-N
Chemical Taxonomy
DescriptionThis compound 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
  • N-acylneuraminic acid or derivatives
  • N-acylneuraminic acid
  • Pyrimidine ribonucleoside monophosphate
  • Neuraminic acid
  • Pyranoid amino acid
  • C-glucuronide
  • Amino sugar
  • N-glycosyl compound
  • Glycosyl compound
  • C-glycosyl compound
  • Monosaccharide phosphate
  • Pyran carboxylic acid
  • Pyran carboxylic acid or derivatives
  • Dialkyl phosphate
  • Amino saccharide
  • Pyrimidone
  • Aminopyrimidine
  • Imidolactam
  • Alkyl phosphate
  • Pyrimidine
  • Pyran
  • Primary aromatic amine
  • Phosphoric acid ester
  • Oxane
  • Organic phosphoric acid derivative
  • Organic phosphate
  • Monosaccharide
  • Hydroxy acid
  • Hydropyrimidine
  • Alpha-hydroxy acid
  • Heteroaromatic compound
  • Oxolane
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Hemiacetal
  • Carboxamide group
  • 1,2-diol
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Carboxylic acid amide
  • Hydrocarbon derivative
  • Primary amine
  • Primary alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Amine
  • Alcohol
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
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 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count12ChemAxon
Refractivity127.12 m3·mol-1ChemAxon
Polarizability54.2 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationNot Available
PathwaysNot Available
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
NuGOwiki LinkHMDB12206
Metagene LinkHMDB12206
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