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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 IUPAC 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
KingdomOrganic Compounds
Super ClassCarbohydrates and Carbohydrate Conjugates
ClassSugar Acids and Derivatives
Sub ClassSugar Amino Acids and Derivatives
Other Descriptors
  • Aromatic Heteropolycyclic Compounds
  • Carbohydrates and Carbohydrate Conjugates
  • Pyrimidine Ribonucleoside Monophosphates
Substituents
  • 1,2 Diol
  • 1,3 Aminoalcohol
  • Alpha Hydroxy Acid
  • Aminopyrimidine
  • Carboxamide Group
  • Carboxylic Acid
  • Glyco Amino Acid
  • Glycosyl Compound
  • Hemiacetal
  • Hydropyrimidine
  • N Glycosyl Compound
  • Neuraminic Acid
  • Organic Hypophosphite
  • Organic Phosphite
  • Other Mixed Trisaccharide
  • Oxane
  • Oxolane
  • Phosphoric Acid Ester
  • Primary Alcohol
  • Pyrimidine
  • Pyrimidone
  • Secondary Alcohol
  • Secondary Carboxylic Acid Amide
  • Trisaccharide Phosphate
Direct ParentPyranoid Amino Acids and Derivatives
Ontology
StatusExpected and 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 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 area340.92ChemAxon
rotatable bond count12ChemAxon
refractivity127.12ChemAxon
polarizability54.2ChemAxon
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