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Human Metabolome Database Version 3.5

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Showing metabocard for CMP-N-glycoloylneuraminate (HMDB12206)

Record Information
Version 3.5
Creation Date 2009-04-06 10:21:00 -0600
Update Date 2013-05-14 11:39:58 -0600
HMDB ID HMDB12206
Secondary Accession Numbers None
Metabolite Identification
Common Name CMP-N-glycoloylneuraminate
Description CMP-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
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
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 Formula C20H31N4O17P
Average Molecular Weight 630.4505
Monoisotopic Molecular Weight 630.142182098
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 Number 98300-80-2
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 Key AOOQVSNKZOZOHI-LBTQWYOJSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Carbohydrates and Carbohydrate Conjugates
Class Sugar Acids and Derivatives
Sub Class Sugar 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 Parent Pyranoid Amino Acids and Derivatives
Ontology
Status Expected and Not Quantified
Origin
  • Endogenous
Biofunction Not Available
Application Not Available
Cellular locations Not Available
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point Not Available Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
Water Solubility 29.9 g/L ALOGPS
LogP -2.89 ALOGPS
LogP -6.4 ChemAxon
LogS -1.32 ALOGPS
pKa (strongest acidic) 1.84 ChemAxon
pKa (strongest basic) -0.77 ChemAxon
Hydrogen Acceptor Count 17 ChemAxon
Hydrogen Donor Count 11 ChemAxon
Polar Surface Area 340.92 A2 ChemAxon
Rotatable Bond Count 12 ChemAxon
Refractivity 127.12 ChemAxon
Polarizability 54.2 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge -2 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations Not Available
Biofluid Locations Not Available
Tissue Location Not Available
Pathways Not Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB028851
KNApSAcK ID Not Available
Chemspider ID Not Available
KEGG Compound ID C03691 Link_out
BioCyc ID CPD-262 Link_out
BiGG ID Not Available
Wikipedia Link Not Available
NuGOwiki Link HMDB12206 Link_out
Metagene Link HMDB12206 Link_out
METLIN ID Not Available
PubChem Compound 53481387 Link_out
PDB ID Not Available
ChEBI ID 18098 Link_out
References
Synthesis Reference Not Available
Material Safety Data Sheet (MSDS) Not Available
General References Not Available
Enzymes
Name: N-acylneuraminate cytidylyltransferase
Reactions:
  • CTP + N-acylneuraminate = diphosphate + CMP-N-acylneuraminate [RN:R02599]
Gene Name: CMAS
Uniprot ID: Q8NFW8 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA