Record Information
Version1.0
Creation Date2016-09-30 23:04:04 UTC
Update Date2020-04-22 15:12:07 UTC
BMDB IDBMDB0003369
Secondary Accession Numbers
  • BMDB03369
Metabolite Identification
Common NameCDP-glucose
DescriptionCDP-glucose, also known as CDP-D-glucose or CDP-GLC, 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. Based on a literature review a significant number of articles have been published on CDP-glucose.
Structure
Thumb
Synonyms
ValueSource
CDP-D-GlucoseChEBI
CDP-GLCChEBI
Cytidine diphosphate-glucoseMeSH, HMDB
CDP-a-D-GlucoseGenerator, HMDB
CDP-Α-D-glucoseGenerator, HMDB
CDP-GlucoseMeSH
Chemical FormulaC15H25N3O16P2
Average Molecular Weight565.317
Monoisotopic Molecular Weight565.071004791
IUPAC Name{[(2R,3S,4R,5R)-5-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}({[hydroxy({[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})phosphoryl]oxy})phosphinic acid
Traditional Namecytidine diphosphate glucose
CAS Registry Number2906-23-2
SMILES
NC1=NC(=O)N(C=C1)[C@@H]1O[C@H](COP(O)(=O)OP(O)(=O)O[C@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)[C@@H](O)[C@H]1O
InChI Identifier
InChI=1S/C15H25N3O16P2/c16-7-1-2-18(15(25)17-7)13-11(23)9(21)6(31-13)4-30-35(26,27)34-36(28,29)33-14-12(24)10(22)8(20)5(3-19)32-14/h1-2,5-6,8-14,19-24H,3-4H2,(H,26,27)(H,28,29)(H2,16,17,25)/t5-,6-,8-,9-,10+,11-,12-,13-,14-/m1/s1
InChI KeyCGPHZDRCVSLMCF-JZMIEXBBSA-N
Chemical Taxonomy
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 diphosphate
  • Pentose phosphate
  • Pentose-5-phosphate
  • Glycosyl compound
  • N-glycosyl compound
  • Monosaccharide phosphate
  • Organic pyrophosphate
  • Aminopyrimidine
  • Pyrimidone
  • Monoalkyl phosphate
  • Hydropyrimidine
  • Monosaccharide
  • Organic phosphoric acid derivative
  • Oxane
  • Phosphoric acid ester
  • Pyrimidine
  • Imidolactam
  • Alkyl phosphate
  • Tetrahydrofuran
  • Heteroaromatic compound
  • Secondary alcohol
  • Polyol
  • Oxacycle
  • Organoheterocyclic compound
  • Azacycle
  • Organic oxide
  • Organonitrogen compound
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Amine
  • Primary amine
  • Organooxygen compound
  • Organopnictogen compound
  • Alcohol
  • Organic oxygen compound
  • Primary alcohol
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-1.4ALOGPS
logP-5.7ChemAxon
logS-1.3ALOGPS
pKa (Strongest Acidic)1.73ChemAxon
pKa (Strongest Basic)-0.58ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count15ChemAxon
Hydrogen Donor Count9ChemAxon
Polar Surface Area300.82 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity108.44 m³·mol⁻¹ChemAxon
Polarizability45.94 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
HMDB IDHMDB0003369
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB023155
KNApSAcK IDC00019342
Chemspider ID388381
KEGG Compound IDC00501
BioCyc IDCDP-D-GLUCOSE
BiGG IDNot Available
Wikipedia LinkCytidine diphosphate glucose
METLIN ID6907
PubChem Compound439244
PDB IDNot Available
ChEBI ID28942
References
Synthesis ReferenceGinsburg, Victor; O'Brien, Paul J.; Hall, Clara W. Enzymic synthesis of cytidine 5'-diphosphate glucose. Biocherns Biophys. Res. Communs. (1962), 7 1-4.
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available