UDP-4-Keto-pyranose (PAMDB001697)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 11:54:54 AM
Metabolite IDPAMDB001697
Identification
Name: UDP-4-Keto-pyranose
Description:UDP-4-keto-pyranose is a member of the chemical class known as Pyrimidine Ribonucleoside Diphosphates. These are pyrimidine ribobucleotides with diphosphate group linked to the ribose moiety.
Structure
Thumb
🔍MOLSDFPDBSMILESInChIView Structure
Synonyms:
  • UDP-4-keto-pyranose
  • UDP-4-Ketopentose
  • UDP-Ara4O
  • UDP-L-Ara4O
  • Uridine 5'-β-L-threo-pentapyranosyl-4''-ulose diphosphate
  • Uridine 5'-β-L-threo-pentapyranosyl-4''-ulose diphosphoric acid
  • Uridine 5'-b-L-threo-pentapyranosyl-4''-ulose diphosphate
  • Uridine 5'-b-L-threo-pentapyranosyl-4''-ulose diphosphoric acid
  • Uridine 5'-beta-L-threo-pentapyranosyl-4''-ulose diphosphate
  • Uridine 5'-beta-L-threo-pentapyranosyl-4''-ulose diphosphoric acid
  • Uridine 5'-β-L-threo-pentapyranosyl-4''-ulose diphosphate
  • Uridine 5'-β-L-threo-pentapyranosyl-4''-ulose diphosphoric acid
Chemical Formula: C14H18N2O16P2
Average Molecular Weight: 532.244
Monoisotopic Molecular Weight: 532.013155562
InChI Key: URJZIQLTPCJVMW-SVROINDSSA-L
InChI:InChI=1S/C14H20N2O16P2/c17-5-3-28-13(11(22)8(5)19)31-34(26,27)32-33(24,25)29-4-6-9(20)10(21)12(30-6)16-2-1-7(18)15-14(16)23/h1-2,6,8-13,19-22H,3-4H2,(H,24,25)(H,26,27)(H,15,18,23)/p-2/t6-,8+,9-,10-,11-,12?,13-/m1/s1
CAS number: Not Available
IUPAC Name:1-[(3R,4S,5R)-5-{[({[(2R,3R,4R)-3,4-dihydroxy-5-oxooxan-2-yl]oxy}(hydroxy)phosphoryl phosphonato)oxy]methyl}-3,4-dihydroxyoxolan-2-yl]-2-oxo-1,2-dihydropyrimidin-4-olate
Traditional IUPAC Name: 1-[(3R,4S,5R)-5-[({[(2R,3R,4R)-3,4-dihydroxy-5-oxooxan-2-yl]oxy(hydroxy)phosphoryl phosphonato}oxy)methyl]-3,4-dihydroxyoxolan-2-yl]-2-oxopyrimidin-4-olate
SMILES:[H][C@]1(COP([O-])(=O)OP(O)(=O)O[C@@]2([H])OCC(=O)[C@]([H])(O)[C@@]2([H])O)OC([H])(N2C=CC([O-])=NC2=O)[C@]([H])(O)[C@]1([H])O
Chemical Taxonomy
Taxonomy DescriptionThis compound belongs to the class of organic compounds known as pyrimidine ribonucleoside diphosphates. These are pyrimidine ribobucleotides with diphosphate group linked to the ribose moiety.
Kingdom Organic compounds
Super ClassNucleosides, nucleotides, and analogues
Class Pyrimidine nucleotides
Sub ClassPyrimidine ribonucleotides
Direct Parent Pyrimidine ribonucleoside diphosphates
Alternative Parents
Substituents
  • Pyrimidine ribonucleoside diphosphate
  • N-glycosyl compound
  • Glycosyl compound
  • Organic pyrophosphate
  • Monosaccharide phosphate
  • Monoalkyl phosphate
  • Pyrimidone
  • Alkyl phosphate
  • Pyrimidine
  • Phosphoric acid ester
  • Oxane
  • Organic phosphoric acid derivative
  • Organic phosphate
  • Monosaccharide
  • Hydropyrimidine
  • Saccharide
  • Heteroaromatic compound
  • Oxolane
  • Cyclic ketone
  • Secondary alcohol
  • Ketone
  • 1,2-diol
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Alcohol
  • Organic anion
  • Aromatic heteromonocyclic compound
Molecular Framework Aromatic heteromonocyclic compounds
External Descriptors Not Available
Physical Properties
State: Not Available
Charge:-2
Melting point: Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility50.8 mg/mLALOGPS
logP-1.3ALOGPS
logP-3.5ChemAxon
logS-1.1ALOGPS
pKa (Strongest Acidic)1.73ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count14ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area277.3 Å2ChemAxon
Rotatable Bond Count8ChemAxon
Refractivity109.4 m3·mol-1ChemAxon
Polarizability42.18 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Cytoplasm
Reactions:
L-Glutamate + UDP-4-Keto-pyranose <> alpha-Ketoglutarate + Uridine 5''-diphospho-{beta}-4-deoxy-4-amino-L-arabinose
NAD + Uridine diphosphate glucuronic acid > Carbon dioxide + NADH + UDP-4-Keto-pyranose
Uridine diphosphate glucuronic acid + NAD <> UDP-4-Keto-pyranose + Carbon dioxide + NADH + Hydrogen ion
Uridine 5''-diphospho-{beta}-4-deoxy-4-amino-L-arabinose + Oxoglutaric acid <> UDP-4-Keto-pyranose + L-Glutamate
Pathways:
  • Amino sugar and nucleotide sugar metabolism pae00520
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0200190000-d590a1d321f92c78316fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01t9-0111090000-c63a25ccd6ed116d50d3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0089-9801000000-a06ed8c72e1e5e635698View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001l-8200190000-c3435a8aa4d3d5a746bdView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-003s-8900080000-05ab55bc9c02e1ebbf87View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-059x-9100000000-9c2450446a73c43177afView in MoNA
References
References:
  • Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
  • van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195
Synthesis Reference: Not Available
Material Safety Data Sheet (MSDS) Not Available
External Links:
ResourceLink
CHEBI IDNot Available
HMDB IDNot Available
Pubchem Compound ID25244748
Kegg IDC16155
ChemSpider IDNot Available
Wikipedia IDNot Available
BioCyc ID5-BETA-L-THREO-PENTAPYRANOSYL-4-ULOSE-
EcoCyc ID5-BETA-L-THREO-PENTAPYRANOSYL-4-ULOSE-