Record Information
Version1.0
Creation date2010-04-08 22:06:47 UTC
Update date2020-09-17 15:38:32 UTC
Primary IDFDB005660
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameUdp-glucose
DescriptionUridine diphosphate glucose, also known as udpglucose or UDP-alpha-D-glucose, 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. Uridine diphosphate glucose is an extremely weak basic (essentially neutral) compound (based on its pKa). Uridine diphosphate glucose exists in all living species, ranging from bacteria to humans. Within humans, uridine diphosphate glucose participates in a number of enzymatic reactions. In particular, galactose 1-phosphate and uridine diphosphate glucose can be biosynthesized from uridine diphosphategalactose and glucose 1-phosphate; which is catalyzed by the enzyme galactose-1-phosphate uridylyltransferase. In addition, uridine diphosphate glucose can be biosynthesized from uridine diphosphategalactose through its interaction with the enzyme UDP-glucose 4-epimerase. In humans, uridine diphosphate glucose is involved in galactose metabolism. Outside of the human body, Uridine diphosphate glucose has been detected, but not quantified in, several different foods, such as tea, ostrich ferns, chickpea, cinnamons, and sourdoughs. This could make uridine diphosphate glucose a potential biomarker for the consumption of these foods.
CAS Number133-89-1
Structure
Thumb
Synonyms
SynonymSource
GLUCOSE-uridine-C1,5'-diphosphATEChEBI
UDP-D-GlucoseChEBI
UDPglucoseChEBI
URIDINE-5'-diphosphATE-glucoseChEBI
UDP-alpha-D-GlucoseKegg
GLUCOSE-uridine-C1,5'-diphosphoric acidGenerator
URIDINE-5'-diphosphoric acid-glucoseGenerator
UDP-a-D-GlucoseGenerator
UDP-Α-D-glucoseGenerator
Uridine diphosphoric acid glucoseGenerator
Diphosphate glucose, uridineHMDB
Diphosphoglucose, uridineHMDB
Glucose, UDPHMDB
Glucose, uridine diphosphateHMDB
UDP GlucoseHMDB
UDPGHMDB
Uridine diphosphoglucoseHMDB
UDP-GLCHMDB
UDP-GlucoseHMDB
Uridine 5'-(alpha-D-glucopyranosyl pyrophosphate)HMDB
Uridine 5'-(α-D-glucopyranosyl pyrophosphate)HMDB
Uridine 5'-diphosphate glucoseHMDB
Uridine 5'-diphospho-alpha-D-glucoseHMDB
Uridine 5'-diphospho-α-D-glucoseHMDB
Uridine 5'-diphosphoglucoseHMDB
Uridine 5’-(α-D-glucopyranosyl pyrophosphate)HMDB
Uridine 5’-diphosphate glucoseHMDB
Uridine 5’-diphospho-α-D-glucoseHMDB
Uridine 5’-diphosphoglucoseHMDB
Uridine diphospho-D-glucoseHMDB
Uridine pyrophosphate-glucoseHMDB
Uridine diphosphate glucoseChEBI
Udp glucosebiospider
Udp-d-glucosebiospider
Udp-delta-glucosebiospider
Udp-GLCbiospider
UPGbiospider
Uridine 5'-diphospho-a-D-glucosebiospider
Uridine 5'-diphospho-alpha-delta-glucosebiospider
Uridine 5'-pyrophosphate a-D-glucopyranosyl esterbiospider
Uridine 5'-pyrophosphate a-delta-glucopyranosyl esterbiospider
Uridine diphospho-d-glucosebiospider
Uridine diphospho-delta-glucosebiospider
Predicted Properties
PropertyValueSource
Water Solubility15 g/LALOGPS
logP-1.4ALOGPS
logP-5ChemAxon
logS-1.6ALOGPS
pKa (Strongest Acidic)1.73ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count14ChemAxon
Hydrogen Donor Count9ChemAxon
Polar Surface Area291.54 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity106.46 m³·mol⁻¹ChemAxon
Polarizability45.39 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC15H24N2O17P2
IUPAC name[({[(2R,3S,4R,5R)-5-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]({[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})phosphinic acid
InChI IdentifierInChI=1S/C15H24N2O17P2/c18-3-5-8(20)10(22)12(24)14(32-5)33-36(28,29)34-35(26,27)30-4-6-9(21)11(23)13(31-6)17-2-1-7(19)16-15(17)25/h1-2,5-6,8-14,18,20-24H,3-4H2,(H,26,27)(H,28,29)(H,16,19,25)/t5-,6-,8-,9-,10+,11-,12-,13-,14-/m1/s1
InChI KeyHSCJRCZFDFQWRP-JZMIEXBBSA-N
Isomeric SMILESOC[C@H]1O[C@H](OP(O)(=O)OP(O)(=O)OC[C@H]2O[C@H]([C@H](O)[C@@H]2O)N2C=CC(=O)NC2=O)[C@H](O)[C@@H](O)[C@@H]1O
Average Molecular Weight566.3018
Monoisotopic Molecular Weight566.055020376
Classification
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
  • Pyrimidone
  • Monoalkyl phosphate
  • Hydropyrimidine
  • Monosaccharide
  • Organic phosphoric acid derivative
  • Oxane
  • Phosphoric acid ester
  • Pyrimidine
  • Alkyl phosphate
  • Heteroaromatic compound
  • Vinylogous amide
  • Tetrahydrofuran
  • Urea
  • Secondary alcohol
  • Lactam
  • Polyol
  • Oxacycle
  • Organoheterocyclic compound
  • Azacycle
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Primary alcohol
  • Alcohol
  • Organonitrogen compound
  • Organooxygen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSUdp-glucose, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-054k-3933570000-89f658b2d26ff158d84cSpectrum
Predicted GC-MSUdp-glucose, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0fk9-4942706000-3a83736296429f83adeeSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)splash10-014i-0000090000-1692ab5f5dad1cf7e436Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-015a-0439510000-69e7cd4c2c365a24706bSpectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-0109-5753970000-03f34041208ba93ef87aSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0901110000-4b81825405869909992eSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-3911000000-6fd09254750e77963110Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03di-5900000000-03a2a98eb0aa84737530Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-4901260000-8396a090c14de7f2d708Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01ox-8907020000-94410556a0288cb8167bSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-06tf-5901000000-10132c85ad33464d4eefSpectrum
NMR
TypeDescriptionView
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
2D NMR[1H,13C] 2D NMR SpectrumSpectrum
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID8629
Pubchem Substance IDNot Available
ChEBI ID18066
Phenol-Explorer IDNot Available
DrugBank IDDB01861
HMDB IDHMDB00286
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDUDP-GLUCOSE
BIGG IDNot Available
KNApSAcK IDC00001514
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDUridine diphosphate glucose
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).