Record Information
Version1.0
Creation date2010-04-08 22:06:47 UTC
Update date2018-05-28 23:14:39 UTC
Primary IDFDB005660
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameUdp-glucose
DescriptionA key intermediate in carbohydrate metabolism. Serves as a precursor of glycogen, can be metabolized into UDPgalactose and UDPglucuronic acid which can then be incorporated into polysaccharides as galactose and glucuronic acidand is also serves as a precursor of sucrose lipopolysaccharides, and glycosphingolipids.; It is a precursor of glycogen and can be converted into UDP-galactose and UDP-glucuronic acid, which can then be used as substrates by the enzymes that make polysaccharides containing galactose and glucuronic acid.; Uridine diphosphate glucose (uracil-diphosphate glucose, UDP-glucose) is a nucleotide sugar. It is involved in glycosyltransferase reactions in metabolism. Udp-glucose is found in many foods, some of which are skunk currant, black salsify, winter squash, and red algae.
CAS Number133-89-1
Structure
Thumb
Synonyms
SynonymSource
GLUCOSE-uridine-C1,5'-diphosphATEChEBI
UDP-D-GlucoseChEBI
UDPglucoseChEBI
Uridine diphosphate glucoseChEBI
URIDINE-5'-diphosphATE-glucoseChEBI
UDP-alpha-D-GlucoseKegg
GLUCOSE-uridine-C1,5'-diphosphoric acidGenerator
Uridine diphosphoric acid glucoseGenerator
URIDINE-5'-diphosphoric acid-glucoseGenerator
UDP-a-D-GlucoseGenerator
UDP-Α-D-glucoseGenerator
Diphosphate glucose, uridineMeSH
Diphosphoglucose, uridineMeSH
Glucose, UDPMeSH
Glucose, uridine diphosphateMeSH
UDP GlucoseMeSH
UDPGMeSH
Uridine diphosphoglucoseMeSH
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
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
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
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
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
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-054k-3933570000-89f658b2d26ff158d84cView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0fk9-4942706000-3a83736296429f83adeeView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)splash10-014i-0000090000-1692ab5f5dad1cf7e436View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-015a-0439510000-69e7cd4c2c365a24706bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-0109-5753970000-03f34041208ba93ef87aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0901110000-4b81825405869909992eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-3911000000-6fd09254750e77963110View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03di-5900000000-03a2a98eb0aa84737530View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-4901260000-8396a090c14de7f2d708View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01ox-8907020000-94410556a0288cb8167bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-06tf-5901000000-10132c85ad33464d4eefView in MoNA
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
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
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).