Showing metabocard for Uridine diphosphate glucose (BMDB0000286)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (8) Show 8 proteinsXML
Record Information
Version1.0
Creation Date2016-09-30 22:27:50 UTC
Update Date2020-06-04 20:19:13 UTC
BMDB IDBMDB0000286
Secondary Accession Numbers
  • BMDB00286
Metabolite Identification
Common NameUridine diphosphate 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.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
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
Chemical FormulaC15H24N2O17P2
Average Molecular Weight566.3018
Monoisotopic Molecular Weight566.055020376
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
Traditional Nameudp-α-D-glucose
CAS Registry Number133-89-1
SMILES
OC[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
InChI Identifier
InChI=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
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
  • 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
StatusDetected and Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Endoplasmic reticulum
  • Golgi
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-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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Biological Properties
Cellular Locations
  • Endoplasmic reticulum
  • Golgi
Biospecimen Locations
  • Liver
  • Skeletal Muscle
  • Testis
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
LiverExpected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
  • Not Applicable
 details
Skeletal MuscleExpected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
  • Not Applicable
 details
TestisDetected and Quantified126 +/- 32 nmol/g of tissueNot SpecifiedNot Specified
Normal
    • Aidin Foroutan, C...
 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0000286
DrugBank IDDB01861
Phenol Explorer Compound IDNot Available
FooDB IDFDB005660
KNApSAcK IDC00001514
Chemspider IDNot Available
KEGG Compound IDC00029
BioCyc IDCPD-12575
BiGG IDNot Available
Wikipedia LinkUridine_diphosphate_glucose
METLIN IDNot Available
PubChem Compound8629
PDB IDNot Available
ChEBI ID46229
References
Synthesis ReferenceBurma, D. P.; Mortimer, D. C. Biosynthesis of uridine diphosphate glucose and sucrose in sugar-beet leaf. Archives of Biochemistry and Biophysics (1956), 62 16-28.
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

Enzyme Details
1. Phosphoglucomutase-1
General function:
Carbohydrate transport and metabolism
Specific function:
This enzyme participates in both the breakdown and synthesis of glucose.
Gene Name:
PGM1
Uniprot ID:
Q08DP0
Molecular weight:
61589.0
Reactions
Uridine diphosphate glucose → Glucose 1-phosphatedetails
Enzyme Details
2. UDP-glucose 6-dehydrogenase
General function:
Cell wall/membrane/envelope biogenesis
Specific function:
Catalyzes the formation of UDP-alpha-D-glucuronate, a constituent of complex glycosaminoglycans (By similarity). Required for the biosynthesis of chondroitin sulfate and heparan sulfate. Required for embryonic development via its role in the biosynthesis of glycosaminoglycans (By similarity).
Gene Name:
UGDH
Uniprot ID:
P12378
Molecular weight:
55136.0
Reactions
Uridine diphosphate glucose + 2 NAD + Water → Uridine diphosphate glucuronic acid +2 NADHdetails
Enzyme Details
3. Galactose-1-phosphate uridylyltransferase
General function:
Energy production and conversion
Specific function:
Not Available
Gene Name:
GALT
Uniprot ID:
Q0V7N7
Molecular weight:
37812.0
Enzyme Details
4. Glycogen [starch] synthase, muscle
General function:
Cell wall/membrane/envelope biogenesis
Specific function:
Transfers the glycosyl residue from UDP-Glc to the non-reducing end of alpha-1,4-glucan.
Gene Name:
GYS1
Uniprot ID:
A7MB78
Molecular weight:
83814.0
Reactions
Uridine diphosphate glucose → Amylose + Uridine 5'-diphosphatedetails
Enzyme Details
5. Galactose-1-phosphate uridylyltransferase
General function:
Energy production and conversion
Specific function:
Not Available
Gene Name:
GALT
Uniprot ID:
Q58CX1
Molecular weight:
41288.0
Reactions
Uridine diphosphategalactose + Glucose 1-phosphate → Uridine diphosphate glucose + Galactose 1-phosphatedetails
Uridine diphosphate glucose + Galactose 1-phosphate → Uridine diphosphategalactose + Glucose 1-phosphatedetails
Uridine diphosphategalactose + Glucose 1-phosphate → Galactose 1-phosphate + Uridine diphosphate glucosedetails
Enzyme Details
6. UTP--glucose-1-phosphate uridylyltransferase
General function:
Involved in UTP:glucose-1-phosphate uridylyltransferase
Specific function:
Plays a central role as a glucosyl donor in cellular metabolic pathways.
Gene Name:
UGP2
Uniprot ID:
Q07130
Molecular weight:
56903.0
Reactions
Glucose 1-phosphate + Uridine triphosphate → Uridine diphosphate glucose + Pyrophosphatedetails
Uridine diphosphate glucose + Pyrophosphate → Glucose 1-phosphate + Uridine triphosphatedetails
Enzyme Details
7. P2Y purinoceptor 14
General function:
Involved in purinergic nucleotide receptor activity, G-
Specific function:
Receptor for UDP-glucose and other UDP-sugar coupled to G-proteins. Not activated by ATP, ADP, UTP or ATP (By similarity).
Gene Name:
P2RY14
Uniprot ID:
Q3SX17
Molecular weight:
38697.0
Enzyme Details
8. UDP-glucose 4-epimerase
General function:
Not Available
Specific function:
Catalyzes two distinct but analogous reactions: the reversible epimerization of UDP-glucose to UDP-galactose and the reversible epimerization of UDP-N-acetylglucosamine to UDP-N-acetylgalactosamine. The reaction with UDP-Gal plays a critical role in the Leloir pathway of galactose catabolism in which galactose is converted to the glycolytic intermediate glucose 6-phosphate. It contributes to the catabolism of dietary galactose and enables the endogenous biosynthesis of both UDP-Gal and UDP-GalNAc when exogenous sources are limited. Both UDP-sugar interconversions are important in the synthesis of glycoproteins and glycolipids.
Gene Name:
GALE
Uniprot ID:
Q3T105
Molecular weight:
38254.0
Reactions
Uridine diphosphate glucose + Galactose 1-phosphate → Uridine diphosphategalactose + Glucose 1-phosphatedetails
Uridine diphosphategalactose → Uridine diphosphate glucosedetails