Uridine diphosphate glucose

Identification

Name
Uridine diphosphate glucose
Accession Number
DB01861  (EXPT01669, EXPT03198, DB04355)
Type
Small Molecule
Groups
Experimental
Description

A 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 acid. Also serves as a precursor of sucrose lipopolysaccharides, and glycosphingolipids.

Structure
Thumb
Synonyms
  • 5'-Diphosphoglucose
  • Co-galactoisomerase
  • Co-waldenase
  • Cogalactoisomerase
  • UDP-Glucose
  • UDPG
  • Uridine 5'-pyrophosphate glucose ester
  • Uridine-5'-Diphosphoglucose
Categories
Not Available
UNII
V50K1D7P4Y
CAS number
133-89-1
Weight
Average: 566.3018
Monoisotopic: 566.055020376
Chemical Formula
C15H24N2O17P2
InChI Key
HSCJRCZFDFQWRP-JZMIEXBBSA-N
InChI
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
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
SMILES

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UGalactose-1-phosphate uridylyltransferaseNot AvailableEscherichia coli (strain K12)
UUDP-glucose 4-epimeraseNot AvailableHuman
UAlpha,alpha-trehalose-phosphate synthase [UDP-forming]Not AvailableEscherichia coli (strain K12)
UGlucose-1-phosphate thymidylyltransferaseNot AvailableSalmonella typhimurium (strain LT2 / SGSC1412 / ATCC 700720)
UUDP-glucose 4-epimeraseNot AvailableEscherichia coli (strain K12)
UDNA beta-glucosyltransferaseNot AvailableEnterobacteria phage T4
UGlycosyltransferase 6 domain-containing protein 1Not AvailableHuman
UWbpPNot AvailablePseudomonas aeruginosa
UGlycogenin-1Not AvailableHuman
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
Not Available
Pathways
PathwayCategory
Fabry diseaseDisease
Glycogenosis, Type VI. Hers diseaseDisease
GLUT-1 deficiency syndromeDisease
Metachromatic Leukodystrophy (MLD)Disease
Glycogenosis, Type III. Cori disease, Debrancher glycogenosisDisease
Mucopolysaccharidosis VI. Sly syndromeDisease
GalactosemiaDisease
Gaucher DiseaseDisease
Galactosemia II (GALK)Disease
Sucrase-isomaltase deficiencyDisease
Sphingolipid MetabolismMetabolic
Starch and Sucrose MetabolismMetabolic
Lactose SynthesisMetabolic
Glycogenosis, Type IV. Amylopectinosis, Anderson diseaseDisease
Congenital disorder of glycosylation CDG-IIdDisease
Nucleotide Sugars MetabolismMetabolic
Galactose MetabolismMetabolic
Globoid Cell LeukodystrophyDisease
Galactosemia IIIDisease
Krabbe diseaseDisease
Glycogen synthetase deficiencyDisease
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

General References
Not Available
External Links
Human Metabolome Database
HMDB60079
KEGG Compound
C00029
PubChem Compound
8629
PubChem Substance
46507150
ChemSpider
8308
BindingDB
50423218
ChEBI
46229
ChEMBL
CHEMBL375951
HET
UPG
Wikipedia
Uridine_diphosphate_glucose
PDB Entries
1a9y / 1a9z / 1ek6 / 1g93 / 1guq / 1i24 / 1i2b / 1i2c / 1i3k / 1iin
show 77 more

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility15.0 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count9ChemAxon
Refractivity106.46 m3·mol-1ChemAxon
Polarizability45.38 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This compound 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.
Kingdom
Organic compounds
Super Class
Nucleosides, nucleotides, and analogues
Class
Pyrimidine nucleotides
Sub Class
Pyrimidine nucleotide sugars
Direct Parent
Pyrimidine nucleotide sugars
Alternative Parents
Pyrimidine ribonucleoside diphosphates / Pentose phosphates / Glycosylamines / Monosaccharide phosphates / Organic pyrophosphates / Monoalkyl phosphates / Pyrimidones / Oxanes / Hydropyrimidines / Tetrahydrofurans
show 13 more
Substituents
Pyrimidine nucleotide sugar / Pyrimidine ribonucleoside diphosphate / Pentose phosphate / Pentose-5-phosphate / Glycosyl compound / N-glycosyl compound / Monosaccharide phosphate / Organic pyrophosphate / Pyrimidone / Monoalkyl phosphate
show 27 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
UDP-D-glucose (CHEBI:46229)

Targets

Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
Unknown
General Function
Zinc ion binding
Specific Function
Not Available
Gene Name
galT
Uniprot ID
P09148
Uniprot Name
Galactose-1-phosphate uridylyltransferase
Molecular Weight
39645.395 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Udp-n-acetylglucosamine 4-epimerase activity
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...
Gene Name
GALE
Uniprot ID
Q14376
Uniprot Name
UDP-glucose 4-epimerase
Molecular Weight
38281.435 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
  3. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235]
Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
Unknown
General Function
Alpha,alpha-trehalose-phosphate synthase (udp-forming) activity
Specific Function
Catalyzes the transfer of glucose from UDP-glucose to glucose-6-phosphate to form alpha,alpha-1,1 trehalose-6-phosphate. Acts with retention of the anomeric configuration of the UDP-sugar donor. Es...
Gene Name
otsA
Uniprot ID
P31677
Uniprot Name
Alpha,alpha-trehalose-phosphate synthase [UDP-forming]
Molecular Weight
53610.655 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
Kind
Protein
Organism
Salmonella typhimurium (strain LT2 / SGSC1412 / ATCC 700720)
Pharmacological action
Unknown
General Function
Magnesium ion binding
Specific Function
Catalyzes the formation of dTDP-glucose, from dTTP and glucose 1-phosphate, as well as its pyrophosphorolysis. Is also able to convert non natural substrates such as a wide array of alpha-D-hexopyr...
Gene Name
rmlA
Uniprot ID
P26393
Uniprot Name
Glucose-1-phosphate thymidylyltransferase
Molecular Weight
32453.085 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
Unknown
General Function
Udp-glucose 4-epimerase activity
Specific Function
Involved in the metabolism of galactose. Catalyzes the conversion of UDP-galactose (UDP-Gal) to UDP-glucose (UDP-Glc) through a mechanism involving the transient reduction of NAD. It is only active...
Gene Name
galE
Uniprot ID
P09147
Uniprot Name
UDP-glucose 4-epimerase
Molecular Weight
37264.875 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
Kind
Protein
Organism
Enterobacteria phage T4
Pharmacological action
Unknown
General Function
Dna beta-glucosyltransferase activity
Specific Function
Catalyzes the transfer of glucose (Glc) from uridine diphosphoglucose (UDP-Glc) to 5-hydroxymethylcytosine (5-HMC) in double-stranded DNA. Is involved in a DNA modification process to protect the p...
Gene Name
bgt
Uniprot ID
P04547
Uniprot Name
DNA beta-glucosyltransferase
Molecular Weight
40665.6 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Transferase activity, transferring hexosyl groups
Specific Function
Not Available
Gene Name
GLT6D1
Uniprot ID
Q7Z4J2
Uniprot Name
Glycosyltransferase 6 domain-containing protein 1
Molecular Weight
36273.575 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
  3. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235]
Kind
Protein
Organism
Pseudomonas aeruginosa
Pharmacological action
Unknown
General Function
Racemase and epimerase activity, acting on carbohydrates and derivatives
Specific Function
Not Available
Gene Name
Not Available
Uniprot ID
Q8KN66
Uniprot Name
WbpP
Molecular Weight
37748.31 Da
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Metal ion binding
Specific Function
Self-glucosylates, via an inter-subunit mechanism, to form an oligosaccharide primer that serves as substrate for glycogen synthase.
Gene Name
GYG1
Uniprot ID
P46976
Uniprot Name
Glycogenin-1
Molecular Weight
39383.425 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235]

Drug created on June 13, 2005 07:24 / Updated on November 09, 2017 03:05