Uridine diphosphate glucose

Identification

Generic Name
Uridine diphosphate glucose
DrugBank Accession Number
DB01861
Background

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.

Type
Small Molecule
Groups
Experimental
Structure
Weight
Average: 566.3018
Monoisotopic: 566.055020376
Chemical Formula
C15H24N2O17P2
Synonyms
  • 5'-Diphosphoglucose
  • Co-galactoisomerase
  • Co-waldenase
  • Cogalactoisomerase
  • UDP-Glucose
  • UDPG
  • Uridine 5'-pyrophosphate glucose ester
  • Uridine-5'-Diphosphoglucose

Pharmacology

Indication

Not Available

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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UGalactose-1-phosphate uridylyltransferaseNot AvailableEscherichia coli (strain K12)
UUDP-glucose 4-epimeraseNot AvailableHumans
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 AvailableHumans
UWbpPNot AvailablePseudomonas aeruginosa
UGlycogenin-1Not AvailableHumans
UUracil nucleotide/cysteinyl leukotriene receptor
regulator
Humans
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

Adverse Effects
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Toxicity

Not Available

Pathways
PathwayCategory
Galactose MetabolismMetabolic
Starch and Sucrose MetabolismMetabolic
Globoid Cell LeukodystrophyDisease
Lactose SynthesisMetabolic
Glycogen Synthetase DeficiencyDisease
Glycogenosis, Type III. Cori Disease, Debrancher GlycogenosisDisease
GalactosemiaDisease
Metachromatic Leukodystrophy (MLD)Disease
Galactosemia II (GALK)Disease
Mucopolysaccharidosis VI. Sly SyndromeDisease
Sucrase-Isomaltase DeficiencyDisease
GLUT-1 Deficiency SyndromeDisease
Nucleotide Sugars MetabolismMetabolic
Sphingolipid MetabolismMetabolic
Gaucher DiseaseDisease
Galactosemia IIIDisease
Fabry DiseaseDisease
Krabbe DiseaseDisease
Glycogenosis, Type IV. Amylopectinosis, Anderson DiseaseDisease
Glycogenosis, Type VI. Hers DiseaseDisease
Congenital Disorder of Glycosylation CDG-IIdDisease
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Not Available
Food Interactions
Not Available

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
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
Alcohol / Alkyl phosphate / Aromatic heteromonocyclic compound / Azacycle / Glycosyl compound / Heteroaromatic compound / Hydrocarbon derivative / Hydropyrimidine / Lactam / Monoalkyl phosphate
show 27 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
UDP-D-glucose (CHEBI:46229)
Affected organisms
Not Available

Chemical Identifiers

UNII
V50K1D7P4Y
CAS number
133-89-1
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({[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})phosphoryl]oxy})phosphinic acid
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

References

General References
Not Available
Human Metabolome Database
HMDB0060079
KEGG Compound
C00029
PubChem Compound
8629
PubChem Substance
46507150
ChemSpider
8308
BindingDB
50209659
ChEBI
46229
ChEMBL
CHEMBL375951
ZINC
ZINC000008215472
PDBe Ligand
UPG
Wikipedia
Uridine_diphosphate_glucose
PDB Entries
1a9y / 1a9z / 1ek6 / 1g93 / 1guq / 1i24 / 1i2b / 1i2c / 1i3k / 1iin
show 122 more

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

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
Polarizability45.39 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-MSsplash10-054k-3933570000-89f658b2d26ff158d84c
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-014s-0100390000-c64b950587c78c33a630
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-014i-0000090000-07850dd3506000405b47
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-03dr-1521960000-f1e37bf552bae3967a9f
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-014i-1100940000-3610a036cce20f283a05
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-03di-1931300000-43eaf246f23df277e8c5
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-08gi-1936340000-37eea2b5ade989ba6815
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-236.7559395
predicted
DarkChem Lite v0.1.0
[M-H]-236.9348395
predicted
DarkChem Lite v0.1.0
[M-H]-236.8079395
predicted
DarkChem Lite v0.1.0
[M-H]-188.17723
predicted
DeepCCS 1.0 (2019)
[M+H]+236.4982395
predicted
DarkChem Lite v0.1.0
[M+H]+238.8628395
predicted
DarkChem Lite v0.1.0
[M+H]+242.2574395
predicted
DarkChem Lite v0.1.0
[M+H]+190.48611
predicted
DeepCCS 1.0 (2019)
[M+Na]+234.9438395
predicted
DarkChem Lite v0.1.0
[M+Na]+237.2888395
predicted
DarkChem Lite v0.1.0
[M+Na]+235.7662395
predicted
DarkChem Lite v0.1.0
[M+Na]+196.22655
predicted
DeepCCS 1.0 (2019)

Targets

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insights and accelerate drug research.
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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. [Article]
  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. [Article]
Kind
Protein
Organism
Humans
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. [Article]
  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. [Article]
  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. [Article]
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. [Article]
  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. [Article]
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. [Article]
  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. [Article]
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. [Article]
  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. [Article]
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. [Article]
  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. [Article]
Kind
Protein
Organism
Humans
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. [Article]
  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. [Article]
  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. [Article]
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
Humans
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. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Regulator
General Function
Dual specificity receptor for uracil nucleotides and cysteinyl leukotrienes (CysLTs). Signals through G(i) and inhibition of adenylyl cyclase. May mediate brain damage by nucleotides and CysLTs following ischemia.
Specific Function
Chemokine receptor activity
Gene Name
GPR17
Uniprot ID
Q13304
Uniprot Name
Uracil nucleotide/cysteinyl leukotriene receptor
Molecular Weight
40988.99 Da
References
  1. Marucci G, Dal Ben D, Lambertucci C, Santinelli C, Spinaci A, Thomas A, Volpini R, Buccioni M: The G Protein-Coupled Receptor GPR17: Overview and Update. ChemMedChem. 2016 Dec 6;11(23):2567-2574. doi: 10.1002/cmdc.201600453. Epub 2016 Nov 14. [Article]

Drug created at June 13, 2005 13:24 / Updated at June 12, 2020 16:52