Uridine diphosphate glucose

Identification

Generic Name

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

Similar Structures

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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Contraindications & Blackbox Warnings

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Pharmacodynamics

Not Available

Mechanism of action

Target	Actions	Organism
UGalactose-1-phosphate uridylyltransferase	Not Available	Escherichia coli (strain K12)
UUDP-glucose 4-epimerase	Not Available	Humans
UAlpha,alpha-trehalose-phosphate synthase [UDP-forming]	Not Available	Escherichia coli (strain K12)
UGlucose-1-phosphate thymidylyltransferase	Not Available	Salmonella typhimurium (strain LT2 / SGSC1412 / ATCC 700720)
UUDP-glucose 4-epimerase	Not Available	Escherichia coli (strain K12)
UDNA beta-glucosyltransferase	Not Available	Enterobacteria phage T4
UGlycosyltransferase 6 domain-containing protein 1	Not Available	Humans
UWbpP	Not Available	Pseudomonas aeruginosa
UGlycogenin-1	Not Available	Humans
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

Pathway	Category
Galactose Metabolism	Metabolic
Starch and Sucrose Metabolism	Metabolic
Globoid Cell Leukodystrophy	Disease
Lactose Synthesis	Metabolic
Glycogen Synthetase Deficiency	Disease
Glycogenosis, Type III. Cori Disease, Debrancher Glycogenosis	Disease
Galactosemia	Disease
Metachromatic Leukodystrophy (MLD)	Disease
Galactosemia II (GALK)	Disease
Mucopolysaccharidosis VI. Sly Syndrome	Disease
Sucrase-Isomaltase Deficiency	Disease
GLUT-1 Deficiency Syndrome	Disease
Nucleotide Sugars Metabolism	Metabolic
Sphingolipid Metabolism	Metabolic
Gaucher Disease	Disease
Galactosemia III	Disease
Fabry Disease	Disease
Krabbe Disease	Disease
Glycogenosis, Type IV. Amylopectinosis, Anderson Disease	Disease
Glycogenosis, Type VI. Hers Disease	Disease
Congenital Disorder of Glycosylation CDG-IId	Disease

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

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

External Links

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 108 more

Clinical Trials

Clinical Trials

Phase	Status	Purpose	Conditions	Count

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

Property	Value	Source
Water Solubility	15.0 mg/mL	ALOGPS
logP	-1.4	ALOGPS
logP	-5	Chemaxon
logS	-1.6	ALOGPS
pKa (Strongest Acidic)	1.73	Chemaxon
pKa (Strongest Basic)	-3.6	Chemaxon
Physiological Charge	-2	Chemaxon
Hydrogen Acceptor Count	14	Chemaxon
Hydrogen Donor Count	9	Chemaxon
Polar Surface Area	291.54 Å²	Chemaxon
Rotatable Bond Count	9	Chemaxon
Refractivity	106.46 m³·mol^-1	Chemaxon
Polarizability	45.39 Å³	Chemaxon
Number of Rings	3	Chemaxon
Bioavailability	0	Chemaxon
Rule of Five	No	Chemaxon
Ghose Filter	No	Chemaxon
Veber's Rule	No	Chemaxon
MDDR-like Rule	Yes	Chemaxon

Predicted ADMET Features

Not Available

Spectra

Mass Spec (NIST)

Not Available

Spectra

Spectrum	Spectrum Type	Splash Key
Predicted GC-MS Spectrum - GC-MS	Predicted GC-MS	Not Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)	Predicted LC-MS/MS	Not Available

Targets

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Details1. Galactose-1-phosphate uridylyltransferase

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

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
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]

Details2. UDP-glucose 4-epimerase

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

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
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]
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]

Details3. Alpha,alpha-trehalose-phosphate synthase [UDP-forming]

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

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
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]

Details4. Glucose-1-phosphate thymidylyltransferase

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

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
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]

Details5. UDP-glucose 4-epimerase

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

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
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]

Details6. DNA beta-glucosyltransferase

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

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
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]

Details7. Glycosyltransferase 6 domain-containing protein 1

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

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
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]
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]

Details8. WbpP

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

Details9. Glycogenin-1

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

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]

Details10. Uracil nucleotide/cysteinyl leukotriene receptor

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

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

Uridine diphosphate glucose

Identification

Structure for Uridine diphosphate glucose (DB01861)

Pharmacology

Interactions

Categories

Chemical Identifiers

References

Clinical Trials

Pharmacoeconomics

Properties

Spectra

Targets

References

References

References

References

References

References

References

References

References