Explore a selection of our essential drug information below, or:
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
Structure for Uridine diphosphate glucose (DB01861)
- 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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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 UPutative glycosyltransferase 6 domain-containing protein 1 Not Available Humans UWbpP Not Available Pseudomonas aeruginosa UGlycogenin-1 Not Available Humans UUracil nucleotide/cysteinyl leukotriene receptor regulatorHumans - 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
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.- 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
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
- 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 126 more
Clinical Trials
- Clinical Trials
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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
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 236.7559395 predictedDarkChem Lite v0.1.0 [M-H]- 236.9348395 predictedDarkChem Lite v0.1.0 [M-H]- 236.8079395 predictedDarkChem Lite v0.1.0 [M-H]- 188.17723 predictedDeepCCS 1.0 (2019) [M+H]+ 236.4982395 predictedDarkChem Lite v0.1.0 [M+H]+ 238.8628395 predictedDarkChem Lite v0.1.0 [M+H]+ 242.2574395 predictedDarkChem Lite v0.1.0 [M+H]+ 190.48611 predictedDeepCCS 1.0 (2019) [M+Na]+ 234.9438395 predictedDarkChem Lite v0.1.0 [M+Na]+ 237.2888395 predictedDarkChem Lite v0.1.0 [M+Na]+ 235.7662395 predictedDarkChem Lite v0.1.0 [M+Na]+ 196.22655 predictedDeepCCS 1.0 (2019)
Targets
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- Kind
- Protein
- Organism
- Escherichia coli (strain K12)
- Pharmacological action
- Unknown
- General Function
- Not Available
- Specific Function
- ferrous iron binding
- Gene Name
- galT
- Uniprot ID
- P09148
- Uniprot Name
- Galactose-1-phosphate uridylyltransferase
- Molecular Weight
- 39645.395 Da
References
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General 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
- Specific Function
- identical protein binding
- 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]
- Kind
- Protein
- Organism
- Escherichia coli (strain K12)
- Pharmacological action
- Unknown
- General Function
- Catalyzes the transfer of glucose from UDP-alpha-D-glucose (UDP-Glc) to D-glucose 6-phosphate (Glc-6-P) to form trehalose-6-phosphate. Acts with retention of the anomeric configuration of the UDP-sugar donor. Essential for viability of the cells at low temperatures and at elevated osmotic strength.
- Specific Function
- alpha,alpha-trehalose-phosphate synthase (UDP-forming) activity
- Gene Name
- otsA
- Uniprot ID
- P31677
- Uniprot Name
- Alpha,alpha-trehalose-phosphate synthase [UDP-forming]
- Molecular Weight
- 53610.655 Da
References
- Kind
- Protein
- Organism
- Salmonella typhimurium (strain LT2 / SGSC1412 / ATCC 700720)
- Pharmacological action
- Unknown
- General Function
- Catalyzes the formation of dTDP-glucose, from dTTP and glucose 1-phosphate, as well as its pyrophosphorolysis. Is the first of four enzymes commited to biosynthesis of dTDP-L-rhamnose in S.typhimurium LT2. Is also able to convert non natural substrates such as a wide array of alpha-D-hexopyranosyl, deoxy-alpha-D-glucopyranosyl, aminodeoxy-alpha-D-hexopyranosyl and acetamidodeoxy-alpha-D-hexopyranosyl phosphates to their corresponding dTDP- and UDP-nucleotide sugars.
- Specific Function
- glucose-1-phosphate thymidylyltransferase activity
- Gene Name
- rmlA
- Uniprot ID
- P26393
- Uniprot Name
- Glucose-1-phosphate thymidylyltransferase
- Molecular Weight
- 32453.085 Da
References
- Kind
- Protein
- Organism
- Escherichia coli (strain K12)
- Pharmacological action
- Unknown
- General 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 on UDP-galactose and UDP-glucose.
- Specific Function
- identical protein binding
- Gene Name
- galE
- Uniprot ID
- P09147
- Uniprot Name
- UDP-glucose 4-epimerase
- Molecular Weight
- 37264.875 Da
References
- Kind
- Protein
- Organism
- Enterobacteria phage T4
- Pharmacological action
- Unknown
- General Function
- Catalyzes the transfer of glucose from uridine diphosphoglucose to 5-hydroxymethyl cytosine of T4 DNA to yield glucosyl 5-hydroxymethyl cytosine (glc-HMC) (PubMed:22229759). This DNA process seems to occur immediately after DNA synthesis since the DNA alpha-glucosyltransferase interacts with the clamp protein gp45 (PubMed:22229759). The glc-HMC modification protects the phage genome against its own nucleases and the host restriction endonuclease system (PubMed:22229759). The glc-HMC modification also protects against the host CRISPR-Cas9 defense system (PubMed:26081634).
- Specific Function
- DNA beta-glucosyltransferase activity
- Gene Name
- bgt
- Uniprot ID
- P04547
- Uniprot Name
- DNA beta-glucosyltransferase
- Molecular Weight
- 40665.6 Da
References
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Not Available
- Specific Function
- glycosyltransferase activity
- Gene Name
- GLT6D1
- Uniprot ID
- Q7Z4J2
- Uniprot Name
- Putative glycosyltransferase 6 domain-containing protein 1
- Molecular Weight
- 32607.375 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]
- Kind
- Protein
- Organism
- Pseudomonas aeruginosa
- Pharmacological action
- Unknown
- General Function
- Not Available
- Specific Function
- dTDP-glucose 4,6-dehydratase activity
- Gene Name
- Not Available
- Uniprot ID
- Q8KN66
- Uniprot Name
- WbpP
- Molecular Weight
- 37748.31 Da
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Glycogenin participates in the glycogen biosynthetic process along with glycogen synthase and glycogen branching enzyme. It self-glucosylates, via an inter-subunit mechanism, to form an oligosaccharide primer that serves as substrate for glycogen synthase
- Specific Function
- glycogenin glucosyltransferase activity
- 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]
- 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