uridine diphosphate glucose

Also known as UDP-Glc, (UDP)glucose, (UPD)-glucose, [({[(2S,3R,4S,5S)-5-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]({[(3S,4R,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})phosphinic acid, UDPG, Co-waldenase, Co-galactoisomerase, uridine diphospho-D-glucose

chemical compound

Chemical data

Formula: C15H24N2O17P2
Molecular weight: 566.3 g/mol
IUPAC name: [[(2R,3S,4R,5R)-5-(2,4-dioxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl] [(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] hydrogen phosphate
SMILES: C1=CN(C(=O)NC1=O)[C@H]2[C@@H]([C@@H]([C@H](O2)COP(=O)(O)OP(=O)(O)O[C@@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O)O)O
InChIKey: HSCJRCZFDFQWRP-JZMIEXBBSA-N
XLogP: -6.3
Polar surface area: 292 Å²
H-bond donors: 9
H-bond acceptors: 17
Formal charge: 0

via PubChem

Drug data · ChEMBL

Molecule type: Small molecule

via ChEMBL · EBI

Research

3,033 papers

Studies on uridine-diphosphate-glucose.The Biochemical journal · 1952
Uridine diphosphate glucose confers oxidative stress tolerance in microalgae.BMC plant biology · 2025
Measurements of uridine diphosphate glucose and uridine diphosphate galactose--an appraisal.European journal of pediatrics · 1995
UDP-glucose accelerates SNAI1 mRNA decay and impairs lung cancer metastasis.Nature · 2019
Glucokinase Variant Proteins Are Resistant to Fasting-Induced Uridine Diphosphate Glucose-Dependent Degradation in Maturity-Onset Diabetes of the Young Type 2 Patients.International journal of molecular sciences · 2023

via PubMed

Wikidata facts

Mass: 566.055

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found in taxon: Streptomyces hygroscopicus
chemical formula: C₁₅H₂₄N₂O₁₇P₂
canonical SMILES: C1=CN(C(=O)NC1=O)C2C(C(C(O2)COP(=O)(O)OP(=O)(O)OC3C(C(C(C(O3)CO)O)O)O)O)O
isomeric SMILES: C1=CN(C(=O)NC1=O)[C@H]2[C@@H]([C@@H]([C@H](O2)COP(=O)(O)OP(=O)(O)O[C@@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O)O)O
Commons category: Uridine diphosphate glucose
subject has role: primary metabolite

Sources (4)

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