uridine 5'-diphosphate

Also known as 5'-UDP, UDP, Uridine diphosphate, [[(2S,3S,4R,5R)-5-(2,4-dioxopyrimidin-1-yl)-3,4-dihydroxy-tetrahydrofuran-2-yl]methoxy-hydroxy-phosphoryl]oxyphosphonic acid, [[(2S,3S,4R,5R)-5-(2,4-dioxopyrimidin-1-yl)-3,4-dihydroxy-oxolan-2-yl]methoxy-hydroxy-phosphoryl]oxyphosphonic acid, Uridine pyrophosphate, [({[(2R,3S,4R,5R)-5-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]phosphonic acid, Uridine 5'-pyrophosphorate

chemical compound

Chemical data

Formula: C9H14N2O12P2
Molecular weight: 404.16 g/mol
IUPAC name: [[(2R,3S,4R,5R)-5-(2,4-dioxopyrimidin-1-yl)-3,4-dioxoniooxolan-2-yl]methoxy-oxidophosphoryl] 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-])[OH2+])[OH2+]
InChIKey: XCCTYIAWTASOJW-XVFCMESISA-N
XLogP: -4.9
Polar surface area: 180 Å²
H-bond donors: 4
H-bond acceptors: 10
Formal charge: 0

via PubChem

Research

711 papers

Protein expression of various hepatic uridine 5'-diphosphate glucuronosyltransferase (UGT) enzymes and their inter-correlations: a meta-analysis.Biopharmaceutics & drug disposition · 2014
Simultaneous one-pot multienzymatic synthesis and purification of Uridine-5'-Diphosphate-α-D-glucuronide and Uridine-5'-Diphosphate-α-d-xylose.Carbohydrate research · 2025
(E)-5-(2-bromovinyl)-2'-deoxyuridine (BVDU).Medicinal research reviews · 2005
Variability and function of family 1 uridine-5'-diphosphate glucuronosyltransferases (UGT1A).Critical reviews in clinical laboratory sciences · 2008
Uridine 5'-diphosphate glucose analogues. Inhibitors of protein glycosylation that show antiviral activity.Journal of medicinal chemistry · 1985

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Wikidata facts

Mass: 404.002

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Commons category: Uridine diphosphate
chemical formula: C₉H₁₄N₂O₁₂P₂
canonical SMILES: C1=CN(C(=O)NC1=O)C2C(C(C(O2)COP(=O)(O)OP(=O)(O)O)O)O
isomeric SMILES: O[C@@H]1[C@@H](COP(O)(=O)OP(O)(O)=O)O[C@H]([C@@H]1O)n1ccc(=O)[nH]c1=O
found in taxon: Caenorhabditis elegans
subject has role: primary metabolite

Sources (4)

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