URIDINE 5'-DIPHOSPHATE

Investigational

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C9H14N2O12P2
Molecular Weight	404.1612
Optical Activity	UNSPECIFIED
Defined Stereocenters	4 / 4
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

O[C@H]1[C@@H](O)[C@@H](O[C@@H]1COP(O)(=O)OP(O)(O)=O)N2C=CC(=O)NC2=O

InChI

InChIKey=XCCTYIAWTASOJW-XVFCMESISA-N

InChI=1S/C9H14N2O12P2/c12-5-1-2-11(9(15)10-5)8-7(14)6(13)4(22-8)3-21-25(19,20)23-24(16,17)18/h1-2,4,6-8,13-14H,3H2,(H,19,20)(H,10,12,15)(H2,16,17,18)/t4-,6-,7-,8-/m1/s1

HIDE SMILES / InChI

Molecular Formula	C9H14N2O12P2
Molecular Weight	404.1612
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	4 / 4
E/Z Centers	0
Optical Activity	UNSPECIFIED

Approval Year

Targets

Primary Target	Pharmacology	Potency
Purinergic receptor P2Y14 5 Target ID: CHEMBL4518 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18252808	Antagonist 2849
Pyrimidinergic receptor P2Y6 7 Target ID: CHEMBL4714 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9755289	Agonist 2752
Pyrimidinergic receptor P2Y6 7 Target ID: CHEMBL4714 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16942026 \| https://www.ncbi.nlm.nih.gov/pubmed/8670200 \| https://www.ncbi.nlm.nih.gov/pubmed/20446735	Agonist 2752	13.0 nM [EC50]
Uracil nucleotide/cysteinyl leukotriene receptor 5 Target ID: CHEMBL1075162 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20148890 \| https://www.ncbi.nlm.nih.gov/pubmed/16990797	Agonist 2752	1.14 µM [EC50]
Purinergic receptor P2Y14 5 Target ID: CHEMBL4518 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19902968 \| https://www.ncbi.nlm.nih.gov/pubmed/20446735	Agonist 2752	160.0 nM [EC50]

PubMed

Title	Date	PubMed
Age-related changes in the response of human articular cartilage to IL-1alpha and transforming growth factor-beta (TGF-beta): chondrocytes exhibit a diminished sensitivity to TGF-beta.	2003-12-26	13679381
Glucosamine and glucose induce insulin resistance by different mechanisms in rat skeletal muscle.	2003-12	12954597
A novel polygalacturonic acid bioflocculant REA-11 produced by Corynebacterium glutamicum: a proposed biosynthetic pathway and experimental confirmation.	2003-12	12827320
Diabetes and the accompanying hyperglycemia impairs cardiomyocyte calcium cycling through increased nuclear O-GlcNAcylation.	2003-11-07	12941958
In vitro heparan sulfate polymerization: crucial roles of core protein moieties of primer substrates in addition to the EXT1-EXT2 interaction.	2003-10-24	12907685
Analysis of the two active sites of the hyaluronan synthase and the chondroitin synthase of Pasteurella multocida.	2003-10	12799342
Solid-supported enzymatic synthesis of pectic oligogalacturonides and their analysis by MALDI-TOF mass spectrometry.	2003-09-10	14499571
Extracellular nucleotides and nucleosides induce proliferation and increase nucleoside transport in human glioma cell lines.	2003-09	14558596
UDP-N-acetylglucosaminyl transferase (OGT) in brain tissue: temperature sensitivity and subcellular distribution of cytosolic and nuclear enzyme.	2003-09	12911634
The role of tryptophan 314 in the conformational changes of beta1,4-galactosyltransferase-I.	2003-08-29	12927542
Chondroitin sulfate synthase-2. Molecular cloning and characterization of a novel human glycosyltransferase homologous to chondroitin sulfate glucuronyltransferase, which has dual enzymatic activities.	2003-08-08	12761225
Coexpression of functional P2X and P2Y nucleotide receptors in single cerebellar granule cells.	2003-08-01	12868072
Crystal structures of the T4 phage beta-glucosyltransferase and the D100A mutant in complex with UDP-glucose: glucose binding and identification of the catalytic base for a direct displacement mechanism.	2003-07-25	12860129
Chemical synthesis of uridine diphospho-D-xylose and UDP-L-arabinose.	2003-07-11	12839484
Origin of lipid A species modified with 4-amino-4-deoxy-L-arabinose in polymyxin-resistant mutants of Escherichia coli. An aminotransferase (ArnB) that generates UDP-4-deoxyl-L-arabinose.	2003-07-04	12704196
A high-throughput solid-phase extraction assay capable of measuring diverse polyprenyl phosphate: sugar-1-phosphate transferases as exemplified by the WecA, MraY, and MurG proteins.	2003-06-15	12758253
The folate precursor p-aminobenzoate is reversibly converted to its glucose ester in the plant cytosol.	2003-06-06	12668665
P2Y6 nucleotide receptor activates PKC to protect 1321N1 astrocytoma cells against tumor necrosis factor-induced apoptosis.	2003-06	12825835
Purinergic receptors on microglial cells: functional expression in acute brain slices and modulation of microglial activation in vitro.	2003-06	12814360
Potent P2Y6 receptor mediated contractions in human cerebral arteries.	2003-05-09	12737633
Attenuation of signal flow from P2Y6 receptor by protein kinase C-alpha in SK-N-BE(2)C human neuroblastoma cells.	2003-05	12716436
Pharmacological characterization of P2Y receptor subtypes on isolated tiger salamander Müller cells.	2003-04-15	12655599
Measurement of UDP-N-acetylglucosaminyl transferase (OGT) in brain cytosol and characterization of anti-OGT antibodies.	2003-03-15	12654302
Tumor necrosis factor alpha-induced apoptosis in astrocytes is prevented by the activation of P2Y6, but not P2Y4 nucleotide receptors.	2003-03-15	12623123
Beta 1,4-galactosyltransferase (beta 4GalT)-IV is specific for GlcNAc 6-O-sulfate. Beta 4GalT-IV acts on keratan sulfate-related glycans and a precursor glycan of 6-sulfosialyl-Lewis X.	2003-03-14	12511560
[Pharmacogenomic approaches for prevention of drug toxicity in cancer chemotherapy].	2003-03	12669388
ATP-induced calcium oscillations and change of P2Y subtypes with culture conditions in HeLa cells.	2003-03	12579523
Three highly conserved proteins catalyze the conversion of UDP-N-acetyl-D-glucosamine to precursors for the biosynthesis of O antigen in Pseudomonas aeruginosa O11 and capsule in Staphylococcus aureus type 5. Implications for the UDP-N-acetyl-L-fucosamine biosynthetic pathway.	2003-02-07	12464616
Pyridoxalphosphate-6-azophenyl-2',4'-disulfonic acid can antagonize the purinoceptor-mediated inhibition of M-current in bullfrog sympathetic neurons.	2003-02-06	12527396
Long-term potentiation of glutamatergic synaptic transmission induced by activation of presynaptic P2Y receptors in the rat medial habenula nucleus.	2003-02	12603274
Altered calcium regulation in freshly isolated aortic smooth muscle cells from bile duct-ligated rats: role of nitric oxide.	2003-02	12531189
Probing the mechanism of a fungal glycosyltransferase essential for cell wall biosynthesis. UDP-chitobiose is not a substrate for chitin synthase.	2003-01-07	12929388
The stable pyrimidines UDPbetaS and UTPgammaS discriminate between contractile cerebrovascular P2 receptors.	2003-01-05	12504787
Mast cells: beyond IgE.	2003-01	12532090
Normally functioning murF is essential for the optimal expression of methicillin resistance in Staphylococcus aureus.	2003	12959401
A sensitive and rapid bioassay of homogalacturonan synthase using 2-aminobenzamide-labeled oligogalacturonides.	2002-11	12461139
Muscle uridine diphosphate-hexosamines do not decrease despite correction of hyperglycemia-induced insulin resistance in type 2 diabetes.	2002-11	12414889
Metabolizing enzyme localization and activities in the first trimester human placenta: the effect of maternal and gestational age, smoking and alcohol consumption.	2002-10	12351530
Analgesic effects of intrathecal administration of P2Y nucleotide receptor agonists UTP and UDP in normal and neuropathic pain model rats.	2002-10	12235234
The Drosophila gene brainiac encodes a glycosyltransferase putatively involved in glycosphingolipid synthesis.	2002-09-06	12130651
Arabinoxylan biosynthesis in wheat. Characterization of arabinosyltransferase activity in Golgi membranes.	2002-09	12226522
Identification of two cysteine residues involved in the binding of UDP-GalNAc to UDP-GalNAc:polypeptide N-acetylgalactosaminyltransferase 1 (GalNAc-T1).	2002-09	12199709
The structural basis for specificity in human ABO(H) blood group biosynthesis.	2002-09	12198488
Accumulation of the lipid A precursor UDP-2,3-diacylglucosamine in an Escherichia coli mutant lacking the lpxH gene.	2002-07-19	12000771
Significance of altered bilirubin subfractions in bile following hepatectomy.	2002-07	12127809
Evaluation of critical structural elements of UDP-sugar substrates and certain cysteine residues of a vertebrate hyaluronan synthase.	2002-06-14	11943783
Fast, efficient capillary electrophoresis method for measuring nucleotide degradation and metabolism.	2002-04-05	12064539
Effect of a conserved mutation in uridine diphosphate glucuronosyltransferase 1A1 and 1A6 on glucuronidation of a metabolite of flutamide.	2002-04	11956667
Galactose-1-phosphate uridylyltransferase: kinetics of formation and reaction of uridylyl-enzyme intermediate in wild-type and specifically mutated uridylyltransferases.	2002	12418221
Intact Golgi synthesize complex branched O-linked chains on glycoside primers: evidence for the functional continuity of seven glycosyltransferases and three sugar nucleotide transporters.	2001-08	12376727

Substance Class	Chemical Created by `admin` on `Mon Mar 31 22:26:35 GMT 2025` Edited by `admin` on `Mon Mar 31 22:26:35 GMT 2025`
Record UNII	5G0F599A1Y
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

URIDINE 5'-DIPHOSPHATE

Systematic Name

English

5'-UDP

Preferred Name

English

URIDINE 5'-(TRIHYDROGEN DIPHOSPHATE)

Systematic Name

English

URIDINE 5'-DIPHOSPHATE [MI]

Common Name

English

URIDINE 5'-PYROPHOSPHATE

Systematic Name

English

URIDINE 5'-PYROPHOSPHORIC ACID

Common Name

English

UDP

Common Name

English

URIDINE, 5'-(TRIHYDROGEN DIPHOSPHATE)

Common Name

English

URIDINE 5'-DIPHOSPHORIC ACID

Common Name

English

Code System Code Type Description

CHEBI

58223