UDP   Click here for help

GtoPdb Ligand ID: 1749

Abbreviated name: UDP
Synonyms: 5'-UDP | uridine 5'-diphosphate | uridine diphosphate
PDB Ligand
Compound class: Metabolite or derivative
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Ligand Activity Visualisation Charts

These are box plot that provide a unique visualisation, summarising all the activity data for a ligand taken from ChEMBL and GtoPdb across multiple targets and species. Click on a plot to see the median, interquartile range, low and high data points. A value of zero indicates that no data are available. A separate chart is created for each target, and where possible the algorithm tries to merge ChEMBL and GtoPdb targets by matching them on name and UniProt accession, for each available species. However, please note that inconsistency in naming of targets may lead to data for the same target being reported across multiple charts.

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View interactive charts of activity data across species
2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Click here for structure editor
Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the CDK toolkit. All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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Hydrogen bond acceptors 12
Hydrogen bond donors 6
Rotatable bonds 6
Topological polar surface area 237.46
Molecular weight 404
XLogP -4.31
No. Lipinski's rules broken 2
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

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Canonical SMILES OC1C(COP(=O)(OP(=O)(O)O)O)OC(C1O)n1ccc(=O)[nH]c1=O
Isomeric SMILES O[C@@H]1[C@@H](COP(=O)(OP(=O)(O)O)O)O[C@H]([C@@H]1O)n1ccc(=O)[nH]c1=O
InChI 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
InChI Key XCCTYIAWTASOJW-XVFCMESISA-N
References
1. Benned-Jensen T, Rosenkilde MM. (2010)
Distinct expression and ligand-binding profiles of two constitutively active GPR17 splice variants.
Br J Pharmacol, 159 (5): 1092-105. [PMID:20148890]
2. Bäck M, Powell WS, Dahlén SE, Drazen JM, Evans JF, Serhan CN, Shimizu T, Yokomizo T, Rovati GE. (2014)
Update on leukotriene, lipoxin and oxoeicosanoid receptors: IUPHAR Review 7.
Br J Pharmacol, 171 (15): 3551-74. [PMID:24588652]
3. Carter RL, Fricks IP, Barrett MO, Burianek LE, Zhou Y, Ko H, Das A, Jacobson KA, Lazarowski ER, Harden TK. (2009)
Quantification of Gi-mediated inhibition of adenylyl cyclase activity reveals that UDP is a potent agonist of the human P2Y14 receptor.
Mol Pharmacol, 76 (6): 1341-8. [PMID:19759354]
4. Ciana P, Fumagalli M, Trincavelli ML, Verderio C, Rosa P, Lecca D, Ferrario S, Parravicini C, Capra V, Gelosa P, Guerrini U, Belcredito S, Cimino M, Sironi L, Tremoli E, Rovati GE, Martini C, Abbracchio MP. (2006)
The orphan receptor GPR17 identified as a new dual uracil nucleotides/cysteinyl-leukotrienes receptor.
EMBO J, 25 (19): 4615-27. [PMID:16990797]
5. Communi D, Parmentier M, Boeynaems JM. (1996)
Cloning, functional expression and tissue distribution of the human P2Y6 receptor.
Biochem Biophys Res Commun, 222 (2): 303-8. [PMID:8670200]
6. Davenport AP, Alexander SP, Sharman JL, Pawson AJ, Benson HE, Monaghan AE, Liew WC, Mpamhanga CP, Bonner TI, Neubig RR et al.. (2013)
International Union of Basic and Clinical Pharmacology. LXXXVIII. G protein-coupled receptor list: recommendations for new pairings with cognate ligands.
Pharmacol Rev, 65 (3): 967-86. [PMID:23686350]
7. Fricks IP, Maddileti S, Carter RL, Lazarowski ER, Nicholas RA, Jacobson KA, Harden TK. (2008)
UDP is a competitive antagonist at the human P2Y14 receptor.
J Pharmacol Exp Ther, 325 (2): 588-94. [PMID:18252808]
8. Maekawa A, Balestrieri B, Austen KF, Kanaoka Y. (2009)
GPR17 is a negative regulator of the cysteinyl leukotriene 1 receptor response to leukotriene D4.
Proc Natl Acad Sci USA, 106 (28): 11685-90. [PMID:19561298]
9. Yamada M, Isomoto S, Matsumoto S, Kondo C, Shindo T, Horio Y, Kurachi Y. (1997)
Sulphonylurea receptor 2B and Kir6.1 form a sulphonylurea-sensitive but ATP-insensitive K+ channel.
J Physiol (Lond.), 499 ( Pt 3): 715-20. [PMID:9130167]