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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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
Natural/Endogenous Targets
Target
GPR17
P2Y14 receptor
P2Y6 receptor
Enzymes Catalysing Reactions with this Compound as a Substrate or Product
Enzyme EC number Reaction Reference
UDP-glucose ceramide glucosyltransferase 2.4.1.80 UDP-glucose + ceramide = UDP + glucosylceramide
Selectivity at GPCRs
Key to terms and symbols Click column headers to sort
Target Sp. Type Action Value Parameter Concentration range (M) Reference
GPR17 Ligand is endogenous in the given species Hs Agonist Agonist 6.0 – 8.8 pEC50 - 1,4
⤷ pEC50 6.0 – 8.8 (EC50 1.06x10-6 – 1.6x10-9 M) [1,4]
Description: [35S]GTPγS binding to 1321N1 cell membranes expressing hGPR17.
P2Y14 receptor Ligand is endogenous in the given species Hs Agonist Full agonist 7.1 pEC50 - 3
⤷ pEC50 7.1 (EC50 7.4x10-8 M) [3]
P2Y6 receptor Ligand is endogenous in the given species Hs Agonist Full agonist 6.5 pEC50 - 5
⤷ pEC50 6.5 [5]
P2Y14 receptor Ligand is endogenous in the given species Rn Agonist Full agonist 6.5 pIC50 - 7
⤷ pIC50 6.5 [7]
Selectivity at ion channels
Key to terms and symbols Click column headers to sort
Target Sp. Type Action Value Parameter Concentration range (M) Reference
Kir6.1 Mm Activator Agonist - - 1x10-3 9
⤷ Conc range: 1x10-3 M [9]
Voltage: -60.0 – 60.0 mV
Additional information and targets (data relate to human unless otherwise stated)
Description Data Reference
Potency order of endogenous ligands at P2Y14 receptor UDP= UDP-glucose
Potency order of endogenous ligands at P2Y6 receptor UDP >> UTP > ADP
Targets where the ligand is described in the comment field
Target Comment
GPR17 Reported to be a dual leukotriene and UDP receptor [4]. Another group instead proposed that GPR17 functions as a negative regulator of the CysLT1 receptor response to leukotriene D4 (LTD4). For further discussion, see [6]. Reported to antagonize CysLT1 receptor signalling in vivo and in vitro [8]. See reviews [2] and [6].
Ligand mentioned in the following text fields
P2Y receptors overview