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compound E3   Click here for help

GtoPdb Ligand ID: 14091

PDB Ligand
Compound class: Synthetic organic
Comment: Compound E3 functions as an inhibitor of the facilitative urea transporters UT-A and UT-B [1-2].
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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 Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). 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 7
Hydrogen bond donors 2
Rotatable bonds 7
Topological polar surface area 109.95
Molecular weight 384.41
XLogP 0.68
No. Lipinski's rules broken 0

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
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.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

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Canonical SMILES CC(=O)C1=CC=C(C(=O)NC2=CC=CC(=C2)NS(=O)(=O)C3=CC=CC=C3)O1
Isomeric SMILES CC(=O)C1=CC=C(O1)C(=O)NC2=CC(NS(=O)(=O)C3=CC=CC=C3)=CC=C2
InChI InChI=1S/C19H16N2O5S/c1-13(22)17-10-11-18(26-17)19(23)20-14-6-5-7-15(12-14)21-27(24,25)16-8-3-2-4-9-16/h2-12,21H,1H3,(H,20,23)
InChI Key OCEJOLAYBZXXRB-UHFFFAOYSA-N

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
Selectivity at transporters
Key to terms and symbols Click column headers to sort
Target Sp. Type Action Value Parameter Concentration range (M) Reference
Erythrocyte urea transporter Rn Inhibitor Inhibition 8.1 pIC50 - 1-2
⤷ pIC50 8.1 (IC50 7.6x10-9 M) [1-2]
Description: Determined as inhibition of UT-B-promoted urea transport in the red blood cell lysis assay
Kidney urea transporter Hs Inhibitor Inhibition 7.7 pIC50 - 1-2
⤷ pIC50 7.7 (IC50 1.9x10-8 M) [1-2]
Description: Measured as inhibition of UT-A1-mediated urea permeability in MDCK cell lines stably expressing rat UT-A1, determined in a transwell assay
Erythrocyte urea transporter Hs Inhibitor Inhibition 7.6 pIC50 - 1-2
⤷ pIC50 7.6 (IC50 2.5x10-8 M) [1-2]
Description: Determined as inhibition of UT-B-promoted urea transport in the red blood cell lysis assay
Erythrocyte urea transporter Mm Inhibitor Inhibition 7.3 pIC50 - 1-2
⤷ pIC50 7.3 (IC50 4.77x10-8 M) [1-2]
Description: Determined as inhibition of UT-B-promoted urea transport in the red blood cell lysis assay