compound 21 [PMID: 22802221]   Click here for help

GtoPdb Ligand ID: 6918

Synonyms: 3-[4-(1H-imidazol-1-ylmethyl)phenyl]-5-(2-methylpropyl)thiophene-2-[(N-butyloxylcarbamate)-sulphonamide] sodium salt | C21
Immunopharmacology Ligand
Compound class: Synthetic organic
Comment: Compound 21 is a first-in-class orally administered angiotensin AT2 receptor agonist. It prevents TNFα-induced and HFD-induced vascular inflammation in vitro and in vivo, indicating that its anti-atherosclerotic actions are due to vascular anti-inflammatory effects, mediated by AT2 receptors [2]. C21 is one of the chemical structures that are claimed in Vicore Pharma's patent US20180078529A1 [1].
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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

compound 21 [PMID: 22802221] is commercially available from our sponsors

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 6
Hydrogen bond donors 1
Rotatable bonds 12
Topological polar surface area 126.91
Molecular weight 475.16
XLogP 4.33
No. Lipinski's rules broken 1

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 CCCCOC(=O)NS(=O)(=O)c1sc(cc1c1ccc(cc1)Cn1cncc1)CC(C)C
Isomeric SMILES CCCCOC(=O)NS(=O)(=O)c1sc(cc1c1ccc(cc1)Cn1cncc1)CC(C)C
InChI InChI=1S/C23H29N3O4S2/c1-4-5-12-30-23(27)25-32(28,29)22-21(14-20(31-22)13-17(2)3)19-8-6-18(7-9-19)15-26-11-10-24-16-26/h6-11,14,16-17H,4-5,12-13,15H2,1-3H3,(H,25,27)
InChI Key XTEOJPUYZWEXFI-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/)
Immunopharmacology Comments
Compound 21 is an adenosine AT2 receptor agonist that exhibits vascular anti-inflammatory effects in vitro and in vivo [2].