compound 13r [PMID: 23639540]   Click here for help

GtoPdb Ligand ID: 8144

Compound class: Synthetic organic
Comment: Compound 13r is one of the analogues assessed in a study to identify selective inhibitors of bone morphogenetic protein receptor isotypes [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
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 5
Hydrogen bond donors 0
Rotatable bonds 3
Topological polar surface area 49.56
Molecular weight 420.21
XLogP 4.41
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 CN1CCN(CC1)c1ccc(cc1)c1cnc2n(c1)ncc2c1ccnc2c1cccc2
Isomeric SMILES CN1CCN(CC1)c1ccc(cc1)c1cnc2n(c1)ncc2c1ccnc2c1cccc2
InChI InChI=1S/C26H24N6/c1-30-12-14-31(15-13-30)21-8-6-19(7-9-21)20-16-28-26-24(17-29-32(26)18-20)22-10-11-27-25-5-3-2-4-23(22)25/h2-11,16-18H,12-15H2,1H3
InChI Key XBGWAKUQSRNWMA-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/)
Bioactivity Comments
Compound 13r shows little selectivity across the members of the Type I receptor serine/threonine kinases family, which contains the bone morphogenetic protein receptors, and also inhibits transforming growth factor, beta receptor II (TGFBR2, a Type II receptor serine/threonine kinase) with IC50 of 15nM [1].
We have tagged ALK1/ACVRL1 as primary target for compound 13r based only on the fact that this is the first member of the protein family, with several members being equally sensitive to compound 13r inhibition.
Selectivity at catalytic receptors
Key to terms and symbols Click column headers to sort
Target Sp. Type Action Value Parameter Concentration range (M) Reference
activin A receptor type IL Primary target of this compound Hs Inhibitor Inhibition >8.3 pIC50 - 1
⤷ pIC50 >8.3 (IC50 <5x10-9 M) [1]
activin A receptor type 1 Hs Inhibitor Inhibition >8.3 pIC50 - 1
⤷ pIC50 >8.3 (IC50 <5x10-9 M) [1]
bone morphogenetic protein receptor type IA Hs Inhibitor Inhibition >8.3 pIC50 - 1
⤷ pIC50 >8.3 (IC50 <5x10-9 M) [1]
bone morphogenetic protein receptor type IB Hs Inhibitor Inhibition >8.3 pIC50 - 1
⤷ pIC50 >8.3 (IC50 <5x10-9 M) [1]
transforming growth factor beta receptor 1 Hs Inhibitor Inhibition 7.1 pIC50 - 1
⤷ pIC50 7.1 (IC50 7.5x10-8 M) [1]
activin A receptor type 1B Hs Inhibitor Inhibition 6.7 pIC50 - 1
⤷ pIC50 6.7 (IC50 1.83x10-7 M) [1]