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

GtoPdb Ligand ID: 8120

Compound class: Synthetic organic
Comment: The discovery of compound 13d is reported in [1], a medicinal chemistry study to identify selective bone morphogenetic protein receptor (BMP) inhibitors. Compound 13d inhibits all of the Type I receptor serine/threonine kinases to a greater or lesser extent, but is most potent at ALK1 (ACVRL1) and ALK2 (ACVR1) which are activin receptor components, and ALK3 (BMPR1A) and ALK6 (BMPR1B) which are bone morphogenetic protein receptors.
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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 5
Hydrogen bond donors 0
Rotatable bonds 3
Topological polar surface area 55.55
Molecular weight 407.17
XLogP 4.37
No. Lipinski's rules broken 0
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 O1CCN(CC1)c1ccc(cc1)c1cnc2n(c1)ncc2c1ccnc2c1cccc2
Isomeric SMILES O1CCN(CC1)c1ccc(cc1)c1cnc2n(c1)ncc2c1ccnc2c1cccc2
InChI InChI=1S/C25H21N5O/c1-2-4-24-22(3-1)21(9-10-26-24)23-16-28-30-17-19(15-27-25(23)30)18-5-7-20(8-6-18)29-11-13-31-14-12-29/h1-10,15-17H,11-14H2
InChI Key SZVLDZCYMADNPG-UHFFFAOYSA-N
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 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 Primary target of this compound Hs Inhibitor Inhibition >8.3 pIC50 - 1
⤷ pIC50 >8.3 (IC50 <5x10-9 M) [1]
bone morphogenetic protein receptor type IB Primary target of this compound Hs Inhibitor Inhibition >8.3 pIC50 - 1
⤷ pIC50 >8.3 (IC50 <5x10-9 M) [1]
transforming growth factor beta receptor 2 Hs Inhibitor Inhibition 7.6 pIC50 - 1
⤷ pIC50 7.6 (IC50 2.6x10-8 M) [1]
transforming growth factor beta receptor 1 Hs Inhibitor Inhibition 6.8 pIC50 - 1
⤷ pIC50 6.8 (IC50 1.78x10-7 M) [1]
activin A receptor type 1B Hs Inhibitor Inhibition 6.5 pIC50 - 1
⤷ pIC50 6.5 (IC50 3.26x10-7 M) [1]