compound 13d [PMID: 23639540]   

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.
2D Structure
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Physico-chemical Properties
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
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 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 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]