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
References
1. Engers DW, Frist AY, Lindsley CW, Hong CC, Hopkins CR. (2013)
Synthesis and structure-activity relationships of a novel and selective bone morphogenetic protein receptor (BMP) inhibitor derived from the pyrazolo[1.5-a]pyrimidine scaffold of dorsomorphin: the discovery of ML347 as an ALK2 versus ALK3 selective MLPCN probe.
Bioorg. Med. Chem. Lett., 23 (11): 3248-52. [PMID:23639540]