compound 3 [PMID: 29633584]   Click here for help

GtoPdb Ligand ID: 9960

Immunopharmacology Ligand
Compound class: Synthetic organic
Comment: This compound 3 is a lead chemical scaffold for the further development of lysine demethylase 6B (KDM6B, also known as JMJD3 and Jumonji D3) inhibitors. JMJD3 is an inducible enzyme, that along with ubiquitously transcribed X chromosome tetratricopeptide repeat protein (UTX), forms the KDM6 subfamily of histone modifying enzymes, which catalyze the demethylation of lysine 27 on histone H3 (H3K27). H3K27 demethylases are involved in maintaining the epigenetic transcriptional state in replicating and postmitotic cells. Prior to the discovery of compound 3, GSK-J1 and its derivatives were the only selective KDM6 inhibitors to be reported [5-6]. Compound 3 is suitable for investigating the role of JMJD3 in normal tissues and in tissues that are altered by pathological conditions, such as cancer and inflammation.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 7
Hydrogen bond donors 2
Rotatable bonds 5
Topological polar surface area 131.73
Molecular weight 355.08
XLogP 2.29
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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Canonical SMILES COc1nc(OC)ncc1c1cnc2c(c1)c(ccc2C(=O)O)C(=O)O
Isomeric SMILES COc1nc(OC)ncc1c1cnc2c(c1)c(ccc2C(=O)O)C(=O)O
InChI InChI=1S/C17H13N3O6/c1-25-14-12(7-19-17(20-14)26-2)8-5-11-9(15(21)22)3-4-10(16(23)24)13(11)18-6-8/h3-7H,1-2H3,(H,21,22)(H,23,24)
InChI Key CAGSRYBLIZYFGG-UHFFFAOYSA-N
Classification Click here for help
Compound class Synthetic organic
IUPAC Name Click here for help
3-(2,4-dimethoxypyrimidin-5-yl)quinoline-5,8-dicarboxylic acid
Database Links Click here for help
GtoPdb PubChem SID 374883847
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