GSK-J1   Click here for help

GtoPdb Ligand ID: 7027

PDB Ligand Immunopharmacology Ligand
Compound class: Synthetic organic
Comment: GSK-J1 is a catalytic site inhibitor that is somewhat selective for the H3K27me3-specific demethylases KDM6A and 6B (a.k.a. UTX and JMJD3 respectively) [2]. The compund has also been shown to inhibit H3K4me3/me2 catalysed by KDM5 enzymes in vitro [1].
This is a compound from the Structural Genomics Consortium's (SGC) Epigenetics Probes Collection. It reduces lipopolysaccharide-induced proinflammatory cytokine production by human primary macrophages, a process that depends on both JMJD3 and UTX.
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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 6
Topological polar surface area 91.24
Molecular weight 389.19
XLogP 3.71
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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Canonical SMILES OC(=O)CCNc1nc(nc(c1)N1CCc2ccccc2CC1)c1ccccn1
Isomeric SMILES OC(=O)CCNc1nc(nc(c1)N1CCc2ccccc2CC1)c1ccccn1
InChI InChI=1S/C22H23N5O2/c28-21(29)8-12-24-19-15-20(26-22(25-19)18-7-3-4-11-23-18)27-13-9-16-5-1-2-6-17(16)10-14-27/h1-7,11,15H,8-10,12-14H2,(H,28,29)(H,24,25,26)
InChI Key AVZCPICCWKMZDT-UHFFFAOYSA-N
Classification Click here for help
Compound class Synthetic organic
Prodrug GSK-J4
IUPAC Name Click here for help
3-{[2-(pyridin-2-yl)-6-(2,3,4,5-tetrahydro-1H-3-benzazepin-3-yl)pyrimidin-4-yl]amino}propanoic acid
Database Links Click here for help
CAS Registry No. 1373422-53-7 (source: Scifinder)
ChEMBL Ligand CHEMBL3188597
GtoPdb PubChem SID 178103606
PubChem CID 56963315
RCSB PDB Ligand K0I, URY
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SynPHARM 83291 (in complex with lysine demethylase 5B)

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Tocris
GSK J1
Cat. No. 4593