GSK-J4   Click here for help

GtoPdb Ligand ID: 8979

Synonyms: GSK J4 | GSKJ4
Immunopharmacology Ligand
Compound class: Synthetic organic
Comment: GSK-J4 is a cell permeable inhibitor of the histone lysine demethylase KDM6 enzymes, lysine (K)-specific demethylase 6A and 6B (common abbrevations UTX and JMJD3 respectively) [2]. It is the ethyl ester prodrug of GSK-J1. GSK-J4 blocks demethylation of histone H3K27.
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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

GSK-J4 is commercially available from our sponsors

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 7
Hydrogen bond donors 1
Rotatable bonds 8
Topological polar surface area 80.24
Molecular weight 417.22
XLogP 4.45
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 CCOC(=O)CCNc1cc(nc(n1)c1ccccn1)N1CCc2c(CC1)cccc2
Isomeric SMILES CCOC(=O)CCNc1cc(nc(n1)c1ccccn1)N1CCc2c(CC1)cccc2
InChI InChI=1S/C24H27N5O2/c1-2-31-23(30)10-14-26-21-17-22(28-24(27-21)20-9-5-6-13-25-20)29-15-11-18-7-3-4-8-19(18)12-16-29/h3-9,13,17H,2,10-12,14-16H2,1H3,(H,26,27,28)
InChI Key WBKCKEHGXNWYMO-UHFFFAOYSA-N
Classification Click here for help
Compound class Synthetic organic
Is prodrug? Yes
Active form GSK-J1
IUPAC Name Click here for help
ethyl 3-{[2-(pyridin-2-yl)-6-(2,3,4,5-tetrahydro-1H-3-benzazepin-3-yl)pyrimidin-4-yl]amino}propanoate
Synonyms Click here for help
GSK J4 | GSKJ4
Database Links Click here for help
CAS Registry No. 1373423-53-0 (source: PubChem)
ChEMBL Ligand CHEMBL3183531
GtoPdb PubChem SID 310264759
PubChem CID 71729975
Search Google for chemical match using the InChIKey WBKCKEHGXNWYMO-UHFFFAOYSA-N
Search Google for chemicals with the same backbone WBKCKEHGXNWYMO
UniChem Compound Search for chemical match using the InChIKey WBKCKEHGXNWYMO-UHFFFAOYSA-N
UniChem Connectivity Search for chemical match using the InChIKey WBKCKEHGXNWYMO-UHFFFAOYSA-N

Product suppliers

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Tocris
GSK J4 (links to external site)
Cat. No. 4594