BAY-091   Click here for help

GtoPdb Ligand ID: 11793

Synonyms: BAY091 | compound 60 [PMID: 34699202]
PDB Ligand
Compound class: Synthetic organic
Comment: BAY-091 is an ATP-competitive inhibitor of the lipid modifying kinase phosphatidylinositol-5-phosphate 4-kinase type 2 alpha (PIP4K2A) [1]. It was designed to aid exploration of the role(s) played by PIP4K2A and -B in pathophysiological conditions such as cancer. BAY-091 directly interacts with PIP4K2A in cells, and inhibits downstream signalling. However, this mechanism failed to translate into the expected phamacodynamic effect of antiproliferative activity in p53-deficient tumour cells, but BAY-091 remains useful as a chemical probe for in vitro analysis of PIP4K2A function.
Click here for help

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.

✖

View interactive charts of activity data across species

BAY-091 is commercially available from our sponsors

2D Structure
Click here for help

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.

✖
Click here for structure editor
Physico-chemical Properties
Click here for help

Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). 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.

✖
Hydrogen bond acceptors 6
Hydrogen bond donors 2
Rotatable bonds 6
Topological polar surface area 98.9
Molecular weight 440.16
XLogP 2.7
No. Lipinski's rules broken 0

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
SMILES / InChI / InChIKey
Click here for help

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.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

✖
Canonical SMILES CC[C@H](C(=O)O)Nc1c(C#N)c(nc2c1ccnc2)c1ccc(cc1)c1cccc(c1F)C
Isomeric SMILES C(#N)c1c(nc2cnccc2c1N[C@@H](C(=O)O)CC)c1ccc(cc1)c1c(c(ccc1)C)F
InChI InChI=1S/C26H21FN4O2/c1-3-21(26(32)33)30-25-19-11-12-29-14-22(19)31-24(20(25)13-28)17-9-7-16(8-10-17)18-6-4-5-15(2)23(18)27/h4-12,14,21H,3H2,1-2H3,(H,30,31)(H,32,33)/t21-/m1/s1
InChI Key DVIVLYHDLNAXAT-OAQYLSRUSA-N

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
Bioactivity Comments
In a commercial kinase screening assay 1 μM BAY-091 did not inhibit any kinases other than PIP4K2A by >60% [1].
Selectivity at enzymes
Key to terms and symbols Click column headers to sort
Target Sp. Type Action Value Parameter Concentration range (M) Reference
phosphatidylinositol-5-phosphate 4-kinase type 2 alpha Hs Inhibitor Inhibition 8.9 pIC50 - 1
⤷ pIC50 8.9 (IC50 1.3x10-9 M) [1]
Description: Determined in an ADPGlo kinase activity assay at 10 μM ATP