PI-103   Click here for help

GtoPdb Ligand ID: 5701

Synonyms: compound 2 [PMID: 17601739] | PI 103 | PIK 103
PDB Ligand
Compound class: Synthetic organic
Comment: The discovery of PI-103 is described in [5], where it is compound 10e. It was originally identified as a PI3Kα/β inhibitor, but has subsequently been found to inhibit catalytic activity of all four PI3K subunits (α, β, γ and δ) [8].
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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
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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Click here for structure editor
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 5
Hydrogen bond donors 1
Rotatable bonds 2
Topological polar surface area 84.51
Molecular weight 348.12
XLogP 2.97
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 Oc1cccc(c1)c1nc(N2CCOCC2)c2c(n1)c1cccnc1o2
Isomeric SMILES Oc1cccc(c1)c1nc(N2CCOCC2)c2c(n1)c1cccnc1o2
InChI InChI=1S/C19H16N4O3/c24-13-4-1-3-12(11-13)17-21-15-14-5-2-6-20-19(14)26-16(15)18(22-17)23-7-9-25-10-8-23/h1-6,11,24H,7-10H2
InChI Key TUVCWJQQGGETHL-UHFFFAOYSA-N

Large-scale screening data

DiscoveRx KINOMEscan® screen Click here for help
A screen of 72 inhibitors against 456 human kinases. Quantitative data were derived using DiscoveRx KINOMEscan® platform.
http://www.discoverx.com/services/drug-discovery-development-services/kinase-profiling/kinomescan
Reference: 2,9
Key to terms and symbols Click column headers to sort
Target Name in screen Sp. Type Action Value Parameter
phosphatidylinositol-4,5-bisphosphate 3-kinase catalytic subunit alpha PIK3CA(C420R) Hs Inhibitor Inhibition 8.9 pKd
phosphatidylinositol-4,5-bisphosphate 3-kinase catalytic subunit alpha PIK3CA(E542K) Hs Inhibitor Inhibition 8.9 pKd
phosphatidylinositol-4,5-bisphosphate 3-kinase catalytic subunit alpha PIK3CA Hs Inhibitor Inhibition 8.8 pKd
phosphatidylinositol-4,5-bisphosphate 3-kinase catalytic subunit alpha PIK3CA(E545A) Hs Inhibitor Inhibition 8.8 pKd
phosphatidylinositol-4,5-bisphosphate 3-kinase catalytic subunit alpha PIK3CA(E545K) Hs Inhibitor Inhibition 8.8 pKd
phosphatidylinositol-4,5-bisphosphate 3-kinase catalytic subunit alpha PIK3CA(Q546K) Hs Inhibitor Inhibition 8.8 pKd
phosphatidylinositol-4,5-bisphosphate 3-kinase catalytic subunit beta PIK3CB Hs Inhibitor Inhibition 8.8 pKd
phosphatidylinositol-4,5-bisphosphate 3-kinase catalytic subunit alpha PIK3CA(I800L) Hs Inhibitor Inhibition 8.5 pKd
phosphatidylinositol-4,5-bisphosphate 3-kinase catalytic subunit alpha PIK3CA(M1043I) Hs Inhibitor Inhibition 8.5 pKd
phosphatidylinositol-4,5-bisphosphate 3-kinase catalytic subunit alpha PIK3CA(H1047L) Hs Inhibitor Inhibition 8.5 pKd
Displaying the top 10 targets  View all targets in screen »
EMD Millipore KinaseProfilerTM screen/Reaction Biology Kinase HotspotSM screen Click here for help
A screen profiling 158 kinase inhibitors (Calbiochem Protein Kinase Inhibitor Library I and II, catalogue numbers 539744 and 539745) for their inhibitory activity at 1µM and 10µM against 234 human recombinant kinases using the EMD Millipore KinaseProfilerTM service.

A screen profiling the inhibitory activity of 178 commercially available kinase inhibitors at 0.5µM against a panel of 300 recombinant protein kinases using the Reaction Biology Corporation Kinase HotspotSM platform.

http://www.millipore.com/techpublications/tech1/pf3036
http://www.reactionbiology.com/webapps/main/pages/kinase.aspx

Reference: 1,4
Key to terms and symbols Click column headers to sort
Target Name in screen Sp. Type Action % Activity remaining at 0.5µM % Activity remaining at 1µM % Activity remaining at 10µM
casein kinase 2, alpha prime polypeptide subunit CK2α2/CK2a2 Hs Inhibitor Inhibition 56.2 140.0 79.0
tyrosine kinase 2 nd/TYK2 Hs Inhibitor Inhibition 73.6
NUAK family, SNF1-like kinase, 2 nd/SNARK(NUAK2) Hs Inhibitor Inhibition 75.3
maternal embryonic leucine zipper kinase MELK/MELK Hs Inhibitor Inhibition 75.5 74.0 88.0
myosin light chain kinase MLCK/MLCK(MYLK) Hs Inhibitor Inhibition 77.1 71.0 72.0
NIMA related kinase 1 nd/NEK1 Hs Inhibitor Inhibition 77.8
cyclin dependent kinase 5 CDK5-p25/CDK5-p25 Hs Inhibitor Inhibition 77.9 90.0 103.0
death associated protein kinase 1 DAPK1/DAPK1 Hs Inhibitor Inhibition 78.0 99.0 76.0
EPH receptor A6 nd/EPHA6 Hs Inhibitor Inhibition 79.0
Raf-1 proto-oncogene, serine/threonine kinase c-RAF/RAF1 Hs Inhibitor Inhibition 79.1 81.0 91.0
Displaying the top 10 targets  View all targets in screen »