compound 52 [PMID: 9677190]   Click here for help

GtoPdb Ligand ID: 5955

PDB Ligand
Compound class: Synthetic organic
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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 6
Hydrogen bond donors 3
Rotatable bonds 6
Topological polar surface area 87.89
Molecular weight 346.13
XLogP 3.17
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 OCCNc1nc(Nc2cccc(c2)Cl)c2c(n1)n(cn2)C(C)C
Isomeric SMILES OCCNc1nc(Nc2cccc(c2)Cl)c2c(n1)n(cn2)C(C)C
InChI InChI=1S/C16H19ClN6O/c1-10(2)23-9-19-13-14(20-12-5-3-4-11(17)8-12)21-16(18-6-7-24)22-15(13)23/h3-5,8-10,24H,6-7H2,1-2H3,(H2,18,20,21,22)
InChI Key XZEFMZCNXDQXOZ-UHFFFAOYSA-N

Large-scale screening data

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: 1,3
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 1 gamma 3 CK1γ3/CK1g3 Hs Inhibitor Inhibition 6.9 56.0 13.0
fms related receptor tyrosine kinase 3 Flt3/FLT3 Hs Inhibitor Inhibition 15.1 20.0 1.0
casein kinase 1 gamma 1 CK1γ1/CK1g1 Hs Inhibitor Inhibition 16.0 8.0 0.0
casein kinase 1 gamma 2 CK1γ2/CK1g2 Hs Inhibitor Inhibition 20.6 4.0 -9.0
cyclin dependent kinase 5 CDK5-p35/CDK5-p35 Hs Inhibitor Inhibition 22.7 8.0 1.0
Janus kinase 3 JAK3/JAK3 Hs Inhibitor Inhibition 24.7 111.0 81.0
CDC like kinase 2 CLK2/CLK2 Hs Inhibitor Inhibition 25.0 19.0 6.0
cyclin dependent kinase 5 CDK5-p25/CDK5-p25 Hs Inhibitor Inhibition 26.2 3.0 0.0
mitogen-activated protein kinase kinase kinase 9 MLK1/MLK19MAP3K90 Hs Inhibitor Inhibition 27.2 11.0 1.0
neurotrophic receptor tyrosine kinase 3 nd/TRKC Hs Inhibitor Inhibition 30.7
Displaying the top 10 targets  View all targets in screen »