staurosporine   Click here for help

GtoPdb Ligand ID: 346

Synonyms: (+)-staurosporine | antibiotic 230 | antibiotic AM-2282
PDB Ligand
Compound class: Natural product or derivative
Comment: Staurosporine is a non-specific, ATP-competitive inhibitor of protein kinase C (PKC) isolated from a Streptomyces strain [10]. It inhibits all PKC enzyme isoforms [2,13], but has a more potent inhibitory effect on PKCs associated with the cell membrane compared to cytosolic PKCs.
Staurosporine analogues such as midostaurin and 7-hydroxystaurosporine are being investigated as therapeutics.
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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

staurosporine 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 5
Hydrogen bond donors 2
Rotatable bonds 2
Topological polar surface area 69.45
Molecular weight 466.2
XLogP 6.05
No. Lipinski's rules broken 1
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 CNC1CC2OC(C1OC)(C)n1c3ccccc3c3c1c1n2c2ccccc2c1c1c3CNC1=O
Isomeric SMILES CN[C@@H]1C[C@H]2O[C@]([C@@H]1OC)(C)n1c3ccccc3c3c1c1n2c2ccccc2c1c1c3CNC1=O
InChI InChI=1S/C28H26N4O3/c1-28-26(34-3)17(29-2)12-20(35-28)31-18-10-6-4-8-14(18)22-23-16(13-30-27(23)33)21-15-9-5-7-11-19(15)32(28)25(21)24(22)31/h4-11,17,20,26,29H,12-13H2,1-3H3,(H,30,33)/t17-,20-,26-,28+/m1/s1
InChI Key HKSZLNNOFSGOKW-FYTWVXJKSA-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: 3,14
Key to terms and symbols Click column headers to sort
Target Name in screen Sp. Type Action Value Parameter
STE20 like kinase SLK Hs Inhibitor Inhibition 10.6 pKd
serine/threonine kinase 10 LOK Hs Inhibitor Inhibition 10.4 pKd
calcium/calmodulin dependent protein kinase kinase 1 CAMKK1 Hs Inhibitor Inhibition 10.4 pKd
NUAK family, SNF1-like kinase, 2 SNARK Hs Inhibitor Inhibition 10.1 pKd
phosphorylase kinase catalytic subunit gamma 2 PHKG2 Hs Inhibitor Inhibition 9.9 pKd
calcium/calmodulin-dependent protein kinase II alpha subunit CAMK2A Hs Inhibitor Inhibition 9.8 pKd
calcium/calmodulin dependent protein kinase kinase 2 CAMKK2 Hs Inhibitor Inhibition 9.8 pKd
serine/threonine kinase 3 MST2 Hs Inhibitor Inhibition 9.7 pKd
serine/threonine kinase 4 MST1 Hs Inhibitor Inhibition 9.7 pKd
fms related receptor tyrosine kinase 3 FLT3(R834Q) Hs Inhibitor Inhibition 9.7 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: 1,5
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
protein kinase C gamma PKCγ/PKCg Hs Inhibitor Inhibition -3.2 1.5 1.0
calcium/calmodulin dependent protein kinase kinase 1 nd/CAMKK1 Hs Inhibitor Inhibition -3.1
ribosomal protein S6 kinase A3 Rsk2/RSK2 Hs Inhibitor Inhibition -1.3 0.0 0.0
TANK binding kinase 1 TBK1/TBK1 Hs Inhibitor Inhibition -0.5 1.5 0.5
serine/threonine kinase 4 MST1/MST1(STK4) Hs Inhibitor Inhibition -0.2 -0.5 1.0
microtubule affinity regulating kinase 2 PAR-1Bα/MARK2(PAR-1Ba) Hs Inhibitor Inhibition 0.0 -1.0 0.0
microtubule affinity regulating kinase 4 nd/MARK4 Hs Inhibitor Inhibition 0.0
salt inducible kinase 2 nd/SIK2 Hs Inhibitor Inhibition 0.1
ribosomal protein S6 kinase B1 p70S6K/p70S6K(RPS6KB1) Hs Inhibitor Inhibition 0.1 1.5 3.0
protein kinase N1 nd/PKN1(PRK1) Hs Inhibitor Inhibition 0.1
Displaying the top 10 targets  View all targets in screen »