compound 27 [PMID: 29775310]   Click here for help

GtoPdb Ligand ID: 9973

PDB Ligand
Compound class: Synthetic organic
Comment: Compound 27 is a lead ERK1/2 inhibitor that was identified using biophysical fragment screening and structure-based optimization [1]. It was found to be potent, selective and orally bioavailable. Compound 27 inhibits both the catalytic kinase (phosphorylating) activity of ERK1/2, and the phosphorylation of ERK1/2. It is an alternative chemotype to SCH772984, but it retains the dual activity profile that was originally identified in SCH772984. Compound 27 has improved in vivo exposure compared to SCH772984.
(Note: ERK1= MAPK3, ERK2= MAPK1).
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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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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 9
Hydrogen bond donors 3
Rotatable bonds 9
Topological polar surface area 116.68
Molecular weight 549.21
XLogP 3.58
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 OCC(c1cccc(c1)C)NC(=O)C(N1Cc2c(C1=O)cc(cc2)c1nc(ncc1Cl)NC1CCOCC1)C
Isomeric SMILES OC[C@H](c1cccc(c1)C)NC(=O)[C@H](N1Cc2c(C1=O)cc(cc2)c1nc(ncc1Cl)NC1CCOCC1)C
InChI InChI=1S/C29H32ClN5O4/c1-17-4-3-5-19(12-17)25(16-36)33-27(37)18(2)35-15-21-7-6-20(13-23(21)28(35)38)26-24(30)14-31-29(34-26)32-22-8-10-39-11-9-22/h3-7,12-14,18,22,25,36H,8-11,15-16H2,1-2H3,(H,33,37)(H,31,32,34)/t18-,25-/m1/s1
InChI Key XHOJEECXVUMYMF-IQGLISFBSA-N
Classification Click here for help
Compound class Synthetic organic
IUPAC Name Click here for help
(2R)-2-[5-[5-chloro-2-(oxan-4-ylamino)pyrimidin-4-yl]-3-oxo-1H-isoindol-2-yl]-N-[(1S)-2-hydroxy-1-(3-methylphenyl)ethyl]propanamide
Database Links Click here for help
GtoPdb PubChem SID 374883860
PubChem CID 129053491
RCSB PDB Ligand ESN
Search Google for chemical match using the InChIKey XHOJEECXVUMYMF-IQGLISFBSA-N
Search Google for chemicals with the same backbone XHOJEECXVUMYMF
SynPHARM 85248 (in complex with mitogen-activated protein kinase 1)
UniChem Compound Search for chemical match using the InChIKey XHOJEECXVUMYMF-IQGLISFBSA-N
UniChem Connectivity Search for chemical match using the InChIKey XHOJEECXVUMYMF-IQGLISFBSA-N