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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2D Structure
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Physico-chemical Properties
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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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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
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SynPHARM 85248 (in complex with mitogen-activated protein kinase 1)