2P33

Synthesis and SAR of Aminopyrimidines as Novel c-Jun N-Terminal Kinase (JNK) Inhibitors

Experimental Data Snapshot

  • Method: X-RAY DIFFRACTION
  • Resolution: 2.40 Å
  • R-Value Free: 0.304 
  • R-Value Work: 0.253 

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This is version 1.4 of the entry. See complete history. 


Literature

Synthesis and SAR of aminopyrimidines as novel c-Jun N-terminal kinase (JNK) inhibitors

Alam, M., Beevers, R.E., Ceska, T., Davenport, R.J., Dickson, K.M., Fortunato, M., Gowers, L., Haughan, A.F., James, L.A., Jones, M.W., Kinsella, N., Lowe, C., Meissner, J.W., Nicolas, A.L., Perry, B.G., Phillips, D.J., Pitt, W.R., Platt, A., Ratcliffe, A.J., Sharpe, A., Tait, L.J.

(2007) Bioorg Med Chem Lett 17: 3463-3467

  • DOI: https://doi.org/10.1016/j.bmcl.2007.03.078
  • Primary Citation of Related Structures:  
    2P33

  • PubMed Abstract: 

    The development of a series of novel aminopyrimidines as inhibitors of c-Jun N-terminal kinases is described. The synthesis, in vitro inhibitory values for JNK1, JNK2 and CDK2, and the in vitro inhibitory value for a c-Jun cellular assay are discussed.

    • Organizational Affiliation: 

    UCB, Granta Park, Great Abington, Cambridge CB21 6GS, UK.


Macromolecules
Find similar proteins by: 
(by identity cutoff)  |  3D Structure
Entity ID: 1
MoleculeChains Sequence LengthOrganismDetailsImage
c-Jun N-terminal kinase 3365Homo sapiensMutation(s): 0 
Gene Names: MAPK10, JNK3, JNK3A, PRKM10
EC: 2.7.11.24
UniProt & NIH Common Fund Data Resources
Find proteins for P53779 (Homo sapiens)
Explore P53779 
Go to UniProtKB:  P53779
PHAROS:  P53779
GTEx:  ENSG00000109339 
Entity Groups  
Sequence Clusters30% Identity50% Identity70% Identity90% Identity95% Identity100% Identity
UniProt GroupP53779
Sequence Annotations
Expand
  • Reference Sequence
Small Molecules
Ligands 1 Unique
IDChains Name / Formula / InChI Key2D Diagram3D Interactions
J07
Query on J07
Download Ideal Coordinates CCD File 
B [auth A]4-{[5-chloro-4-(1H-indol-3-yl)pyrimidin-2-yl]amino}-N-ethylpiperidine-1-carboxamide
C20 H23 Cl N6 O
ARMFMDYRYOKSOW-UHFFFAOYSA-N
Binding Affinity Annotations 
IDSourceBinding Affinity
J07 PDBBind:  2P33 IC50: 57 (nM) from 1 assay(s)
BindingDB:  2P33 IC50: min: 13, max: 57 (nM) from 3 assay(s)
Binding MOAD:  2P33 IC50: 57 (nM) from 1 assay(s)
Experimental Data & Validation

Experimental Data

  • Method: X-RAY DIFFRACTION
  • Resolution: 2.40 Å
  • R-Value Free: 0.304 
  • R-Value Work: 0.253 
  • Space Group: P 21 21 21
Unit Cell:
Length ( Å )Angle ( ˚ )
a = 51.82α = 90
b = 71.52β = 90
c = 107.36γ = 90
Software Package:
Software NamePurpose
CNXrefinement
MAR345dtbdata collection
DENZOdata reduction
SCALEPACKdata scaling
CNXphasing

Structure Validation

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Ligand Structure Quality Assessment 


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Entry History 

Deposition Data

Revision History  (Full details and data files)

  • Version 1.0: 2007-06-19
    Type: Initial release
  • Version 1.1: 2008-05-01
    Changes: Version format compliance
  • Version 1.2: 2011-07-13
    Changes: Version format compliance
  • Version 1.3: 2017-10-18
    Changes: Refinement description
  • Version 1.4: 2023-08-30
    Changes: Data collection, Database references, Derived calculations, Refinement description