3PSB

Furo[2,3-c]pyridine-based Indanone Oximes as Potent and Selective B-Raf Inhibitors


Experimental Data Snapshot

  • Method: X-RAY DIFFRACTION
  • Resolution: 3.40 Å
  • R-Value Free: 0.268 
  • R-Value Work: 0.224 
  • R-Value Observed: 0.227 

wwPDB Validation   3D Report Full Report


Ligand Structure Quality Assessment 


This is version 1.3 of the entry. See complete history


Literature

The Discovery of furo[2,3-c]pyridine-based indanone oximes as potent and selective B-Raf inhibitors.

Buckmelter, A.J.Ren, L.Laird, E.R.Rast, B.Miknis, G.Wenglowsky, S.Schlachter, S.Welch, M.Tarlton, E.Grina, J.Lyssikatos, J.Brandhuber, B.J.Morales, T.Randolph, N.Vigers, G.Martinson, M.Callejo, M.

(2011) Bioorg Med Chem Lett 21: 1248-1252

  • DOI: https://doi.org/10.1016/j.bmcl.2010.12.039
  • Primary Citation of Related Structures:  
    3PSB

  • PubMed Abstract: 

    Virtual and high-throughput screening identified imidazo[1,2-a]pyrazines as inhibitors of B-Raf. We describe the rationale, SAR, and evolution of the initial hits to a series of furo[2,3-c]pyridine indanone oximes as highly potent and selective inhibitors of B-Raf.


  • Organizational Affiliation

    Array BioPharma, 3200 Walnut Street, Boulder, CO 80301, USA.


Macromolecules
Find similar proteins by:  (by identity cutoff)  |  3D Structure
Entity ID: 1
MoleculeChains Sequence LengthOrganismDetailsImage
B-RAF PROTO-ONCOGENE SERINE/THREONINE-PROTEIN KINASE
A, B
307Homo sapiensMutation(s): 0 
Gene Names: BRAFBRAF1RAFB1
EC: 2.7.11.1
UniProt & NIH Common Fund Data Resources
Find proteins for P15056 (Homo sapiens)
Explore P15056 
Go to UniProtKB:  P15056
PHAROS:  P15056
GTEx:  ENSG00000157764 
Entity Groups  
Sequence Clusters30% Identity50% Identity70% Identity90% Identity95% Identity100% Identity
UniProt GroupP15056
Sequence Annotations
Expand
  • Reference Sequence
Small Molecules
Ligands 1 Unique
IDChains Name / Formula / InChI Key2D Diagram3D Interactions
SM6
Query on SM6

Download Ideal Coordinates CCD File 
C [auth A],
D [auth B]
ethyl 3-{[1-(hydroxyamino)-2H-inden-5-yl]amino}thieno[2,3-c]pyridine-2-carboxylate
C19 H17 N3 O3 S
CROUIRAPWZHAFI-UHFFFAOYSA-N
Binding Affinity Annotations 
IDSourceBinding Affinity
SM6 PDBBind:  3PSB IC50: 3 (nM) from 1 assay(s)
Experimental Data & Validation

Experimental Data

  • Method: X-RAY DIFFRACTION
  • Resolution: 3.40 Å
  • R-Value Free: 0.268 
  • R-Value Work: 0.224 
  • R-Value Observed: 0.227 
  • Space Group: P 41 21 2
Unit Cell:
Length ( Å )Angle ( ˚ )
a = 101.073α = 90
b = 101.073β = 90
c = 162.952γ = 90
Software Package:
Software NamePurpose
CrystalCleardata collection
MOLREPphasing
REFMACrefinement
MOSFLMdata reduction
SCALAdata scaling

Structure Validation

View Full Validation Report



Ligand Structure Quality Assessment 


Entry History 

Deposition Data

Revision History  (Full details and data files)

  • Version 1.0: 2011-01-19
    Type: Initial release
  • Version 1.1: 2011-07-13
    Changes: Version format compliance
  • Version 1.2: 2018-01-24
    Changes: Structure summary
  • Version 1.3: 2023-09-06
    Changes: Data collection, Database references, Derived calculations, Refinement description