2JJK

FRUCTOSE-1,6-BISPHOSPHATASE(D-FRUCTOSE-1,6-BISPHOSPHATE -1- PHOSPHOHYDROLASE) (E.C.3.1.3.11) COMPLEXED WITH A DUAL BINDING AMP SITE INHIBITOR


Experimental Data Snapshot

  • Method: X-RAY DIFFRACTION
  • Resolution: 2.00 Å
  • R-Value Free: 0.266 
  • R-Value Work: 0.213 
  • R-Value Observed: 0.216 

wwPDB Validation   3D Report Full Report


Ligand Structure Quality Assessment 


This is version 1.2 of the entry. See complete history


Literature

Allosteric Fbpase Inhibitors Gain 10(5) Times in Potency When Simultaneously Binding Two Neighboring AMP Sites.

Hebeisen, P.Kuhn, B.Kohler, P.Gubler, M.Huber, W.Kitas, E.Schott, B.Benz, J.Joseph, C.Ruf, A.

(2008) Bioorg Med Chem Lett 18: 4708

  • DOI: https://doi.org/10.1016/j.bmcl.2008.06.103
  • Primary Citation of Related Structures:  
    2JJK, 2VT5

  • PubMed Abstract: 

    Human fructose-1,6-bisphosphatase (FBPase, EC 3.1.3.11) is a key gluconeogenic enzyme, responsible for the hydrolysis of fructose-1,6-bisphosphate to fructose-6-phosphate, and thus presents an opportunity for the development of novel therapeutics focused on lowering the hepatic glucose production in type 2 diabetics. In its active form FBPase exists as a homotetramer and is allosterically regulated by AMP. In an HTS campaign aromatic sulfonylureas have been identified as FBPase inhibitors mimicking AMP. By bridging two adjacent allosteric binding sites using two aromatic sulfonylureas as anchor units and covalently linking them, it was possible to obtain dual binding AMP site inhibitors that exhibit a strong inhibitory effect.


  • Organizational Affiliation

    F. Hoffmann-La Roche Ltd, Discovery Research Basel, CH-4070 Basel, Switzerland. paul.hebeisen@roche.com


Macromolecules
Find similar proteins by:  (by identity cutoff)  |  3D Structure
Entity ID: 1
MoleculeChains Sequence LengthOrganismDetailsImage
FRUCTOSE-1,6-BISPHOSPHATASE 1
A, B, C, D
338Homo sapiensMutation(s): 0 
EC: 3.1.3.11
UniProt & NIH Common Fund Data Resources
Find proteins for P09467 (Homo sapiens)
Explore P09467 
Go to UniProtKB:  P09467
PHAROS:  P09467
GTEx:  ENSG00000165140 
Entity Groups  
Sequence Clusters30% Identity50% Identity70% Identity90% Identity95% Identity100% Identity
UniProt GroupP09467
Sequence Annotations
Expand
  • Reference Sequence
Small Molecules
Ligands 1 Unique
IDChains Name / Formula / InChI Key2D Diagram3D Interactions
R15
Query on R15

Download Ideal Coordinates CCD File 
E [auth A],
F [auth D]
N,N'-(heptane-1,7-diyldicarbamoyl)bis(3-chlorobenzenesulfonamide)
C21 H26 Cl2 N4 O6 S2
WYYQITAYQRQOJA-UHFFFAOYSA-N
Binding Affinity Annotations 
IDSourceBinding Affinity
R15 BindingDB:  2JJK IC50: min: 4, max: 9 (nM) from 2 assay(s)
Binding MOAD:  2JJK IC50: 9 (nM) from 1 assay(s)
PDBBind:  2JJK IC50: 9 (nM) from 1 assay(s)
Experimental Data & Validation

Experimental Data

  • Method: X-RAY DIFFRACTION
  • Resolution: 2.00 Å
  • R-Value Free: 0.266 
  • R-Value Work: 0.213 
  • R-Value Observed: 0.216 
  • Space Group: P 21 21 21
Unit Cell:
Length ( Å )Angle ( ˚ )
a = 67.176α = 90
b = 83.012β = 90
c = 277.234γ = 90
Software Package:
Software NamePurpose
REFMACrefinement
XDSdata reduction
XSCALEdata 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: 2008-07-22
    Type: Initial release
  • Version 1.1: 2011-05-07
    Changes: Version format compliance
  • Version 1.2: 2011-07-13
    Changes: Version format compliance