5BPE

Crystal structure of EV71 3Cpro in complex with a potent and selective Inhibitor

Experimental Data Snapshot

  • Method: X-RAY DIFFRACTION
  • Resolution: 2.70 Å
  • R-Value Free: 0.281 
  • R-Value Work: 0.163 
  • R-Value Observed: 0.168 

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This is version 1.3 of the entry. See complete history. 


Literature

Cyanohydrin as an Anchoring Group for Potent and Selective Inhibitors of Enterovirus 71 3C Protease

Zhai, Y., Zhao, X., Cui, Z., Wang, M., Wang, Y., Li, L., Sun, Q., Yang, X., Zeng, D., Liu, Y., Sun, Y., Lou, Z., Shang, L., Yin, Z.

(2015) J Med Chem 58: 9414-9420

  • DOI: https://doi.org/10.1021/acs.jmedchem.5b01013
  • Primary Citation of Related Structures:  
    5BPE

  • PubMed Abstract: 

    Cyanohydrin derivatives as enterovirus 71 (EV71) 3C protease (3C(pro)) inhibitors have been synthesized and assayed for their biochemical and antiviral activities. Compared with the reported inhibitors, cyanohydrins (1S,2S,2'S,5S)-16 and (1R,2S,2'S,5S)-16 exhibited significantly improved activity and attractive selectivity profiles against other proteases, which were a result of the specific interactions between the cyanohydrin moiety and the catalytic site of 3C(pro). Cyanohydrin as an anchoring group with high selectivity and excellent inhibitory activity represents a useful choice for cysteine protease inhibitors.

    • Organizational Affiliation: 

    College of Pharmacy and State Key Laboratory of Elemento-Organic Chemistry, Nankai University , 94 Weijin Road, Nankai District, Tianjin 300071, China.


Macromolecules
Find similar proteins by: 
(by identity cutoff)  |  3D Structure
Entity ID: 1
MoleculeChains Sequence LengthOrganismDetailsImage
EV71 3Cpro180Enterovirus A71Mutation(s): 0 
UniProt
Find proteins for A0A0X1KHD2 (Human enterovirus 71)
Explore A0A0X1KHD2 
Go to UniProtKB:  A0A0X1KHD2
Entity Groups  
Sequence Clusters30% Identity50% Identity70% Identity90% Identity95% Identity100% Identity
UniProt GroupA0A0X1KHD2
Sequence Annotations
Expand
  • Reference Sequence
Small Molecules
Ligands 1 Unique
IDChains Name / Formula / InChI Key2D Diagram3D Interactions
E22
Query on E22
Download Ideal Coordinates CCD File 
B [auth A](2~{S})-~{N}-[(1~{R},2~{S})-1-cyano-1-oxidanyl-3-[(3~{S})-2-oxidanylidenepiperidin-3-yl]propan-2-yl]-3-phenyl-2-[[(~{E})-3-phenylprop-2-enoyl]amino]propanamide
C27 H30 N4 O4
UJFNOZFDUMAJFU-XSAZPJIKSA-N
Experimental Data & Validation

Experimental Data

  • Method: X-RAY DIFFRACTION
  • Resolution: 2.70 Å
  • R-Value Free: 0.281 
  • R-Value Work: 0.163 
  • R-Value Observed: 0.168 
  • Space Group: C 1 2 1
Unit Cell:
Length ( Å )Angle ( ˚ )
a = 76.766α = 90
b = 63.271β = 116.97
c = 38.76γ = 90
Software Package:
Software NamePurpose
PHENIXrefinement
HKL-2000data reduction
HKL-2000data scaling
PHASERphasing

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: 2015-11-25
    Type: Initial release
  • Version 1.1: 2015-12-09
    Changes: Database references
  • Version 1.2: 2016-01-20
    Changes: Database references
  • Version 1.3: 2024-03-20
    Changes: Data collection, Database references, Derived calculations