4ZGX

Structure of aldosterone synthase (CYP11B2) in complex with (+)-(R)-N-(4-(4-chloro-3-fluorophenyl)-5,6,7,8-tetrahydroisoquinolin-8-yl)propionamide


Experimental Data Snapshot

  • Method: X-RAY DIFFRACTION
  • Resolution: 3.20 Å
  • R-Value Free: 0.255 
  • R-Value Work: 0.212 
  • R-Value Observed: 0.214 

Starting Model: other
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Ligand Structure Quality Assessment 


This is version 1.2 of the entry. See complete history


Literature

Discovery of 4-Aryl-5,6,7,8-tetrahydroisoquinolines as Potent, Selective, and Orally Active Aldosterone Synthase (CYP11B2) Inhibitors: In Vivo Evaluation in Rodents and Cynomolgus Monkeys.

Martin, R.E.Aebi, J.D.Hornsperger, B.Krebs, H.J.Kuhn, B.Kuglstatter, A.Alker, A.M.Marki, H.P.Muller, S.Burger, D.Ottaviani, G.Riboulet, W.Verry, P.Tan, X.Amrein, K.Mayweg, A.V.

(2015) J Med Chem 58: 8054-8065

  • DOI: https://doi.org/10.1021/acs.jmedchem.5b00851
  • Primary Citation of Related Structures:  
    4ZGX

  • PubMed Abstract: 

    Inappropriately high levels of aldosterone are associated with many serious medical conditions, including renal and cardiac failure. A focused screen hit has been optimized into a potent and selective aldosterone synthase (CYP11B2) inhibitor with in vitro activity against rat, mouse, human, and cynomolgus monkey enzymes, showing a selectivity factor of 160 against cytochrome CYP11B1 in the last species. The novel tetrahydroisoquinoline compound (+)-(R)-6 selectively reduced aldosterone plasma levels in vivo in a dose-dependent manner in db/db mice and cynomolgus monkeys. The selectivity against CYP11B1 as predicted by cellular inhibition data and free plasma fraction translated well to Synacthen challenged cynomolgus monkeys up to a dose of 0.1 mg kg(-1). This compound, displaying good in vivo potency and selectivity in mice and monkeys, is ideally suited to perform mechanistic studies in relevant rodent models and to provide the information necessary for translation to non-human primates and ultimately to man.


  • Organizational Affiliation

    Medicinal Chemistry, Roche Pharma Research and Early Development (pRED), Roche Innovation Center Basel, F. Hoffmann-La Roche Ltd. , Grenzacherstrasse 124, CH-4070 Basel, Switzerland.


Macromolecules
Find similar proteins by:  (by identity cutoff)  |  3D Structure
Entity ID: 1
MoleculeChains Sequence LengthOrganismDetailsImage
Cytochrome P450 11B2, mitochondrial
A, B, C, D, E
A, B, C, D, E, F, G, H, I, J, K, L
489Homo sapiensMutation(s): 0 
Gene Names: CYP11B2
EC: 1.14.15.4 (PDB Primary Data), 1.14.15.5 (PDB Primary Data)
UniProt & NIH Common Fund Data Resources
Find proteins for P19099 (Homo sapiens)
Explore P19099 
Go to UniProtKB:  P19099
PHAROS:  P19099
GTEx:  ENSG00000179142 
Entity Groups  
Sequence Clusters30% Identity50% Identity70% Identity90% Identity95% Identity100% Identity
UniProt GroupP19099
Sequence Annotations
Expand
  • Reference Sequence
Small Molecules
Ligands 2 Unique
IDChains Name / Formula / InChI Key2D Diagram3D Interactions
HEM
Query on HEM

Download Ideal Coordinates CCD File 
AA [auth I]
CA [auth J]
EA [auth K]
GA [auth L]
M [auth A]
AA [auth I],
CA [auth J],
EA [auth K],
GA [auth L],
M [auth A],
O [auth B],
Q [auth C],
S [auth D],
U [auth E],
W [auth F],
Y [auth G],
Z [auth H]
PROTOPORPHYRIN IX CONTAINING FE
C34 H32 Fe N4 O4
KABFMIBPWCXCRK-RGGAHWMASA-L
QHC
Query on QHC

Download Ideal Coordinates CCD File 
BA [auth I]
DA [auth J]
FA [auth K]
HA [auth L]
N [auth A]
BA [auth I],
DA [auth J],
FA [auth K],
HA [auth L],
N [auth A],
P [auth B],
R [auth C],
T [auth D],
V [auth E],
X [auth F]
N-[(8R)-4-(4-chloro-3-fluorophenyl)-5,6,7,8-tetrahydroisoquinolin-8-yl]propanamide
C18 H18 Cl F N2 O
BTXHAHICPWSTRI-QGZVFWFLSA-N
Binding Affinity Annotations 
IDSourceBinding Affinity
QHC BindingDB:  4ZGX IC50: 14 (nM) from 1 assay(s)
EC50: min: 7, max: 3.14e+4 (nM) from 6 assay(s)
Experimental Data & Validation

Experimental Data

  • Method: X-RAY DIFFRACTION
  • Resolution: 3.20 Å
  • R-Value Free: 0.255 
  • R-Value Work: 0.212 
  • R-Value Observed: 0.214 
  • Space Group: P 1
Unit Cell:
Length ( Å )Angle ( ˚ )
a = 104.7α = 70.25
b = 125.96β = 85.87
c = 155.23γ = 73.84
Software Package:
Software NamePurpose
BUSTERrefinement
XDSdata reduction
Aimlessdata scaling
PHASERphasing

Structure Validation

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Ligand Structure Quality Assessment 


Entry History 

Deposition Data

Revision History  (Full details and data files)

  • Version 1.0: 2015-10-07
    Type: Initial release
  • Version 1.1: 2015-11-04
    Changes: Database references
  • Version 1.2: 2024-05-01
    Changes: Data collection, Database references, Derived calculations, Refinement description