data_R8E
# 
_chem_comp.id                                    R8E 
_chem_comp.name                                  3-{5-[(6-amino-1H-pyrazolo[3,4-b]pyridin-3-yl)methoxy]-2-chlorophenoxy}-5-chlorobenzonitrile 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C20 H13 Cl2 N5 O2" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         ? 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2008-07-16 
_chem_comp.pdbx_modified_date                    2008-10-14 
_chem_comp.pdbx_ambiguous_flag                   N 
_chem_comp.pdbx_release_status                   REL 
_chem_comp.pdbx_replaced_by                      ? 
_chem_comp.pdbx_replaces                         ? 
_chem_comp.formula_weight                        426.256 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     R8E 
_chem_comp.pdbx_model_coordinates_details        ? 
_chem_comp.pdbx_model_coordinates_missing_flag   N 
_chem_comp.pdbx_ideal_coordinates_details        Corina 
_chem_comp.pdbx_ideal_coordinates_missing_flag   N 
_chem_comp.pdbx_model_coordinates_db_code        3DRP 
_chem_comp.pdbx_subcomponent_list                ? 
_chem_comp.pdbx_processing_site                  RCSB 
# 
loop_
_chem_comp_atom.comp_id 
_chem_comp_atom.atom_id 
_chem_comp_atom.alt_atom_id 
_chem_comp_atom.type_symbol 
_chem_comp_atom.charge 
_chem_comp_atom.pdbx_align 
_chem_comp_atom.pdbx_aromatic_flag 
_chem_comp_atom.pdbx_leaving_atom_flag 
_chem_comp_atom.pdbx_stereo_config 
_chem_comp_atom.model_Cartn_x 
_chem_comp_atom.model_Cartn_y 
_chem_comp_atom.model_Cartn_z 
_chem_comp_atom.pdbx_model_Cartn_x_ideal 
_chem_comp_atom.pdbx_model_Cartn_y_ideal 
_chem_comp_atom.pdbx_model_Cartn_z_ideal 
_chem_comp_atom.pdbx_component_atom_id 
_chem_comp_atom.pdbx_component_comp_id 
_chem_comp_atom.pdbx_ordinal 
R8E CL29 CL29 CL 0 0 N N N 13.019 11.983 15.496 -3.743 -3.978 -0.780 CL29 R8E 1  
R8E C13  C13  C  0 1 Y N N 11.325 12.369 15.118 -2.297 -3.105 -0.380 C13  R8E 2  
R8E C8   C8   C  0 1 Y N N 10.543 12.252 16.162 -2.334 -1.723 -0.251 C8   R8E 3  
R8E O7   O7   O  0 1 N N N 11.234 11.904 17.267 -3.502 -1.053 -0.436 O7   R8E 4  
R8E C4   C4   C  0 1 Y N N 10.894 12.512 18.492 -3.488 0.300  -0.311 C4   R8E 5  
R8E C3   C3   C  0 1 Y N N 10.459 11.694 19.559 -3.237 1.095  -1.416 C3   R8E 6  
R8E C2   C2   C  0 1 Y N N 10.101 12.237 20.792 -3.224 2.484  -1.284 C2   R8E 7  
R8E C26  C26  C  0 1 N N N 9.768  11.491 21.784 -2.965 3.312  -2.423 C26  R8E 8  
R8E N27  N27  N  0 1 N N N 9.483  10.850 22.638 -2.759 3.969  -3.327 N27  R8E 9  
R8E C5   C5   C  0 1 Y N N 10.942 13.914 18.647 -3.733 0.885  0.925  C5   R8E 10 
R8E C6   C6   C  0 1 Y N N 10.581 14.439 19.922 -3.721 2.262  1.059  C6   R8E 11 
R8E CL28 CL28 CL 0 0 N N N 10.609 16.184 20.297 -4.027 2.984  2.607  CL28 R8E 12 
R8E C1   C1   C  0 1 Y N N 10.175 13.645 20.995 -3.465 3.064  -0.037 C1   R8E 13 
R8E C12  C12  C  0 1 Y N N 10.890 12.772 13.897 -1.110 -3.787 -0.186 C12  R8E 14 
R8E C11  C11  C  0 1 Y N N 9.555  13.051 13.865 0.043  -3.094 0.132  C11  R8E 15 
R8E C10  C10  C  0 1 Y N N 8.731  12.936 14.905 0.012  -1.712 0.258  C10  R8E 16 
R8E C9   C9   C  0 1 Y N N 9.178  12.506 16.097 -1.178 -1.027 0.068  C9   R8E 17 
R8E O14  O14  O  0 1 N N N 7.421  13.270 14.769 1.146  -1.032 0.571  O14  R8E 18 
R8E C15  C15  C  0 1 N N N 6.656  13.121 13.615 2.335  -1.804 0.757  C15  R8E 19 
R8E C16  C16  C  0 1 Y N N 6.602  11.626 13.553 3.481  -0.886 1.096  C16  R8E 20 
R8E N20  N20  N  0 1 Y N N 6.855  10.904 12.450 3.843  -0.516 2.291  N20  R8E 21 
R8E N19  N19  N  0 1 Y N N 6.718  9.556  12.837 4.948  0.337  2.216  N19  R8E 22 
R8E C18  C18  C  0 1 Y N N 6.382  9.385  14.085 5.295  0.509  0.904  C18  R8E 23 
R8E N24  N24  N  0 1 Y N N 6.150  8.288  14.801 6.249  1.205  0.294  N24  R8E 24 
R8E C23  C23  C  0 1 Y N N 5.806  8.349  16.108 6.370  1.201  -1.021 C23  R8E 25 
R8E N25  N25  N  0 1 N N N 5.601  7.053  16.792 7.384  1.943  -1.612 N25  R8E 26 
R8E C22  C22  C  0 1 Y N N 5.676  9.564  16.765 5.501  0.465  -1.829 C22  R8E 27 
R8E C21  C21  C  0 1 Y N N 5.927  10.739 16.025 4.502  -0.269 -1.253 C21  R8E 28 
R8E C17  C17  C  0 1 Y N N 6.277  10.630 14.662 4.390  -0.258 0.144  C17  R8E 29 
R8E H3   H3   H  0 1 N N N 10.403 10.625 19.416 -3.050 0.641  -2.378 H3   R8E 30 
R8E H5   H5   H  0 1 N N N 11.239 14.561 17.835 -3.933 0.262  1.785  H5   R8E 31 
R8E H1   H1   H  0 1 N N N 9.925  14.084 21.949 -3.457 4.138  0.071  H1   R8E 32 
R8E H12  H12  H  0 1 N N N 11.536 12.863 13.037 -1.084 -4.862 -0.282 H12  R8E 33 
R8E H11  H11  H  0 1 N N N 9.136  13.390 12.929 0.969  -3.629 0.284  H11  R8E 34 
R8E H9   H9   H  0 1 N N N 8.523  12.368 16.945 -1.204 0.048  0.169  H9   R8E 35 
R8E H15  H15  H  0 1 N N N 5.662  13.585 13.695 2.184  -2.513 1.571  H15  R8E 36 
R8E H15A H15A H  0 0 N N N 7.063  13.611 12.718 2.563  -2.347 -0.160 H15A R8E 37 
R8E HN19 HN19 H  0 0 N N N 6.866  8.794  12.207 5.397  0.743  2.974  HN19 R8E 38 
R8E HN25 HN25 H  0 0 N N N 5.555  6.321  16.113 7.993  2.458  -1.060 HN25 R8E 39 
R8E HN2A HN2A H  0 0 N N N 6.364  6.881  17.416 7.482  1.947  -2.577 HN2A R8E 40 
R8E H22  H22  H  0 1 N N N 5.393  9.609  17.806 5.618  0.475  -2.903 H22  R8E 41 
R8E H21  H21  H  0 1 N N N 5.852  11.708 16.495 3.818  -0.845 -1.859 H21  R8E 42 
# 
loop_
_chem_comp_bond.comp_id 
_chem_comp_bond.atom_id_1 
_chem_comp_bond.atom_id_2 
_chem_comp_bond.value_order 
_chem_comp_bond.pdbx_aromatic_flag 
_chem_comp_bond.pdbx_stereo_config 
_chem_comp_bond.pdbx_ordinal 
R8E CL29 C13  SING N N 1  
R8E C13  C8   DOUB Y N 2  
R8E C13  C12  SING Y N 3  
R8E C8   O7   SING N N 4  
R8E C8   C9   SING Y N 5  
R8E O7   C4   SING N N 6  
R8E C4   C3   DOUB Y N 7  
R8E C4   C5   SING Y N 8  
R8E C3   C2   SING Y N 9  
R8E C2   C26  SING N N 10 
R8E C2   C1   DOUB N N 11 
R8E C26  N27  TRIP Y N 12 
R8E C5   C6   DOUB N N 13 
R8E C6   CL28 SING Y N 14 
R8E C6   C1   SING N N 15 
R8E C12  C11  DOUB N N 16 
R8E C11  C10  SING Y N 17 
R8E C10  C9   DOUB N N 18 
R8E C10  O14  SING Y N 19 
R8E O14  C15  SING N N 20 
R8E C15  C16  SING Y N 21 
R8E C16  N20  DOUB N N 22 
R8E C16  C17  SING Y N 23 
R8E N20  N19  SING N N 24 
R8E N19  C18  SING N N 25 
R8E C18  N24  DOUB N N 26 
R8E C18  C17  SING N N 27 
R8E N24  C23  SING N N 28 
R8E C23  N25  SING N N 29 
R8E C23  C22  DOUB Y N 30 
R8E C22  C21  SING Y N 31 
R8E C21  C17  DOUB Y N 32 
R8E C3   H3   SING Y N 33 
R8E C5   H5   SING N N 34 
R8E C1   H1   SING Y N 35 
R8E C12  H12  SING Y N 36 
R8E C11  H11  SING Y N 37 
R8E C9   H9   SING N N 38 
R8E C15  H15  SING Y N 39 
R8E C15  H15A SING N N 40 
R8E N19  HN19 SING N N 41 
R8E N25  HN25 SING Y N 42 
R8E N25  HN2A SING N N 43 
R8E C22  H22  SING Y N 44 
R8E C21  H21  SING N N 45 
# 
loop_
_pdbx_chem_comp_descriptor.comp_id 
_pdbx_chem_comp_descriptor.type 
_pdbx_chem_comp_descriptor.program 
_pdbx_chem_comp_descriptor.program_version 
_pdbx_chem_comp_descriptor.descriptor 
R8E SMILES           ACDLabs              10.04 N#Cc4cc(Oc3c(Cl)ccc(OCc2nnc1nc(ccc12)N)c3)cc(Cl)c4                                                                                                       
R8E InChI            InChI                1.02b InChI=1/C20H13Cl2N5O2/c21-12-5-11(9-23)6-14(7-12)29-18-8-13(1-3-16(18)22)28-10-17-15-2-4-19(24)25-20(15)27-26-17/h1-8H,10H2,(H3,24,25,26,27)/f/h27H,24H2 
R8E InChIKey         InChI                1.02b KXDIHAQCVNNLIB-MDBBYRAECL                                                                                                                                
R8E SMILES_CANONICAL CACTVS               3.341 Nc1ccc2c(COc3ccc(Cl)c(Oc4cc(Cl)cc(c4)C#N)c3)n[nH]c2n1                                                                                                    
R8E SMILES           CACTVS               3.341 Nc1ccc2c(COc3ccc(Cl)c(Oc4cc(Cl)cc(c4)C#N)c3)n[nH]c2n1                                                                                                    
R8E SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 c1cc(c(cc1OCc2c3ccc(nc3[nH]n2)N)Oc4cc(cc(c4)Cl)C#N)Cl                                                                                                    
R8E SMILES           "OpenEye OEToolkits" 1.5.0 c1cc(c(cc1OCc2c3ccc(nc3[nH]n2)N)Oc4cc(cc(c4)Cl)C#N)Cl                                                                                                    
# 
loop_
_pdbx_chem_comp_identifier.comp_id 
_pdbx_chem_comp_identifier.type 
_pdbx_chem_comp_identifier.program 
_pdbx_chem_comp_identifier.program_version 
_pdbx_chem_comp_identifier.identifier 
R8E "SYSTEMATIC NAME" ACDLabs              10.04 3-{5-[(6-amino-1H-pyrazolo[3,4-b]pyridin-3-yl)methoxy]-2-chlorophenoxy}-5-chlorobenzonitrile   
R8E "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 3-[5-[(6-amino-1H-pyrazolo[5,4-b]pyridin-3-yl)methoxy]-2-chloro-phenoxy]-5-chloro-benzonitrile 
# 
