data_R8D
# 
_chem_comp.id                                    R8D 
_chem_comp.name                                  3-chloro-5-[2-chloro-5-(1H-pyrazolo[3,4-b]pyridin-3-ylmethoxy)phenoxy]benzonitrile 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C20 H12 Cl2 N4 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                        411.241 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     R8D 
_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        3DRS 
_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 
R8D CL28 CL28 CL 0 0 N N N 12.395 12.100 15.407 -3.240 -4.153 -0.519 CL28 R8D 1  
R8D C13  C13  C  0 1 Y N N 10.695 12.536 14.957 -1.839 -3.172 -0.220 C13  R8D 2  
R8D C8   C8   C  0 1 Y N N 9.805  12.370 15.950 -1.961 -1.791 -0.151 C8   R8D 3  
R8D O7   O7   O  0 1 N N N 10.503 11.953 17.004 -3.176 -1.206 -0.317 O7   R8D 4  
R8D C4   C4   C  0 1 Y N N 10.459 12.419 18.226 -3.246 0.150  -0.252 C4   R8D 5  
R8D C3   C3   C  0 1 Y N N 10.189 11.512 19.232 -3.089 0.906  -1.402 C3   R8D 6  
R8D C2   C2   C  0 1 Y N N 10.092 11.846 20.563 -3.162 2.298  -1.332 C2   R8D 7  
R8D C25  C25  C  0 1 N N N 9.884  10.953 21.491 -3.002 3.086  -2.517 C25  R8D 8  
R8D N26  N26  N  0 1 N N N 9.693  10.110 22.369 -2.875 3.712  -3.457 N26  R8D 9  
R8D C5   C5   C  0 1 Y N N 10.669 13.690 18.469 -3.479 0.776  0.965  C5   R8D 10 
R8D C6   C6   C  0 1 Y N N 10.561 13.971 19.772 -3.552 2.156  1.036  C6   R8D 11 
R8D CL27 CL27 CL 0 0 N N N 10.785 15.582 20.041 -3.844 2.929  2.563  CL27 R8D 12 
R8D C1   C1   C  0 1 Y N N 10.286 13.181 20.855 -3.392 2.920  -0.103 C1   R8D 13 
R8D C12  C12  C  0 1 Y N N 10.294 12.993 13.719 -0.603 -3.767 -0.045 C12  R8D 14 
R8D C11  C11  C  0 1 Y N N 8.941  13.247 13.532 0.513  -2.989 0.193  C11  R8D 15 
R8D C10  C10  C  0 1 Y N N 8.030  13.015 14.545 0.397  -1.608 0.258  C10  R8D 16 
R8D C9   C9   C  0 1 Y N N 8.434  12.572 15.838 -0.841 -1.008 0.088  C9   R8D 17 
R8D O14  O14  O  0 1 N N N 6.728  13.233 14.165 1.497  -0.844 0.493  O14  R8D 18 
R8D C15  C15  C  0 1 N N N 5.759  12.208 14.453 2.739  -1.529 0.663  C15  R8D 19 
R8D C16  C16  C  0 1 Y N N 6.024  10.844 13.921 3.836  -0.526 0.912  C16  R8D 20 
R8D N20  N20  N  0 1 Y N N 6.571  10.563 12.710 4.218  -0.078 2.074  N20  R8D 21 
R8D N19  N19  N  0 1 Y N N 6.702  9.142  12.573 5.261  0.840  1.915  N19  R8D 22 
R8D C18  C18  C  0 1 Y N N 6.237  8.483  13.703 5.546  0.973  0.583  C18  R8D 23 
R8D N24  N24  N  0 1 Y N N 6.128  7.122  14.106 6.426  1.697  -0.097 N24  R8D 24 
R8D C23  C23  C  0 1 Y N N 5.608  6.715  15.317 6.495  1.640  -1.409 C23  R8D 25 
R8D C22  C22  C  0 1 Y N N 5.151  7.686  16.198 5.653  0.820  -2.146 C22  R8D 26 
R8D C21  C21  C  0 1 Y N N 5.270  9.072  15.842 4.723  0.047  -1.500 C21  R8D 27 
R8D C17  C17  C  0 1 Y N N 5.794  9.489  14.589 4.664  0.114  -0.104 C17  R8D 28 
R8D H3   H3   H  0 1 N N N 10.045 10.478 18.957 -2.911 0.420  -2.350 H3   R8D 29 
R8D H5   H5   H  0 1 N N N 10.901 14.421 17.709 -3.605 0.183  1.859  H5   R8D 30 
R8D H1   H1   H  0 1 N N N 10.225 13.572 21.860 -3.449 3.996  -0.044 H1   R8D 31 
R8D H12  H12  H  0 1 N N N 11.007 13.148 12.923 -0.511 -4.842 -0.094 H12  R8D 32 
R8D H11  H11  H  0 1 N N N 8.597  13.631 12.583 1.477  -3.457 0.329  H11  R8D 33 
R8D H9   H9   H  0 1 N N N 7.743  12.409 16.651 -0.933 0.066  0.142  H9   R8D 34 
R8D H15  H15  H  0 1 N N N 5.704  12.119 15.548 2.666  -2.207 1.514  H15  R8D 35 
R8D H15A H15A H  0 0 N N N 4.838  12.537 13.950 2.966  -2.099 -0.237 H15A R8D 36 
R8D HN19 HN19 H  0 0 N N N 7.079  8.685  11.768 5.712  1.309  2.635  HN19 R8D 37 
R8D H23  H23  H  0 1 N N N 5.558  5.667  15.574 7.225  2.246  -1.925 H23  R8D 38 
R8D H22  H22  H  0 1 N N N 4.710  7.402  17.142 5.729  0.791  -3.223 H22  R8D 39 
R8D H21  H21  H  0 1 N N N 4.951  9.822  16.550 4.057  -0.598 -2.054 H21  R8D 40 
# 
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 
R8D CL28 C13  SING N N 1  
R8D C13  C8   DOUB Y N 2  
R8D C13  C12  SING Y N 3  
R8D C8   O7   SING N N 4  
R8D C8   C9   SING Y N 5  
R8D O7   C4   SING N N 6  
R8D C4   C3   DOUB Y N 7  
R8D C4   C5   SING Y N 8  
R8D C3   C2   SING Y N 9  
R8D C2   C25  SING N N 10 
R8D C2   C1   DOUB N N 11 
R8D C25  N26  TRIP Y N 12 
R8D C5   C6   DOUB N N 13 
R8D C6   CL27 SING Y N 14 
R8D C6   C1   SING N N 15 
R8D C12  C11  DOUB N N 16 
R8D C11  C10  SING Y N 17 
R8D C10  C9   DOUB N N 18 
R8D C10  O14  SING Y N 19 
R8D O14  C15  SING N N 20 
R8D C15  C16  SING Y N 21 
R8D C16  N20  DOUB N N 22 
R8D C16  C17  SING Y N 23 
R8D N20  N19  SING N N 24 
R8D N19  C18  SING N N 25 
R8D C18  N24  DOUB N N 26 
R8D C18  C17  SING N N 27 
R8D N24  C23  SING N N 28 
R8D C23  C22  DOUB N N 29 
R8D C22  C21  SING Y N 30 
R8D C21  C17  DOUB Y N 31 
R8D C3   H3   SING Y N 32 
R8D C5   H5   SING Y N 33 
R8D C1   H1   SING N N 34 
R8D C12  H12  SING Y N 35 
R8D C11  H11  SING Y N 36 
R8D C9   H9   SING Y N 37 
R8D C15  H15  SING Y N 38 
R8D C15  H15A SING N N 39 
R8D N19  HN19 SING Y N 40 
R8D C23  H23  SING N N 41 
R8D C22  H22  SING Y N 42 
R8D C21  H21  SING N N 43 
# 
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 
R8D SMILES           ACDLabs              10.04 N#Cc4cc(Oc3c(Cl)ccc(OCc2nnc1ncccc12)c3)cc(Cl)c4                                                                                              
R8D InChI            InChI                1.02b InChI=1/C20H12Cl2N4O2/c21-13-6-12(10-23)7-15(8-13)28-19-9-14(3-4-17(19)22)27-11-18-16-2-1-5-24-20(16)26-25-18/h1-9H,11H2,(H,24,25,26)/f/h26H 
R8D InChIKey         InChI                1.02b SVMHTBVIPYVDIL-HXTKINSTCH                                                                                                                    
R8D SMILES_CANONICAL CACTVS               3.341 Clc1cc(Oc2cc(OCc3n[nH]c4ncccc34)ccc2Cl)cc(c1)C#N                                                                                             
R8D SMILES           CACTVS               3.341 Clc1cc(Oc2cc(OCc3n[nH]c4ncccc34)ccc2Cl)cc(c1)C#N                                                                                             
R8D SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 c1cc2c(n[nH]c2nc1)COc3ccc(c(c3)Oc4cc(cc(c4)Cl)C#N)Cl                                                                                         
R8D SMILES           "OpenEye OEToolkits" 1.5.0 c1cc2c(n[nH]c2nc1)COc3ccc(c(c3)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 
R8D "SYSTEMATIC NAME" ACDLabs              10.04 3-chloro-5-[2-chloro-5-(1H-pyrazolo[3,4-b]pyridin-3-ylmethoxy)phenoxy]benzonitrile 
R8D "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 3-chloro-5-[2-chloro-5-(1H-pyrazolo[5,4-b]pyridin-3-ylmethoxy)phenoxy]benzonitrile 
# 
