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 2011-06-04 _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 Y N 11 R8D C25 N26 TRIP N N 12 R8D C5 C6 DOUB Y N 13 R8D C6 CL27 SING N N 14 R8D C6 C1 SING Y N 15 R8D C12 C11 DOUB Y N 16 R8D C11 C10 SING Y N 17 R8D C10 C9 DOUB Y N 18 R8D C10 O14 SING N N 19 R8D O14 C15 SING N N 20 R8D C15 C16 SING N N 21 R8D C16 N20 DOUB Y N 22 R8D C16 C17 SING Y N 23 R8D N20 N19 SING Y N 24 R8D N19 C18 SING Y N 25 R8D C18 N24 DOUB Y N 26 R8D C18 C17 SING Y N 27 R8D N24 C23 SING Y N 28 R8D C23 C22 DOUB Y N 29 R8D C22 C21 SING Y N 30 R8D C21 C17 DOUB Y N 31 R8D C3 H3 SING N N 32 R8D C5 H5 SING N N 33 R8D C1 H1 SING N N 34 R8D C12 H12 SING N N 35 R8D C11 H11 SING N N 36 R8D C9 H9 SING N N 37 R8D C15 H15 SING N N 38 R8D C15 H15A SING N N 39 R8D N19 HN19 SING N N 40 R8D C23 H23 SING N N 41 R8D C22 H22 SING N 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 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" R8D InChI InChI 1.03 "InChI=1S/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)" R8D InChIKey InChI 1.03 SVMHTBVIPYVDIL-UHFFFAOYSA-N # 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" # loop_ _pdbx_chem_comp_audit.comp_id _pdbx_chem_comp_audit.action_type _pdbx_chem_comp_audit.date _pdbx_chem_comp_audit.processing_site R8D "Create component" 2008-07-16 RCSB R8D "Modify aromatic_flag" 2011-06-04 RCSB R8D "Modify descriptor" 2011-06-04 RCSB #