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 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 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 Y N 11 R8E C26 N27 TRIP N N 12 R8E C5 C6 DOUB Y N 13 R8E C6 CL28 SING N N 14 R8E C6 C1 SING Y N 15 R8E C12 C11 DOUB Y N 16 R8E C11 C10 SING Y N 17 R8E C10 C9 DOUB Y N 18 R8E C10 O14 SING N N 19 R8E O14 C15 SING N N 20 R8E C15 C16 SING N N 21 R8E C16 N20 DOUB Y N 22 R8E C16 C17 SING Y N 23 R8E N20 N19 SING Y N 24 R8E N19 C18 SING Y N 25 R8E C18 N24 DOUB Y N 26 R8E C18 C17 SING Y N 27 R8E N24 C23 SING Y 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 N N 33 R8E C5 H5 SING N N 34 R8E C1 H1 SING N N 35 R8E C12 H12 SING N N 36 R8E C11 H11 SING N N 37 R8E C9 H9 SING N N 38 R8E C15 H15 SING N N 39 R8E C15 H15A SING N N 40 R8E N19 HN19 SING N N 41 R8E N25 HN25 SING N N 42 R8E N25 HN2A SING N N 43 R8E C22 H22 SING N 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 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" R8E InChI InChI 1.03 "InChI=1S/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)" R8E InChIKey InChI 1.03 KXDIHAQCVNNLIB-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 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" # loop_ _pdbx_chem_comp_audit.comp_id _pdbx_chem_comp_audit.action_type _pdbx_chem_comp_audit.date _pdbx_chem_comp_audit.processing_site R8E "Create component" 2008-07-16 RCSB R8E "Modify aromatic_flag" 2011-06-04 RCSB R8E "Modify descriptor" 2011-06-04 RCSB #