data_ZZL
# 
_chem_comp.id                                    ZZL 
_chem_comp.name                                  "4-{[9-CHLORO-7-(2,6-DIFLUOROPHENYL)-5H-PYRIMIDO[5,4-D][2]BENZAZEPIN-2-YL]AMINO}BENZOIC ACID" 
_chem_comp.type                                  non-polymer 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C25 H15 Cl F2 N4 O2" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         ? 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2009-09-22 
_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                        476.862 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     ZZL 
_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        2WTV 
_chem_comp.pdbx_subcomponent_list                ? 
_chem_comp.pdbx_processing_site                  EBI 
# 
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 
ZZL C13  C13  C  0 1 N N N 52.147 30.423 42.352 1.018   -0.634 -2.401 C13  ZZL 1  
ZZL C15  C15  C  0 1 N N N 49.740 30.527 42.365 2.733   -0.818 -0.722 C15  ZZL 2  
ZZL C17  C17  C  0 1 Y N N 47.959 28.923 43.162 4.991   -1.850 -0.483 C17  ZZL 3  
ZZL C20  C20  C  0 1 Y N N 45.922 28.528 41.917 5.490   -3.289 1.368  C20  ZZL 4  
ZZL C21  C21  C  0 1 Y N N 46.345 29.452 40.956 4.206   -3.127 1.855  C21  ZZL 5  
ZZL C22  C22  C  0 1 Y N N 47.573 30.109 41.100 3.301   -2.331 1.177  C22  ZZL 6  
ZZL C24  C24  C  0 1 Y N N 49.551 32.001 42.644 2.693   0.605  -0.350 C24  ZZL 7  
ZZL C26  C26  C  0 1 Y N N 48.336 33.794 43.692 3.956   2.574  0.251  C26  ZZL 8  
ZZL C28  C28  C  0 1 Y N N 49.171 34.735 43.047 2.780   3.296  0.372  C28  ZZL 9  
ZZL O01  O01  O  0 1 N N N 50.362 40.144 38.133 -8.761  -0.703 -1.242 O01  ZZL 10 
ZZL C02  C02  C  0 1 N N N 51.442 39.832 37.764 -8.385  -0.558 -0.095 C02  ZZL 11 
ZZL O03  O03  O  0 1 N N N 52.296 40.774 37.189 -9.235  -0.784 0.926  O03  ZZL 12 
ZZL C04  C04  C  0 1 Y N N 51.889 38.392 37.918 -7.000  -0.135 0.179  C04  ZZL 13 
ZZL C05  C05  C  0 1 Y N N 51.015 37.472 38.504 -6.116  0.100  -0.879 C05  ZZL 14 
ZZL C06  C06  C  0 1 Y N N 51.413 36.144 38.650 -4.824  0.495  -0.620 C06  ZZL 15 
ZZL C07  C07  C  0 1 Y N N 52.684 35.759 38.211 -4.396  0.660  0.694  C07  ZZL 16 
ZZL N08  N08  N  0 1 N N N 53.110 34.404 38.459 -3.088  1.061  0.953  N08  ZZL 17 
ZZL C09  C09  C  0 1 Y N N 52.820 33.382 39.428 -2.060  0.651  0.119  C09  ZZL 18 
ZZL N10  N10  N  0 1 Y N N 53.637 32.262 39.503 -2.323  -0.210 -0.854 N10  ZZL 19 
ZZL C11  C11  C  0 1 Y N N 53.389 31.323 40.437 -1.366  -0.629 -1.666 C11  ZZL 20 
ZZL C12  C12  C  0 1 Y N N 52.339 31.503 41.278 -0.075  -0.153 -1.491 C12  ZZL 21 
ZZL N14  N14  N  0 1 N N N 50.820 29.889 42.240 2.007   -1.373 -1.624 N14  ZZL 22 
ZZL C16  C16  C  0 1 Y N N 48.386 29.844 42.208 3.691   -1.681 0.002  C16  ZZL 23 
ZZL F18  F18  F  0 1 N N N 48.721 28.715 44.263 5.377   -1.226 -1.617 F18  ZZL 24 
ZZL C19  C19  C  0 1 Y N N 46.735 28.259 43.022 5.882   -2.654 0.203  C19  ZZL 25 
ZZL F23  F23  F  0 1 N N N 47.953 31.044 40.181 2.047   -2.174 1.654  F23  ZZL 26 
ZZL C25  C25  C  0 1 Y N N 48.526 32.420 43.481 3.918   1.243  -0.105 C25  ZZL 27 
ZZL CL1  CL1  CL 0 0 N N N 47.038 34.294 44.812 5.482   3.347  0.550  CL1  ZZL 28 
ZZL C29  C29  C  0 1 Y N N 50.205 34.305 42.195 1.568   2.686  0.134  C29  ZZL 29 
ZZL C30  C30  C  0 1 Y N N 50.383 32.932 42.000 1.510   1.335  -0.230 C30  ZZL 30 
ZZL C31  C31  C  0 1 Y N N 51.508 32.637 41.197 0.170   0.756  -0.474 C31  ZZL 31 
ZZL N32  N32  N  0 1 Y N N 51.746 33.572 40.296 -0.843  1.130  0.313  N32  ZZL 32 
ZZL C33  C33  C  0 1 Y N N 53.562 36.675 37.640 -5.273  0.428  1.750  C33  ZZL 33 
ZZL C34  C34  C  0 1 Y N N 53.157 38.002 37.488 -6.568  0.038  1.497  C34  ZZL 34 
ZZL H131 H131 H  0 0 N N N 52.883 29.619 42.205 0.595   -1.285 -3.166 H131 ZZL 35 
ZZL H132 H132 H  0 0 N N N 52.290 30.861 43.351 1.497   0.222  -2.878 H132 ZZL 36 
ZZL H19  H19  H  0 1 N N N 46.420 27.541 43.765 6.886   -2.786 -0.171 H19  ZZL 37 
ZZL H20  H20  H  0 1 N N N 44.973 28.025 41.806 6.192   -3.912 1.902  H20  ZZL 38 
ZZL H21  H21  H  0 1 N N N 45.722 29.660 40.099 3.908   -3.626 2.764  H21  ZZL 39 
ZZL H25  H25  H  0 1 N N N 47.883 31.698 43.963 4.839   0.687  -0.197 H25  ZZL 40 
ZZL H28  H28  H  0 1 N N N 49.014 35.791 43.209 2.813   4.338  0.653  H28  ZZL 41 
ZZL H29  H29  H  0 1 N N N 50.847 35.020 41.702 0.654   3.254  0.230  H29  ZZL 42 
ZZL H03  H03  H  0 1 N N N 51.865 41.620 37.165 -10.134 -1.059 0.696  H03  ZZL 43 
ZZL H05  H05  H  0 1 N N N 50.039 37.788 38.841 -6.448  -0.029 -1.899 H05  ZZL 44 
ZZL H34  H34  H  0 1 N N N 53.823 38.724 37.039 -7.249  -0.139 2.317  H34  ZZL 45 
ZZL H06  H06  H  0 1 N N N 50.747 35.420 39.097 -4.141  0.676  -1.437 H06  ZZL 46 
ZZL H08  H08  H  0 1 N N N 53.779 34.096 37.783 -2.896  1.626  1.717  H08  ZZL 47 
ZZL H33  H33  H  0 1 N N N 54.545 36.363 37.318 -4.937  0.557  2.768  H33  ZZL 48 
ZZL H11  H11  H  0 1 N N N 54.013 30.445 40.515 -1.587  -1.332 -2.455 H11  ZZL 49 
# 
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 
ZZL C13 C12  SING N N 1  
ZZL C13 N14  SING N N 2  
ZZL C15 C24  SING N N 3  
ZZL C15 N14  DOUB N N 4  
ZZL C15 C16  SING N N 5  
ZZL C17 C16  SING Y N 6  
ZZL C17 F18  SING N N 7  
ZZL C17 C19  DOUB Y N 8  
ZZL C20 C21  DOUB Y N 9  
ZZL C20 C19  SING Y N 10 
ZZL C21 C22  SING Y N 11 
ZZL C22 C16  DOUB Y N 12 
ZZL C22 F23  SING N N 13 
ZZL C24 C25  SING Y N 14 
ZZL C24 C30  DOUB Y N 15 
ZZL C26 C28  SING Y N 16 
ZZL C26 C25  DOUB Y N 17 
ZZL C26 CL1  SING N N 18 
ZZL C28 C29  DOUB Y N 19 
ZZL O01 C02  DOUB N N 20 
ZZL C02 O03  SING N N 21 
ZZL C02 C04  SING N N 22 
ZZL C04 C05  SING Y N 23 
ZZL C04 C34  DOUB Y N 24 
ZZL C05 C06  DOUB Y N 25 
ZZL C06 C07  SING Y N 26 
ZZL C07 N08  SING N N 27 
ZZL C07 C33  DOUB Y N 28 
ZZL N08 C09  SING N N 29 
ZZL C09 N10  DOUB Y N 30 
ZZL C09 N32  SING Y N 31 
ZZL N10 C11  SING Y N 32 
ZZL C11 C12  DOUB Y N 33 
ZZL C12 C31  SING Y N 34 
ZZL C29 C30  SING Y N 35 
ZZL C30 C31  SING Y N 36 
ZZL C31 N32  DOUB Y N 37 
ZZL C33 C34  SING Y N 38 
ZZL C13 H131 SING N N 39 
ZZL C13 H132 SING N N 40 
ZZL C19 H19  SING N N 41 
ZZL C20 H20  SING N N 42 
ZZL C21 H21  SING N N 43 
ZZL C25 H25  SING N N 44 
ZZL C28 H28  SING N N 45 
ZZL C29 H29  SING N N 46 
ZZL O03 H03  SING N N 47 
ZZL C05 H05  SING N N 48 
ZZL C34 H34  SING N N 49 
ZZL C06 H06  SING N N 50 
ZZL N08 H08  SING N N 51 
ZZL C33 H33  SING N N 52 
ZZL C11 H11  SING N N 53 
# 
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 
ZZL SMILES           ACDLabs              10.04 "Fc5cccc(F)c5C2=NCc1cnc(nc1c3ccc(Cl)cc23)Nc4ccc(C(=O)O)cc4"                                                                                                                 
ZZL SMILES_CANONICAL CACTVS               3.352 "OC(=O)c1ccc(Nc2ncc3CN=C(c4cc(Cl)ccc4c3n2)c5c(F)cccc5F)cc1"                                                                                                                 
ZZL SMILES           CACTVS               3.352 "OC(=O)c1ccc(Nc2ncc3CN=C(c4cc(Cl)ccc4c3n2)c5c(F)cccc5F)cc1"                                                                                                                 
ZZL SMILES_CANONICAL "OpenEye OEToolkits" 1.6.1 "c1cc(c(c(c1)F)C2=NCc3cnc(nc3-c4c2cc(cc4)Cl)Nc5ccc(cc5)C(=O)O)F"                                                                                                            
ZZL SMILES           "OpenEye OEToolkits" 1.6.1 "c1cc(c(c(c1)F)C2=NCc3cnc(nc3-c4c2cc(cc4)Cl)Nc5ccc(cc5)C(=O)O)F"                                                                                                            
ZZL InChI            InChI                1.03  "InChI=1S/C25H15ClF2N4O2/c26-15-6-9-17-18(10-15)23(21-19(27)2-1-3-20(21)28)29-11-14-12-30-25(32-22(14)17)31-16-7-4-13(5-8-16)24(33)34/h1-10,12H,11H2,(H,33,34)(H,30,31,32)" 
ZZL InChIKey         InChI                1.03  HHFBDROWDBDFBR-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 
ZZL "SYSTEMATIC NAME" ACDLabs              10.04 "4-{[9-chloro-7-(2,6-difluorophenyl)-5H-pyrimido[5,4-d][2]benzazepin-2-yl]amino}benzoic acid" 
ZZL "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.6.1 "4-[[9-chloro-7-(2,6-difluorophenyl)-5H-pyrimido[5,4-d][2]benzazepin-2-yl]amino]benzoic acid" 
# 
loop_
_pdbx_chem_comp_audit.comp_id 
_pdbx_chem_comp_audit.action_type 
_pdbx_chem_comp_audit.date 
_pdbx_chem_comp_audit.processing_site 
ZZL "Create component"     2009-09-22 EBI  
ZZL "Modify aromatic_flag" 2011-06-04 RCSB 
ZZL "Modify descriptor"    2011-06-04 RCSB 
# 
