data_AW8
# 
_chem_comp.id                                    AW8 
_chem_comp.name                                  "2-[(1~{R})-5-(4-chlorophenyl)-9-fluoranyl-3-methyl-1-oxidanyl-1~{H}-pyrimido[4,5-c]quinolin-2-yl]ethanoic acid" 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C20 H15 Cl F N3 O3" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         ? 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2017-08-24 
_chem_comp.pdbx_modified_date                    2018-05-04 
_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                        399.803 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     AW8 
_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        5OUJ 
_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 
AW8 CL1 CL1 CL 0 0 N N N 4.004  -14.908 6.718  -6.716 -0.050 0.241  CL1 AW8 1  
AW8 C16 C1  C  0 1 Y N N 4.233  -13.553 7.886  -5.004 -0.326 0.167  C16 AW8 2  
AW8 C14 C2  C  0 1 Y N N 3.150  -13.130 8.645  -4.522 -1.569 -0.207 C14 AW8 3  
AW8 C12 C3  C  0 1 Y N N 3.311  -12.097 9.568  -3.162 -1.794 -0.268 C12 AW8 4  
AW8 C15 C4  C  0 1 Y N N 5.466  -12.920 8.053  -4.126 0.699  0.476  C15 AW8 5  
AW8 C13 C5  C  0 1 Y N N 5.605  -11.875 8.973  -2.764 0.485  0.418  C13 AW8 6  
AW8 C11 C6  C  0 1 Y N N 4.521  -11.455 9.742  -2.273 -0.767 0.048  C11 AW8 7  
AW8 C10 C7  C  0 1 Y N N 4.646  -10.310 10.694 -0.812 -1.003 -0.015 C10 AW8 8  
AW8 N9  N1  N  0 1 Y N N 5.668  -10.208 11.600 -0.331 -2.184 0.318  N9  AW8 9  
AW8 C2  C8  C  0 1 Y N N 5.841  -9.161  12.470 0.978  -2.451 0.280  C2  AW8 10 
AW8 C4  C9  C  0 1 Y N N 6.911  -9.135  13.372 1.466  -3.716 0.650  C4  AW8 11 
AW8 C6  C10 C  0 1 Y N N 7.093  -8.077  14.271 2.803  -3.967 0.604  C6  AW8 12 
AW8 C5  C11 C  0 1 Y N N 6.205  -6.999  14.286 3.706  -2.985 0.195  C5  AW8 13 
AW8 F27 F1  F  0 1 N N N 6.335  -5.932  15.128 5.027  -3.265 0.161  F27 AW8 14 
AW8 C3  C12 C  0 1 Y N N 5.149  -7.038  13.386 3.271  -1.746 -0.172 C3  AW8 15 
AW8 C8  C13 C  0 1 Y N N 3.640  -9.212  10.588 0.044  0.042  -0.438 C8  AW8 16 
AW8 N19 N2  N  0 1 N N N 2.980  -8.861  9.428  -0.457 1.265  -0.779 N19 AW8 17 
AW8 C20 C14 C  0 1 N N N 2.408  -7.699  9.202  0.320  2.296  -0.938 C20 AW8 18 
AW8 C22 C15 C  0 1 N N N 1.663  -7.407  7.933  -0.268 3.617  -1.363 C22 AW8 19 
AW8 N18 N3  N  0 1 N N N 2.541  -6.667  10.066 1.670  2.190  -0.720 N18 AW8 20 
AW8 C17 C16 C  0 1 N N R 2.784  -7.086  11.423 2.327  0.901  -0.988 C17 AW8 21 
AW8 O21 O1  O  0 1 N N N 2.912  -5.978  12.247 2.559  0.759  -2.391 O21 AW8 22 
AW8 C7  C17 C  0 1 Y N N 3.822  -8.114  11.531 1.408  -0.194 -0.510 C7  AW8 23 
AW8 C1  C18 C  0 1 Y N N 4.952  -8.097  12.501 1.898  -1.452 -0.137 C1  AW8 24 
AW8 C23 C19 C  0 1 N N N 1.789  -5.429  9.978  2.441  3.336  -0.232 C23 AW8 25 
AW8 C24 C20 C  0 1 N N N 0.362  -5.414  10.403 2.458  3.325  1.275  C24 AW8 26 
AW8 O25 O2  O  0 1 N N N -0.197 -6.519  10.591 3.110  4.287  1.946  O25 AW8 27 
AW8 O26 O3  O  0 1 N N N -0.124 -4.258  10.546 1.884  2.450  1.879  O26 AW8 28 
AW8 H1  H1  H  0 1 N N N 2.185  -13.600 8.521  -5.211 -2.364 -0.450 H1  AW8 29 
AW8 H2  H2  H  0 1 N N N 2.464  -11.790 10.164 -2.787 -2.764 -0.559 H2  AW8 30 
AW8 H3  H3  H  0 1 N N N 6.317  -13.239 7.469  -4.507 1.668  0.763  H3  AW8 31 
AW8 H4  H4  H  0 1 N N N 6.562  -11.389 9.089  -2.080 1.285  0.659  H4  AW8 32 
AW8 H5  H5  H  0 1 N N N 7.616  -9.953  13.375 0.781  -4.488 0.970  H5  AW8 33 
AW8 H6  H6  H  0 1 N N N 7.926  -8.095  14.958 3.170  -4.941 0.890  H6  AW8 34 
AW8 H7  H7  H  0 1 N N N 4.451  -6.214  13.371 3.978  -0.994 -0.488 H7  AW8 35 
AW8 H8  H8  H  0 1 N N N 1.689  -8.292  7.280  -1.345 3.512  -1.487 H8  AW8 36 
AW8 H9  H9  H  0 1 N N N 0.618  -7.158  8.170  -0.061 4.369  -0.601 H9  AW8 37 
AW8 H10 H10 H  0 1 N N N 2.135  -6.557  7.418  0.179  3.925  -2.308 H10 AW8 38 
AW8 H11 H11 H  0 1 N N N 1.857  -7.587  11.739 3.273  0.850  -0.449 H11 AW8 39 
AW8 H12 H12 H  0 1 N N N 3.072  -6.263  13.139 3.124  1.448  -2.768 H12 AW8 40 
AW8 H13 H13 H  0 1 N N N 2.316  -4.688  10.597 3.462  3.273  -0.607 H13 AW8 41 
AW8 H14 H14 H  0 1 N N N 1.814  -5.112  8.925  1.981  4.260  -0.583 H14 AW8 42 
AW8 H15 H15 H  0 1 N N N -1.093 -6.377  10.874 3.092  4.238  2.912  H15 AW8 43 
# 
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 
AW8 CL1 C16 SING N N 1  
AW8 C16 C15 DOUB Y N 2  
AW8 C16 C14 SING Y N 3  
AW8 C22 C20 SING N N 4  
AW8 C15 C13 SING Y N 5  
AW8 C14 C12 DOUB Y N 6  
AW8 C13 C11 DOUB Y N 7  
AW8 C20 N19 DOUB N N 8  
AW8 C20 N18 SING N N 9  
AW8 N19 C8  SING N N 10 
AW8 C12 C11 SING Y N 11 
AW8 C11 C10 SING N N 12 
AW8 C23 N18 SING N N 13 
AW8 C23 C24 SING N N 14 
AW8 N18 C17 SING N N 15 
AW8 C24 O26 DOUB N N 16 
AW8 C24 O25 SING N N 17 
AW8 C8  C10 DOUB Y N 18 
AW8 C8  C7  SING Y N 19 
AW8 C10 N9  SING Y N 20 
AW8 C17 C7  SING N N 21 
AW8 C17 O21 SING N N 22 
AW8 C7  C1  DOUB Y N 23 
AW8 N9  C2  DOUB Y N 24 
AW8 C2  C1  SING Y N 25 
AW8 C2  C4  SING Y N 26 
AW8 C1  C3  SING Y N 27 
AW8 C4  C6  DOUB Y N 28 
AW8 C3  C5  DOUB Y N 29 
AW8 C6  C5  SING Y N 30 
AW8 C5  F27 SING N N 31 
AW8 C14 H1  SING N N 32 
AW8 C12 H2  SING N N 33 
AW8 C15 H3  SING N N 34 
AW8 C13 H4  SING N N 35 
AW8 C4  H5  SING N N 36 
AW8 C6  H6  SING N N 37 
AW8 C3  H7  SING N N 38 
AW8 C22 H8  SING N N 39 
AW8 C22 H9  SING N N 40 
AW8 C22 H10 SING N N 41 
AW8 C17 H11 SING N N 42 
AW8 O21 H12 SING N N 43 
AW8 C23 H13 SING N N 44 
AW8 C23 H14 SING N N 45 
AW8 O25 H15 SING N N 46 
# 
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 
AW8 InChI            InChI                1.03  "InChI=1S/C20H15ClFN3O3/c1-10-23-19-17(20(28)25(10)9-16(26)27)14-8-13(22)6-7-15(14)24-18(19)11-2-4-12(21)5-3-11/h2-8,20,28H,9H2,1H3,(H,26,27)/t20-/m1/s1" 
AW8 InChIKey         InChI                1.03  WLZWRUMUOJLESO-HXUWFJFHSA-N                                                                                                                               
AW8 SMILES_CANONICAL CACTVS               3.385 "CC1=Nc2c(nc3ccc(F)cc3c2[C@@H](O)N1CC(O)=O)c4ccc(Cl)cc4"                                                                                                  
AW8 SMILES           CACTVS               3.385 "CC1=Nc2c(nc3ccc(F)cc3c2[CH](O)N1CC(O)=O)c4ccc(Cl)cc4"                                                                                                    
AW8 SMILES_CANONICAL "OpenEye OEToolkits" 2.0.6 "CC1=Nc2c(c3cc(ccc3nc2c4ccc(cc4)Cl)F)[C@H](N1CC(=O)O)O"                                                                                                   
AW8 SMILES           "OpenEye OEToolkits" 2.0.6 "CC1=Nc2c(c3cc(ccc3nc2c4ccc(cc4)Cl)F)C(N1CC(=O)O)O"                                                                                                       
# 
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 
AW8 "SYSTEMATIC NAME" "OpenEye OEToolkits" 2.0.6 "2-[(1~{R})-5-(4-chlorophenyl)-9-fluoranyl-3-methyl-1-oxidanyl-1~{H}-pyrimido[4,5-c]quinolin-2-yl]ethanoic 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 
AW8 "Create component" 2017-08-24 EBI  
AW8 "Initial release"  2018-05-09 RCSB 
# 
