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 #