data_BRE # _chem_comp.id BRE _chem_comp.name "2-BIPHENYL-4-YL-6-FLUORO-3-METHYL-QUINOLINE-4-CARBOXYLIC ACID" _chem_comp.type NON-POLYMER _chem_comp.pdbx_type HETAIN _chem_comp.formula "C23 H16 F N O2" _chem_comp.mon_nstd_parent_comp_id ? _chem_comp.pdbx_synonyms "BREQUINAR ANALOG" _chem_comp.pdbx_formal_charge 0 _chem_comp.pdbx_initial_date 1999-10-01 _chem_comp.pdbx_modified_date 2020-06-17 _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 357.377 _chem_comp.one_letter_code ? _chem_comp.three_letter_code BRE _chem_comp.pdbx_model_coordinates_details ? _chem_comp.pdbx_model_coordinates_missing_flag N _chem_comp.pdbx_ideal_coordinates_details ? _chem_comp.pdbx_ideal_coordinates_missing_flag N _chem_comp.pdbx_model_coordinates_db_code 1D3G _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 BRE C1 C1 C 0 1 N N N 50.033 43.306 -5.250 2.354 0.240 -0.513 C1 BRE 1 BRE C2 C2 C 0 1 Y N N 49.712 42.458 -4.037 1.071 0.114 -1.293 C2 BRE 2 BRE C3 C3 C 0 1 Y N N 50.234 42.754 -2.792 -0.155 -0.007 -0.622 C3 BRE 3 BRE C4 C4 C 0 1 Y N N 48.851 41.372 -4.163 1.091 0.124 -2.681 C4 BRE 4 BRE N1 N1 N 0 1 Y N N 49.967 41.949 -1.727 -1.299 -0.120 -1.264 N1 BRE 5 BRE C5 C5 C 0 1 N N N 48.299 41.031 -5.521 2.357 0.257 -3.430 C5 BRE 6 BRE C23 C23 C 0 1 Y N N 51.170 43.872 -2.483 -0.163 -0.010 0.859 C23 BRE 7 BRE C6 C6 C 0 1 Y N N 48.524 40.594 -3.052 -0.192 -0.007 -3.372 C6 BRE 8 BRE C7 C7 C 0 1 Y N N 49.113 40.919 -1.836 -1.373 -0.126 -2.596 C7 BRE 9 BRE C8 C8 C 0 1 Y N N 52.283 44.062 -3.309 -1.168 0.664 1.552 C8 BRE 10 BRE C9 C9 C 0 1 Y N N 50.984 44.641 -1.357 0.830 -0.693 1.560 C9 BRE 11 BRE O1 O1 O 0 1 N N N 47.171 41.232 -5.868 2.769 1.358 -3.736 O1 BRE 12 BRE O2 O2 O 0 1 N N N 49.169 40.460 -6.379 3.055 -0.842 -3.774 O2 BRE 13 BRE C10 C10 C 0 1 Y N N 47.599 39.556 -3.078 -0.272 -0.013 -4.767 C10 BRE 14 BRE C11 C11 C 0 1 Y N N 48.781 40.210 -0.686 -2.611 -0.247 -3.253 C11 BRE 15 BRE C12 C12 C 0 1 Y N N 53.165 45.055 -2.944 -1.175 0.661 2.929 C12 BRE 16 BRE C13 C13 C 0 1 Y N N 51.886 45.630 -1.000 0.825 -0.691 2.938 C13 BRE 17 BRE C14 C14 C 0 1 Y N N 47.269 38.855 -1.932 -1.491 -0.133 -5.372 C14 BRE 18 BRE C15 C15 C 0 1 Y N N 47.872 39.167 -0.723 -2.656 -0.249 -4.613 C15 BRE 19 BRE C16 C16 C 0 1 Y N N 52.996 45.860 -1.829 -0.178 -0.016 3.631 C16 BRE 20 BRE F1 F1 F 0 1 N N N 46.397 37.974 -1.962 -1.570 -0.139 -6.721 F1 BRE 21 BRE C17 C17 C 0 1 Y N N 54.072 46.885 -1.423 -0.187 -0.019 5.114 C17 BRE 22 BRE C18 C18 C 0 1 Y N N 54.651 46.771 -0.148 0.145 -1.178 5.813 C18 BRE 23 BRE C19 C19 C 0 1 Y N N 54.616 47.788 -2.329 -0.521 1.138 5.814 C19 BRE 24 BRE C20 C20 C 0 1 Y N N 55.678 47.613 0.247 0.136 -1.175 7.193 C20 BRE 25 BRE C21 C21 C 0 1 Y N N 56.186 48.532 -0.653 -0.202 -0.025 7.882 C21 BRE 26 BRE C22 C22 C 0 1 Y N N 55.639 48.629 -1.915 -0.533 1.128 7.194 C22 BRE 27 BRE H11 1H1 H 0 1 N N N 49.611 43.067 -6.254 2.155 0.736 0.437 H11 BRE 28 BRE H12 2H1 H 0 1 N N N 49.770 44.362 -5.009 2.765 -0.751 -0.326 H12 BRE 29 BRE H13 3H1 H 0 1 N N N 51.142 43.360 -5.346 3.071 0.829 -1.085 H13 BRE 30 BRE H81 1H8 H 0 1 N N N 52.458 43.453 -4.211 -1.939 1.190 1.009 H81 BRE 31 BRE H91 1H9 H 0 1 N N N 50.095 44.461 -0.728 1.608 -1.216 1.024 H91 BRE 32 BRE HO2 HO2 H 0 1 N N N 48.820 40.244 -7.236 3.884 -0.754 -4.264 HO2 BRE 33 BRE H101 1H10 H 0 0 N N N 47.115 39.282 -4.030 0.623 0.076 -5.364 H101 BRE 34 BRE H111 1H11 H 0 0 N N N 49.248 40.480 0.275 -3.522 -0.339 -2.681 H111 BRE 35 BRE H121 1H12 H 0 0 N N N 54.053 45.213 -3.578 -1.953 1.184 3.466 H121 BRE 36 BRE H131 1H13 H 0 0 N N N 51.724 46.218 -0.080 1.597 -1.216 3.481 H131 BRE 37 BRE H151 1H15 H 0 0 N N N 47.633 38.597 0.190 -3.609 -0.343 -5.113 H151 BRE 38 BRE H181 1H18 H 0 0 N N N 54.291 46.003 0.558 0.410 -2.077 5.276 H181 BRE 39 BRE H191 1H19 H 0 0 N N N 54.240 47.836 -3.364 -0.780 2.039 5.277 H191 BRE 40 BRE H201 1H20 H 0 0 N N N 56.087 47.552 1.269 0.393 -2.073 7.736 H201 BRE 41 BRE H211 1H21 H 0 0 N N N 57.025 49.186 -0.364 -0.208 -0.027 8.962 H211 BRE 42 BRE H221 1H22 H 0 0 N N N 56.027 49.394 -2.607 -0.796 2.023 7.737 H221 BRE 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 BRE C1 C2 SING N N 1 BRE C1 H11 SING N N 2 BRE C1 H12 SING N N 3 BRE C1 H13 SING N N 4 BRE C2 C3 SING Y N 5 BRE C2 C4 DOUB Y N 6 BRE C3 N1 DOUB Y N 7 BRE C3 C23 SING Y N 8 BRE C4 C5 SING N N 9 BRE C4 C6 SING Y N 10 BRE N1 C7 SING Y N 11 BRE C5 O1 DOUB N N 12 BRE C5 O2 SING N N 13 BRE C23 C8 DOUB Y N 14 BRE C23 C9 SING Y N 15 BRE C6 C7 DOUB Y N 16 BRE C6 C10 SING Y N 17 BRE C7 C11 SING Y N 18 BRE C8 C12 SING Y N 19 BRE C8 H81 SING N N 20 BRE C9 C13 DOUB Y N 21 BRE C9 H91 SING N N 22 BRE O2 HO2 SING N N 23 BRE C10 C14 DOUB Y N 24 BRE C10 H101 SING N N 25 BRE C11 C15 DOUB Y N 26 BRE C11 H111 SING N N 27 BRE C12 C16 DOUB Y N 28 BRE C12 H121 SING N N 29 BRE C13 C16 SING Y N 30 BRE C13 H131 SING N N 31 BRE C14 C15 SING Y N 32 BRE C14 F1 SING N N 33 BRE C15 H151 SING N N 34 BRE C16 C17 SING Y N 35 BRE C17 C18 DOUB Y N 36 BRE C17 C19 SING Y N 37 BRE C18 C20 SING Y N 38 BRE C18 H181 SING N N 39 BRE C19 C22 DOUB Y N 40 BRE C19 H191 SING N N 41 BRE C20 C21 DOUB Y N 42 BRE C20 H201 SING N N 43 BRE C21 C22 SING Y N 44 BRE C21 H211 SING N N 45 BRE C22 H221 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 BRE SMILES ACDLabs 10.04 "Fc1ccc2nc(c(c(c2c1)C(=O)O)C)c4ccc(c3ccccc3)cc4" BRE SMILES_CANONICAL CACTVS 3.341 "Cc1c(nc2ccc(F)cc2c1C(O)=O)c3ccc(cc3)c4ccccc4" BRE SMILES CACTVS 3.341 "Cc1c(nc2ccc(F)cc2c1C(O)=O)c3ccc(cc3)c4ccccc4" BRE SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 "Cc1c(c2cc(ccc2nc1c3ccc(cc3)c4ccccc4)F)C(=O)O" BRE SMILES "OpenEye OEToolkits" 1.5.0 "Cc1c(c2cc(ccc2nc1c3ccc(cc3)c4ccccc4)F)C(=O)O" BRE InChI InChI 1.03 "InChI=1S/C23H16FNO2/c1-14-21(23(26)27)19-13-18(24)11-12-20(19)25-22(14)17-9-7-16(8-10-17)15-5-3-2-4-6-15/h2-13H,1H3,(H,26,27)" BRE InChIKey InChI 1.03 WYKKHJQZENLZID-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 BRE "SYSTEMATIC NAME" ACDLabs 10.04 "2-biphenyl-4-yl-6-fluoro-3-methylquinoline-4-carboxylic acid" BRE "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "6-fluoro-3-methyl-2-(4-phenylphenyl)quinoline-4-carboxylic 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 BRE "Create component" 1999-10-01 RCSB BRE "Modify aromatic_flag" 2011-06-04 RCSB BRE "Modify descriptor" 2011-06-04 RCSB BRE "Modify synonyms" 2020-06-05 PDBE # _pdbx_chem_comp_synonyms.ordinal 1 _pdbx_chem_comp_synonyms.comp_id BRE _pdbx_chem_comp_synonyms.name "BREQUINAR ANALOG" _pdbx_chem_comp_synonyms.provenance ? _pdbx_chem_comp_synonyms.type ? ##