data_058 # _chem_comp.id 058 _chem_comp.name "1-benzyl-5-chloro-3-(2-fluorophenyl)-1H-indole-2-carboxylic acid" _chem_comp.type NON-POLYMER _chem_comp.pdbx_type HETAIN _chem_comp.formula "C22 H15 Cl F N O2" _chem_comp.mon_nstd_parent_comp_id ? _chem_comp.pdbx_synonyms ? _chem_comp.pdbx_formal_charge 0 _chem_comp.pdbx_initial_date 2011-06-27 _chem_comp.pdbx_modified_date 2011-08-26 _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 379.811 _chem_comp.one_letter_code ? _chem_comp.three_letter_code 058 _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 3SKH _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 058 C1 C1 C 0 1 Y N N 25.336 42.983 49.190 1.235 3.329 -0.018 C1 058 1 058 F1 F1 F 0 1 N N N 21.607 45.878 45.185 3.053 -1.234 1.780 F1 058 2 058 N1 N1 N 0 1 Y N N 25.238 43.704 45.096 -1.089 0.047 0.936 N1 058 3 058 O1 O1 O 0 1 N N N 24.523 46.915 43.828 -1.767 -2.801 1.214 O1 058 4 058 CL1 CL1 CL 0 0 N N N 25.305 42.810 50.908 2.288 4.639 -0.451 CL1 058 5 058 C2 C2 C 0 1 Y N N 25.990 42.037 48.400 -0.025 3.599 0.501 C2 058 6 058 O2 O2 O 0 1 N N N 23.721 45.104 42.744 0.244 -3.257 0.385 O2 058 7 058 C3 C3 C 0 1 Y N N 26.019 42.182 47.005 -0.875 2.574 0.850 C3 058 8 058 C4 C4 C 0 1 Y N N 24.686 44.087 48.607 1.650 2.038 -0.196 C4 058 9 058 C5 C5 C 0 1 Y N N 24.507 44.885 45.005 -0.252 -0.995 0.591 C5 058 10 058 C6 C6 C 0 1 Y N N 24.163 45.230 46.319 0.928 -0.478 0.087 C6 058 11 058 C7 C7 C 0 1 Y N N 24.703 44.249 47.197 0.801 0.983 0.147 C7 058 12 058 C8 C8 C 0 1 Y N N 25.369 43.300 46.418 -0.472 1.251 0.683 C8 058 13 058 C9 C9 C 0 1 N N N 25.804 43.000 43.953 -2.436 -0.105 1.490 C9 058 14 058 C10 C10 C 0 1 N N N 24.185 45.598 43.766 -0.570 -2.419 0.721 C10 058 15 058 C11 C11 C 0 1 Y N N 23.380 46.402 46.708 2.095 -1.246 -0.400 C11 058 16 058 C12 C12 C 0 1 Y N N 23.875 47.268 47.701 2.177 -1.619 -1.743 C12 058 17 058 C13 C13 C 0 1 Y N N 23.128 48.388 48.092 3.268 -2.335 -2.191 C13 058 18 058 C14 C14 C 0 1 Y N N 21.883 48.656 47.500 4.280 -2.683 -1.314 C14 058 19 058 C15 C15 C 0 1 Y N N 21.383 47.803 46.518 4.207 -2.318 0.018 C15 058 20 058 C16 C16 C 0 1 Y N N 22.123 46.684 46.128 3.122 -1.596 0.480 C16 058 21 058 C17 C17 C 0 1 Y N N 27.105 43.631 43.530 -3.439 -0.157 0.367 C17 058 22 058 C18 C18 C 0 1 Y N N 27.801 43.136 42.415 -4.009 1.010 -0.105 C18 058 23 058 C19 C19 C 0 1 Y N N 29.010 43.724 42.015 -4.929 0.963 -1.135 C19 058 24 058 C20 C20 C 0 1 Y N N 29.543 44.805 42.730 -5.278 -0.252 -1.695 C20 058 25 058 C21 C21 C 0 1 Y N N 28.867 45.305 43.847 -4.707 -1.419 -1.224 C21 058 26 058 C22 C22 C 0 1 Y N N 27.656 44.724 44.241 -3.783 -1.371 -0.197 C22 058 27 058 HO1 HO1 H 0 1 N N N 24.341 47.329 42.993 -1.885 -3.760 1.262 HO1 058 28 058 H2 H2 H 0 1 N N N 26.475 41.191 48.864 -0.340 4.623 0.632 H2 058 29 058 H3 H3 H 0 1 N N N 26.527 41.456 46.388 -1.852 2.795 1.253 H3 058 30 058 H4 H4 H 0 1 N N N 24.177 44.808 49.230 2.631 1.835 -0.600 H4 058 31 058 H9 H9 H 0 1 N N N 25.987 41.952 44.231 -2.489 -1.028 2.068 H9 058 32 058 H9A H9A H 0 1 N N N 25.093 43.046 43.115 -2.660 0.742 2.139 H9A 058 33 058 H12 H12 H 0 1 N N N 24.831 47.069 48.162 1.389 -1.349 -2.429 H12 058 34 058 H13 H13 H 0 1 N N N 23.513 49.050 48.854 3.332 -2.624 -3.229 H13 058 35 058 H14 H14 H 0 1 N N N 21.314 49.522 47.805 5.131 -3.244 -1.671 H14 058 36 058 H15 H15 H 0 1 N N N 20.426 48.006 46.060 5.000 -2.593 0.697 H15 058 37 058 H18 H18 H 0 1 N N N 27.403 42.298 41.862 -3.737 1.960 0.332 H18 058 38 058 H19 H19 H 0 1 N N N 29.533 43.341 41.151 -5.376 1.875 -1.503 H19 058 39 058 H20 H20 H 0 1 N N N 30.476 45.252 42.418 -5.997 -0.289 -2.500 H20 058 40 058 H21 H21 H 0 1 N N N 29.277 46.135 44.403 -4.979 -2.369 -1.661 H21 058 41 058 H22 H22 H 0 1 N N N 27.134 45.116 45.101 -3.334 -2.283 0.169 H22 058 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 058 C1 C2 DOUB Y N 1 058 C4 C1 SING Y N 2 058 C1 CL1 SING N N 3 058 F1 C16 SING N N 4 058 C9 N1 SING N N 5 058 C5 N1 SING Y N 6 058 N1 C8 SING Y N 7 058 C10 O1 SING N N 8 058 O1 HO1 SING N N 9 058 C2 C3 SING Y N 10 058 C2 H2 SING N N 11 058 O2 C10 DOUB N N 12 058 C8 C3 DOUB Y N 13 058 C3 H3 SING N N 14 058 C7 C4 DOUB Y N 15 058 C4 H4 SING N N 16 058 C5 C6 DOUB Y N 17 058 C10 C5 SING N N 18 058 C6 C11 SING N N 19 058 C6 C7 SING Y N 20 058 C8 C7 SING Y N 21 058 C17 C9 SING N N 22 058 C9 H9 SING N N 23 058 C9 H9A SING N N 24 058 C16 C11 DOUB Y N 25 058 C11 C12 SING Y N 26 058 C12 C13 DOUB Y N 27 058 C12 H12 SING N N 28 058 C14 C13 SING Y N 29 058 C13 H13 SING N N 30 058 C15 C14 DOUB Y N 31 058 C14 H14 SING N N 32 058 C16 C15 SING Y N 33 058 C15 H15 SING N N 34 058 C18 C17 DOUB Y N 35 058 C17 C22 SING Y N 36 058 C19 C18 SING Y N 37 058 C18 H18 SING N N 38 058 C19 C20 DOUB Y N 39 058 C19 H19 SING N N 40 058 C20 C21 SING Y N 41 058 C20 H20 SING N N 42 058 C21 C22 DOUB Y N 43 058 C21 H21 SING N N 44 058 C22 H22 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 058 SMILES ACDLabs 12.01 "Fc4ccccc4c2c1cc(Cl)ccc1n(c2C(=O)O)Cc3ccccc3" 058 InChI InChI 1.03 "InChI=1S/C22H15ClFNO2/c23-15-10-11-19-17(12-15)20(16-8-4-5-9-18(16)24)21(22(26)27)25(19)13-14-6-2-1-3-7-14/h1-12H,13H2,(H,26,27)" 058 InChIKey InChI 1.03 IOOYKINARCKSEF-UHFFFAOYSA-N 058 SMILES_CANONICAL CACTVS 3.370 "OC(=O)c1n(Cc2ccccc2)c3ccc(Cl)cc3c1c4ccccc4F" 058 SMILES CACTVS 3.370 "OC(=O)c1n(Cc2ccccc2)c3ccc(Cl)cc3c1c4ccccc4F" 058 SMILES_CANONICAL "OpenEye OEToolkits" 1.7.2 "c1ccc(cc1)Cn2c3ccc(cc3c(c2C(=O)O)c4ccccc4F)Cl" 058 SMILES "OpenEye OEToolkits" 1.7.2 "c1ccc(cc1)Cn2c3ccc(cc3c(c2C(=O)O)c4ccccc4F)Cl" # 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 058 "SYSTEMATIC NAME" ACDLabs 12.01 "1-benzyl-5-chloro-3-(2-fluorophenyl)-1H-indole-2-carboxylic acid" 058 "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.7.2 "5-chloranyl-3-(2-fluorophenyl)-1-(phenylmethyl)indole-2-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 058 "Create component" 2011-06-27 RCSB #