data_8S5 # _chem_comp.id 8S5 _chem_comp.name "(2~{S},4~{R})-~{N}1-(1-aminocarbonylindol-3-yl)-4-fluoranyl-~{N}2-[3-(trifluoromethyloxy)phenyl]pyrrolidine-1,2-dicarboxamide" _chem_comp.type NON-POLYMER _chem_comp.pdbx_type HETAIN _chem_comp.formula "C22 H19 F4 N5 O4" _chem_comp.mon_nstd_parent_comp_id ? _chem_comp.pdbx_synonyms ? _chem_comp.pdbx_formal_charge 0 _chem_comp.pdbx_initial_date 2017-03-01 _chem_comp.pdbx_modified_date 2017-06-23 _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 493.411 _chem_comp.one_letter_code ? _chem_comp.three_letter_code 8S5 _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 5NBA _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 8S5 C4 C1 C 0 1 N N R 10.812 10.371 0.595 0.441 -4.678 0.686 C4 8S5 1 8S5 C14 C2 C 0 1 Y N N 2.173 7.526 2.198 7.095 1.698 1.852 C14 8S5 2 8S5 C5 C3 C 0 1 N N N 9.396 10.108 0.413 1.155 -3.381 1.140 C5 8S5 3 8S5 C6 C4 C 0 1 N N N 8.142 8.516 1.965 1.708 -1.358 -0.241 C6 8S5 4 8S5 C11 C5 C 0 1 Y N N 4.879 7.624 1.529 4.813 0.431 0.941 C11 8S5 5 8S5 C7 C6 C 0 1 Y N N 6.196 7.335 1.127 3.603 0.015 0.218 C7 8S5 6 8S5 C8 C7 C 0 1 Y N N 6.298 5.960 0.873 3.421 0.893 -0.785 C8 8S5 7 8S5 C9 C8 C 0 1 N N N 4.751 4.004 1.056 4.530 2.877 -1.617 C9 8S5 8 8S5 C10 C9 C 0 1 Y N N 4.172 6.409 1.550 5.282 1.586 0.291 C10 8S5 9 8S5 C12 C10 C 0 1 Y N N 4.198 8.813 1.845 5.498 -0.071 2.048 C12 8S5 10 8S5 C13 C11 C 0 1 Y N N 2.846 8.746 2.159 6.625 0.561 2.493 C13 8S5 11 8S5 N1 N1 N 0 1 N N N 9.083 9.431 1.679 0.932 -2.423 0.042 N1 8S5 12 8S5 N2 N2 N 0 1 N N N 7.258 8.239 0.980 2.794 -1.096 0.513 N2 8S5 13 8S5 C3 C12 C 0 1 N N N 10.935 10.858 1.973 -0.812 -4.109 -0.032 C3 8S5 14 8S5 N3 N3 N 0 1 Y N N 5.062 5.383 1.172 4.417 1.846 -0.756 N3 8S5 15 8S5 O1 O1 O 0 1 N N N 8.205 11.202 3.665 -1.230 -0.884 0.253 O1 8S5 16 8S5 C1 C13 C 0 1 N N N 9.246 10.594 3.861 -1.312 -1.733 -0.610 C1 8S5 17 8S5 C2 C14 C 0 1 N N S 9.950 9.947 2.705 -0.276 -2.823 -0.695 C2 8S5 18 8S5 F1 F1 F 0 1 N N N 11.647 9.306 0.288 1.240 -5.407 -0.201 F1 8S5 19 8S5 N4 N4 N 0 1 N N N 5.645 3.292 0.371 3.625 3.033 -2.604 N4 8S5 20 8S5 O2 O2 O 0 1 N N N 3.722 3.545 1.493 5.448 3.665 -1.505 O2 8S5 21 8S5 C15 C15 C 0 1 Y N N 2.809 6.342 1.872 6.430 2.213 0.760 C15 8S5 22 8S5 O3 O3 O 0 1 N N N 8.032 8.014 3.108 1.428 -0.633 -1.176 O3 8S5 23 8S5 N5 N5 N 0 1 N N N 9.819 10.437 5.084 -2.330 -1.701 -1.492 N5 8S5 24 8S5 C16 C16 C 0 1 Y N N 9.412 11.022 6.323 -3.352 -0.756 -1.348 C16 8S5 25 8S5 C17 C17 C 0 1 Y N N 9.020 12.349 6.442 -3.975 -0.228 -2.471 C17 8S5 26 8S5 C18 C18 C 0 1 Y N N 8.673 12.862 7.693 -4.984 0.705 -2.329 C18 8S5 27 8S5 C19 C19 C 0 1 Y N N 8.724 12.066 8.828 -5.376 1.115 -1.069 C19 8S5 28 8S5 C20 C20 C 0 1 Y N N 9.133 10.742 8.700 -4.757 0.591 0.058 C20 8S5 29 8S5 O4 O4 O 0 1 N N N 9.242 9.938 9.869 -5.144 0.995 1.296 O4 8S5 30 8S5 C21 C21 C 0 1 N N N 8.218 9.200 10.192 -6.194 1.962 1.365 C21 8S5 31 8S5 F2 F2 F 0 1 N N N 8.505 8.647 11.369 -6.464 2.263 2.704 F2 8S5 32 8S5 F3 F3 F 0 1 N N N 7.936 8.278 9.289 -5.800 3.126 0.696 F3 8S5 33 8S5 F4 F4 F 0 1 N N N 7.121 9.902 10.312 -7.345 1.444 0.762 F4 8S5 34 8S5 C22 C22 C 0 1 Y N N 9.486 10.225 7.461 -3.748 -0.349 -0.081 C22 8S5 35 8S5 H1 H1 H 0 1 N N N 11.074 11.210 -0.067 0.157 -5.288 1.544 H1 8S5 36 8S5 H2 H2 H 0 1 N N N 1.133 7.505 2.489 7.987 2.187 2.215 H2 8S5 37 8S5 H3 H3 H 0 1 N N N 8.822 11.039 0.298 0.713 -3.008 2.064 H3 8S5 38 8S5 H4 H4 H 0 1 N N N 9.213 9.455 -0.453 2.222 -3.562 1.275 H4 8S5 39 8S5 H5 H5 H 0 1 N N N 7.174 5.441 0.512 2.613 0.860 -1.500 H5 8S5 40 8S5 H6 H6 H 0 1 N N N 4.716 9.761 1.844 5.140 -0.958 2.550 H6 8S5 41 8S5 H7 H7 H 0 1 N N N 2.307 9.656 2.377 7.155 0.172 3.350 H7 8S5 42 8S5 H8 H8 H 0 1 N N N 7.367 8.703 0.101 3.018 -1.675 1.258 H8 8S5 43 8S5 H9 H9 H 0 1 N N N 11.959 10.732 2.354 -1.175 -4.809 -0.784 H9 8S5 44 8S5 H10 H10 H 0 1 N N N 10.641 11.915 2.054 -1.595 -3.874 0.689 H10 8S5 45 8S5 H11 H11 H 0 1 N N N 10.533 9.107 3.109 -0.026 -3.020 -1.737 H11 8S5 46 8S5 H12 H12 H 0 1 N N N 5.481 2.322 0.194 2.892 2.404 -2.693 H12 8S5 47 8S5 H13 H13 H 0 1 N N N 6.479 3.728 0.034 3.706 3.774 -3.224 H13 8S5 48 8S5 H14 H14 H 0 1 N N N 2.277 5.402 1.866 6.800 3.102 0.269 H14 8S5 49 8S5 H15 H15 H 0 1 N N N 10.621 9.841 5.121 -2.355 -2.332 -2.228 H15 8S5 50 8S5 H16 H16 H 0 1 N N N 8.984 12.983 5.568 -3.670 -0.546 -3.457 H16 8S5 51 8S5 H17 H17 H 0 1 N N N 8.361 13.892 7.778 -5.467 1.115 -3.203 H17 8S5 52 8S5 H18 H18 H 0 1 N N N 8.451 12.466 9.793 -6.165 1.845 -0.960 H18 8S5 53 8S5 H19 H19 H 0 1 N N N 9.819 9.201 7.380 -3.268 -0.761 0.794 H19 8S5 54 # 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 8S5 F1 C4 SING N N 1 8S5 N4 C9 SING N N 2 8S5 C5 C4 SING N N 3 8S5 C5 N1 SING N N 4 8S5 C4 C3 SING N N 5 8S5 C8 C7 DOUB Y N 6 8S5 C8 N3 SING Y N 7 8S5 N2 C7 SING N N 8 8S5 N2 C6 SING N N 9 8S5 C9 N3 SING N N 10 8S5 C9 O2 DOUB N N 11 8S5 C7 C11 SING Y N 12 8S5 N3 C10 SING Y N 13 8S5 C11 C10 DOUB Y N 14 8S5 C11 C12 SING Y N 15 8S5 C10 C15 SING Y N 16 8S5 N1 C6 SING N N 17 8S5 N1 C2 SING N N 18 8S5 C12 C13 DOUB Y N 19 8S5 C15 C14 DOUB Y N 20 8S5 C6 O3 DOUB N N 21 8S5 C3 C2 SING N N 22 8S5 C13 C14 SING Y N 23 8S5 C2 C1 SING N N 24 8S5 O1 C1 DOUB N N 25 8S5 C1 N5 SING N N 26 8S5 N5 C16 SING N N 27 8S5 C16 C17 DOUB Y N 28 8S5 C16 C22 SING Y N 29 8S5 C17 C18 SING Y N 30 8S5 C22 C20 DOUB Y N 31 8S5 C18 C19 DOUB Y N 32 8S5 C20 C19 SING Y N 33 8S5 C20 O4 SING N N 34 8S5 F3 C21 SING N N 35 8S5 O4 C21 SING N N 36 8S5 C21 F4 SING N N 37 8S5 C21 F2 SING N N 38 8S5 C4 H1 SING N N 39 8S5 C14 H2 SING N N 40 8S5 C5 H3 SING N N 41 8S5 C5 H4 SING N N 42 8S5 C8 H5 SING N N 43 8S5 C12 H6 SING N N 44 8S5 C13 H7 SING N N 45 8S5 N2 H8 SING N N 46 8S5 C3 H9 SING N N 47 8S5 C3 H10 SING N N 48 8S5 C2 H11 SING N N 49 8S5 N4 H12 SING N N 50 8S5 N4 H13 SING N N 51 8S5 C15 H14 SING N N 52 8S5 N5 H15 SING N N 53 8S5 C17 H16 SING N N 54 8S5 C18 H17 SING N N 55 8S5 C19 H18 SING N N 56 8S5 C22 H19 SING N N 57 # 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 8S5 InChI InChI 1.03 "InChI=1S/C22H19F4N5O4/c23-12-8-18(19(32)28-13-4-3-5-14(9-13)35-22(24,25)26)31(10-12)21(34)29-16-11-30(20(27)33)17-7-2-1-6-15(16)17/h1-7,9,11-12,18H,8,10H2,(H2,27,33)(H,28,32)(H,29,34)/t12-,18+/m1/s1" 8S5 InChIKey InChI 1.03 PFNAXJGGZUYQGP-XIKOKIGWSA-N 8S5 SMILES_CANONICAL CACTVS 3.385 "NC(=O)n1cc(NC(=O)N2C[C@H](F)C[C@H]2C(=O)Nc3cccc(OC(F)(F)F)c3)c4ccccc14" 8S5 SMILES CACTVS 3.385 "NC(=O)n1cc(NC(=O)N2C[CH](F)C[CH]2C(=O)Nc3cccc(OC(F)(F)F)c3)c4ccccc14" 8S5 SMILES_CANONICAL "OpenEye OEToolkits" 2.0.6 "c1ccc2c(c1)c(cn2C(=O)N)NC(=O)N3C[C@@H](C[C@H]3C(=O)Nc4cccc(c4)OC(F)(F)F)F" 8S5 SMILES "OpenEye OEToolkits" 2.0.6 "c1ccc2c(c1)c(cn2C(=O)N)NC(=O)N3CC(CC3C(=O)Nc4cccc(c4)OC(F)(F)F)F" # 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 8S5 "SYSTEMATIC NAME" "OpenEye OEToolkits" 2.0.6 "(2~{S},4~{R})-~{N}1-(1-aminocarbonylindol-3-yl)-4-fluoranyl-~{N}2-[3-(trifluoromethyloxy)phenyl]pyrrolidine-1,2-dicarboxamide" # loop_ _pdbx_chem_comp_audit.comp_id _pdbx_chem_comp_audit.action_type _pdbx_chem_comp_audit.date _pdbx_chem_comp_audit.processing_site 8S5 "Create component" 2017-03-01 EBI 8S5 "Initial release" 2017-06-28 RCSB #