data_GKK # _chem_comp.id GKK _chem_comp.name "2-chloro-4-{[(3S)-1-methylpyrrolidin-3-yl][2-(trifluoromethyl)benzyl]amino}benzonitrile" _chem_comp.type NON-POLYMER _chem_comp.pdbx_type HETAIN _chem_comp.formula "C20 H19 Cl F3 N3" _chem_comp.mon_nstd_parent_comp_id ? _chem_comp.pdbx_synonyms ? _chem_comp.pdbx_formal_charge 0 _chem_comp.pdbx_initial_date 2009-02-26 _chem_comp.pdbx_modified_date 2011-06-04 _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 393.833 _chem_comp.one_letter_code ? _chem_comp.three_letter_code GKK _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 3G8N _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 GKK CL1 CL1 CL 0 0 N N N 14.339 16.515 5.917 4.731 -0.571 0.412 CL1 GKK 1 GKK C1 C1 C 0 1 N N N 7.289 14.440 11.943 3.303 4.059 -0.797 C1 GKK 2 GKK C2 C2 C 0 1 N N N 7.674 13.693 9.684 2.032 3.239 1.111 C2 GKK 3 GKK C3 C3 C 0 1 N N N 8.190 14.349 8.450 0.880 2.220 1.296 C3 GKK 4 GKK C4 C4 C 0 1 N N S 8.779 15.665 8.821 0.252 2.147 -0.115 C4 GKK 5 GKK C5 C5 C 0 1 N N N 8.368 15.824 10.257 1.358 2.629 -1.072 C5 GKK 6 GKK C9 C9 C 0 1 Y N N 12.028 18.229 11.536 -2.214 -0.585 2.795 C9 GKK 7 GKK C10 C10 C 0 1 Y N N 12.602 17.736 12.666 -3.556 -0.913 2.730 C10 GKK 8 GKK C8 C8 C 0 1 Y N N 11.544 17.393 10.583 -1.555 -0.144 1.663 C8 GKK 9 GKK C7 C7 C 0 1 Y N N 11.642 16.045 10.755 -2.237 -0.031 0.466 C7 GKK 10 GKK C6 C6 C 0 1 N N N 11.092 15.140 9.695 -1.518 0.451 -0.768 C6 GKK 11 GKK N1 N1 N 0 1 N N N 8.148 14.485 10.772 2.549 2.925 -0.245 N1 GKK 12 GKK C12 C12 C 0 1 Y N N 12.218 15.569 11.902 -3.578 -0.359 0.401 C12 GKK 13 GKK C13 C13 C 0 1 N N N 12.322 14.152 12.177 -4.321 -0.236 -0.905 C13 GKK 14 GKK C14 C14 C 0 1 Y N N 10.774 16.061 7.483 0.831 -0.241 -0.411 C14 GKK 15 GKK C15 C15 C 0 1 Y N N 10.034 16.486 6.426 0.475 -1.544 -0.748 C15 GKK 16 GKK N2 N2 N 0 1 N N N 10.211 15.639 8.680 -0.128 0.768 -0.431 N2 GKK 17 GKK C16 C16 C 0 1 Y N N 10.580 16.926 5.245 1.419 -2.545 -0.729 C16 GKK 18 GKK C17 C17 C 0 1 Y N N 11.937 16.928 5.094 2.739 -2.252 -0.371 C17 GKK 19 GKK C18 C18 C 0 1 N N N 12.618 17.343 3.921 3.724 -3.290 -0.351 C18 GKK 20 GKK N3 N3 N 0 1 N N N 13.172 17.681 2.966 4.506 -4.114 -0.335 N3 GKK 21 GKK C19 C19 C 0 1 Y N N 12.679 16.519 6.141 3.094 -0.941 -0.034 C19 GKK 22 GKK C20 C20 C 0 1 Y N N 12.121 16.094 7.307 2.141 0.054 -0.050 C20 GKK 23 GKK C11 C11 C 0 1 Y N N 12.697 16.400 12.853 -4.236 -0.806 1.531 C11 GKK 24 GKK F1 F1 F 0 1 N N N 12.972 13.418 11.356 -4.343 1.105 -1.304 F1 GKK 25 GKK F2 F2 F 0 1 N N N 12.951 13.977 13.255 -3.678 -1.003 -1.882 F2 GKK 26 GKK F3 F3 F 0 1 N N N 11.198 13.527 12.320 -5.633 -0.695 -0.740 F3 GKK 27 GKK H1 H1 H 0 1 N N N 7.908 14.429 12.852 4.146 4.286 -0.144 H1 GKK 28 GKK H1A H1A H 0 1 N N N 6.638 15.326 11.954 3.672 3.801 -1.790 H1A GKK 29 GKK H1B H1B H 0 1 N N N 6.671 13.531 11.909 2.651 4.930 -0.866 H1B GKK 30 GKK H2 H2 H 0 1 N N N 6.575 13.660 9.677 1.652 4.260 1.151 H2 GKK 31 GKK H2A H2A H 0 1 N N N 8.020 12.652 9.762 2.807 3.089 1.862 H2A GKK 32 GKK H3 H3 H 0 1 N N N 8.960 13.715 7.986 1.270 1.247 1.596 H3 GKK 33 GKK H3A H3A H 0 1 N N N 7.370 14.495 7.732 0.154 2.586 2.023 H3A GKK 34 GKK H4 H4 H 0 1 N N N 8.439 16.496 8.186 -0.615 2.803 -0.177 H4 GKK 35 GKK H5 H5 H 0 1 N N N 9.158 16.332 10.830 1.592 1.846 -1.793 H5 GKK 36 GKK H5A H5A H 0 1 N N N 7.459 16.437 10.344 1.033 3.530 -1.591 H5A GKK 37 GKK H9 H9 H 0 1 N N N 11.957 19.297 11.396 -1.683 -0.669 3.731 H9 GKK 38 GKK H10 H10 H 0 1 N N N 12.983 18.413 13.416 -4.072 -1.254 3.615 H10 GKK 39 GKK H8 H8 H 0 1 N N N 11.083 17.794 9.692 -0.507 0.113 1.714 H8 GKK 40 GKK H6 H6 H 0 1 N N N 11.966 14.739 9.161 -1.539 -0.330 -1.528 H6 GKK 41 GKK H6A H6A H 0 1 N N N 10.450 14.451 10.264 -2.012 1.344 -1.151 H6A GKK 42 GKK H15 H15 H 0 1 N N N 8.958 16.477 6.519 -0.545 -1.770 -1.024 H15 GKK 43 GKK H16 H16 H 0 1 N N N 9.942 17.267 4.443 1.142 -3.555 -0.990 H16 GKK 44 GKK H20 H20 H 0 1 N N N 12.765 15.775 8.113 2.413 1.066 0.215 H20 GKK 45 GKK H11 H11 H 0 1 N N N 13.149 16.003 13.750 -5.284 -1.062 1.480 H11 GKK 46 # 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 GKK CL1 C19 SING N N 1 GKK N1 C1 SING N N 2 GKK C1 H1 SING N N 3 GKK C1 H1A SING N N 4 GKK C1 H1B SING N N 5 GKK C3 C2 SING N N 6 GKK C2 N1 SING N N 7 GKK C2 H2 SING N N 8 GKK C2 H2A SING N N 9 GKK C3 C4 SING N N 10 GKK C3 H3 SING N N 11 GKK C3 H3A SING N N 12 GKK N2 C4 SING N N 13 GKK C4 C5 SING N N 14 GKK C4 H4 SING N N 15 GKK C5 N1 SING N N 16 GKK C5 H5 SING N N 17 GKK C5 H5A SING N N 18 GKK C8 C9 DOUB Y N 19 GKK C9 C10 SING Y N 20 GKK C9 H9 SING N N 21 GKK C10 C11 DOUB Y N 22 GKK C10 H10 SING N N 23 GKK C8 C7 SING Y N 24 GKK C8 H8 SING N N 25 GKK C6 C7 SING N N 26 GKK C7 C12 DOUB Y N 27 GKK N2 C6 SING N N 28 GKK C6 H6 SING N N 29 GKK C6 H6A SING N N 30 GKK C12 C13 SING N N 31 GKK C12 C11 SING Y N 32 GKK F1 C13 SING N N 33 GKK C13 F3 SING N N 34 GKK C13 F2 SING N N 35 GKK C15 C14 DOUB Y N 36 GKK C20 C14 SING Y N 37 GKK C14 N2 SING N N 38 GKK C16 C15 SING Y N 39 GKK C15 H15 SING N N 40 GKK C17 C16 DOUB Y N 41 GKK C16 H16 SING N N 42 GKK C18 C17 SING N N 43 GKK C17 C19 SING Y N 44 GKK N3 C18 TRIP N N 45 GKK C19 C20 DOUB Y N 46 GKK C20 H20 SING N N 47 GKK C11 H11 SING N N 48 # 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 GKK SMILES ACDLabs 10.04 "FC(F)(F)c1c(cccc1)CN(c2ccc(C#N)c(Cl)c2)C3CCN(C)C3" GKK SMILES_CANONICAL CACTVS 3.341 "CN1CC[C@@H](C1)N(Cc2ccccc2C(F)(F)F)c3ccc(C#N)c(Cl)c3" GKK SMILES CACTVS 3.341 "CN1CC[CH](C1)N(Cc2ccccc2C(F)(F)F)c3ccc(C#N)c(Cl)c3" GKK SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 "C[N@]1CC[C@@H](C1)N(Cc2ccccc2C(F)(F)F)c3ccc(c(c3)Cl)C#N" GKK SMILES "OpenEye OEToolkits" 1.5.0 "CN1CCC(C1)N(Cc2ccccc2C(F)(F)F)c3ccc(c(c3)Cl)C#N" GKK InChI InChI 1.03 "InChI=1S/C20H19ClF3N3/c1-26-9-8-17(13-26)27(16-7-6-14(11-25)19(21)10-16)12-15-4-2-3-5-18(15)20(22,23)24/h2-7,10,17H,8-9,12-13H2,1H3/t17-/m0/s1" GKK InChIKey InChI 1.03 HMOAZJHSXXENHE-KRWDZBQOSA-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 GKK "SYSTEMATIC NAME" ACDLabs 10.04 "2-chloro-4-{[(3S)-1-methylpyrrolidin-3-yl][2-(trifluoromethyl)benzyl]amino}benzonitrile" GKK "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "2-chloro-4-[[(1S,3S)-1-methylpyrrolidin-3-yl]-[[2-(trifluoromethyl)phenyl]methyl]amino]benzonitrile" # loop_ _pdbx_chem_comp_audit.comp_id _pdbx_chem_comp_audit.action_type _pdbx_chem_comp_audit.date _pdbx_chem_comp_audit.processing_site GKK "Create component" 2009-02-26 RCSB GKK "Modify aromatic_flag" 2011-06-04 RCSB GKK "Modify descriptor" 2011-06-04 RCSB #