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 
# 
