data_4EA
# 
_chem_comp.id                                    4EA 
_chem_comp.name                                  (1S)-2-(1H-INDOL-3-YL)-1-[({5-[(E)-2-PYRIDIN-4-YLVINYL]PYRIDIN-3-YL}OXY)METHYL]ETHYLAMINE 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C23 H22 N4 O" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         ? 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2005-12-23 
_chem_comp.pdbx_modified_date                    2008-10-14 
_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                        370.447 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     4EA 
_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        2F7X 
_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 
4EA C1   C1   C 0 1 N N N 7.525  9.842  1.359  4.570  0.166  0.113  C1   4EA 1  
4EA C2   C2   C 0 1 N N N 7.207  9.932  2.677  5.704  -0.437 -0.280 C2   4EA 2  
4EA C3   C3   C 0 1 Y N N 5.837  9.870  3.231  7.006  0.206  -0.028 C3   4EA 3  
4EA C4   C4   C 0 1 Y N N 4.673  9.703  2.420  8.201  -0.406 -0.430 C4   4EA 4  
4EA C7   C7   C 0 1 Y N N 5.680  9.978  4.630  7.083  1.448  0.616  C7   4EA 5  
4EA C8   C8   C 0 1 Y N N 4.386  9.918  5.171  8.323  2.010  0.837  C8   4EA 6  
4EA N1   N1   N 0 1 Y N N 3.269  9.760  4.409  9.424  1.399  0.441  N1   4EA 7  
4EA C9   C9   C 0 1 Y N N 3.418  9.654  3.059  9.396  0.232  -0.174 C9   4EA 8  
4EA C10  C10  C 0 1 Y N N 13.952 13.319 -1.294 -8.106 1.767  -0.951 C10  4EA 9  
4EA C11  C11  C 0 1 Y N N 14.848 12.212 -1.384 -8.165 1.150  0.279  C11  4EA 10 
4EA C12  C12  C 0 1 Y N N 15.189 11.506 -0.230 -7.124 0.322  0.687  C12  4EA 11 
4EA C13  C13  C 0 1 Y N N 14.667 11.855 1.042  -6.020 0.132  -0.164 C13  4EA 12 
4EA C14  C14  C 0 1 Y N N 13.743 12.988 1.147  -5.984 0.763  -1.409 C14  4EA 13 
4EA C15  C15  C 0 1 Y N N 13.399 13.711 -0.036 -7.017 1.573  -1.789 C15  4EA 14 
4EA N2   N2   N 0 1 Y N N 16.039 10.400 -0.069 -6.892 -0.417 1.825  N2   4EA 15 
4EA C16  C16  C 0 1 Y N N 16.053 10.059 1.268  -5.692 -1.066 1.721  C16  4EA 16 
4EA C17  C17  C 0 1 Y N N 15.220 10.928 1.978  -5.117 -0.779 0.542  C17  4EA 17 
4EA C18  C18  C 0 1 Y N N 11.469 10.021 -0.234 0.900  -1.734 -0.645 C18  4EA 18 
4EA N3   N3   N 0 1 Y N N 10.393 10.135 -1.068 2.038  -2.289 -1.014 N3   4EA 19 
4EA C19  C19  C 0 1 Y N N 9.141  10.073 -0.533 3.200  -1.713 -0.788 C19  4EA 20 
4EA C20  C20  C 0 1 Y N N 8.906  9.901  0.848  3.268  -0.477 -0.140 C20  4EA 21 
4EA C21  C21  C 0 1 Y N N 10.031 9.785  1.696  2.078  0.144  0.260  C21  4EA 22 
4EA C22  C22  C 0 1 Y N N 11.346 9.844  1.162  0.879  -0.506 0.004  C22  4EA 23 
4EA O1   O1   O 0 1 N N N 12.511 9.735  1.907  -0.301 0.054  0.378  O1   4EA 24 
4EA C24  C24  C 0 1 N N N 12.468 10.018 3.314  -1.333 -0.847 -0.029 C24  4EA 25 
4EA C23  C23  C 0 1 N N S 13.870 9.829  3.916  -2.696 -0.273 0.365  C23  4EA 26 
4EA C25  C25  C 0 1 N N N 14.924 10.909 3.466  -3.791 -1.292 0.043  C25  4EA 27 
4EA N4   N4   N 0 1 N N N 14.316 8.460  3.596  -2.942 0.964  -0.387 N4   4EA 28 
4EA H1   H1   H 0 1 N N N 6.722  9.721  0.647  4.613  1.121  0.615  H1   4EA 29 
4EA H2   H2   H 0 1 N N N 8.020  10.059 3.376  5.662  -1.392 -0.782 H2   4EA 30 
4EA H4   H4   H 0 1 N N N 4.753  9.617  1.346  8.186  -1.361 -0.933 H4   4EA 31 
4EA H7   H7   H 0 1 N N N 6.539  10.104 5.272  6.186  1.954  0.943  H7   4EA 32 
4EA H8   H8   H 0 1 N N N 4.271  10.001 6.242  8.394  2.965  1.337  H8   4EA 33 
4EA H9   H9   H 0 1 N N N 2.534  9.527  2.451  10.323 -0.231 -0.480 H9   4EA 34 
4EA H10  H10  H 0 1 N N N 13.689 13.867 -2.187 -8.915 2.409  -1.266 H10  4EA 35 
4EA H11  H11  H 0 1 N N N 15.260 11.922 -2.340 -9.017 1.307  0.924  H11  4EA 36 
4EA H14  H14  H 0 1 N N N 13.329 13.272 2.103  -5.140 0.616  -2.066 H14  4EA 37 
4EA H15  H15  H 0 1 N N N 12.723 14.551 0.020  -6.986 2.064  -2.751 H15  4EA 38 
4EA HN2  HN2  H 0 1 N N N 16.546 9.939  -0.797 -7.489 -0.470 2.587  HN2  4EA 39 
4EA H16  H16  H 0 1 N N N 16.620 9.247  1.699  -5.269 -1.714 2.475  H16  4EA 40 
4EA H18  H18  H 0 1 N N N 12.460 10.068 -0.662 -0.030 -2.242 -0.851 H18  4EA 41 
4EA H19  H19  H 0 1 N N N 8.292  10.159 -1.195 4.110  -2.201 -1.106 H19  4EA 42 
4EA H21  H21  H 0 1 N N N 9.890  9.650  2.758  2.093  1.100  0.764  H21  4EA 43 
4EA H241 1H24 H 0 0 N N N 11.762 9.332  3.805  -1.189 -1.810 0.462  H241 4EA 44 
4EA H242 2H24 H 0 0 N N N 12.138 11.056 3.470  -1.294 -0.981 -1.110 H242 4EA 45 
4EA H23  H23  H 0 1 N N N 13.797 9.974  5.004  -2.704 -0.057 1.434  H23  4EA 46 
4EA H251 1H25 H 0 0 N N N 14.491 11.890 3.711  -3.842 -1.442 -1.035 H251 4EA 47 
4EA H252 2H25 H 0 0 N N N 15.866 10.697 3.992  -3.561 -2.239 0.531  H252 4EA 48 
4EA HN41 1HN4 H 0 0 N N N 15.195 8.284  4.039  -2.925 0.717  -1.365 HN41 4EA 49 
4EA HN42 2HN4 H 0 0 N N N 14.417 8.365  2.606  -3.886 1.249  -0.176 HN42 4EA 50 
# 
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 
4EA C1  C2   DOUB N E 1  
4EA C1  C20  SING N N 2  
4EA C1  H1   SING N N 3  
4EA C2  C3   SING N N 4  
4EA C2  H2   SING N N 5  
4EA C3  C4   DOUB Y N 6  
4EA C3  C7   SING Y N 7  
4EA C4  C9   SING Y N 8  
4EA C4  H4   SING N N 9  
4EA C7  C8   DOUB Y N 10 
4EA C7  H7   SING N N 11 
4EA C8  N1   SING Y N 12 
4EA C8  H8   SING N N 13 
4EA N1  C9   DOUB Y N 14 
4EA C9  H9   SING N N 15 
4EA C10 C11  DOUB Y N 16 
4EA C10 C15  SING Y N 17 
4EA C10 H10  SING N N 18 
4EA C11 C12  SING Y N 19 
4EA C11 H11  SING N N 20 
4EA C12 C13  DOUB Y N 21 
4EA C12 N2   SING Y N 22 
4EA C13 C14  SING Y N 23 
4EA C13 C17  SING Y N 24 
4EA C14 C15  DOUB Y N 25 
4EA C14 H14  SING N N 26 
4EA C15 H15  SING N N 27 
4EA N2  C16  SING Y N 28 
4EA N2  HN2  SING N N 29 
4EA C16 C17  DOUB Y N 30 
4EA C16 H16  SING N N 31 
4EA C17 C25  SING N N 32 
4EA C18 N3   SING Y N 33 
4EA C18 C22  DOUB Y N 34 
4EA C18 H18  SING N N 35 
4EA N3  C19  DOUB Y N 36 
4EA C19 C20  SING Y N 37 
4EA C19 H19  SING N N 38 
4EA C20 C21  DOUB Y N 39 
4EA C21 C22  SING Y N 40 
4EA C21 H21  SING N N 41 
4EA C22 O1   SING N N 42 
4EA O1  C24  SING N N 43 
4EA C24 C23  SING N N 44 
4EA C24 H241 SING N N 45 
4EA C24 H242 SING N N 46 
4EA C23 C25  SING N N 47 
4EA C23 N4   SING N N 48 
4EA C23 H23  SING N N 49 
4EA C25 H251 SING N N 50 
4EA C25 H252 SING N N 51 
4EA N4  HN41 SING N N 52 
4EA N4  HN42 SING N N 53 
# 
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 
4EA SMILES           ACDLabs              10.04 n1ccc(cc1)\C=C\c4cc(OCC(N)Cc3c2ccccc2nc3)cnc4                                                                                                            
4EA InChI            InChI                1.02b InChI=1/C23H22N4O/c24-20(12-19-14-27-23-4-2-1-3-22(19)23)16-28-21-11-18(13-26-15-21)6-5-17-7-9-25-10-8-17/h1-11,13-15,20,27H,12,16,24H2/b6-5+/t20-/m0/s1 
4EA InChIKey         InChI                1.02b SGHXFHRRWFLILP-XJDXJNMNBF                                                                                                                                
4EA SMILES_CANONICAL CACTVS               3.341 N[C@H](COc1cncc(\C=C\c2ccncc2)c1)Cc3c[nH]c4ccccc34                                                                                                       
4EA SMILES           CACTVS               3.341 N[CH](COc1cncc(C=Cc2ccncc2)c1)Cc3c[nH]c4ccccc34                                                                                                          
4EA SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 c1ccc2c(c1)c(c[nH]2)C[C@@H](COc3cc(cnc3)\C=C\c4ccncc4)N                                                                                                  
4EA SMILES           "OpenEye OEToolkits" 1.5.0 c1ccc2c(c1)c(c[nH]2)CC(COc3cc(cnc3)C=Cc4ccncc4)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 
4EA "SYSTEMATIC NAME" ACDLabs              10.04 (2S)-1-(1H-indol-3-yl)-3-({5-[(E)-2-pyridin-4-ylethenyl]pyridin-3-yl}oxy)propan-2-amine 
4EA "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 (2S)-1-(1H-indol-3-yl)-3-[5-[(E)-2-pyridin-4-ylethenyl]pyridin-3-yl]oxy-propan-2-amine  
# 
