data_ZYE
# 
_chem_comp.id                                    ZYE 
_chem_comp.name                                  "N-{(1S,2R)-1-BENZYL-2-HYDROXY-3-[(3-METHOXYBENZYL)AMINO]PROPYL}-1-ETHYL-4-(2-OXOPYRROLIDIN-1-YL)-1H-INDOLE-6-CARBOXAMIDE" 
_chem_comp.type                                  non-polymer 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C33 H38 N4 O4" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         ? 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2009-04-02 
_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                        554.679 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     ZYE 
_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        2WEZ 
_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 
ZYE C1   C1   C 0 1 Y N N 30.198 -2.349 35.396 3.488   -2.273 -0.435 C1   ZYE 1  
ZYE C2   C2   C 0 1 Y N N 30.015 -1.155 34.639 2.376   -1.448 -0.342 C2   ZYE 2  
ZYE C3   C3   C 0 1 Y N N 30.494 0.128  35.171 2.510   -0.155 0.159  C3   ZYE 3  
ZYE C4   C4   C 0 1 Y N N 31.131 0.151  36.447 3.763   0.320  0.571  C4   ZYE 4  
ZYE C5   C5   C 0 1 Y N N 31.318 -1.059 37.218 4.874   -0.491 0.482  C5   ZYE 5  
ZYE C6   C6   C 0 1 Y N N 30.828 -2.372 36.671 4.746   -1.795 -0.022 C6   ZYE 6  
ZYE C7   C7   C 0 1 N N N 30.313 1.355  34.374 1.325   0.720  0.257  C7   ZYE 7  
ZYE N8   N8   N 0 1 N N N 29.133 1.449  33.696 0.119   0.267  -0.138 N8   ZYE 8  
ZYE O9   O9   O 0 1 N N N 31.295 2.126  34.229 1.438   1.849  0.693  O9   ZYE 9  
ZYE C10  C10  C 0 1 N N S 28.846 2.447  32.637 -1.057  1.135  -0.041 C10  ZYE 10 
ZYE C11  C11  C 0 1 N N N 28.131 1.676  31.502 -1.144  2.018  -1.288 C11  ZYE 11 
ZYE C12  C12  C 0 1 N N R 27.993 3.692  33.070 -2.319  0.276  0.064  C12  ZYE 12 
ZYE O13  O13  O 0 1 N N N 27.743 4.603  32.005 -2.493  -0.464 -1.147 O13  ZYE 13 
ZYE C14  C14  C 0 1 Y N N 28.945 0.424  31.142 0.039   2.951  -1.326 C14  ZYE 14 
ZYE C15  C15  C 0 1 N N N 28.694 4.470  34.197 -3.533  1.178  0.290  C15  ZYE 15 
ZYE N16  N16  N 0 1 N N N 27.974 5.670  34.673 -4.725  0.348  0.510  N16  ZYE 16 
ZYE C17  C17  C 0 1 N N N 28.660 6.871  35.301 -5.914  1.183  0.731  C17  ZYE 17 
ZYE C18  C18  C 0 1 Y N N 28.131 -0.799 31.000 1.204   2.565  -1.962 C18  ZYE 18 
ZYE C19  C19  C 0 1 Y N N 28.761 -2.099 30.679 2.289   3.421  -1.997 C19  ZYE 19 
ZYE C20  C20  C 0 1 Y N N 30.226 -2.192 30.500 2.209   4.663  -1.395 C20  ZYE 20 
ZYE C21  C21  C 0 1 Y N N 31.073 -0.971 30.637 1.043   5.049  -0.760 C21  ZYE 21 
ZYE C22  C22  C 0 1 Y N N 30.452 0.332  30.954 -0.043  4.195  -0.729 C22  ZYE 22 
ZYE N23  N23  N 0 1 Y N N 29.828 -3.658 35.092 3.671   -3.564 -0.882 N23  ZYE 23 
ZYE C24  C24  C 0 1 N N N 33.671 -0.660 40.075 8.433   0.617  0.749  C24  ZYE 24 
ZYE C25  C25  C 0 1 N N N 32.352 -1.034 40.785 7.988   0.480  2.224  C25  ZYE 25 
ZYE C26  C26  C 0 1 N N N 31.326 -1.214 39.678 6.609   -0.136 2.140  C26  ZYE 26 
ZYE N27  N27  N 0 1 N N N 31.973 -0.977 38.501 6.124   -0.016 0.892  N27  ZYE 27 
ZYE C28  C28  C 0 1 N N N 33.381 -0.636 38.591 7.075   0.678  0.015  C28  ZYE 28 
ZYE O29  O29  O 0 1 N N N 30.113 -1.524 39.794 6.025   -0.662 3.064  O29  ZYE 29 
ZYE C30  C30  C 0 1 Y N N 30.233 -4.440 36.154 4.986   -3.915 -0.760 C30  ZYE 30 
ZYE C31  C31  C 0 1 Y N N 30.863 -3.687 37.167 5.689   -2.890 -0.247 C31  ZYE 31 
ZYE C32  C32  C 0 1 N N N 27.615 -3.876 33.908 2.416   -4.146 -2.898 C32  ZYE 32 
ZYE C33  C33  C 0 1 N N N 29.134 -4.095 33.853 2.614   -4.430 -1.408 C33  ZYE 33 
ZYE C34  C34  C 0 1 Y N N 30.668 8.408  32.295 -8.987  -0.918 0.082  C34  ZYE 34 
ZYE C35  C35  C 0 1 Y N N 32.023 8.258  32.808 -9.318  -1.325 1.367  C35  ZYE 35 
ZYE C36  C36  C 0 1 Y N N 32.267 7.675  34.092 -8.547  -0.919 2.438  C36  ZYE 36 
ZYE C37  C37  C 0 1 Y N N 31.171 7.226  34.901 -7.446  -0.108 2.232  C37  ZYE 37 
ZYE C38  C38  C 0 1 Y N N 29.811 7.356  34.428 -7.114  0.299  0.953  C38  ZYE 38 
ZYE C39  C39  C 0 1 Y N N 29.567 7.945  33.134 -7.882  -0.105 -0.123 C39  ZYE 39 
ZYE O40  O40  O 0 1 N N N 30.339 8.978  31.032 -9.740  -1.321 -0.975 O40  ZYE 40 
ZYE C41  C41  C 0 1 N N N 28.990 9.108  30.570 -10.860 -2.163 -0.690 C41  ZYE 41 
ZYE H2   H2   H 0 1 N N N 29.526 -1.193 33.677 1.408   -1.808 -0.657 H2   ZYE 42 
ZYE H4   H4   H 0 1 N N N 31.481 1.091  36.846 3.858   1.324  0.957  H4   ZYE 43 
ZYE H31  H31  H 0 1 N N N 31.275 -4.038 38.102 6.749   -2.877 -0.043 H31  ZYE 44 
ZYE H8   H8   H 0 1 N N N 28.410 0.799  33.930 0.029   -0.634 -0.486 H8   ZYE 45 
ZYE H10  H10  H 0 1 N N N 29.805 2.894  32.334 -0.972  1.765  0.845  H10  ZYE 46 
ZYE H111 H111 H 0 0 N N N 27.127 1.377  31.838 -1.140  1.390  -2.179 H111 ZYE 47 
ZYE H112 H112 H 0 0 N N N 28.044 2.324  30.617 -2.065  2.600  -1.258 H112 ZYE 48 
ZYE H12  H12  H 0 1 N N N 27.031 3.280  33.410 -2.219  -0.416 0.901  H12  ZYE 49 
ZYE H13  H13  H 0 1 N N N 27.687 5.486  32.350 -2.589  0.089  -1.934 H13  ZYE 50 
ZYE H151 H151 H 0 0 N N N 28.807 3.788  35.053 -3.361  1.806  1.164  H151 ZYE 51 
ZYE H152 H152 H 0 0 N N N 29.648 4.826  33.780 -3.686  1.808  -0.586 H152 ZYE 52 
ZYE H18  H18  H 0 1 N N N 27.061 -0.744 31.132 1.266   1.595  -2.432 H18  ZYE 53 
ZYE H22  H22  H 0 1 N N N 31.065 1.215  31.052 -0.954  4.498  -0.235 H22  ZYE 54 
ZYE H16  H16  H 0 1 N N N 27.510 6.031  33.864 -4.869  -0.289 -0.259 H16  ZYE 55 
ZYE H171 H171 H 0 0 N N N 27.928 7.684  35.413 -5.759  1.811  1.609  H171 ZYE 56 
ZYE H172 H172 H 0 0 N N N 29.061 6.575  36.282 -6.083  1.813  -0.142 H172 ZYE 57 
ZYE H19  H19  H 0 1 N N N 28.149 -2.983 30.575 3.199   3.119  -2.494 H19  ZYE 58 
ZYE H20  H20  H 0 1 N N N 30.683 -3.143 30.270 3.056   5.332  -1.422 H20  ZYE 59 
ZYE H21  H21  H 0 1 N N N 32.143 -1.040 30.504 0.981   6.019  -0.289 H21  ZYE 60 
ZYE H30  H30  H 0 1 N N N 30.084 -5.509 36.204 5.400   -4.873 -1.037 H30  ZYE 61 
ZYE H331 H331 H 0 0 N N N 29.536 -3.516 33.009 2.897   -5.474 -1.272 H331 ZYE 62 
ZYE H332 H332 H 0 0 N N N 29.309 -5.175 33.738 1.684   -4.234 -0.874 H332 ZYE 63 
ZYE H251 H251 H 0 0 N N N 32.470 -1.963 41.362 8.667   -0.177 2.768  H251 ZYE 64 
ZYE H252 H252 H 0 0 N N N 32.043 -0.257 41.500 7.940   1.459  2.700  H252 ZYE 65 
ZYE H321 H321 H 0 0 N N N 27.289 -3.824 34.957 2.132   -3.102 -3.035 H321 ZYE 66 
ZYE H322 H322 H 0 0 N N N 27.362 -2.935 33.398 3.346   -4.342 -3.432 H322 ZYE 67 
ZYE H323 H323 H 0 0 N N N 27.106 -4.713 33.408 1.629   -4.791 -3.290 H323 ZYE 68 
ZYE H35  H35  H 0 1 N N N 32.857 8.592  32.209 -10.177 -1.958 1.528  H35  ZYE 69 
ZYE H39  H39  H 0 1 N N N 28.552 8.045  32.780 -7.622  0.213  -1.122 H39  ZYE 70 
ZYE H36  H36  H 0 1 N N N 33.280 7.573  34.453 -8.804  -1.235 3.438  H36  ZYE 71 
ZYE H37  H37  H 0 1 N N N 31.363 6.788  35.869 -6.845  0.209  3.071  H37  ZYE 72 
ZYE H411 H411 H 0 0 N N N 28.308 9.141  31.432 -10.513 -3.079 -0.212 H411 ZYE 73 
ZYE H412 H412 H 0 0 N N N 28.890 10.036 29.988 -11.546 -1.641 -0.023 H412 ZYE 74 
ZYE H413 H413 H 0 0 N N N 28.736 8.247  29.935 -11.374 -2.410 -1.619 H413 ZYE 75 
ZYE H241 H241 H 0 0 N N N 34.020 0.327  40.412 9.001   1.534  0.597  H241 ZYE 76 
ZYE H242 H242 H 0 0 N N N 34.462 -1.388 40.308 9.008   -0.254 0.433  H242 ZYE 77 
ZYE H281 H281 H 0 0 N N N 33.580 0.357  38.161 6.770   1.714  -0.127 H281 ZYE 78 
ZYE H282 H282 H 0 0 N N N 34.019 -1.332 38.027 7.142   0.168  -0.946 H282 ZYE 79 
# 
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 
ZYE C1  C2   SING Y N 1  
ZYE C1  C6   DOUB Y N 2  
ZYE C1  N23  SING Y N 3  
ZYE C2  C3   DOUB Y N 4  
ZYE C3  C4   SING Y N 5  
ZYE C3  C7   SING N N 6  
ZYE C4  C5   DOUB Y N 7  
ZYE C5  C6   SING Y N 8  
ZYE C5  N27  SING N N 9  
ZYE C6  C31  SING Y N 10 
ZYE C7  N8   SING N N 11 
ZYE C7  O9   DOUB N N 12 
ZYE N8  C10  SING N N 13 
ZYE C10 C11  SING N N 14 
ZYE C10 C12  SING N N 15 
ZYE C11 C14  SING N N 16 
ZYE C12 O13  SING N N 17 
ZYE C12 C15  SING N N 18 
ZYE C14 C18  SING Y N 19 
ZYE C14 C22  DOUB Y N 20 
ZYE C15 N16  SING N N 21 
ZYE N16 C17  SING N N 22 
ZYE C17 C38  SING N N 23 
ZYE C18 C19  DOUB Y N 24 
ZYE C19 C20  SING Y N 25 
ZYE C20 C21  DOUB Y N 26 
ZYE C21 C22  SING Y N 27 
ZYE N23 C30  SING Y N 28 
ZYE N23 C33  SING N N 29 
ZYE C24 C25  SING N N 30 
ZYE C24 C28  SING N N 31 
ZYE C25 C26  SING N N 32 
ZYE C26 N27  SING N N 33 
ZYE C26 O29  DOUB N N 34 
ZYE N27 C28  SING N N 35 
ZYE C30 C31  DOUB Y N 36 
ZYE C32 C33  SING N N 37 
ZYE C34 C35  SING Y N 38 
ZYE C34 C39  DOUB Y N 39 
ZYE C34 O40  SING N N 40 
ZYE C35 C36  DOUB Y N 41 
ZYE C36 C37  SING Y N 42 
ZYE C37 C38  DOUB Y N 43 
ZYE C38 C39  SING Y N 44 
ZYE O40 C41  SING N N 45 
ZYE C2  H2   SING N N 46 
ZYE C4  H4   SING N N 47 
ZYE C31 H31  SING N N 48 
ZYE N8  H8   SING N N 49 
ZYE C10 H10  SING N N 50 
ZYE C11 H111 SING N N 51 
ZYE C11 H112 SING N N 52 
ZYE C12 H12  SING N N 53 
ZYE O13 H13  SING N N 54 
ZYE C15 H151 SING N N 55 
ZYE C15 H152 SING N N 56 
ZYE C18 H18  SING N N 57 
ZYE C22 H22  SING N N 58 
ZYE N16 H16  SING N N 59 
ZYE C17 H171 SING N N 60 
ZYE C17 H172 SING N N 61 
ZYE C19 H19  SING N N 62 
ZYE C20 H20  SING N N 63 
ZYE C21 H21  SING N N 64 
ZYE C30 H30  SING N N 65 
ZYE C33 H331 SING N N 66 
ZYE C33 H332 SING N N 67 
ZYE C25 H251 SING N N 68 
ZYE C25 H252 SING N N 69 
ZYE C32 H321 SING N N 70 
ZYE C32 H322 SING N N 71 
ZYE C32 H323 SING N N 72 
ZYE C35 H35  SING N N 73 
ZYE C39 H39  SING N N 74 
ZYE C36 H36  SING N N 75 
ZYE C37 H37  SING N N 76 
ZYE C41 H411 SING N N 77 
ZYE C41 H412 SING N N 78 
ZYE C41 H413 SING N N 79 
ZYE C24 H241 SING N N 80 
ZYE C24 H242 SING N N 81 
ZYE C28 H281 SING N N 82 
ZYE C28 H282 SING N N 83 
# 
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 
ZYE SMILES           ACDLabs              10.04 "O=C5N(c1cc(cc2c1ccn2CC)C(=O)NC(Cc3ccccc3)C(O)CNCc4cccc(OC)c4)CCC5" 
ZYE SMILES_CANONICAL CACTVS               3.352 "CCn1ccc2c1cc(cc2N3CCCC3=O)C(=O)N[C@@H](Cc4ccccc4)[C@H](O)CNCc5cccc(OC)c5" 
ZYE SMILES           CACTVS               3.352 "CCn1ccc2c1cc(cc2N3CCCC3=O)C(=O)N[CH](Cc4ccccc4)[CH](O)CNCc5cccc(OC)c5" 
ZYE SMILES_CANONICAL "OpenEye OEToolkits" 1.6.1 "CCn1ccc2c1cc(cc2N3CCCC3=O)C(=O)N[C@@H](Cc4ccccc4)[C@@H](CNCc5cccc(c5)OC)O" 
ZYE SMILES           "OpenEye OEToolkits" 1.6.1 "CCn1ccc2c1cc(cc2N3CCCC3=O)C(=O)NC(Cc4ccccc4)C(CNCc5cccc(c5)OC)O" 
ZYE InChI            InChI                1.03  
"InChI=1S/C33H38N4O4/c1-3-36-16-14-27-29(36)19-25(20-30(27)37-15-8-13-32(37)39)33(40)35-28(18-23-9-5-4-6-10-23)31(38)22-34-21-24-11-7-12-26(17-24)41-2/h4-7,9-12,14,16-17,19-20,28,31,34,38H,3,8,13,15,18,21-22H2,1-2H3,(H,35,40)/t28-,31+/m0/s1" 
ZYE InChIKey         InChI                1.03  BARAICYUEPEIRD-QCENPCRXSA-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 
ZYE "SYSTEMATIC NAME" ACDLabs              10.04 "N-{(1S,2R)-1-benzyl-2-hydroxy-3-[(3-methoxybenzyl)amino]propyl}-1-ethyl-4-(2-oxopyrrolidin-1-yl)-1H-indole-6-carboxamide"        
ZYE "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.6.1 "1-ethyl-N-[(2S,3R)-3-hydroxy-4-[(3-methoxyphenyl)methylamino]-1-phenyl-butan-2-yl]-4-(2-oxopyrrolidin-1-yl)indole-6-carboxamide" 
# 
loop_
_pdbx_chem_comp_audit.comp_id 
_pdbx_chem_comp_audit.action_type 
_pdbx_chem_comp_audit.date 
_pdbx_chem_comp_audit.processing_site 
ZYE "Create component"     2009-04-02 EBI  
ZYE "Modify aromatic_flag" 2011-06-04 RCSB 
ZYE "Modify descriptor"    2011-06-04 RCSB 
# 
