data_ZEN
# 
_chem_comp.id                                    ZEN 
_chem_comp.name                                  
;[4-(6-CHLORO-NAPHTHALENE-2-SULFONYL)-PIPERAZIN-1-YL]- (3,4,5,6-TETRAHYDRO-2H-[1,4']BIPYRIDINYL-4-YL)- METHANONE
;
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C25 H27 Cl N4 O3 S" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         ? 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     1999-08-24 
_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                        499.025 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     ZEN 
_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        1QL7 
_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 
ZEN N1   N1   N  0 1 Y N N 18.523 7.548  11.010 -3.342 0.815  8.774  N1   ZEN 1  
ZEN C2   C2   C  0 1 Y N N 19.126 6.332  11.081 -2.125 1.292  8.954  C2   ZEN 2  
ZEN C3   C3   C  0 1 Y N N 20.368 6.197  11.726 -1.085 0.905  8.135  C3   ZEN 3  
ZEN C5   C5   C  0 1 Y N N 20.314 8.576  12.217 -2.637 -0.477 6.946  C5   ZEN 4  
ZEN C6   C6   C  0 1 Y N N 19.080 8.657  11.557 -3.619 -0.044 7.812  C6   ZEN 5  
ZEN C4   C4   C  0 1 Y N N 20.966 7.333  12.303 -1.336 -0.002 7.105  C4   ZEN 6  
ZEN N7   N7   N  0 1 N N N 22.221 7.221  12.964 -0.315 -0.418 6.256  N7   ZEN 7  
ZEN C8   C8   C  0 1 N N N 22.703 5.901  13.396 -0.915 -1.358 5.304  C8   ZEN 8  
ZEN C9   C9   C  0 1 N N N 24.250 5.886  13.333 0.150  -1.857 4.327  C9   ZEN 9  
ZEN C11  C11  C  0 1 N N N 24.185 8.425  13.812 1.231  0.380  4.530  C11  ZEN 10 
ZEN C12  C12  C  0 1 N N N 22.652 8.288  13.879 0.108  0.762  5.496  C12  ZEN 11 
ZEN C10  C10  C  0 1 N N N 24.915 7.077  14.123 0.710  -0.667 3.541  C10  ZEN 12 
ZEN C13  C13  C  0 1 N N N 26.362 7.226  13.702 1.838  -1.132 2.657  C13  ZEN 13 
ZEN O23  O23  O  0 1 N N N 26.547 7.177  12.483 2.470  -2.125 2.952  O23  ZEN 14 
ZEN N14  N14  N  0 1 N N N 27.369 7.410  14.524 2.146  -0.445 1.539  N14  ZEN 15 
ZEN C15  C15  C  0 1 N N N 27.248 7.471  15.993 3.161  -0.951 0.606  C15  ZEN 16 
ZEN C16  C16  C  0 1 N N N 27.991 8.734  16.508 2.535  -1.054 -0.790 C16  ZEN 17 
ZEN C18  C18  C  0 1 N N N 29.330 8.840  14.479 0.849  0.723  -0.160 C18  ZEN 18 
ZEN C19  C19  C  0 1 N N N 28.722 7.529  13.977 1.471  0.824  1.232  C19  ZEN 19 
ZEN N17  N17  N  0 1 N N N 29.355 8.787  15.938 1.861  0.214  -1.097 N17  ZEN 20 
ZEN S20  S20  S  0 1 N N N 30.234 10.018 16.554 2.239  1.059  -2.470 S20  ZEN 21 
ZEN O21  O21  O  0 1 N N N 31.461 10.116 15.785 3.542  0.631  -2.840 O21  ZEN 22 
ZEN O22  O22  O  0 1 N N N 30.361 9.775  17.968 1.855  2.403  -2.215 O22  ZEN 23 
ZEN C24  C24  C  0 1 Y N N 29.352 11.523 16.346 1.168  0.491  -3.749 C24  ZEN 24 
ZEN C25  C25  C  0 1 Y N N 29.477 12.239 15.163 -0.030 1.106  -3.943 C25  ZEN 25 
ZEN C33  C33  C  0 1 Y N N 28.480 11.965 17.350 1.562  -0.580 -4.548 C33  ZEN 26 
ZEN C34  C34  C  0 1 Y N N 27.754 13.140 17.181 0.759  -1.043 -5.545 C34  ZEN 27 
ZEN C26  C26  C  0 1 Y N N 28.755 13.412 14.981 -0.886 0.656  -4.962 C26  ZEN 28 
ZEN C27  C27  C  0 1 Y N N 27.889 13.868 16.000 -0.486 -0.433 -5.774 C27  ZEN 29 
ZEN C28  C28  C  0 1 Y N N 27.165 15.034 15.817 -1.344 -0.888 -6.790 C28  ZEN 30 
ZEN C30  C30  C  0 1 Y N N 28.158 15.309 13.622 -2.935 0.803  -6.187 C30  ZEN 31 
ZEN C31  C31  C  0 1 Y N N 28.886 14.139 13.799 -2.131 1.266  -5.191 C31  ZEN 32 
ZEN C29  C29  C  0 1 Y N N 27.301 15.752 14.632 -2.541 -0.269 -6.987 C29  ZEN 33 
ZEN CL32 CL32 CL 0 0 N N N 26.382 17.189 14.405 -3.596 -0.828 -8.247 CL32 ZEN 34 
ZEN H2   H2   H  0 1 N N N 18.615 5.468  10.622 -1.940 1.994  9.754  H2   ZEN 35 
ZEN H3   H3   H  0 1 N N N 20.866 5.214  11.778 -0.091 1.298  8.288  H3   ZEN 36 
ZEN H5   H5   H  0 1 N N N 20.765 9.478  12.662 -2.871 -1.180 6.160  H5   ZEN 37 
ZEN H6   H6   H  0 1 N N N 18.536 9.612  11.466 -4.629 -0.410 7.699  H6   ZEN 38 
ZEN H82  2H8  H  0 1 N N N 22.315 5.615  14.401 -1.708 -0.855 4.750  H82  ZEN 39 
ZEN H81  1H8  H  0 1 N N N 22.245 5.069  12.811 -1.335 -2.205 5.846  H81  ZEN 40 
ZEN H92  2H9  H  0 1 N N N 24.651 4.905  13.680 -0.295 -2.572 3.636  H92  ZEN 41 
ZEN H91  1H9  H  0 1 N N N 24.603 5.864  12.275 0.955  -2.338 4.881  H91  ZEN 42 
ZEN H112 2H11 H  0 0 N N N 24.509 8.841  12.830 2.069  -0.033 5.091  H112 ZEN 43 
ZEN H111 1H11 H  0 0 N N N 24.545 9.241  14.479 1.559  1.264  3.984  H111 ZEN 44 
ZEN H122 2H12 H  0 0 N N N 22.131 9.253  13.678 -0.737 1.153  4.932  H122 ZEN 45 
ZEN H121 1H12 H  0 0 N N N 22.286 8.125  14.919 0.468  1.526  6.185  H121 ZEN 46 
ZEN H10  H10  H  0 1 N N N 24.840 6.849  15.211 -0.078 -0.231 2.928  H10  ZEN 47 
ZEN H152 2H15 H  0 0 N N N 26.187 7.433  16.334 3.497  -1.936 0.929  H152 ZEN 48 
ZEN H151 1H15 H  0 0 N N N 27.603 6.537  16.487 4.007  -0.264 0.577  H151 ZEN 49 
ZEN H162 2H16 H  0 0 N N N 27.416 9.668  16.305 1.810  -1.867 -0.806 H162 ZEN 50 
ZEN H161 1H16 H  0 0 N N N 28.001 8.787  17.621 3.315  -1.242 -1.528 H161 ZEN 51 
ZEN H182 2H18 H  0 0 N N N 30.331 9.051  14.035 0.514  1.709  -0.483 H182 ZEN 52 
ZEN H181 1H18 H  0 0 N N N 28.802 9.740  14.086 0.003  0.036  -0.135 H181 ZEN 53 
ZEN H192 2H19 H  0 0 N N N 29.358 6.643  14.210 0.691  1.011  1.970  H192 ZEN 54 
ZEN H191 1H19 H  0 0 N N N 28.744 7.443  12.865 2.197  1.637  1.249  H191 ZEN 55 
ZEN H25  H25  H  0 1 N N N 30.149 11.876 14.367 -0.321 1.936  -3.316 H25  ZEN 56 
ZEN H33  H33  H  0 1 N N N 28.364 11.383 18.280 2.518  -1.050 -4.374 H33  ZEN 57 
ZEN H34  H34  H  0 1 N N N 27.076 13.491 17.977 1.077  -1.874 -6.157 H34  ZEN 58 
ZEN H28  H28  H  0 1 N N N 26.484 15.388 16.609 -1.054 -1.720 -7.414 H28  ZEN 59 
ZEN H30  H30  H  0 1 N N N 28.259 15.882 12.685 -3.891 1.274  -6.361 H30  ZEN 60 
ZEN H31  H31  H  0 1 N N N 29.565 13.788 13.004 -2.449 2.098  -4.580 H31  ZEN 61 
# 
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 
ZEN N1  C2   DOUB Y N 1  
ZEN N1  C6   SING Y N 2  
ZEN C2  C3   SING Y N 3  
ZEN C2  H2   SING N N 4  
ZEN C3  C4   DOUB Y N 5  
ZEN C3  H3   SING N N 6  
ZEN C5  C6   DOUB Y N 7  
ZEN C5  C4   SING Y N 8  
ZEN C5  H5   SING N N 9  
ZEN C6  H6   SING N N 10 
ZEN C4  N7   SING N N 11 
ZEN N7  C8   SING N N 12 
ZEN N7  C12  SING N N 13 
ZEN C8  C9   SING N N 14 
ZEN C8  H82  SING N N 15 
ZEN C8  H81  SING N N 16 
ZEN C9  C10  SING N N 17 
ZEN C9  H92  SING N N 18 
ZEN C9  H91  SING N N 19 
ZEN C11 C12  SING N N 20 
ZEN C11 C10  SING N N 21 
ZEN C11 H112 SING N N 22 
ZEN C11 H111 SING N N 23 
ZEN C12 H122 SING N N 24 
ZEN C12 H121 SING N N 25 
ZEN C10 C13  SING N N 26 
ZEN C10 H10  SING N N 27 
ZEN C13 O23  DOUB N N 28 
ZEN C13 N14  SING N N 29 
ZEN N14 C15  SING N N 30 
ZEN N14 C19  SING N N 31 
ZEN C15 C16  SING N N 32 
ZEN C15 H152 SING N N 33 
ZEN C15 H151 SING N N 34 
ZEN C16 N17  SING N N 35 
ZEN C16 H162 SING N N 36 
ZEN C16 H161 SING N N 37 
ZEN C18 C19  SING N N 38 
ZEN C18 N17  SING N N 39 
ZEN C18 H182 SING N N 40 
ZEN C18 H181 SING N N 41 
ZEN C19 H192 SING N N 42 
ZEN C19 H191 SING N N 43 
ZEN N17 S20  SING N N 44 
ZEN S20 O21  DOUB N N 45 
ZEN S20 O22  DOUB N N 46 
ZEN S20 C24  SING N N 47 
ZEN C24 C25  DOUB Y N 48 
ZEN C24 C33  SING Y N 49 
ZEN C25 C26  SING Y N 50 
ZEN C25 H25  SING N N 51 
ZEN C33 C34  DOUB Y N 52 
ZEN C33 H33  SING N N 53 
ZEN C34 C27  SING Y N 54 
ZEN C34 H34  SING N N 55 
ZEN C26 C27  DOUB Y N 56 
ZEN C26 C31  SING Y N 57 
ZEN C27 C28  SING Y N 58 
ZEN C28 C29  DOUB Y N 59 
ZEN C28 H28  SING N N 60 
ZEN C30 C31  DOUB Y N 61 
ZEN C30 C29  SING Y N 62 
ZEN C30 H30  SING N N 63 
ZEN C31 H31  SING N N 64 
ZEN C29 CL32 SING N N 65 
# 
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 
ZEN SMILES           ACDLabs              10.04 Clc2ccc1cc(ccc1c2)S(=O)(=O)N5CCN(C(=O)C4CCN(c3ccncc3)CC4)CC5                                                                                                    
ZEN InChI            InChI                1.02b InChI=1/C25H27ClN4O3S/c26-22-3-1-21-18-24(4-2-20(21)17-22)34(32,33)30-15-13-29(14-16-30)25(31)19-7-11-28(12-8-19)23-5-9-27-10-6-23/h1-6,9-10,17-19H,7-8,11-16H2 
ZEN InChIKey         InChI                1.02b ZLAKCKVFSRSENR-UHFFFAOYAY                                                                                                                                       
ZEN SMILES_CANONICAL CACTVS               3.341 Clc1ccc2cc(ccc2c1)[S](=O)(=O)N3CCN(CC3)C(=O)C4CCN(CC4)c5ccncc5                                                                                                  
ZEN SMILES           CACTVS               3.341 Clc1ccc2cc(ccc2c1)[S](=O)(=O)N3CCN(CC3)C(=O)C4CCN(CC4)c5ccncc5                                                                                                  
ZEN SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 c1cc(cc2c1cc(cc2)Cl)S(=O)(=O)N3CCN(CC3)C(=O)C4CCN(CC4)c5ccncc5                                                                                                  
ZEN SMILES           "OpenEye OEToolkits" 1.5.0 c1cc(cc2c1cc(cc2)Cl)S(=O)(=O)N3CCN(CC3)C(=O)C4CCN(CC4)c5ccncc5                                                                                                  
# 
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 
ZEN "SYSTEMATIC NAME" ACDLabs              10.04 1-[(6-chloronaphthalen-2-yl)sulfonyl]-4-[(1-pyridin-4-ylpiperidin-4-yl)carbonyl]piperazine  
ZEN "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 [4-(6-chloronaphthalen-2-yl)sulfonylpiperazin-1-yl]-(1-pyridin-4-ylpiperidin-4-yl)methanone 
# 
