data_XMH
# 
_chem_comp.id                                    XMH 
_chem_comp.name                                  "4-[(6-CHLORO-2-NAPHTHALENYL)SULFONYL]-1-[[1-(4-PYRIDINYL)-4-PIPERIDINYL]METHYL]-2-PIPERAZINECARBOXYLIC ACID ETHYL ESTER" 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C28 H33 Cl N4 O4 S" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         ? 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2001-07-25 
_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                        557.104 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     XMH 
_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        1IQJ 
_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 
XMH C1   C1   C  0 1 N N N 4.380  20.046 4.513  1.618  -0.426 -2.845 C1   XMH 1  
XMH C2   C2   C  0 1 Y N N -0.481 17.628 10.970 -3.957 0.071  -8.344 C2   XMH 2  
XMH N3   N3   N  0 1 N N N 1.228  18.453 7.511  -0.975 -0.346 -6.243 N3   XMH 3  
XMH C4   C4   C  0 1 Y N N 0.441  17.750 8.601  -1.859 0.143  -7.200 C4   XMH 4  
XMH C5   C5   C  0 1 Y N N 0.281  18.346 9.971  -3.111 -0.443 -7.385 C5   XMH 5  
XMH C6   C6   C  0 1 N N N 1.400  17.843 6.091  0.227  0.489  -6.314 C6   XMH 6  
XMH C7   C7   C  0 1 Y N N -0.218 16.424 8.370  -1.519 1.236  -7.996 C7   XMH 7  
XMH C8   C8   C  0 1 N N N 1.908  19.826 7.752  -1.596 -0.108 -4.936 C8   XMH 8  
XMH C9   C9   C  0 1 N N N 3.226  19.619 5.494  0.648  0.152  -3.877 C9   XMH 9  
XMH C10  C10  C  0 1 N N N 2.780  18.102 5.389  1.249  0.013  -5.279 C10  XMH 10 
XMH N11  N11  N  0 1 Y N N -1.078 16.393 10.707 -3.596 1.104  -9.081 N11  XMH 11 
XMH C12  C12  C  0 1 Y N N -0.953 15.804 9.442  -2.420 1.687  -8.937 C12  XMH 12 
XMH C13  C13  C  0 1 N N N 3.254  20.111 6.995  -0.674 -0.617 -3.825 C13  XMH 13 
XMH S14  S14  S  0 1 N N N 8.996  23.643 6.294  0.754  -2.145 2.496  S14  XMH 14 
XMH O15  O15  O  0 1 N N N 8.829  24.936 5.442  0.084  -3.360 2.190  O15  XMH 15 
XMH C16  C16  C  0 1 N N R 6.319  21.733 3.857  2.156  -0.290 -0.555 C16  XMH 16 
XMH C17  C17  C  0 1 N N N 7.196  22.820 4.499  1.621  -0.137 0.871  C17  XMH 17 
XMH N18  N18  N  0 1 N N N 8.017  22.379 5.661  0.659  -1.222 1.125  N18  XMH 18 
XMH C19  C19  C  0 1 N N N 6.538  20.261 5.920  0.269  -1.530 -1.260 C19  XMH 19 
XMH C20  C20  C  0 1 N N N 7.388  21.383 6.617  -0.389 -1.459 0.120  C20  XMH 20 
XMH N21  N21  N  0 1 N N N 5.584  20.874 4.908  1.035  -0.302 -1.502 N21  XMH 21 
XMH O22  O22  O  0 1 N N N 10.443 23.190 6.151  2.099  -2.037 2.942  O22  XMH 22 
XMH C23  C23  C  0 1 Y N N 7.820  25.267 8.249  0.350  -0.440 4.557  C23  XMH 23 
XMH C24  C24  C  0 1 Y N N 8.649  24.086 7.945  -0.224 -1.357 3.731  C24  XMH 24 
XMH C25  C25  C  0 1 Y N N 8.111  24.773 10.796 -1.800 -0.139 5.661  C25  XMH 25 
XMH C26  C26  C  0 1 Y N N 8.939  23.595 10.456 -2.357 -1.095 4.794  C26  XMH 26 
XMH C27  C27  C  0 1 Y N N 9.197  23.266 9.081  -1.573 -1.685 3.851  C27  XMH 27 
XMH C28  C28  C  0 1 Y N N 7.524  25.653 9.637  -0.428 0.194  5.540  C28  XMH 28 
XMH CL29 CL29 CL 0 0 N N N 6.707  26.699 14.132 -2.968 2.188  8.688  CL29 XMH 29 
XMH C30  C30  C  0 1 Y N N 6.696  26.837 9.996  0.128  1.149  6.407  C30  XMH 30 
XMH C31  C31  C  0 1 Y N N 7.820  25.152 12.173 -2.578 0.490  6.647  C31  XMH 31 
XMH C32  C32  C  0 1 Y N N 6.455  27.146 11.381 -0.654 1.740  7.350  C32  XMH 32 
XMH C33  C33  C  0 1 Y N N 7.011  26.310 12.474 -2.004 1.412  7.471  C33  XMH 33 
XMH C34  C34  C  0 1 N N N 5.500  22.317 2.616  3.071  0.864  -0.875 C34  XMH 34 
XMH O35  O35  O  0 1 N N N 5.430  23.685 2.466  4.362  0.819  -0.510 O35  XMH 35 
XMH C36  C36  C  0 1 N N N 5.969  24.327 1.244  5.242  1.931  -0.818 C36  XMH 36 
XMH C37  C37  C  0 1 N N N 4.911  24.743 0.189  6.648  1.628  -0.296 C37  XMH 37 
XMH O38  O38  O  0 1 N N N 5.324  21.541 1.683  2.642  1.830  -1.459 O38  XMH 38 
XMH H11  1H1  H  0 1 N N N 3.848  20.747 3.852  2.560  0.120  -2.884 H11  XMH 39 
XMH H12A 2H1  H  0 0 N N N 4.801  19.098 4.148  1.799  -1.478 -3.066 H12A XMH 40 
XMH H2   H2   H  0 1 N N N -0.592 18.062 11.953 -4.929 -0.376 -8.494 H2   XMH 41 
XMH H5   H5   H  0 1 N N N 0.730  19.300 10.207 -3.413 -1.289 -6.786 H5   XMH 42 
XMH H61  1H6  H  0 1 N N N 0.646  18.337 5.460  -0.039 1.526  -6.110 H61  XMH 43 
XMH H62  2H6  H  0 1 N N N 1.281  16.754 6.186  0.660  0.416  -7.311 H62  XMH 44 
XMH H7   H7   H  0 1 N N N -0.142 15.938 7.409  -0.558 1.718  -7.882 H7   XMH 45 
XMH H81  1H8  H  0 1 N N N 2.175  19.829 8.819  -1.766 0.959  -4.804 H81  XMH 46 
XMH H82  2H8  H  0 1 N N N 1.192  20.598 7.432  -2.549 -0.635 -4.885 H82  XMH 47 
XMH H9   H9   H  0 1 N N N 2.437  20.248 5.056  0.469  1.205  -3.659 H9   XMH 48 
XMH H101 1H10 H  0 0 N N N 2.672  17.852 4.323  2.150  0.622  -5.351 H101 XMH 49 
XMH H102 2H10 H  0 0 N N N 3.544  17.477 5.875  1.498  -1.030 -5.467 H102 XMH 50 
XMH H12  H12  H  0 1 N N N -1.426 14.849 9.264  -2.163 2.531  -9.560 H12  XMH 51 
XMH H131 1H13 H  0 0 N N N 4.052  19.558 7.513  -0.483 -1.680 -3.969 H131 XMH 52 
XMH H132 2H13 H  0 0 N N N 3.433  21.196 7.001  -1.150 -0.459 -2.857 H132 XMH 53 
XMH H16  H16  H  0 1 N N N 6.942  20.964 3.378  2.710  -1.225 -0.637 H16  XMH 54 
XMH H171 1H17 H  0 0 N N N 6.503  23.582 4.886  2.445  -0.205 1.581  H171 XMH 55 
XMH H172 2H17 H  0 0 N N N 7.887  23.187 3.726  1.124  0.826  0.976  H172 XMH 56 
XMH H191 1H19 H  0 0 N N N 5.955  19.727 6.684  0.939  -2.389 -1.299 H191 XMH 57 
XMH H192 2H19 H  0 0 N N N 7.214  19.564 5.404  -0.499 -1.635 -2.025 H192 XMH 58 
XMH H201 1H20 H  0 0 N N N 6.697  21.952 7.257  -0.896 -2.401 0.334  H201 XMH 59 
XMH H202 2H20 H  0 0 N N N 8.199  20.893 7.176  -1.110 -0.641 0.142  H202 XMH 60 
XMH H23  H23  H  0 1 N N N 7.423  25.859 7.438  1.397  -0.199 4.455  H23  XMH 61 
XMH H26  H26  H  0 1 N N N 9.351  22.981 11.243 -3.401 -1.359 4.875  H26  XMH 62 
XMH H27  H27  H  0 1 N N N 9.804  22.402 8.856  -2.003 -2.419 3.186  H27  XMH 63 
XMH H30  H30  H  0 1 N N N 6.278  27.462 9.220  1.172  1.413  6.325  H30  XMH 64 
XMH H31  H31  H  0 1 N N N 8.216  24.557 12.982 -3.625 0.246  6.752  H31  XMH 65 
XMH H32  H32  H  0 1 N N N 5.854  28.008 11.631 -0.224 2.474  8.016  H32  XMH 66 
XMH H361 1H36 H  0 0 N N N 6.607  23.574 0.758  4.865  2.836  -0.341 H361 XMH 67 
XMH H362 2H36 H  0 0 N N N 6.502  25.237 1.555  5.279  2.078  -1.897 H362 XMH 68 
XMH H371 1H37 H  0 0 N N N 4.856  23.976 -0.597 7.310  2.463  -0.527 H371 XMH 69 
XMH H372 2H37 H  0 0 N N N 5.198  25.707 -0.257 6.612  1.481  0.782  H372 XMH 70 
XMH H373 3H37 H  0 0 N N N 3.928  24.841 0.673  7.025  0.723  -0.773 H373 XMH 71 
# 
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 
XMH C1   C9   SING N N 1  
XMH C1   N21  SING N N 2  
XMH C1   H11  SING N N 3  
XMH C1   H12A SING N N 4  
XMH C2   C5   DOUB Y N 5  
XMH C2   N11  SING Y N 6  
XMH C2   H2   SING N N 7  
XMH N3   C4   SING N N 8  
XMH N3   C6   SING N N 9  
XMH N3   C8   SING N N 10 
XMH C4   C5   SING Y N 11 
XMH C4   C7   DOUB Y N 12 
XMH C5   H5   SING N N 13 
XMH C6   C10  SING N N 14 
XMH C6   H61  SING N N 15 
XMH C6   H62  SING N N 16 
XMH C7   C12  SING Y N 17 
XMH C7   H7   SING N N 18 
XMH C8   C13  SING N N 19 
XMH C8   H81  SING N N 20 
XMH C8   H82  SING N N 21 
XMH C9   C10  SING N N 22 
XMH C9   C13  SING N N 23 
XMH C9   H9   SING N N 24 
XMH C10  H101 SING N N 25 
XMH C10  H102 SING N N 26 
XMH N11  C12  DOUB Y N 27 
XMH C12  H12  SING N N 28 
XMH C13  H131 SING N N 29 
XMH C13  H132 SING N N 30 
XMH S14  O15  DOUB N N 31 
XMH S14  N18  SING N N 32 
XMH S14  O22  DOUB N N 33 
XMH S14  C24  SING N N 34 
XMH C16  C17  SING N N 35 
XMH C16  N21  SING N N 36 
XMH C16  C34  SING N N 37 
XMH C16  H16  SING N N 38 
XMH C17  N18  SING N N 39 
XMH C17  H171 SING N N 40 
XMH C17  H172 SING N N 41 
XMH N18  C20  SING N N 42 
XMH C19  C20  SING N N 43 
XMH C19  N21  SING N N 44 
XMH C19  H191 SING N N 45 
XMH C19  H192 SING N N 46 
XMH C20  H201 SING N N 47 
XMH C20  H202 SING N N 48 
XMH C23  C24  SING Y N 49 
XMH C23  C28  DOUB Y N 50 
XMH C23  H23  SING N N 51 
XMH C24  C27  DOUB Y N 52 
XMH C25  C26  DOUB Y N 53 
XMH C25  C28  SING Y N 54 
XMH C25  C31  SING Y N 55 
XMH C26  C27  SING Y N 56 
XMH C26  H26  SING N N 57 
XMH C27  H27  SING N N 58 
XMH C28  C30  SING Y N 59 
XMH CL29 C33  SING N N 60 
XMH C30  C32  DOUB Y N 61 
XMH C30  H30  SING N N 62 
XMH C31  C33  DOUB Y N 63 
XMH C31  H31  SING N N 64 
XMH C32  C33  SING Y N 65 
XMH C32  H32  SING N N 66 
XMH C34  O35  SING N N 67 
XMH C34  O38  DOUB N N 68 
XMH O35  C36  SING N N 69 
XMH C36  C37  SING N N 70 
XMH C36  H361 SING N N 71 
XMH C36  H362 SING N N 72 
XMH C37  H371 SING N N 73 
XMH C37  H372 SING N N 74 
XMH C37  H373 SING N N 75 
# 
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 
XMH SMILES           ACDLabs              10.04 Clc2ccc1cc(ccc1c2)S(=O)(=O)N5CC(C(=O)OCC)N(CC4CCN(c3ccncc3)CC4)CC5                                                                                                                                         
XMH InChI            InChI                1.02b InChI=1/C28H33ClN4O4S/c1-2-37-28(34)27-20-33(38(35,36)26-6-4-22-17-24(29)5-3-23(22)18-26)16-15-32(27)19-21-9-13-31(14-10-21)25-7-11-30-12-8-25/h3-8,11-12,17-18,21,27H,2,9-10,13-16,19-20H2,1H3/t27-/m1/s1 
XMH InChIKey         InChI                1.02b KTOZABIXRDAUJO-HHHXNRCGBV                                                                                                                                                                                  
XMH SMILES_CANONICAL CACTVS               3.341 CCOC(=O)[C@H]1CN(CCN1CC2CCN(CC2)c3ccncc3)[S](=O)(=O)c4ccc5cc(Cl)ccc5c4                                                                                                                                     
XMH SMILES           CACTVS               3.341 CCOC(=O)[CH]1CN(CCN1CC2CCN(CC2)c3ccncc3)[S](=O)(=O)c4ccc5cc(Cl)ccc5c4                                                                                                                                      
XMH SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 CCOC(=O)[C@H]1C[N@](CC[N@@]1CC2CCN(CC2)c3ccncc3)S(=O)(=O)c4ccc5cc(ccc5c4)Cl                                                                                                                                
XMH SMILES           "OpenEye OEToolkits" 1.5.0 CCOC(=O)C1CN(CCN1CC2CCN(CC2)c3ccncc3)S(=O)(=O)c4ccc5cc(ccc5c4)Cl                                                                                                                                           
# 
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 
XMH "SYSTEMATIC NAME" ACDLabs              10.04 "ethyl (2R)-4-[(6-chloronaphthalen-2-yl)sulfonyl]-1-[(1-pyridin-4-ylpiperidin-4-yl)methyl]piperazine-2-carboxylate"     
XMH "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "ethyl (1S,2R,4S)-4-(6-chloronaphthalen-2-yl)sulfonyl-1-[(1-pyridin-4-ylpiperidin-4-yl)methyl]piperazine-2-carboxylate" 
# 
