data_189
# 
_chem_comp.id                                    189 
_chem_comp.name                                  N-BENZYL-2-(2,6-DIMETHYLPHENOXY)-N-[((3R,4S)-4-{[ISOBUTYL(PHENYLSULFONYL)AMINO]METHYL}PYRROLIDIN-3-YL)METHYL]ACETAMIDE 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C33 H43 N3 O4 S" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         ? 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2004-10-13 
_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                        577.777 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     189 
_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        1XL2 
_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 
189 C1   C1   C 0 1 Y N N 26.068 -1.139 19.751 -3.985 1.681  4.022  C1   189 1  
189 C6   C6   C 0 1 Y N N 24.716 -0.824 19.914 -3.088 2.058  3.041  C6   189 2  
189 C5   C5   C 0 1 Y N N 23.741 -1.606 19.291 -3.373 1.810  1.711  C5   189 3  
189 C4   C4   C 0 1 Y N N 24.133 -2.680 18.486 -4.556 1.185  1.363  C4   189 4  
189 S10  S10  S 0 1 N N N 22.881 -3.674 17.670 -4.919 0.869  -0.332 S10  189 5  
189 O15  O15  O 0 1 N N N 21.656 -3.308 18.411 -6.333 0.738  -0.406 O15  189 6  
189 O14  O14  O 0 1 N N N 23.383 -5.030 17.899 -4.139 1.796  -1.074 O14  189 7  
189 N13  N13  N 0 1 N N N 22.733 -3.439 16.097 -4.310 -0.627 -0.699 N13  189 8  
189 C20  C20  C 0 1 N N N 22.580 -2.085 15.542 -2.912 -0.767 -1.112 C20  189 9  
189 C21  C21  C 0 1 N N R 21.200 -1.526 15.986 -2.040 -1.030 0.117  C21  189 10 
189 C25  C25  C 0 1 N N R 20.122 -2.285 15.168 -0.549 -1.094 -0.286 C25  189 11 
189 C26  C26  C 0 1 N N N 18.742 -1.977 15.765 0.164  0.220  0.038  C26  189 12 
189 N27  N27  N 0 1 N N N 18.582 -2.608 17.074 1.571  0.123  -0.358 N27  189 13 
189 C35  C35  C 0 1 N N N 18.672 -1.832 18.083 2.488  -0.329 0.521  C35  189 14 
189 O46  O46  O 0 1 N N N 18.609 -0.603 17.957 2.146  -0.667 1.634  O46  189 15 
189 C36  C36  C 0 1 N N N 18.971 -2.263 19.506 3.938  -0.413 0.120  C36  189 16 
189 O37  O37  O 0 1 N N N 18.574 -1.180 20.346 4.686  -1.036 1.166  O37  189 17 
189 C38  C38  C 0 1 Y N N 18.140 -1.455 21.629 5.979  -1.084 0.749  C38  189 18 
189 C43  C43  C 0 1 Y N N 19.001 -1.110 22.686 6.840  -0.034 1.033  C43  189 19 
189 C45  C45  C 0 1 N N N 20.347 -0.454 22.395 6.343  1.162  1.804  C45  189 20 
189 C42  C42  C 0 1 Y N N 18.556 -1.223 24.000 8.154  -0.085 0.609  C42  189 21 
189 C41  C41  C 0 1 Y N N 17.416 -1.971 24.302 8.611  -1.182 -0.099 C41  189 22 
189 C40  C40  C 0 1 Y N N 16.575 -2.371 23.262 7.754  -2.229 -0.383 C40  189 23 
189 C39  C39  C 0 1 Y N N 16.923 -2.062 21.937 6.442  -2.186 0.044  C39  189 24 
189 C44  C44  C 0 1 N N N 15.914 -2.445 20.857 5.509  -3.328 -0.266 C44  189 25 
189 C24  C24  C 0 1 N N N 20.255 -1.601 13.796 -0.002 -2.246 0.597  C24  189 26 
189 N23  N23  N 0 1 N N N 20.491 -0.172 14.109 -1.123 -3.222 0.617  N23  189 27 
189 C22  C22  C 0 1 N N N 21.077 -0.080 15.454 -2.358 -2.414 0.712  C22  189 28 
189 C3   C3   C 0 1 Y N N 25.479 -2.999 18.313 -5.455 0.812  2.344  C3   189 29 
189 C2   C2   C 0 1 Y N N 26.450 -2.228 18.965 -5.168 1.056  3.674  C2   189 30 
189 C16  C16  C 0 1 N N N 21.386 -5.857 14.979 -4.731 -2.462 -2.981 C16  189 31 
189 C17  C17  C 0 1 N N N 22.445 -5.019 14.233 -5.813 -2.077 -1.971 C17  189 32 
189 C19  C19  C 0 1 N N N 23.434 -4.357 15.198 -5.169 -1.810 -0.609 C19  189 33 
189 C18  C18  C 0 1 N N N 23.179 -5.910 13.232 -6.822 -3.220 -1.843 C18  189 34 
189 C28  C28  C 0 1 N N N 18.400 -4.019 17.286 1.982  0.517  -1.708 C28  189 35 
189 C29  C29  C 0 1 Y N N 17.030 -4.364 17.875 2.195  2.008  -1.753 C29  189 36 
189 C34  C34  C 0 1 Y N N 16.902 -5.498 18.683 3.465  2.530  -1.596 C34  189 37 
189 C33  C33  C 0 1 Y N N 15.671 -5.838 19.251 3.660  3.898  -1.638 C33  189 38 
189 C32  C32  C 0 1 Y N N 14.559 -5.029 18.998 2.585  4.744  -1.837 C32  189 39 
189 C31  C31  C 0 1 Y N N 14.683 -3.910 18.171 1.315  4.222  -1.994 C31  189 40 
189 C30  C30  C 0 1 Y N N 15.915 -3.574 17.601 1.120  2.854  -1.957 C30  189 41 
189 H1   H1   H 0 1 N N N 26.839 -0.524 20.246 -3.762 1.874  5.061  H1   189 42 
189 H6   H6   H 0 1 N N N 24.419 0.040  20.533 -2.163 2.546  3.313  H6   189 43 
189 H5   H5   H 0 1 N N N 22.671 -1.377 19.433 -2.672 2.105  0.944  H5   189 44 
189 H201 1H20 H 0 0 N N N 22.718 -2.057 14.436 -2.820 -1.601 -1.808 H201 189 45 
189 H202 2H20 H 0 0 N N N 23.424 -1.411 15.818 -2.584 0.151  -1.601 H202 189 46 
189 H21  H21  H 0 1 N N N 21.091 -1.609 17.093 -2.197 -0.252 0.865  H21  189 47 
189 H25  H25  H 0 1 N N N 20.237 -3.394 15.144 -0.446 -1.337 -1.344 H25  189 48 
189 H261 1H26 H 0 0 N N N 17.920 -2.263 15.068 -0.311 1.035  -0.508 H261 189 49 
189 H262 2H26 H 0 0 N N N 18.551 -0.879 15.812 0.100  0.415  1.108  H262 189 50 
189 H361 1H36 H 0 0 N N N 20.030 -2.577 19.660 4.029  -1.003 -0.793 H361 189 51 
189 H362 2H36 H 0 0 N N N 18.498 -3.234 19.783 4.326  0.590  -0.056 H362 189 52 
189 H451 1H45 H 0 0 N N N 20.168 0.456  21.776 6.490  0.993  2.871  H451 189 53 
189 H452 2H45 H 0 0 N N N 21.030 -0.180 23.233 6.897  2.048  1.497  H452 189 54 
189 H453 3H45 H 0 0 N N N 20.908 -1.103 21.682 5.282  1.308  1.603  H453 189 55 
189 H42  H42  H 0 1 N N N 19.111 -0.716 24.808 8.824  0.732  0.829  H42  189 56 
189 H41  H41  H 0 1 N N N 17.184 -2.242 25.346 9.638  -1.220 -0.430 H41  189 57 
189 H40  H40  H 0 1 N N N 15.647 -2.924 23.484 8.114  -3.085 -0.936 H40  189 58 
189 H441 1H44 H 0 0 N N N 16.439 -3.092 20.116 5.555  -4.063 0.537  H441 189 59 
189 H442 2H44 H 0 0 N N N 14.941 -2.930 21.103 4.490  -2.951 -0.356 H442 189 60 
189 H443 3H44 H 0 0 N N N 15.696 -1.531 20.256 5.807  -3.796 -1.204 H443 189 61 
189 H241 1H24 H 0 0 N N N 19.391 -1.779 13.115 0.214  -1.889 1.603  H241 189 62 
189 H242 2H24 H 0 0 N N N 21.031 -2.055 13.136 0.885  -2.690 0.145  H242 189 63 
189 H23  H23  H 0 1 N N N 19.649 0.395  14.009 -1.045 -3.735 1.482  H23  189 64 
189 H221 1H22 H 0 0 N N N 22.041 0.480  15.476 -2.655 -2.311 1.755  H221 189 65 
189 H222 2H22 H 0 0 N N N 20.508 0.593  16.137 -3.156 -2.889 0.141  H222 189 66 
189 H3   H3   H 0 1 N N N 25.771 -3.847 17.671 -6.380 0.324  2.072  H3   189 67 
189 H2   H2   H 0 1 N N N 27.519 -2.479 18.859 -5.869 0.762  4.441  H2   189 68 
189 H161 1H16 H 0 0 N N N 20.856 -5.248 15.748 -5.199 -2.771 -3.915 H161 189 69 
189 H162 2H16 H 0 0 N N N 20.666 -6.339 14.277 -4.083 -1.605 -3.165 H162 189 70 
189 H163 3H16 H 0 0 N N N 21.863 -6.609 15.649 -4.138 -3.286 -2.581 H163 189 71 
189 H17  H17  H 0 1 N N N 21.924 -4.196 13.690 -6.325 -1.177 -2.313 H17  189 72 
189 H191 1H19 H 0 0 N N N 24.034 -5.111 15.760 -5.948 -1.638 0.134  H191 189 73 
189 H192 2H19 H 0 0 N N N 24.268 -3.852 14.656 -4.571 -2.672 -0.315 H192 189 74 
189 H181 1H18 H 0 0 N N N 22.480 -6.427 12.534 -6.310 -4.119 -1.501 H181 189 75 
189 H182 2H18 H 0 0 N N N 23.944 -5.304 12.693 -7.594 -2.945 -1.124 H182 189 76 
189 H183 3H18 H 0 0 N N N 23.618 -6.815 13.714 -7.281 -3.410 -2.814 H183 189 77 
189 H281 1H28 H 0 0 N N N 19.220 -4.436 17.916 2.911  0.009  -1.968 H281 189 78 
189 H282 2H28 H 0 0 N N N 18.584 -4.590 16.346 1.204  0.239  -2.419 H282 189 79 
189 H34  H34  H 0 1 N N N 17.784 -6.133 18.875 4.305  1.869  -1.441 H34  189 80 
189 H33  H33  H 0 1 N N N 15.578 -6.732 19.890 4.653  4.306  -1.515 H33  189 81 
189 H32  H32  H 0 1 N N N 13.584 -5.274 19.451 2.738  5.812  -1.868 H32  189 82 
189 H31  H31  H 0 1 N N N 13.798 -3.285 17.966 0.475  4.883  -2.149 H31  189 83 
189 H30  H30  H 0 1 N N N 16.006 -2.694 16.942 0.128  2.446  -2.080 H30  189 84 
# 
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 
189 C1  C6   DOUB Y N 1  
189 C1  C2   SING Y N 2  
189 C1  H1   SING N N 3  
189 C6  C5   SING Y N 4  
189 C6  H6   SING N N 5  
189 C5  C4   DOUB Y N 6  
189 C5  H5   SING N N 7  
189 C4  S10  SING N N 8  
189 C4  C3   SING Y N 9  
189 S10 O15  DOUB N N 10 
189 S10 O14  DOUB N N 11 
189 S10 N13  SING N N 12 
189 N13 C20  SING N N 13 
189 N13 C19  SING N N 14 
189 C20 C21  SING N N 15 
189 C20 H201 SING N N 16 
189 C20 H202 SING N N 17 
189 C21 C25  SING N N 18 
189 C21 C22  SING N N 19 
189 C21 H21  SING N N 20 
189 C25 C26  SING N N 21 
189 C25 C24  SING N N 22 
189 C25 H25  SING N N 23 
189 C26 N27  SING N N 24 
189 C26 H261 SING N N 25 
189 C26 H262 SING N N 26 
189 N27 C35  SING N N 27 
189 N27 C28  SING N N 28 
189 C35 O46  DOUB N N 29 
189 C35 C36  SING N N 30 
189 C36 O37  SING N N 31 
189 C36 H361 SING N N 32 
189 C36 H362 SING N N 33 
189 O37 C38  SING N N 34 
189 C38 C43  DOUB Y N 35 
189 C38 C39  SING Y N 36 
189 C43 C45  SING N N 37 
189 C43 C42  SING Y N 38 
189 C45 H451 SING N N 39 
189 C45 H452 SING N N 40 
189 C45 H453 SING N N 41 
189 C42 C41  DOUB Y N 42 
189 C42 H42  SING N N 43 
189 C41 C40  SING Y N 44 
189 C41 H41  SING N N 45 
189 C40 C39  DOUB Y N 46 
189 C40 H40  SING N N 47 
189 C39 C44  SING N N 48 
189 C44 H441 SING N N 49 
189 C44 H442 SING N N 50 
189 C44 H443 SING N N 51 
189 C24 N23  SING N N 52 
189 C24 H241 SING N N 53 
189 C24 H242 SING N N 54 
189 N23 C22  SING N N 55 
189 N23 H23  SING N N 56 
189 C22 H221 SING N N 57 
189 C22 H222 SING N N 58 
189 C3  C2   DOUB Y N 59 
189 C3  H3   SING N N 60 
189 C2  H2   SING N N 61 
189 C16 C17  SING N N 62 
189 C16 H161 SING N N 63 
189 C16 H162 SING N N 64 
189 C16 H163 SING N N 65 
189 C17 C19  SING N N 66 
189 C17 C18  SING N N 67 
189 C17 H17  SING N N 68 
189 C19 H191 SING N N 69 
189 C19 H192 SING N N 70 
189 C18 H181 SING N N 71 
189 C18 H182 SING N N 72 
189 C18 H183 SING N N 73 
189 C28 C29  SING N N 74 
189 C28 H281 SING N N 75 
189 C28 H282 SING N N 76 
189 C29 C34  DOUB Y N 77 
189 C29 C30  SING Y N 78 
189 C34 C33  SING Y N 79 
189 C34 H34  SING N N 80 
189 C33 C32  DOUB Y N 81 
189 C33 H33  SING N N 82 
189 C32 C31  SING Y N 83 
189 C32 H32  SING N N 84 
189 C31 C30  DOUB Y N 85 
189 C31 H31  SING N N 86 
189 C30 H30  SING N N 87 
# 
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 
189 SMILES           ACDLabs              10.04 O=S(=O)(N(CC1C(CNC1)CN(C(=O)COc2c(cccc2C)C)Cc3ccccc3)CC(C)C)c4ccccc4                                                                                                                               
189 InChI            InChI                1.02b InChI=1/C33H43N3O4S/c1-25(2)20-36(41(38,39)31-16-9-6-10-17-31)23-30-19-34-18-29(30)22-35(21-28-14-7-5-8-15-28)32(37)24-40-33-26(3)12-11-13-27(33)4/h5-17,25,29-30,34H,18-24H2,1-4H3/t29-,30-/m1/s1 
189 InChIKey         InChI                1.02b MQRMHPRUUKDEKO-LOYHVIPDBY                                                                                                                                                                          
189 SMILES_CANONICAL CACTVS               3.341 CC(C)CN(C[C@H]1CNC[C@@H]1CN(Cc2ccccc2)C(=O)COc3c(C)cccc3C)[S](=O)(=O)c4ccccc4                                                                                                                      
189 SMILES           CACTVS               3.341 CC(C)CN(C[CH]1CNC[CH]1CN(Cc2ccccc2)C(=O)COc3c(C)cccc3C)[S](=O)(=O)c4ccccc4                                                                                                                         
189 SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 Cc1cccc(c1OCC(=O)N(Cc2ccccc2)C[C@H]3CNC[C@@H]3C[N@@](CC(C)C)S(=O)(=O)c4ccccc4)C                                                                                                                    
189 SMILES           "OpenEye OEToolkits" 1.5.0 Cc1cccc(c1OCC(=O)N(Cc2ccccc2)CC3CNCC3CN(CC(C)C)S(=O)(=O)c4ccccc4)C                                                                                                                                 
# 
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 
189 "SYSTEMATIC NAME" ACDLabs              10.04 N-benzyl-2-(2,6-dimethylphenoxy)-N-{[(3R,4R)-4-{[(2-methylpropyl)(phenylsulfonyl)amino]methyl}pyrrolidin-3-yl]methyl}acetamide         
189 "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 2-(2,6-dimethylphenoxy)-N-[[(3R,4R)-4-[(2-methylpropyl-(phenylsulfonyl)amino)methyl]pyrrolidin-3-yl]methyl]-N-(phenylmethyl)ethanamide 
# 
