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 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 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 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" 189 InChI InChI 1.03 "InChI=1S/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 1.03 MQRMHPRUUKDEKO-LOYHVIPDSA-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 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" # loop_ _pdbx_chem_comp_audit.comp_id _pdbx_chem_comp_audit.action_type _pdbx_chem_comp_audit.date _pdbx_chem_comp_audit.processing_site 189 "Create component" 2004-10-13 RCSB 189 "Modify descriptor" 2011-06-04 RCSB #