data_403
# 
_chem_comp.id                                    403 
_chem_comp.name                                  "(2R,3R)-4-[4-(2-chlorophenyl)piperazin-1-yl]-2,3-dihydroxy-4-oxo-N-(2-thiophen-2-ylethyl)butanamide" 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C20 H24 Cl 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                     2009-11-15 
_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                        437.940 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     403 
_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        3KMC 
_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 
403 C1   C1   C  0 1 N N R 50.170 35.061 39.734 0.517  -2.382 -0.432 C1   403 1  
403 C2   C2   C  0 1 N N N 51.123 35.306 38.512 -0.927 -2.788 -0.571 C2   403 2  
403 C3   C3   C  0 1 N N R 50.175 33.545 39.965 0.706  -1.607 0.874  C3   403 3  
403 N4   N4   N  0 1 N N N 50.632 34.816 37.275 -1.868 -1.855 -0.824 N4   403 4  
403 N5   N5   N  0 1 N N N 49.860 33.704 34.739 -3.753 0.139  -0.340 N5   403 5  
403 C6   C6   C  0 1 N N N 49.050 33.138 40.933 2.161  -1.252 1.041  C6   403 6  
403 S8   S8   S  0 1 Y N N 51.102 31.063 43.990 6.653  2.612  0.339  S8   403 7  
403 C9   C9   C  0 1 Y N N 49.602 31.435 44.828 6.041  1.260  -0.605 C9   403 8  
403 O10  O10  O  0 1 N N N 52.270 35.824 38.669 -1.244 -3.953 -0.456 O10  403 9  
403 C11  C11  C  0 1 N N N 49.184 34.683 36.955 -3.295 -2.210 -0.849 C11  403 10 
403 C12  C12  C  0 1 N N N 51.378 35.231 36.075 -1.494 -0.456 -1.076 C12  403 11 
403 C13  C13  C  0 1 N N N 51.283 34.044 35.086 -2.327 0.444  -0.157 C13  403 12 
403 C14  C14  C  0 1 N N N 49.019 33.496 35.958 -4.054 -1.238 0.061  C14  403 13 
403 C15  C15  C  0 1 Y N N 51.901 30.668 45.526 8.309  2.189  -0.071 C15  403 14 
403 O17  O17  O  0 1 N N N 47.902 33.016 40.541 2.799  -1.725 1.958  O17  403 15 
403 C18  C18  C  0 1 Y N N 49.715 31.267 46.214 7.063  0.598  -1.150 C18  403 16 
403 C19  C19  C  0 1 Y N N 51.022 30.836 46.602 8.314  1.110  -0.855 C19  403 17 
403 N20  N20  N  0 1 N N N 49.419 33.031 42.257 2.752  -0.407 0.173  N20  403 18 
403 O21  O21  O  0 1 N N N 50.729 35.788 40.842 1.340  -3.550 -0.415 O21  403 19 
403 O22  O22  O  0 1 N N N 51.491 33.193 40.389 0.283  -2.416 1.973  O22  403 20 
403 C23  C23  C  0 1 N N N 48.364 31.856 44.059 4.587  0.905  -0.773 C23  403 21 
403 C25  C25  C  0 1 N N N 48.508 33.196 43.371 4.167  -0.062 0.336  C25  403 22 
403 H1   H1   H  0 1 N N N 49.134 35.400 39.587 0.800  -1.750 -1.274 H1   403 23 
403 H3   H3   H  0 1 N N N 49.952 32.980 39.048 0.110  -0.695 0.844  H3   403 24 
403 C151 C151 C  0 0 Y N N 49.290 34.812 33.959 -4.553 1.048  0.358  C151 403 25 
403 H11  H11  H  0 1 N N N 48.613 34.484 37.874 -3.674 -2.131 -1.867 H11  403 26 
403 H11A H11A H  0 0 N N N 48.813 35.612 36.498 -3.425 -3.229 -0.485 H11A 403 27 
403 H12  H12  H  0 1 N N N 50.936 36.138 35.637 -0.434 -0.315 -0.863 H12  403 28 
403 H12A H12A H  0 0 N N N 52.428 35.446 36.325 -1.697 -0.204 -2.117 H12A 403 29 
403 H13  H13  H  0 1 N N N 51.750 33.163 35.551 -2.144 1.488  -0.411 H13  403 30 
403 H13A H13A H  0 0 N N N 51.813 34.316 34.161 -2.048 0.267  0.881  H13A 403 31 
403 H14  H14  H  0 1 N N N 47.963 33.425 35.657 -3.749 -1.390 1.097  H14  403 32 
403 H14A H14A H  0 0 N N N 49.331 32.565 36.454 -5.124 -1.419 -0.033 H14A 403 33 
403 H15  H15  H  0 1 N N N 52.927 30.342 45.617 9.189  2.721  0.261  H15  403 34 
403 H18  H18  H  0 1 N N N 48.908 31.443 46.910 6.924  -0.273 -1.774 H18  403 35 
403 H19  H19  H  0 1 N N N 51.304 30.657 47.629 9.226  0.669  -1.232 H19  403 36 
403 HN20 HN20 H  0 0 N N N 50.376 32.826 42.461 2.242  -0.029 -0.560 HN20 403 37 
403 HO21 HO21 H  0 0 N N N 51.567 36.157 40.589 1.144  -4.160 0.309  HO21 403 38 
403 HO22 HO22 H  0 0 N N N 51.535 32.257 40.543 0.772  -3.246 2.061  HO22 403 39 
403 H23  H23  H  0 1 N N N 48.163 31.096 43.290 3.982  1.810  -0.714 H23  403 40 
403 H23A H23A H  0 0 N N N 47.526 31.923 44.769 4.438  0.432  -1.743 H23A 403 41 
403 H25  H25  H  0 1 N N N 48.908 33.939 44.076 4.316  0.412  1.306  H25  403 42 
403 H25A H25A H  0 0 N N N 47.528 33.539 43.007 4.771  -0.967 0.277  H25A 403 43 
403 C16  C16  C  0 1 Y N N 47.066 35.280 31.879 -6.137 2.848  1.740  C16  403 44 
403 C17  C17  C  0 1 Y N N 46.802 34.380 33.101 -5.222 2.068  2.422  C17  403 45 
403 C181 C181 C  0 0 Y N N 47.913 34.146 34.140 -4.430 1.168  1.735  C181 403 46 
403 C191 C191 C  0 0 Y N N 49.555 35.712 32.738 -5.470 1.837  -0.326 C191 403 47 
403 C20  C20  C  0 1 Y N N 48.443 35.946 31.698 -6.259 2.734  0.367  C20  403 48 
403 CL1  CL1  CL 0 0 N N N 51.137 36.478 32.529 -5.624 1.695  -2.050 CL1  403 49 
403 H21  H21  H  0 1 N N N 46.286 35.444 31.150 -6.755 3.550  2.280  H21  403 50 
403 H22  H22  H  0 1 N N N 45.837 33.913 33.229 -5.129 2.160  3.494  H22  403 51 
403 H231 H231 H  0 0 N N N 47.727 33.515 34.996 -3.715 0.560  2.270  H231 403 52 
403 H24  H24  H  0 1 N N N 48.629 36.577 30.842 -6.975 3.345  -0.163 H24  403 53 
# 
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 
403 C1   C2   SING N N 1  
403 C1   C3   SING N N 2  
403 C1   O21  SING N N 3  
403 C1   H1   SING N N 4  
403 C2   N4   SING N N 5  
403 C2   O10  DOUB N N 6  
403 C3   C6   SING N N 7  
403 C3   O22  SING N N 8  
403 C3   H3   SING N N 9  
403 N4   C11  SING N N 10 
403 N4   C12  SING N N 11 
403 N5   C13  SING N N 12 
403 N5   C14  SING N N 13 
403 N5   C151 SING N N 14 
403 C6   O17  DOUB N N 15 
403 C6   N20  SING N N 16 
403 S8   C9   SING Y N 17 
403 S8   C15  SING Y N 18 
403 C9   C18  DOUB Y N 19 
403 C9   C23  SING N N 20 
403 C11  C14  SING N N 21 
403 C11  H11  SING N N 22 
403 C11  H11A SING N N 23 
403 C12  C13  SING N N 24 
403 C12  H12  SING N N 25 
403 C12  H12A SING N N 26 
403 C13  H13  SING N N 27 
403 C13  H13A SING N N 28 
403 C14  H14  SING N N 29 
403 C14  H14A SING N N 30 
403 C15  C19  DOUB Y N 31 
403 C15  H15  SING N N 32 
403 C18  C19  SING Y N 33 
403 C18  H18  SING N N 34 
403 C19  H19  SING N N 35 
403 N20  C25  SING N N 36 
403 N20  HN20 SING N N 37 
403 O21  HO21 SING N N 38 
403 O22  HO22 SING N N 39 
403 C23  C25  SING N N 40 
403 C23  H23  SING N N 41 
403 C23  H23A SING N N 42 
403 C25  H25  SING N N 43 
403 C25  H25A SING N N 44 
403 C181 C151 DOUB Y N 45 
403 C151 C191 SING Y N 46 
403 C16  C17  DOUB Y N 47 
403 C17  C181 SING Y N 48 
403 C191 C20  DOUB Y N 49 
403 C16  C20  SING Y N 50 
403 C191 CL1  SING N N 51 
403 C16  H21  SING N N 52 
403 C17  H22  SING N N 53 
403 C181 H231 SING N N 54 
403 C20  H24  SING N N 55 
# 
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 
403 SMILES_CANONICAL CACTVS               3.352 "O[C@H]([C@@H](O)C(=O)N1CCN(CC1)c2ccccc2Cl)C(=O)NCCc3sccc3"                                                                                                           
403 SMILES           CACTVS               3.352 "O[CH]([CH](O)C(=O)N1CCN(CC1)c2ccccc2Cl)C(=O)NCCc3sccc3"                                                                                                              
403 SMILES_CANONICAL "OpenEye OEToolkits" 1.7.0 "c1ccc(c(c1)N2CCN(CC2)C(=O)[C@@H]([C@H](C(=O)NCCc3cccs3)O)O)Cl"                                                                                                       
403 SMILES           "OpenEye OEToolkits" 1.7.0 "c1ccc(c(c1)N2CCN(CC2)C(=O)C(C(C(=O)NCCc3cccs3)O)O)Cl"                                                                                                                
403 InChI            InChI                1.03  "InChI=1S/C20H24ClN3O4S/c21-15-5-1-2-6-16(15)23-9-11-24(12-10-23)20(28)18(26)17(25)19(27)22-8-7-14-4-3-13-29-14/h1-6,13,17-18,25-26H,7-12H2,(H,22,27)/t17-,18-/m1/s1" 
403 InChIKey         InChI                1.03  AZEKZZSSVLIPCQ-QZTJIDSGSA-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 
403 "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.6.1 "(2R,3R)-4-[4-(2-chlorophenyl)piperazin-1-yl]-2,3-dihydroxy-4-oxo-N-(2-thiophen-2-ylethyl)butanamide" 
# 
loop_
_pdbx_chem_comp_audit.comp_id 
_pdbx_chem_comp_audit.action_type 
_pdbx_chem_comp_audit.date 
_pdbx_chem_comp_audit.processing_site 
403 "Create component"     2009-11-15 RCSB 
403 "Modify aromatic_flag" 2011-06-04 RCSB 
403 "Modify descriptor"    2011-06-04 RCSB 
# 
