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 #