data_SOX # _chem_comp.id SOX _chem_comp.name ;N-[(2S,4S,6R)-2-(DIHYDROXYMETHYL)-4-HYDROXY-3,3-DIMETHYL-7-OXO-4LAMBDA~4~-THIA-1-AZABICYCLO[3.2.0]HEPT-6-YL]-2-PHENYLAC ETAMIDE ; _chem_comp.type NON-POLYMER _chem_comp.pdbx_type HETAIN _chem_comp.formula "C16 H20 N2 O5 S" _chem_comp.mon_nstd_parent_comp_id ? _chem_comp.pdbx_synonyms "OXIDISED PENICILLIN G" _chem_comp.pdbx_formal_charge 0 _chem_comp.pdbx_initial_date 2001-09-11 _chem_comp.pdbx_modified_date 2020-06-17 _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 352.405 _chem_comp.one_letter_code ? _chem_comp.three_letter_code SOX _chem_comp.pdbx_model_coordinates_details ? _chem_comp.pdbx_model_coordinates_missing_flag N _chem_comp.pdbx_ideal_coordinates_details "OpenEye/OEToolkits V1.4.2" _chem_comp.pdbx_ideal_coordinates_missing_flag N _chem_comp.pdbx_model_coordinates_db_code 1GM8 _chem_comp.pdbx_subcomponent_list ? _chem_comp.pdbx_processing_site EBI # # 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 SOX O8 O8 O 0 1 N N N 11.793 -2.156 2.053 -2.804 1.597 2.717 O8 SOX 1 SOX C7 C7 C 0 1 N N N 12.837 -2.680 2.363 -1.816 1.436 3.397 C7 SOX 2 SOX N4 N4 N 0 1 N N N 13.150 -3.979 2.779 -0.584 0.917 3.131 N4 SOX 3 SOX C3 C3 C 0 1 N N S 12.353 -5.008 3.379 -0.293 -0.183 2.224 C3 SOX 4 SOX C11 C11 C 0 1 N N N 12.106 -6.204 2.448 0.284 0.410 0.979 C11 SOX 5 SOX O13 O13 O 0 1 N N N 12.488 -6.283 1.321 0.534 1.595 0.817 O13 SOX 6 SOX O12 O12 O 0 1 N N N 11.418 -7.167 3.126 0.492 -0.549 0.044 O12 SOX 7 SOX C2 C2 C 0 1 N N N 13.147 -5.364 4.656 0.617 -1.166 2.992 C2 SOX 8 SOX C10 C10 C 0 1 N N N 14.077 -6.600 4.516 2.119 -0.921 2.778 C10 SOX 9 SOX C9 C9 C 0 1 N N N 12.241 -5.641 5.874 0.289 -2.624 2.675 C9 SOX 10 SOX S1 S1 S 0 1 N N N 14.141 -3.869 5.003 0.245 -0.762 4.711 S1 SOX 11 SOX C5 C5 C 0 1 N N R 14.455 -3.558 3.247 -0.119 0.945 4.530 C5 SOX 12 SOX C6 C6 C 0 1 N N R 14.256 -2.194 2.560 -1.473 1.561 4.894 C6 SOX 13 SOX N14 N14 N 0 1 N N N 14.318 -0.986 3.333 -2.344 0.800 5.801 N14 SOX 14 SOX C15 C15 C 0 1 N N N 14.989 0.120 2.931 -2.071 0.669 7.149 C15 SOX 15 SOX O16 O16 O 0 1 N N N 15.665 0.313 1.923 -1.105 1.156 7.730 O16 SOX 16 SOX C17 C17 C 0 1 N N N 14.900 1.282 3.920 -3.135 -0.160 7.843 C17 SOX 17 SOX C18 C18 C 0 1 Y N N 16.301 1.799 4.224 -2.589 -1.402 8.499 C18 SOX 18 SOX C19 C19 C 0 1 Y N N 16.827 2.921 3.601 -2.525 -2.584 7.775 C19 SOX 19 SOX C20 C20 C 0 1 Y N N 18.065 3.431 4.005 -2.020 -3.734 8.382 C20 SOX 20 SOX C21 C21 C 0 1 Y N N 18.815 2.757 4.980 -1.584 -3.689 9.707 C21 SOX 21 SOX C22 C22 C 0 1 Y N N 18.316 1.602 5.591 -1.654 -2.495 10.424 C22 SOX 22 SOX C23 C23 C 0 1 Y N N 17.049 1.158 5.214 -2.159 -1.345 9.817 C23 SOX 23 SOX O5 O5 O 0 1 N N N 13.282 -2.709 5.338 -1.232 -1.404 4.896 O5 SOX 24 SOX H3 H3 H 0 1 N N N 11.370 -4.574 3.676 -1.245 -0.656 1.954 H3 SOX 25 SOX H12 H12 H 0 1 N N N 11.265 -7.906 2.550 0.869 -0.179 -0.782 H12 SOX 26 SOX H101 1H10 H 0 0 N N N 14.650 -6.857 5.437 2.339 0.151 2.789 H101 SOX 27 SOX H102 2H10 H 0 0 N N N 14.771 -6.467 3.653 2.703 -1.401 3.569 H102 SOX 28 SOX H103 3H10 H 0 0 N N N 13.496 -7.484 4.162 2.441 -1.329 1.815 H103 SOX 29 SOX H9C1 1H9C H 0 0 N N N 12.814 -5.898 6.795 0.059 -3.174 3.592 H9C1 SOX 30 SOX H9C2 2H9C H 0 0 N N N 11.490 -6.431 5.639 -0.576 -2.687 2.009 H9C2 SOX 31 SOX H9C3 3H9C H 0 0 N N N 11.552 -4.784 6.060 1.138 -3.111 2.185 H9C3 SOX 32 SOX HS HS H 0 1 N N N 15.063 -4.002 5.909 1.130 -1.137 5.652 HS SOX 33 SOX H5 H5 H 0 1 N N N 15.298 -4.155 2.828 0.751 1.594 4.664 H5 SOX 34 SOX H6 H6 H 0 1 N N N 14.817 -2.115 1.599 -1.423 2.599 5.239 H6 SOX 35 SOX H14 H14 H 0 1 N N N 13.833 -0.959 4.230 -3.168 0.354 5.424 H14 SOX 36 SOX H171 1H17 H 0 0 N N N 14.343 1.006 4.845 -3.901 -0.439 7.109 H171 SOX 37 SOX H172 2H17 H 0 0 N N N 14.221 2.090 3.560 -3.634 0.466 8.593 H172 SOX 38 SOX H19 H19 H 0 1 N N N 16.268 3.411 2.786 -2.862 -2.628 6.743 H19 SOX 39 SOX H20 H20 H 0 1 N N N 18.451 4.362 3.557 -1.965 -4.664 7.824 H20 SOX 40 SOX H21 H21 H 0 1 N N N 19.808 3.142 5.268 -1.191 -4.584 10.180 H21 SOX 41 SOX H22 H22 H 0 1 N N N 18.907 1.059 6.348 -1.314 -2.460 11.455 H22 SOX 42 SOX H23 H23 H 0 1 N N N 16.624 0.272 5.714 -2.209 -0.419 10.383 H23 SOX 43 SOX HO5 HO5 H 0 1 N N N 13.798 -1.932 5.518 -1.527 -2.003 4.170 HO5 SOX 44 # # 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 SOX O8 C7 DOUB N N 1 SOX C7 N4 SING N N 2 SOX C7 C6 SING N N 3 SOX N4 C3 SING N N 4 SOX N4 C5 SING N N 5 SOX C3 C11 SING N N 6 SOX C3 C2 SING N N 7 SOX C3 H3 SING N N 8 SOX C11 O13 DOUB N N 9 SOX C11 O12 SING N N 10 SOX O12 H12 SING N N 11 SOX C2 C10 SING N N 12 SOX C2 C9 SING N N 13 SOX C2 S1 SING N N 14 SOX C10 H101 SING N N 15 SOX C10 H102 SING N N 16 SOX C10 H103 SING N N 17 SOX C9 H9C1 SING N N 18 SOX C9 H9C2 SING N N 19 SOX C9 H9C3 SING N N 20 SOX S1 C5 SING N N 21 SOX S1 O5 SING N N 22 SOX S1 HS SING N N 23 SOX C5 C6 SING N N 24 SOX C5 H5 SING N N 25 SOX C6 N14 SING N N 26 SOX C6 H6 SING N N 27 SOX N14 C15 SING N N 28 SOX N14 H14 SING N N 29 SOX C15 O16 DOUB N N 30 SOX C15 C17 SING N N 31 SOX C17 C18 SING N N 32 SOX C17 H171 SING N N 33 SOX C17 H172 SING N N 34 SOX C18 C19 DOUB Y N 35 SOX C18 C23 SING Y N 36 SOX C19 C20 SING Y N 37 SOX C19 H19 SING N N 38 SOX C20 C21 DOUB Y N 39 SOX C20 H20 SING N N 40 SOX C21 C22 SING Y N 41 SOX C21 H21 SING N N 42 SOX C22 C23 DOUB Y N 43 SOX C22 H22 SING N N 44 SOX C23 H23 SING N N 45 SOX O5 HO5 SING N N 46 # # 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 SOX SMILES ACDLabs 10.04 "O=C2N1C(C(=O)O)C(C)(C)S(O)C1C2NC(=O)Cc3ccccc3" SOX SMILES_CANONICAL CACTVS 3.341 "CC1(C)[C@@H](N2[C@@H]([C@H](NC(=O)Cc3ccccc3)C2=O)[SH]1O)C(O)=O" SOX SMILES CACTVS 3.341 "CC1(C)[CH](N2[CH]([CH](NC(=O)Cc3ccccc3)C2=O)[SH]1O)C(O)=O" SOX SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 "CC1([C@@H](N2[C@H]([S@H]1O)[C@@H](C2=O)NC(=O)Cc3ccccc3)C(=O)O)C" SOX SMILES "OpenEye OEToolkits" 1.5.0 "CC1(C(N2C(S1O)C(C2=O)NC(=O)Cc3ccccc3)C(=O)O)C" SOX InChI InChI 1.03 "InChI=1S/C16H20N2O5S/c1-16(2)12(15(21)22)18-13(20)11(14(18)24(16)23)17-10(19)8-9-6-4-3-5-7-9/h3-7,11-12,14,23-24H,8H2,1-2H3,(H,17,19)(H,21,22)/t11-,12+,14-/m1/s1" SOX InChIKey InChI 1.03 WMPGEOZLAYOFHH-MBNYWOFBSA-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 SOX "SYSTEMATIC NAME" ACDLabs 10.04 "(2S,4S,5R,6R)-4-hydroxy-3,3-dimethyl-7-oxo-6-[(phenylacetyl)amino]-4lambda~4~-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid" SOX "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "(2S,4S,5R,6R)-4-hydroxy-3,3-dimethyl-7-oxo-6-(2-phenylethanoylamino)-4$l^{4}-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid" # # loop_ _pdbx_chem_comp_audit.comp_id _pdbx_chem_comp_audit.action_type _pdbx_chem_comp_audit.date _pdbx_chem_comp_audit.processing_site SOX "Create component" 2001-09-11 EBI SOX "Modify descriptor" 2011-06-04 RCSB SOX "Modify synonyms" 2020-06-05 PDBE # _pdbx_chem_comp_synonyms.ordinal 1 _pdbx_chem_comp_synonyms.comp_id SOX _pdbx_chem_comp_synonyms.name "OXIDISED PENICILLIN G" _pdbx_chem_comp_synonyms.provenance ? _pdbx_chem_comp_synonyms.type ? ##