data_1QL # _chem_comp.id 1QL _chem_comp.name "(2R)-5-[(carbamoyloxy)methyl]-2-{(1S)-1-methoxy-2-oxo-1-[(thiophen-2-ylacetyl)amino]ethyl}-3,6-dihydro-2H-1,3-thiazine-4-carboxylic acid" _chem_comp.type NON-POLYMER _chem_comp.pdbx_type HETAIN _chem_comp.formula "C16 H19 N3 O7 S2" _chem_comp.mon_nstd_parent_comp_id ? _chem_comp.pdbx_synonyms "Cefoxitin, bound form" _chem_comp.pdbx_formal_charge 0 _chem_comp.pdbx_initial_date 2013-04-26 _chem_comp.pdbx_modified_date 2021-03-13 _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 429.468 _chem_comp.one_letter_code ? _chem_comp.three_letter_code 1QL _chem_comp.pdbx_model_coordinates_details ? _chem_comp.pdbx_model_coordinates_missing_flag Y _chem_comp.pdbx_ideal_coordinates_details Corina _chem_comp.pdbx_ideal_coordinates_missing_flag N _chem_comp.pdbx_model_coordinates_db_code 4KEN _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 1QL C4 C4 C 0 1 Y N N 28.415 4.346 11.092 5.636 0.876 -0.175 C4 FOX 1 1QL C2 C2 C 0 1 N N N 26.433 3.849 9.631 3.247 0.296 -0.073 C2 FOX 2 1QL N2 N2 N 0 1 N N N 27.740 6.938 7.749 -1.424 -1.097 0.157 N2 FOX 3 1QL C6 C6 C 0 1 Y N N 30.269 5.636 11.205 7.611 -0.029 -0.904 C6 FOX 4 1QL O6 O6 O 0 1 N N N 28.731 9.350 9.117 -4.106 -2.793 -0.640 O6 FOX 5 1QL C5 C5 C 0 1 Y N N 29.458 4.893 10.370 6.344 0.433 -1.215 C5 FOX 6 1QL C8 C8 C 0 1 N N R 26.999 6.014 6.955 -0.444 -0.000 0.170 C8 FOX 7 1QL C15 C15 C 0 1 N N N 29.335 8.539 8.355 -3.698 -1.946 0.326 C15 FOX 8 1QL O5 O5 O 0 1 N N N 30.529 8.347 8.487 -4.087 -2.094 1.467 O5 FOX 9 1QL C13 C13 C 0 1 N N N 28.626 7.763 7.308 -2.779 -0.840 -0.002 C13 FOX 10 1QL C10 C10 C 0 1 N N N 28.850 7.992 5.905 -3.334 0.277 -0.412 C10 FOX 11 1QL C11 C11 C 0 1 N N N 29.793 8.866 5.466 -4.837 0.299 -0.520 C11 FOX 12 1QL C9 C9 C 0 1 N N N 27.928 7.333 4.883 -2.601 1.534 -0.781 C9 FOX 13 1QL S1 S1 S 0 1 N N N 26.350 6.874 5.563 -0.880 1.128 -1.193 S1 FOX 14 1QL C14 C14 C 0 1 N N N 25.486 4.180 7.085 1.008 -1.329 -1.338 C14 FOX 15 1QL O4 O4 O 0 1 N N N 26.284 3.394 6.660 0.015 -1.423 -2.018 O4 FOX 16 1QL C1 C1 C 0 1 N N S 25.909 5.410 7.802 0.965 -0.557 -0.044 C1 FOX 17 1QL O O O 0 1 N N N 24.806 6.284 8.054 1.304 -1.425 1.039 O FOX 18 1QL C C C 0 1 N N N 24.248 6.121 9.377 1.293 -0.788 2.319 C FOX 19 1QL N N N 0 1 N N N 26.641 4.987 9.005 1.923 0.549 -0.103 N FOX 20 1QL O1 O1 O 0 1 N N N 25.551 3.075 9.364 3.644 -0.838 0.093 O1 FOX 21 1QL C3 C3 C 0 1 N N N 27.266 3.455 10.830 4.234 1.422 -0.247 C3 FOX 22 1QL S S S 0 1 Y N N 28.488 4.617 12.781 6.589 0.720 1.296 S FOX 23 1QL C7 C7 C 0 1 Y N N 29.900 5.607 12.552 7.934 0.041 0.388 C7 FOX 24 1QL H1 H1 H 0 1 N N N 31.120 6.195 10.845 8.288 -0.415 -1.652 H1 FOX 25 1QL H2 H2 H 0 1 N N N 29.348 9.724 9.735 -4.708 -3.502 -0.377 H2 FOX 26 1QL H3 H3 H 0 1 N N N 29.616 4.759 9.310 5.956 0.433 -2.223 H3 FOX 27 1QL H4 H4 H 0 1 N N N 27.651 5.219 6.564 -0.493 0.530 1.122 H4 FOX 28 1QL H5 H5 H 0 1 N N N 30.054 9.787 6.007 -5.123 0.485 -1.555 H5 FOX 29 1QL H6 H6 H 0 1 N N N 30.635 8.567 4.824 -5.239 -0.662 -0.199 H6 FOX 30 1QL H7 H7 H 0 1 N N N 28.421 6.428 4.499 -3.083 1.992 -1.645 H7 FOX 31 1QL H8 H8 H 0 1 N N N 27.761 8.038 4.056 -2.620 2.230 0.058 H8 FOX 32 1QL H9 H9 H 0 1 N N N 24.432 3.989 6.943 1.927 -1.797 -1.657 H9 FOX 33 1QL H10 H10 H 0 1 N N N 23.407 6.818 9.509 2.013 0.030 2.324 H10 FOX 34 1QL H11 H11 H 0 1 N N N 23.891 5.088 9.499 0.296 -0.396 2.521 H11 FOX 35 1QL H12 H12 H 0 1 N N N 25.022 6.333 10.130 1.561 -1.513 3.088 H12 FOX 36 1QL H13 H13 H 0 1 N N N 27.340 5.602 9.370 1.606 1.464 -0.163 H13 FOX 37 1QL H14 H14 H 0 1 N N N 26.616 3.461 11.718 4.088 2.157 0.544 H14 FOX 38 1QL H15 H15 H 0 1 N N N 27.650 2.438 10.663 4.077 1.895 -1.216 H15 FOX 39 1QL H16 H16 H 0 1 N N N 30.420 6.128 13.343 8.876 -0.272 0.812 H16 FOX 40 1QL O2 O2 O 0 1 N N N ? ? ? -5.368 1.353 0.326 O2 FOX 41 1QL C16 C16 C 0 1 N N N ? ? ? -6.708 1.443 0.422 C16 FOX 42 1QL H17 H17 H 0 1 N N N 27.053 7.506 8.203 -1.118 -2.012 0.257 H17 FOX 43 1QL O3 O3 O 0 1 N N N ? ? ? -7.414 0.663 -0.185 O3 FOX 44 1QL N1 N1 N 0 1 N N N ? ? ? -7.265 2.399 1.191 N1 FOX 45 1QL H24 H24 H 0 1 N N N ? ? ? -6.701 3.022 1.676 H24 FOX 46 1QL H25 H25 H 0 1 N N N ? ? ? -8.231 2.464 1.260 H25 FOX 47 # # 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 1QL C9 S1 SING N N 1 1QL C9 C10 SING N N 2 1QL C11 C10 SING N N 3 1QL S1 C8 SING N N 4 1QL C10 C13 DOUB N N 5 1QL O4 C14 DOUB N N 6 1QL C8 N2 SING N N 7 1QL C8 C1 SING N N 8 1QL C14 C1 SING N N 9 1QL C13 N2 SING N N 10 1QL C13 C15 SING N N 11 1QL C1 O SING N N 12 1QL C1 N SING N N 13 1QL O C SING N N 14 1QL C15 O5 DOUB N N 15 1QL C15 O6 SING N N 16 1QL N C2 SING N N 17 1QL O1 C2 DOUB N N 18 1QL C2 C3 SING N N 19 1QL C5 C4 DOUB Y N 20 1QL C5 C6 SING Y N 21 1QL C3 C4 SING N N 22 1QL C4 S SING Y N 23 1QL C6 C7 DOUB Y N 24 1QL C7 S SING Y N 25 1QL C6 H1 SING N N 26 1QL O6 H2 SING N N 27 1QL C5 H3 SING N N 28 1QL C8 H4 SING N N 29 1QL C11 H5 SING N N 30 1QL C11 H6 SING N N 31 1QL C9 H7 SING N N 32 1QL C9 H8 SING N N 33 1QL C14 H9 SING N N 34 1QL C H10 SING N N 35 1QL C H11 SING N N 36 1QL C H12 SING N N 37 1QL N H13 SING N N 38 1QL C3 H14 SING N N 39 1QL C3 H15 SING N N 40 1QL C7 H16 SING N N 41 1QL C11 O2 SING N N 42 1QL O2 C16 SING N N 43 1QL N2 H17 SING N N 44 1QL C16 O3 DOUB N N 45 1QL C16 N1 SING N N 46 1QL N1 H24 SING N N 47 1QL N1 H25 SING N N 48 # # 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 1QL SMILES ACDLabs 12.01 "O=CC(OC)(NC(=O)Cc1sccc1)C2SCC(=C(N2)C(=O)O)COC(=O)N" 1QL InChI InChI 1.03 "InChI=1S/C16H19N3O7S2/c1-25-16(8-20,19-11(21)5-10-3-2-4-27-10)14-18-12(13(22)23)9(7-28-14)6-26-15(17)24/h2-4,8,14,18H,5-7H2,1H3,(H2,17,24)(H,19,21)(H,22,23)/t14-,16+/m1/s1" 1QL InChIKey InChI 1.03 IYZWSAWEHPQLHS-ZBFHGGJFSA-N 1QL SMILES_CANONICAL CACTVS 3.370 "CO[C@@](NC(=O)Cc1sccc1)(C=O)[C@@H]2NC(=C(COC(N)=O)CS2)C(O)=O" 1QL SMILES CACTVS 3.370 "CO[C](NC(=O)Cc1sccc1)(C=O)[CH]2NC(=C(COC(N)=O)CS2)C(O)=O" 1QL SMILES_CANONICAL "OpenEye OEToolkits" 1.7.6 "CO[C@@](C=O)([C@@H]1NC(=C(CS1)COC(=O)N)C(=O)O)NC(=O)Cc2cccs2" 1QL SMILES "OpenEye OEToolkits" 1.7.6 "COC(C=O)(C1NC(=C(CS1)COC(=O)N)C(=O)O)NC(=O)Cc2cccs2" # # 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 1QL "SYSTEMATIC NAME" ACDLabs 12.01 "(2R)-5-[(carbamoyloxy)methyl]-2-{(1S)-1-methoxy-2-oxo-1-[(thiophen-2-ylacetyl)amino]ethyl}-3,6-dihydro-2H-1,3-thiazine-4-carboxylic acid" 1QL "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.7.6 "(2R)-5-(aminocarbonyloxymethyl)-2-[(1S)-1-methoxy-2-oxidanylidene-1-(2-thiophen-2-ylethanoylamino)ethyl]-3,6-dihydro-2H-1,3-thiazine-4-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 1QL "Create component" 2013-04-26 RCSB 1QL "Initial release" 2018-09-12 RCSB 1QL "Modify synonyms" 2021-03-13 RCSB # _pdbx_chem_comp_synonyms.ordinal 1 _pdbx_chem_comp_synonyms.comp_id 1QL _pdbx_chem_comp_synonyms.name "Cefoxitin, bound form" _pdbx_chem_comp_synonyms.provenance PDB _pdbx_chem_comp_synonyms.type ? ##