data_9EP # _chem_comp.id 9EP _chem_comp.name ;(2R)-5-[(acetyloxy)methyl]-2-{(1R)-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 H18 N2 O6 S2" _chem_comp.mon_nstd_parent_comp_id ? _chem_comp.pdbx_synonyms "Cephalotin, bound form" _chem_comp.pdbx_formal_charge 0 _chem_comp.pdbx_initial_date 2010-06-28 _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 398.454 _chem_comp.one_letter_code ? _chem_comp.three_letter_code 9EP _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 3NDE _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 9EP CAA CAA C 0 1 N N N -7.770 -6.869 -0.333 6.603 -1.569 0.223 CAA 9EP 1 9EP OAB OAB O 0 1 N N N -7.765 -7.682 0.794 5.280 -1.344 0.241 OAB 9EP 2 9EP CAC CAC C 0 1 N N N -8.609 -7.482 1.873 4.818 -0.082 -0.309 CAC 9EP 3 9EP CAD CAD C 0 1 N N N -8.815 -8.608 2.928 3.312 -0.053 -0.306 CAD 9EP 4 9EP SAE SAE S 0 1 N N N -7.787 -10.873 4.232 0.913 -0.669 -1.421 SAE 9EP 5 9EP CAF CAF C 0 1 N N N -9.687 -8.444 4.013 2.733 0.960 0.296 CAF 9EP 6 9EP CAG CAG C 0 1 N N N -10.503 -7.195 4.265 3.629 1.950 0.920 CAG 9EP 7 9EP OAH OAH O 0 1 N N N -10.481 -6.253 3.468 3.975 2.934 0.297 OAH 9EP 8 9EP OAI OAI O 0 1 N N N -11.163 -7.203 5.310 4.066 1.764 2.182 OAI 9EP 9 9EP NAJ NAJ N 0 1 N N N -9.925 -9.379 4.948 1.370 1.202 0.410 NAJ 9EP 10 9EP CAK CAK C 0 1 N N R -9.363 -10.728 5.097 0.388 0.147 0.121 CAK 9EP 11 9EP CAL CAL C 0 1 N N R -10.404 -11.806 4.705 -1.002 0.761 -0.061 CAL 9EP 12 9EP NAM NAM N 0 1 N N N -10.493 -12.213 3.292 -1.961 -0.294 -0.400 NAM 9EP 13 9EP CAN CAN C 0 1 N N N -9.844 -13.302 2.873 -3.269 -0.130 -0.123 CAN 9EP 14 9EP CAO CAO C 0 1 N N N -11.761 -11.327 5.182 -0.961 1.778 -1.172 CAO 9EP 15 9EP OAP OAP O 0 1 N N N -12.526 -10.677 4.209 -1.660 1.636 -2.147 OAP 9EP 16 9EP CAQ CAQ C 0 1 N N N -7.247 -7.465 -1.649 7.156 -2.857 0.776 CAQ 9EP 17 9EP CAR CAR C 0 1 N N N -8.067 -9.923 2.692 2.603 -1.183 -0.996 CAR 9EP 18 9EP OAS OAS O 0 1 N N N -8.157 -5.693 -0.315 7.350 -0.742 -0.243 OAS 9EP 19 9EP CAT CAT C 0 1 N N N -10.049 -13.664 1.399 -4.255 -1.215 -0.472 CAT 9EP 20 9EP OAU OAU O 0 1 N N N -9.135 -14.000 3.607 -3.654 0.892 0.406 OAU 9EP 21 9EP CAV CAV C 0 1 Y N N -9.174 -12.766 0.529 -5.641 -0.785 -0.062 CAV 9EP 22 9EP CAW CAW C 0 1 Y N N -7.840 -12.662 0.480 -6.497 -0.115 -0.833 CAW 9EP 23 9EP SAX SAX S 0 1 Y N N -9.806 -11.686 -0.583 -6.377 -1.099 1.504 SAX 9EP 24 9EP CAY CAY C 0 1 Y N N -8.297 -11.091 -1.111 -7.848 -0.270 1.012 CAY 9EP 25 9EP CAZ CAZ C 0 1 Y N N -7.366 -11.751 -0.409 -7.715 0.171 -0.240 CAZ 9EP 26 9EP HAC HAC H 0 1 N N N -8.225 -6.606 2.416 5.199 0.740 0.297 HAC 9EP 27 9EP HACA HACA H 0 0 N N N -9.602 -7.251 1.459 5.181 0.023 -1.332 HACA 9EP 28 9EP HNAJ HNAJ H 0 0 N N N -9.701 -8.925 5.810 1.062 2.080 0.685 HNAJ 9EP 29 9EP HAK HAK H 0 1 N N N -9.116 -10.883 6.158 0.372 -0.576 0.937 HAK 9EP 30 9EP HAL HAL H 0 1 N N N -10.159 -12.704 5.291 -1.309 1.247 0.865 HAL 9EP 31 9EP HNAM HNAM H 0 0 N N N -11.038 -11.675 2.649 -1.653 -1.111 -0.823 HNAM 9EP 32 9EP HAO HAO H 0 1 N N N -12.109 -11.476 6.193 -0.306 2.633 -1.097 HAO 9EP 33 9EP HAQ HAQ H 0 1 N N N -7.296 -6.704 -2.442 6.337 -3.475 1.145 HAQ 9EP 34 9EP HAQA HAQA H 0 0 N N N -6.204 -7.789 -1.516 7.690 -3.391 -0.009 HAQA 9EP 35 9EP HAQB HAQB H 0 0 N N N -7.866 -8.329 -1.932 7.841 -2.636 1.595 HAQB 9EP 36 9EP HAR HAR H 0 1 N N N -8.657 -10.542 2.000 3.143 -1.450 -1.904 HAR 9EP 37 9EP HARA HARA H 0 0 N N N -7.091 -9.695 2.239 2.561 -2.046 -0.331 HARA 9EP 38 9EP HAT HAT H 0 1 N N N -9.770 -14.716 1.237 -4.234 -1.393 -1.547 HAT 9EP 39 9EP HATA HATA H 0 0 N N N -11.106 -13.519 1.129 -3.988 -2.131 0.054 HATA 9EP 40 9EP HAW HAW H 0 1 N N N -7.189 -13.259 1.102 -6.259 0.183 -1.844 HAW 9EP 41 9EP HAY HAY H 0 1 N N N -8.126 -10.333 -1.861 -8.726 -0.141 1.627 HAY 9EP 42 9EP HAZ HAZ H 0 1 N N N -6.309 -11.571 -0.541 -8.499 0.709 -0.753 HAZ 9EP 43 9EP HOAI HOAI H 0 0 N N N -11.637 -6.384 5.392 4.652 2.440 2.548 HOAI 9EP 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 9EP CAA OAB SING N N 1 9EP CAA CAQ SING N N 2 9EP CAA OAS DOUB N N 3 9EP OAB CAC SING N N 4 9EP CAC CAD SING N N 5 9EP CAD CAF DOUB N N 6 9EP CAD CAR SING N N 7 9EP SAE CAK SING N N 8 9EP SAE CAR SING N N 9 9EP CAF CAG SING N N 10 9EP CAF NAJ SING N N 11 9EP CAG OAH DOUB N N 12 9EP CAG OAI SING N N 13 9EP NAJ CAK SING N N 14 9EP CAK CAL SING N N 15 9EP CAL NAM SING N N 16 9EP CAL CAO SING N N 17 9EP NAM CAN SING N N 18 9EP CAN CAT SING N N 19 9EP CAN OAU DOUB N N 20 9EP CAO OAP DOUB N N 21 9EP CAT CAV SING N N 22 9EP CAV CAW DOUB Y N 23 9EP CAV SAX SING Y N 24 9EP CAW CAZ SING Y N 25 9EP SAX CAY SING Y N 26 9EP CAY CAZ DOUB Y N 27 9EP CAC HAC SING N N 28 9EP CAC HACA SING N N 29 9EP NAJ HNAJ SING N N 30 9EP CAK HAK SING N N 31 9EP CAL HAL SING N N 32 9EP NAM HNAM SING N N 33 9EP CAO HAO SING N N 34 9EP CAQ HAQ SING N N 35 9EP CAQ HAQA SING N N 36 9EP CAQ HAQB SING N N 37 9EP CAR HAR SING N N 38 9EP CAR HARA SING N N 39 9EP CAT HAT SING N N 40 9EP CAT HATA SING N N 41 9EP CAW HAW SING N N 42 9EP CAY HAY SING N N 43 9EP CAZ HAZ SING N N 44 9EP OAI HOAI SING N N 45 # # 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 9EP SMILES ACDLabs 12.01 "O=CC(NC(=O)Cc1sccc1)C2SCC(=C(N2)C(=O)O)COC(=O)C" 9EP InChI InChI 1.03 "InChI=1S/C16H18N2O6S2/c1-9(20)24-7-10-8-26-15(18-14(10)16(22)23)12(6-19)17-13(21)5-11-3-2-4-25-11/h2-4,6,12,15,18H,5,7-8H2,1H3,(H,17,21)(H,22,23)/t12-,15-/m1/s1" 9EP InChIKey InChI 1.03 MXSQWXIVWHYOCY-IUODEOHRSA-N 9EP SMILES_CANONICAL CACTVS 3.370 "CC(=O)OCC1=C(N[C@H](SC1)[C@H](NC(=O)Cc2sccc2)C=O)C(O)=O" 9EP SMILES CACTVS 3.370 "CC(=O)OCC1=C(N[CH](SC1)[CH](NC(=O)Cc2sccc2)C=O)C(O)=O" 9EP SMILES_CANONICAL "OpenEye OEToolkits" 1.7.6 "CC(=O)OCC1=C(N[C@H](SC1)[C@@H](C=O)NC(=O)Cc2cccs2)C(=O)O" 9EP SMILES "OpenEye OEToolkits" 1.7.6 "CC(=O)OCC1=C(NC(SC1)C(C=O)NC(=O)Cc2cccs2)C(=O)O" # # 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 9EP "SYSTEMATIC NAME" ACDLabs 12.01 "(2R)-5-[(acetyloxy)methyl]-2-{(1R)-2-oxo-1-[(thiophen-2-ylacetyl)amino]ethyl}-3,6-dihydro-2H-1,3-thiazine-4-carboxylic acid" 9EP "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.7.6 "(2R)-5-(acetyloxymethyl)-2-[(1R)-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 9EP "Create component" 2010-06-28 RCSB 9EP "Modify aromatic_flag" 2011-06-04 RCSB 9EP "Modify descriptor" 2011-06-04 RCSB 9EP "Modify synonyms" 2012-03-22 RCSB 9EP "Modify synonyms" 2020-06-05 PDBE # _pdbx_chem_comp_synonyms.ordinal 1 _pdbx_chem_comp_synonyms.comp_id 9EP _pdbx_chem_comp_synonyms.name "Cephalotin, bound form" _pdbx_chem_comp_synonyms.provenance ? _pdbx_chem_comp_synonyms.type ? ##