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                    2024-09-27 
_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 
_chem_comp.pdbx_pcm                              Y 
# 
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.pdbx_backbone_atom_flag 
_chem_comp_atom.pdbx_n_terminal_atom_flag 
_chem_comp_atom.pdbx_c_terminal_atom_flag 
_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 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 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 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 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 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 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 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 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 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 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 N N N -9.363  -10.728 5.097  0.388  0.147  0.121  CAK  9EP 11 
9EP CAL  CAL  C 0 1 N N R N N N -10.404 -11.806 4.705  -1.002 0.761  -0.061 CAL  9EP 12 
9EP NAM  NAM  N 0 1 N N N 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 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 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 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 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 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 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 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 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 N 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 N 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 N 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 N 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 N 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 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 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 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 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 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 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 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 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 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 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 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 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 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 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 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 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 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 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 
9EP "Modify PCM"           2024-09-27 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         ? 
# 
_pdbx_chem_comp_pcm.pcm_id                             1 
_pdbx_chem_comp_pcm.comp_id                            9EP 
_pdbx_chem_comp_pcm.modified_residue_id                SER 
_pdbx_chem_comp_pcm.type                               None 
_pdbx_chem_comp_pcm.category                           "Covalent chemical modification" 
_pdbx_chem_comp_pcm.position                           "Amino-acid side chain" 
_pdbx_chem_comp_pcm.polypeptide_position               "Any position" 
_pdbx_chem_comp_pcm.comp_id_linking_atom               CAO 
_pdbx_chem_comp_pcm.modified_residue_id_linking_atom   OG 
_pdbx_chem_comp_pcm.uniprot_specific_ptm_accession     ? 
_pdbx_chem_comp_pcm.uniprot_generic_ptm_accession      ? 
# 
