data_A1B93
# 
_chem_comp.id                                    A1B93 
_chem_comp.name                                  "(2S,3R,4R)-4-({(3S,5S)-5-[(3-carboxyphenyl)carbamoyl]pyrrolidin-3-yl}sulfanyl)-2-[(2S,3R)-3-hydroxy-1-oxobutan-2-yl]-3-methyl-3,4-dihydro-2H-pyrrole-5-carboxylic acid" 
_chem_comp.type                                  non-polymer 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C22 H27 N3 O7 S" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         "Ertapenem, bound form, post-isomerized, delta-1(R) isomer" 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2025-04-16 
_chem_comp.pdbx_modified_date                    2025-12-17 
_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                        477.531 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     A1B93 
_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        9MTW 
_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_n_terminal_atom_flag 
_chem_comp_atom.pdbx_backbone_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 
A1B93 C2  C1  C 0 1 N N R N N N 8.145  28.684 10.467 -2.856 -0.379 -0.820 C2  A1B93 1  
A1B93 C5  C2  C 0 1 N N S N N N 6.456  28.825 12.218 -5.093 0.419  -0.606 C5  A1B93 2  
A1B93 C6  C3  C 0 1 N N S N N N 6.225  27.589 13.065 -5.929 1.207  0.405  C6  A1B93 3  
A1B93 C1  C4  C 0 1 N N R N N N 7.932  29.082 11.912 -3.638 0.942  -0.622 C1  A1B93 4  
A1B93 C11 C5  C 0 1 N N N N N N 8.900  28.358 12.839 -3.274 1.605  0.708  C11 A1B93 5  
A1B93 C3  C6  C 0 1 N N N N N N 6.764  28.483 9.972  -3.803 -1.439 -0.302 C3  A1B93 6  
A1B93 C7  C7  C 0 1 N N N N N N 5.033  26.704 12.463 -5.456 0.894  1.801  C7  A1B93 7  
A1B93 CD2 C8  C 0 1 Y N N N N N 11.211 25.003 13.603 5.447  1.322  0.376  CD2 A1B93 8  
A1B93 CE2 C9  C 0 1 Y N N N N N 9.906  24.952 14.061 6.436  2.249  0.685  CE2 A1B93 9  
A1B93 CE3 C10 C 0 1 Y N N N N N 12.258 24.751 14.481 5.767  -0.022 0.264  CE3 A1B93 10 
A1B93 CZ2 C11 C 0 1 Y N N N N N 9.644  24.657 15.388 7.740  1.835  0.882  CZ2 A1B93 11 
A1B93 CZ3 C12 C 0 1 Y N N N N N 11.993 24.459 15.808 7.083  -0.440 0.464  CZ3 A1B93 12 
A1B93 CH2 C13 C 0 1 Y N N N N N 10.686 24.407 16.263 8.070  0.500  0.773  CH2 A1B93 13 
A1B93 C1A C14 C 0 1 N N S N N N 10.147 27.166 9.226  -0.311 0.875  -0.710 C1A A1B93 14 
A1B93 C2A C15 C 0 1 N N N N N N 10.563 25.786 8.787  0.261  0.305  -2.032 C2A A1B93 15 
A1B93 C31 C16 C 0 1 N N N N N N 6.487  28.204 8.566  -3.403 -2.825 0.039  C31 A1B93 16 
A1B93 C41 C17 C 0 1 N N N N N N 13.110 24.184 16.761 7.433  -1.870 0.347  C41 A1B93 17 
A1B93 C4A C18 C 0 1 N N N N N N 11.361 27.756 9.904  0.985  1.183  0.085  C4A A1B93 18 
A1B93 C5A C19 C 0 1 N N S N N N 12.157 26.563 10.400 1.964  1.650  -1.013 C5A A1B93 19 
A1B93 C61 C20 C 0 1 N N R N N N 5.788  27.987 14.473 -7.401 0.814  0.265  C61 A1B93 20 
A1B93 C62 C21 C 0 1 N N N N N N 5.652  26.746 15.355 -7.882 1.131  -1.152 C62 A1B93 21 
A1B93 C6A C22 C 0 1 N N N N N N 11.976 26.433 11.882 3.346  1.125  -0.724 C6A A1B93 22 
A1B93 N3A N1  N 0 1 N N N N N N 11.642 25.371 9.700  1.477  1.104  -2.293 N3A A1B93 23 
A1B93 N4  N2  N 0 1 N N N N N N 5.905  28.549 10.885 -4.989 -0.986 -0.196 N4  A1B93 24 
A1B93 N7A N3  N 0 1 N N N N N N 11.445 25.286 12.308 4.127  1.745  0.183  N7A A1B93 25 
A1B93 O31 O1  O 0 1 N N N N N N 5.673  27.314 8.264  -4.296 -3.666 0.596  O31 A1B93 26 
A1B93 O32 O2  O 0 1 N N N N N N 7.103  28.859 7.700  -2.271 -3.202 -0.183 O32 A1B93 27 
A1B93 O42 O3  O 0 1 N N N N N N 12.824 23.815 17.917 8.705  -2.271 0.540  O42 A1B93 28 
A1B93 O43 O4  O 0 1 N N N N N N 14.288 24.330 16.376 6.574  -2.685 0.078  O43 A1B93 29 
A1B93 O62 O5  O 0 1 N N N N N N 6.671  28.951 15.061 -7.546 -0.586 0.515  O62 A1B93 30 
A1B93 O6A O6  O 0 1 N N N N N N 12.309 27.358 12.603 3.756  0.143  -1.306 O6A A1B93 31 
A1B93 O7  O7  O 0 1 N N N N N N 5.482  25.754 11.820 -5.038 1.778  2.509  O7  A1B93 32 
A1B93 S21 S1  S 0 1 N N N N N N 8.851  27.076 10.402 -1.322 -0.363 0.148  S21 A1B93 33 
A1B93 H1  H1  H 0 1 N N N N N N 8.746  29.398 9.885  -2.640 -0.542 -1.875 H1  A1B93 34 
A1B93 H2  H2  H 0 1 N N N N N N 5.991  29.710 12.676 -5.533 0.494  -1.600 H2  A1B93 35 
A1B93 H3  H3  H 0 1 N N N N N N 7.140  26.980 13.110 -5.819 2.274  0.215  H3  A1B93 36 
A1B93 H4  H4  H 0 1 N N N N N N 8.116  30.163 12.002 -3.474 1.624  -1.457 H4  A1B93 37 
A1B93 H5  H5  H 0 1 N N N N N N 8.717  28.671 13.878 -2.248 1.969  0.664  H5  A1B93 38 
A1B93 H6  H6  H 0 1 N N N N N N 8.749  27.272 12.751 -3.948 2.441  0.894  H6  A1B93 39 
A1B93 H7  H7  H 0 1 N N N N N N 9.934  28.608 12.558 -3.367 0.877  1.514  H7  A1B93 40 
A1B93 H8  H8  H 0 1 N Y N N N N 3.982  26.911 12.602 -5.491 -0.121 2.168  H8  A1B93 41 
A1B93 H10 H10 H 0 1 N N N N N N 9.089  25.143 13.381 6.184  3.295  0.771  H10 A1B93 42 
A1B93 H11 H11 H 0 1 N N N N N N 13.278 24.783 14.128 5.000  -0.743 0.025  H11 A1B93 43 
A1B93 H12 H12 H 0 1 N N N N N N 8.624  24.622 15.741 8.504  2.560  1.122  H12 A1B93 44 
A1B93 H13 H13 H 0 1 N N N N N N 10.481 24.172 17.297 9.090  0.181  0.927  H13 A1B93 45 
A1B93 H14 H14 H 0 1 N N N N N N 9.812  27.782 8.379  -0.883 1.785  -0.892 H14 A1B93 46 
A1B93 H15 H15 H 0 1 N N N N N N 9.714  25.091 8.860  0.517  -0.748 -1.912 H15 A1B93 47 
A1B93 H16 H16 H 0 1 N N N N N N 10.929 25.810 7.750  -0.457 0.431  -2.842 H16 A1B93 48 
A1B93 H17 H17 H 0 1 N N N N N N 11.954 28.345 9.189  0.812  1.978  0.811  H17 A1B93 49 
A1B93 H18 H18 H 0 1 N N N N N N 11.060 28.396 10.746 1.357  0.285  0.577  H18 A1B93 50 
A1B93 H19 H19 H 0 1 N N N N N N 13.222 26.708 10.166 1.982  2.739  -1.054 H19 A1B93 51 
A1B93 H20 H20 H 0 1 N N N N N N 4.788  28.438 14.389 -7.997 1.375  0.985  H20 A1B93 52 
A1B93 H21 H21 H 0 1 N N N N N N 5.337  27.046 16.365 -7.286 0.570  -1.872 H21 A1B93 53 
A1B93 H22 H22 H 0 1 N N N N N N 4.900  26.070 14.923 -8.931 0.851  -1.251 H22 A1B93 54 
A1B93 H23 H23 H 0 1 N N N N N N 6.621  26.229 15.412 -7.772 2.199  -1.342 H23 A1B93 55 
A1B93 H24 H24 H 0 1 N N N N N N 11.285 24.717 10.367 2.188  0.545  -2.741 H24 A1B93 56 
A1B93 H26 H26 H 0 1 N N N N N N 11.207 24.596 11.625 3.774  2.486  0.701  H26 A1B93 57 
A1B93 H27 H27 H 0 1 N N N N N N 5.620  27.240 7.318  -3.989 -4.560 0.801  H27 A1B93 58 
A1B93 H28 H28 H 0 1 N N N N N N 13.623 23.677 18.412 8.885  -3.217 0.454  H28 A1B93 59 
A1B93 H29 H29 H 0 1 N N N N N N 6.365  29.171 15.933 -8.456 -0.906 0.444  H29 A1B93 60 
# 
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 
A1B93 O32 C31 DOUB N N 1  
A1B93 O31 C31 SING N N 2  
A1B93 C31 C3  SING N N 3  
A1B93 C2A C1A SING N N 4  
A1B93 C2A N3A SING N N 5  
A1B93 C1A C4A SING N N 6  
A1B93 C1A S21 SING N N 7  
A1B93 N3A C5A SING N N 8  
A1B93 C4A C5A SING N N 9  
A1B93 C3  C2  SING N N 10 
A1B93 C3  N4  DOUB N N 11 
A1B93 C5A C6A SING N N 12 
A1B93 S21 C2  SING N N 13 
A1B93 C2  C1  SING N N 14 
A1B93 N4  C5  SING N N 15 
A1B93 O7  C7  DOUB N N 16 
A1B93 C6A N7A SING N N 17 
A1B93 C6A O6A DOUB N N 18 
A1B93 C1  C5  SING N N 19 
A1B93 C1  C11 SING N N 20 
A1B93 C5  C6  SING N N 21 
A1B93 N7A CD2 SING N N 22 
A1B93 C7  C6  SING N N 23 
A1B93 C6  C61 SING N N 24 
A1B93 CD2 CE2 DOUB Y N 25 
A1B93 CD2 CE3 SING Y N 26 
A1B93 CE2 CZ2 SING Y N 27 
A1B93 C61 O62 SING N N 28 
A1B93 C61 C62 SING N N 29 
A1B93 CE3 CZ3 DOUB Y N 30 
A1B93 CZ2 CH2 DOUB Y N 31 
A1B93 CZ3 CH2 SING Y N 32 
A1B93 CZ3 C41 SING N N 33 
A1B93 O43 C41 DOUB N N 34 
A1B93 C41 O42 SING N N 35 
A1B93 C2  H1  SING N N 36 
A1B93 C5  H2  SING N N 37 
A1B93 C6  H3  SING N N 38 
A1B93 C1  H4  SING N N 39 
A1B93 C11 H5  SING N N 40 
A1B93 C11 H6  SING N N 41 
A1B93 C11 H7  SING N N 42 
A1B93 C7  H8  SING N N 43 
A1B93 CE2 H10 SING N N 44 
A1B93 CE3 H11 SING N N 45 
A1B93 CZ2 H12 SING N N 46 
A1B93 CH2 H13 SING N N 47 
A1B93 C1A H14 SING N N 48 
A1B93 C2A H15 SING N N 49 
A1B93 C2A H16 SING N N 50 
A1B93 C4A H17 SING N N 51 
A1B93 C4A H18 SING N N 52 
A1B93 C5A H19 SING N N 53 
A1B93 C61 H20 SING N N 54 
A1B93 C62 H21 SING N N 55 
A1B93 C62 H22 SING N N 56 
A1B93 C62 H23 SING N N 57 
A1B93 N3A H24 SING N N 58 
A1B93 N7A H26 SING N N 59 
A1B93 O31 H27 SING N N 60 
A1B93 O42 H28 SING N N 61 
A1B93 O62 H29 SING N N 62 
# 
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 
A1B93 SMILES           ACDLabs              14.52   "O=C(O)c1cc(ccc1)NC(=O)C1CC(SC2C(C)C(N=C2C(=O)O)C(C=O)C(C)O)CN1"                                                                                                                                                                
A1B93 InChI            InChI                1.06    "InChI=1S/C22H27N3O7S/c1-10-17(15(9-26)11(2)27)25-18(22(31)32)19(10)33-14-7-16(23-8-14)20(28)24-13-5-3-4-12(6-13)21(29)30/h3-6,9-11,14-17,19,23,27H,7-8H2,1-2H3,(H,24,28)(H,29,30)(H,31,32)/t10-,11-,14+,15-,16+,17-,19-/m1/s1" 
A1B93 InChIKey         InChI                1.06    RALHTEQYPKBGFO-RNGRAGBPSA-N                                                                                                                                                                                                     
A1B93 SMILES_CANONICAL CACTVS               3.385   "C[C@@H](O)[C@@H](C=O)[C@@H]1N=C([C@H](S[C@@H]2CN[C@@H](C2)C(=O)Nc3cccc(c3)C(O)=O)[C@@H]1C)C(O)=O"                                                                                                                              
A1B93 SMILES           CACTVS               3.385   "C[CH](O)[CH](C=O)[CH]1N=C([CH](S[CH]2CN[CH](C2)C(=O)Nc3cccc(c3)C(O)=O)[CH]1C)C(O)=O"                                                                                                                                           
A1B93 SMILES_CANONICAL "OpenEye OEToolkits" 3.1.0.0 "C[C@H]1[C@H](C(=N[C@H]1[C@H](C=O)[C@@H](C)O)C(=O)O)S[C@H]2C[C@H](NC2)C(=O)Nc3cccc(c3)C(=O)O"                                                                                                                                   
A1B93 SMILES           "OpenEye OEToolkits" 3.1.0.0 "CC1C(C(=NC1C(C=O)C(C)O)C(=O)O)SC2CC(NC2)C(=O)Nc3cccc(c3)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 
A1B93 "SYSTEMATIC NAME" ACDLabs              14.52   "(2S,3R,4R)-4-({(3S,5S)-5-[(3-carboxyphenyl)carbamoyl]pyrrolidin-3-yl}sulfanyl)-2-[(2S,3R)-3-hydroxy-1-oxobutan-2-yl]-3-methyl-3,4-dihydro-2H-pyrrole-5-carboxylic acid"                                   
A1B93 "SYSTEMATIC NAME" "OpenEye OEToolkits" 3.1.0.0 "(2~{S},3~{R},4~{R})-4-[(3~{S},5~{S})-5-[(3-carboxyphenyl)carbamoyl]pyrrolidin-3-yl]sulfanyl-3-methyl-2-[(2~{S},3~{R})-3-oxidanyl-1-oxidanylidene-butan-2-yl]-3,4-dihydro-2~{H}-pyrrole-5-carboxylic acid" 
# 
loop_
_pdbx_chem_comp_synonyms.ordinal 
_pdbx_chem_comp_synonyms.comp_id 
_pdbx_chem_comp_synonyms.name 
_pdbx_chem_comp_synonyms.provenance 
_pdbx_chem_comp_synonyms.type 
1 A1B93 "ertapenem, bound form, post-isomerized, delta-1(R) isomer"                                                                                                              AUTHOR ?     
2 A1B93 "(2S,3R,4R)-4-({(3S,5S)-5-[(3-carboxyphenyl)carbamoyl]pyrrolidin-3-yl}sulfanyl)-2-[(2S,3R)-3-hydroxy-1-oxobutan-2-yl]-3-methyl-3,4-dihydro-2H-pyrrole-5-carboxylic acid" PDB    IUPAC 
# 
_pdbx_chem_comp_pcm.pcm_id                             1 
_pdbx_chem_comp_pcm.comp_id                            A1B93 
_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               C7 
_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      ? 
# 
loop_
_pdbx_chem_comp_audit.comp_id 
_pdbx_chem_comp_audit.action_type 
_pdbx_chem_comp_audit.date 
_pdbx_chem_comp_audit.processing_site 
A1B93 "Create component" 2025-04-16 RCSB 
A1B93 "Modify PCM"       2025-04-17 RCSB 
A1B93 "Initial release"  2025-04-23 RCSB 
A1B93 "Modify name"      2025-12-15 PDBE 
A1B93 "Modify name"      2025-12-17 RCSB 
# 
