data_AXL
# 
_chem_comp.id                                    AXL 
_chem_comp.name                                  "2-{1-[2-AMINO-2-(4-HYDROXY-PHENYL)-ACETYLAMINO]-2-OXO-ETHYL}-5,5-DIMETHYL-THIAZOLIDINE-4-CARBOXYLIC ACID" 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C16 H21 N3 O5 S" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         "AMOXICILLIN, bound form" 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2002-05-07 
_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                        367.420 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     AXL 
_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        1LL9 
_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 
AXL C1   C1   C 0 1 N N N N N N 77.460 4.104 28.706 -1.134 -2.730 0.550  C1   AXL 1  
AXL O1   O1   O 0 1 N N N N N N 78.025 3.256 28.071 -0.640 -3.490 -0.248 O1   AXL 2  
AXL C2   C2   C 0 1 N N R N N N 77.928 5.440 29.336 -0.513 -1.378 0.788  C2   AXL 3  
AXL C3   C3   C 0 1 N N R N N N 78.525 6.265 28.135 -1.528 -0.284 0.449  C3   AXL 4  
AXL S4   S4   S 0 1 N N N N N N 78.960 7.934 28.606 -2.086 -0.415 -1.301 S4   AXL 5  
AXL C5   C5   C 0 1 N N N N N N 80.679 7.851 27.924 -3.727 0.354  -0.999 C5   AXL 6  
AXL C51  C51  C 0 1 N N N N N N 81.583 8.629 28.879 -4.826 -0.416 -1.735 C51  AXL 7  
AXL C52  C52  C 0 1 N N N N N N 80.671 8.493 26.551 -3.720 1.822  -1.429 C52  AXL 8  
AXL C6   C6   C 0 1 N N S N N N 81.043 6.319 27.913 -3.906 0.232  0.526  C6   AXL 9  
AXL C61  C61  C 0 1 N N N N N N 82.113 5.841 26.879 -3.981 1.615  1.119  C61  AXL 10 
AXL O62  O62  O 0 1 N N N N N N 81.731 5.248 25.858 -5.130 2.307  1.064  O62  AXL 11 
AXL O63  O63  O 0 1 N N N N N N 83.307 6.085 27.136 -3.007 2.102  1.643  O63  AXL 12 
AXL N7   N7   N 0 1 N N N N N N 79.785 5.567 27.853 -2.812 -0.501 1.171  N7   AXL 13 
AXL N8   N8   N 0 1 N N N N N N 78.796 5.050 30.417 0.670  -1.228 -0.064 N8   AXL 14 
AXL C9   C9   C 0 1 N N N N N N 79.138 5.847 31.462 1.861  -1.704 0.348  C9   AXL 15 
AXL O91  O91  O 0 1 N N N N N N 78.611 6.929 31.704 1.954  -2.257 1.424  O91  AXL 16 
AXL C10  C10  C 0 1 N N R N N N 80.256 5.300 32.336 3.078  -1.549 -0.527 C10  AXL 17 
AXL N11  N11  N 0 1 N N N N N N 79.863 5.478 33.763 4.100  -2.523 -0.122 N11  AXL 18 
AXL C12  C12  C 0 1 Y N N N N N 81.668 5.803 31.973 3.628  -0.154 -0.382 C12  AXL 19 
AXL C13  C13  C 0 1 Y N N N N N 82.126 7.039 32.491 3.345  0.803  -1.339 C13  AXL 20 
AXL C14  C14  C 0 1 Y N N N N N 83.417 7.512 32.164 3.848  2.083  -1.207 C14  AXL 21 
AXL C15  C15  C 0 1 Y N N N N N 84.268 6.735 31.308 4.637  2.408  -0.114 C15  AXL 22 
AXL C16  C16  C 0 1 Y N N N N N 83.803 5.524 30.807 4.919  1.446  0.845  C16  AXL 23 
AXL C17  C17  C 0 1 Y N N N N N 82.536 5.045 31.119 4.409  0.169  0.712  C17  AXL 24 
AXL O18  O18  O 0 1 N N N N N N 85.539 7.077 30.913 5.133  3.667  0.018  O18  AXL 25 
AXL HC1  HC1  H 0 1 N N N N N N 76.414 3.893 28.872 -2.024 -3.018 1.090  HC1  AXL 26 
AXL HC2  HC2  H 0 1 N N N N N N 77.050 5.976 29.726 -0.221 -1.291 1.834  HC2  AXL 27 
AXL HC3  HC3  H 0 1 N N N N N N 77.837 6.298 27.277 -1.120 0.705  0.658  HC3  AXL 28 
AXL H511 H511 H 0 0 N N N N N N 82.618 8.603 28.507 -4.831 -1.452 -1.398 H511 AXL 29 
AXL H512 H512 H 0 0 N N N N N N 81.241 9.673 28.939 -5.793 0.040  -1.523 H512 AXL 30 
AXL H513 H513 H 0 0 N N N N N N 81.541 8.171 29.878 -4.636 -0.384 -2.808 H513 AXL 31 
AXL H521 H521 H 0 0 N N N N N N 81.684 8.457 26.123 -3.515 1.888  -2.497 H521 AXL 32 
AXL H522 H522 H 0 0 N N N N N N 79.976 7.948 25.896 -4.693 2.267  -1.218 H522 AXL 33 
AXL H523 H523 H 0 0 N N N N N N 80.347 9.541 26.638 -2.949 2.359  -0.877 H523 AXL 34 
AXL HC6  HC6  H 0 1 N N N N N N 81.480 6.117 28.902 -4.843 -0.288 0.729  HC6  AXL 35 
AXL H62O H62O H 0 0 N N N N N N 82.483 5.020 25.324 -5.130 3.190  1.458  H62O AXL 36 
AXL HN7  HN7  H 0 1 N N N N N N 79.859 4.818 28.512 -3.027 -1.484 1.240  HN7  AXL 37 
AXL HN8  HN8  H 0 1 N N N N N N 79.175 4.125 30.397 0.595  -0.785 -0.924 HN8  AXL 38 
AXL H10  H10  H 0 1 N N N N N N 80.273 4.215 32.157 2.802  -1.724 -1.567 H10  AXL 39 
AXL H111 H111 H 0 0 N N N N N N 80.587 5.124 34.355 4.373  -2.382 0.839  H111 AXL 40 
AXL H112 H112 H 0 0 N N N N N N 79.724 6.450 33.952 3.779  -3.468 -0.271 H112 AXL 41 
AXL H13  H13  H 0 1 N N N N N N 81.487 7.622 33.138 2.731  0.549  -2.190 H13  AXL 42 
AXL H14  H14  H 0 1 N N N N N N 83.763 8.456 32.557 3.627  2.830  -1.956 H14  AXL 43 
AXL H16  H16  H 0 1 N N N N N N 84.442 4.941 30.160 5.533  1.697  1.698  H16  AXL 44 
AXL H17  H17  H 0 1 N N N N N N 82.204 4.099 30.717 4.625  -0.578 1.461  H17  AXL 45 
AXL H18O H18O H 0 0 N N N N N N 85.889 6.398 30.349 4.555  4.268  0.506  H18O AXL 46 
# 
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 
AXL C1  O1   DOUB N N 1  
AXL C1  C2   SING N N 2  
AXL C1  HC1  SING N N 3  
AXL C2  C3   SING N N 4  
AXL C2  N8   SING N N 5  
AXL C2  HC2  SING N N 6  
AXL C3  S4   SING N N 7  
AXL C3  N7   SING N N 8  
AXL C3  HC3  SING N N 9  
AXL S4  C5   SING N N 10 
AXL C5  C51  SING N N 11 
AXL C5  C52  SING N N 12 
AXL C5  C6   SING N N 13 
AXL C51 H511 SING N N 14 
AXL C51 H512 SING N N 15 
AXL C51 H513 SING N N 16 
AXL C52 H521 SING N N 17 
AXL C52 H522 SING N N 18 
AXL C52 H523 SING N N 19 
AXL C6  C61  SING N N 20 
AXL C6  N7   SING N N 21 
AXL C6  HC6  SING N N 22 
AXL C61 O62  SING N N 23 
AXL C61 O63  DOUB N N 24 
AXL O62 H62O SING N N 25 
AXL N7  HN7  SING N N 26 
AXL N8  C9   SING N N 27 
AXL N8  HN8  SING N N 28 
AXL C9  O91  DOUB N N 29 
AXL C9  C10  SING N N 30 
AXL C10 N11  SING N N 31 
AXL C10 C12  SING N N 32 
AXL C10 H10  SING N N 33 
AXL N11 H111 SING N N 34 
AXL N11 H112 SING N N 35 
AXL C12 C13  DOUB Y N 36 
AXL C12 C17  SING Y N 37 
AXL C13 C14  SING Y N 38 
AXL C13 H13  SING N N 39 
AXL C14 C15  DOUB Y N 40 
AXL C14 H14  SING N N 41 
AXL C15 C16  SING Y N 42 
AXL C15 O18  SING N N 43 
AXL C16 C17  DOUB Y N 44 
AXL C16 H16  SING N N 45 
AXL C17 H17  SING N N 46 
AXL O18 H18O SING N N 47 
# 
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 
AXL SMILES           ACDLabs              12.01 "O=C(NC(C=O)C1SC(C(N1)C(=O)O)(C)C)C(c2ccc(O)cc2)N"                                                                                                                       
AXL InChI            InChI                1.03  "InChI=1S/C16H21N3O5S/c1-16(2)12(15(23)24)19-14(25-16)10(7-20)18-13(22)11(17)8-3-5-9(21)6-4-8/h3-7,10-12,14,19,21H,17H2,1-2H3,(H,18,22)(H,23,24)/t10-,11-,12+,14-/m1/s1" 
AXL InChIKey         InChI                1.03  SMLJDSWXGVMNTH-NRWUCQMLSA-N                                                                                                                                              
AXL SMILES_CANONICAL CACTVS               3.370 "CC1(C)S[C@@H](N[C@H]1C(O)=O)[C@H](NC(=O)[C@H](N)c2ccc(O)cc2)C=O"                                                                                                        
AXL SMILES           CACTVS               3.370 "CC1(C)S[CH](N[CH]1C(O)=O)[CH](NC(=O)[CH](N)c2ccc(O)cc2)C=O"                                                                                                             
AXL SMILES_CANONICAL "OpenEye OEToolkits" 1.7.6 "CC1([C@@H](N[C@H](S1)[C@@H](C=O)NC(=O)[C@@H](c2ccc(cc2)O)N)C(=O)O)C"                                                                                                    
AXL SMILES           "OpenEye OEToolkits" 1.7.6 "CC1(C(NC(S1)C(C=O)NC(=O)C(c2ccc(cc2)O)N)C(=O)O)C"                                                                                                                       
# 
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 
AXL "SYSTEMATIC NAME" ACDLabs              12.01 "(2R,4S)-2-[(1R)-1-{[(2R)-2-amino-2-(4-hydroxyphenyl)acetyl]amino}-2-oxoethyl]-5,5-dimethyl-1,3-thiazolidine-4-carboxylic acid"               
AXL "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.7.6 "(2R,4S)-2-[(1R)-1-[[(2R)-2-azanyl-2-(4-hydroxyphenyl)ethanoyl]amino]-2-oxidanylidene-ethyl]-5,5-dimethyl-1,3-thiazolidine-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 
AXL "Create component"  2002-05-07 RCSB 
AXL "Modify descriptor" 2011-06-04 RCSB 
AXL "Modify synonyms"   2012-03-22 RCSB 
AXL "Modify synonyms"   2020-06-05 PDBE 
AXL "Modify PCM"        2024-09-27 PDBE 
# 
_pdbx_chem_comp_synonyms.ordinal      1 
_pdbx_chem_comp_synonyms.comp_id      AXL 
_pdbx_chem_comp_synonyms.name         "AMOXICILLIN, 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                            AXL 
_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               C1 
_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      ? 
# 
