data_AW4
# 
_chem_comp.id                                    AW4 
_chem_comp.name                                  "(1S,2S)-2-[(N-{[2-(3-chlorophenyl)ethoxy]carbonyl}-L-leucyl)amino]-1-hydroxy-3-[(3S)-2-oxopyrrolidin-3-yl]propane-1-sulfonic acid" 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C22 H32 Cl N3 O8 S" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         "bound form" 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2017-07-28 
_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                        534.023 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     AW4 
_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        5WKK 
_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 
AW4 C12 C1  C  0 1 N N N N N N -20.359 24.168 7.802  3.135   2.591  0.690  C12 AW4 1  
AW4 C14 C2  C  0 1 N N N N N N -22.667 23.612 7.760  4.924   3.585  1.790  C14 AW4 2  
AW4 C15 C3  C  0 1 N N N N N N -22.454 24.929 6.894  5.219   3.739  0.282  C15 AW4 3  
AW4 C19 C4  C  0 1 N N N N N N -20.667 26.050 -0.480 1.674   -1.468 1.779  C19 AW4 4  
AW4 O01 O1  O  0 1 N N N N N N -20.848 23.217 3.587  -2.041  0.418  0.608  O01 AW4 5  
AW4 C02 C5  C  0 1 N N N N N N -21.672 23.148 2.704  -1.961  -0.114 -0.482 C02 AW4 6  
AW4 N03 N1  N  0 1 N N N N N N -21.798 24.187 1.698  -0.761  -0.507 -0.953 N03 AW4 7  
AW4 C04 C6  C  0 1 N N S N N N -21.151 25.472 1.948  0.430   -0.400 -0.106 C04 AW4 8  
AW4 C05 C7  C  0 1 N N N N N N -21.708 26.034 3.248  1.651   -0.239 -0.974 C05 AW4 9  
AW4 N06 N2  N  0 1 N N N N N N -20.744 26.673 4.117  2.825   0.132  -0.424 N06 AW4 10 
AW4 C07 C8  C  0 1 N N S N N N -21.193 27.242 5.380  3.977   0.421  -1.282 C07 AW4 11 
AW4 C08 C9  C  0 1 N N S N N N -20.777 28.682 5.400  4.709   -0.883 -1.608 C08 AW4 12 
AW4 O09 O2  O  0 1 N N N N N N -21.209 29.293 6.581  5.897   -0.590 -2.347 O09 AW4 13 
AW4 C10 C10 C  0 1 N N N N N N -20.547 26.427 6.541  4.928   1.372  -0.554 C10 AW4 14 
AW4 C11 C11 C  0 1 N N S N N N -21.123 24.959 6.619  4.236   2.720  -0.339 C11 AW4 15 
AW4 N13 N3  N  0 1 N N N N N N -21.281 23.386 8.455  3.544   3.090  1.869  N13 AW4 16 
AW4 O16 O3  O  0 1 N N N N N N -19.213 24.234 8.054  2.041   2.111  0.481  O16 AW4 17 
AW4 O17 O4  O  0 1 N N N N N N -22.866 25.954 3.565  1.578   -0.443 -2.168 O17 AW4 18 
AW4 C18 C12 C  0 1 N N N N N N -21.409 26.425 0.834  0.569   -1.667 0.740  C18 AW4 19 
AW4 C20 C13 C  0 1 N N N N N N -21.188 26.951 -1.593 1.252   -0.382 2.770  C20 AW4 20 
AW4 C21 C14 C  0 1 N N N N N N -19.143 26.138 -0.318 1.911   -2.780 2.530  C21 AW4 21 
AW4 O22 O5  O  0 1 N N N N N N -22.562 22.068 2.620  -3.070  -0.310 -1.218 O22 AW4 22 
AW4 C23 C15 C  0 1 N N N N N N -22.425 21.133 3.685  -4.328  0.138  -0.648 C23 AW4 23 
AW4 C24 C16 C  0 1 N N N N N N -23.425 19.947 3.371  -5.468  -0.168 -1.622 C24 AW4 24 
AW4 C25 C17 C  0 1 Y N N N N N -22.962 19.132 2.138  -6.773  0.298  -1.030 C25 AW4 25 
AW4 C26 C18 C  0 1 Y N N N N N -23.666 19.272 0.935  -7.518  -0.559 -0.242 C26 AW4 26 
AW4 C27 C19 C  0 1 Y N N N N N -23.258 18.536 -0.186 -8.714  -0.130 0.307  C27 AW4 27 
AW4 CL1 CL1 CL 0 0 N N N N N N -24.185 18.733 -1.706 -9.651  -1.205 1.297  CL1 AW4 28 
AW4 C29 C20 C  0 1 Y N N N N N -22.163 17.671 -0.119 -9.163  1.157  0.066  C29 AW4 29 
AW4 C30 C21 C  0 1 Y N N N N N -21.459 17.531 1.095  -8.416  2.013  -0.722 C30 AW4 30 
AW4 C31 C22 C  0 1 Y N N N N N -21.861 18.269 2.228  -7.222  1.583  -1.270 C31 AW4 31 
AW4 H1  H1  H  0 1 N N N N N N -23.460 23.760 8.508  5.609   2.865  2.239  H1  AW4 32 
AW4 H2  H2  H  0 1 N N N N N N -22.925 22.758 7.116  5.008   4.549  2.291  H2  AW4 33 
AW4 H3  H3  H  0 1 N N N N N N -22.750 25.820 7.467  4.996   4.751  -0.057 H3  AW4 34 
AW4 H4  H4  H  0 1 N N N N N N -23.040 24.879 5.964  6.252   3.473  0.058  H4  AW4 35 
AW4 H5  H5  H  0 1 N N N N N N -20.925 25.010 -0.729 2.593   -1.165 1.278  H5  AW4 36 
AW4 H6  H6  H  0 1 N N N N N N -22.314 24.027 0.856  -0.685  -0.860 -1.854 H6  AW4 37 
AW4 H7  H7  H  0 1 N N N N N N -20.066 25.326 2.059  0.333   0.465  0.549  H7  AW4 38 
AW4 H8  H8  H  0 1 N N N N N N -19.781 26.723 3.853  2.906   0.207  0.539  H8  AW4 39 
AW4 H9  H9  H  0 1 N N N N N N -22.288 27.172 5.462  3.634   0.886  -2.206 H9  AW4 40 
AW4 H10 H10 H  0 1 N N N N N N -20.339 29.194 4.531  4.060   -1.525 -2.204 H10 AW4 41 
AW4 H12 H12 H  0 1 N N N N N N -20.940 30.204 6.583  6.522   -0.021 -1.877 H12 AW4 42 
AW4 H13 H13 H  0 1 N N N N N N -19.460 26.375 6.378  5.201   0.945  0.411  H13 AW4 43 
AW4 H14 H14 H  0 1 N N N N N N -20.751 26.940 7.492  5.827   1.517  -1.155 H14 AW4 44 
AW4 H15 H15 H  0 1 N N N N N N -20.898 24.449 5.671  3.836   3.097  -1.280 H15 AW4 45 
AW4 H16 H16 H  0 1 N N N N N N -21.100 22.783 9.232  2.997   3.120  2.670  H16 AW4 46 
AW4 H17 H17 H  0 1 N N N N N N -21.079 27.426 1.148  0.824   -2.508 0.095  H17 AW4 47 
AW4 H18 H18 H  0 1 N N N N N N -22.490 26.442 0.632  -0.374  -1.871 1.247  H18 AW4 48 
AW4 H19 H19 H  0 1 N N N N N N -22.281 26.850 -1.666 2.038   -0.241 3.512  H19 AW4 49 
AW4 H20 H20 H  0 1 N N N N N N -20.931 27.997 -1.369 1.085   0.553  2.236  H20 AW4 50 
AW4 H21 H21 H  0 1 N N N N N N -20.728 26.657 -2.548 0.331   -0.684 3.270  H21 AW4 51 
AW4 H22 H22 H  0 1 N N N N N N -18.821 25.471 0.495  2.211   -3.554 1.823  H22 AW4 52 
AW4 H23 H23 H  0 1 N N N N N N -18.656 25.833 -1.256 2.698   -2.638 3.270  H23 AW4 53 
AW4 H24 H24 H  0 1 N N N N N N -18.859 27.173 -0.077 0.991   -3.083 3.031  H24 AW4 54 
AW4 H25 H25 H  0 1 N N N N N N -21.392 20.757 3.731  -4.506  -0.382 0.294  H25 AW4 55 
AW4 H26 H26 H  0 1 N N N N N N -22.686 21.607 4.643  -4.283  1.212  -0.467 H26 AW4 56 
AW4 H27 H27 H  0 1 N N N N N N -24.423 20.363 3.171  -5.290  0.352  -2.563 H27 AW4 57 
AW4 H28 H28 H  0 1 N N N N N N -23.474 19.279 4.244  -5.513  -1.242 -1.803 H28 AW4 58 
AW4 H29 H29 H  0 1 N N N N N N -24.513 19.939 0.872  -7.168  -1.563 -0.055 H29 AW4 59 
AW4 H30 H30 H  0 1 N N N N N N -21.857 17.113 -0.992 -10.096 1.492  0.493  H30 AW4 60 
AW4 H31 H31 H  0 1 N N N N N N -20.614 16.861 1.157  -8.766  3.017  -0.910 H31 AW4 61 
AW4 H32 H32 H  0 1 N N N N N N -21.324 18.170 3.160  -6.637  2.254  -1.882 H32 AW4 62 
AW4 S1  S1  S  0 1 N N N N N N ?       ?      ?      5.150   -1.731 -0.067 S1  AW4 63 
AW4 O1  O6  O  0 1 N N N N N N ?       ?      ?      5.974   -2.930 -0.515 O1  AW4 64 
AW4 O2  O7  O  0 1 N N N N N N ?       ?      ?      6.058   -0.945 0.693  O2  AW4 65 
AW4 O3  O8  O  0 1 N N N N N N ?       ?      ?      3.997   -2.303 0.535  O3  AW4 66 
AW4 H11 H11 H  0 1 N Y N N N N ?       ?      ?      6.285   -3.487 0.212  H11 AW4 67 
# 
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 
AW4 CL1 C27 SING N N 1  
AW4 C20 C19 SING N N 2  
AW4 C19 C21 SING N N 3  
AW4 C19 C18 SING N N 4  
AW4 C27 C29 DOUB Y N 5  
AW4 C27 C26 SING Y N 6  
AW4 C29 C30 SING Y N 7  
AW4 C18 C04 SING N N 8  
AW4 C26 C25 DOUB Y N 9  
AW4 C30 C31 DOUB Y N 10 
AW4 N03 C04 SING N N 11 
AW4 N03 C02 SING N N 12 
AW4 C04 C05 SING N N 13 
AW4 C25 C31 SING Y N 14 
AW4 C25 C24 SING N N 15 
AW4 O22 C02 SING N N 16 
AW4 O22 C23 SING N N 17 
AW4 C02 O01 DOUB N N 18 
AW4 C05 O17 DOUB N N 19 
AW4 C05 N06 SING N N 20 
AW4 C24 C23 SING N N 21 
AW4 N06 C07 SING N N 22 
AW4 C07 C08 SING N N 23 
AW4 C07 C10 SING N N 24 
AW4 C08 O09 SING N N 25 
AW4 C10 C11 SING N N 26 
AW4 C11 C15 SING N N 27 
AW4 C11 C12 SING N N 28 
AW4 C15 C14 SING N N 29 
AW4 C14 N13 SING N N 30 
AW4 C12 O16 DOUB N N 31 
AW4 C12 N13 SING N N 32 
AW4 C14 H1  SING N N 33 
AW4 C14 H2  SING N N 34 
AW4 C15 H3  SING N N 35 
AW4 C15 H4  SING N N 36 
AW4 C19 H5  SING N N 37 
AW4 N03 H6  SING N N 38 
AW4 C04 H7  SING N N 39 
AW4 N06 H8  SING N N 40 
AW4 C07 H9  SING N N 41 
AW4 C08 H10 SING N N 42 
AW4 O09 H12 SING N N 43 
AW4 C10 H13 SING N N 44 
AW4 C10 H14 SING N N 45 
AW4 C11 H15 SING N N 46 
AW4 N13 H16 SING N N 47 
AW4 C18 H17 SING N N 48 
AW4 C18 H18 SING N N 49 
AW4 C20 H19 SING N N 50 
AW4 C20 H20 SING N N 51 
AW4 C20 H21 SING N N 52 
AW4 C21 H22 SING N N 53 
AW4 C21 H23 SING N N 54 
AW4 C21 H24 SING N N 55 
AW4 C23 H25 SING N N 56 
AW4 C23 H26 SING N N 57 
AW4 C24 H27 SING N N 58 
AW4 C24 H28 SING N N 59 
AW4 C26 H29 SING N N 60 
AW4 C29 H30 SING N N 61 
AW4 C30 H31 SING N N 62 
AW4 C31 H32 SING N N 63 
AW4 C08 S1  SING N N 64 
AW4 S1  O1  SING N N 65 
AW4 S1  O2  DOUB N N 66 
AW4 S1  O3  DOUB N N 67 
AW4 O1  H11 SING N N 68 
# 
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 
AW4 SMILES           ACDLabs              12.01 "C1(=O)NCCC1CC(NC(C(NC(=O)OCCc2cccc(c2)Cl)CC(C)C)=O)C(O)S(O)(=O)=O"                                                                                                                                                                       
AW4 InChI            InChI                1.03  "InChI=1S/C22H32ClN3O8S/c1-13(2)10-17(26-22(30)34-9-7-14-4-3-5-16(23)11-14)20(28)25-18(21(29)35(31,32)33)12-15-6-8-24-19(15)27/h3-5,11,13,15,17-18,21,29H,6-10,12H2,1-2H3,(H,24,27)(H,25,28)(H,26,30)(H,31,32,33)/t15-,17-,18-,21-/m0/s1" 
AW4 InChIKey         InChI                1.03  OKWOXOSOFIECOU-DBSRCYSRSA-N                                                                                                                                                                                                               
AW4 SMILES_CANONICAL CACTVS               3.385 "CC(C)C[C@H](NC(=O)OCCc1cccc(Cl)c1)C(=O)N[C@@H](C[C@@H]2CCNC2=O)[C@@H](O)[S](O)(=O)=O"                                                                                                                                                    
AW4 SMILES           CACTVS               3.385 "CC(C)C[CH](NC(=O)OCCc1cccc(Cl)c1)C(=O)N[CH](C[CH]2CCNC2=O)[CH](O)[S](O)(=O)=O"                                                                                                                                                           
AW4 SMILES_CANONICAL "OpenEye OEToolkits" 2.0.6 "CC(C)C[C@@H](C(=O)N[C@@H](C[C@@H]1CCNC1=O)C(O)S(=O)(=O)O)NC(=O)OCCc2cccc(c2)Cl"                                                                                                                                                          
AW4 SMILES           "OpenEye OEToolkits" 2.0.6 "CC(C)CC(C(=O)NC(CC1CCNC1=O)C(O)S(=O)(=O)O)NC(=O)OCCc2cccc(c2)Cl"                                                                                                                                                                         
# 
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 
AW4 "SYSTEMATIC NAME" ACDLabs              12.01 "(1S,2S)-2-[(N-{[2-(3-chlorophenyl)ethoxy]carbonyl}-L-leucyl)amino]-1-hydroxy-3-[(3S)-2-oxopyrrolidin-3-yl]propane-1-sulfonic acid"                                    
AW4 "SYSTEMATIC NAME" "OpenEye OEToolkits" 2.0.6 "(2~{S})-2-[[(2~{S})-2-[2-(3-chlorophenyl)ethoxycarbonylamino]-4-methyl-pentanoyl]amino]-1-oxidanyl-3-[(3~{S})-2-oxidanylidenepyrrolidin-3-yl]propane-1-sulfonic 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 
AW4 "Create component" 2017-07-28 RCSB 
AW4 "Initial release"  2018-04-04 RCSB 
AW4 "Modify synonyms"  2021-03-01 PDBE 
AW4 "Modify PCM"       2024-09-27 PDBE 
# 
_pdbx_chem_comp_synonyms.ordinal      1 
_pdbx_chem_comp_synonyms.comp_id      AW4 
_pdbx_chem_comp_synonyms.name         "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                            AW4 
_pdbx_chem_comp_pcm.modified_residue_id                CYS 
_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               C08 
_pdbx_chem_comp_pcm.modified_residue_id_linking_atom   SG 
_pdbx_chem_comp_pcm.uniprot_specific_ptm_accession     ? 
_pdbx_chem_comp_pcm.uniprot_generic_ptm_accession      ? 
# 
