data_59F
# 
_chem_comp.id                                    59F 
_chem_comp.name                                  "(2R,4R,5R)-2-[(1R)-1-{[(2R)-2-{[(4-ethyl-2,3-dioxopiperazin-1-yl)carbonyl]amino}-2-(4-hydroxyphenyl)acetyl]amino}-2-oxoethyl]-5-methyl-1,3-thiazinane-4-carboxylic acid" 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C23 H29 N5 O8 S" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         ? 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2015-08-27 
_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                        535.570 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     59F 
_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        5DF8 
_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 
59F C11 C1  C 0 1 N N N N N N 0.955  8.945  23.010 -3.227 -0.322 -0.572 C11 59F 1  
59F C13 C2  C 0 1 N N N N N N 4.842  9.266  23.489 -5.657 1.638  1.284  C13 59F 2  
59F C14 C3  C 0 1 Y N N N N N -1.907 10.672 24.042 -0.626 -2.229 1.020  C14 59F 3  
59F C15 C4  C 0 1 Y N N N N N -3.704 9.347  23.108 0.276  -2.377 -1.194 C15 59F 4  
59F C17 C5  C 0 1 N N N N N N 3.747  8.331  25.571 -6.871 0.235  -0.296 C17 59F 5  
59F S01 S1  S 0 1 N N N N N N -5.175 6.323  24.780 4.296  0.748  -1.523 S01 59F 6  
59F O01 O1  O 0 1 N N N N N N -2.731 4.400  21.135 1.667  3.069  -1.328 O01 59F 7  
59F O02 O2  O 0 1 N N N N N N -1.731 6.687  24.884 -0.147 1.509  0.979  O02 59F 8  
59F O03 O3  O 0 1 N N N N N N -7.890 3.386  21.369 5.132  -0.417 2.197  O03 59F 9  
59F O04 O4  O 0 1 N N N N N N -7.456 5.212  20.186 6.973  -0.867 1.061  O04 59F 10 
59F O05 O5  O 0 1 N N N N N N 0.753  9.430  21.901 -3.138 -0.893 -1.640 O05 59F 11 
59F O06 O6  O 0 1 N N N N N N 1.478  7.843  25.525 -5.473 -0.833 -1.863 O06 59F 12 
59F O07 O7  O 0 1 N N N N N N 3.857  7.914  26.732 -7.902 -0.141 -0.815 O07 59F 13 
59F O   O8  O 0 1 N N N N N N -5.080 12.607 24.027 0.778  -5.547 0.519  O   59F 14 
59F N01 N1  N 0 1 N N N N N N -5.525 4.527  22.803 4.849  1.921  0.822  N01 59F 15 
59F N02 N2  N 0 1 N N N N N N -2.780 6.187  22.886 1.495  0.681  -0.261 N02 59F 16 
59F N03 N3  N 0 1 N N N N N N -0.123 8.363  23.762 -2.113 0.004  0.114  N03 59F 17 
59F N04 N4  N 0 1 N N N N N N 2.284  8.931  23.643 -4.440 -0.008 -0.075 N04 59F 18 
59F N05 N5  N 0 1 N N N N N N 4.873  8.772  24.865 -6.902 1.088  0.747  N05 59F 19 
59F C01 C6  C 0 1 N N R N N N -4.663 4.859  23.912 3.870  0.999  0.227  C01 59F 20 
59F C02 C7  C 0 1 N N R N N N -3.230 4.926  23.388 2.468  1.601  0.332  C02 59F 21 
59F C03 C8  C 0 1 N N N N N N -3.012 3.959  22.256 2.429  2.916  -0.403 C03 59F 22 
59F C07 C9  C 0 1 N N R N N N -6.788 5.149  22.521 6.195  1.345  0.833  C07 59F 23 
59F C04 C10 C 0 1 N N R N N N -7.554 5.579  23.608 6.786  1.316  -0.574 C04 59F 24 
59F C05 C11 C 0 1 N N N N N N -6.863 5.718  24.948 6.049  0.274  -1.422 C05 59F 25 
59F C06 C12 C 0 1 N N N N N N -1.982 7.012  23.758 0.207  0.716  0.133  C06 59F 26 
59F C08 C13 C 0 1 N N N N N N -9.072 5.557  23.581 8.270  0.951  -0.496 C08 59F 27 
59F CA  C14 C 0 1 N N R N N N -1.460 8.295  23.228 -0.794 -0.231 -0.478 CA  59F 28 
59F C09 C15 C 0 1 N N N N N N -7.418 4.563  21.293 6.129  -0.061 1.372  C09 59F 29 
59F C10 C16 C 0 1 Y N N N N N -2.367 9.478  23.488 -0.370 -1.652 -0.210 C10 59F 30 
59F C12 C17 C 0 1 N N N N N N 3.414  9.569  22.914 -4.551 0.587  1.258  C12 59F 31 
59F C16 C18 C 0 1 N N N N N N 2.439  8.346  24.935 -5.548 -0.243 -0.806 C16 59F 32 
59F C19 C19 C 0 1 N N N N N N 6.216  8.775  25.441 -8.185 1.464  1.345  C19 59F 33 
59F C20 C20 C 0 1 Y N N N N N -2.800 11.730 24.227 -0.239 -3.531 1.269  C20 59F 34 
59F C21 C21 C 0 1 Y N N N N N -4.583 10.386 23.295 0.656  -3.684 -0.955 C21 59F 35 
59F C22 C22 C 0 1 Y N N N N N -4.142 11.575 23.852 0.404  -4.263 0.280  C22 59F 36 
59F C23 C23 C 0 1 N N N N N N 7.220  8.214  24.452 -8.731 2.708  0.641  C23 59F 37 
59F H1  H1  H 0 1 N N N N N N 5.313  8.508  22.846 -5.353 2.495  0.682  H1  59F 38 
59F H2  H2  H 0 1 N N N N N N 5.428  10.196 23.449 -5.820 1.962  2.312  H2  59F 39 
59F H3  H3  H 0 1 N N N N N N -0.870 10.778 24.325 -1.127 -1.659 1.789  H3  59F 40 
59F H4  H4  H 0 1 N N N N N N -4.049 8.424  22.665 0.472  -1.926 -2.156 H4  59F 41 
59F H5  H5  H 0 1 N N N N N N -8.235 3.128  20.523 5.131  -1.329 2.517  H5  59F 42 
59F H6  H6  H 0 1 N N N N N N -4.653 13.362 24.415 1.670  -5.637 0.880  H6  59F 43 
59F H7  H7  H 0 1 N N N N N N -5.726 3.553  22.905 4.567  2.199  1.750  H7  59F 44 
59F H9  H9  H 0 1 N N N N N N -3.011 6.487  21.960 1.778  0.046  -0.938 H9  59F 45 
59F H10 H10 H 0 1 N N N N N N 0.059  7.998  24.675 -2.185 0.394  0.999  H10 59F 46 
59F H11 H11 H 0 1 N N N N N N -4.712 4.050  24.656 3.901  0.044  0.751  H11 59F 47 
59F H12 H12 H 0 1 N N N N N N -2.568 4.624  24.213 2.221  1.764  1.381  H12 59F 48 
59F H13 H13 H 0 1 N N N N N N -3.100 2.895  22.420 3.082  3.722  -0.103 H13 59F 49 
59F H14 H14 H 0 1 N N N N N N -6.448 6.114  22.117 6.836  1.946  1.479  H14 59F 50 
59F H15 H15 H 0 1 N N N N N N -7.478 6.648  23.360 6.679  2.299  -1.033 H15 59F 51 
59F H16 H16 H 0 1 N N N N N N -7.433 6.425  25.569 6.137  -0.707 -0.956 H16 59F 52 
59F H17 H17 H 0 1 N N N N N N -6.840 4.734  25.439 6.479  0.246  -2.424 H17 59F 53 
59F H18 H18 H 0 1 N N N N N N -9.462 5.937  24.537 8.379  -0.031 -0.035 H18 59F 54 
59F H19 H19 H 0 1 N N N N N N -9.433 6.193  22.759 8.693  0.930  -1.500 H19 59F 55 
59F H20 H20 H 0 1 N N N N N N -9.421 4.525  23.427 8.796  1.694  0.104  H20 59F 56 
59F H21 H21 H 0 1 N N N N N N -1.380 8.188  22.136 -0.843 -0.064 -1.554 H21 59F 57 
59F H22 H22 H 0 1 N N N N N N 3.262  10.658 22.939 -3.603 1.055  1.523  H22 59F 58 
59F H23 H23 H 0 1 N N N N N N 3.386  9.219  21.872 -4.781 -0.194 1.982  H23 59F 59 
59F H24 H24 H 0 1 N N N N N N 6.221  8.157  26.351 -8.893 0.643  1.233  H24 59F 60 
59F H25 H25 H 0 1 N N N N N N 6.498  9.807  25.697 -8.043 1.679  2.405  H25 59F 61 
59F H26 H26 H 0 1 N N N N N N -2.459 12.661 24.656 -0.436 -3.980 2.231  H26 59F 62 
59F H27 H27 H 0 1 N N N N N N -5.618 10.276 23.008 1.160  -4.250 -1.724 H27 59F 63 
59F H28 H28 H 0 1 N N N N N N 8.224  8.224  24.902 -8.023 3.529  0.754  H28 59F 64 
59F H29 H29 H 0 1 N N N N N N 6.944  7.181  24.195 -8.873 2.493  -0.418 H29 59F 65 
59F H30 H30 H 0 1 N N N N N N 7.221  8.830  23.541 -9.686 2.988  1.087  H30 59F 66 
# 
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 
59F O04 C09 DOUB N N 1  
59F O01 C03 DOUB N N 2  
59F C09 O03 SING N N 3  
59F C09 C07 SING N N 4  
59F O05 C11 DOUB N N 5  
59F C03 C02 SING N N 6  
59F C07 N01 SING N N 7  
59F C07 C04 SING N N 8  
59F N01 C01 SING N N 9  
59F N02 C02 SING N N 10 
59F N02 C06 SING N N 11 
59F C12 C13 SING N N 12 
59F C12 N04 SING N N 13 
59F C11 N04 SING N N 14 
59F C11 N03 SING N N 15 
59F C15 C21 DOUB Y N 16 
59F C15 C10 SING Y N 17 
59F CA  C10 SING N N 18 
59F CA  C06 SING N N 19 
59F CA  N03 SING N N 20 
59F C21 C22 SING Y N 21 
59F C02 C01 SING N N 22 
59F C10 C14 DOUB Y N 23 
59F C13 N05 SING N N 24 
59F C08 C04 SING N N 25 
59F C04 C05 SING N N 26 
59F N04 C16 SING N N 27 
59F C06 O02 DOUB N N 28 
59F C22 O   SING N N 29 
59F C22 C20 DOUB Y N 30 
59F C01 S01 SING N N 31 
59F C14 C20 SING Y N 32 
59F C23 C19 SING N N 33 
59F S01 C05 SING N N 34 
59F N05 C19 SING N N 35 
59F N05 C17 SING N N 36 
59F C16 O06 DOUB N N 37 
59F C16 C17 SING N N 38 
59F C17 O07 DOUB N N 39 
59F C13 H1  SING N N 40 
59F C13 H2  SING N N 41 
59F C14 H3  SING N N 42 
59F C15 H4  SING N N 43 
59F O03 H5  SING N N 44 
59F O   H6  SING N N 45 
59F N01 H7  SING N N 46 
59F N02 H9  SING N N 47 
59F N03 H10 SING N N 48 
59F C01 H11 SING N N 49 
59F C02 H12 SING N N 50 
59F C03 H13 SING N N 51 
59F C07 H14 SING N N 52 
59F C04 H15 SING N N 53 
59F C05 H16 SING N N 54 
59F C05 H17 SING N N 55 
59F C08 H18 SING N N 56 
59F C08 H19 SING N N 57 
59F C08 H20 SING N N 58 
59F CA  H21 SING N N 59 
59F C12 H22 SING N N 60 
59F C12 H23 SING N N 61 
59F C19 H24 SING N N 62 
59F C19 H25 SING N N 63 
59F C20 H26 SING N N 64 
59F C21 H27 SING N N 65 
59F C23 H28 SING N N 66 
59F C23 H29 SING N N 67 
59F C23 H30 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 
59F SMILES           ACDLabs              12.01 "C(N1C(C(=O)N(CC1)CC)=O)(NC(C(=O)NC(C2SCC(C(N2)C(O)=O)C)C=O)c3ccc(O)cc3)=O"                                                                                                                                                               
59F InChI            InChI                1.03  "InChI=1S/C23H29N5O8S/c1-3-27-8-9-28(21(33)20(27)32)23(36)26-17(13-4-6-14(30)7-5-13)18(31)24-15(10-29)19-25-16(22(34)35)12(2)11-37-19/h4-7,10,12,15-17,19,25,30H,3,8-9,11H2,1-2H3,(H,24,31)(H,26,36)(H,34,35)/t12-,15+,16+,17+,19+/m0/s1" 
59F InChIKey         InChI                1.03  XXVXTCZUKVAJAU-BMBOTXNISA-N                                                                                                                                                                                                               
59F SMILES_CANONICAL CACTVS               3.385 "CCN1CCN(C(=O)N[C@@H](C(=O)N[C@H](C=O)[C@@H]2N[C@H]([C@@H](C)CS2)C(O)=O)c3ccc(O)cc3)C(=O)C1=O"                                                                                                                                            
59F SMILES           CACTVS               3.385 "CCN1CCN(C(=O)N[CH](C(=O)N[CH](C=O)[CH]2N[CH]([CH](C)CS2)C(O)=O)c3ccc(O)cc3)C(=O)C1=O"                                                                                                                                                    
59F SMILES_CANONICAL "OpenEye OEToolkits" 1.9.2 "CCN1CCN(C(=O)C1=O)C(=O)N[C@H](c2ccc(cc2)O)C(=O)N[C@H](C=O)[C@@H]3N[C@H]([C@H](CS3)C)C(=O)O"                                                                                                                                              
59F SMILES           "OpenEye OEToolkits" 1.9.2 "CCN1CCN(C(=O)C1=O)C(=O)NC(c2ccc(cc2)O)C(=O)NC(C=O)C3NC(C(CS3)C)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 
59F "SYSTEMATIC NAME" ACDLabs              12.01 "(2R,4R,5R)-2-[(1R)-1-{[(2R)-2-{[(4-ethyl-2,3-dioxopiperazin-1-yl)carbonyl]amino}-2-(4-hydroxyphenyl)acetyl]amino}-2-oxoethyl]-5-methyl-1,3-thiazinane-4-carboxylic acid"                         
59F "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.9.2 "(2R,4R,5R)-2-[(1R)-1-[[(2R)-2-[[4-ethyl-2,3-bis(oxidanylidene)piperazin-1-yl]carbonylamino]-2-(4-hydroxyphenyl)ethanoyl]amino]-2-oxidanylidene-ethyl]-5-methyl-1,3-thiazinane-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 
59F "Create component" 2015-08-27 RCSB 
59F "Initial release"  2016-01-13 RCSB 
59F "Modify PCM"       2024-09-27 PDBE 
# 
_pdbx_chem_comp_pcm.pcm_id                             1 
_pdbx_chem_comp_pcm.comp_id                            59F 
_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               C03 
_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      ? 
# 
