data_O34 # _chem_comp.id O34 _chem_comp.name yersiniabactin _chem_comp.type NON-POLYMER _chem_comp.pdbx_type HETAIN _chem_comp.formula "C21 H27 N3 O4 S3" _chem_comp.mon_nstd_parent_comp_id ? _chem_comp.pdbx_synonyms ;(4S)-2-[(1S)-1-hydroxy-1-{(2R,4R)-2-[(4R)-2-(2-hydroxyphenyl)-4,5-dihydro-1,3-thiazol-4-yl]-1,3-thiazolidin-4-yl}-2-met hylpropan-2-yl]-4-methyl-4,5-dihydro-1,3-thiazole-4-carboxylic acid ; _chem_comp.pdbx_formal_charge 0 _chem_comp.pdbx_initial_date 2019-06-05 _chem_comp.pdbx_modified_date 2020-06-17 _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 481.652 _chem_comp.one_letter_code ? _chem_comp.three_letter_code O34 _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 6P6J _chem_comp.pdbx_subcomponent_list ? _chem_comp.pdbx_processing_site RCSB # # 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.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 O34 N1 N1 N 0 1 N N N 132.353 147.795 153.027 -2.416 0.350 -0.087 N1A O34 1 O34 N2 N2 N 0 1 N N N 133.581 147.611 150.624 -0.155 -0.912 -1.253 N2A O34 2 O34 N3 N3 N 0 1 N N N 136.326 147.448 151.840 2.601 0.230 0.822 N3A O34 3 O34 O1 O1 O 0 1 N N N 134.595 148.094 154.572 -3.349 -1.751 1.160 O1A O34 4 O34 O2 O2 O 0 1 N N N 134.583 149.608 152.004 3.044 -2.697 -1.803 O2A O34 5 O34 O3 O3 O 0 1 N N N 134.615 145.777 152.812 2.726 1.762 3.132 O3A O34 6 O34 O4 O4 O 0 1 N N N 135.894 143.992 152.524 4.886 1.990 2.727 O4A O34 7 O34 S1 S1 S 0 1 N N N 129.974 147.823 153.999 -3.729 2.327 -0.919 S1A O34 8 O34 S2 S2 S 0 1 N N N 131.506 148.298 149.117 0.796 1.260 -2.391 S2A O34 9 O34 S3 S3 S 0 1 N N N 138.073 147.121 149.979 4.590 -0.970 -0.125 S3A O34 10 O34 C1 C1 C 0 1 Y N N 133.792 147.773 155.557 -4.594 -1.217 1.074 C1A O34 11 O34 C2 C2 C 0 1 Y N N 134.347 147.622 156.857 -5.680 -1.896 1.606 C2A O34 12 O34 C3 C3 C 0 1 Y N N 133.545 147.317 157.934 -6.947 -1.352 1.518 C3A O34 13 O34 C4 C4 C 0 1 Y N N 132.163 147.168 157.788 -7.141 -0.127 0.900 C4A O34 14 O34 C5 C5 C 0 1 Y N N 131.588 147.329 156.544 -6.071 0.560 0.367 C5A O34 15 O34 C6 C6 C 0 1 Y N N 132.396 147.593 155.437 -4.786 0.023 0.454 C6A O34 16 O34 C7 C7 C 0 1 N N N 131.752 147.719 154.135 -3.634 0.758 -0.111 C7A O34 17 O34 C8 C8 C 0 1 N N N 130.102 147.572 152.209 -1.945 2.458 -1.267 C8A O34 18 O34 C9 C9 C 0 1 N N R 131.501 148.087 151.866 -1.373 1.161 -0.675 C9A O34 19 O34 C10 C10 C 0 1 N N R 132.110 147.474 150.609 -0.685 0.364 -1.785 C10A O34 20 O34 C11 C11 C 0 1 N N N 132.800 149.552 149.351 2.004 -0.075 -2.024 C11A O34 21 O34 C12 C12 C 0 1 N N R 134.037 148.777 149.805 1.069 -1.314 -1.972 C12A O34 22 O34 C13 C13 C 0 1 N N S 134.961 149.687 150.667 1.760 -2.457 -1.224 C13A O34 23 O34 C14 C14 C 0 1 N N N 136.481 149.442 150.452 1.927 -2.075 0.248 C14A O34 24 O34 C15 C15 C 0 1 N N N 136.858 149.757 148.999 0.571 -1.664 0.825 C15A O34 25 O34 C16 C16 C 0 1 N N N 137.276 150.366 151.400 2.471 -3.274 1.027 C16A O34 26 O34 C17 C17 C 0 1 N N N 136.855 148.033 150.827 2.891 -0.922 0.361 C17A O34 27 O34 C18 C18 C 0 1 N N N 137.674 145.632 150.948 4.958 0.752 0.342 C18A O34 28 O34 C19 C19 C 0 1 N N S 136.884 146.129 152.154 3.612 1.262 0.883 C19A O34 29 O34 C20 C20 C 0 1 N N N 137.786 146.274 153.391 3.157 2.461 0.048 C20A O34 30 O34 C21 C21 C 0 1 N N N 135.711 145.204 152.505 3.788 1.698 2.315 C21A O34 31 O34 H1 H1 H 0 1 N N N 133.988 146.776 150.254 -0.854 -1.639 -1.294 H1 O34 32 O34 H5 H5 H 0 1 N N N 135.486 148.158 154.897 -3.110 -2.315 0.412 H5 O34 33 O34 H6 H6 H 0 1 N N N 135.149 150.164 152.527 3.638 -1.934 -1.772 H6 O34 34 O34 H7 H7 H 0 1 N N N 133.972 145.122 153.055 2.888 2.047 4.042 H7 O34 35 O34 H8 H8 H 0 1 N N N 135.410 147.748 157.002 -5.536 -2.851 2.089 H8 O34 36 O34 H9 H9 H 0 1 N N N 133.992 147.191 158.909 -7.790 -1.884 1.932 H9 O34 37 O34 H10 H10 H 0 1 N N N 131.549 146.928 158.644 -8.135 0.291 0.836 H10 O34 38 O34 H11 H11 H 0 1 N N N 130.517 147.251 156.427 -6.227 1.514 -0.114 H11 O34 39 O34 H12 H12 H 0 1 N N N 129.331 148.148 151.677 -1.765 2.503 -2.341 H12 O34 40 O34 H13 H13 H 0 1 N N N 130.004 146.506 151.955 -1.520 3.331 -0.770 H13 O34 41 O34 H14 H14 H 0 1 N N N 131.444 149.177 151.727 -0.640 1.410 0.091 H14 O34 42 O34 H15 H15 H 0 1 N N N 131.819 146.416 150.527 -1.377 0.176 -2.606 H15 O34 43 O34 H16 H16 H 0 1 N N N 133.001 150.079 148.407 2.739 -0.170 -2.824 H16 O34 44 O34 H17 H17 H 0 1 N N N 132.497 150.279 150.119 2.492 0.090 -1.063 H17 O34 45 O34 H18 H18 H 0 1 N N N 134.595 148.424 148.925 0.817 -1.631 -2.984 H18 O34 46 O34 H19 H19 H 0 1 N N N 134.772 150.715 150.325 1.153 -3.359 -1.299 H19 O34 47 O34 H20 H20 H 0 1 N N N 137.934 149.582 148.853 -0.203 -2.331 0.445 H20 O34 48 O34 H21 H21 H 0 1 N N N 136.285 149.106 148.322 0.604 -1.729 1.913 H21 O34 49 O34 H22 H22 H 0 1 N N N 136.625 150.809 148.780 0.345 -0.640 0.529 H22 O34 50 O34 H23 H23 H 0 1 N N N 137.007 150.141 152.443 3.437 -3.566 0.615 H23 O34 51 O34 H24 H24 H 0 1 N N N 138.354 150.199 151.256 2.590 -3.002 2.076 H24 O34 52 O34 H25 H25 H 0 1 N N N 137.034 151.416 151.177 1.774 -4.107 0.945 H25 O34 53 O34 H27 H27 H 0 1 N N N 137.066 144.936 150.351 5.722 0.786 1.118 H27 O34 54 O34 H28 H28 H 0 1 N N N 138.595 145.127 151.274 5.266 1.330 -0.529 H28 O34 55 O34 H29 H29 H 0 1 N N N 137.188 146.633 154.241 2.231 2.861 0.461 H29 O34 56 O34 H30 H30 H 0 1 N N N 138.227 145.297 153.640 3.927 3.232 0.070 H30 O34 57 O34 H31 H31 H 0 1 N N N 138.589 146.995 153.177 2.988 2.144 -0.981 H31 O34 58 # # 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 O34 C15 C14 SING N N 1 O34 S2 C11 SING N N 2 O34 S2 C10 SING N N 3 O34 C11 C12 SING N N 4 O34 C12 N2 SING N N 5 O34 C12 C13 SING N N 6 O34 S3 C17 SING N N 7 O34 S3 C18 SING N N 8 O34 C14 C13 SING N N 9 O34 C14 C17 SING N N 10 O34 C14 C16 SING N N 11 O34 C10 N2 SING N N 12 O34 C10 C9 SING N N 13 O34 C13 O2 SING N N 14 O34 C17 N3 DOUB N N 15 O34 C18 C19 SING N N 16 O34 N3 C19 SING N N 17 O34 C9 C8 SING N N 18 O34 C9 N1 SING N N 19 O34 C19 C21 SING N N 20 O34 C19 C20 SING N N 21 O34 C8 S1 SING N N 22 O34 C21 O4 DOUB N N 23 O34 C21 O3 SING N N 24 O34 N1 C7 DOUB N N 25 O34 S1 C7 SING N N 26 O34 C7 C6 SING N N 27 O34 O1 C1 SING N N 28 O34 C6 C1 DOUB Y N 29 O34 C6 C5 SING Y N 30 O34 C1 C2 SING Y N 31 O34 C5 C4 DOUB Y N 32 O34 C2 C3 DOUB Y N 33 O34 C4 C3 SING Y N 34 O34 N2 H1 SING N N 35 O34 O1 H5 SING N N 36 O34 O2 H6 SING N N 37 O34 O3 H7 SING N N 38 O34 C2 H8 SING N N 39 O34 C3 H9 SING N N 40 O34 C4 H10 SING N N 41 O34 C5 H11 SING N N 42 O34 C8 H12 SING N N 43 O34 C8 H13 SING N N 44 O34 C9 H14 SING N N 45 O34 C10 H15 SING N N 46 O34 C11 H16 SING N N 47 O34 C11 H17 SING N N 48 O34 C12 H18 SING N N 49 O34 C13 H19 SING N N 50 O34 C15 H20 SING N N 51 O34 C15 H21 SING N N 52 O34 C15 H22 SING N N 53 O34 C16 H23 SING N N 54 O34 C16 H24 SING N N 55 O34 C16 H25 SING N N 56 O34 C18 H27 SING N N 57 O34 C18 H28 SING N N 58 O34 C20 H29 SING N N 59 O34 C20 H30 SING N N 60 O34 C20 H31 SING N N 61 # # 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 O34 SMILES ACDLabs 12.01 "N1=C(SCC1C2NC(CS2)C(O)C(C3=NC(CS3)(C(O)=O)C)(C)C)c4c(O)cccc4" O34 InChI InChI 1.03 "InChI=1S/C21H27N3O4S3/c1-20(2,18-24-21(3,10-31-18)19(27)28)15(26)12-8-30-17(22-12)13-9-29-16(23-13)11-6-4-5-7-14(11)25/h4-7,12-13,15,17,22,25-26H,8-10H2,1-3H3,(H,27,28)/t12-,13+,15+,17+,21+/m0/s1" O34 InChIKey InChI 1.03 JHYVWAMMAMCUIR-NIJJZIDKSA-N O34 SMILES_CANONICAL CACTVS 3.385 "CC(C)([C@H](O)[C@@H]1CS[C@@H](N1)[C@H]2CSC(=N2)c3ccccc3O)C4=N[C@](C)(CS4)C(O)=O" O34 SMILES CACTVS 3.385 "CC(C)([CH](O)[CH]1CS[CH](N1)[CH]2CSC(=N2)c3ccccc3O)C4=N[C](C)(CS4)C(O)=O" O34 SMILES_CANONICAL "OpenEye OEToolkits" 2.0.7 "C[C@@]1(CSC(=N1)C(C)(C)[C@@H]([C@@H]2CS[C@@H](N2)[C@H]3CSC(=N3)c4ccccc4O)O)C(=O)O" O34 SMILES "OpenEye OEToolkits" 2.0.7 "CC1(CSC(=N1)C(C)(C)C(C2CSC(N2)C3CSC(=N3)c4ccccc4O)O)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 O34 "SYSTEMATIC NAME" ACDLabs 12.01 "(4S)-2-[(1S)-1-hydroxy-1-{(2R,4R)-2-[(4R)-2-(2-hydroxyphenyl)-4,5-dihydro-1,3-thiazol-4-yl]-1,3-thiazolidin-4-yl}-2-methylpropan-2-yl]-4-methyl-4,5-dihydro-1,3-thiazole-4-carboxylic acid" O34 "SYSTEMATIC NAME" "OpenEye OEToolkits" 2.0.7 "(4~{S})-2-[(1~{S})-1-[(2~{R},4~{R})-2-[(4~{R})-2-(2-hydroxyphenyl)-4,5-dihydro-1,3-thiazol-4-yl]-1,3-thiazolidin-4-yl]-2-methyl-1-oxidanyl-propan-2-yl]-4-methyl-5~{H}-1,3-thiazole-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 O34 "Create component" 2019-06-05 RCSB O34 "Initial release" 2020-03-04 RCSB O34 "Modify synonyms" 2020-06-05 PDBE # _pdbx_chem_comp_synonyms.ordinal 1 _pdbx_chem_comp_synonyms.comp_id O34 _pdbx_chem_comp_synonyms.name "(4S)-2-[(1S)-1-hydroxy-1-{(2R,4R)-2-[(4R)-2-(2-hydroxyphenyl)-4,5-dihydro-1,3-thiazol-4-yl]-1,3-thiazolidin-4-yl}-2-methylpropan-2-yl]-4-methyl-4,5-dihydro-1,3-thiazole-4-carboxylic acid" _pdbx_chem_comp_synonyms.provenance ? _pdbx_chem_comp_synonyms.type ? ##