data_EB4 # _chem_comp.id EB4 _chem_comp.name "N,N',N''-[(3S,7S,11S)-2,6,10-trioxo-1,5,9-trioxacyclododecane-3,7,11-triyl]tris(2,3-dihydroxybenzamide)" _chem_comp.type NON-POLYMER _chem_comp.pdbx_type HETAIN _chem_comp.formula "C30 H27 N3 O15" _chem_comp.mon_nstd_parent_comp_id ? _chem_comp.pdbx_synonyms Enterobactin _chem_comp.pdbx_formal_charge 0 _chem_comp.pdbx_initial_date 2008-04-08 _chem_comp.pdbx_modified_date 2021-03-01 _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 669.546 _chem_comp.one_letter_code ? _chem_comp.three_letter_code EB4 _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 3CMP _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 EB4 O6 O6 O 0 1 N N N 30.100 75.161 64.056 3.664 -4.780 3.535 O6 EB4 1 EB4 O4 O4 O 0 1 N N N 26.728 77.394 62.867 -5.885 -0.658 3.769 O4 EB4 2 EB4 O5 O5 O 0 1 N N N 26.452 75.737 65.629 2.529 5.436 3.577 O5 EB4 3 EB4 N1 N1 N 0 1 N N N 29.185 81.559 64.787 -2.549 1.052 -1.007 N1 EB4 4 EB4 C5 C5 C 0 1 Y N N 25.683 76.442 66.506 2.387 4.234 2.956 C5 EB4 5 EB4 C4 C4 C 0 1 Y N N 26.835 78.712 62.547 -4.794 -0.158 3.129 C4 EB4 6 EB4 C1 C1 C 0 1 Y N N 27.830 79.476 63.131 -4.784 -0.064 1.740 C1 EB4 7 EB4 C2 C2 C 0 1 Y N N 25.885 77.805 66.665 2.407 4.162 1.566 C2 EB4 8 EB4 C6 C6 C 0 1 Y N N 31.022 75.479 65.007 2.659 -4.078 2.945 C6 EB4 9 EB4 C8 C8 C 0 1 Y N N 24.693 75.794 67.240 2.228 3.081 3.707 C8 EB4 10 EB4 N2 N2 N 0 1 N N N 26.488 80.476 68.149 2.140 1.635 -1.142 N2 EB4 11 EB4 C9 C9 C 0 1 Y N N 32.293 74.914 64.964 1.784 -3.337 3.720 C9 EB4 12 EB4 C10 C10 C 0 1 Y N N 26.070 80.636 61.320 -2.580 0.773 3.213 C10 EB4 13 EB4 O3 O3 O 0 1 N N N 29.449 76.918 66.052 3.374 -4.820 0.796 O3 EB4 14 EB4 N3 N3 N 0 1 N N N 31.321 78.969 67.840 0.316 -2.690 -1.079 N3 EB4 15 EB4 C16 C16 C 0 1 Y N N 27.950 80.825 62.822 -3.658 0.451 1.088 C16 EB4 16 EB4 C7 C7 C 0 1 Y N N 25.952 79.287 61.640 -3.695 0.263 3.858 C7 EB4 17 EB4 C3 C3 C 0 1 Y N N 30.697 76.368 66.020 2.515 -4.099 1.561 C3 EB4 18 EB4 C11 C11 C 0 1 Y N N 23.909 76.514 68.134 2.083 1.854 3.082 C11 EB4 19 EB4 O1 O1 O 0 1 N N N 28.680 78.884 64.018 -5.862 -0.471 1.022 O1 EB4 20 EB4 O2 O2 O 0 1 N N N 26.856 78.426 65.940 2.568 5.288 0.827 O2 EB4 21 EB4 C12 C12 C 0 1 Y N N 33.233 75.242 65.938 0.758 -2.620 3.127 C12 EB4 22 EB4 C15 C15 C 0 1 Y N N 32.904 76.135 66.956 0.599 -2.636 1.759 C15 EB4 23 EB4 C14 C14 C 0 1 Y N N 24.112 77.882 68.292 2.096 1.767 1.707 C14 EB4 24 EB4 C13 C13 C 0 1 Y N N 27.071 81.403 61.911 -2.554 0.867 1.839 C13 EB4 25 EB4 O7 O7 O 0 1 N N N 29.732 82.353 62.755 -4.597 0.193 -1.033 O7 EB4 26 EB4 C19 C19 C 0 1 N N N 29.034 81.644 63.462 -3.635 0.555 -0.383 C19 EB4 27 EB4 C22 C22 C 0 1 N N S 30.211 82.269 65.547 -2.527 1.156 -2.469 C22 EB4 28 EB4 C25 C25 C 0 1 N N N 31.293 81.300 65.960 -2.086 -0.159 -3.059 C25 EB4 29 EB4 O10 O10 O 0 1 N N N 31.542 80.337 65.248 -2.070 -0.308 -4.257 O10 EB4 30 EB4 O15 O15 O 0 1 N N N 32.092 81.466 67.178 -1.712 -1.165 -2.252 O15 EB4 31 EB4 C30 C30 C 0 1 N N N 31.683 81.259 68.544 -1.304 -2.404 -2.889 C30 EB4 32 EB4 C24 C24 C 0 1 N N S 30.919 79.960 68.835 0.154 -2.704 -2.535 C24 EB4 33 EB4 C21 C21 C 0 1 N N N 31.243 77.659 68.077 1.315 -3.389 -0.505 C21 EB4 34 EB4 C18 C18 C 0 1 Y N N 31.634 76.699 66.992 1.479 -3.374 0.961 C18 EB4 35 EB4 O9 O9 O 0 1 N N N 30.846 77.208 69.141 2.082 -4.032 -1.196 O9 EB4 36 EB4 C27 C27 C 0 1 N N N 29.415 80.118 68.786 1.046 -1.657 -3.150 C27 EB4 37 EB4 O12 O12 O 0 1 N N N 28.792 79.505 67.935 1.110 -1.548 -4.352 O12 EB4 38 EB4 C28 C28 C 0 1 N N N 29.575 82.856 66.800 -1.550 2.256 -2.887 C28 EB4 39 EB4 O13 O13 O 0 1 N N N 28.248 83.350 66.654 -0.249 1.998 -2.297 O13 EB4 40 EB4 C26 C26 C 0 1 N N N 27.100 82.498 66.940 0.778 1.819 -3.143 C26 EB4 41 EB4 O11 O11 O 0 1 N N N 26.369 82.265 65.991 0.596 1.877 -4.336 O11 EB4 42 EB4 C23 C23 C 0 1 N N S 26.767 81.906 68.302 2.159 1.546 -2.604 C23 EB4 43 EB4 C29 C29 C 0 1 N N N 27.848 82.093 69.394 2.602 0.143 -3.024 C29 EB4 44 EB4 O14 O14 O 0 1 N N N 28.658 80.945 69.728 1.769 -0.845 -2.363 O14 EB4 45 EB4 C20 C20 C 0 1 N N N 25.312 80.005 67.726 2.281 2.831 -0.538 C20 EB4 46 EB4 O8 O8 O 0 1 N N N 24.377 80.738 67.447 2.424 3.837 -1.206 O8 EB4 47 EB4 C17 C17 C 0 1 Y N N 25.106 78.526 67.563 2.261 2.921 0.935 C17 EB4 48 EB4 HO6 HO6 H 0 1 N N N 29.242 75.087 64.458 4.485 -4.280 3.639 HO6 EB4 49 EB4 HO4 HO4 H 0 1 N N N 26.703 76.876 62.071 -5.858 -1.615 3.902 HO4 EB4 50 EB4 HO5 HO5 H 0 1 N N N 25.958 75.573 64.835 1.694 5.896 3.738 HO5 EB4 51 EB4 HN1 HN1 H 0 1 N N N 28.554 80.970 65.292 -1.782 1.341 -0.489 HN1 EB4 52 EB4 H8 H8 H 0 1 N N N 24.534 74.733 67.115 2.217 3.140 4.785 H8 EB4 53 EB4 HN2 HN2 H 0 1 N N N 27.211 79.822 68.372 2.025 0.833 -0.609 HN2 EB4 54 EB4 H9 H9 H 0 1 N N N 32.550 74.222 64.176 1.901 -3.319 4.794 H9 EB4 55 EB4 H10 H10 H 0 1 N N N 25.387 81.087 60.615 -1.728 1.099 3.790 H10 EB4 56 EB4 HO3 HO3 H 0 1 N N N 29.182 77.046 66.955 3.093 -5.732 0.641 HO3 EB4 57 EB4 HN3 HN3 H 0 1 N N N 31.665 79.282 66.955 -0.296 -2.177 -0.528 HN3 EB4 58 EB4 H7 H7 H 0 1 N N N 25.177 78.688 61.185 -3.707 0.193 4.936 H7 EB4 59 EB4 H11 H11 H 0 1 N N N 23.143 76.012 68.706 1.961 0.960 3.675 H11 EB4 60 EB4 HO1 HO1 H 0 1 N N N 29.524 78.746 63.605 -6.516 0.225 0.866 HO1 EB4 61 EB4 HO2 HO2 H 0 1 N N N 26.546 78.571 65.054 3.491 5.502 0.632 HO2 EB4 62 EB4 H12 H12 H 0 1 N N N 34.219 74.803 65.904 0.080 -2.045 3.740 H12 EB4 63 EB4 H15 H15 H 0 1 N N N 33.632 76.388 67.713 -0.203 -2.076 1.302 H15 EB4 64 EB4 H14 H14 H 0 1 N N N 23.498 78.443 68.981 1.983 0.807 1.225 H14 EB4 65 EB4 H13 H13 H 0 1 N N N 27.165 82.450 61.662 -1.682 1.265 1.341 H13 EB4 66 EB4 H22 H22 H 0 1 N N N 30.645 83.067 64.927 -3.526 1.400 -2.831 H22 EB4 67 EB4 H30 H30 H 0 1 N N N 32.595 81.246 69.159 -1.938 -3.218 -2.538 H30 EB4 68 EB4 H30A H30A H 0 0 N N N 30.981 82.075 68.771 -1.403 -2.306 -3.970 H30A EB4 69 EB4 H24 H24 H 0 1 N N N 31.170 79.651 69.860 0.427 -3.687 -2.921 H24 EB4 70 EB4 H28 H28 H 0 1 N N N 29.547 82.059 67.558 -1.461 2.269 -3.973 H28 EB4 71 EB4 H28A H28A H 0 0 N N N 30.191 83.726 67.070 -1.921 3.221 -2.542 H28A EB4 72 EB4 H23 H23 H 0 1 N N N 25.891 82.468 68.656 2.857 2.283 -3.004 H23 EB4 73 EB4 H29 H29 H 0 1 N N N 28.533 82.875 69.036 2.503 0.039 -4.104 H29 EB4 74 EB4 H29A H29A H 0 0 N N N 27.290 82.328 70.313 3.643 -0.009 -2.739 H29A EB4 75 # # 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 EB4 O6 C6 SING N N 1 EB4 O6 HO6 SING N N 2 EB4 O4 HO4 SING N N 3 EB4 O5 C5 SING N N 4 EB4 O5 HO5 SING N N 5 EB4 N1 C22 SING N N 6 EB4 N1 HN1 SING N N 7 EB4 C5 C2 DOUB Y N 8 EB4 C5 C8 SING Y N 9 EB4 C4 O4 SING N N 10 EB4 C4 C1 SING Y N 11 EB4 C1 O1 SING N N 12 EB4 C2 C17 SING Y N 13 EB4 C6 C3 SING Y N 14 EB4 C8 C11 DOUB Y N 15 EB4 C8 H8 SING N N 16 EB4 N2 C23 SING N N 17 EB4 N2 HN2 SING N N 18 EB4 C9 C6 DOUB Y N 19 EB4 C9 C12 SING Y N 20 EB4 C9 H9 SING N N 21 EB4 C10 C7 SING Y N 22 EB4 C10 C13 DOUB Y N 23 EB4 C10 H10 SING N N 24 EB4 O3 HO3 SING N N 25 EB4 N3 C21 SING N N 26 EB4 N3 C24 SING N N 27 EB4 N3 HN3 SING N N 28 EB4 C16 C1 DOUB Y N 29 EB4 C16 C19 SING N N 30 EB4 C7 C4 DOUB Y N 31 EB4 C7 H7 SING N N 32 EB4 C3 O3 SING N N 33 EB4 C3 C18 DOUB Y N 34 EB4 C11 C14 SING Y N 35 EB4 C11 H11 SING N N 36 EB4 O1 HO1 SING N N 37 EB4 O2 C2 SING N N 38 EB4 O2 HO2 SING N N 39 EB4 C12 C15 DOUB Y N 40 EB4 C12 H12 SING N N 41 EB4 C15 C18 SING Y N 42 EB4 C15 H15 SING N N 43 EB4 C14 H14 SING N N 44 EB4 C13 C16 SING Y N 45 EB4 C13 H13 SING N N 46 EB4 O7 C19 DOUB N N 47 EB4 C19 N1 SING N N 48 EB4 C22 C25 SING N N 49 EB4 C22 C28 SING N N 50 EB4 C22 H22 SING N N 51 EB4 C25 O15 SING N N 52 EB4 O10 C25 DOUB N N 53 EB4 O15 C30 SING N N 54 EB4 C30 C24 SING N N 55 EB4 C30 H30 SING N N 56 EB4 C30 H30A SING N N 57 EB4 C24 H24 SING N N 58 EB4 C21 O9 DOUB N N 59 EB4 C18 C21 SING N N 60 EB4 C27 C24 SING N N 61 EB4 C27 O14 SING N N 62 EB4 O12 C27 DOUB N N 63 EB4 C28 H28 SING N N 64 EB4 C28 H28A SING N N 65 EB4 O13 C28 SING N N 66 EB4 O13 C26 SING N N 67 EB4 C26 C23 SING N N 68 EB4 O11 C26 DOUB N N 69 EB4 C23 C29 SING N N 70 EB4 C23 H23 SING N N 71 EB4 C29 O14 SING N N 72 EB4 C29 H29 SING N N 73 EB4 C29 H29A SING N N 74 EB4 C20 N2 SING N N 75 EB4 O8 C20 DOUB N N 76 EB4 C17 C14 DOUB Y N 77 EB4 C17 C20 SING N N 78 # # 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 EB4 SMILES ACDLabs 10.04 "O=C2OCC(C(=O)OCC(C(=O)OCC2NC(=O)c1cccc(O)c1O)NC(=O)c3cccc(O)c3O)NC(=O)c4cccc(O)c4O" EB4 SMILES_CANONICAL CACTVS 3.341 "Oc1cccc(C(=O)N[C@H]2COC(=O)[C@H](COC(=O)[C@H](COC2=O)NC(=O)c3cccc(O)c3O)NC(=O)c4cccc(O)c4O)c1O" EB4 SMILES CACTVS 3.341 "Oc1cccc(C(=O)N[CH]2COC(=O)[CH](COC(=O)[CH](COC2=O)NC(=O)c3cccc(O)c3O)NC(=O)c4cccc(O)c4O)c1O" EB4 SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 "c1cc(c(c(c1)O)O)C(=O)N[C@H]2COC(=O)[C@H](COC(=O)[C@H](COC2=O)NC(=O)c3cccc(c3O)O)NC(=O)c4cccc(c4O)O" EB4 SMILES "OpenEye OEToolkits" 1.5.0 "c1cc(c(c(c1)O)O)C(=O)NC2COC(=O)C(COC(=O)C(COC2=O)NC(=O)c3cccc(c3O)O)NC(=O)c4cccc(c4O)O" EB4 InChI InChI 1.03 "InChI=1S/C30H27N3O15/c34-19-7-1-4-13(22(19)37)25(40)31-16-10-46-29(44)18(33-27(42)15-6-3-9-21(36)24(15)39)12-48-30(45)17(11-47-28(16)43)32-26(41)14-5-2-8-20(35)23(14)38/h1-9,16-18,34-39H,10-12H2,(H,31,40)(H,32,41)(H,33,42)/t16-,17-,18-/m0/s1" EB4 InChIKey InChI 1.03 SERBHKJMVBATSJ-BZSNNMDCSA-N # # 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 EB4 "SYSTEMATIC NAME" ACDLabs 10.04 "N,N',N''-[(3S,7S,11S)-2,6,10-trioxo-1,5,9-trioxacyclododecane-3,7,11-triyl]tris(2,3-dihydroxybenzamide)" EB4 "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "N-[(3S,7S,11S)-7,11-bis[(2,3-dihydroxyphenyl)carbonylamino]-2,6,10-trioxo-1,5,9-trioxacyclododec-3-yl]-2,3-dihydroxy-benzamide" # # loop_ _pdbx_chem_comp_audit.comp_id _pdbx_chem_comp_audit.action_type _pdbx_chem_comp_audit.date _pdbx_chem_comp_audit.processing_site EB4 "Create component" 2008-04-08 RCSB EB4 "Modify descriptor" 2011-06-04 RCSB EB4 "Modify synonyms" 2021-03-01 PDBE # _pdbx_chem_comp_synonyms.ordinal 1 _pdbx_chem_comp_synonyms.comp_id EB4 _pdbx_chem_comp_synonyms.name Enterobactin _pdbx_chem_comp_synonyms.provenance ? _pdbx_chem_comp_synonyms.type ? ##