data_3XO # _chem_comp.id 3XO _chem_comp.name "2-chloro-4-{[2-(4-methylpiperazin-1-yl)-3,4-dioxocyclobut-1-en-1-yl]amino}phenyl alpha-D-mannopyranoside" _chem_comp.type NON-POLYMER _chem_comp.pdbx_type HETAIN _chem_comp.formula "C21 H26 Cl N3 O8" _chem_comp.mon_nstd_parent_comp_id ? _chem_comp.pdbx_synonyms ? _chem_comp.pdbx_formal_charge 0 _chem_comp.pdbx_initial_date 2014-12-06 _chem_comp.pdbx_modified_date 2015-05-15 _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 483.899 _chem_comp.one_letter_code ? _chem_comp.three_letter_code 3XO _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 4X5R _chem_comp.pdbx_subcomponent_list ? _chem_comp.pdbx_processing_site EBI # 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 3XO O3 O1 O 0 1 N N N 11.708 14.057 -14.979 3.694 0.249 1.394 O3 3XO 1 3XO C4 C1 C 0 1 Y N N 9.717 18.414 -16.147 -0.160 -0.481 -1.929 C4 3XO 2 3XO C5 C2 C 0 1 Y N N 9.398 17.192 -15.573 1.214 -0.342 -1.936 C5 3XO 3 3XO O4 O2 O 0 1 N N N 11.163 13.926 -11.350 6.441 -2.103 0.801 O4 3XO 4 3XO C6 C3 C 0 1 N N N 10.453 20.856 -17.739 -3.078 0.845 -0.294 C6 3XO 5 3XO N1 N1 N 0 1 N N N 11.714 22.545 -19.251 -5.535 0.174 -0.228 N1 3XO 6 3XO C7 C4 C 0 1 N N N 10.790 22.087 -18.377 -4.447 0.984 -0.024 C7 3XO 7 3XO C8 C5 C 0 1 N N N 9.695 22.807 -17.673 -4.280 2.324 0.558 C8 3XO 8 3XO N2 N2 N 0 1 N N N 14.155 23.807 -19.997 -7.466 -1.770 0.280 N2 3XO 9 3XO C9 C6 C 0 1 N N N 9.322 21.482 -16.994 -2.832 2.179 0.274 C9 3XO 10 3XO O5 O3 O 0 1 N N N 9.267 12.052 -12.264 7.403 0.281 -0.453 O5 3XO 11 3XO C10 C7 C 0 1 N N N 12.840 21.749 -19.808 -6.884 0.606 0.171 C10 3XO 12 3XO O6 O4 O 0 1 N N N 10.530 11.420 -14.746 5.854 2.071 1.041 O6 3XO 13 3XO C11 C8 C 0 1 N N N 14.156 22.432 -19.513 -7.518 -0.502 1.019 C11 3XO 14 3XO C12 C9 C 0 1 N N N 13.043 24.541 -19.393 -6.076 -2.189 0.029 C12 3XO 15 3XO C13 C10 C 0 1 N N N 11.718 23.914 -19.768 -5.386 -1.147 -0.857 C13 3XO 16 3XO O7 O5 O 0 1 N N N 14.033 13.638 -13.471 2.733 -2.119 2.709 O7 3XO 17 3XO C14 C11 C 0 1 N N N 15.469 24.487 -19.675 -8.215 -2.820 0.983 C14 3XO 18 3XO C15 C12 C 0 1 N N R 10.413 13.730 -15.439 3.799 1.082 0.238 C15 3XO 19 3XO O2 O6 O 0 1 N N N 8.491 21.183 -16.218 -1.848 2.875 0.441 O2 3XO 20 3XO O1 O7 O 0 1 N N N 9.321 23.924 -17.650 -5.003 3.169 1.050 O1 3XO 21 3XO N N3 N 0 1 N N N 11.035 19.607 -17.825 -2.293 -0.133 -0.852 N 3XO 22 3XO C3 C13 C 0 1 Y N N 10.668 18.441 -17.161 -0.901 0.008 -0.860 C3 3XO 23 3XO C2 C14 C 0 1 Y N N 11.282 17.249 -17.596 -0.260 0.637 0.199 C2 3XO 24 3XO C1 C15 C 0 1 Y N N 10.920 16.029 -16.991 1.114 0.776 0.190 C1 3XO 25 3XO CL CL1 CL 0 0 N N N 8.225 17.158 -14.329 2.141 -0.948 -3.273 CL 3XO 26 3XO C C16 C 0 1 Y N N 9.971 16.019 -15.971 1.855 0.283 -0.874 C 3XO 27 3XO O O8 O 0 1 N N N 9.564 14.851 -15.361 3.207 0.419 -0.882 O 3XO 28 3XO C19 C17 C 0 1 N N S 9.790 12.638 -14.578 5.275 1.362 -0.056 C19 3XO 29 3XO C18 C18 C 0 1 N N S 9.776 13.075 -13.115 6.010 0.032 -0.250 C18 3XO 30 3XO C17 C19 C 0 1 N N S 11.184 13.436 -12.684 5.820 -0.832 1.000 C17 3XO 31 3XO C16 C20 C 0 1 N N R 11.766 14.499 -13.608 4.323 -1.027 1.253 C16 3XO 32 3XO C20 C21 C 0 1 N N N 13.216 14.791 -13.291 4.124 -1.839 2.535 C20 3XO 33 3XO H6 H1 H 0 1 N N N 9.238 19.323 -15.814 -0.659 -0.967 -2.755 H6 3XO 34 3XO H20 H2 H 0 1 N N N 10.800 13.263 -10.774 7.391 -2.055 0.630 H20 3XO 35 3XO H21 H4 H 0 1 N N N 9.272 12.356 -11.364 7.596 0.829 -1.225 H21 3XO 36 3XO H8 H5 H 0 1 N N N 12.715 21.655 -20.897 -6.816 1.522 0.758 H8 3XO 37 3XO H9 H6 H 0 1 N N N 12.839 20.748 -19.351 -7.490 0.780 -0.717 H9 3XO 38 3XO H22 H7 H 0 1 N N N 10.143 10.738 -14.210 5.434 2.922 1.225 H22 3XO 39 3XO H11 H8 H 0 1 N N N 14.967 21.878 -20.008 -8.556 -0.248 1.232 H11 3XO 40 3XO H10 H9 H 0 1 N N N 14.324 22.434 -18.426 -6.969 -0.603 1.955 H10 3XO 41 3XO H12 H10 H 0 1 N N N 13.153 24.525 -18.299 -5.544 -2.270 0.977 H12 3XO 42 3XO H13 H11 H 0 1 N N N 13.063 25.582 -19.748 -6.073 -3.157 -0.473 H13 3XO 43 3XO H15 H12 H 0 1 N N N 10.892 24.486 -19.320 -5.852 -1.137 -1.842 H15 3XO 44 3XO H14 H13 H 0 1 N N N 11.605 23.902 -20.862 -4.327 -1.391 -0.952 H14 3XO 45 3XO H25 H14 H 0 1 N N N 14.935 13.853 -13.265 2.533 -2.632 3.504 H25 3XO 46 3XO H18 H15 H 0 1 N N N 15.448 25.522 -20.048 -9.257 -2.517 1.083 H18 3XO 47 3XO H17 H16 H 0 1 N N N 15.621 24.493 -18.586 -8.160 -3.749 0.414 H17 3XO 48 3XO H16 H17 H 0 1 N N N 16.293 23.940 -20.157 -7.785 -2.974 1.972 H16 3XO 49 3XO H H18 H 0 1 N N N 10.464 13.368 -16.477 3.279 2.023 0.420 H 3XO 50 3XO H7 H19 H 0 1 N N N 11.818 19.531 -18.442 -2.703 -0.921 -1.240 H7 3XO 51 3XO H5 H20 H 0 1 N N N 12.021 17.271 -18.383 -0.836 1.018 1.029 H5 3XO 52 3XO H4 H21 H 0 1 N N N 11.376 15.106 -17.317 1.612 1.266 1.013 H4 3XO 53 3XO H3 H22 H 0 1 N N N 8.751 12.487 -14.905 5.359 1.962 -0.962 H3 3XO 54 3XO H2 H23 H 0 1 N N N 9.146 13.973 -13.030 5.601 -0.487 -1.118 H2 3XO 55 3XO H1 H24 H 0 1 N N N 11.813 12.536 -12.744 6.274 -0.335 1.858 H1 3XO 56 3XO H19 H25 H 0 1 N N N 11.184 15.425 -13.490 3.878 -1.560 0.412 H19 3XO 57 3XO H23 H26 H 0 1 N N N 13.574 15.590 -13.957 4.489 -1.267 3.388 H23 3XO 58 3XO H24 H27 H 0 1 N N N 13.293 15.124 -12.245 4.677 -2.775 2.461 H24 3XO 59 # 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 3XO N2 C14 SING N N 1 3XO N2 C11 SING N N 2 3XO N2 C12 SING N N 3 3XO C10 C11 SING N N 4 3XO C10 N1 SING N N 5 3XO C13 C12 SING N N 6 3XO C13 N1 SING N N 7 3XO N1 C7 SING N N 8 3XO C7 C6 DOUB N N 9 3XO C7 C8 SING N N 10 3XO N C6 SING N N 11 3XO N C3 SING N N 12 3XO C6 C9 SING N N 13 3XO C8 O1 DOUB N N 14 3XO C8 C9 SING N N 15 3XO C2 C3 DOUB Y N 16 3XO C2 C1 SING Y N 17 3XO C3 C4 SING Y N 18 3XO C9 O2 DOUB N N 19 3XO C1 C DOUB Y N 20 3XO C4 C5 DOUB Y N 21 3XO C C5 SING Y N 22 3XO C O SING N N 23 3XO C5 CL SING N N 24 3XO C15 O SING N N 25 3XO C15 O3 SING N N 26 3XO C15 C19 SING N N 27 3XO O3 C16 SING N N 28 3XO O6 C19 SING N N 29 3XO C19 C18 SING N N 30 3XO C16 C20 SING N N 31 3XO C16 C17 SING N N 32 3XO O7 C20 SING N N 33 3XO C18 C17 SING N N 34 3XO C18 O5 SING N N 35 3XO C17 O4 SING N N 36 3XO C4 H6 SING N N 37 3XO O4 H20 SING N N 38 3XO O5 H21 SING N N 39 3XO C10 H8 SING N N 40 3XO C10 H9 SING N N 41 3XO O6 H22 SING N N 42 3XO C11 H11 SING N N 43 3XO C11 H10 SING N N 44 3XO C12 H12 SING N N 45 3XO C12 H13 SING N N 46 3XO C13 H15 SING N N 47 3XO C13 H14 SING N N 48 3XO O7 H25 SING N N 49 3XO C14 H18 SING N N 50 3XO C14 H17 SING N N 51 3XO C14 H16 SING N N 52 3XO C15 H SING N N 53 3XO N H7 SING N N 54 3XO C2 H5 SING N N 55 3XO C1 H4 SING N N 56 3XO C19 H3 SING N N 57 3XO C18 H2 SING N N 58 3XO C17 H1 SING N N 59 3XO C16 H19 SING N N 60 3XO C20 H23 SING N N 61 3XO C20 H24 SING N N 62 # 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 3XO SMILES ACDLabs 12.01 "O=C2C(N1CCN(C)CC1)=C(C2=O)Nc4ccc(OC3OC(C(O)C(O)C3O)CO)c(Cl)c4" 3XO InChI InChI 1.03 "InChI=1S/C21H26ClN3O8/c1-24-4-6-25(7-5-24)15-14(17(28)18(15)29)23-10-2-3-12(11(22)8-10)32-21-20(31)19(30)16(27)13(9-26)33-21/h2-3,8,13,16,19-21,23,26-27,30-31H,4-7,9H2,1H3/t13-,16-,19+,20+,21+/m1/s1" 3XO InChIKey InChI 1.03 OVFSRWMGARZIAS-YVNBQAQUSA-N 3XO SMILES_CANONICAL CACTVS 3.385 "CN1CCN(CC1)C2=C(Nc3ccc(O[C@H]4O[C@H](CO)[C@@H](O)[C@H](O)[C@@H]4O)c(Cl)c3)C(=O)C2=O" 3XO SMILES CACTVS 3.385 "CN1CCN(CC1)C2=C(Nc3ccc(O[CH]4O[CH](CO)[CH](O)[CH](O)[CH]4O)c(Cl)c3)C(=O)C2=O" 3XO SMILES_CANONICAL "OpenEye OEToolkits" 1.9.2 "CN1CCN(CC1)C2=C(C(=O)C2=O)Nc3ccc(c(c3)Cl)O[C@@H]4[C@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O" 3XO SMILES "OpenEye OEToolkits" 1.9.2 "CN1CCN(CC1)C2=C(C(=O)C2=O)Nc3ccc(c(c3)Cl)OC4C(C(C(C(O4)CO)O)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 3XO "SYSTEMATIC NAME" ACDLabs 12.01 "2-chloro-4-{[2-(4-methylpiperazin-1-yl)-3,4-dioxocyclobut-1-en-1-yl]amino}phenyl alpha-D-mannopyranoside" 3XO "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.9.2 "3-[[3-chloranyl-4-[(2R,3S,4S,5S,6R)-6-(hydroxymethyl)-3,4,5-tris(oxidanyl)oxan-2-yl]oxy-phenyl]amino]-4-(4-methylpiperazin-1-yl)cyclobut-3-ene-1,2-dione" # loop_ _pdbx_chem_comp_audit.comp_id _pdbx_chem_comp_audit.action_type _pdbx_chem_comp_audit.date _pdbx_chem_comp_audit.processing_site 3XO "Create component" 2014-12-06 EBI 3XO "Initial release" 2015-05-20 RCSB #