data_XKL # _chem_comp.id XKL _chem_comp.name "5-[2,4-dihydroxy-6-(4-nitrophenoxy)phenyl]-N-ethyl-1,2-oxazole-3-carboxamide" _chem_comp.type non-polymer _chem_comp.pdbx_type HETAIN _chem_comp.formula "C18 H15 N3 O7" _chem_comp.mon_nstd_parent_comp_id ? _chem_comp.pdbx_synonyms ? _chem_comp.pdbx_formal_charge 0 _chem_comp.pdbx_initial_date 2013-05-30 _chem_comp.pdbx_modified_date 2014-09-05 _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 385.328 _chem_comp.one_letter_code ? _chem_comp.three_letter_code XKL _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 4BQJ _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 XKL O28 O28 O 0 1 N N N 0.462 4.343 9.892 5.316 -0.545 1.656 O28 XKL 1 XKL C24 C24 C 0 1 N N N 0.727 4.465 11.085 4.921 -0.896 0.561 C24 XKL 2 XKL N25 N25 N 0 1 N N N -0.203 4.700 12.020 5.624 -1.798 -0.151 N25 XKL 3 XKL C26 C26 C 0 1 N N N -1.650 4.889 11.877 6.864 -2.357 0.394 C26 XKL 4 XKL C27 C27 C 0 1 N N N -2.380 3.571 11.725 7.459 -3.350 -0.607 C27 XKL 5 XKL C22 C22 C 0 1 Y N N 2.153 4.344 11.532 3.663 -0.334 0.012 C22 XKL 6 XKL N21 N21 N 0 1 Y N N 2.656 4.911 12.654 3.116 -0.616 -1.146 N21 XKL 7 XKL O20 O20 O 0 1 Y N N 4.033 4.533 12.671 2.089 -0.002 -1.319 O20 XKL 8 XKL C23 C23 C 0 1 Y N N 3.179 3.656 10.861 2.809 0.609 0.638 C23 XKL 9 XKL C19 C19 C 0 1 Y N N 4.353 3.782 11.597 1.804 0.795 -0.274 C19 XKL 10 XKL C5 C5 C 0 1 Y N N 5.696 3.233 11.319 0.637 1.686 -0.134 C5 XKL 11 XKL C4 C4 C 0 1 Y N N 6.804 4.036 11.497 0.816 3.075 -0.073 C4 XKL 12 XKL O7 O7 O 0 1 N N N 6.619 5.334 11.889 2.065 3.604 -0.143 O7 XKL 13 XKL C3 C3 C 0 1 Y N N 8.078 3.527 11.240 -0.283 3.906 0.057 C3 XKL 14 XKL C2 C2 C 0 1 Y N N 8.219 2.197 10.818 -1.560 3.367 0.128 C2 XKL 15 XKL O8 O8 O 0 1 N N N 9.464 1.705 10.567 -2.634 4.188 0.257 O8 XKL 16 XKL C6 C6 C 0 1 Y N N 5.808 1.915 10.923 -0.656 1.150 -0.068 C6 XKL 17 XKL C1 C1 C 0 1 Y N N 7.089 1.384 10.662 -1.745 1.992 0.068 C1 XKL 18 XKL O9 O9 O 0 1 N N N 4.639 1.195 10.770 -0.839 -0.194 -0.131 O9 XKL 19 XKL C10 C10 C 0 1 Y N N 4.626 0.165 9.880 -2.110 -0.669 -0.069 C10 XKL 20 XKL C15 C15 C 0 1 Y N N 5.071 0.381 8.578 -2.844 -0.843 -1.234 C15 XKL 21 XKL C14 C14 C 0 1 Y N N 5.111 -0.673 7.674 -4.137 -1.325 -1.168 C14 XKL 22 XKL C13 C13 C 0 1 Y N N 4.691 -1.948 8.063 -4.700 -1.634 0.056 C13 XKL 23 XKL N16 N16 N 1 1 N N N 4.779 -3.003 7.131 -6.086 -2.150 0.124 N16 XKL 24 XKL O18 O18 O -1 1 N N N 5.592 -2.885 6.213 -6.729 -2.303 -0.899 O18 XKL 25 XKL O17 O17 O 0 1 N N N 4.145 -4.045 7.254 -6.582 -2.422 1.202 O17 XKL 26 XKL C12 C12 C 0 1 Y N N 4.247 -2.160 9.373 -3.970 -1.461 1.218 C12 XKL 27 XKL C11 C11 C 0 1 Y N N 4.210 -1.101 10.295 -2.675 -0.985 1.158 C11 XKL 28 XKL H25 H25 H 0 1 N N N 0.142 4.755 12.957 5.308 -2.078 -1.025 H25 XKL 29 XKL H261 H261 H 0 0 N N N -2.031 5.405 12.770 7.576 -1.553 0.574 H261 XKL 30 XKL H262 H262 H 0 0 N N N -1.842 5.506 10.987 6.650 -2.871 1.331 H262 XKL 31 XKL H271 H271 H 0 0 N N N -3.459 3.759 11.621 6.746 -4.155 -0.788 H271 XKL 32 XKL H272 H272 H 0 0 N N N -2.011 3.049 10.830 7.673 -2.836 -1.545 H272 XKL 33 XKL H273 H273 H 0 0 N N N -2.200 2.948 12.613 8.381 -3.766 -0.202 H273 XKL 34 XKL H23 H23 H 0 1 N N N 3.074 3.119 9.930 2.925 1.074 1.606 H23 XKL 35 XKL H7 H7 H 0 1 N N N 7.462 5.764 11.971 2.357 3.805 -1.042 H7 XKL 36 XKL H3 H3 H 0 1 N N N 8.949 4.153 11.365 -0.146 4.976 0.104 H3 XKL 37 XKL H8 H8 H 0 1 N N N 9.397 0.798 10.292 -3.014 4.473 -0.585 H8 XKL 38 XKL H1 H1 H 0 1 N N N 7.198 0.358 10.344 -2.742 1.580 0.124 H1 XKL 39 XKL H15 H15 H 0 1 N N N 5.385 1.368 8.271 -2.405 -0.602 -2.191 H15 XKL 40 XKL H11 H11 H 0 1 N N N 3.866 -1.263 11.306 -2.105 -0.854 2.065 H11 XKL 41 XKL H14 H14 H 0 1 N N N 5.468 -0.507 6.668 -4.709 -1.461 -2.075 H14 XKL 42 XKL H12 H12 H 0 1 N N N 3.930 -3.146 9.678 -4.412 -1.703 2.174 H12 XKL 43 # 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 XKL O28 C24 DOUB N N 1 XKL C24 N25 SING N N 2 XKL C24 C22 SING N N 3 XKL N25 C26 SING N N 4 XKL C26 C27 SING N N 5 XKL C22 N21 DOUB Y N 6 XKL C22 C23 SING Y N 7 XKL N21 O20 SING Y N 8 XKL O20 C19 SING Y N 9 XKL C23 C19 DOUB Y N 10 XKL C19 C5 SING N N 11 XKL C5 C4 SING Y N 12 XKL C5 C6 DOUB Y N 13 XKL C4 O7 SING N N 14 XKL C4 C3 DOUB Y N 15 XKL C3 C2 SING Y N 16 XKL C2 O8 SING N N 17 XKL C2 C1 DOUB Y N 18 XKL C6 C1 SING Y N 19 XKL C6 O9 SING N N 20 XKL O9 C10 SING N N 21 XKL C10 C15 SING Y N 22 XKL C10 C11 DOUB Y N 23 XKL C15 C14 DOUB Y N 24 XKL C14 C13 SING Y N 25 XKL C13 N16 SING N N 26 XKL C13 C12 DOUB Y N 27 XKL N16 O18 SING N N 28 XKL N16 O17 DOUB N N 29 XKL C12 C11 SING Y N 30 XKL N25 H25 SING N N 31 XKL C26 H261 SING N N 32 XKL C26 H262 SING N N 33 XKL C27 H271 SING N N 34 XKL C27 H272 SING N N 35 XKL C27 H273 SING N N 36 XKL C23 H23 SING N N 37 XKL O7 H7 SING N N 38 XKL C3 H3 SING N N 39 XKL O8 H8 SING N N 40 XKL C1 H1 SING N N 41 XKL C15 H15 SING N N 42 XKL C11 H11 SING N N 43 XKL C14 H14 SING N N 44 XKL C12 H12 SING N N 45 # 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 XKL SMILES ACDLabs 12.01 "O=C(c3noc(c2c(Oc1ccc([N+]([O-])=O)cc1)cc(O)cc2O)c3)NCC" XKL InChI InChI 1.03 "InChI=1S/C18H15N3O7/c1-2-19-18(24)13-9-16(28-20-13)17-14(23)7-11(22)8-15(17)27-12-5-3-10(4-6-12)21(25)26/h3-9,22-23H,2H2,1H3,(H,19,24)" XKL InChIKey InChI 1.03 DAESMMVDEWYEKZ-UHFFFAOYSA-N XKL SMILES_CANONICAL CACTVS 3.385 "CCNC(=O)c1cc(on1)c2c(O)cc(O)cc2Oc3ccc(cc3)[N+]([O-])=O" XKL SMILES CACTVS 3.385 "CCNC(=O)c1cc(on1)c2c(O)cc(O)cc2Oc3ccc(cc3)[N+]([O-])=O" XKL SMILES_CANONICAL "OpenEye OEToolkits" 1.9.2 "CCNC(=O)c1cc(on1)c2c(cc(cc2Oc3ccc(cc3)[N+](=O)[O-])O)O" XKL SMILES "OpenEye OEToolkits" 1.9.2 "CCNC(=O)c1cc(on1)c2c(cc(cc2Oc3ccc(cc3)[N+](=O)[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 XKL "SYSTEMATIC NAME" ACDLabs 12.01 "5-[2,4-dihydroxy-6-(4-nitrophenoxy)phenyl]-N-ethyl-1,2-oxazole-3-carboxamide" XKL "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.9.2 "N-ethyl-5-[2-(4-nitrophenoxy)-4,6-bis(oxidanyl)phenyl]-1,2-oxazole-3-carboxamide" # loop_ _pdbx_chem_comp_audit.comp_id _pdbx_chem_comp_audit.action_type _pdbx_chem_comp_audit.date _pdbx_chem_comp_audit.processing_site XKL "Create component" 2013-05-30 EBI XKL "Initial release" 2013-10-23 RCSB XKL "Modify descriptor" 2014-09-05 RCSB #