data_9UN # _chem_comp.id 9UN _chem_comp.name "5-[2,4-dihydroxy-6-(4-nitrophenoxy)phenyl]-N-(1-methylpiperidin-4-yl)-1,2-oxazole-3-carboxamide" _chem_comp.type NON-POLYMER _chem_comp.pdbx_type HETAIN _chem_comp.formula "C22 H22 N4 O7" _chem_comp.mon_nstd_parent_comp_id ? _chem_comp.pdbx_synonyms ? _chem_comp.pdbx_formal_charge 0 _chem_comp.pdbx_initial_date 2012-08-21 _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 454.433 _chem_comp.one_letter_code ? _chem_comp.three_letter_code 9UN _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 4B7P _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 9UN C1 C1 C 0 1 Y N N 8.057 3.837 11.051 2.439 -4.005 0.083 C1 9UN 1 9UN C2 C2 C 0 1 Y N N 6.814 4.337 11.423 1.213 -3.384 -0.073 C2 9UN 2 9UN C3 C3 C 0 1 Y N N 5.693 3.570 11.241 1.144 -1.986 -0.152 C3 9UN 3 9UN C4 C4 C 0 1 Y N N 5.774 2.276 10.782 2.320 -1.228 -0.070 C4 9UN 4 9UN C5 C5 C 0 1 Y N N 7.019 1.721 10.456 3.540 -1.863 0.087 C5 9UN 5 9UN C6 C6 C 0 1 Y N N 8.146 2.529 10.598 3.600 -3.248 0.163 C6 9UN 6 9UN O7 O7 O 0 1 N N N 9.340 2.001 10.255 4.800 -3.865 0.317 O7 9UN 7 9UN O8 O8 O 0 1 N N N 6.720 5.628 11.866 0.079 -4.126 -0.152 O8 9UN 8 9UN O9 O9 O 0 1 N N N 4.644 1.550 10.718 2.263 0.126 -0.145 O9 9UN 9 9UN C10 C10 C 0 1 Y N N 4.416 0.723 9.672 3.430 0.819 -0.074 C10 9UN 10 9UN C11 C11 C 0 1 Y N N 4.648 1.109 8.346 4.137 1.112 -1.232 C11 9UN 11 9UN C12 C12 C 0 1 Y N N 4.359 0.172 7.352 5.323 1.816 -1.156 C12 9UN 12 9UN C13 C13 C 0 1 Y N N 3.885 -1.089 7.739 5.806 2.229 0.072 C13 9UN 13 9UN C14 C14 C 0 1 Y N N 3.635 -1.433 9.045 5.104 1.938 1.227 C14 9UN 14 9UN C15 C15 C 0 1 Y N N 3.937 -0.533 10.052 3.914 1.240 1.157 C15 9UN 15 9UN N16 N16 N 1 1 N N N 3.542 -2.066 6.805 7.077 2.983 0.150 N16 9UN 16 9UN O17 O17 O 0 1 N N N 3.725 -3.257 7.045 7.697 3.239 -0.867 O17 9UN 17 9UN O18 O18 O -1 1 N N N 3.018 -1.662 5.777 7.504 3.347 1.231 O18 9UN 18 9UN C19 C19 C 0 1 Y N N 4.391 4.141 11.594 -0.159 -1.316 -0.319 C19 9UN 19 9UN O20 O20 O 0 1 Y N N 4.163 4.895 12.670 -0.565 -0.595 -1.379 O20 9UN 20 9UN N21 N21 N 0 1 Y N N 2.736 5.306 12.681 -1.686 -0.169 -1.228 N21 9UN 21 9UN C22 C22 C 0 1 Y N N 2.212 4.735 11.603 -2.192 -0.530 -0.073 C22 9UN 22 9UN C23 C23 C 0 1 Y N N 3.191 4.040 10.893 -1.199 -1.310 0.572 C23 9UN 23 9UN C24 C24 C 0 1 N N N 0.781 4.847 11.211 -3.538 -0.193 0.452 C24 9UN 24 9UN O25 O25 O 0 1 N N N 0.490 4.725 10.021 -3.882 -0.595 1.546 O25 9UN 25 9UN N26 N26 N 0 1 N N N -0.090 5.050 12.209 -4.380 0.559 -0.285 N26 9UN 26 9UN C27 C27 C 0 1 N N N -1.529 5.151 11.985 -5.709 0.891 0.233 C27 9UN 27 9UN C28 C28 C 0 1 N N N -1.997 3.710 11.765 -6.205 2.183 -0.422 C28 9UN 28 9UN C29 C29 C 0 1 N N N -3.529 3.644 11.736 -7.619 2.493 0.077 C29 9UN 29 9UN N30 N30 N 0 1 N N N -4.049 4.142 13.009 -8.513 1.377 -0.259 N30 9UN 30 9UN C31 C31 C 0 1 N N N -3.692 5.572 13.166 -8.083 0.136 0.397 C31 9UN 31 9UN C32 C32 C 0 1 N N N -2.155 5.723 13.290 -6.684 -0.244 -0.093 C32 9UN 32 9UN C33 C33 C 0 1 N N N -5.542 3.960 13.001 -9.905 1.698 0.081 C33 9UN 33 9UN H1 H1 H 0 1 N N N 8.939 4.457 11.114 2.493 -5.082 0.148 H1 9UN 34 9UN H5 H5 H 0 1 N N N 7.102 0.702 10.107 4.447 -1.280 0.149 H5 9UN 35 9UN HO7 HO7 H 0 1 N N N 9.219 1.103 9.969 5.237 -4.088 -0.516 HO7 9UN 36 9UN HO8 HO8 H 0 1 N N N 5.816 5.824 12.081 -0.340 -4.297 0.703 HO8 9UN 37 9UN H11 H11 H 0 1 N N N 5.033 2.088 8.103 3.760 0.789 -2.191 H11 9UN 38 9UN H12 H12 H 0 1 N N N 4.498 0.413 6.308 5.873 2.044 -2.057 H12 9UN 39 9UN H14 H14 H 0 1 N N N 3.207 -2.396 9.284 5.484 2.261 2.185 H14 9UN 40 9UN H15 H15 H 0 1 N N N 3.807 -0.792 11.092 3.364 1.017 2.059 H15 9UN 41 9UN H23 H23 H 0 1 N N N 3.044 3.514 9.961 -1.251 -1.786 1.540 H23 9UN 42 9UN HN26 HN26 H 0 0 N N N 0.259 5.136 13.142 -4.106 0.879 -1.159 HN26 9UN 43 9UN H27 H27 H 0 1 N N N -1.774 5.786 11.121 -5.655 1.028 1.313 H27 9UN 44 9UN H28 H28 H 0 1 N N N -1.600 3.342 10.807 -5.539 3.004 -0.159 H28 9UN 45 9UN H28A H28A H 0 0 N N N -1.622 3.078 12.584 -6.221 2.059 -1.505 H28A 9UN 46 9UN H29 H29 H 0 1 N N N -3.910 4.266 10.913 -7.600 2.630 1.158 H29 9UN 47 9UN H29A H29A H 0 0 N N N -3.851 2.603 11.588 -7.980 3.404 -0.399 H29A 9UN 48 9UN H31 H31 H 0 1 N N N -4.044 6.134 12.288 -8.062 0.284 1.477 H31 9UN 49 9UN H31A H31A H 0 0 N N N -4.172 5.970 14.072 -8.783 -0.664 0.154 H31A 9UN 50 9UN H32 H32 H 0 1 N N N -1.790 5.159 14.161 -6.707 -0.406 -1.170 H32 9UN 51 9UN H32A H32A H 0 0 N N N -1.889 6.784 13.402 -6.359 -1.157 0.407 H32A 9UN 52 9UN H33 H33 H 0 1 N N N -5.962 4.327 13.949 -10.222 2.580 -0.476 H33 9UN 53 9UN H33A H33A H 0 0 N N N -5.976 4.527 12.164 -10.546 0.855 -0.178 H33A 9UN 54 9UN H33B H33B H 0 0 N N N -5.781 2.893 12.883 -9.981 1.897 1.150 H33B 9UN 55 # 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 9UN C1 C2 DOUB Y N 1 9UN C1 C6 SING Y N 2 9UN C2 C3 SING Y N 3 9UN C2 O8 SING N N 4 9UN C3 C4 DOUB Y N 5 9UN C3 C19 SING N N 6 9UN C4 C5 SING Y N 7 9UN C4 O9 SING N N 8 9UN C5 C6 DOUB Y N 9 9UN C6 O7 SING N N 10 9UN O9 C10 SING N N 11 9UN C10 C11 DOUB Y N 12 9UN C10 C15 SING Y N 13 9UN C11 C12 SING Y N 14 9UN C12 C13 DOUB Y N 15 9UN C13 C14 SING Y N 16 9UN C13 N16 SING N N 17 9UN C14 C15 DOUB Y N 18 9UN N16 O17 DOUB N N 19 9UN N16 O18 SING N N 20 9UN C19 O20 SING Y N 21 9UN C19 C23 DOUB Y N 22 9UN O20 N21 SING Y N 23 9UN N21 C22 DOUB Y N 24 9UN C22 C23 SING Y N 25 9UN C22 C24 SING N N 26 9UN C24 O25 DOUB N N 27 9UN C24 N26 SING N N 28 9UN N26 C27 SING N N 29 9UN C27 C28 SING N N 30 9UN C27 C32 SING N N 31 9UN C28 C29 SING N N 32 9UN C29 N30 SING N N 33 9UN N30 C31 SING N N 34 9UN N30 C33 SING N N 35 9UN C31 C32 SING N N 36 9UN C1 H1 SING N N 37 9UN C5 H5 SING N N 38 9UN O7 HO7 SING N N 39 9UN O8 HO8 SING N N 40 9UN C11 H11 SING N N 41 9UN C12 H12 SING N N 42 9UN C14 H14 SING N N 43 9UN C15 H15 SING N N 44 9UN C23 H23 SING N N 45 9UN N26 HN26 SING N N 46 9UN C27 H27 SING N N 47 9UN C28 H28 SING N N 48 9UN C28 H28A SING N N 49 9UN C29 H29 SING N N 50 9UN C29 H29A SING N N 51 9UN C31 H31 SING N N 52 9UN C31 H31A SING N N 53 9UN C32 H32 SING N N 54 9UN C32 H32A SING N N 55 9UN C33 H33 SING N N 56 9UN C33 H33A SING N N 57 9UN C33 H33B SING N N 58 # 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 9UN SMILES ACDLabs 12.01 "O=C(c3noc(c2c(Oc1ccc([N+]([O-])=O)cc1)cc(O)cc2O)c3)NC4CCN(C)CC4" 9UN InChI InChI 1.03 "InChI=1S/C22H22N4O7/c1-25-8-6-13(7-9-25)23-22(29)17-12-20(33-24-17)21-18(28)10-15(27)11-19(21)32-16-4-2-14(3-5-16)26(30)31/h2-5,10-13,27-28H,6-9H2,1H3,(H,23,29)" 9UN InChIKey InChI 1.03 YLQODGGPIHWTHR-UHFFFAOYSA-N 9UN SMILES_CANONICAL CACTVS 3.385 "CN1CCC(CC1)NC(=O)c2cc(on2)c3c(O)cc(O)cc3Oc4ccc(cc4)[N+]([O-])=O" 9UN SMILES CACTVS 3.385 "CN1CCC(CC1)NC(=O)c2cc(on2)c3c(O)cc(O)cc3Oc4ccc(cc4)[N+]([O-])=O" 9UN SMILES_CANONICAL "OpenEye OEToolkits" 1.9.2 "CN1CCC(CC1)NC(=O)c2cc(on2)c3c(cc(cc3Oc4ccc(cc4)[N+](=O)[O-])O)O" 9UN SMILES "OpenEye OEToolkits" 1.9.2 "CN1CCC(CC1)NC(=O)c2cc(on2)c3c(cc(cc3Oc4ccc(cc4)[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 9UN "SYSTEMATIC NAME" ACDLabs 12.01 "5-[2,4-dihydroxy-6-(4-nitrophenoxy)phenyl]-N-(1-methylpiperidin-4-yl)-1,2-oxazole-3-carboxamide" 9UN "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.9.2 "N-(1-methylpiperidin-4-yl)-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 9UN "Create component" 2012-08-21 EBI 9UN "Initial release" 2013-05-29 RCSB 9UN "Modify descriptor" 2014-09-05 RCSB #