data_AWH # _chem_comp.id AWH _chem_comp.name "3-[(Z)-[(5Z)-5-[[2-(2-hydroxy-2-oxoethyloxy)phenyl]methylidene]-3-methyl-4-oxidanylidene-1,3-thiazolidin-2-ylidene]amino]benzoic acid" _chem_comp.type non-polymer _chem_comp.pdbx_type HETAIN _chem_comp.formula "C20 H16 N2 O6 S" _chem_comp.mon_nstd_parent_comp_id ? _chem_comp.pdbx_synonyms "3-((Z)-((Z)-5-(2(carboxymethoxy)benzylidene)-3-methyl-4-oxothiazolidin-2-ylidene)amino)benzoic acid" _chem_comp.pdbx_formal_charge 0 _chem_comp.pdbx_initial_date 2012-12-05 _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 412.416 _chem_comp.one_letter_code ? _chem_comp.three_letter_code AWH _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 3ZEI _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 AWH O5 O5 O 0 1 N N N -18.669 4.304 -6.710 -6.878 0.156 -2.133 O5 AWH 1 AWH C19 C19 C 0 1 N N N -18.705 5.411 -6.149 -6.544 1.036 -1.366 C19 AWH 2 AWH O6 O6 O 0 1 N N N -17.868 6.381 -6.560 -7.220 2.201 -1.341 O6 AWH 3 AWH C18 C18 C 0 1 Y N N -19.584 5.709 -4.937 -5.400 0.826 -0.454 C18 AWH 4 AWH C17 C17 C 0 1 Y N N -20.512 4.816 -4.370 -5.014 1.838 0.429 C17 AWH 5 AWH C16 C16 C 0 1 Y N N -21.256 5.175 -3.235 -3.946 1.644 1.282 C16 AWH 6 AWH C15 C15 C 0 1 Y N N -21.059 6.434 -2.632 -3.251 0.451 1.268 C15 AWH 7 AWH C20 C20 C 0 1 Y N N -19.395 6.940 -4.335 -4.707 -0.382 -0.470 C20 AWH 8 AWH C14 C14 C 0 1 Y N N -20.117 7.308 -3.204 -3.625 -0.569 0.390 C14 AWH 9 AWH N2 N2 N 0 1 N N N -19.849 8.540 -2.725 -2.935 -1.751 0.377 N2 AWH 10 AWH C13 C13 C 0 1 N N N -20.161 9.676 -3.408 -1.621 -1.745 0.394 C13 AWH 11 AWH N1 N1 N 0 1 N N N -19.850 10.892 -2.907 -0.800 -2.839 0.385 N1 AWH 12 AWH C1 C1 C 0 1 N N N -19.138 11.149 -1.619 -1.359 -4.192 0.353 C1 AWH 13 AWH S S S 0 1 N N N -20.962 9.705 -4.910 -0.570 -0.319 0.426 S AWH 14 AWH C3 C3 C 0 1 N N N -20.955 11.384 -4.945 0.940 -1.249 0.432 C3 AWH 15 AWH C2 C2 C 0 1 N N N -20.301 11.821 -3.792 0.509 -2.650 0.404 C2 AWH 16 AWH O1 O1 O 0 1 N N N -20.146 13.074 -3.573 1.301 -3.575 0.398 O1 AWH 17 AWH C4 C4 C 0 1 N N N -21.527 12.177 -6.070 2.211 -0.771 0.454 C4 AWH 18 AWH C5 C5 C 0 1 Y N N -22.231 11.625 -7.264 2.450 0.668 0.621 C5 AWH 19 AWH C10 C10 C 0 1 Y N N -23.302 12.375 -7.761 3.682 1.227 0.244 C10 AWH 20 AWH O2 O2 O 0 1 N N N -23.609 13.551 -7.110 4.658 0.440 -0.278 O2 AWH 21 AWH C11 C11 C 0 1 N N N -23.970 14.769 -7.760 5.884 1.080 -0.638 C11 AWH 22 AWH C12 C12 C 0 1 N N N -25.231 15.256 -7.080 6.840 0.056 -1.195 C12 AWH 23 AWH O4 O4 O 0 1 N N N -26.440 14.908 -7.516 8.063 0.431 -1.602 O4 AWH 24 AWH O3 O3 O 0 1 N N N -25.156 15.972 -6.099 6.505 -1.102 -1.275 O3 AWH 25 AWH C9 C9 C 0 1 Y N N -24.039 11.928 -8.875 3.897 2.586 0.406 C9 AWH 26 AWH C8 C8 C 0 1 Y N N -23.695 10.724 -9.504 2.903 3.387 0.936 C8 AWH 27 AWH C7 C7 C 0 1 Y N N -22.620 9.973 -9.005 1.686 2.840 1.310 C7 AWH 28 AWH C6 C6 C 0 1 Y N N -21.892 10.415 -7.889 1.451 1.491 1.151 C6 AWH 29 AWH H6 H6 H 0 1 N N N -17.331 6.055 -7.272 -7.964 2.290 -1.953 H6 AWH 30 AWH H17 H17 H 0 1 N N N -20.654 3.842 -4.814 -5.553 2.774 0.445 H17 AWH 31 AWH H20 H20 H 0 1 N N N -18.674 7.628 -4.751 -5.004 -1.169 -1.148 H20 AWH 32 AWH H16 H16 H 0 1 N N N -21.979 4.487 -2.824 -3.652 2.429 1.962 H16 AWH 33 AWH H15 H15 H 0 1 N N N -21.617 6.720 -1.753 -2.416 0.306 1.938 H15 AWH 34 AWH H11C H11C H 0 0 N N N -19.025 12.233 -1.472 -1.484 -4.510 -0.682 H11C AWH 35 AWH H12C H12C H 0 0 N N N -19.720 10.725 -0.787 -0.681 -4.877 0.863 H12C AWH 36 AWH H13C H13C H 0 0 N N N -18.145 10.677 -1.649 -2.326 -4.198 0.855 H13C AWH 37 AWH H4C H4C H 0 1 N N N -21.422 13.251 -6.016 3.045 -1.449 0.349 H4C AWH 38 AWH HA HA H 0 1 N N N -21.071 9.824 -7.511 0.499 1.070 1.439 HA AWH 39 AWH H9 H9 H 0 1 N N N -24.869 12.513 -9.244 4.843 3.020 0.117 H9 AWH 40 AWH H111 H111 H 0 0 N N N -23.167 15.512 -7.650 5.688 1.842 -1.392 H111 AWH 41 AWH H112 H112 H 0 0 N N N -24.159 14.589 -8.829 6.324 1.546 0.244 H112 AWH 42 AWH H4 H4 H 0 1 N N N -27.103 15.298 -6.958 8.640 -0.261 -1.951 H4 AWH 43 AWH H8 H8 H 0 1 N N N -24.251 10.378 -10.363 3.076 4.445 1.060 H8 AWH 44 AWH H7 H7 H 0 1 N N N -22.349 9.044 -9.485 0.916 3.474 1.724 H7 AWH 45 # # 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 AWH O5 C19 DOUB N N 1 AWH C19 O6 SING N N 2 AWH C19 C18 SING N N 3 AWH C18 C17 SING Y N 4 AWH C18 C20 DOUB Y N 5 AWH C17 C16 DOUB Y N 6 AWH C16 C15 SING Y N 7 AWH C15 C14 DOUB Y N 8 AWH C20 C14 SING Y N 9 AWH C14 N2 SING N N 10 AWH N2 C13 DOUB N N 11 AWH C13 N1 SING N N 12 AWH C13 S SING N N 13 AWH N1 C1 SING N N 14 AWH N1 C2 SING N N 15 AWH S C3 SING N N 16 AWH C3 C2 SING N N 17 AWH C3 C4 DOUB N Z 18 AWH C2 O1 DOUB N N 19 AWH C4 C5 SING N N 20 AWH C5 C10 SING Y N 21 AWH C5 C6 DOUB Y N 22 AWH C10 O2 SING N N 23 AWH C10 C9 DOUB Y N 24 AWH O2 C11 SING N N 25 AWH C11 C12 SING N N 26 AWH C12 O4 SING N N 27 AWH C12 O3 DOUB N N 28 AWH C9 C8 SING Y N 29 AWH C8 C7 DOUB Y N 30 AWH C7 C6 SING Y N 31 AWH O6 H6 SING N N 32 AWH C17 H17 SING N N 33 AWH C20 H20 SING N N 34 AWH C16 H16 SING N N 35 AWH C15 H15 SING N N 36 AWH C1 H11C SING N N 37 AWH C1 H12C SING N N 38 AWH C1 H13C SING N N 39 AWH C4 H4C SING N N 40 AWH C6 HA SING N N 41 AWH C9 H9 SING N N 42 AWH C11 H111 SING N N 43 AWH C11 H112 SING N N 44 AWH O4 H4 SING N N 45 AWH C8 H8 SING N N 46 AWH C7 H7 SING N N 47 # # 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 AWH SMILES ACDLabs 12.01 "O=C(O)COc1ccccc1\C=C3/S/C(=N\c2cccc(C(=O)O)c2)N(C3=O)C" AWH InChI InChI 1.03 "InChI=1S/C20H16N2O6S/c1-22-18(25)16(10-12-5-2-3-8-15(12)28-11-17(23)24)29-20(22)21-14-7-4-6-13(9-14)19(26)27/h2-10H,11H2,1H3,(H,23,24)(H,26,27)/b16-10-,21-20-" AWH InChIKey InChI 1.03 ZRWLYRDALGQUID-PTWQKYQPSA-N AWH SMILES_CANONICAL CACTVS 3.385 "CN1C(=O)C(/SC1=Nc2cccc(c2)C(O)=O)=C/c3ccccc3OCC(O)=O" AWH SMILES CACTVS 3.385 "CN1C(=O)C(SC1=Nc2cccc(c2)C(O)=O)=Cc3ccccc3OCC(O)=O" AWH SMILES_CANONICAL "OpenEye OEToolkits" 1.9.2 "CN\1C(=O)/C(=C/c2ccccc2OCC(=O)O)/S/C1=N\c3cccc(c3)C(=O)O" AWH SMILES "OpenEye OEToolkits" 1.9.2 "CN1C(=O)C(=Cc2ccccc2OCC(=O)O)SC1=Nc3cccc(c3)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 AWH "SYSTEMATIC NAME" ACDLabs 12.01 "3-[(Z)-{(5Z)-5-[2-(carboxymethoxy)benzylidene]-3-methyl-4-oxo-1,3-thiazolidin-2-ylidene}amino]benzoic acid" AWH "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.9.2 "3-[(Z)-[(5Z)-5-[[2-(2-hydroxy-2-oxoethyloxy)phenyl]methylidene]-3-methyl-4-oxidanylidene-1,3-thiazolidin-2-ylidene]amino]benzoic 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 AWH "Create component" 2012-12-05 EBI AWH "Other modification" 2012-12-10 EBI AWH "Initial release" 2013-08-07 RCSB AWH "Modify descriptor" 2014-09-05 RCSB AWH "Modify synonyms" 2021-03-01 PDBE # _pdbx_chem_comp_synonyms.ordinal 1 _pdbx_chem_comp_synonyms.comp_id AWH _pdbx_chem_comp_synonyms.name "3-((Z)-((Z)-5-(2(carboxymethoxy)benzylidene)-3-methyl-4-oxothiazolidin-2-ylidene)amino)benzoic acid" _pdbx_chem_comp_synonyms.provenance ? _pdbx_chem_comp_synonyms.type ? ##