data_DWB # _chem_comp.id DWB _chem_comp.name "(4S)-2'-(5-chloro-2-fluorophenyl)-7'-methoxyspiro[1,3-oxazole-4,9'-xanthen]-2-amine" _chem_comp.type NON-POLYMER _chem_comp.pdbx_type HETAIN _chem_comp.formula "C22 H16 Cl F N2 O3" _chem_comp.mon_nstd_parent_comp_id ? _chem_comp.pdbx_synonyms ? _chem_comp.pdbx_formal_charge 0 _chem_comp.pdbx_initial_date 2012-07-03 _chem_comp.pdbx_modified_date 2012-09-07 _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 410.825 _chem_comp.one_letter_code ? _chem_comp.three_letter_code DWB _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 4FRJ _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 DWB F26 F26 F 0 1 N N N 26.310 47.173 77.456 -3.356 -2.693 -1.593 F26 DWB 1 DWB C20 C20 C 0 1 Y N N 27.021 47.036 78.591 -3.936 -1.611 -1.030 C20 DWB 2 DWB C21 C21 C 0 1 Y N N 26.549 46.147 79.549 -5.253 -1.301 -1.317 C21 DWB 3 DWB C22 C22 C 0 1 Y N N 27.264 45.962 80.730 -5.847 -0.194 -0.741 C22 DWB 4 DWB C23 C23 C 0 1 Y N N 28.434 46.668 80.956 -5.128 0.611 0.126 C23 DWB 5 DWB CL2 CL2 CL 0 0 N N N 29.317 46.415 82.435 -5.882 2.000 0.844 CL2 DWB 6 DWB C24 C24 C 0 1 Y N N 28.902 47.566 80.003 -3.812 0.312 0.421 C24 DWB 7 DWB C14 C14 C 0 1 Y N N 28.203 47.760 78.808 -3.209 -0.806 -0.152 C14 DWB 8 DWB C12 C12 C 0 1 Y N N 28.704 48.645 77.843 -1.798 -1.136 0.166 C12 DWB 9 DWB C13 C13 C 0 1 Y N N 30.061 48.612 77.534 -0.813 -0.155 0.074 C13 DWB 10 DWB C8 C8 C 0 1 Y N N 30.606 49.459 76.579 0.500 -0.461 0.369 C8 DWB 11 DWB C11 C11 C 0 1 Y N N 27.884 49.541 77.168 -1.455 -2.426 0.564 C11 DWB 12 DWB C10 C10 C 0 1 Y N N 28.413 50.397 76.221 -0.143 -2.727 0.859 C10 DWB 13 DWB C9 C9 C 0 1 Y N N 29.762 50.367 75.921 0.841 -1.749 0.761 C9 DWB 14 DWB O25 O25 O 0 1 N N N 30.180 51.218 74.972 2.123 -2.068 1.058 O25 DWB 15 DWB C4 C4 C 0 1 Y N N 31.496 51.266 74.649 3.145 -1.306 0.598 C4 DWB 16 DWB C3 C3 C 0 1 Y N N 31.891 52.200 73.690 4.423 -1.848 0.535 C3 DWB 17 DWB C2 C2 C 0 1 Y N N 33.230 52.320 73.300 5.478 -1.089 0.069 C2 DWB 18 DWB C1 C1 C 0 1 Y N N 34.202 51.496 73.882 5.262 0.220 -0.338 C1 DWB 19 DWB O28 O28 O 0 1 N N N 35.546 51.537 73.553 6.300 0.969 -0.797 O28 DWB 20 DWB C29 C29 C 0 1 N N N 35.941 52.435 72.511 7.585 0.345 -0.833 C29 DWB 21 DWB C6 C6 C 0 1 Y N N 33.795 50.566 74.831 3.988 0.762 -0.276 C6 DWB 22 DWB C5 C5 C 0 1 Y N N 32.462 50.427 75.220 2.930 0.002 0.190 C5 DWB 23 DWB C7 C7 C 0 1 N N S 32.110 49.387 76.273 1.554 0.600 0.260 C7 DWB 24 DWB C18 C18 C 0 1 N N N 32.524 47.972 75.820 1.459 1.591 1.438 C18 DWB 25 DWB O17 O17 O 0 1 N N N 33.569 47.523 76.777 0.649 2.637 0.862 O17 DWB 26 DWB C16 C16 C 0 1 N N N 33.789 48.564 77.653 0.797 2.582 -0.477 C16 DWB 27 DWB N19 N19 N 0 1 N N N 34.705 48.496 78.622 0.452 3.615 -1.314 N19 DWB 28 DWB N15 N15 N 0 1 N N N 32.985 49.616 77.453 1.297 1.460 -0.904 N15 DWB 29 DWB H1 H1 H 0 1 N N N 25.632 45.602 79.379 -5.818 -1.926 -1.993 H1 DWB 30 DWB H2 H2 H 0 1 N N N 26.905 45.265 81.473 -6.875 0.044 -0.969 H2 DWB 31 DWB H3 H3 H 0 1 N N N 29.812 48.118 80.187 -3.253 0.941 1.098 H3 DWB 32 DWB H4 H4 H 0 1 N N N 30.703 47.912 78.048 -1.078 0.847 -0.230 H4 DWB 33 DWB H5 H5 H 0 1 N N N 26.826 49.569 77.385 -2.215 -3.189 0.641 H5 DWB 34 DWB H6 H6 H 0 1 N N N 27.767 51.096 75.711 0.123 -3.727 1.169 H6 DWB 35 DWB H7 H7 H 0 1 N N N 31.149 52.843 73.240 4.592 -2.866 0.851 H7 DWB 36 DWB H8 H8 H 0 1 N N N 33.513 53.046 72.552 6.470 -1.513 0.022 H8 DWB 37 DWB H9 H9 H 0 1 N N N 37.028 52.363 72.357 8.320 1.051 -1.219 H9 DWB 38 DWB H10 H10 H 0 1 N N N 35.420 52.168 71.580 7.868 0.038 0.173 H10 DWB 39 DWB H11 H11 H 0 1 N N N 35.678 53.465 72.795 7.545 -0.529 -1.483 H11 DWB 40 DWB H12 H12 H 0 1 N N N 34.538 49.927 75.284 3.821 1.781 -0.592 H12 DWB 41 DWB H13 H13 H 0 1 N N N 31.660 47.293 75.852 0.961 1.136 2.294 H13 DWB 42 DWB H14 H14 H 0 1 N N N 32.929 48.002 74.798 2.445 1.966 1.715 H14 DWB 43 DWB H15 H15 H 0 1 N N N 35.258 47.670 78.730 0.082 4.433 -0.947 H15 DWB 44 DWB H16 H16 H 0 1 N N N 34.838 49.271 79.240 0.578 3.526 -2.272 H16 DWB 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 DWB C29 O28 SING N N 1 DWB C2 C3 DOUB Y N 2 DWB C2 C1 SING Y N 3 DWB O28 C1 SING N N 4 DWB C3 C4 SING Y N 5 DWB C1 C6 DOUB Y N 6 DWB C4 O25 SING N N 7 DWB C4 C5 DOUB Y N 8 DWB C6 C5 SING Y N 9 DWB O25 C9 SING N N 10 DWB C5 C7 SING N N 11 DWB C18 C7 SING N N 12 DWB C18 O17 SING N N 13 DWB C9 C10 DOUB Y N 14 DWB C9 C8 SING Y N 15 DWB C10 C11 SING Y N 16 DWB C7 C8 SING N N 17 DWB C7 N15 SING N N 18 DWB C8 C13 DOUB Y N 19 DWB O17 C16 SING N N 20 DWB C11 C12 DOUB Y N 21 DWB N15 C16 DOUB N N 22 DWB F26 C20 SING N N 23 DWB C13 C12 SING Y N 24 DWB C16 N19 SING N N 25 DWB C12 C14 SING N N 26 DWB C20 C14 DOUB Y N 27 DWB C20 C21 SING Y N 28 DWB C14 C24 SING Y N 29 DWB C21 C22 DOUB Y N 30 DWB C24 C23 DOUB Y N 31 DWB C22 C23 SING Y N 32 DWB C23 CL2 SING N N 33 DWB C21 H1 SING N N 34 DWB C22 H2 SING N N 35 DWB C24 H3 SING N N 36 DWB C13 H4 SING N N 37 DWB C11 H5 SING N N 38 DWB C10 H6 SING N N 39 DWB C3 H7 SING N N 40 DWB C2 H8 SING N N 41 DWB C29 H9 SING N N 42 DWB C29 H10 SING N N 43 DWB C29 H11 SING N N 44 DWB C6 H12 SING N N 45 DWB C18 H13 SING N N 46 DWB C18 H14 SING N N 47 DWB N19 H15 SING N N 48 DWB N19 H16 SING N N 49 # 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 DWB SMILES ACDLabs 12.01 "Clc1cc(c(F)cc1)c5ccc4Oc2c(cc(OC)cc2)C3(N=C(OC3)N)c4c5" DWB InChI InChI 1.03 "InChI=1S/C22H16ClFN2O3/c1-27-14-4-7-20-17(10-14)22(11-28-21(25)26-22)16-8-12(2-6-19(16)29-20)15-9-13(23)3-5-18(15)24/h2-10H,11H2,1H3,(H2,25,26)/t22-/m0/s1" DWB InChIKey InChI 1.03 WIRKEQRUHLXVOQ-QFIPXVFZSA-N DWB SMILES_CANONICAL CACTVS 3.370 "COc1ccc2Oc3ccc(cc3[C@@]4(COC(=N4)N)c2c1)c5cc(Cl)ccc5F" DWB SMILES CACTVS 3.370 "COc1ccc2Oc3ccc(cc3[C]4(COC(=N4)N)c2c1)c5cc(Cl)ccc5F" DWB SMILES_CANONICAL "OpenEye OEToolkits" 1.7.6 "COc1ccc2c(c1)[C@]3(COC(=N3)N)c4cc(ccc4O2)c5cc(ccc5F)Cl" DWB SMILES "OpenEye OEToolkits" 1.7.6 "COc1ccc2c(c1)C3(COC(=N3)N)c4cc(ccc4O2)c5cc(ccc5F)Cl" # 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 DWB "SYSTEMATIC NAME" ACDLabs 12.01 "(4S)-2'-(5-chloro-2-fluorophenyl)-7'-methoxyspiro[1,3-oxazole-4,9'-xanthen]-2-amine" DWB "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.7.6 "(4S)-2'-(5-chloranyl-2-fluoranyl-phenyl)-7'-methoxy-spiro[5H-1,3-oxazole-4,9'-xanthene]-2-amine" # loop_ _pdbx_chem_comp_audit.comp_id _pdbx_chem_comp_audit.action_type _pdbx_chem_comp_audit.date _pdbx_chem_comp_audit.processing_site DWB "Create component" 2012-07-03 RCSB DWB "Initial release" 2012-09-07 RCSB #