data_1FR # _chem_comp.id 1FR _chem_comp.name "3-[3-chloro-5-(5-{[(1S)-1-phenylethyl]amino}isoxazolo[5,4-c]pyridin-3-yl)phenyl]propan-1-ol" _chem_comp.type NON-POLYMER _chem_comp.pdbx_type HETAIN _chem_comp.formula "C23 H22 Cl N3 O2" _chem_comp.mon_nstd_parent_comp_id ? _chem_comp.pdbx_synonyms "3-{3-Chloro-5-[5-(1-phenyl-ethylamino)-isoxazolo[5,4-c]pyridin-3-yl]-phenyl}-propan-1-ol" _chem_comp.pdbx_formal_charge 0 _chem_comp.pdbx_initial_date 2008-06-16 _chem_comp.pdbx_modified_date 2020-06-17 _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 407.893 _chem_comp.one_letter_code ? _chem_comp.three_letter_code 1FR _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 3DB8 _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 1FR C28 C28 C 0 1 Y N N 118.734 57.066 42.634 -4.669 -2.141 -1.146 C28 1FR 1 1FR C27 C27 C 0 1 Y N N 119.073 58.336 43.106 -5.812 -2.722 -1.662 C27 1FR 2 1FR C26 C26 C 0 1 Y N N 119.818 58.483 44.276 -7.053 -2.199 -1.351 C26 1FR 3 1FR C24 C24 C 0 1 Y N N 119.876 56.090 44.514 -6.008 -0.515 -0.008 C24 1FR 4 1FR C23 C23 C 0 1 Y N N 119.134 55.926 43.338 -4.767 -1.038 -0.319 C23 1FR 5 1FR C22 C22 C 0 1 N N S 118.800 54.541 42.886 -3.520 -0.405 0.244 C22 1FR 6 1FR C17 C17 C 0 1 N N N 117.701 58.754 47.149 5.092 -1.025 -1.365 C17 1FR 7 1FR C15 C15 C 0 1 Y N N 115.790 57.722 45.832 3.176 0.389 -0.604 C15 1FR 8 1FR C12 C12 C 0 1 Y N N 114.206 57.608 48.115 2.100 -1.723 0.836 C12 1FR 9 1FR C13 C13 C 0 1 Y N N 115.499 58.124 48.188 3.275 -1.890 0.124 C13 1FR 10 1FR C14 C14 C 0 1 Y N N 116.298 58.187 47.047 3.811 -0.835 -0.593 C14 1FR 11 1FR C11 C11 C 0 1 Y N N 113.697 57.151 46.902 1.455 -0.501 0.832 C11 1FR 12 1FR C10 C10 C 0 1 Y N N 114.493 57.201 45.758 1.991 0.564 0.110 C10 1FR 13 1FR C8 C8 C 0 1 Y N N 113.950 56.711 44.457 1.304 1.878 0.102 C8 1FR 14 1FR C4 C4 C 0 1 Y N N 114.716 55.971 43.404 -0.148 2.104 0.129 C4 1FR 15 1FR C5 C5 C 0 1 Y N N 113.830 55.725 42.392 -0.336 3.497 0.109 C5 1FR 16 1FR C6 C6 C 0 1 Y N N 114.210 55.047 41.238 -1.630 3.997 0.128 C6 1FR 17 1FR C3 C3 C 0 1 Y N N 116.027 55.540 43.305 -1.270 1.276 0.167 C3 1FR 18 1FR C2 C2 C 0 1 Y N N 116.401 54.860 42.139 -2.526 1.862 0.184 C2 1FR 19 1FR CL CL CL 0 0 N N N 113.197 57.535 49.595 1.434 -3.052 1.733 CL 1FR 20 1FR C18 C18 C 0 1 N N N 117.789 60.128 46.483 6.283 -0.685 -0.467 C18 1FR 21 1FR C19 C19 C 0 1 N N N 117.325 61.249 47.405 7.583 -0.877 -1.251 C19 1FR 22 1FR O20 O20 O 0 1 N N N 116.184 61.904 46.831 8.696 -0.560 -0.412 O20 1FR 23 1FR O21 O21 O 0 1 Y N N 112.567 56.249 42.724 0.887 4.062 0.073 O21 1FR 24 1FR N9 N9 N 0 1 Y N N 112.662 56.865 44.023 1.876 3.052 0.075 N9 1FR 25 1FR N1 N1 N 0 1 Y N N 115.489 54.632 41.147 -2.664 3.181 0.163 N1 1FR 26 1FR N7 N7 N 0 1 N N N 117.675 54.416 41.954 -3.661 1.054 0.222 N7 1FR 27 1FR C29 C29 C 0 1 N N N 120.012 53.916 42.200 -3.316 -0.876 1.686 C29 1FR 28 1FR C25 C25 C 0 1 Y N N 120.221 57.357 44.988 -7.152 -1.096 -0.524 C25 1FR 29 1FR H28 H28 H 0 1 N N N 118.162 56.964 41.724 -3.699 -2.552 -1.385 H28 1FR 30 1FR H27 H27 H 0 1 N N N 118.755 59.212 42.560 -5.735 -3.583 -2.309 H27 1FR 31 1FR H26 H26 H 0 1 N N N 120.082 59.469 44.629 -7.946 -2.653 -1.755 H26 1FR 32 1FR H24 H24 H 0 1 N N N 120.189 55.217 45.067 -6.085 0.346 0.639 H24 1FR 33 1FR H22 H22 H 0 1 N N N 118.504 54.029 43.813 -2.661 -0.696 -0.359 H22 1FR 34 1FR H17 H17 H 0 1 N N N 117.969 58.854 48.211 5.168 -2.061 -1.693 H17 1FR 35 1FR H17A H17A H 0 0 N N N 118.393 58.071 46.635 5.093 -0.367 -2.234 H17A 1FR 36 1FR H15 H15 H 0 1 N N N 116.402 57.765 44.943 3.597 1.213 -1.161 H15 1FR 37 1FR H13 H13 H 0 1 N N N 115.884 58.477 49.133 3.776 -2.846 0.130 H13 1FR 38 1FR H11 H11 H 0 1 N N N 112.692 56.760 46.848 0.538 -0.372 1.387 H11 1FR 39 1FR H6 H6 H 0 1 N N N 113.504 54.860 40.442 -1.792 5.065 0.113 H6 1FR 40 1FR H3 H3 H 0 1 N N N 116.737 55.721 44.099 -1.162 0.202 0.183 H3 1FR 41 1FR H18 H18 H 0 1 N N N 118.837 60.315 46.205 6.207 0.352 -0.139 H18 1FR 42 1FR H18A H18A H 0 0 N N N 117.129 60.120 45.603 6.282 -1.343 0.402 H18A 1FR 43 1FR H19 H19 H 0 1 N N N 117.051 60.828 48.384 7.660 -1.914 -1.579 H19 1FR 44 1FR H19A H19A H 0 0 N N N 118.139 61.978 47.532 7.584 -0.220 -2.120 H19A 1FR 45 1FR HO20 HO20 H 0 0 N N N 115.529 62.049 47.504 9.555 -0.660 -0.845 HO20 1FR 46 1FR HN7 HN7 H 0 1 N N N 117.984 54.902 41.137 -4.543 1.456 0.234 HN7 1FR 47 1FR H29 H29 H 0 1 N N N 119.793 53.766 41.133 -3.212 -1.960 1.702 H29 1FR 48 1FR H29A H29A H 0 0 N N N 120.878 54.585 42.305 -2.414 -0.418 2.093 H29A 1FR 49 1FR H29B H29B H 0 0 N N N 120.238 52.946 42.668 -4.176 -0.584 2.289 H29B 1FR 50 1FR H25 H25 H 0 1 N N N 120.794 57.462 45.897 -8.122 -0.688 -0.282 H25 1FR 51 # # 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 1FR C28 C27 DOUB Y N 1 1FR C28 C23 SING Y N 2 1FR C27 C26 SING Y N 3 1FR C26 C25 DOUB Y N 4 1FR C24 C23 DOUB Y N 5 1FR C24 C25 SING Y N 6 1FR C23 C22 SING N N 7 1FR C22 N7 SING N N 8 1FR C22 C29 SING N N 9 1FR C17 C14 SING N N 10 1FR C17 C18 SING N N 11 1FR C15 C14 DOUB Y N 12 1FR C15 C10 SING Y N 13 1FR C12 C13 DOUB Y N 14 1FR C12 C11 SING Y N 15 1FR C12 CL SING N N 16 1FR C13 C14 SING Y N 17 1FR C11 C10 DOUB Y N 18 1FR C10 C8 SING Y N 19 1FR C8 C4 SING Y N 20 1FR C8 N9 DOUB Y N 21 1FR C4 C5 DOUB Y N 22 1FR C4 C3 SING Y N 23 1FR C5 C6 SING Y N 24 1FR C5 O21 SING Y N 25 1FR C6 N1 DOUB Y N 26 1FR C3 C2 DOUB Y N 27 1FR C2 N1 SING Y N 28 1FR C2 N7 SING N N 29 1FR C18 C19 SING N N 30 1FR C19 O20 SING N N 31 1FR O21 N9 SING Y N 32 1FR C28 H28 SING N N 33 1FR C27 H27 SING N N 34 1FR C26 H26 SING N N 35 1FR C24 H24 SING N N 36 1FR C22 H22 SING N N 37 1FR C17 H17 SING N N 38 1FR C17 H17A SING N N 39 1FR C15 H15 SING N N 40 1FR C13 H13 SING N N 41 1FR C11 H11 SING N N 42 1FR C6 H6 SING N N 43 1FR C3 H3 SING N N 44 1FR C18 H18 SING N N 45 1FR C18 H18A SING N N 46 1FR C19 H19 SING N N 47 1FR C19 H19A SING N N 48 1FR O20 HO20 SING N N 49 1FR N7 HN7 SING N N 50 1FR C29 H29 SING N N 51 1FR C29 H29A SING N N 52 1FR C29 H29B SING N N 53 1FR C25 H25 SING N N 54 # # 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 1FR SMILES ACDLabs 10.04 "Clc4cc(cc(c2noc1cnc(cc12)NC(c3ccccc3)C)c4)CCCO" 1FR SMILES_CANONICAL CACTVS 3.341 "C[C@H](Nc1cc2c(onc2c3cc(Cl)cc(CCCO)c3)cn1)c4ccccc4" 1FR SMILES CACTVS 3.341 "C[CH](Nc1cc2c(onc2c3cc(Cl)cc(CCCO)c3)cn1)c4ccccc4" 1FR SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 "C[C@@H](c1ccccc1)Nc2cc3c(cn2)onc3c4cc(cc(c4)Cl)CCCO" 1FR SMILES "OpenEye OEToolkits" 1.5.0 "CC(c1ccccc1)Nc2cc3c(cn2)onc3c4cc(cc(c4)Cl)CCCO" 1FR InChI InChI 1.03 "InChI=1S/C23H22ClN3O2/c1-15(17-7-3-2-4-8-17)26-22-13-20-21(14-25-22)29-27-23(20)18-10-16(6-5-9-28)11-19(24)12-18/h2-4,7-8,10-15,28H,5-6,9H2,1H3,(H,25,26)/t15-/m0/s1" 1FR InChIKey InChI 1.03 MMGKIHLBFPJYJL-HNNXBMFYSA-N # # 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 1FR "SYSTEMATIC NAME" ACDLabs 10.04 "3-[3-chloro-5-(5-{[(1S)-1-phenylethyl]amino}isoxazolo[5,4-c]pyridin-3-yl)phenyl]propan-1-ol" 1FR "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "3-[3-chloro-5-[5-[[(1S)-1-phenylethyl]amino]-[1,2]oxazolo[4,5-d]pyridin-3-yl]phenyl]propan-1-ol" # # loop_ _pdbx_chem_comp_audit.comp_id _pdbx_chem_comp_audit.action_type _pdbx_chem_comp_audit.date _pdbx_chem_comp_audit.processing_site 1FR "Create component" 2008-06-16 RCSB 1FR "Modify aromatic_flag" 2011-06-04 RCSB 1FR "Modify descriptor" 2011-06-04 RCSB 1FR "Modify synonyms" 2020-06-05 PDBE # _pdbx_chem_comp_synonyms.ordinal 1 _pdbx_chem_comp_synonyms.comp_id 1FR _pdbx_chem_comp_synonyms.name "3-{3-Chloro-5-[5-(1-phenyl-ethylamino)-isoxazolo[5,4-c]pyridin-3-yl]-phenyl}-propan-1-ol" _pdbx_chem_comp_synonyms.provenance ? _pdbx_chem_comp_synonyms.type ? ##