data_346 # _chem_comp.id 346 _chem_comp.name "(R)-(4-CARBAMIMIDOYL-PHENYLAMINO)-[5-ETHOXY-2-FLUORO-3-[(R)-TETRAHYDRO-FURAN-3-YLOXY]-PHENYL]-ACETIC ACID" _chem_comp.type NON-POLYMER _chem_comp.pdbx_type HETAIN _chem_comp.formula "C21 H24 F N3 O5" _chem_comp.mon_nstd_parent_comp_id ? _chem_comp.pdbx_synonyms "(2R)-({4-[AMINO(IMINO)METHYL]PHENYL}AMINO){5-ETHOXY-2-FLUORO-3-[(3R)-TETRAHYDROFURAN-3-YLOXY]PHENYL}ACETIC ACID" _chem_comp.pdbx_formal_charge 0 _chem_comp.pdbx_initial_date 2005-08-11 _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 417.431 _chem_comp.one_letter_code ? _chem_comp.three_letter_code 346 _chem_comp.pdbx_model_coordinates_details ? _chem_comp.pdbx_model_coordinates_missing_flag N _chem_comp.pdbx_ideal_coordinates_details ? _chem_comp.pdbx_ideal_coordinates_missing_flag N _chem_comp.pdbx_model_coordinates_db_code ? _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 346 F30 F30 F 0 1 N N N 9.108 41.738 30.075 0.981 -2.239 -0.362 F30 346 1 346 C12 C12 C 0 1 Y N N 9.972 42.327 30.928 1.341 -0.938 -0.317 C12 346 2 346 C13 C13 C 0 1 Y N N 10.347 43.614 30.652 2.664 -0.591 -0.068 C13 346 3 346 O25 O25 O 0 1 N N N 9.785 44.171 29.517 3.595 -1.561 0.131 O25 346 4 346 C26 C26 C 0 1 N N R 10.201 45.494 29.198 4.863 -0.907 0.211 C26 346 5 346 C27 C27 C 0 1 N N N 9.332 45.985 28.048 6.004 -1.893 -0.125 C27 346 6 346 C29 C29 C 0 1 N N N 10.136 45.540 26.840 6.853 -1.938 1.165 C29 346 7 346 O28 O28 O 0 1 N N N 11.518 45.557 27.222 5.945 -1.550 2.218 O28 346 8 346 C31 C31 C 0 1 N N N 11.633 45.495 28.653 5.156 -0.470 1.663 C31 346 9 346 C8 C8 C 0 1 Y N N 11.241 44.276 31.494 3.032 0.744 -0.023 C8 346 10 346 C9 C9 C 0 1 Y N N 11.730 43.601 32.621 2.080 1.731 -0.226 C9 346 11 346 O23 O23 O 0 1 N N N 12.629 44.356 33.371 2.439 3.041 -0.182 O23 346 12 346 C24 C24 C 0 1 N N N 13.187 43.660 34.492 3.842 3.076 0.089 C24 346 13 346 C30 C30 C 0 1 N N N 14.192 44.527 35.228 4.313 4.530 0.152 C30 346 14 346 C10 C10 C 0 1 Y N N 11.348 42.277 32.880 0.760 1.382 -0.469 C10 346 15 346 C11 C11 C 0 1 Y N N 10.457 41.622 32.035 0.394 0.049 -0.519 C11 346 16 346 C14 C14 C 0 1 N N R 10.023 40.211 32.302 -1.040 -0.328 -0.789 C14 346 17 346 C15 C15 C 0 1 N N N 9.256 40.129 33.587 -1.223 -0.587 -2.262 C15 346 18 346 O2 O2 O 0 1 N N N 8.113 40.684 33.585 -2.007 0.075 -2.900 O2 346 19 346 O1 O1 O 0 1 N N N 9.728 39.513 34.607 -0.514 -1.554 -2.866 O1 346 20 346 N3 N3 N 0 1 N N N 11.218 39.353 32.373 -1.919 0.768 -0.373 N3 346 21 346 C1 C1 C 0 1 Y N N 11.923 38.925 31.257 -3.230 0.500 0.014 C1 346 22 346 C2 C2 C 0 1 Y N N 11.499 39.168 29.952 -4.064 1.541 0.408 C2 346 23 346 C3 C3 C 0 1 Y N N 12.261 38.698 28.920 -5.360 1.279 0.791 C3 346 24 346 C4 C4 C 0 1 Y N N 13.451 37.989 29.111 -5.838 -0.033 0.784 C4 346 25 346 C7 C7 C 0 1 N N N 14.222 37.522 27.987 -7.229 -0.317 1.195 C7 346 26 346 N1 N1 N 0 1 N N N 13.792 37.660 26.703 -7.699 -1.613 1.187 N1 346 27 346 N2 N2 N 0 1 N N N 15.379 36.870 28.141 -8.012 0.658 1.566 N2 346 28 346 C5 C5 C 0 1 Y N N 13.874 37.741 30.422 -4.998 -1.076 0.387 C5 346 29 346 C6 C6 C 0 1 Y N N 13.118 38.217 31.457 -3.705 -0.808 0.000 C6 346 30 346 H26 H26 H 0 1 N N N 10.128 46.114 30.104 4.891 -0.048 -0.459 H26 346 31 346 H272 2H27 H 0 0 N N N 9.134 47.067 28.074 6.597 -1.520 -0.960 H272 346 32 346 H271 1H27 H 0 0 N N N 8.328 45.535 28.066 5.601 -2.880 -0.352 H271 346 33 346 H292 2H29 H 0 0 N N N 9.959 46.210 25.986 7.681 -1.233 1.098 H292 346 34 346 H291 1H29 H 0 0 N N N 9.837 44.526 26.537 7.225 -2.948 1.338 H291 346 35 346 H312 2H31 H 0 0 N N N 12.182 44.596 28.971 4.226 -0.353 2.221 H312 346 36 346 H311 1H31 H 0 0 N N N 12.191 46.363 29.034 5.725 0.460 1.674 H311 346 37 346 H8 H8 H 0 1 N N N 11.550 45.289 31.282 4.059 1.015 0.171 H8 346 38 346 H241 1H24 H 0 0 N N N 13.703 42.761 34.125 4.378 2.555 -0.704 H241 346 39 346 H242 2H24 H 0 0 N N N 12.376 43.389 35.183 4.040 2.588 1.043 H242 346 40 346 H303 3H30 H 0 0 N N N 14.542 43.999 36.127 3.777 5.052 0.945 H303 346 41 346 H302 2H30 H 0 0 N N N 13.714 45.474 35.521 4.115 5.018 -0.802 H302 346 42 346 H301 1H30 H 0 0 N N N 15.048 44.737 34.570 5.383 4.557 0.359 H301 346 43 346 H10 H10 H 0 1 N N N 11.748 41.762 33.741 0.018 2.151 -0.626 H10 346 44 346 H14 H14 H 0 1 N N N 9.365 39.872 31.489 -1.291 -1.228 -0.228 H14 346 45 346 H1 H1 H 0 1 N N N 9.099 39.548 35.318 -0.631 -1.720 -3.812 H1 346 46 346 H33 H33 H 0 1 N N N 11.879 39.874 32.913 -1.589 1.680 -0.368 H33 346 47 346 H2 H2 H 0 1 N N N 10.588 39.716 29.761 -3.694 2.556 0.414 H2 346 48 346 H3 H3 H 0 1 N N N 11.929 38.883 27.909 -6.007 2.088 1.098 H3 346 49 346 H12 H12 H 0 1 N N N 12.930 38.083 26.423 -8.612 -1.799 1.457 H12 346 50 346 H11 H11 H 0 1 N N N 14.474 37.271 26.084 -7.117 -2.338 0.912 H11 346 51 346 H21 H21 H 0 1 N N N 15.593 36.806 29.116 -8.924 0.471 1.835 H21 346 52 346 H5 H5 H 0 1 N N N 14.780 37.185 30.612 -5.365 -2.092 0.381 H5 346 53 346 H6 H6 H 0 1 N N N 13.454 38.041 32.468 -3.055 -1.614 -0.307 H6 346 54 # # 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 346 F30 C12 SING N N 1 346 C12 C13 DOUB Y N 2 346 C12 C11 SING Y N 3 346 C13 O25 SING N N 4 346 C13 C8 SING Y N 5 346 O25 C26 SING N N 6 346 C26 C27 SING N N 7 346 C26 C31 SING N N 8 346 C26 H26 SING N N 9 346 C27 C29 SING N N 10 346 C27 H272 SING N N 11 346 C27 H271 SING N N 12 346 C29 O28 SING N N 13 346 C29 H292 SING N N 14 346 C29 H291 SING N N 15 346 O28 C31 SING N N 16 346 C31 H312 SING N N 17 346 C31 H311 SING N N 18 346 C8 C9 DOUB Y N 19 346 C8 H8 SING N N 20 346 C9 O23 SING N N 21 346 C9 C10 SING Y N 22 346 O23 C24 SING N N 23 346 C24 C30 SING N N 24 346 C24 H241 SING N N 25 346 C24 H242 SING N N 26 346 C30 H303 SING N N 27 346 C30 H302 SING N N 28 346 C30 H301 SING N N 29 346 C10 C11 DOUB Y N 30 346 C10 H10 SING N N 31 346 C11 C14 SING N N 32 346 C14 C15 SING N N 33 346 C14 N3 SING N N 34 346 C14 H14 SING N N 35 346 C15 O2 DOUB N N 36 346 C15 O1 SING N N 37 346 O1 H1 SING N N 38 346 N3 C1 SING N N 39 346 N3 H33 SING N N 40 346 C1 C2 DOUB Y N 41 346 C1 C6 SING Y N 42 346 C2 C3 SING Y N 43 346 C2 H2 SING N N 44 346 C3 C4 DOUB Y N 45 346 C3 H3 SING N N 46 346 C4 C7 SING N N 47 346 C4 C5 SING Y N 48 346 C7 N1 SING N N 49 346 C7 N2 DOUB N E 50 346 N1 H12 SING N N 51 346 N1 H11 SING N N 52 346 N2 H21 SING N N 53 346 C5 C6 DOUB Y N 54 346 C5 H5 SING N N 55 346 C6 H6 SING N N 56 # # 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 346 SMILES ACDLabs 10.04 "O=C(O)C(c2c(F)c(OC1CCOC1)cc(OCC)c2)Nc3ccc(C(=[N@H])N)cc3" 346 SMILES_CANONICAL CACTVS 3.341 "CCOc1cc(O[C@@H]2CCOC2)c(F)c(c1)[C@@H](Nc3ccc(cc3)C(N)=N)C(O)=O" 346 SMILES CACTVS 3.341 "CCOc1cc(O[CH]2CCOC2)c(F)c(c1)[CH](Nc3ccc(cc3)C(N)=N)C(O)=O" 346 SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 "[H]/N=C(\c1ccc(cc1)N[C@H](c2cc(cc(c2F)O[C@@H]3CCOC3)OCC)C(=O)O)/N" 346 SMILES "OpenEye OEToolkits" 1.5.0 "[H]N=C(c1ccc(cc1)NC(c2cc(cc(c2F)OC3CCOC3)OCC)C(=O)O)N" 346 InChI InChI 1.03 "InChI=1S/C21H24FN3O5/c1-2-29-15-9-16(18(22)17(10-15)30-14-7-8-28-11-14)19(21(26)27)25-13-5-3-12(4-6-13)20(23)24/h3-6,9-10,14,19,25H,2,7-8,11H2,1H3,(H3,23,24)(H,26,27)/t14-,19-/m1/s1" 346 InChIKey InChI 1.03 PGYOHIAQCFZQDK-AUUYWEPGSA-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 346 "SYSTEMATIC NAME" ACDLabs 10.04 "(2R)-[(4-carbamimidoylphenyl)amino]{5-ethoxy-2-fluoro-3-[(3R)-tetrahydrofuran-3-yloxy]phenyl}ethanoic acid" 346 "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "(2R)-2-[(4-carbamimidoylphenyl)amino]-2-[5-ethoxy-2-fluoro-3-[(3R)-oxolan-3-yl]oxy-phenyl]ethanoic 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 346 "Create component" 2005-08-11 EBI 346 "Modify descriptor" 2011-06-04 RCSB 346 "Modify synonyms" 2020-06-05 PDBE # _pdbx_chem_comp_synonyms.ordinal 1 _pdbx_chem_comp_synonyms.comp_id 346 _pdbx_chem_comp_synonyms.name "(2R)-({4-[AMINO(IMINO)METHYL]PHENYL}AMINO){5-ETHOXY-2-FLUORO-3-[(3R)-TETRAHYDROFURAN-3-YLOXY]PHENYL}ACETIC ACID" _pdbx_chem_comp_synonyms.provenance ? _pdbx_chem_comp_synonyms.type ? ##