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                    2008-10-14 
_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 InChI            InChI                1.02b InChI=1/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/f/h23,26H,24H2/b23-20+ 
346 InChIKey         InChI                1.02b PGYOHIAQCFZQDK-LQCILASMDB                                                                                                                                                                                   
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                                                                                                                                                       
# 
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"    
# 
