data_688
# 
_chem_comp.id                                    688 
_chem_comp.name                                  "2-[AMINO(IMINO)METHYL]-2-HYDROXYPHENOXY]-6-[3-(4,5-DIHYDRO-1H-IMIDAZOL-2-YL)PHENOXY]PYRIDINE-4-CARBOXYLIC ACID" 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C22 H17 N5 O5" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         ZK-806688 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     1999-07-08 
_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                        431.401 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     688 
_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        1QBN 
_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 
688 C1   C1   C 0 1 Y N N 8.436  25.098 19.790 -1.696 -1.016 -1.890 C1   688 1  
688 C2   C2   C 0 1 Y N N 9.262  26.194 19.385 -2.503 -0.177 -1.117 C2   688 2  
688 C3   C3   C 0 1 Y N N 10.650 25.933 19.285 -1.912 0.516  -0.057 C3   688 3  
688 C4   C4   C 0 1 Y N N 11.078 24.573 19.286 -0.557 0.348  0.186  C4   688 4  
688 N5   N5   N 0 1 Y N N 10.264 23.549 19.569 0.171  -0.460 -0.565 N5   688 5  
688 C6   C6   C 0 1 Y N N 8.936  23.795 19.704 -0.348 -1.129 -1.580 C6   688 6  
688 O1   O1   O 0 1 N N N 12.338 24.264 18.891 0.026  1.016  1.212  O1   688 7  
688 O2   O2   O 0 1 N N N 8.179  22.717 20.060 0.444  -1.941 -2.324 O2   688 8  
688 C7   C7   C 0 1 N N N 8.786  27.479 19.486 -3.946 -0.027 -1.414 C7   688 9  
688 O3   O3   O 0 1 N N N 9.517  28.453 19.413 -4.442 -0.637 -2.339 O3   688 10 
688 O4   O4   O 0 1 N N N 7.478  27.686 19.686 -4.707 0.785  -0.657 O4   688 11 
688 C11  C11  C 0 1 Y N N 8.777  21.557 20.501 1.045  -1.155 -3.257 C11  688 12 
688 C12  C12  C 0 1 Y N N 8.549  20.491 19.610 0.695  0.177  -3.368 C12  688 13 
688 C13  C13  C 0 1 Y N N 9.019  19.208 19.872 1.311  0.979  -4.330 C13  688 14 
688 C14  C14  C 0 1 Y N N 9.772  18.971 21.062 2.284  0.435  -5.169 C14  688 15 
688 C15  C15  C 0 1 Y N N 10.026 20.043 21.951 2.633  -0.893 -5.051 C15  688 16 
688 C16  C16  C 0 1 Y N N 9.514  21.337 21.666 2.018  -1.692 -4.098 C16  688 17 
688 C17  C17  C 0 1 N N N 8.772  18.159 18.940 0.936  2.404  -4.456 C17  688 18 
688 N11  N11  N 0 1 N N N 8.023  18.243 17.867 0.110  2.939  -3.601 N11  688 19 
688 N12  N12  N 0 1 N N N 9.308  16.950 19.089 1.460  3.167  -5.478 N12  688 20 
688 O11  O11  O 0 1 N N N 9.817  22.335 22.553 2.364  -3.001 -3.985 O11  688 21 
688 C21  C21  C 0 1 Y N N 13.442 25.043 18.822 -0.010 0.189  2.291  C21  688 22 
688 C22  C22  C 0 1 Y N N 13.578 26.061 19.788 -0.476 -1.111 2.152  C22  688 23 
688 C23  C23  C 0 1 Y N N 14.723 26.887 19.769 -0.515 -1.956 3.246  C23  688 24 
688 C24  C24  C 0 1 Y N N 15.663 26.687 18.747 -0.092 -1.512 4.482  C24  688 25 
688 C25  C25  C 0 1 Y N N 15.520 25.699 17.762 0.377  -0.206 4.630  C25  688 26 
688 C26  C26  C 0 1 Y N N 14.378 24.860 17.776 0.422  0.643  3.525  C26  688 27 
688 C27  C27  C 0 1 Y N N 16.435 25.449 16.716 0.832  0.272  5.954  C27  688 28 
688 N21  N21  N 0 1 Y N N 17.525 26.145 16.394 0.943  -0.485 7.083  N21  688 29 
688 N22  N22  N 0 1 Y N N 16.518 24.226 16.137 1.203  1.500  6.242  N22  688 30 
688 C28  C28  C 0 1 Y N N 17.670 24.124 15.319 1.545  1.565  7.534  C28  688 31 
688 C29  C29  C 0 1 Y N N 18.244 25.555 15.333 1.395  0.340  8.076  C29  688 32 
688 H1   H1   H 0 1 N N N 7.412  25.257 20.169 -2.115 -1.569 -2.718 H1   688 33 
688 H3   H3   H 0 1 N N N 11.373 26.761 19.208 -2.503 1.174  0.562  H3   688 34 
688 HO4  HO4  H 0 1 N N N 7.148  28.574 19.755 -5.650 0.883  -0.851 HO4  688 35 
688 H12  H12  H 0 1 N N N 7.985  20.666 18.678 -0.057 0.595  -2.716 H12  688 36 
688 H14  H14  H 0 1 N N N 10.156 17.963 21.293 2.764  1.055  -5.912 H14  688 37 
688 H15  H15  H 0 1 N N N 10.621 19.870 22.863 3.386  -1.312 -5.701 H15  688 38 
688 HN11 HN11 H 0 0 N N N 7.788  18.780 18.701 -0.197 2.425  -2.839 HN11 688 39 
688 H121 1H12 H 0 0 N N N 9.131  16.199 18.421 1.158  4.080  -5.605 H121 688 40 
688 H122 2H12 H 0 0 N N N 9.057  16.609 20.017 2.133  2.792  -6.067 H122 688 41 
688 HO11 HO11 H 0 0 N N N 10.318 22.185 23.345 3.091  -3.044 -3.349 HO11 688 42 
688 H22  H22  H 0 1 N N N 12.795 26.209 20.551 -0.809 -1.463 1.187  H22  688 43 
688 H23  H23  H 0 1 N N N 14.879 27.667 20.532 -0.879 -2.966 3.132  H23  688 44 
688 H24  H24  H 0 1 N N N 16.554 27.335 18.716 -0.124 -2.174 5.334  H24  688 45 
688 H26  H26  H 0 1 N N N 14.223 24.091 17.000 0.784  1.654  3.634  H26  688 46 
688 HN21 HN21 H 0 0 N N N 17.772 27.002 16.887 0.741  -1.430 7.165  HN21 688 47 
688 H28  H28  H 0 1 N N N 18.017 23.203 14.819 1.888  2.448  8.053  H28  688 48 
688 H29  H29  H 0 1 N N N 19.009 26.052 14.713 1.593  0.063  9.101  H29  688 49 
# 
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 
688 C1  C2   DOUB Y N 1  
688 C1  C6   SING Y N 2  
688 C1  H1   SING N N 3  
688 C2  C3   SING Y N 4  
688 C2  C7   SING N N 5  
688 C3  C4   DOUB Y N 6  
688 C3  H3   SING N N 7  
688 C4  N5   SING Y N 8  
688 C4  O1   SING N N 9  
688 N5  C6   DOUB Y N 10 
688 C6  O2   SING N N 11 
688 O1  C21  SING N N 12 
688 O2  C11  SING N N 13 
688 C7  O3   DOUB N N 14 
688 C7  O4   SING N N 15 
688 O4  HO4  SING N N 16 
688 C11 C12  DOUB Y N 17 
688 C11 C16  SING Y N 18 
688 C12 C13  SING Y N 19 
688 C12 H12  SING N N 20 
688 C13 C14  DOUB Y N 21 
688 C13 C17  SING N N 22 
688 C14 C15  SING Y N 23 
688 C14 H14  SING N N 24 
688 C15 C16  DOUB Y N 25 
688 C15 H15  SING N N 26 
688 C16 O11  SING N N 27 
688 C17 N11  DOUB N N 28 
688 C17 N12  SING N N 29 
688 N11 HN11 SING N N 30 
688 N12 H121 SING N N 31 
688 N12 H122 SING N N 32 
688 O11 HO11 SING N N 33 
688 C21 C22  DOUB Y N 34 
688 C21 C26  SING Y N 35 
688 C22 C23  SING Y N 36 
688 C22 H22  SING N N 37 
688 C23 C24  DOUB Y N 38 
688 C23 H23  SING N N 39 
688 C24 C25  SING Y N 40 
688 C24 H24  SING N N 41 
688 C25 C26  DOUB Y N 42 
688 C25 C27  SING N N 43 
688 C26 H26  SING N N 44 
688 C27 N21  SING Y N 45 
688 C27 N22  DOUB Y N 46 
688 N21 C29  SING Y N 47 
688 N21 HN21 SING N N 48 
688 N22 C28  SING Y N 49 
688 C28 C29  DOUB Y N 50 
688 C28 H28  SING N N 51 
688 C29 H29  SING N N 52 
# 
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 
688 SMILES           ACDLabs              10.04 O=C(O)c2cc(nc(Oc1cc(C(=[N@H])N)ccc1O)c2)Oc3cccc(c3)c4nccn4                                                                                                                              
688 InChI            InChI                1.02b InChI=1/C22H17N5O5/c23-20(24)12-4-5-16(28)17(9-12)32-19-11-14(22(29)30)10-18(27-19)31-15-3-1-2-13(8-15)21-25-6-7-26-21/h1-11,28H,(H3,23,24)(H,25,26)(H,29,30)/f/h23,25,29H,24H2/b23-20+ 
688 InChIKey         InChI                1.02b ILFWHJBPGCBXAY-JPYSGQCIDO                                                                                                                                                               
688 SMILES_CANONICAL CACTVS               3.341 NC(=N)c1ccc(O)c(Oc2cc(cc(Oc3cccc(c3)c4[nH]ccn4)n2)C(O)=O)c1                                                                                                                             
688 SMILES           CACTVS               3.341 NC(=N)c1ccc(O)c(Oc2cc(cc(Oc3cccc(c3)c4[nH]ccn4)n2)C(O)=O)c1                                                                                                                             
688 SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 c1cc(cc(c1)Oc2cc(cc(n2)Oc3cc(ccc3O)C(=N)N)C(=O)O)c4[nH]ccn4                                                                                                                             
688 SMILES           "OpenEye OEToolkits" 1.5.0 c1cc(cc(c1)Oc2cc(cc(n2)Oc3cc(ccc3O)C(=N)N)C(=O)O)c4[nH]ccn4                                                                                                                             
# 
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 
688 "SYSTEMATIC NAME" ACDLabs              10.04 "2-(5-carbamimidoyl-2-hydroxyphenoxy)-6-[3-(1H-imidazol-2-yl)phenoxy]pyridine-4-carboxylic acid"  
688 "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "2-(5-carbamimidoyl-2-hydroxy-phenoxy)-6-[3-(1H-imidazol-2-yl)phenoxy]pyridine-4-carboxylic acid" 
# 
