data_TOP
# 
_chem_comp.id                                    TOP 
_chem_comp.name                                  TRIMETHOPRIM 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C14 H18 N4 O3" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         ? 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     1999-07-08 
_chem_comp.pdbx_modified_date                    2011-06-04 
_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                        290.318 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     TOP 
_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        1DYR 
_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 
TOP C1   C1   C 0 1 Y N N 16.577 4.023 -5.254  -1.424 -0.480 2.568  C1   TOP 1  
TOP N2   N2   N 0 1 Y N N 15.914 2.958 -4.788  -1.498 0.402  3.552  N2   TOP 2  
TOP C3   C3   C 0 1 Y N N 16.103 2.647 -3.538  -0.401 0.909  4.097  C3   TOP 3  
TOP N4   N4   N 0 1 N N N 15.422 1.596 -2.999  -0.520 1.829  5.123  N4   TOP 4  
TOP N5   N5   N 0 1 Y N N 16.873 3.282 -2.623  0.806  0.557  3.683  N5   TOP 5  
TOP C6   C6   C 0 1 Y N N 17.514 4.358 -3.090  0.954  -0.328 2.702  C6   TOP 6  
TOP N7   N7   N 0 1 N N N 18.277 5.090 -2.249  2.218  -0.694 2.271  N7   TOP 7  
TOP C8   C8   C 0 1 Y N N 17.353 4.769 -4.403  -0.183 -0.875 2.105  C8   TOP 8  
TOP C9   C9   C 0 1 N N N 18.101 6.012 -4.909  -0.061 -1.877 0.987  C9   TOP 9  
TOP C10  C10  C 0 1 Y N N 17.980 6.391 -6.387  -0.038 -1.155 -0.334 C10  TOP 10 
TOP C11  C11  C 0 1 Y N N 19.128 6.284 -7.163  1.166  -0.748 -0.877 C11  TOP 11 
TOP C12  C12  C 0 1 Y N N 19.110 6.637 -8.517  1.192  -0.083 -2.093 C12  TOP 12 
TOP O13  O13  O 0 1 N N N 20.213 6.499 -9.320  2.377  0.316  -2.626 O13  TOP 13 
TOP C14  C14  C 0 1 N N N 21.464 6.362 -8.690  3.398  -0.088 -1.711 C14  TOP 14 
TOP C15  C15  C 0 1 Y N N 17.905 7.114 -9.067  0.003  0.179  -2.764 C15  TOP 15 
TOP O16  O16  O 0 1 N N N 17.827 7.494 -10.423 0.024  0.833  -3.958 O16  TOP 16 
TOP C17  C17  C 0 1 N N N 16.651 6.953 -10.933 -0.085 2.227  -3.667 C17  TOP 17 
TOP C18  C18  C 0 1 Y N N 16.760 7.254 -8.290  -1.204 -0.235 -2.218 C18  TOP 18 
TOP O19  O19  O 0 1 N N N 15.630 7.745 -8.949  -2.370 0.014  -2.873 O19  TOP 19 
TOP C20  C20  C 0 1 N N N 14.648 8.167 -7.997  -3.420 -0.521 -2.067 C20  TOP 20 
TOP C21  C21  C 0 1 Y N N 16.772 6.898 -6.932  -1.221 -0.900 -1.001 C21  TOP 21 
TOP H1   H1   H 0 1 N N N 16.485 4.281 -6.322  -2.324 -0.887 2.131  H1   TOP 22 
TOP HN41 1HN4 H 0 0 N N N 15.570 1.352 -2.019  -1.399 2.095  5.436  HN41 TOP 23 
TOP HN42 2HN4 H 0 0 N N N 15.594 0.768 -3.570  0.274  2.208  5.530  HN42 TOP 24 
TOP HN71 1HN7 H 0 0 N N N 18.766 5.911 -2.605  3.004  -0.304 2.685  HN71 TOP 25 
TOP HN72 2HN7 H 0 0 N N N 18.956 4.473 -1.803  2.318  -1.341 1.554  HN72 TOP 26 
TOP H91  1H9  H 0 1 N N N 17.806 6.888 -4.286  -0.912 -2.558 1.015  H91  TOP 27 
TOP H92  2H9  H 0 1 N N N 19.180 5.914 -4.648  0.861  -2.445 1.107  H92  TOP 28 
TOP H11  H11  H 0 1 N N N 20.059 5.916 -6.701  2.089  -0.949 -0.353 H11  TOP 29 
TOP H141 1H14 H 0 0 N N N 22.360 6.249 -9.342  4.372  0.212  -2.098 H141 TOP 30 
TOP H142 2H14 H 0 0 N N N 21.620 7.217 -7.992  3.229  0.386  -0.745 H142 TOP 31 
TOP H143 3H14 H 0 0 N N N 21.423 5.510 -7.971  3.372  -1.171 -1.594 H143 TOP 32 
TOP H171 1H17 H 0 0 N N N 16.589 7.253 -12.005 -0.073 2.795  -4.598 H171 TOP 33 
TOP H172 2H17 H 0 0 N N N 16.575 5.850 -10.782 -1.020 2.416  -3.139 H172 TOP 34 
TOP H173 3H17 H 0 0 N N N 15.747 7.239 -10.346 0.752  2.536  -3.043 H173 TOP 35 
TOP H201 1H20 H 0 0 N N N 13.746 8.558 -8.522  -4.379 -0.343 -2.554 H201 TOP 36 
TOP H202 2H20 H 0 0 N N N 14.390 7.356 -7.276  -3.271 -1.593 -1.940 H202 TOP 37 
TOP H203 3H20 H 0 0 N N N 15.061 8.906 -7.271  -3.413 -0.035 -1.091 H203 TOP 38 
TOP H21  H21  H 0 1 N N N 15.864 7.012 -6.315  -2.161 -1.220 -0.575 H21  TOP 39 
# 
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 
TOP C1  N2   DOUB Y N 1  
TOP C1  C8   SING Y N 2  
TOP C1  H1   SING N N 3  
TOP N2  C3   SING Y N 4  
TOP C3  N4   SING N N 5  
TOP C3  N5   DOUB Y N 6  
TOP N4  HN41 SING N N 7  
TOP N4  HN42 SING N N 8  
TOP N5  C6   SING Y N 9  
TOP C6  N7   SING N N 10 
TOP C6  C8   DOUB Y N 11 
TOP N7  HN71 SING N N 12 
TOP N7  HN72 SING N N 13 
TOP C8  C9   SING N N 14 
TOP C9  C10  SING N N 15 
TOP C9  H91  SING N N 16 
TOP C9  H92  SING N N 17 
TOP C10 C11  DOUB Y N 18 
TOP C10 C21  SING Y N 19 
TOP C11 C12  SING Y N 20 
TOP C11 H11  SING N N 21 
TOP C12 O13  SING N N 22 
TOP C12 C15  DOUB Y N 23 
TOP O13 C14  SING N N 24 
TOP C14 H141 SING N N 25 
TOP C14 H142 SING N N 26 
TOP C14 H143 SING N N 27 
TOP C15 O16  SING N N 28 
TOP C15 C18  SING Y N 29 
TOP O16 C17  SING N N 30 
TOP C17 H171 SING N N 31 
TOP C17 H172 SING N N 32 
TOP C17 H173 SING N N 33 
TOP C18 O19  SING N N 34 
TOP C18 C21  DOUB Y N 35 
TOP O19 C20  SING N N 36 
TOP C20 H201 SING N N 37 
TOP C20 H202 SING N N 38 
TOP C20 H203 SING N N 39 
TOP C21 H21  SING N N 40 
# 
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 
TOP SMILES           ACDLabs              10.04 "n1c(N)c(cnc1N)Cc2cc(OC)c(OC)c(OC)c2"                                                                              
TOP SMILES_CANONICAL CACTVS               3.341 "COc1cc(Cc2cnc(N)nc2N)cc(OC)c1OC"                                                                                  
TOP SMILES           CACTVS               3.341 "COc1cc(Cc2cnc(N)nc2N)cc(OC)c1OC"                                                                                  
TOP SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 "COc1cc(cc(c1OC)OC)Cc2cnc(nc2N)N"                                                                                  
TOP SMILES           "OpenEye OEToolkits" 1.5.0 "COc1cc(cc(c1OC)OC)Cc2cnc(nc2N)N"                                                                                  
TOP InChI            InChI                1.03  "InChI=1S/C14H18N4O3/c1-19-10-5-8(6-11(20-2)12(10)21-3)4-9-7-17-14(16)18-13(9)15/h5-7H,4H2,1-3H3,(H4,15,16,17,18)" 
TOP InChIKey         InChI                1.03  IEDVJHCEMCRBQM-UHFFFAOYSA-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 
TOP "SYSTEMATIC NAME" ACDLabs              10.04 "5-(3,4,5-trimethoxybenzyl)pyrimidine-2,4-diamine"         
TOP "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "5-[(3,4,5-trimethoxyphenyl)methyl]pyrimidine-2,4-diamine" 
# 
loop_
_pdbx_chem_comp_audit.comp_id 
_pdbx_chem_comp_audit.action_type 
_pdbx_chem_comp_audit.date 
_pdbx_chem_comp_audit.processing_site 
TOP "Create component"  1999-07-08 EBI  
TOP "Modify descriptor" 2011-06-04 RCSB 
# 
