data_BDM
# 
_chem_comp.id                                    BDM 
_chem_comp.name                                  BRODIMOPRIM-4,6-DICARBOXYLATE 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C20 H24 Br N4 O6" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         ? 
_chem_comp.pdbx_formal_charge                    -1 
_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                        496.332 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     BDM 
_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        1DIU 
_chem_comp.pdbx_subcomponent_list                ? 
_chem_comp.pdbx_processing_site                  PDBJ 
# 
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 
BDM N1   N1   N  1  1 Y N N -4.664 31.619 20.815 4.451  -4.135 0.578  N1   BDM 1  
BDM C2   C2   C  0  1 Y N N -4.725 30.390 21.306 3.386  -4.640 1.184  C2   BDM 2  
BDM N2   N2   N  0  1 N N N -5.878 29.975 21.794 3.562  -5.564 2.199  N2   BDM 3  
BDM N3   N3   N  0  1 Y N N -3.727 29.539 21.420 2.157  -4.282 0.843  N3   BDM 4  
BDM C4   C4   C  0  1 Y N N -2.509 29.980 21.145 1.956  -3.393 -0.125 C4   BDM 5  
BDM N4   N4   N  0  1 N N N -1.531 29.086 21.144 0.670  -3.020 -0.480 N4   BDM 6  
BDM C5   C5   C  0  1 Y N N -2.289 31.343 20.782 3.059  -2.848 -0.786 C5   BDM 7  
BDM C6   C6   C  0  1 Y N N -3.453 32.110 20.539 4.323  -3.249 -0.398 C6   BDM 8  
BDM C7   C7   C  0  1 N N N -0.909 31.995 20.740 2.875  -1.841 -1.892 C7   BDM 9  
BDM C8   C8   C  0  1 Y N N -0.848 33.504 20.837 2.733  -0.463 -1.298 C8   BDM 10 
BDM C9   C9   C  0  1 Y N N -1.317 34.406 21.810 1.481  0.018  -0.965 C9   BDM 11 
BDM C10  C10  C  0  1 Y N N -1.054 35.784 21.665 1.347  1.286  -0.419 C10  BDM 12 
BDM O10  O10  O  0  1 N N N -1.333 36.804 22.557 0.115  1.759  -0.091 O10  BDM 13 
BDM C11  C11  C  0  1 Y N N -0.405 36.241 20.526 2.471  2.069  -0.202 C11  BDM 14 
BDM BR11 BR11 BR 0  0 N N N -0.151 38.131 20.214 2.293  3.798  0.542  BR11 BDM 15 
BDM C12  C12  C  0  1 Y N N 0.097  35.336 19.604 3.726  1.585  -0.542 C12  BDM 16 
BDM O12  O12  O  0  1 N N N 0.823  35.787 18.530 4.829  2.352  -0.336 O12  BDM 17 
BDM C13  C13  C  0  1 Y N N -0.120 33.974 19.769 3.854  0.316  -1.088 C13  BDM 18 
BDM C14  C14  C  0  1 N N N 2.222  35.661 18.774 5.952  1.585  -0.775 C14  BDM 19 
BDM C15  C15  C  0  1 N N N -2.242 36.675 23.651 -0.823 0.733  -0.423 C15  BDM 20 
BDM C16  C16  C  0  1 N N N -2.533 38.081 24.192 -2.237 1.204  -0.077 C16  BDM 21 
BDM C17  C17  C  0  1 N N N -3.879 38.196 24.930 -3.241 0.106  -0.433 C17  BDM 22 
BDM C18  C18  C  0  1 N N S -3.874 39.189 26.112 -4.655 0.577  -0.087 C18  BDM 23 
BDM C19  C19  C  0  1 N N N -5.363 39.556 26.292 -5.670 -0.468 -0.556 C19  BDM 24 
BDM C20  C20  C  0  1 N N N -6.003 39.978 24.942 -7.088 0.058  -0.324 C20  BDM 25 
BDM C21  C21  C  0  1 N N N -3.205 38.622 27.399 -4.774 0.758  1.404  C21  BDM 26 
BDM OXV  1O21 O  0  1 N N N -2.681 39.400 28.221 -5.068 1.902  1.886  OXV  BDM 27 
BDM OXW  2O21 O  -1 1 N N N -3.309 37.405 27.625 -4.579 -0.232 2.184  OXW  BDM 28 
BDM C22  C22  C  0  1 N N N -7.523 40.225 24.904 -8.087 -0.972 -0.786 C22  BDM 29 
BDM OX5  1O22 O  0  1 N N N -8.268 39.634 25.718 -7.683 -2.076 -1.279 OX5  BDM 30 
BDM OX6  2O22 O  -1 1 N N N -7.997 40.976 24.024 -9.336 -0.738 -0.683 OX6  BDM 31 
BDM HN1  HN1  H  0  1 N N N -5.525 32.041 20.447 5.337  -4.419 0.854  HN1  BDM 32 
BDM HN21 1HN2 H  0  0 N N N -6.664 30.632 21.738 4.456  -5.834 2.459  HN21 BDM 33 
BDM HN22 2HN2 H  0  0 N N N -5.895 29.029 22.191 2.790  -5.941 2.651  HN22 BDM 34 
BDM HN41 1HN4 H  0  0 N N N -0.635 29.409 20.767 -0.092 -3.408 -0.022 HN41 BDM 35 
BDM HN42 2HN4 H  0  0 N N N -1.835 28.113 21.269 0.530  -2.371 -1.188 HN42 BDM 36 
BDM H6   H6   H  0  1 N N N -3.353 33.105 20.101 5.197  -2.844 -0.886 H6   BDM 37 
BDM H71  1H7  H  0  1 N N N -0.404 31.688 19.806 1.978  -2.086 -2.461 H71  BDM 38 
BDM H72  2H7  H  0  1 N N N -0.277 31.585 21.550 3.742  -1.865 -2.552 H72  BDM 39 
BDM H9   H9   H  0  1 N N N -1.789 34.079 22.717 0.606  -0.594 -1.130 H9   BDM 40 
BDM H13  H13  H  0  1 N N N 0.268  33.272 19.046 4.831  -0.063 -1.349 H13  BDM 41 
BDM H141 1H14 H  0  0 N N N 2.517  36.229 19.682 6.866  2.162  -0.628 H141 BDM 42 
BDM H142 2H14 H  0  0 N N N 2.509  34.601 18.940 6.009  0.662  -0.198 H142 BDM 43 
BDM H143 3H14 H  0  0 N N N 2.787  36.045 17.916 5.839  1.347  -1.832 H143 BDM 44 
BDM H151 1H15 H  0  0 N N N -3.148 36.135 23.364 -0.762 0.517  -1.490 H151 BDM 45 
BDM H152 2H15 H  0  0 N N N -1.810 36.018 24.393 -0.591 -0.168 0.144  H152 BDM 46 
BDM H161 1H16 H  0  0 N N N -1.695 38.391 24.842 -2.297 1.421  0.989  H161 BDM 47 
BDM H162 2H16 H  0  0 N N N -2.527 38.816 23.364 -2.468 2.106  -0.644 H162 BDM 48 
BDM H171 1H17 H  0  0 N N N -4.226 37.209 25.296 -3.181 -0.110 -1.499 H171 BDM 49 
BDM H172 2H17 H  0  0 N N N -4.657 38.505 24.208 -3.010 -0.795 0.134  H172 BDM 50 
BDM H18  H18  H  0  1 N N N -3.328 40.108 25.827 -4.854 1.526  -0.585 H18  BDM 51 
BDM H191 1H19 H  0  0 N N N -5.904 38.679 26.695 -5.524 -0.664 -1.618 H191 BDM 52 
BDM H192 2H19 H  0  0 N N N -5.477 40.359 27.044 -5.527 -1.391 0.007  H192 BDM 53 
BDM H201 1H20 H  0  0 N N N -5.503 40.889 24.569 -7.233 0.254  0.739  H201 BDM 54 
BDM H202 2H20 H  0  0 N N N -5.790 39.199 24.188 -7.230 0.980  -0.886 H202 BDM 55 
# 
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 
BDM N1  C2   SING Y N 1  
BDM N1  C6   DOUB Y N 2  
BDM N1  HN1  SING N N 3  
BDM C2  N2   SING N N 4  
BDM C2  N3   DOUB Y N 5  
BDM N2  HN21 SING N N 6  
BDM N2  HN22 SING N N 7  
BDM N3  C4   SING Y N 8  
BDM C4  N4   SING N N 9  
BDM C4  C5   DOUB Y N 10 
BDM N4  HN41 SING N N 11 
BDM N4  HN42 SING N N 12 
BDM C5  C6   SING Y N 13 
BDM C5  C7   SING N N 14 
BDM C6  H6   SING N N 15 
BDM C7  C8   SING N N 16 
BDM C7  H71  SING N N 17 
BDM C7  H72  SING N N 18 
BDM C8  C9   DOUB Y N 19 
BDM C8  C13  SING Y N 20 
BDM C9  C10  SING Y N 21 
BDM C9  H9   SING N N 22 
BDM C10 O10  SING N N 23 
BDM C10 C11  DOUB Y N 24 
BDM O10 C15  SING N N 25 
BDM C11 BR11 SING N N 26 
BDM C11 C12  SING Y N 27 
BDM C12 O12  SING N N 28 
BDM C12 C13  DOUB Y N 29 
BDM O12 C14  SING N N 30 
BDM C13 H13  SING N N 31 
BDM C14 H141 SING N N 32 
BDM C14 H142 SING N N 33 
BDM C14 H143 SING N N 34 
BDM C15 C16  SING N N 35 
BDM C15 H151 SING N N 36 
BDM C15 H152 SING N N 37 
BDM C16 C17  SING N N 38 
BDM C16 H161 SING N N 39 
BDM C16 H162 SING N N 40 
BDM C17 C18  SING N N 41 
BDM C17 H171 SING N N 42 
BDM C17 H172 SING N N 43 
BDM C18 C19  SING N N 44 
BDM C18 C21  SING N N 45 
BDM C18 H18  SING N N 46 
BDM C19 C20  SING N N 47 
BDM C19 H191 SING N N 48 
BDM C19 H192 SING N N 49 
BDM C20 C22  SING N N 50 
BDM C20 H201 SING N N 51 
BDM C20 H202 SING N N 52 
BDM C21 OXV  DOUB N N 53 
BDM C21 OXW  SING N N 54 
BDM C22 OX5  DOUB N N 55 
BDM C22 OX6  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 
BDM SMILES           ACDLabs              10.04 [O-]C(=O)C(CCC([O-])=O)CCCOc1c(Br)c(OC)cc(c1)Cc2c(nc(N)[nH+]c2)N 
BDM InChI            InChI                1.02b 
InChI=1/C20H25BrN4O6/c1-30-14-8-11(7-13-10-24-20(23)25-18(13)22)9-15(17(14)21)31-6-2-3-12(19(28)29)4-5-16(26)27/h8-10,12H,2-7H2,1H3,(H,26,27)(H,28,29)(H4,22,23,24,25)/p-1/t12-/m0/s1/fC20H24BrN4O6/h24H,22-23H2/q-1 
BDM InChIKey         InChI                1.02b SZAVCZNFKJSWRN-YHNVOYINDG 
BDM SMILES_CANONICAL CACTVS               3.341 COc1cc(Cc2c[nH+]c(N)nc2N)cc(OCCC[C@@H](CCC([O-])=O)C([O-])=O)c1Br 
BDM SMILES           CACTVS               3.341 COc1cc(Cc2c[nH+]c(N)nc2N)cc(OCCC[CH](CCC([O-])=O)C([O-])=O)c1Br 
BDM SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 COc1cc(cc(c1Br)OCCC[C@@H](CCC(=O)[O-])C(=O)[O-])Cc2c[nH+]c(nc2N)N 
BDM SMILES           "OpenEye OEToolkits" 1.5.0 COc1cc(cc(c1Br)OCCCC(CCC(=O)[O-])C(=O)[O-])Cc2c[nH+]c(nc2N)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 
BDM "SYSTEMATIC NAME" ACDLabs              10.04 (2S)-2-(3-{2-bromo-5-[(2,4-diaminopyrimidin-1-ium-5-yl)methyl]-3-methoxyphenoxy}propyl)pentanedioate  
BDM "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 (2S)-2-[3-[2-bromo-5-[(2,4-diaminopyrimidin-1-ium-5-yl)methyl]-3-methoxy-phenoxy]propyl]pentanedioate 
# 
