data_185
# 
_chem_comp.id                                    185 
_chem_comp.name                                  (6-[4-(AMINOMETHYL)-2,6-DIMETHYLPHENOXY]-2-{[4-(AMINOMETHYL)PHENYL]AMINO}-5-BROMOPYRIMIDIN-4-YL)METHANOL 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C21 H16 Br N5 O2" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         ? 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2004-04-15 
_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                        450.288 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     185 
_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        1SUQ 
_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 
185 C1     C1     C  0 1 Y N N 144.708 -24.550 73.624 2.963  0.538  -0.018 C1     185 1  
185 O17    O17    O  0 1 N N N 144.311 -23.986 72.418 2.591  -0.768 -0.015 O17    185 2  
185 C2     C2     C  0 1 Y N N 143.967 -24.275 74.809 3.243  1.176  -1.221 C2     185 3  
185 "C2'"  "C2'"  C  0 1 N N N 142.756 -23.338 74.815 3.126  0.420  -2.519 "C2'"  185 4  
185 C3     C3     C  0 1 Y N N 144.357 -24.856 76.020 3.620  2.501  -1.228 C3     185 5  
185 C4     C4     C  0 1 Y N N 145.461 -25.724 76.067 3.727  3.202  -0.024 C4     185 6  
185 C5     C5     C  0 1 Y N N 146.210 -25.999 74.903 3.451  2.555  1.183  C5     185 7  
185 C6     C6     C  0 1 Y N N 145.836 -25.421 73.674 3.074  1.230  1.182  C6     185 8  
185 "C6'"  "C6'"  C  0 1 N N N 146.659 -25.720 72.417 2.775  0.531  2.483  "C6'"  185 9  
185 C13    C13    C  0 1 Y N N 143.327 -24.733 71.706 1.236  -0.789 -0.031 C13    185 10 
185 N12    N12    N  0 1 Y N N 142.826 -25.917 72.176 0.547  0.337  -0.170 N12    185 11 
185 C11    C11    C  0 1 Y N N 141.883 -26.620 71.483 -0.777 0.320  -0.186 C11    185 12 
185 N5     N5     N  0 1 N N N 141.370 -27.797 71.928 -1.466 1.514  -0.334 N5     185 13 
185 N16    N16    N  0 1 Y N N 141.444 -26.130 70.292 -1.460 -0.808 -0.064 N16    185 14 
185 C15    C15    C  0 1 Y N N 141.917 -24.954 69.778 -0.836 -1.968 0.079  C15    185 15 
185 C18    C18    C  0 1 N N N 141.365 -24.500 68.441 -1.625 -3.245 0.216  C18    185 16 
185 C14    C14    C  0 1 Y N N 142.885 -24.241 70.499 0.546  -1.995 0.095  C14    185 17 
185 C21    C21    C  0 1 Y N N 141.832 -28.613 72.938 -2.853 1.540  -0.197 C21    185 18 
185 C22    C22    C  0 1 Y N N 142.996 -28.354 73.763 -3.464 2.589  0.483  C22    185 19 
185 C23    C23    C  0 1 Y N N 143.383 -29.281 74.786 -4.833 2.618  0.621  C23    185 20 
185 C24    C24    C  0 1 Y N N 142.596 -30.459 74.983 -5.610 1.591  0.076  C24    185 21 
185 C25    C25    C  0 1 Y N N 141.473 -30.695 74.177 -4.993 0.538  -0.606 C25    185 22 
185 C26    C26    C  0 1 Y N N 141.098 -29.783 73.176 -3.624 0.519  -0.745 C26    185 23 
185 C27    C27    C  0 1 N N N 142.930 -31.431 75.987 -7.035 1.617  0.218  C27    185 24 
185 N27    N27    N  0 1 N N N 143.170 -32.244 76.780 -8.165 1.638  0.330  N27    185 25 
185 "C4'"  "C4'"  C  0 1 N N N 145.807 -26.307 77.320 4.119  4.579  -0.027 "C4'"  185 26 
185 "N4'"  "N4'"  N  0 1 N N N 146.083 -26.761 78.340 4.431  5.671  -0.030 "N4'"  185 27 
185 O18    O18    O  0 1 N N N 140.852 -23.352 68.244 -1.856 -3.804 -1.079 O18    185 28 
185 BR     BR     BR 0 0 N N N 143.588 -22.679 69.933 1.480  -3.627 0.296  BR     185 29 
185 "H2'1" "1H2'" H  0 0 N N N 142.175 -23.122 75.742 4.084  -0.043 -2.757 "H2'1" 185 30 
185 "H2'2" "2H2'" H  0 0 N N N 143.080 -22.362 74.384 2.364  -0.353 -2.422 "H2'2" 185 31 
185 "H2'3" "3H2'" H  0 0 N N N 142.038 -23.706 74.045 2.847  1.108  -3.317 "H2'3" 185 32 
185 H3     H3     H  0 1 N N N 143.792 -24.629 76.940 3.833  2.997  -2.164 H3     185 33 
185 H5     H5     H  0 1 N N N 147.087 -26.665 74.953 3.532  3.092  2.116  H5     185 34 
185 "H6'1" "1H6'" H  0 0 N N N 147.541 -26.401 72.456 1.717  0.643  2.721  "H6'1" 185 35 
185 "H6'2" "2H6'" H  0 0 N N N 145.964 -26.097 71.630 3.017  -0.528 2.391  "H6'2" 185 36 
185 "H6'3" "3H6'" H  0 0 N N N 146.990 -24.748 71.981 3.375  0.973  3.279  "H6'3" 185 37 
185 HN5    HN5    H  0 1 N N N 141.305 -28.394 71.103 -0.983 2.331  -0.533 HN5    185 38 
185 H181   1H18   H  0 0 N N N 142.175 -24.632 67.687 -1.063 -3.955 0.823  H181   185 39 
185 H182   2H18   H  0 0 N N N 140.611 -25.257 68.121 -2.580 -3.033 0.696  H182   185 40 
185 H22    H22    H  0 1 N N N 143.594 -27.440 73.610 -2.863 3.382  0.904  H22    185 41 
185 H23    H23    H  0 1 N N N 144.271 -29.091 75.411 -5.307 3.432  1.149  H23    185 42 
185 H25    H25    H  0 1 N N N 140.876 -31.609 74.332 -5.591 -0.257 -1.028 H25    185 43 
185 H26    H26    H  0 1 N N N 140.205 -29.990 72.562 -3.146 -0.294 -1.272 H26    185 44 
185 H18    H18    H  0 1 N N N 140.506 -23.067 67.406 -2.361 -4.617 -0.946 H18    185 45 
# 
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 
185 C1    O17    SING N N 1  
185 C1    C2     SING Y N 2  
185 C1    C6     DOUB Y N 3  
185 O17   C13    SING N N 4  
185 C2    "C2'"  SING N N 5  
185 C2    C3     DOUB Y N 6  
185 "C2'" "H2'1" SING N N 7  
185 "C2'" "H2'2" SING N N 8  
185 "C2'" "H2'3" SING N N 9  
185 C3    C4     SING Y N 10 
185 C3    H3     SING N N 11 
185 C4    C5     DOUB Y N 12 
185 C4    "C4'"  SING N N 13 
185 C5    C6     SING Y N 14 
185 C5    H5     SING N N 15 
185 C6    "C6'"  SING N N 16 
185 "C6'" "H6'1" SING N N 17 
185 "C6'" "H6'2" SING N N 18 
185 "C6'" "H6'3" SING N N 19 
185 C13   N12    SING Y N 20 
185 C13   C14    DOUB Y N 21 
185 N12   C11    DOUB Y N 22 
185 C11   N5     SING N N 23 
185 C11   N16    SING Y N 24 
185 N5    C21    SING N N 25 
185 N5    HN5    SING N N 26 
185 N16   C15    DOUB Y N 27 
185 C15   C18    SING N N 28 
185 C15   C14    SING Y N 29 
185 C18   O18    SING N N 30 
185 C18   H181   SING N N 31 
185 C18   H182   SING N N 32 
185 C14   BR     SING N N 33 
185 C21   C22    SING Y N 34 
185 C21   C26    DOUB Y N 35 
185 C22   C23    DOUB Y N 36 
185 C22   H22    SING N N 37 
185 C23   C24    SING Y N 38 
185 C23   H23    SING N N 39 
185 C24   C25    DOUB Y N 40 
185 C24   C27    SING N N 41 
185 C25   C26    SING Y N 42 
185 C25   H25    SING N N 43 
185 C26   H26    SING N N 44 
185 C27   N27    TRIP N N 45 
185 "C4'" "N4'"  TRIP N N 46 
185 O18   H18    SING N N 47 
# 
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 
185 SMILES           ACDLabs              10.04 N#Cc3cc(c(Oc1nc(nc(c1Br)CO)Nc2ccc(C#N)cc2)c(c3)C)C                                                                                                   
185 InChI            InChI                1.02b InChI=1/C21H16BrN5O2/c1-12-7-15(10-24)8-13(2)19(12)29-20-18(22)17(11-28)26-21(27-20)25-16-5-3-14(9-23)4-6-16/h3-8,28H,11H2,1-2H3,(H,25,26,27)/f/h25H 
185 InChIKey         InChI                1.02b LSIZSSASMKSUIU-LNNLXFCOCJ                                                                                                                            
185 SMILES_CANONICAL CACTVS               3.341 Cc1cc(cc(C)c1Oc2nc(Nc3ccc(cc3)C#N)nc(CO)c2Br)C#N                                                                                                     
185 SMILES           CACTVS               3.341 Cc1cc(cc(C)c1Oc2nc(Nc3ccc(cc3)C#N)nc(CO)c2Br)C#N                                                                                                     
185 SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 Cc1cc(cc(c1Oc2c(c(nc(n2)Nc3ccc(cc3)C#N)CO)Br)C)C#N                                                                                                   
185 SMILES           "OpenEye OEToolkits" 1.5.0 Cc1cc(cc(c1Oc2c(c(nc(n2)Nc3ccc(cc3)C#N)CO)Br)C)C#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 
185 "SYSTEMATIC NAME" ACDLabs              10.04 4-({5-bromo-2-[(4-cyanophenyl)amino]-6-(hydroxymethyl)pyrimidin-4-yl}oxy)-3,5-dimethylbenzonitrile 
185 "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 4-[5-bromo-2-[(4-cyanophenyl)amino]-6-(hydroxymethyl)pyrimidin-4-yl]oxy-3,5-dimethyl-benzonitrile  
# 
