data_65B
# 
_chem_comp.id                                    65B 
_chem_comp.name                                  4-({6-AMINO-5-BROMO-2-[(4-CYANOPHENYL)AMINO]PYRIMIDIN-4-YL}OXY)-3,5-DIMETHYLBENZONITRILE 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C20 H15 Br N6 O" 
_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                        435.277 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     65B 
_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        1SV5 
_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 
65B C1     C1     C  0 1 Y N N 142.792 -23.495 70.420 0.563  -0.041 2.868  C1     65B 1  
65B O17    O17    O  0 1 N N N 142.931 -24.097 69.133 -0.760 -0.024 2.570  O17    65B 2  
65B C2     C2     C  0 1 Y N N 142.513 -22.048 70.545 1.232  -1.254 2.983  C2     65B 3  
65B "C2'"  "C2'"  C  0 1 N N N 142.347 -21.111 69.333 0.487  -2.547 2.771  "C2'"  65B 4  
65B C3     C3     C  0 1 Y N N 142.372 -21.457 71.841 2.576  -1.276 3.285  C3     65B 5  
65B C4     C4     C  0 1 Y N N 142.507 -22.241 73.019 3.266  -0.077 3.481  C4     65B 6  
65B C5     C5     C  0 1 Y N N 142.776 -23.638 72.927 2.588  1.140  3.370  C5     65B 7  
65B C6     C6     C  0 1 Y N N 142.931 -24.288 71.658 1.244  1.153  3.068  C6     65B 8  
65B "C6'"  "C6'"  C  0 1 N N N 143.230 -25.803 71.656 0.513  2.465  2.947  "C6'"  65B 9  
65B C13    C13    C  0 1 Y N N 141.705 -24.841 68.768 -0.857 0.029  1.219  C13    65B 10 
65B N12    N12    N  0 1 Y N N 141.329 -25.977 69.466 0.238  0.054  0.466  N12    65B 11 
65B C11    C11    C  0 1 Y N N 140.161 -26.732 69.173 0.153  0.105  -0.854 C11    65B 12 
65B N5     N5     N  0 1 N N N 139.786 -27.862 69.875 1.317  0.129  -1.604 N5     65B 13 
65B N16    N16    N  0 1 Y N N 139.368 -26.306 68.120 -1.015 0.134  -1.476 N16    65B 14 
65B C15    C15    C  0 1 Y N N 139.695 -25.180 67.388 -2.153 0.112  -0.787 C15    65B 15 
65B N18    N18    N  0 1 N N N 138.887 -24.843 66.395 -3.373 0.142  -1.445 N18    65B 16 
65B C14    C14    C  0 1 Y N N 140.877 -24.423 67.710 -2.102 0.052  0.603  C14    65B 17 
65B C21    C21    C  0 1 Y N N 140.556 -28.626 70.758 1.251  0.067  -2.995 C21    65B 18 
65B C22    C22    C  0 1 Y N N 140.764 -28.368 72.243 0.254  -0.683 -3.610 C22    65B 19 
65B C23    C23    C  0 1 Y N N 141.598 -29.244 73.048 0.183  -0.742 -4.983 C23    65B 20 
65B C24    C24    C  0 1 Y N N 142.218 -30.375 72.378 1.120  -0.054 -5.761 C24    65B 21 
65B C25    C25    C  0 1 Y N N 142.015 -30.618 70.975 2.124  0.694  -5.139 C25    65B 22 
65B C26    C26    C  0 1 Y N N 141.194 -29.755 70.182 2.186  0.752  -3.766 C26    65B 23 
65B C27    C27    C  0 1 N N N 143.060 -31.290 73.094 1.052  -0.117 -7.190 C27    65B 24 
65B N27    N27    N  0 1 N N N 143.768 -32.046 73.642 0.997  -0.167 -8.323 N27    65B 25 
65B "C4'"  "C4'"  C  0 1 N N N 142.358 -21.619 74.296 4.663  -0.095 3.795  "C4'"  65B 26 
65B "N4'"  "N4'"  N  0 1 N N N 142.208 -21.156 75.345 5.771  -0.109 4.045  "N4'"  65B 27 
65B BR     BR     BR 0 0 N N N 141.314 -22.940 66.790 -3.690 0.018  1.630  BR     65B 28 
65B "H2'1" "1H2'" H  0 0 N N N 142.136 -20.020 69.427 0.082  -2.893 3.722  "H2'1" 65B 29 
65B "H2'2" "2H2'" H  0 0 N N N 143.260 -21.219 68.702 -0.327 -2.385 2.066  "H2'2" 65B 30 
65B "H2'3" "3H2'" H  0 0 N N N 141.552 -21.547 68.682 1.169  -3.298 2.372  "H2'3" 65B 31 
65B H3     H3     H  0 1 N N N 142.155 -20.379 71.933 3.095  -2.219 3.370  H3     65B 32 
65B H5     H5     H  0 1 N N N 142.865 -24.227 73.855 3.118  2.069  3.521  H5     65B 33 
65B "H6'1" "1H6'" H  0 0 N N N 143.334 -26.401 72.590 0.562  2.815  1.916  "H6'1" 65B 34 
65B "H6'2" "2H6'" H  0 0 N N N 142.450 -26.296 71.029 -0.528 2.328  3.235  "H6'2" 65B 35 
65B "H6'3" "3H6'" H  0 0 N N N 144.155 -25.959 71.053 0.977  3.201  3.603  "H6'3" 65B 36 
65B HN5    HN5    H  0 1 N N N 139.436 -28.517 69.175 2.179  0.189  -1.162 HN5    65B 37 
65B H181   1H18   H  0 0 N N N 139.128 -24.012 65.854 -3.401 0.180  -2.414 H181   65B 38 
65B H182   2H18   H  0 0 N N N 137.935 -24.750 66.750 -4.199 0.126  -0.936 H182   65B 39 
65B H22    H22    H  0 1 N N N 140.292 -27.513 72.755 -0.468 -1.214 -3.009 H22    65B 40 
65B H23    H23    H  0 1 N N N 141.754 -29.058 74.123 -0.593 -1.321 -5.460 H23    65B 41 
65B H25    H25    H  0 1 N N N 142.499 -31.485 70.496 2.849  1.226  -5.737 H25    65B 42 
65B H26    H26    H  0 1 N N N 141.050 -29.963 69.108 2.961  1.331  -3.285 H26    65B 43 
# 
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 
65B C1    O17    SING N N 1  
65B C1    C2     SING Y N 2  
65B C1    C6     DOUB Y N 3  
65B O17   C13    SING N N 4  
65B C2    "C2'"  SING N N 5  
65B C2    C3     DOUB Y N 6  
65B "C2'" "H2'1" SING N N 7  
65B "C2'" "H2'2" SING N N 8  
65B "C2'" "H2'3" SING N N 9  
65B C3    C4     SING Y N 10 
65B C3    H3     SING N N 11 
65B C4    C5     DOUB Y N 12 
65B C4    "C4'"  SING N N 13 
65B C5    C6     SING Y N 14 
65B C5    H5     SING N N 15 
65B C6    "C6'"  SING N N 16 
65B "C6'" "H6'1" SING N N 17 
65B "C6'" "H6'2" SING N N 18 
65B "C6'" "H6'3" SING N N 19 
65B C13   N12    SING Y N 20 
65B C13   C14    DOUB Y N 21 
65B N12   C11    DOUB Y N 22 
65B C11   N5     SING N N 23 
65B C11   N16    SING Y N 24 
65B N5    C21    SING N N 25 
65B N5    HN5    SING N N 26 
65B N16   C15    DOUB Y N 27 
65B C15   N18    SING N N 28 
65B C15   C14    SING Y N 29 
65B N18   H181   SING N N 30 
65B N18   H182   SING N N 31 
65B C14   BR     SING N N 32 
65B C21   C22    SING Y N 33 
65B C21   C26    DOUB Y N 34 
65B C22   C23    DOUB Y N 35 
65B C22   H22    SING N N 36 
65B C23   C24    SING Y N 37 
65B C23   H23    SING N N 38 
65B C24   C25    DOUB Y N 39 
65B C24   C27    SING N N 40 
65B C25   C26    SING Y N 41 
65B C25   H25    SING N N 42 
65B C26   H26    SING N N 43 
65B C27   N27    TRIP N N 44 
65B "C4'" "N4'"  TRIP N N 45 
# 
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 
65B SMILES           ACDLabs              10.04 N#Cc3cc(c(Oc1nc(nc(c1Br)N)Nc2ccc(C#N)cc2)c(c3)C)C                                                                                                 
65B InChI            InChI                1.02b InChI=1/C20H15BrN6O/c1-11-7-14(10-23)8-12(2)17(11)28-19-16(21)18(24)26-20(27-19)25-15-5-3-13(9-22)4-6-15/h3-8H,1-2H3,(H3,24,25,26,27)/f/h25H,24H2 
65B InChIKey         InChI                1.02b PYGWGZALEOIKDF-JAFMVTPMCX                                                                                                                         
65B SMILES_CANONICAL CACTVS               3.341 Cc1cc(cc(C)c1Oc2nc(Nc3ccc(cc3)C#N)nc(N)c2Br)C#N                                                                                                   
65B SMILES           CACTVS               3.341 Cc1cc(cc(C)c1Oc2nc(Nc3ccc(cc3)C#N)nc(N)c2Br)C#N                                                                                                   
65B SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 Cc1cc(cc(c1Oc2c(c(nc(n2)Nc3ccc(cc3)C#N)N)Br)C)C#N                                                                                                 
65B SMILES           "OpenEye OEToolkits" 1.5.0 Cc1cc(cc(c1Oc2c(c(nc(n2)Nc3ccc(cc3)C#N)N)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 
65B "SYSTEMATIC NAME" ACDLabs              10.04 4-({6-amino-5-bromo-2-[(4-cyanophenyl)amino]pyrimidin-4-yl}oxy)-3,5-dimethylbenzonitrile 
65B "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 4-[6-amino-5-bromo-2-[(4-cyanophenyl)amino]pyrimidin-4-yl]oxy-3,5-dimethyl-benzonitrile  
# 
