data_53R
# 
_chem_comp.id                                    53R 
_chem_comp.name                                  5-[(3R)-3-(5-methoxybiphenyl-3-yl)but-1-yn-1-yl]-6-methylpyrimidine-2,4-diamine 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C22 H22 N4 O" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         ? 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2008-09-15 
_chem_comp.pdbx_modified_date                    2009-03-20 
_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                        358.436 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     53R 
_chem_comp.pdbx_model_coordinates_details        ? 
_chem_comp.pdbx_model_coordinates_missing_flag   N 
_chem_comp.pdbx_ideal_coordinates_details        Corina 
_chem_comp.pdbx_ideal_coordinates_missing_flag   N 
_chem_comp.pdbx_model_coordinates_db_code        3EEJ 
_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 
53R C20  C20  C 0 1 Y N N 8.932  -5.519  -5.511 -5.306 -0.234 -1.031 C20  53R 1  
53R C21  C21  C 0 1 Y N N 7.827  -6.029  -6.176 -6.414 0.310  -1.648 C21  53R 2  
53R C22  C22  C 0 1 Y N N 7.710  -5.821  -7.566 -6.538 1.683  -1.768 C22  53R 3  
53R C23  C23  C 0 1 Y N N 8.678  -5.096  -8.285 -5.553 2.517  -1.271 C23  53R 4  
53R C24  C24  C 0 1 Y N N 9.789  -4.590  -7.598 -4.440 1.984  -0.653 C24  53R 5  
53R C25  C25  C 0 1 Y N N 9.897  -4.800  -6.214 -4.311 0.602  -0.529 C25  53R 6  
53R C18  C18  C 0 1 Y N N 10.984 -4.306  -5.514 -3.117 0.023  0.135  C18  53R 7  
53R C19  C19  C 0 1 Y N N 11.435 -5.006  -4.378 -2.122 0.859  0.637  C19  53R 8  
53R C17  C17  C 0 1 Y N N 11.627 -3.126  -5.945 -2.990 -1.358 0.264  C17  53R 9  
53R C16  C16  C 0 1 Y N N 12.733 -2.608  -5.271 -1.874 -1.893 0.885  C16  53R 10 
53R O17  O17  O 0 1 N N N 13.367 -1.424  -5.674 -1.747 -3.240 1.012  O17  53R 11 
53R C2   C2   C 0 1 N N N 14.752 -1.144  -5.058 -2.803 -4.044 0.483  C2   53R 12 
53R C15  C15  C 0 1 Y N N 13.159 -3.295  -4.128 -0.884 -1.053 1.377  C15  53R 13 
53R C14  C14  C 0 1 Y N N 12.531 -4.470  -3.712 -1.012 0.318  1.255  C14  53R 14 
53R C12  C12  C 0 1 N N S 13.084 -5.081  -2.464 0.063  1.224  1.797  C12  53R 15 
53R C13  C13  C 0 1 N N N 11.977 -5.074  -1.397 0.209  0.998  3.303  C13  53R 16 
53R C11  C11  C 0 1 N N N 13.776 -6.367  -2.731 1.340  0.923  1.130  C11  53R 17 
53R C10  C10  C 0 1 N N N 14.389 -7.357  -2.871 2.359  0.683  0.598  C10  53R 18 
53R C6   C6   C 0 1 Y N N 15.139 -8.548  -2.927 3.602  0.391  -0.051 C6   53R 19 
53R C5   C5   C 0 1 Y N N 15.267 -9.251  -4.140 4.762  1.094  0.273  C5   53R 20 
53R C8   C8   C 0 1 N N N 14.616 -8.796  -5.471 4.730  2.181  1.317  C8   53R 21 
53R N4   N4   N 0 1 Y N N 15.990 -10.379 -4.135 5.891  0.794  -0.348 N4   53R 22 
53R C3   C3   C 0 1 Y N N 16.602 -10.823 -3.031 5.934  -0.159 -1.268 C3   53R 23 
53R N7   N7   N 0 1 N N N 17.289 -11.969 -3.057 7.137  -0.437 -1.890 N7   53R 24 
53R N2   N2   N 0 1 Y N N 16.477 -10.186 -1.892 4.858  -0.854 -1.609 N2   53R 25 
53R C1   C1   C 0 1 Y N N 15.782 -9.051  -1.761 3.687  -0.620 -1.030 C1   53R 26 
53R N9   N9   N 0 1 N N N 15.746 -8.464  -0.541 2.568  -1.351 -1.385 N9   53R 27 
53R H20  H20  H 0 1 N N N 9.045  -5.679  -4.449 -5.212 -1.305 -0.934 H20  53R 28 
53R H21  H21  H 0 1 N N N 7.068  -6.577  -5.638 -7.186 -0.337 -2.038 H21  53R 29 
53R H22  H22  H 0 1 N N N 6.858  -6.228  -8.090 -7.406 2.104  -2.252 H22  53R 30 
53R H23  H23  H 0 1 N N N 8.567  -4.933  -9.347 -5.654 3.588  -1.368 H23  53R 31 
53R H24  H24  H 0 1 N N N 10.555 -4.044  -8.128 -3.672 2.636  -0.266 H24  53R 32 
53R H19  H19  H 0 1 N N N 10.954 -5.913  -4.042 -2.219 1.931  0.543  H19  53R 33 
53R H17  H17  H 0 1 N N N 11.254 -2.611  -6.818 -3.761 -2.011 -0.119 H17  53R 34 
53R H2   H2   H 0 1 N N N 15.503 -1.077  -5.859 -3.739 -3.790 0.981  H2   53R 35 
53R H2A  H2A  H 0 1 N N N 14.721 -0.194  -4.504 -2.899 -3.859 -0.587 H2A  53R 36 
53R H2B  H2B  H 0 1 N N N 15.020 -1.961  -4.372 -2.577 -5.097 0.650  H2B  53R 37 
53R H15  H15  H 0 1 N N N 13.990 -2.908  -3.557 -0.014 -1.472 1.861  H15  53R 38 
53R H12  H12  H 0 1 N N N 13.906 -4.484  -2.042 -0.209 2.263  1.610  H12  53R 39 
53R H13  H13  H 0 1 N N N 12.432 -5.072  -0.396 0.987  1.654  3.695  H13  53R 40 
53R H13A H13A H 0 0 N N N 11.356 -4.174  -1.519 -0.737 1.221  3.797  H13A 53R 41 
53R H13B H13B H 0 0 N N N 11.351 -5.971  -1.513 0.481  -0.041 3.490  H13B 53R 42 
53R H8   H8   H 0 1 N N N 13.530 -8.688  -5.331 4.939  1.750  2.296  H8   53R 43 
53R H8A  H8A  H 0 1 N N N 15.044 -7.830  -5.777 5.484  2.933  1.082  H8A  53R 44 
53R H8B  H8B  H 0 1 N N N 14.812 -9.547  -6.250 3.744  2.646  1.327  H8B  53R 45 
53R HN7  HN7  H 0 1 N N N 17.461 -12.234 -4.006 7.933  0.062  -1.651 HN7  53R 46 
53R HN7A HN7A H 0 0 N N N 18.161 -11.846 -2.583 7.185  -1.132 -2.565 HN7A 53R 47 
53R HN9  HN9  H 0 1 N N N 15.737 -9.169  0.168  1.715  -1.171 -0.959 HN9  53R 48 
53R HN9A HN9A H 0 0 N N N 16.553 -7.885  -0.426 2.636  -2.045 -2.059 HN9A 53R 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 
53R C20 C21  DOUB Y N 1  
53R C20 C25  SING Y N 2  
53R C21 C22  SING N N 3  
53R C22 C23  DOUB Y N 4  
53R C23 C24  SING N N 5  
53R C24 C25  DOUB Y N 6  
53R C25 C18  SING N N 7  
53R C18 C19  DOUB Y N 8  
53R C18 C17  SING N N 9  
53R C19 C14  SING Y N 10 
53R C17 C16  DOUB N N 11 
53R C16 O17  SING N N 12 
53R C16 C15  SING Y N 13 
53R O17 C2   SING Y N 14 
53R C15 C14  DOUB Y N 15 
53R C14 C12  SING N N 16 
53R C12 C13  SING Y N 17 
53R C12 C11  SING N N 18 
53R C11 C10  TRIP N N 19 
53R C10 C6   SING Y N 20 
53R C6  C5   DOUB N N 21 
53R C6  C1   SING N N 22 
53R C5  C8   SING N N 23 
53R C5  N4   SING N N 24 
53R N4  C3   DOUB Y N 25 
53R C3  N7   SING N N 26 
53R C3  N2   SING N N 27 
53R N2  C1   DOUB N N 28 
53R C1  N9   SING N N 29 
53R C20 H20  SING N N 30 
53R C21 H21  SING N N 31 
53R C22 H22  SING N N 32 
53R C23 H23  SING N N 33 
53R C24 H24  SING N N 34 
53R C19 H19  SING N N 35 
53R C17 H17  SING Y N 36 
53R C2  H2   SING Y N 37 
53R C2  H2A  SING N N 38 
53R C2  H2B  SING Y N 39 
53R C15 H15  SING N N 40 
53R C12 H12  SING N N 41 
53R C13 H13  SING N N 42 
53R C13 H13A SING Y N 43 
53R C13 H13B SING N N 44 
53R C8  H8   SING Y N 45 
53R C8  H8A  SING N N 46 
53R C8  H8B  SING N N 47 
53R N7  HN7  SING Y N 48 
53R N7  HN7A SING N N 49 
53R N9  HN9  SING N N 50 
53R N9  HN9A SING N N 51 
# 
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 
53R SMILES           ACDLabs              10.04 C(#CC(c2cc(c1ccccc1)cc(OC)c2)C)c3c(nc(nc3C)N)N                                                                                                               
53R InChI            InChI                1.02b InChI=1/C22H22N4O/c1-14(9-10-20-15(2)25-22(24)26-21(20)23)17-11-18(13-19(12-17)27-3)16-7-5-4-6-8-16/h4-8,11-14H,1-3H3,(H4,23,24,25,26)/t14-/m0/s1/f/h23-24H2 
53R InChIKey         InChI                1.02b JPENSYBRTSIYGO-WMEIHOAQDJ                                                                                                                                    
53R SMILES_CANONICAL CACTVS               3.341 COc1cc(cc(c1)c2ccccc2)[C@@H](C)C#Cc3c(C)nc(N)nc3N                                                                                                            
53R SMILES           CACTVS               3.341 COc1cc(cc(c1)c2ccccc2)[CH](C)C#Cc3c(C)nc(N)nc3N                                                                                                              
53R SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 Cc1c(c(nc(n1)N)N)C#C[C@H](C)c2cc(cc(c2)OC)c3ccccc3                                                                                                           
53R SMILES           "OpenEye OEToolkits" 1.5.0 Cc1c(c(nc(n1)N)N)C#CC(C)c2cc(cc(c2)OC)c3ccccc3                                                                                                               
# 
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 
53R "SYSTEMATIC NAME" ACDLabs              10.04 5-[(3R)-3-(5-methoxybiphenyl-3-yl)but-1-yn-1-yl]-6-methylpyrimidine-2,4-diamine  
53R "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 5-[(3R)-3-(3-methoxy-5-phenyl-phenyl)but-1-ynyl]-6-methyl-pyrimidine-2,4-diamine 
# 
