data_P16
# 
_chem_comp.id                                    P16 
_chem_comp.name                                  6-(2,6-DICHLOROPHENYL)-2-{[3-(HYDROXYMETHYL)PHENYL]AMINO}-8-METHYLPYRIDO[2,3-D]PYRIMIDIN-7(8H)-ONE 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C21 H16 Cl2 N4 O2" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         PD166326 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2003-03-18 
_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                        427.283 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     P16 
_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        1OPK 
_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 
P16 O1   O1   O  0 1 N N N 49.980 11.093 14.944 0.435  0.289  -9.039 O1   P16 1  
P16 C2   C2   C  0 1 N N N 49.596 11.894 13.862 0.632  -0.842 -8.190 C2   P16 2  
P16 C3   C3   C  0 1 Y N N 49.221 13.309 14.274 -0.076 -0.618 -6.880 C3   P16 3  
P16 C4   C4   C  0 1 Y N N 50.147 14.393 14.073 -1.390 -1.023 -6.727 C4   P16 4  
P16 C5   C5   C  0 1 Y N N 49.804 15.704 14.461 -2.044 -0.819 -5.526 C5   P16 5  
P16 C6   C6   C  0 1 Y N N 48.535 15.974 15.061 -1.388 -0.209 -4.475 C6   P16 6  
P16 C7   C7   C  0 1 Y N N 47.604 14.903 15.264 -0.069 0.198  -4.625 C7   P16 7  
P16 N9   N9   N  0 1 N N N 46.330 15.046 15.874 0.598  0.816  -3.563 N9   P16 8  
P16 C10  C10  C  0 1 Y N N 45.897 16.061 16.681 0.317  0.445  -2.262 C10  P16 9  
P16 N11  N11  N  0 1 Y N N 44.614 15.902 17.177 -0.505 -0.576 -2.051 N11  P16 10 
P16 C12  C12  C  0 1 Y N N 44.155 16.860 18.002 -0.805 -0.970 -0.828 C12  P16 11 
P16 C13  C13  C  0 1 Y N N 44.925 17.997 18.377 -0.235 -0.286 0.256  C13  P16 12 
P16 C16  C16  C  0 1 Y N N 44.452 19.026 19.259 -0.519 -0.662 1.589  C16  P16 13 
P16 C17  C17  C  0 1 Y N N 45.243 20.091 19.576 0.061  0.037  2.613  C17  P16 14 
P16 C18  C18  C  0 1 Y N N 46.622 20.233 18.978 0.958  1.152  2.304  C18  P16 15 
P16 O21  O21  O  0 1 N N N 47.405 21.159 19.199 1.479  1.779  3.209  O21  P16 16 
P16 N19  N19  N  0 1 Y N N 47.062 19.177 18.103 1.210  1.488  1.025  N19  P16 17 
P16 C14  C14  C  0 1 Y N N 46.242 18.092 17.788 0.629  0.797  -0.007 C14  P16 18 
P16 N15  N15  N  0 1 Y N N 46.706 17.115 16.968 0.878  1.120  -1.271 N15  P16 19 
P16 C20  C20  C  0 1 N N N 48.407 19.246 17.479 2.110  2.607  0.732  C20  P16 20 
P16 C22  C22  C  0 1 Y N N 44.799 21.160 20.495 -0.215 -0.331 4.021  C22  P16 21 
P16 C27  C27  C  0 1 Y N N 44.264 22.389 20.017 0.591  -1.265 4.673  C27  P16 22 
P16 CL28 CL28 CL 0 0 N N N 44.060 22.644 18.299 1.924  -1.997 3.835  CL28 P16 23 
P16 C26  C26  C  0 1 Y N N 43.857 23.419 20.929 0.328  -1.604 5.986  C26  P16 24 
P16 C25  C25  C  0 1 Y N N 44.014 23.232 22.333 -0.732 -1.020 6.654  C25  P16 25 
P16 C24  C24  C  0 1 Y N N 44.543 22.010 22.844 -1.536 -0.095 6.014  C24  P16 26 
P16 C23  C23  C  0 1 Y N N 44.943 20.998 21.916 -1.281 0.256  4.703  C23  P16 27 
P16 CL29 CL29 CL 0 0 N N N 45.584 19.511 22.554 -2.291 1.418  3.902  CL29 P16 28 
P16 C8   C8   C  0 1 Y N N 47.962 13.570 14.866 0.583  -0.002 -5.835 C8   P16 29 
P16 HO1  HO1  H  0 1 N N N 50.214 10.209 14.686 0.904  0.105  -9.864 HO1  P16 30 
P16 H21  1H2  H  0 1 N N N 50.385 11.904 13.074 1.698  -0.978 -8.008 H21  P16 31 
P16 H22  2H2  H  0 1 N N N 48.770 11.415 13.285 0.230  -1.733 -8.673 H22  P16 32 
P16 H4   H4   H  0 1 N N N 51.134 14.216 13.614 -1.905 -1.499 -7.548 H4   P16 33 
P16 H5   H5   H  0 1 N N N 50.528 16.518 14.295 -3.070 -1.137 -5.410 H5   P16 34 
P16 H6   H6   H  0 1 N N N 48.275 17.002 15.365 -1.900 -0.051 -3.537 H6   P16 35 
P16 HN9  HN9  H  0 1 N N N 46.176 14.186 16.402 1.257  1.505  -3.740 HN9  P16 36 
P16 H12  H12  H  0 1 N N N 43.128 16.710 18.377 -1.474 -1.802 -0.665 H12  P16 37 
P16 H16  H16  H  0 1 N N N 43.445 18.997 19.709 -1.183 -1.487 1.797  H16  P16 38 
P16 H201 1H20 H  0 0 N N N 48.747 18.428 16.801 2.471  3.036  1.667  H201 P16 39 
P16 H202 2H20 H  0 0 N N N 48.494 20.215 16.935 2.956  2.249  0.146  H202 P16 40 
P16 H203 3H20 H  0 0 N N N 49.165 19.374 18.286 1.572  3.367  0.167  H203 P16 41 
P16 H26  H26  H  0 1 N N N 43.421 24.358 20.549 0.952  -2.326 6.491  H26  P16 42 
P16 H25  H25  H  0 1 N N N 43.724 24.037 23.028 -0.934 -1.289 7.681  H25  P16 43 
P16 H24  H24  H  0 1 N N N 44.640 21.851 23.931 -2.364 0.355  6.542  H24  P16 44 
P16 H8   H8   H  0 1 N N N 47.259 12.733 15.017 1.609  0.313  -5.954 H8   P16 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 
P16 O1  C2   SING N N 1  
P16 O1  HO1  SING N N 2  
P16 C2  C3   SING N N 3  
P16 C2  H21  SING N N 4  
P16 C2  H22  SING N N 5  
P16 C3  C4   DOUB Y N 6  
P16 C3  C8   SING Y N 7  
P16 C4  C5   SING Y N 8  
P16 C4  H4   SING N N 9  
P16 C5  C6   DOUB Y N 10 
P16 C5  H5   SING N N 11 
P16 C6  C7   SING Y N 12 
P16 C6  H6   SING N N 13 
P16 C7  N9   SING N N 14 
P16 C7  C8   DOUB Y N 15 
P16 N9  C10  SING N N 16 
P16 N9  HN9  SING N N 17 
P16 C10 N11  DOUB Y N 18 
P16 C10 N15  SING Y N 19 
P16 N11 C12  SING Y N 20 
P16 C12 C13  DOUB Y N 21 
P16 C12 H12  SING N N 22 
P16 C13 C16  SING Y N 23 
P16 C13 C14  SING Y N 24 
P16 C16 C17  DOUB Y N 25 
P16 C16 H16  SING N N 26 
P16 C17 C18  SING Y N 27 
P16 C17 C22  SING N N 28 
P16 C18 O21  DOUB N N 29 
P16 C18 N19  SING Y N 30 
P16 N19 C14  SING Y N 31 
P16 N19 C20  SING N N 32 
P16 C14 N15  DOUB Y N 33 
P16 C20 H201 SING N N 34 
P16 C20 H202 SING N N 35 
P16 C20 H203 SING N N 36 
P16 C22 C27  DOUB Y N 37 
P16 C22 C23  SING Y N 38 
P16 C27 CL28 SING N N 39 
P16 C27 C26  SING Y N 40 
P16 C26 C25  DOUB Y N 41 
P16 C26 H26  SING N N 42 
P16 C25 C24  SING Y N 43 
P16 C25 H25  SING N N 44 
P16 C24 C23  DOUB Y N 45 
P16 C24 H24  SING N N 46 
P16 C23 CL29 SING N N 47 
P16 C8  H8   SING N N 48 
# 
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 
P16 SMILES           ACDLabs              10.04 Clc4cccc(Cl)c4C3=Cc1c(nc(nc1)Nc2cc(ccc2)CO)N(C3=O)C                                                                                                     
P16 InChI            InChI                1.02b InChI=1/C21H16Cl2N4O2/c1-27-19-13(9-15(20(27)29)18-16(22)6-3-7-17(18)23)10-24-21(26-19)25-14-5-2-4-12(8-14)11-28/h2-10,28H,11H2,1H3,(H,24,25,26)/f/h25H 
P16 InChIKey         InChI                1.02b ZIQFYVPVJZEOFS-LNNLXFCOCH                                                                                                                               
P16 SMILES_CANONICAL CACTVS               3.341 CN1C(=O)C(=Cc2cnc(Nc3cccc(CO)c3)nc12)c4c(Cl)cccc4Cl                                                                                                     
P16 SMILES           CACTVS               3.341 CN1C(=O)C(=Cc2cnc(Nc3cccc(CO)c3)nc12)c4c(Cl)cccc4Cl                                                                                                     
P16 SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 CN1c2c(cnc(n2)Nc3cccc(c3)CO)C=C(C1=O)c4c(cccc4Cl)Cl                                                                                                     
P16 SMILES           "OpenEye OEToolkits" 1.5.0 CN1c2c(cnc(n2)Nc3cccc(c3)CO)C=C(C1=O)c4c(cccc4Cl)Cl                                                                                                     
# 
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 
P16 "SYSTEMATIC NAME" ACDLabs              10.04 6-(2,6-dichlorophenyl)-2-{[3-(hydroxymethyl)phenyl]amino}-8-methylpyrido[2,3-d]pyrimidin-7(8H)-one 
P16 "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 6-(2,6-dichlorophenyl)-2-[[3-(hydroxymethyl)phenyl]amino]-8-methyl-pyrido[6,5-d]pyrimidin-7-one    
# 
