data_N22
# 
_chem_comp.id                                    N22 
_chem_comp.name                                  5-[3-(2,5-dimethoxyphenyl)prop-1-yn-1-yl]-6-ethylpyrimidine-2,4-diamine 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C17 H20 N4 O2" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         ? 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2008-04-11 
_chem_comp.pdbx_modified_date                    2008-11-21 
_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                        312.366 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     N22 
_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        3CSE 
_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 
N22 C8   C8   C 0 1 N N N 28.941 6.377  37.521 -3.568 1.470  2.763  C8   N22 1  
N22 C7   C7   C 0 1 N N N 30.122 7.119  36.933 -3.581 1.837  1.277  C7   N22 2  
N22 C5   C5   C 0 1 Y N N 30.451 6.376  35.619 -3.568 0.578  0.449  C5   N22 3  
N22 N4   N4   N 0 1 Y N N 31.494 5.552  35.693 -4.703 0.003  0.086  N4   N22 4  
N22 C3   C3   C 0 1 Y N N 31.985 4.923  34.590 -4.707 -1.104 -0.643 C3   N22 5  
N22 N8   N8   N 0 1 N N N 33.027 4.162  34.687 -5.918 -1.669 -0.998 N8   N22 6  
N22 N2   N2   N 0 1 Y N N 31.325 5.022  33.426 -3.585 -1.685 -1.042 N2   N22 7  
N22 C1   C1   C 0 1 Y N N 30.262 5.789  33.249 -2.403 -1.173 -0.721 C1   N22 8  
N22 N7   N7   N 0 1 N N N 29.626 5.858  32.030 -1.235 -1.783 -1.140 N7   N22 9  
N22 C6   C6   C 0 1 Y N N 29.791 6.540  34.374 -2.360 0.007  0.048  C6   N22 10 
N22 C9   C9   C 0 1 N N N 28.700 7.412  34.202 -1.109 0.601  0.414  C9   N22 11 
N22 C10  C10  C 0 1 N N N 27.789 8.144  34.072 -0.084 1.089  0.714  C10  N22 12 
N22 C11  C11  C 0 1 N N N 26.695 9.056  33.878 1.202  1.699  1.089  C11  N22 13 
N22 C13  C13  C 0 1 Y N N 26.343 9.799  35.207 2.332  0.877  0.525  C13  N22 14 
N22 C18  C18  C 0 1 Y N N 26.954 10.993 35.698 2.939  -0.088 1.304  C18  N22 15 
N22 C17  C17  C 0 1 Y N N 26.418 11.435 36.959 3.980  -0.845 0.785  C17  N22 16 
N22 O2   O2   O 0 1 N N N 26.793 12.573 37.650 4.578  -1.796 1.552  O2   N22 17 
N22 C4   C4   C 0 1 N N N 27.705 13.467 36.934 5.642  -2.537 0.953  C4   N22 18 
N22 C16  C16  C 0 1 Y N N 25.384 10.719 37.561 4.410  -0.632 -0.516 C16  N22 19 
N22 C15  C15  C 0 1 Y N N 24.815 9.536  37.048 3.803  0.334  -1.295 C15  N22 20 
N22 C14  C14  C 0 1 Y N N 25.335 9.121  35.841 2.759  1.087  -0.778 C14  N22 21 
N22 O10  O10  O 0 1 N N N 24.928 8.055  35.154 2.158  2.034  -1.546 O10  N22 22 
N22 C2   C2   C 0 1 N N N 23.915 7.152  35.624 2.648  2.196  -2.878 C2   N22 23 
N22 H8   H8   H 0 1 N N N 29.117 6.197  38.592 -3.577 2.380  3.362  H8   N22 24 
N22 H8A  H8A  H 0 1 N N N 28.030 6.980  37.395 -4.448 0.872  2.997  H8A  N22 25 
N22 H8B  H8B  H 0 1 N N N 28.818 5.414  37.003 -2.668 0.896  2.987  H8B  N22 26 
N22 H7   H7   H 0 1 N N N 29.867 8.171  36.737 -4.480 2.411  1.053  H7   N22 27 
N22 H7A  H7A  H 0 1 N N N 30.980 7.135  37.621 -2.700 2.435  1.043  H7A  N22 28 
N22 HN8  HN8  H 0 1 N N N 33.383 3.966  33.773 -6.748 -1.256 -0.714 HN8  N22 29 
N22 HN8A HN8A H 0 0 N N N 33.730 4.626  35.226 -5.937 -2.480 -1.531 HN8A N22 30 
N22 HN7  HN7  H 0 1 N N N 28.636 5.875  32.170 -1.274 -2.592 -1.672 HN7  N22 31 
N22 HN7A HN7A H 0 0 N N N 29.909 6.690  31.553 -0.375 -1.401 -0.901 HN7A N22 32 
N22 H11  H11  H 0 1 N N N 26.979 9.799  33.118 1.254  2.712  0.689  H11  N22 33 
N22 H11A H11A H 0 0 N N N 25.814 8.484  33.552 1.284  1.733  2.176  H11A N22 34 
N22 H18  H18  H 0 1 N N N 27.742 11.514 35.174 2.604  -0.254 2.317  H18  N22 35 
N22 H4   H4   H 0 1 N N N 27.293 13.691 35.939 6.030  -3.260 1.670  H4   N22 36 
N22 H4A  H4A  H 0 1 N N N 27.822 14.402 37.501 5.270  -3.062 0.073  H4A  N22 37 
N22 H4B  H4B  H 0 1 N N N 28.685 12.979 36.824 6.440  -1.854 0.658  H4B  N22 38 
N22 H16  H16  H 0 1 N N N 24.989 11.100 38.491 5.220  -1.220 -0.920 H16  N22 39 
N22 H15  H15  H 0 1 N N N 24.032 8.997  37.561 4.138  0.500  -2.308 H15  N22 40 
N22 H2   H2   H 0 1 N N N 24.092 6.921  36.685 3.703  2.471  -2.847 H2   N22 41 
N22 H2A  H2A  H 0 1 N N N 22.926 7.620  35.511 2.533  1.260  -3.424 H2A  N22 42 
N22 H2B  H2B  H 0 1 N N N 23.951 6.223  35.036 2.084  2.981  -3.381 H2B  N22 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 
N22 C8  C7   SING N N 1  
N22 C7  C5   SING N N 2  
N22 C5  N4   DOUB N N 3  
N22 C5  C6   SING N N 4  
N22 N4  C3   SING N N 5  
N22 C3  N8   SING N N 6  
N22 C3  N2   DOUB N N 7  
N22 N2  C1   SING Y N 8  
N22 C1  N7   SING Y N 9  
N22 C1  C6   DOUB Y N 10 
N22 C6  C9   SING N N 11 
N22 C9  C10  TRIP Y N 12 
N22 C10 C11  SING N N 13 
N22 C11 C13  SING N N 14 
N22 C13 C18  DOUB Y N 15 
N22 C13 C14  SING N N 16 
N22 C18 C17  SING Y N 17 
N22 C17 O2   SING N N 18 
N22 C17 C16  DOUB N N 19 
N22 O2  C4   SING N N 20 
N22 C16 C15  SING N N 21 
N22 C15 C14  DOUB N N 22 
N22 C14 O10  SING N N 23 
N22 O10 C2   SING N N 24 
N22 C8  H8   SING N N 25 
N22 C8  H8A  SING Y N 26 
N22 C8  H8B  SING Y N 27 
N22 C7  H7   SING Y N 28 
N22 C7  H7A  SING N N 29 
N22 N8  HN8  SING N N 30 
N22 N8  HN8A SING Y N 31 
N22 N7  HN7  SING N N 32 
N22 N7  HN7A SING N N 33 
N22 C11 H11  SING N N 34 
N22 C11 H11A SING N N 35 
N22 C18 H18  SING Y N 36 
N22 C4  H4   SING N N 37 
N22 C4  H4A  SING Y N 38 
N22 C4  H4B  SING N N 39 
N22 C16 H16  SING N N 40 
N22 C15 H15  SING N N 41 
N22 C2  H2   SING N N 42 
N22 C2  H2A  SING N N 43 
N22 C2  H2B  SING N N 44 
# 
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 
N22 SMILES           ACDLabs              10.04 n2c(c(C#CCc1cc(OC)ccc1OC)c(nc2N)N)CC                                                                                                 
N22 InChI            InChI                1.02b InChI=1/C17H20N4O2/c1-4-14-13(16(18)21-17(19)20-14)7-5-6-11-10-12(22-2)8-9-15(11)23-3/h8-10H,4,6H2,1-3H3,(H4,18,19,20,21)/f/h18-19H2 
N22 InChIKey         InChI                1.02b NNFDQABYXZBKRK-SHHGZXMVCR                                                                                                            
N22 SMILES_CANONICAL CACTVS               3.341 CCc1nc(N)nc(N)c1C#CCc2cc(OC)ccc2OC                                                                                                   
N22 SMILES           CACTVS               3.341 CCc1nc(N)nc(N)c1C#CCc2cc(OC)ccc2OC                                                                                                   
N22 SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 CCc1c(c(nc(n1)N)N)C#CCc2cc(ccc2OC)OC                                                                                                 
N22 SMILES           "OpenEye OEToolkits" 1.5.0 CCc1c(c(nc(n1)N)N)C#CCc2cc(ccc2OC)OC                                                                                                 
# 
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 
N22 "SYSTEMATIC NAME" ACDLabs              10.04 5-[3-(2,5-dimethoxyphenyl)prop-1-yn-1-yl]-6-ethylpyrimidine-2,4-diamine 
N22 "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 5-[3-(2,5-dimethoxyphenyl)prop-1-ynyl]-6-ethyl-pyrimidine-2,4-diamine   
# 
