data_228
# 
_chem_comp.id                                    228 
_chem_comp.name                                  N-[2-(1,3-BENZODIOXOL-5-YL)ETHYL]-1-[2-(1H-IMIDAZOL-1-YL)-6-METHYLPYRIMIDIN-4-YL]-D-PROLINAMIDE 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C22 H24 N6 O3" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         ? 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2007-02-14 
_chem_comp.pdbx_modified_date                    2008-10-14 
_chem_comp.pdbx_ambiguous_flag                   ? 
_chem_comp.pdbx_release_status                   REL 
_chem_comp.pdbx_replaced_by                      ? 
_chem_comp.pdbx_replaces                         ? 
_chem_comp.formula_weight                        420.464 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     228 
_chem_comp.pdbx_model_coordinates_details        ? 
_chem_comp.pdbx_model_coordinates_missing_flag   N 
_chem_comp.pdbx_ideal_coordinates_details        "OpenEye/OEToolkits V1.4.2" 
_chem_comp.pdbx_ideal_coordinates_missing_flag   N 
_chem_comp.pdbx_model_coordinates_db_code        ? 
_chem_comp.pdbx_subcomponent_list                ? 
_chem_comp.pdbx_processing_site                  PDBJ 
# 
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 
228 C28  C28  C 0 1 Y N N 70.539 -4.547  50.720 -4.219 1.925  -0.800 C28  228 1  
228 C27  C27  C 0 1 Y N N 69.674 -4.575  51.829 -5.385 2.114  -1.512 C27  228 2  
228 O31  O31  O 0 1 N N N 68.558 -5.305  52.070 -6.614 2.358  -0.981 O31  228 3  
228 C30  C30  C 0 1 N N N 67.958 -4.745  53.246 -7.415 2.463  -2.176 C30  228 4  
228 O29  O29  O 0 1 N N N 68.966 -3.946  53.874 -6.656 2.281  -3.390 O29  228 5  
228 C26  C26  C 0 1 Y N N 69.941 -3.764  52.944 -5.409 2.071  -2.888 C26  228 6  
228 C25  C25  C 0 1 Y N N 71.076 -2.933  52.947 -4.268 1.835  -3.627 C25  228 7  
228 C24  C24  C 0 1 Y N N 71.938 -2.908  51.839 -3.073 1.641  -2.930 C24  228 8  
228 C23  C23  C 0 1 Y N N 71.668 -3.714  50.722 -3.063 1.687  -1.533 C23  228 9  
228 C22  C22  C 0 1 N N N 72.573 -3.641  49.486 -1.760 1.474  -0.802 C22  228 10 
228 C21  C21  C 0 1 N N N 73.919 -4.347  49.705 -1.499 0.007  -0.466 C21  228 11 
228 N20  N20  N 0 1 N N N 73.732 -5.806  49.817 -0.262 -0.185 0.257  N20  228 12 
228 C18  C18  C 0 1 N N N 74.008 -6.637  48.805 0.949  -0.415 -0.367 C18  228 13 
228 O19  O19  O 0 1 N N N 74.425 -6.274  47.705 1.144  -0.486 -1.575 O19  228 14 
228 C17  C17  C 0 1 N N R 73.764 -8.128  49.088 2.099  -0.582 0.577  C17  228 15 
228 C16  C16  C 0 1 N N N 75.025 -8.717  49.729 2.302  -2.062 0.910  C16  228 16 
228 C15  C15  C 0 1 N N N 74.444 -9.809  50.606 3.240  -2.549 -0.184 C15  228 17 
228 C14  C14  C 0 1 N N N 73.312 -9.044  51.280 4.168  -1.358 -0.409 C14  228 18 
228 N13  N13  N 0 1 N N N 72.708 -8.357  50.119 3.344  -0.193 -0.086 N13  228 19 
228 C1   C1   C 0 1 Y N N 71.377 -8.180  49.978 3.773  1.109  -0.254 C1   228 20 
228 N1   N1   N 0 1 Y N N 70.583 -8.446  51.033 2.955  2.167  0.066  N1   228 21 
228 C6   C6   C 0 1 Y N N 70.790 -7.740  48.774 5.062  1.348  -0.759 C6   228 22 
228 C5   C5   C 0 1 Y N N 69.397 -7.598  48.727 5.454  2.662  -0.913 C5   228 23 
228 C12  C12  C 0 1 N N N 68.710 -7.092  47.461 6.815  2.965  -1.445 C12  228 24 
228 N4   N4   N 0 1 Y N N 68.654 -7.884  49.816 4.672  3.718  -0.608 N4   228 25 
228 C3   C3   C 0 1 Y N N 69.240 -8.304  50.963 3.453  3.403  -0.130 C3   228 26 
228 N7   N7   N 0 1 Y N N 68.511 -8.530  52.051 2.621  4.466  0.196  N7   228 27 
228 C8   C8   C 0 1 Y N N 67.184 -8.462  52.149 1.350  4.379  0.694  C8   228 28 
228 C9   C9   C 0 1 Y N N 66.856 -8.765  53.398 0.941  5.682  0.854  C9   228 29 
228 NFE  NFE  N 0 1 Y N N 67.981 -9.019  54.073 1.924  6.560  0.469  NFE  228 30 
228 C11  C11  C 0 1 Y N N 68.994 -8.878  53.237 2.921  5.797  0.079  C11  228 31 
228 H28  H28  H 0 1 N N N 70.333 -5.170  49.862 -4.213 1.962  0.284  H28  228 32 
228 H301 1H30 H 0 0 N N N 67.088 -4.127  52.978 -7.881 3.454  -2.200 H301 228 33 
228 H302 2H30 H 0 0 N N N 67.599 -5.534  53.923 -8.204 1.703  -2.139 H302 228 34 
228 H25  H25  H 0 1 N N N 71.285 -2.312  53.805 -4.291 1.801  -4.710 H25  228 35 
228 H24  H24  H 0 1 N N N 72.809 -2.269  51.846 -2.158 1.453  -3.486 H24  228 36 
228 H221 1H22 H 0 0 N N N 72.767 -2.583  49.257 -1.780 2.060  0.125  H221 228 37 
228 H222 2H22 H 0 0 N N N 72.056 -4.149  48.659 -0.931 1.878  -1.396 H222 228 38 
228 H211 1H21 H 0 0 N N N 74.579 -4.134  48.851 -2.301 -0.377 0.173  H211 228 39 
228 H212 2H21 H 0 0 N N N 74.366 -3.975  50.639 -1.455 -0.612 -1.368 H212 228 40 
228 HN20 HN20 H 0 0 N N N 73.388 -6.186  50.676 -0.285 -0.149 1.271  HN20 228 41 
228 H17  H17  H 0 1 N N N 73.478 -8.578  48.126 1.904  0.005  1.480  H17  228 42 
228 H161 1H16 H 0 0 N N N 75.724 -9.116  48.979 1.371  -2.637 0.942  H161 228 43 
228 H162 2H16 H 0 0 N N N 75.628 -7.980  50.280 2.798  -2.157 1.884  H162 228 44 
228 H151 1H15 H 0 0 N N N 74.085 -10.672 50.026 3.785  -3.455 0.095  H151 228 45 
228 H152 2H15 H 0 0 N N N 75.163 -10.268 51.301 2.673  -2.761 -1.099 H152 228 46 
228 H141 1H14 H 0 0 N N N 73.677 -8.339  52.041 5.025  -1.405 0.271  H141 228 47 
228 H142 2H14 H 0 0 N N N 72.612 -9.678  51.843 4.533  -1.328 -1.441 H142 228 48 
228 H6   H6   H 0 1 N N N 71.399 -7.518  47.910 5.715  0.521  -1.013 H6   228 49 
228 H121 1H12 H 0 0 N N N 67.633 -6.970  47.651 7.205  3.884  -0.992 H121 228 50 
228 H122 2H12 H 0 0 N N N 69.143 -6.123  47.171 7.516  2.147  -1.234 H122 228 51 
228 H123 3H12 H 0 0 N N N 68.859 -7.818  46.648 6.796  3.094  -2.535 H123 228 52 
228 H8   H8   H 0 1 N N N 66.499 -8.206  51.354 0.860  3.434  0.887  H8   228 53 
228 H9   H9   H 0 1 N N N 65.854 -8.800  53.800 -0.010 6.033  1.226  H9   228 54 
228 H11  H11  H 0 1 N N N 70.037 -9.021  53.478 3.873  6.150  -0.295 H11  228 55 
# 
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 
228 C28 C23  DOUB Y N 1  
228 C28 C27  SING Y N 2  
228 C28 H28  SING N N 3  
228 C27 O31  SING N N 4  
228 C27 C26  DOUB Y N 5  
228 O31 C30  SING N N 6  
228 C30 O29  SING N N 7  
228 C30 H301 SING N N 8  
228 C30 H302 SING N N 9  
228 O29 C26  SING N N 10 
228 C26 C25  SING Y N 11 
228 C25 C24  DOUB Y N 12 
228 C25 H25  SING N N 13 
228 C24 C23  SING Y N 14 
228 C24 H24  SING N N 15 
228 C23 C22  SING N N 16 
228 C22 C21  SING N N 17 
228 C22 H221 SING N N 18 
228 C22 H222 SING N N 19 
228 C21 N20  SING N N 20 
228 C21 H211 SING N N 21 
228 C21 H212 SING N N 22 
228 N20 C18  SING N N 23 
228 N20 HN20 SING N N 24 
228 C18 O19  DOUB N N 25 
228 C18 C17  SING N N 26 
228 C17 C16  SING N N 27 
228 C17 N13  SING N N 28 
228 C17 H17  SING N N 29 
228 C16 C15  SING N N 30 
228 C16 H161 SING N N 31 
228 C16 H162 SING N N 32 
228 C15 C14  SING N N 33 
228 C15 H151 SING N N 34 
228 C15 H152 SING N N 35 
228 C14 N13  SING N N 36 
228 C14 H141 SING N N 37 
228 C14 H142 SING N N 38 
228 N13 C1   SING N N 39 
228 C1  C6   SING Y N 40 
228 C1  N1   DOUB Y N 41 
228 N1  C3   SING Y N 42 
228 C6  C5   DOUB Y N 43 
228 C6  H6   SING N N 44 
228 C5  C12  SING N N 45 
228 C5  N4   SING Y N 46 
228 C12 H121 SING N N 47 
228 C12 H122 SING N N 48 
228 C12 H123 SING N N 49 
228 N4  C3   DOUB Y N 50 
228 C3  N7   SING N N 51 
228 N7  C8   SING Y N 52 
228 N7  C11  SING Y N 53 
228 C8  C9   DOUB Y N 54 
228 C8  H8   SING N N 55 
228 C9  NFE  SING Y N 56 
228 C9  H9   SING N N 57 
228 NFE C11  DOUB Y N 58 
228 C11 H11  SING N N 59 
# 
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 
228 SMILES           ACDLabs              10.04 O=C(NCCc1ccc2OCOc2c1)C5N(c3nc(nc(c3)C)n4ccnc4)CCC5                                                                                                                                     
228 InChI            InChI                1.02b InChI=1/C22H24N6O3/c1-15-11-20(26-22(25-15)27-10-8-23-13-27)28-9-2-3-17(28)21(29)24-7-6-16-4-5-18-19(12-16)31-14-30-18/h4-5,8,10-13,17H,2-3,6-7,9,14H2,1H3,(H,24,29)/t17-/m1/s1/f/h24H 
228 InChIKey         InChI                1.02b LBCGUKCXRVUULK-UWJLXQJCDK                                                                                                                                                              
228 SMILES_CANONICAL CACTVS               3.341 Cc1cc(nc(n1)n2ccnc2)N3CCC[C@@H]3C(=O)NCCc4ccc5OCOc5c4                                                                                                                                  
228 SMILES           CACTVS               3.341 Cc1cc(nc(n1)n2ccnc2)N3CCC[CH]3C(=O)NCCc4ccc5OCOc5c4                                                                                                                                    
228 SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 Cc1cc(nc(n1)n2ccnc2)N3CCC[C@@H]3C(=O)NCCc4ccc5c(c4)OCO5                                                                                                                                
228 SMILES           "OpenEye OEToolkits" 1.5.0 Cc1cc(nc(n1)n2ccnc2)N3CCCC3C(=O)NCCc4ccc5c(c4)OCO5                                                                                                                                     
# 
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 
228 "SYSTEMATIC NAME" ACDLabs              10.04 N-[2-(1,3-benzodioxol-5-yl)ethyl]-1-[2-(1H-imidazol-1-yl)-6-methylpyrimidin-4-yl]-D-prolinamide             
228 "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 (2R)-N-[2-(1,3-benzodioxol-5-yl)ethyl]-1-(2-imidazol-1-yl-6-methyl-pyrimidin-4-yl)pyrrolidine-2-carboxamide 
# 
