data_PPB
# 
_chem_comp.id                                    PPB 
_chem_comp.name                                  "1-{[1-(2-AMINO-3-PHENYL-PROPIONYL)-PYRROLIDINE-2-CARBONYL]-AMINO}-2-(3-CYANO-PHENYL)-ETHANEBORONIC ACID" 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C23 H27 B N4 O4" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         (D)PHE-PRO-BOROPHE(M-CN) 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     1999-07-08 
_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                        434.296 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     PPB 
_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        1AUJ 
_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 
PPB C3   C3   C 0 1 N N N 28.688 14.344 20.059 -0.061 -1.453 -3.800 C3   PPB 1  
PPB C4   C4   C 0 1 Y N N 29.130 14.032 18.618 0.727  -0.889 -4.954 C4   PPB 2  
PPB N1   N1   N 0 1 N N N 27.216 12.443 20.326 -0.943 -0.945 -1.576 N1   PPB 3  
PPB B1   B1   B 0 1 N N N 28.018 13.488 22.326 -0.910 0.870  -3.263 B1   PPB 4  
PPB C2   C2   C 0 1 N N R 28.364 13.117 20.921 -0.177 -0.398 -2.698 C2   PPB 5  
PPB O2   O2   O 0 1 N N N 29.265 13.850 23.004 -2.231 0.759  -3.772 O2   PPB 6  
PPB O1   O1   O 0 1 N N N 27.679 12.259 23.042 -0.252 2.128  -3.265 O1   PPB 7  
PPB N5   N5   N 0 1 N N N 26.027 9.657  18.557 -1.051 -0.469 2.095  N5   PPB 8  
PPB C7   C7   C 0 1 N N S 25.861 10.794 19.452 -1.484 -1.085 0.832  C7   PPB 9  
PPB C8   C8   C 0 1 N N N 27.200 11.159 19.993 -0.696 -0.522 -0.321 C8   PPB 10 
PPB O3   O3   O 0 1 N N N 28.068 10.307 20.221 0.160  0.312  -0.120 O3   PPB 11 
PPB C9   C9   C 0 1 N N N 25.054 10.236 20.624 -2.982 -0.759 0.654  C9   PPB 12 
PPB C10  C10  C 0 1 N N N 25.043 8.711  20.527 -3.447 -0.448 2.101  C10  PPB 13 
PPB C11  C11  C 0 1 N N N 25.717 8.372  19.185 -2.195 0.248  2.687  C11  PPB 14 
PPB C12  C12  C 0 1 N N N 26.430 9.905  17.298 0.187  -0.543 2.621  C12  PPB 15 
PPB O4   O4   O 0 1 N N N 27.002 10.955 16.985 1.054  -1.164 2.044  O4   PPB 16 
PPB C14  C14  C 0 1 N N R 26.504 8.656  16.401 0.494  0.145  3.925  C14  PPB 17 
PPB C16  C16  C 0 1 Y N N 29.598 12.775 18.193 0.075  -0.233 -5.977 C16  PPB 18 
PPB C23  C23  C 0 1 Y N N 30.098 12.631 16.891 0.808  0.292  -7.044 C23  PPB 19 
PPB C24  C24  C 0 1 Y N N 29.155 15.116 17.709 2.102  -1.037 -4.988 C24  PPB 20 
PPB C25  C25  C 0 1 Y N N 29.674 14.977 16.401 2.834  -0.523 -6.044 C25  PPB 21 
PPB C5   C5   C 0 1 Y N N 30.148 13.724 16.014 2.195  0.140  -7.071 C5   PPB 22 
PPB C6   C6   C 0 1 N N N 30.541 11.293 16.344 0.138  0.980  -8.107 C6   PPB 23 
PPB N2   N2   N 0 1 N N N 30.900 10.240 15.895 -0.392 1.525  -8.950 N2   PPB 24 
PPB C13  C13  C 0 1 N N N 25.505 8.587  15.237 0.222  -0.814 5.085  C13  PPB 25 
PPB N6   N6   N 0 1 N N N 27.860 8.557  15.869 1.906  0.549  3.945  N6   PPB 26 
PPB C17  C17  C 0 1 Y N N 22.272 6.972  16.713 2.081  0.428  8.127  C17  PPB 27 
PPB C18  C18  C 0 1 Y N N 21.300 7.480  15.813 1.092  1.136  8.784  C18  PPB 28 
PPB C19  C19  C 0 1 Y N N 21.647 8.391  14.806 -0.177 1.213  8.244  C19  PPB 29 
PPB C20  C20  C 0 1 Y N N 23.006 8.786  14.703 -0.459 0.581  7.048  C20  PPB 30 
PPB C21  C21  C 0 1 Y N N 24.022 8.285  15.568 0.529  -0.126 6.390  C21  PPB 31 
PPB C22  C22  C 0 1 Y N N 23.626 7.379  16.593 1.798  -0.206 6.932  C22  PPB 32 
PPB H31  1H3  H 0 1 N N N 29.451 14.978 20.566 0.447  -2.333 -3.408 H31  PPB 33 
PPB H32  2H3  H 0 1 N N N 27.823 15.047 20.051 -1.057 -1.731 -4.143 H32  PPB 34 
PPB HN1  HN1  H 0 1 N N N 26.336 12.917 20.122 -1.628 -1.613 -1.737 HN1  PPB 35 
PPB H2   H2   H 0 1 N N N 29.266 12.462 20.953 0.819  -0.119 -2.356 H2   PPB 36 
PPB HO2  HO2  H 0 1 N N N 29.045 14.085 23.897 -2.493 1.642  -4.065 HO2  PPB 37 
PPB HO1  HO1  H 0 1 N N N 27.459 12.494 23.935 0.624  1.986  -2.882 HO1  PPB 38 
PPB H7   H7   H 0 1 N N N 25.389 11.670 18.950 -1.344 -2.165 0.885  H7   PPB 39 
PPB H91  1H9  H 0 1 N N N 25.426 10.598 21.610 -3.521 -1.617 0.251  H91  PPB 40 
PPB H92  2H9  H 0 1 N N N 24.027 10.667 20.679 -3.110 0.112  0.012  H92  PPB 41 
PPB H101 1H10 H 0 0 N N N 25.512 8.204  21.402 -3.674 -1.366 2.644  H101 PPB 42 
PPB H102 2H10 H 0 0 N N N 24.028 8.263  20.642 -4.305 0.224  2.100  H102 PPB 43 
PPB H111 1H11 H 0 0 N N N 25.109 7.695  18.539 -2.181 0.153  3.773  H111 PPB 44 
PPB H112 2H11 H 0 0 N N N 26.601 7.701  19.287 -2.175 1.298  2.397  H112 PPB 45 
PPB H14  H14  H 0 1 N N N 26.222 7.802  17.060 -0.137 1.027  4.028  H14  PPB 46 
PPB H16  H16  H 0 1 N N N 29.573 11.908 18.875 -0.998 -0.118 -5.950 H16  PPB 47 
PPB H24  H24  H 0 1 N N N 28.759 16.094 18.028 2.607  -1.555 -4.186 H24  PPB 48 
PPB H25  H25  H 0 1 N N N 29.708 15.826 15.698 3.907  -0.641 -6.064 H25  PPB 49 
PPB H5   H5   H 0 1 N N N 30.567 13.595 15.002 2.767  0.541  -7.895 H5   PPB 50 
PPB H131 1H13 H 0 0 N N N 25.562 9.532  14.649 -0.825 -1.114 5.070  H131 PPB 51 
PPB H132 2H13 H 0 0 N N N 25.869 7.847  14.485 0.853  -1.697 4.982  H132 PPB 52 
PPB HN61 1HN6 H 0 0 N N N 27.909 7.729  15.274 2.450  -0.294 3.848  HN61 PPB 53 
PPB HN62 2HN6 H 0 0 N N N 28.570 8.558  16.600 2.064  1.093  3.111  HN62 PPB 54 
PPB H17  H17  H 0 1 N N N 21.975 6.262  17.503 3.073  0.369  8.548  H17  PPB 55 
PPB H18  H18  H 0 1 N N N 20.248 7.158  15.898 1.312  1.630  9.719  H18  PPB 56 
PPB H19  H19  H 0 1 N N N 20.878 8.783  14.119 -0.950 1.766  8.758  H19  PPB 57 
PPB H20  H20  H 0 1 N N N 23.283 9.511  13.919 -1.452 0.641  6.626  H20  PPB 58 
PPB H22  H22  H 0 1 N N N 24.375 6.988  17.301 2.570  -0.760 6.419  H22  PPB 59 
# 
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 
PPB C3  C4   SING N N 1  
PPB C3  C2   SING N N 2  
PPB C3  H31  SING N N 3  
PPB C3  H32  SING N N 4  
PPB C4  C16  DOUB Y N 5  
PPB C4  C24  SING Y N 6  
PPB N1  C2   SING N N 7  
PPB N1  C8   SING N N 8  
PPB N1  HN1  SING N N 9  
PPB B1  C2   SING N N 10 
PPB B1  O2   SING N N 11 
PPB B1  O1   SING N N 12 
PPB C2  H2   SING N N 13 
PPB O2  HO2  SING N N 14 
PPB O1  HO1  SING N N 15 
PPB N5  C7   SING N N 16 
PPB N5  C11  SING N N 17 
PPB N5  C12  SING N N 18 
PPB C7  C8   SING N N 19 
PPB C7  C9   SING N N 20 
PPB C7  H7   SING N N 21 
PPB C8  O3   DOUB N N 22 
PPB C9  C10  SING N N 23 
PPB C9  H91  SING N N 24 
PPB C9  H92  SING N N 25 
PPB C10 C11  SING N N 26 
PPB C10 H101 SING N N 27 
PPB C10 H102 SING N N 28 
PPB C11 H111 SING N N 29 
PPB C11 H112 SING N N 30 
PPB C12 O4   DOUB N N 31 
PPB C12 C14  SING N N 32 
PPB C14 C13  SING N N 33 
PPB C14 N6   SING N N 34 
PPB C14 H14  SING N N 35 
PPB C16 C23  SING Y N 36 
PPB C16 H16  SING N N 37 
PPB C23 C5   DOUB Y N 38 
PPB C23 C6   SING N N 39 
PPB C24 C25  DOUB Y N 40 
PPB C24 H24  SING N N 41 
PPB C25 C5   SING Y N 42 
PPB C25 H25  SING N N 43 
PPB C5  H5   SING N N 44 
PPB C6  N2   TRIP N N 45 
PPB C13 C21  SING N N 46 
PPB C13 H131 SING N N 47 
PPB C13 H132 SING N N 48 
PPB N6  HN61 SING N N 49 
PPB N6  HN62 SING N N 50 
PPB C17 C18  DOUB Y N 51 
PPB C17 C22  SING Y N 52 
PPB C17 H17  SING N N 53 
PPB C18 C19  SING Y N 54 
PPB C18 H18  SING N N 55 
PPB C19 C20  DOUB Y N 56 
PPB C19 H19  SING N N 57 
PPB C20 C21  SING Y N 58 
PPB C20 H20  SING N N 59 
PPB C21 C22  DOUB Y N 60 
PPB C22 H22  SING N N 61 
# 
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 
PPB SMILES           ACDLabs              10.04 O=C(NC(B(O)O)Cc1cccc(C#N)c1)C3N(C(=O)C(N)Cc2ccccc2)CCC3                                                                                                                                              
PPB InChI            InChI                1.02b InChI=1/C23H27BN4O4/c25-15-18-9-4-8-17(12-18)14-21(24(31)32)27-22(29)20-10-5-11-28(20)23(30)19(26)13-16-6-2-1-3-7-16/h1-4,6-9,12,19-21,31-32H,5,10-11,13-14,26H2,(H,27,29)/t19-,20+,21+/m1/s1/f/h27H 
PPB InChIKey         InChI                1.02b UFOIPTZMXQILSG-ZTMILXHDDA                                                                                                                                                                            
PPB SMILES_CANONICAL CACTVS               3.341 N[C@H](Cc1ccccc1)C(=O)N2CCC[C@H]2C(=O)N[C@@H](Cc3cccc(c3)C#N)B(O)O                                                                                                                                   
PPB SMILES           CACTVS               3.341 N[CH](Cc1ccccc1)C(=O)N2CCC[CH]2C(=O)N[CH](Cc3cccc(c3)C#N)B(O)O                                                                                                                                       
PPB SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 B([C@H](Cc1cccc(c1)C#N)NC(=O)[C@@H]2CCCN2C(=O)[C@@H](Cc3ccccc3)N)(O)O                                                                                                                                
PPB SMILES           "OpenEye OEToolkits" 1.5.0 B(C(Cc1cccc(c1)C#N)NC(=O)C2CCCN2C(=O)C(Cc3ccccc3)N)(O)O                                                                                                                                              
# 
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 
PPB "SYSTEMATIC NAME" ACDLabs              10.04 D-phenylalanyl-N-[(1R)-2-(3-cyanophenyl)-1-(dihydroxyboranyl)ethyl]-L-prolinamide                                      
PPB "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "[(1R)-1-[[(2S)-1-[(2R)-2-amino-3-phenyl-propanoyl]pyrrolidin-2-yl]carbonylamino]-2-(3-cyanophenyl)ethyl]boronic acid" 
# 
