data_LPR
# 
_chem_comp.id                                    LPR 
_chem_comp.name                                  [N2-[(S)-1-CARBOXY-3-PHENYLPROPYL]-L-LYSYL-L-PROLINE 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C21 H31 N3 O5" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         LISINOPRIL 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2002-11-25 
_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                        405.488 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     LPR 
_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        1O86 
_chem_comp.pdbx_subcomponent_list                ? 
_chem_comp.pdbx_processing_site                  EBI 
# 
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 
LPR O1   O1   O 0 1 N N N 40.291 33.743 45.120 -1.345 -0.983 -0.207 O1   LPR 1  
LPR O2   O2   O 0 1 N N N 43.369 36.201 48.269 3.275  1.701  0.120  O2   LPR 2  
LPR O3   O3   O 0 1 N N N 41.939 37.283 47.069 1.854  3.300  0.674  O3   LPR 3  
LPR O4   O4   O 0 1 N N N 38.843 33.368 41.867 -5.020 -1.510 -2.018 O4   LPR 4  
LPR O5   O5   O 0 1 N N N 40.703 32.272 42.326 -2.866 -1.899 -2.317 O5   LPR 5  
LPR N1   N1   N 0 1 N N N 41.897 34.063 47.266 1.176  -0.083 0.059  N1   LPR 6  
LPR N2   N2   N 0 1 N N N 41.810 34.533 43.599 -1.931 0.504  -1.745 N2   LPR 7  
LPR N3   N3   N 0 1 N N N 43.329 27.774 44.087 5.139  -1.793 -4.848 N3   LPR 8  
LPR C1   C1   C 0 1 N N N 41.502 34.052 44.840 -1.003 -0.143 -1.013 C1   LPR 9  
LPR C2   C2   C 0 1 N N S 42.612 33.852 45.943 0.458  0.173  -1.196 C2   LPR 10 
LPR C3   C3   C 0 1 N N N 42.259 36.267 47.654 2.076  2.118  0.555  C3   LPR 11 
LPR C4   C4   C 0 1 N N S 41.315 35.065 47.682 1.006  1.113  0.894  C4   LPR 12 
LPR C5   C5   C 0 1 N N S 40.715 34.685 42.559 -3.384 0.303  -1.659 C5   LPR 13 
LPR C6   C6   C 0 1 N N N 41.505 35.237 41.353 -4.042 1.279  -2.658 C6   LPR 14 
LPR C7   C7   C 0 1 N N N 42.826 35.369 41.680 -2.954 2.369  -2.849 C7   LPR 15 
LPR C8   C8   C 0 1 N N N 43.138 34.956 43.062 -1.655 1.529  -2.768 C8   LPR 16 
LPR C9   C9   C 0 1 N N N 40.081 33.284 42.224 -3.737 -1.116 -2.022 C9   LPR 17 
LPR C10  C10  C 0 1 N N N 43.252 32.473 45.784 1.036  -0.708 -2.304 C10  LPR 18 
LPR C11  C11  C 0 1 N N N 42.484 31.248 45.536 2.520  -0.386 -2.490 C11  LPR 19 
LPR C12  C12  C 0 1 N N N 43.296 30.062 44.842 3.099  -1.268 -3.598 C12  LPR 20 
LPR C13  C13  C 0 1 N N N 42.487 28.895 44.629 4.583  -0.946 -3.784 C13  LPR 21 
LPR C14  C14  C 0 1 N N N 40.586 35.365 48.932 1.121  0.724  2.370  C14  LPR 22 
LPR C15  C15  C 0 1 N N N 39.408 36.299 49.163 -0.055 -0.174 2.754  C15  LPR 23 
LPR C16  C16  C 0 1 Y N N 38.847 36.401 50.549 -0.022 -0.439 4.237  C16  LPR 24 
LPR C17  C17  C 0 1 Y N N 38.566 35.206 51.331 -0.684 0.406  5.106  C17  LPR 25 
LPR C18  C18  C 0 1 Y N N 38.016 35.319 52.656 -0.654 0.163  6.466  C18  LPR 26 
LPR C19  C19  C 0 1 Y N N 37.737 36.627 53.218 0.039  -0.927 6.957  C19  LPR 27 
LPR C20  C20  C 0 1 Y N N 38.014 37.822 52.443 0.701  -1.774 6.088  C20  LPR 28 
LPR C21  C21  C 0 1 Y N N 38.568 37.710 51.112 0.666  -1.533 4.728  C21  LPR 29 
LPR H2   H2   H 0 1 N N N 43.619 35.406 48.726 3.962  2.347  -0.097 H2   LPR 30 
LPR H4   H4   H 0 1 N N N 38.347 34.174 41.785 -5.247 -2.421 -2.250 H4   LPR 31 
LPR H1   H1   H 0 1 N N N 41.181 33.323 47.291 0.687  -0.833 0.524  H1   LPR 32 
LPR H3N1 1H3N H 0 0 N N N 42.717 27.028 43.726 6.113  -1.547 -4.935 H3N1 LPR 33 
LPR H3N2 2H3N H 0 0 N N N 43.924 28.129 43.325 5.108  -2.742 -4.508 H3N2 LPR 34 
LPR HA   HA   H 0 1 N N N 43.451 34.559 45.868 0.570  1.222  -1.471 HA   LPR 35 
LPR HB   HB   H 0 1 N N N 40.486 34.821 47.002 0.025  1.549  0.709  HB   LPR 36 
LPR H5   H5   H 0 1 N N N 39.876 35.324 42.871 -3.725 0.522  -0.647 H5   LPR 37 
LPR H6   H6   H 0 1 N N N 41.084 35.479 40.409 -4.950 1.710  -2.238 H6   LPR 38 
LPR H62  2H6  H 0 1 N N N 41.071 36.190 40.970 -4.253 0.775  -3.601 H62  LPR 39 
LPR H7   H7   H 0 1 N N N 43.558 35.734 41.004 -2.994 3.105  -2.046 H7   LPR 40 
LPR H72  2H7  H 0 1 N N N 43.176 36.410 41.491 -3.049 2.849  -3.822 H72  LPR 41 
LPR H8C1 1H8C H 0 0 N N N 43.549 35.796 43.642 -0.817 2.155  -2.462 H8C1 LPR 42 
LPR H8C2 2H8C H 0 0 N N N 43.897 34.162 43.114 -1.447 1.059  -3.729 H8C2 LPR 43 
LPR H101 1H10 H 0 0 N N N 43.955 32.563 44.943 0.504  -0.517 -3.236 H101 LPR 44 
LPR H102 2H10 H 0 0 N N N 43.624 32.290 46.803 0.924  -1.757 -2.029 H102 LPR 45 
LPR H111 1H11 H 0 0 N N N 42.107 30.882 46.502 3.053  -0.576 -1.558 H111 LPR 46 
LPR H112 2H11 H 0 0 N N N 41.688 31.526 44.829 2.633  0.662  -2.765 H112 LPR 47 
LPR H121 1H12 H 0 0 N N N 44.145 29.790 45.487 2.566  -1.077 -4.530 H121 LPR 48 
LPR H122 2H12 H 0 0 N N N 43.635 30.419 43.858 2.987  -2.317 -3.323 H122 LPR 49 
LPR H131 1H13 H 0 0 N N N 41.689 29.132 43.909 5.116  -1.136 -2.852 H131 LPR 50 
LPR H132 2H13 H 0 0 N N N 42.046 28.583 45.587 4.695  0.102  -4.059 H132 LPR 51 
LPR H141 1H14 H 0 0 N N N 40.227 34.385 49.278 2.056  0.188  2.533  H141 LPR 52 
LPR H142 2H14 H 0 0 N N N 41.361 35.978 49.416 1.106  1.624  2.985  H142 LPR 53 
LPR H151 1H15 H 0 0 N N N 39.729 37.308 48.866 -0.991 0.321  2.494  H151 LPR 54 
LPR H152 2H15 H 0 0 N N N 38.592 35.861 48.570 0.016  -1.118 2.214  H152 LPR 55 
LPR H17  H17  H 0 1 N N N 38.768 34.247 50.922 -1.226 1.258  4.722  H17  LPR 56 
LPR H18  H18  H 0 1 N N N 37.814 34.444 53.223 -1.171 0.824  7.145  H18  LPR 57 
LPR H19  H19  H 0 1 N N N 37.331 36.710 54.195 0.063  -1.117 8.020  H19  LPR 58 
LPR H20  H20  H 0 1 N N N 37.810 38.779 52.854 1.242  -2.626 6.472  H20  LPR 59 
LPR H21  H21  H 0 1 N N N 38.771 38.585 50.546 1.183  -2.195 4.049  H21  LPR 60 
# 
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 
LPR O1  C1   DOUB N N 1  
LPR O2  C3   SING N N 2  
LPR O2  H2   SING N N 3  
LPR O3  C3   DOUB N N 4  
LPR O4  C9   SING N N 5  
LPR O4  H4   SING N N 6  
LPR O5  C9   DOUB N N 7  
LPR N1  C2   SING N N 8  
LPR N1  C4   SING N N 9  
LPR N1  H1   SING N N 10 
LPR N2  C1   SING N N 11 
LPR N2  C5   SING N N 12 
LPR N2  C8   SING N N 13 
LPR N3  C13  SING N N 14 
LPR N3  H3N1 SING N N 15 
LPR N3  H3N2 SING N N 16 
LPR C1  C2   SING N N 17 
LPR C2  C10  SING N N 18 
LPR C2  HA   SING N N 19 
LPR C3  C4   SING N N 20 
LPR C4  C14  SING N N 21 
LPR C4  HB   SING N N 22 
LPR C5  C6   SING N N 23 
LPR C5  C9   SING N N 24 
LPR C5  H5   SING N N 25 
LPR C6  C7   SING N N 26 
LPR C6  H6   SING N N 27 
LPR C6  H62  SING N N 28 
LPR C7  C8   SING N N 29 
LPR C7  H7   SING N N 30 
LPR C7  H72  SING N N 31 
LPR C8  H8C1 SING N N 32 
LPR C8  H8C2 SING N N 33 
LPR C10 C11  SING N N 34 
LPR C10 H101 SING N N 35 
LPR C10 H102 SING N N 36 
LPR C11 C12  SING N N 37 
LPR C11 H111 SING N N 38 
LPR C11 H112 SING N N 39 
LPR C12 C13  SING N N 40 
LPR C12 H121 SING N N 41 
LPR C12 H122 SING N N 42 
LPR C13 H131 SING N N 43 
LPR C13 H132 SING N N 44 
LPR C14 C15  SING N N 45 
LPR C14 H141 SING N N 46 
LPR C14 H142 SING N N 47 
LPR C15 C16  SING N N 48 
LPR C15 H151 SING N N 49 
LPR C15 H152 SING N N 50 
LPR C16 C17  DOUB Y N 51 
LPR C16 C21  SING Y N 52 
LPR C17 C18  SING Y N 53 
LPR C17 H17  SING N N 54 
LPR C18 C19  DOUB Y N 55 
LPR C18 H18  SING N N 56 
LPR C19 C20  SING Y N 57 
LPR C19 H19  SING N N 58 
LPR C20 C21  DOUB Y N 59 
LPR C20 H20  SING N N 60 
LPR C21 H21  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 
LPR SMILES           ACDLabs              10.04 O=C(O)C2N(C(=O)C(NC(C(=O)O)CCc1ccccc1)CCCCN)CCC2                                                                                                                                         
LPR InChI            InChI                1.02b InChI=1/C21H31N3O5/c22-13-5-4-9-16(19(25)24-14-6-10-18(24)21(28)29)23-17(20(26)27)12-11-15-7-2-1-3-8-15/h1-3,7-8,16-18,23H,4-6,9-14,22H2,(H,26,27)(H,28,29)/t16-,17-,18-/m0/s1/f/h26,28H 
LPR InChIKey         InChI                1.02b RLAWWYSOJDYHDC-YMXGEOMKDH                                                                                                                                                                
LPR SMILES_CANONICAL CACTVS               3.341 NCCCC[C@H](N[C@@H](CCc1ccccc1)C(O)=O)C(=O)N2CCC[C@H]2C(O)=O                                                                                                                              
LPR SMILES           CACTVS               3.341 NCCCC[CH](N[CH](CCc1ccccc1)C(O)=O)C(=O)N2CCC[CH]2C(O)=O                                                                                                                                  
LPR SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 c1ccc(cc1)CC[C@@H](C(=O)O)N[C@@H](CCCCN)C(=O)N2CCC[C@H]2C(=O)O                                                                                                                           
LPR SMILES           "OpenEye OEToolkits" 1.5.0 c1ccc(cc1)CCC(C(=O)O)NC(CCCCN)C(=O)N2CCCC2C(=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 
LPR "SYSTEMATIC NAME" ACDLabs              10.04 N~2~-[(1S)-1-carboxy-3-phenylpropyl]-L-lysyl-L-proline                                                           
LPR "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "(2S)-1-[(2S)-6-amino-2-[[(2S)-1-hydroxy-1-oxo-4-phenyl-butan-2-yl]amino]hexanoyl]pyrrolidine-2-carboxylic acid" 
# 
