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 2020-06-17 _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 "CLT LYS PRO" _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 O2 O2 O 0 1 N N N 43.369 36.201 48.269 3.275 1.701 0.120 OG1 CLT 1 LPR O3 O3 O 0 1 N N N 41.939 37.283 47.069 1.854 3.300 0.674 OG2 CLT 2 LPR C3 C3 C 0 1 N N N 42.259 36.267 47.654 2.076 2.118 0.555 CB2 CLT 3 LPR C4 C4 C 0 1 N N S 41.315 35.065 47.682 1.006 1.113 0.894 CA CLT 4 LPR C14 C14 C 0 1 N N N 40.586 35.365 48.932 1.121 0.724 2.370 CB1 CLT 5 LPR C15 C15 C 0 1 N N N 39.408 36.299 49.163 -0.055 -0.174 2.754 CG CLT 6 LPR C16 C16 C 0 1 Y N N 38.847 36.401 50.549 -0.022 -0.439 4.237 CD CLT 7 LPR C17 C17 C 0 1 Y N N 38.566 35.206 51.331 -0.684 0.406 5.106 CE1 CLT 8 LPR C18 C18 C 0 1 Y N N 38.016 35.319 52.656 -0.654 0.163 6.466 CZ1 CLT 9 LPR C19 C19 C 0 1 Y N N 37.737 36.627 53.218 0.039 -0.927 6.957 CH CLT 10 LPR C20 C20 C 0 1 Y N N 38.014 37.822 52.443 0.701 -1.774 6.088 CZ2 CLT 11 LPR C21 C21 C 0 1 Y N N 38.568 37.710 51.112 0.666 -1.533 4.728 CE2 CLT 12 LPR H2 H2 H 0 1 N N N 43.619 35.406 48.726 3.962 2.347 -0.097 HO2 CLT 13 LPR HB HB H 0 1 N N N 40.486 34.821 47.002 0.025 1.549 0.709 HA1 CLT 14 LPR H141 1H14 H 0 0 N N N 40.227 34.385 49.278 2.056 0.188 2.533 HB11 CLT 15 LPR H142 2H14 H 0 0 N N N 41.361 35.978 49.416 1.106 1.624 2.985 HB12 CLT 16 LPR H151 1H15 H 0 0 N N N 39.729 37.308 48.866 -0.991 0.321 2.494 HG1 CLT 17 LPR H152 2H15 H 0 0 N N N 38.592 35.861 48.570 0.016 -1.118 2.214 HG2 CLT 18 LPR H17 H17 H 0 1 N N N 38.768 34.247 50.922 -1.226 1.258 4.722 HE1 CLT 19 LPR H18 H18 H 0 1 N N N 37.814 34.444 53.223 -1.171 0.824 7.145 HZ1 CLT 20 LPR H19 H19 H 0 1 N N N 37.331 36.710 54.195 0.063 -1.117 8.020 HH CLT 21 LPR H20 H20 H 0 1 N N N 37.810 38.779 52.854 1.242 -2.626 6.472 HZ2 CLT 22 LPR H21 H21 H 0 1 N N N 38.771 38.585 50.546 1.183 -2.195 4.049 HE2 CLT 23 LPR N1 N1 N 0 1 N N N 41.897 34.063 47.266 1.176 -0.083 0.059 N LYS 24 LPR N3 N3 N 0 1 N N N 43.329 27.774 44.087 5.139 -1.793 -4.848 NZ LYS 25 LPR C1 C1 C 0 1 N N N 41.502 34.052 44.840 -1.003 -0.143 -1.013 C LYS 26 LPR C2 C2 C 0 1 N N S 42.612 33.852 45.943 0.458 0.173 -1.196 CA LYS 27 LPR O1 O1 O 0 1 N N N 40.291 33.743 45.120 -1.345 -0.983 -0.207 O LYS 28 LPR C10 C10 C 0 1 N N N 43.252 32.473 45.784 1.036 -0.708 -2.304 CB LYS 29 LPR C11 C11 C 0 1 N N N 42.484 31.248 45.536 2.520 -0.386 -2.490 CG LYS 30 LPR C12 C12 C 0 1 N N N 43.296 30.062 44.842 3.099 -1.268 -3.598 CD LYS 31 LPR C13 C13 C 0 1 N N N 42.487 28.895 44.629 4.583 -0.946 -3.784 CE LYS 32 LPR H1 H1 H 0 1 N N N 41.181 33.323 47.291 0.687 -0.833 0.524 H LYS 33 LPR H3N1 1H3N H 0 0 N N N 42.717 27.028 43.726 6.113 -1.547 -4.935 HZ1 LYS 34 LPR H3N2 2H3N H 0 0 N N N 43.924 28.129 43.325 5.108 -2.742 -4.508 HZ2 LYS 35 LPR HA HA H 0 1 N N N 43.451 34.559 45.868 0.570 1.222 -1.471 HA LYS 36 LPR H101 1H10 H 0 0 N N N 43.955 32.563 44.943 0.504 -0.517 -3.236 HB2 LYS 37 LPR H102 2H10 H 0 0 N N N 43.624 32.290 46.803 0.924 -1.757 -2.029 HB3 LYS 38 LPR H111 1H11 H 0 0 N N N 42.107 30.882 46.502 3.053 -0.576 -1.558 HG2 LYS 39 LPR H112 2H11 H 0 0 N N N 41.688 31.526 44.829 2.633 0.662 -2.765 HG3 LYS 40 LPR H121 1H12 H 0 0 N N N 44.145 29.790 45.487 2.566 -1.077 -4.530 HD2 LYS 41 LPR H122 2H12 H 0 0 N N N 43.635 30.419 43.858 2.987 -2.317 -3.323 HD3 LYS 42 LPR H131 1H13 H 0 0 N N N 41.689 29.132 43.909 5.116 -1.136 -2.852 HE2 LYS 43 LPR H132 2H13 H 0 0 N N N 42.046 28.583 45.587 4.695 0.102 -4.059 HE3 LYS 44 LPR O4 O4 O 0 1 N N N 38.843 33.368 41.867 -5.020 -1.510 -2.018 OXT PRO 45 LPR O5 O5 O 0 1 N N N 40.703 32.272 42.326 -2.866 -1.899 -2.317 O PRO 46 LPR N2 N2 N 0 1 N N N 41.810 34.533 43.599 -1.931 0.504 -1.745 N PRO 47 LPR C5 C5 C 0 1 N N S 40.715 34.685 42.559 -3.384 0.303 -1.659 CA PRO 48 LPR C6 C6 C 0 1 N N N 41.505 35.237 41.353 -4.042 1.279 -2.658 CB PRO 49 LPR C7 C7 C 0 1 N N N 42.826 35.369 41.680 -2.954 2.369 -2.849 CG PRO 50 LPR C8 C8 C 0 1 N N N 43.138 34.956 43.062 -1.655 1.529 -2.768 CD PRO 51 LPR C9 C9 C 0 1 N N N 40.081 33.284 42.224 -3.737 -1.116 -2.022 C PRO 52 LPR H4 H4 H 0 1 N N N 38.347 34.174 41.785 -5.247 -2.421 -2.250 HXT PRO 53 LPR H5 H5 H 0 1 N N N 39.876 35.324 42.871 -3.725 0.522 -0.647 HA PRO 54 LPR H6 H6 H 0 1 N N N 41.084 35.479 40.409 -4.950 1.710 -2.238 HB2 PRO 55 LPR H62 2H6 H 0 1 N N N 41.071 36.190 40.970 -4.253 0.775 -3.601 HB3 PRO 56 LPR H7 H7 H 0 1 N N N 43.558 35.734 41.004 -2.994 3.105 -2.046 HG2 PRO 57 LPR H72 2H7 H 0 1 N N N 43.176 36.410 41.491 -3.049 2.849 -3.822 HG3 PRO 58 LPR H8C1 1H8C H 0 0 N N N 43.549 35.796 43.642 -0.817 2.155 -2.462 HD2 PRO 59 LPR H8C2 2H8C H 0 0 N N N 43.897 34.162 43.114 -1.447 1.059 -3.729 HD3 PRO 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 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" LPR InChI InChI 1.03 "InChI=1S/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" LPR InChIKey InChI 1.03 RLAWWYSOJDYHDC-BZSNNMDCSA-N # # 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" # # loop_ _pdbx_chem_comp_audit.comp_id _pdbx_chem_comp_audit.action_type _pdbx_chem_comp_audit.date _pdbx_chem_comp_audit.processing_site LPR "Create component" 2002-11-25 EBI LPR "Modify descriptor" 2011-06-04 RCSB LPR "Modify synonyms" 2020-06-05 PDBE # _pdbx_chem_comp_synonyms.ordinal 1 _pdbx_chem_comp_synonyms.comp_id LPR _pdbx_chem_comp_synonyms.name LISINOPRIL _pdbx_chem_comp_synonyms.provenance ? _pdbx_chem_comp_synonyms.type ? ##