data_LIR # _chem_comp.id LIR _chem_comp.name "2-[(3S)-3-AMINOPIPERIDIN-1-YL]-1-(2-CYANOBENZYL)-5-METHYL-4,6-DIOXO-3,4,5,6-TETRAHYDROPYRROLO[3,4-D]IMIDAZOL-1-IUM" _chem_comp.type NON-POLYMER _chem_comp.pdbx_type HETAIN _chem_comp.formula "C19 H21 N6 O2" _chem_comp.mon_nstd_parent_comp_id ? _chem_comp.pdbx_synonyms ? _chem_comp.pdbx_formal_charge 1 _chem_comp.pdbx_initial_date 2006-08-22 _chem_comp.pdbx_modified_date 2011-06-04 _chem_comp.pdbx_ambiguous_flag ? _chem_comp.pdbx_release_status REL _chem_comp.pdbx_replaced_by ? _chem_comp.pdbx_replaces ? _chem_comp.formula_weight 365.409 _chem_comp.one_letter_code ? _chem_comp.three_letter_code LIR _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 2I3Z _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 LIR C4 C4 C 0 1 N N N 18.931 39.753 -78.219 -0.396 6.838 2.476 C4 LIR 1 LIR C7 C7 C 0 1 Y N N 15.395 38.798 -78.602 -1.848 3.573 2.031 C7 LIR 2 LIR N12 N12 N 0 1 N N N 14.061 38.314 -78.414 -1.999 2.260 1.608 N12 LIR 3 LIR C13 C13 C 0 1 N N N 13.964 36.911 -78.817 -1.494 1.096 2.383 C13 LIR 4 LIR C15 C15 C 0 1 N N N 12.048 36.567 -77.241 -1.217 -0.157 0.225 C15 LIR 5 LIR C17 C17 C 0 1 N N N 13.532 38.586 -77.046 -2.670 1.916 0.331 C17 LIR 6 LIR C20 C20 C 0 1 Y N N 15.400 39.230 -82.261 -3.749 3.159 4.662 C20 LIR 7 LIR C21 C21 C 0 1 Y N N 15.298 40.220 -83.254 -2.950 3.837 5.576 C21 LIR 8 LIR C22 C22 C 0 1 Y N N 15.760 39.978 -84.559 -2.724 3.287 6.837 C22 LIR 9 LIR C24 C24 C 0 1 Y N N 16.487 37.742 -83.914 -4.100 1.388 6.256 C24 LIR 10 LIR C26 C26 C 0 1 N N N 16.188 36.909 -81.667 -5.151 1.228 4.066 C26 LIR 11 LIR C1 C1 C 0 1 N N N 18.279 40.422 -80.270 -2.501 6.734 3.625 C1 LIR 12 LIR C2 C2 C 0 1 Y N N 17.155 39.762 -79.601 -2.199 5.518 2.982 C2 LIR 13 LIR C3 C3 C 0 1 Y N N 17.529 39.378 -78.413 -1.007 5.577 2.332 C3 LIR 14 LIR N5 N5 N 0 1 N N N 19.306 40.351 -79.379 -1.361 7.493 3.274 N5 LIR 15 LIR N6 N6 N 1 1 Y N N 15.757 39.380 -79.760 -2.713 4.274 2.790 N6 LIR 16 LIR N8 N8 N 0 1 Y N N 16.408 38.734 -77.710 -0.797 4.368 1.746 N8 LIR 17 LIR O9 O9 O 0 1 N N N 18.293 40.899 -81.397 -3.455 7.090 4.301 O9 LIR 18 LIR O10 O10 O 0 1 N N N 19.610 39.540 -77.235 0.662 7.286 2.056 O10 LIR 19 LIR C11 C11 C 0 1 N N N 20.641 40.895 -79.624 -1.205 8.866 3.718 C11 LIR 20 LIR C14 C14 C 0 1 N N S 12.558 36.370 -78.680 -0.532 0.271 1.529 C14 LIR 21 LIR C16 C16 C 0 1 N N N 12.076 38.071 -76.913 -1.754 1.055 -0.537 C16 LIR 22 LIR N18 N18 N 0 1 N N N 12.609 34.978 -79.123 -0.089 -0.907 2.270 N18 LIR 23 LIR C19 C19 C 0 1 N N N 14.860 39.562 -80.899 -3.970 3.784 3.311 C19 LIR 24 LIR C23 C23 C 0 1 Y N N 16.366 38.746 -84.881 -3.299 2.063 7.177 C23 LIR 25 LIR C25 C25 C 0 1 Y N N 16.027 37.979 -82.608 -4.326 1.939 4.994 C25 LIR 26 LIR N27 N27 N 0 1 N N N 16.401 36.121 -80.838 -5.820 0.652 3.314 N27 LIR 27 LIR H131 1H13 H 0 0 N N N 14.632 36.316 -78.176 -2.363 0.509 2.704 H131 LIR 28 LIR H132 2H13 H 0 0 N N N 14.250 36.843 -79.877 -0.992 1.472 3.282 H132 LIR 29 LIR H151 1H15 H 0 0 N N N 11.020 36.186 -77.155 -2.048 -0.842 0.440 H151 LIR 30 LIR H152 2H15 H 0 0 N N N 12.689 36.017 -76.536 -0.512 -0.703 -0.413 H152 LIR 31 LIR H171 1H17 H 0 0 N N N 14.164 38.073 -76.307 -2.935 2.840 -0.194 H171 LIR 32 LIR H172 2H17 H 0 0 N N N 13.543 39.672 -76.870 -3.596 1.382 0.572 H172 LIR 33 LIR H21 H21 H 0 1 N N N 14.860 41.177 -83.011 -2.497 4.792 5.321 H21 LIR 34 LIR H22 H22 H 0 1 N N N 15.651 40.738 -85.318 -2.100 3.812 7.555 H22 LIR 35 LIR H24 H24 H 0 1 N N N 16.931 36.791 -84.170 -4.541 0.435 6.537 H24 LIR 36 LIR HN8 HN8 H 0 1 N N N 16.398 38.342 -76.790 0.009 4.100 1.188 HN8 LIR 37 LIR H111 1H11 H 0 0 N N N 20.789 41.032 -80.705 -2.032 9.145 4.375 H111 LIR 38 LIR H112 2H11 H 0 0 N N N 20.741 41.865 -79.115 -1.195 9.543 2.859 H112 LIR 39 LIR H113 3H11 H 0 0 N N N 21.398 40.197 -79.236 -0.266 8.982 4.266 H113 LIR 40 LIR H14 H14 H 0 1 N N N 11.829 36.908 -79.304 0.346 0.880 1.285 H14 LIR 41 LIR H161 1H16 H 0 0 N N N 11.425 38.615 -77.614 -0.906 1.664 -0.875 H161 LIR 42 LIR H162 2H16 H 0 0 N N N 11.715 38.236 -75.887 -2.292 0.726 -1.433 H162 LIR 43 LIR H181 1H18 H 0 0 N N N 12.621 34.946 -80.122 -0.498 -1.080 3.163 H181 LIR 44 LIR H182 2H18 H 0 0 N N N 13.437 34.545 -78.766 0.735 -1.374 1.960 H182 LIR 45 LIR H191 1H19 H 0 0 N N N 14.576 40.625 -80.917 -4.398 3.058 2.610 H191 LIR 46 LIR H192 2H19 H 0 0 N N N 14.038 38.849 -80.734 -4.686 4.612 3.376 H192 LIR 47 LIR H23 H23 H 0 1 N N N 16.739 38.576 -85.880 -3.123 1.635 8.160 H23 LIR 48 # 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 LIR C4 N5 SING N N 1 LIR C4 C3 SING N N 2 LIR C4 O10 DOUB N N 3 LIR C7 N6 DOUB Y N 4 LIR C7 N12 SING N N 5 LIR C7 N8 SING Y N 6 LIR N12 C13 SING N N 7 LIR N12 C17 SING N N 8 LIR C13 C14 SING N N 9 LIR C13 H131 SING N N 10 LIR C13 H132 SING N N 11 LIR C15 C14 SING N N 12 LIR C15 C16 SING N N 13 LIR C15 H151 SING N N 14 LIR C15 H152 SING N N 15 LIR C17 C16 SING N N 16 LIR C17 H171 SING N N 17 LIR C17 H172 SING N N 18 LIR C20 C21 DOUB Y N 19 LIR C20 C25 SING Y N 20 LIR C20 C19 SING N N 21 LIR C21 C22 SING Y N 22 LIR C21 H21 SING N N 23 LIR C22 C23 DOUB Y N 24 LIR C22 H22 SING N N 25 LIR C24 C23 SING Y N 26 LIR C24 C25 DOUB Y N 27 LIR C24 H24 SING N N 28 LIR C26 C25 SING N N 29 LIR C26 N27 TRIP N N 30 LIR C1 O9 DOUB N N 31 LIR C1 C2 SING N N 32 LIR C1 N5 SING N N 33 LIR C2 N6 SING Y N 34 LIR C2 C3 DOUB Y N 35 LIR C3 N8 SING Y N 36 LIR N5 C11 SING N N 37 LIR N6 C19 SING N N 38 LIR N8 HN8 SING N N 39 LIR C11 H111 SING N N 40 LIR C11 H112 SING N N 41 LIR C11 H113 SING N N 42 LIR C14 N18 SING N N 43 LIR C14 H14 SING N N 44 LIR C16 H161 SING N N 45 LIR C16 H162 SING N N 46 LIR N18 H181 SING N N 47 LIR N18 H182 SING N N 48 LIR C19 H191 SING N N 49 LIR C19 H192 SING N N 50 LIR C23 H23 SING N N 51 # 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 LIR SMILES ACDLabs 10.04 "N#Cc1ccccc1C[n+]2c(nc3c2C(=O)N(C3=O)C)N4CCCC(N)C4" LIR SMILES_CANONICAL CACTVS 3.341 "CN1C(=O)c2[nH]c(N3CCC[C@H](N)C3)[n+](Cc4ccccc4C#N)c2C1=O" LIR SMILES CACTVS 3.341 "CN1C(=O)c2[nH]c(N3CCC[CH](N)C3)[n+](Cc4ccccc4C#N)c2C1=O" LIR SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 "CN1C(=O)c2c([n+](c([nH]2)N3CCC[C@@H](C3)N)Cc4ccccc4C#N)C1=O" LIR SMILES "OpenEye OEToolkits" 1.5.0 "CN1C(=O)c2c([n+](c([nH]2)N3CCCC(C3)N)Cc4ccccc4C#N)C1=O" LIR InChI InChI 1.03 "InChI=1S/C19H20N6O2/c1-23-17(26)15-16(18(23)27)25(10-13-6-3-2-5-12(13)9-20)19(22-15)24-8-4-7-14(21)11-24/h2-3,5-6,14H,4,7-8,10-11,21H2,1H3/p+1/t14-/m0/s1" LIR InChIKey InChI 1.03 WVRGIUWTFUXDGX-AWEZNQCLSA-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 LIR "SYSTEMATIC NAME" ACDLabs 10.04 "2-[(3S)-3-aminopiperidin-1-yl]-1-(2-cyanobenzyl)-5-methyl-4,6-dioxo-3,4,5,6-tetrahydropyrrolo[3,4-d]imidazol-1-ium" LIR "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "2-[[2-[(3S)-3-aminopiperidin-1-yl]-5-methyl-4,6-dioxo-3H-pyrrolo[3,4-d]imidazol-1-ium-1-yl]methyl]benzonitrile" # loop_ _pdbx_chem_comp_audit.comp_id _pdbx_chem_comp_audit.action_type _pdbx_chem_comp_audit.date _pdbx_chem_comp_audit.processing_site LIR "Create component" 2006-08-22 RCSB LIR "Modify descriptor" 2011-06-04 RCSB #