data_CIA # _chem_comp.id CIA _chem_comp.name "6-BENZO[1,3]DIOXOL-5-YL-2-METHYL-2,3,6,7,12,12A-HEXAHYDRO-PYRAZINO[1',2':1,6]PYRIDO[3,4-B]INDOLE-1,4-DIONE" _chem_comp.type NON-POLYMER _chem_comp.pdbx_type HETAIN _chem_comp.formula "C22 H19 N3 O4" _chem_comp.mon_nstd_parent_comp_id ? _chem_comp.pdbx_synonyms "TADALAFIL; CIALIS" _chem_comp.pdbx_formal_charge 0 _chem_comp.pdbx_initial_date 2003-05-08 _chem_comp.pdbx_modified_date 2020-05-27 _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 389.404 _chem_comp.one_letter_code ? _chem_comp.three_letter_code CIA _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 1UDU _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 CIA C3 C3 C 0 1 Y N N 24.435 39.243 103.913 -3.558 -4.390 -0.424 C3 CIA 1 CIA C2 C2 C 0 1 Y N N 24.136 38.324 102.831 -4.324 -3.380 -0.981 C2 CIA 2 CIA C1 C1 C 0 1 Y N N 22.783 38.095 102.381 -3.965 -2.057 -0.889 C1 CIA 3 CIA C6 C6 C 0 1 Y N N 21.678 38.816 103.045 -2.782 -1.770 -0.203 C6 CIA 4 CIA C7 C7 C 0 1 Y N N 20.265 38.832 102.866 -2.093 -0.529 0.092 C7 CIA 5 CIA C8 C8 C 0 1 Y N N 19.777 39.758 103.858 -0.986 -0.850 0.795 C8 CIA 6 CIA N9 N9 N 0 1 Y N N 20.831 40.320 104.644 -0.919 -2.207 0.967 N9 CIA 7 CIA C5 C5 C 0 1 Y N N 21.988 39.748 104.150 -1.994 -2.801 0.372 C5 CIA 8 CIA C4 C4 C 0 1 Y N N 23.384 39.955 104.577 -2.383 -4.134 0.262 C4 CIA 9 CIA C13 C13 C 0 1 N N R 18.220 40.076 104.023 0.006 0.173 1.302 C13 CIA 10 CIA N12 N12 N 0 1 N N N 17.274 38.982 103.387 -0.311 1.458 0.643 N12 CIA 11 CIA C17 C17 C 0 1 N N N 15.867 39.093 103.497 0.686 2.189 0.139 C17 CIA 12 CIA O20 O20 O 0 1 N N N 15.251 40.023 104.071 1.806 1.726 0.184 O20 CIA 13 CIA C16 C16 C 0 1 N N N 14.965 37.999 102.900 0.515 3.540 -0.475 C16 CIA 14 CIA N15 N15 N 0 1 N N N 15.552 37.146 101.801 -0.868 3.986 -0.438 N15 CIA 15 CIA C31 C31 C 0 1 N N N 16.948 37.002 101.611 -1.871 3.250 0.038 C31 CIA 16 CIA O32 O32 O 0 1 N N N 17.432 36.293 100.678 -2.984 3.731 0.024 O32 CIA 17 CIA C11 C11 C 0 1 N N R 17.928 37.758 102.648 -1.713 1.867 0.582 C11 CIA 18 CIA C10 C10 C 0 1 N N N 19.261 38.105 101.898 -2.491 0.873 -0.292 C10 CIA 19 CIA C18 C18 C 0 1 N N N 14.557 36.465 100.936 -1.176 5.324 -0.950 C18 CIA 20 CIA C22 C22 C 0 1 Y N N 18.037 41.572 103.414 1.407 -0.254 0.950 C22 CIA 21 CIA C27 C27 C 0 1 Y N N 17.247 42.553 104.134 2.384 -0.289 1.928 C27 CIA 22 CIA C26 C26 C 0 1 Y N N 17.079 43.883 103.615 3.671 -0.680 1.610 C26 CIA 23 CIA C25 C25 C 0 1 Y N N 17.721 44.248 102.333 3.986 -1.039 0.309 C25 CIA 24 CIA O30 O30 O 0 1 N N N 17.689 45.437 101.674 5.156 -1.454 -0.258 O30 CIA 25 CIA C29 C29 C 0 1 N N N 18.497 45.181 100.487 4.979 -1.281 -1.676 C29 CIA 26 CIA O28 O28 O 0 1 N N N 18.998 43.812 100.484 3.555 -1.398 -1.860 O28 CIA 27 CIA C24 C24 C 0 1 Y N N 18.495 43.294 101.625 3.002 -1.004 -0.676 C24 CIA 28 CIA C23 C23 C 0 1 Y N N 18.663 41.988 102.130 1.713 -0.616 -0.349 C23 CIA 29 CIA H3 H3 H 0 1 N N N 25.478 39.403 104.236 -3.889 -5.413 -0.528 H3 CIA 30 CIA H2 H2 H 0 1 N N N 24.961 37.784 102.336 -5.232 -3.640 -1.504 H2 CIA 31 CIA H1 H1 H 0 1 N N N 22.599 37.389 101.554 -4.568 -1.276 -1.327 H1 CIA 32 CIA HN9 HN9 H 0 1 N N N 20.770 40.995 105.406 -0.214 -2.675 1.441 HN9 CIA 33 CIA H4 H4 H 0 1 N N N 23.643 40.646 105.397 -1.794 -4.932 0.692 H4 CIA 34 CIA H13 H13 H 0 1 N N N 17.901 40.041 105.091 -0.089 0.277 2.383 H13 CIA 35 CIA H161 1H16 H 0 0 N N N 14.012 38.457 102.546 0.847 3.502 -1.513 H161 CIA 36 CIA H162 2H16 H 0 0 N N N 14.588 37.342 103.718 1.132 4.257 0.067 H162 CIA 37 CIA H11 H11 H 0 1 N N N 18.153 37.067 103.494 -2.129 1.850 1.590 H11 CIA 38 CIA H101 1H10 H 0 0 N N N 19.718 37.204 101.427 -3.561 1.006 -0.132 H101 CIA 39 CIA H102 2H10 H 0 0 N N N 19.074 38.699 100.973 -2.253 1.046 -1.342 H102 CIA 40 CIA H181 1H18 H 0 0 N N N 13.846 37.210 100.507 -0.259 5.799 -1.297 H181 CIA 41 CIA H182 2H18 H 0 0 N N N 14.991 35.835 100.125 -1.881 5.243 -1.778 H182 CIA 42 CIA H183 3H18 H 0 0 N N N 13.855 35.862 101.558 -1.618 5.924 -0.154 H183 CIA 43 CIA H27 H27 H 0 1 N N N 16.767 42.284 105.090 2.141 -0.009 2.942 H27 CIA 44 CIA H26 H26 H 0 1 N N N 16.472 44.606 104.186 4.432 -0.706 2.375 H26 CIA 45 CIA H291 1H29 H 0 0 N N N 19.324 45.922 100.384 5.326 -0.296 -1.988 H291 CIA 46 CIA H292 2H29 H 0 0 N N N 17.940 45.418 99.551 5.501 -2.064 -2.226 H292 CIA 47 CIA H23 H23 H 0 1 N N N 19.278 41.299 101.527 0.946 -0.593 -1.110 H23 CIA 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 CIA C3 C2 DOUB Y N 1 CIA C3 C4 SING Y N 2 CIA C3 H3 SING N N 3 CIA C2 C1 SING Y N 4 CIA C2 H2 SING N N 5 CIA C1 C6 DOUB Y N 6 CIA C1 H1 SING N N 7 CIA C6 C7 SING Y N 8 CIA C6 C5 SING Y N 9 CIA C7 C8 DOUB Y N 10 CIA C7 C10 SING N N 11 CIA C8 N9 SING Y N 12 CIA C8 C13 SING N N 13 CIA N9 C5 SING Y N 14 CIA N9 HN9 SING N N 15 CIA C5 C4 DOUB Y N 16 CIA C4 H4 SING N N 17 CIA C13 N12 SING N N 18 CIA C13 C22 SING N N 19 CIA C13 H13 SING N N 20 CIA N12 C17 SING N N 21 CIA N12 C11 SING N N 22 CIA C17 O20 DOUB N N 23 CIA C17 C16 SING N N 24 CIA C16 N15 SING N N 25 CIA C16 H161 SING N N 26 CIA C16 H162 SING N N 27 CIA N15 C31 SING N N 28 CIA N15 C18 SING N N 29 CIA C31 O32 DOUB N N 30 CIA C31 C11 SING N N 31 CIA C11 C10 SING N N 32 CIA C11 H11 SING N N 33 CIA C10 H101 SING N N 34 CIA C10 H102 SING N N 35 CIA C18 H181 SING N N 36 CIA C18 H182 SING N N 37 CIA C18 H183 SING N N 38 CIA C22 C27 DOUB Y N 39 CIA C22 C23 SING Y N 40 CIA C27 C26 SING Y N 41 CIA C27 H27 SING N N 42 CIA C26 C25 DOUB Y N 43 CIA C26 H26 SING N N 44 CIA C25 O30 SING N N 45 CIA C25 C24 SING Y N 46 CIA O30 C29 SING N N 47 CIA C29 O28 SING N N 48 CIA C29 H291 SING N N 49 CIA C29 H292 SING N N 50 CIA O28 C24 SING N N 51 CIA C24 C23 DOUB Y N 52 CIA C23 H23 SING N N 53 # 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 CIA SMILES ACDLabs 10.04 "O=C1N(C)CC(=O)N6C1Cc3c2ccccc2nc3C6c4ccc5OCOc5c4" CIA SMILES_CANONICAL CACTVS 3.341 "CN1CC(=O)N2[C@H](Cc3c([nH]c4ccccc34)[C@H]2c5ccc6OCOc6c5)C1=O" CIA SMILES CACTVS 3.341 "CN1CC(=O)N2[CH](Cc3c([nH]c4ccccc34)[CH]2c5ccc6OCOc6c5)C1=O" CIA SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 "CN1CC(=O)N2[C@@H](C1=O)Cc3c4ccccc4[nH]c3[C@H]2c5ccc6c(c5)OCO6" CIA SMILES "OpenEye OEToolkits" 1.5.0 "CN1CC(=O)N2C(C1=O)Cc3c4ccccc4[nH]c3C2c5ccc6c(c5)OCO6" CIA InChI InChI 1.03 "InChI=1S/C22H19N3O4/c1-24-10-19(26)25-16(22(24)27)9-14-13-4-2-3-5-15(13)23-20(14)21(25)12-6-7-17-18(8-12)29-11-28-17/h2-8,16,21,23H,9-11H2,1H3/t16-,21-/m1/s1" CIA InChIKey InChI 1.03 WOXKDUGGOYFFRN-IIBYNOLFSA-N # _pdbx_chem_comp_identifier.comp_id CIA _pdbx_chem_comp_identifier.type "SYSTEMATIC NAME" _pdbx_chem_comp_identifier.program ACDLabs _pdbx_chem_comp_identifier.program_version 10.04 _pdbx_chem_comp_identifier.identifier "(6R,12aR)-6-(1,3-benzodioxol-5-yl)-2-methyl-2,3,6,7,12,12a-hexahydropyrazino[1',2':1,6]pyrido[3,4-b]indole-1,4-dione" # loop_ _pdbx_chem_comp_audit.comp_id _pdbx_chem_comp_audit.action_type _pdbx_chem_comp_audit.date _pdbx_chem_comp_audit.processing_site CIA "Create component" 2003-05-08 RCSB CIA "Modify descriptor" 2011-06-04 RCSB CIA "Modify synonyms" 2020-05-27 PDBE # loop_ _pdbx_chem_comp_synonyms.ordinal _pdbx_chem_comp_synonyms.comp_id _pdbx_chem_comp_synonyms.name _pdbx_chem_comp_synonyms.provenance _pdbx_chem_comp_synonyms.type 1 CIA TADALAFIL ? ? 2 CIA CIALIS ? ? #