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                    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                        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 InChI            InChI                1.02b InChI=1/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                1.02b WOXKDUGGOYFFRN-IIBYNOLFBU                                                                                                                                    
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                                                                                                         
# 
_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" 
# 
