data_UIR
# 
_chem_comp.id                                    UIR 
_chem_comp.name                                  (1R,3AS,4R,8AS,8BR)-4-(2-BENZO[1,3]DIOXOL-5-YL-1-CYCLOPROPYL-3-OXO-DECAHYDRO-PYRROLO[3,4-A]PYRROLIZIN-4-YL)-BENZAMIDINE 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C27 H30 N4 O3" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         ? 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2003-07-16 
_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                        458.552 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     UIR 
_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   Y 
_chem_comp.pdbx_model_coordinates_db_code        1Y3V 
_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 
UIR N1   N1   N 0 1 N N N -5.018 9.507  19.626 5.996  -1.757 1.161  N1   UIR 1  
UIR C3   C3   C 0 1 N N N -3.704 9.277  19.627 5.123  -0.894 0.727  C3   UIR 2  
UIR C4   C4   C 0 1 Y N N -3.118 8.054  20.097 3.756  -1.339 0.370  C4   UIR 3  
UIR C9   C9   C 0 1 Y N N -3.864 7.106  20.824 3.401  -2.681 0.499  C9   UIR 4  
UIR C8   C8   C 0 1 Y N N -3.263 5.915  21.295 2.126  -3.089 0.165  C8   UIR 5  
UIR C7   C7   C 0 1 Y N N -1.905 5.663  21.035 1.201  -2.170 -0.297 C7   UIR 6  
UIR C10  C10  C 0 1 N N R -1.180 4.448  21.580 -0.190 -2.623 -0.660 C10  UIR 7  
UIR N11  N11  N 0 1 N N N -2.179 3.319  21.588 -0.650 -1.903 -1.858 N11  UIR 8  
UIR C12  C12  C 0 1 N N N -2.486 2.854  20.195 -1.113 -3.008 -2.826 C12  UIR 9  
UIR C13  C13  C 0 1 N N N -1.538 1.660  19.952 -2.193 -2.306 -3.684 C13  UIR 10 
UIR C14  C14  C 0 1 N N N -0.729 1.407  21.207 -2.908 -1.394 -2.661 C14  UIR 11 
UIR C15  C15  C 0 1 N N S -1.413 2.230  22.314 -1.883 -1.174 -1.538 C15  UIR 12 
UIR C16  C16  C 0 1 N N R -0.307 2.926  23.176 -2.423 -1.739 -0.216 C16  UIR 13 
UIR C18  C18  C 0 1 N N N 0.489  2.733  25.728 -3.845 -1.059 1.753  C18  UIR 14 
UIR C17  C17  C 0 1 N N R -0.629 2.695  24.703 -2.815 -0.581 0.727  C17  UIR 15 
UIR C42  C42  C 0 1 N N N 0.294  1.800  26.931 -4.451 -0.010 2.687  C42  UIR 16 
UIR C41  C41  C 0 1 N N N 1.304  1.417  25.816 -5.294 -0.609 1.560  C41  UIR 17 
UIR N19  N19  N 0 1 N N N -1.651 3.659  24.998 -1.574 -0.183 1.401  N19  UIR 18 
UIR C20  C20  C 0 1 N N N -1.694 4.699  24.091 -0.623 -1.143 1.298  C20  UIR 19 
UIR O21  O21  O 0 1 N N N -2.581 5.625  24.104 0.490  -1.070 1.774  O21  UIR 20 
UIR C22  C22  C 0 1 N N S -0.621 4.452  23.011 -1.156 -2.303 0.489  C22  UIR 21 
UIR C23  C23  C 0 1 N N N -2.716 3.721  26.091 -1.387 1.087  2.106  C23  UIR 22 
UIR C24  C24  C 0 1 Y N N -2.467 4.852  27.096 -0.992 2.156  1.120  C24  UIR 23 
UIR C25  C25  C 0 1 Y N N -1.250 4.900  27.794 0.337  2.327  0.783  C25  UIR 24 
UIR C26  C26  C 0 1 Y N N -1.087 5.925  28.821 0.702  3.306  -0.127 C26  UIR 25 
UIR O27  O27  O 0 1 N N N -0.355 5.780  30.022 1.919  3.672  -0.624 O27  UIR 26 
UIR C28  C28  C 0 1 N N N -0.415 7.158  30.531 1.636  4.446  -1.804 C28  UIR 27 
UIR O29  O29  O 0 1 N N N -1.617 7.791  29.972 0.333  5.001  -1.545 O29  UIR 28 
UIR C30  C30  C 0 1 Y N N -2.126 6.847  29.097 -0.274 4.123  -0.694 C30  UIR 29 
UIR C31  C31  C 0 1 Y N N -3.338 6.790  28.412 -1.604 3.949  -0.348 C31  UIR 30 
UIR C32  C32  C 0 1 Y N N -3.496 5.799  27.410 -1.961 2.967  0.557  C32  UIR 31 
UIR C6   C6   C 0 1 Y N N -1.140 6.593  20.291 1.547  -0.837 -0.427 C6   UIR 32 
UIR C5   C5   C 0 1 Y N N -1.751 7.768  19.839 2.818  -0.416 -0.090 C5   UIR 33 
UIR N2   N2   N 0 1 N N N -2.959 10.398 19.277 5.471  0.433  0.598  N2   UIR 34 
UIR HN11 1HN1 H 0 0 N N N -5.353 9.356  20.578 ?      ?      ?      HN11 UIR 35 
UIR HN12 2HN1 H 0 0 N N N -5.434 10.376 19.292 5.751  -2.692 1.251  HN12 UIR 36 
UIR H9   H9   H 0 1 N N N -4.931 7.299  21.027 4.122  -3.400 0.858  H9   UIR 37 
UIR H8   H8   H 0 1 N N N -3.855 5.181  21.867 1.849  -4.129 0.264  H8   UIR 38 
UIR H10  H10  H 0 1 N N N -0.286 4.385  20.916 -0.189 -3.695 -0.853 H10  UIR 39 
UIR H121 1H12 H 0 0 N N N -2.408 3.656  19.424 -1.542 -3.852 -2.286 H121 UIR 40 
UIR H122 2H12 H 0 0 N N N -3.562 2.617  20.025 -0.281 -3.334 -3.449 H122 UIR 41 
UIR H131 1H13 H 0 0 N N N -0.893 1.806  19.054 -2.888 -3.035 -4.102 H131 UIR 42 
UIR H132 2H13 H 0 0 N N N -2.082 0.750  19.608 -1.733 -1.712 -4.474 H132 UIR 43 
UIR H141 1H14 H 0 0 N N N 0.358  1.629  21.091 -3.798 -1.888 -2.270 H141 UIR 44 
UIR H142 2H14 H 0 0 N N N -0.617 0.326  21.457 -3.174 -0.443 -3.122 H142 UIR 45 
UIR H15  H15  H 0 1 N N N -2.062 1.599  22.965 -1.655 -0.114 -1.433 H15  UIR 46 
UIR H16  H16  H 0 1 N N N 0.712  2.575  22.890 -3.215 -2.476 -0.351 H16  UIR 47 
UIR H18  H18  H 0 1 N N N 0.736  3.814  25.608 -3.677 -2.057 2.158  H18  UIR 48 
UIR H17  H17  H 0 1 N N N -0.920 1.624  24.813 -3.215 0.254  0.153  H17  UIR 49 
UIR H421 1H42 H 0 0 N N N -0.583 1.299  27.403 -4.682 -0.318 3.707  H421 UIR 50 
UIR H422 2H42 H 0 0 N N N 0.354  1.921  28.038 -4.115 1.020  2.572  H422 UIR 51 
UIR H411 1H41 H 0 0 N N N 2.386  1.149  25.782 -5.514 0.028  0.703  H411 UIR 52 
UIR H412 2H41 H 0 0 N N N 1.459  0.533  25.154 -6.080 -1.311 1.838  H412 UIR 53 
UIR H22  H22  H 0 1 N N N 0.183  5.216  23.129 -1.372 -3.175 1.106  H22  UIR 54 
UIR H231 1H23 H 0 0 N N N -2.814 2.739  26.610 -2.318 1.371  2.596  H231 UIR 55 
UIR H232 2H23 H 0 0 N N N -3.738 3.795  25.650 -0.602 0.976  2.854  H232 UIR 56 
UIR H25  H25  H 0 1 N N N -0.461 4.169  27.548 1.092  1.696  1.228  H25  UIR 57 
UIR H281 1H28 H 0 0 N N N 0.515  7.737  30.324 1.612  3.806  -2.686 H281 UIR 58 
UIR H282 2H28 H 0 0 N N N -0.376 7.210  31.644 2.373  5.241  -1.927 H282 UIR 59 
UIR H31  H31  H 0 1 N N N -4.143 7.504  28.654 -2.362 4.581  -0.786 H31  UIR 60 
UIR H32  H32  H 0 1 N N N -4.450 5.764  26.857 -2.998 2.833  0.826  H32  UIR 61 
UIR H6   H6   H 0 1 N N N -0.077 6.404  20.065 0.821  -0.124 -0.789 H6   UIR 62 
UIR H5   H5   H 0 1 N N N -1.141 8.486  19.266 3.087  0.625  -0.192 H5   UIR 63 
UIR HN2  HN2  H 0 1 N N N -1.974 10.336 19.534 4.822  1.075  0.271  HN2  UIR 64 
# 
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 
UIR N1  C3   SING N N 1  
UIR N1  HN11 SING N N 2  
UIR N1  HN12 SING N N 3  
UIR C3  C4   SING N N 4  
UIR C3  N2   DOUB N N 5  
UIR C4  C9   DOUB Y N 6  
UIR C4  C5   SING Y N 7  
UIR C9  C8   SING Y N 8  
UIR C9  H9   SING N N 9  
UIR C8  C7   DOUB Y N 10 
UIR C8  H8   SING N N 11 
UIR C7  C10  SING N N 12 
UIR C7  C6   SING Y N 13 
UIR C10 N11  SING N N 14 
UIR C10 C22  SING N N 15 
UIR C10 H10  SING N N 16 
UIR N11 C12  SING N N 17 
UIR N11 C15  SING N N 18 
UIR C12 C13  SING N N 19 
UIR C12 H121 SING N N 20 
UIR C12 H122 SING N N 21 
UIR C13 C14  SING N N 22 
UIR C13 H131 SING N N 23 
UIR C13 H132 SING N N 24 
UIR C14 C15  SING N N 25 
UIR C14 H141 SING N N 26 
UIR C14 H142 SING N N 27 
UIR C15 C16  SING N N 28 
UIR C15 H15  SING N N 29 
UIR C16 C17  SING N N 30 
UIR C16 C22  SING N N 31 
UIR C16 H16  SING N N 32 
UIR C18 C17  SING N N 33 
UIR C18 C42  SING N N 34 
UIR C18 C41  SING N N 35 
UIR C18 H18  SING N N 36 
UIR C17 N19  SING N N 37 
UIR C17 H17  SING N N 38 
UIR C42 C41  SING N N 39 
UIR C42 H421 SING N N 40 
UIR C42 H422 SING N N 41 
UIR C41 H411 SING N N 42 
UIR C41 H412 SING N N 43 
UIR N19 C20  SING N N 44 
UIR N19 C23  SING N N 45 
UIR C20 O21  DOUB N N 46 
UIR C20 C22  SING N N 47 
UIR C22 H22  SING N N 48 
UIR C23 C24  SING N N 49 
UIR C23 H231 SING N N 50 
UIR C23 H232 SING N N 51 
UIR C24 C25  DOUB Y N 52 
UIR C24 C32  SING Y N 53 
UIR C25 C26  SING Y N 54 
UIR C25 H25  SING N N 55 
UIR C26 O27  SING N N 56 
UIR C26 C30  DOUB Y N 57 
UIR O27 C28  SING N N 58 
UIR C28 O29  SING N N 59 
UIR C28 H281 SING N N 60 
UIR C28 H282 SING N N 61 
UIR O29 C30  SING N N 62 
UIR C30 C31  SING Y N 63 
UIR C31 C32  DOUB Y N 64 
UIR C31 H31  SING N N 65 
UIR C32 H32  SING N N 66 
UIR C6  C5   DOUB Y N 67 
UIR C6  H6   SING N N 68 
UIR C5  H5   SING N N 69 
UIR N2  HN2  SING N N 70 
# 
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 
UIR SMILES           ACDLabs              10.04 O=C2N(C(C1CC1)C5C2C(c3ccc(C(=[N@H])N)cc3)N4CCCC45)Cc6ccc7OCOc7c6 
UIR InChI            InChI                1.02b 
InChI=1/C27H30N4O3/c28-26(29)18-8-6-17(7-9-18)25-23-22(19-2-1-11-30(19)25)24(16-4-5-16)31(27(23)32)13-15-3-10-20-21(12-15)34-14-33-20/h3,6-10,12,16,19,22-25H,1-2,4-5,11,13-14H2,(H3,28,29)/t19-,22-,23-,24+,25-/m0/s1/f/h28H,29H2/b28-26+ 
UIR InChIKey         InChI                1.02b XYMBMAVAMICSMV-GIKJZOHXDS 
UIR SMILES_CANONICAL CACTVS               3.341 NC(=N)c1ccc(cc1)[C@H]2[C@@H]3[C@H]([C@@H]4CCCN24)[C@@H](C5CC5)N(Cc6ccc7OCOc7c6)C3=O 
UIR SMILES           CACTVS               3.341 NC(=N)c1ccc(cc1)[CH]2[CH]3[CH]([CH]4CCCN24)[CH](C5CC5)N(Cc6ccc7OCOc7c6)C3=O 
UIR SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 c1cc(ccc1[C@H]2[C@@H]3[C@H]([C@H]4[N@@]2CCC4)[C@H](N(C3=O)Cc5ccc6c(c5)OCO6)C7CC7)C(=N)N 
UIR SMILES           "OpenEye OEToolkits" 1.5.0 c1cc(ccc1C2C3C(C4N2CCC4)C(N(C3=O)Cc5ccc6c(c5)OCO6)C7CC7)C(=N)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 
UIR "SYSTEMATIC NAME" ACDLabs              10.04 4-[(1R,3aS,4R,8aS,8bR)-2-(1,3-benzodioxol-5-ylmethyl)-1-cyclopropyl-3-oxodecahydropyrrolo[3,4-a]pyrrolizin-4-yl]benzenecarboximidamide                        
UIR "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 4-[(1R,3aS,4R,5S,8aS,8bR)-2-(1,3-benzodioxol-5-ylmethyl)-1-cyclopropyl-3-oxo-1,3a,4,6,7,8,8a,8b-octahydropyrrolo[3,4-a]pyrrolizin-4-yl]benzenecarboximidamide 
# 
