data_UIP
# 
_chem_comp.id                                    UIP 
_chem_comp.name                                  (1R,3AS,4R,8AS,8BR)-4-(2-BENZO[1,3]DIOXOL-5-YLMETHYL-1-ETHYL-3-OXO-DECAHYDRO-PYRROLO[3,4-A]PYRROLIZIN-4-YL)-BENZAMIDINE 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C26 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                     2003-06-26 
_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                        446.541 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     UIP 
_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        ? 
_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 
UIP N1   N1   N 0 1 N N N -5.138 9.459  19.574 -0.886 -0.115 -5.147 N1   UIP 1  
UIP C3   C3   C 0 1 N N N -3.814 9.275  19.599 -1.952 -0.506 -4.509 C3   UIP 2  
UIP N2   N2   N 0 1 N N N -3.059 10.371 19.267 -2.967 -1.143 -5.189 N2   UIP 3  
UIP C4   C4   C 0 1 Y N N -3.217 8.101  20.152 -2.073 -0.267 -3.053 C4   UIP 4  
UIP C9   C9   C 0 1 Y N N -3.974 7.129  20.816 -1.047 0.376  -2.362 C9   UIP 5  
UIP C8   C8   C 0 1 Y N N -3.373 5.925  21.208 -1.165 0.597  -1.005 C8   UIP 6  
UIP C7   C7   C 0 1 Y N N -2.019 5.672  20.989 -2.299 0.181  -0.330 C7   UIP 7  
UIP C6   C6   C 0 1 Y N N -1.257 6.647  20.311 -3.317 -0.463 -1.009 C6   UIP 8  
UIP C5   C5   C 0 1 Y N N -1.858 7.830  19.914 -3.213 -0.684 -2.367 C5   UIP 9  
UIP C10  C10  C 0 1 N N R -1.319 4.461  21.531 -2.422 0.425  1.151  C10  UIP 10 
UIP N11  N11  N 0 1 N N N -2.155 3.223  21.435 -1.713 1.662  1.511  N11  UIP 11 
UIP C12  C12  C 0 1 N N N -2.333 2.705  20.041 -2.731 2.503  2.241  C12  UIP 12 
UIP C13  C13  C 0 1 N N N -1.427 1.456  19.927 -1.879 3.376  3.193  C13  UIP 13 
UIP C14  C14  C 0 1 N N N -0.475 1.533  21.095 -0.754 2.411  3.633  C14  UIP 14 
UIP C15  C15  C 0 1 N N S -1.344 2.188  22.195 -0.677 1.355  2.519  C15  UIP 15 
UIP C16  C16  C 0 1 N N R -0.385 2.954  23.151 -0.999 -0.033 3.088  C16  UIP 16 
UIP C17  C17  C 0 1 N N R -0.726 2.720  24.658 0.297  -0.868 3.144  C17  UIP 17 
UIP N19  N19  N 0 1 N N N -1.707 3.739  24.953 0.447  -1.460 1.809  N19  UIP 18 
UIP C20  C20  C 0 1 N N N -1.676 4.794  24.076 -0.722 -1.421 1.113  C20  UIP 19 
UIP O21  O21  O 0 1 N N N -2.555 5.703  24.037 -0.890 -1.839 -0.012 O21  UIP 20 
UIP C22  C22  C 0 1 N N S -0.702 4.453  22.931 -1.784 -0.748 1.952  C22  UIP 21 
UIP C23  C23  C 0 1 N N N -2.613 3.911  26.133 1.695  -2.031 1.297  C23  UIP 22 
UIP C24  C24  C 0 1 Y N N -1.983 4.573  27.352 2.419  -0.999 0.472  C24  UIP 23 
UIP C32  C32  C 0 1 Y N N -1.129 3.832  28.233 3.326  -0.147 1.075  C32  UIP 24 
UIP C31  C31  C 0 1 Y N N -0.633 4.377  29.440 3.993  0.801  0.322  C31  UIP 25 
UIP C30  C30  C 0 1 Y N N -1.028 5.698  29.723 3.754  0.900  -1.038 C30  UIP 26 
UIP O29  O29  O 0 1 N N N -0.455 6.593  30.612 4.269  1.732  -1.989 O29  UIP 27 
UIP C28  C28  C 0 1 N N N -1.377 7.737  30.609 3.363  1.648  -3.105 C28  UIP 28 
UIP O27  O27  O 0 1 N N N -2.396 7.539  29.579 2.782  0.337  -2.976 O27  UIP 29 
UIP C26  C26  C 0 1 Y N N -1.875 6.443  28.869 2.840  0.042  -1.645 C26  UIP 30 
UIP C25  C25  C 0 1 Y N N -2.362 5.891  27.669 2.179  -0.909 -0.885 C25  UIP 31 
UIP C18  C18  C 0 1 N N N 0.514  2.752  25.586 0.172  -1.969 4.199  C18  UIP 32 
UIP C42  C42  C 0 1 N N N 1.336  1.470  25.552 1.513  -2.693 4.342  C42  UIP 33 
UIP HN1  HN1  H 0 1 N N N -5.521 10.404 19.593 -0.807 -0.272 -6.101 HN1  UIP 34 
UIP HN21 1HN2 H 0 0 N N N -2.048 10.230 19.286 -2.888 -1.300 -6.143 HN21 UIP 35 
UIP HN22 2HN2 H 0 0 N N N -3.312 11.162 19.858 -3.761 -1.434 -4.714 HN22 UIP 36 
UIP H9   H9   H 0 1 N N N -5.040 7.311  21.029 -0.161 0.702  -2.888 H9   UIP 37 
UIP H8   H8   H 0 1 N N N -3.984 5.152  21.704 -0.372 1.096  -0.469 H8   UIP 38 
UIP H6   H6   H 0 1 N N N -0.188 6.484  20.090 -4.200 -0.786 -0.477 H6   UIP 39 
UIP H5   H5   H 0 1 N N N -1.236 8.577  19.393 -4.011 -1.184 -2.897 H5   UIP 40 
UIP H10  H10  H 0 1 N N N -0.443 4.496  20.841 -3.474 0.510  1.424  H10  UIP 41 
UIP H121 1H12 H 0 0 N N N -3.397 2.507  19.773 -3.415 1.872  2.809  H121 UIP 42 
UIP H122 2H12 H 0 0 N N N -2.135 3.470  19.254 -3.281 3.128  1.537  H122 UIP 43 
UIP H131 1H13 H 0 0 N N N -1.993 0.496  19.874 -2.468 3.698  4.052  H131 UIP 44 
UIP H132 2H13 H 0 0 N N N -0.916 1.363  18.940 -1.466 4.235  2.664  H132 UIP 45 
UIP H141 1H14 H 0 0 N N N -0.007 0.562  21.383 -1.008 1.941  4.583  H141 UIP 46 
UIP H142 2H14 H 0 0 N N N 0.485  2.057  20.882 0.192  2.945  3.714  H142 UIP 47 
UIP H15  H15  H 0 1 N N N -1.965 1.463  22.771 0.311  1.358  2.060  H15  UIP 48 
UIP H16  H16  H 0 1 N N N 0.660  2.625  22.942 -1.534 0.001  4.037  H16  UIP 49 
UIP H17  H17  H 0 1 N N N -1.123 1.695  24.846 1.149  -0.227 3.369  H17  UIP 50 
UIP H22  H22  H 0 1 N N N 0.129  5.195  22.961 -2.529 -1.452 2.322  H22  UIP 51 
UIP H231 1H23 H 0 0 N N N -3.532 4.464  25.830 1.469  -2.899 0.677  H231 UIP 52 
UIP H232 2H23 H 0 0 N N N -3.058 2.929  26.418 2.325  -2.336 2.133  H232 UIP 53 
UIP H32  H32  H 0 1 N N N -0.841 2.799  27.971 3.514  -0.223 2.136  H32  UIP 54 
UIP H31  H31  H 0 1 N N N 0.022  3.806  30.119 4.701  1.465  0.795  H31  UIP 55 
UIP H281 1H28 H 0 0 N N N -1.823 7.920  31.613 3.905  1.736  -4.046 H281 UIP 56 
UIP H282 2H28 H 0 0 N N N -0.842 8.708  30.492 2.593  2.416  -3.032 H282 UIP 57 
UIP H25  H25  H 0 1 N N N -3.018 6.471  26.999 1.473  -1.579 -1.354 H25  UIP 58 
UIP H181 1H18 H 0 0 N N N 1.153  3.636  25.357 -0.593 -2.682 3.892  H181 UIP 59 
UIP H182 2H18 H 0 0 N N N 0.217  3.001  26.631 -0.105 -1.526 5.155  H182 UIP 60 
UIP H421 1H42 H 0 0 N N N 2.228  1.493  26.219 1.467  -3.378 5.188  H421 UIP 61 
UIP H422 2H42 H 0 0 N N N 0.696  0.585  25.780 1.723  -3.253 3.431  H422 UIP 62 
UIP H423 3H42 H 0 0 N N N 1.632  1.220  24.506 2.304  -1.962 4.509  H423 UIP 63 
# 
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 
UIP N1  C3   DOUB N N 1  
UIP N1  HN1  SING N N 2  
UIP C3  N2   SING N N 3  
UIP C3  C4   SING N N 4  
UIP N2  HN21 SING N N 5  
UIP N2  HN22 SING N N 6  
UIP C4  C9   DOUB Y N 7  
UIP C4  C5   SING Y N 8  
UIP C9  C8   SING Y N 9  
UIP C9  H9   SING N N 10 
UIP C8  C7   DOUB Y N 11 
UIP C8  H8   SING N N 12 
UIP C7  C6   SING Y N 13 
UIP C7  C10  SING N N 14 
UIP C6  C5   DOUB Y N 15 
UIP C6  H6   SING N N 16 
UIP C5  H5   SING N N 17 
UIP C10 N11  SING N N 18 
UIP C10 C22  SING N N 19 
UIP C10 H10  SING N N 20 
UIP N11 C12  SING N N 21 
UIP N11 C15  SING N N 22 
UIP C12 C13  SING N N 23 
UIP C12 H121 SING N N 24 
UIP C12 H122 SING N N 25 
UIP C13 C14  SING N N 26 
UIP C13 H131 SING N N 27 
UIP C13 H132 SING N N 28 
UIP C14 C15  SING N N 29 
UIP C14 H141 SING N N 30 
UIP C14 H142 SING N N 31 
UIP C15 C16  SING N N 32 
UIP C15 H15  SING N N 33 
UIP C16 C17  SING N N 34 
UIP C16 C22  SING N N 35 
UIP C16 H16  SING N N 36 
UIP C17 N19  SING N N 37 
UIP C17 C18  SING N N 38 
UIP C17 H17  SING N N 39 
UIP N19 C20  SING N N 40 
UIP N19 C23  SING N N 41 
UIP C20 O21  DOUB N N 42 
UIP C20 C22  SING N N 43 
UIP C22 H22  SING N N 44 
UIP C23 C24  SING N N 45 
UIP C23 H231 SING N N 46 
UIP C23 H232 SING N N 47 
UIP C24 C32  DOUB Y N 48 
UIP C24 C25  SING Y N 49 
UIP C32 C31  SING Y N 50 
UIP C32 H32  SING N N 51 
UIP C31 C30  DOUB Y N 52 
UIP C31 H31  SING N N 53 
UIP C30 O29  SING N N 54 
UIP C30 C26  SING Y N 55 
UIP O29 C28  SING N N 56 
UIP C28 O27  SING N N 57 
UIP C28 H281 SING N N 58 
UIP C28 H282 SING N N 59 
UIP O27 C26  SING N N 60 
UIP C26 C25  DOUB Y N 61 
UIP C25 H25  SING N N 62 
UIP C18 C42  SING N N 63 
UIP C18 H181 SING N N 64 
UIP C18 H182 SING N N 65 
UIP C42 H421 SING N N 66 
UIP C42 H422 SING N N 67 
UIP C42 H423 SING N N 68 
# 
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 
UIP SMILES           ACDLabs              10.04 O=C1N(C(CC)C4C1C(c2ccc(C(=[N@H])N)cc2)N3CCCC34)Cc5ccc6OCOc6c5 
UIP InChI            InChI                1.02b 
InChI=1/C26H30N4O3/c1-2-18-22-19-4-3-11-29(19)24(16-6-8-17(9-7-16)25(27)28)23(22)26(31)30(18)13-15-5-10-20-21(12-15)33-14-32-20/h5-10,12,18-19,22-24H,2-4,11,13-14H2,1H3,(H3,27,28)/t18-,19+,22+,23+,24+/m1/s1/f/h27H,28H2/b27-25- 
UIP InChIKey         InChI                1.02b RCAUWWFTOCHSJH-MUJZYJEIDR 
UIP SMILES_CANONICAL CACTVS               3.341 CC[C@@H]1[C@H]2[C@@H]3CCCN3[C@H]([C@H]2C(=O)N1Cc4ccc5OCOc5c4)c6ccc(cc6)C(N)=N 
UIP SMILES           CACTVS               3.341 CC[CH]1[CH]2[CH]3CCCN3[CH]([CH]2C(=O)N1Cc4ccc5OCOc5c4)c6ccc(cc6)C(N)=N 
UIP SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 CC[C@@H]1[C@H]2[C@@H]3CCC[N@@]3[C@H]([C@H]2C(=O)N1Cc4ccc5c(c4)OCO5)c6ccc(cc6)C(=N)N 
UIP SMILES           "OpenEye OEToolkits" 1.5.0 CCC1C2C3CCCN3C(C2C(=O)N1Cc4ccc5c(c4)OCO5)c6ccc(cc6)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 
UIP "SYSTEMATIC NAME" ACDLabs              10.04 4-[(1R,3aS,4R,8aS,8bR)-2-(1,3-benzodioxol-5-ylmethyl)-1-ethyl-3-oxodecahydropyrrolo[3,4-a]pyrrolizin-4-yl]benzenecarboximidamide                        
UIP "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 4-[(1R,3aS,4R,5S,8aS,8bR)-2-(1,3-benzodioxol-5-ylmethyl)-1-ethyl-3-oxo-1,3a,4,6,7,8,8a,8b-octahydropyrrolo[3,4-a]pyrrolizin-4-yl]benzenecarboximidamide 
# 
