data_UIQ
# 
_chem_comp.id                                    UIQ 
_chem_comp.name                                  (1R,3AS,4R,8AS,8BR)-4-(2-BENZO[1,3]DIOXOL-5-YLMETHYL-1-ISOPROPYL-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 H32 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                        460.568 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     UIQ 
_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        1Y3U 
_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 
UIQ N1   N1   N 0 1 N N N -5.118 9.477  19.620 -5.385 -3.203 -0.851 N1   UIQ 1  
UIQ C3   C3   C 0 1 N N N -3.800 9.286  19.566 -4.755 -2.124 -0.483 C3   UIQ 2  
UIQ N2   N2   N 0 1 N N N -3.040 10.368 19.221 -5.433 -0.929 -0.389 N2   UIQ 3  
UIQ C4   C4   C 0 1 Y N N -3.230 8.028  19.933 -3.309 -2.183 -0.167 C4   UIQ 4  
UIQ C9   C9   C 0 1 Y N N -4.015 7.081  20.605 -2.620 -3.391 -0.261 C9   UIQ 5  
UIQ C8   C8   C 0 1 Y N N -3.434 5.883  21.071 -1.273 -3.439 0.035  C8   UIQ 6  
UIQ C7   C7   C 0 1 Y N N -2.065 5.647  20.917 -0.607 -2.292 0.425  C7   UIQ 7  
UIQ C6   C6   C 0 1 Y N N -1.285 6.611  20.237 -1.286 -1.091 0.526  C6   UIQ 8  
UIQ C5   C5   C 0 1 Y N N -1.846 7.788  19.752 -2.632 -1.029 0.227  C5   UIQ 9  
UIQ C10  C10  C 0 1 N N R -1.420 4.399  21.466 0.864  -2.351 0.747  C10  UIQ 10 
UIQ N11  N11  N 0 1 N N N -2.378 3.239  21.457 1.156  -1.482 1.897  N11  UIQ 11 
UIQ C12  C12  C 0 1 N N N -2.597 2.682  20.075 1.863  -2.367 2.893  C12  UIQ 12 
UIQ C13  C13  C 0 1 N N N -1.918 1.292  20.078 2.761  -1.390 3.689  C13  UIQ 13 
UIQ C14  C14  C 0 1 N N N -0.880 1.372  21.176 3.226  -0.389 2.607  C14  UIQ 14 
UIQ C15  C15  C 0 1 N N S -1.636 2.186  22.253 2.161  -0.472 1.502  C15  UIQ 15 
UIQ C16  C16  C 0 1 N N R -0.563 2.896  23.135 2.798  -0.959 0.193  C16  UIQ 16 
UIQ C17  C17  C 0 1 N N R -0.913 2.726  24.652 2.872  0.221  -0.800 C17  UIQ 17 
UIQ N19  N19  N 0 1 N N N -1.837 3.812  24.921 1.564  0.265  -1.463 N19  UIQ 18 
UIQ C20  C20  C 0 1 N N N -1.799 4.809  23.989 0.885  -0.904 -1.304 C20  UIQ 19 
UIQ O21  O21  O 0 1 N N N -2.603 5.775  23.894 -0.218 -1.148 -1.745 O21  UIQ 20 
UIQ C22  C22  C 0 1 N N S -0.807 4.407  22.871 1.708  -1.853 -0.464 C22  UIQ 21 
UIQ C23  C23  C 0 1 N N N -2.873 3.877  26.010 1.059  1.418  -2.213 C23  UIQ 22 
UIQ C24  C24  C 0 1 Y N N -2.397 4.542  27.299 0.407  2.389  -1.263 C24  UIQ 23 
UIQ C32  C32  C 0 1 Y N N -1.625 3.841  28.282 1.158  3.391  -0.678 C32  UIQ 24 
UIQ C31  C31  C 0 1 Y N N -1.264 4.413  29.525 0.564  4.285  0.194  C31  UIQ 25 
UIQ C30  C30  C 0 1 Y N N -1.692 5.728  29.741 -0.786 4.178  0.483  C30  UIQ 26 
UIQ O29  O29  O 0 1 N N N -1.211 6.675  30.620 -1.600 4.916  1.293  O29  UIQ 27 
UIQ C28  C28  C 0 1 N N N -2.231 7.731  30.585 -2.768 4.102  1.510  C28  UIQ 28 
UIQ O27  O27  O 0 1 N N N -3.142 7.476  29.471 -2.831 3.274  0.333  O27  UIQ 29 
UIQ C26  C26  C 0 1 Y N N -2.464 6.441  28.791 -1.543 3.168  -0.107 C26  UIQ 30 
UIQ C25  C25  C 0 1 Y N N -2.821 5.862  27.563 -0.942 2.280  -0.984 C25  UIQ 31 
UIQ C18  C18  C 0 1 N N N 0.302  2.634  25.603 3.978  -0.022 -1.829 C18  UIQ 32 
UIQ C41  C41  C 0 1 N N N 1.081  1.352  25.409 5.337  -0.022 -1.126 C41  UIQ 33 
UIQ C42  C42  C 0 1 N N N 1.291  3.786  25.456 3.754  -1.375 -2.508 C42  UIQ 34 
UIQ HN1  HN1  H 0 1 N N N -5.496 10.424 19.579 -6.332 -3.165 -1.059 HN1  UIQ 35 
UIQ HN21 1HN2 H 0 0 N N N -3.248 11.147 19.846 -6.380 -0.891 -0.596 HN21 UIQ 36 
UIQ HN22 2HN2 H 0 0 N N N -2.031 10.222 19.180 -4.964 -0.125 -0.115 HN22 UIQ 37 
UIQ H9   H9   H 0 1 N N N -5.088 7.278  20.767 -3.140 -4.288 -0.566 H9   UIQ 38 
UIQ H8   H8   H 0 1 N N N -4.059 5.119  21.563 -0.738 -4.375 -0.038 H8   UIQ 39 
UIQ H6   H6   H 0 1 N N N -0.207 6.440  20.080 -0.761 -0.198 0.832  H6   UIQ 40 
UIQ H5   H5   H 0 1 N N N -1.204 8.519  19.232 -3.160 -0.090 0.303  H5   UIQ 41 
UIQ H10  H10  H 0 1 N N N -0.561 4.319  20.760 1.149  -3.377 0.980  H10  UIQ 42 
UIQ H121 1H12 H 0 0 N N N -2.241 3.353  19.259 2.469  -3.115 2.382  H121 UIQ 43 
UIQ H122 2H12 H 0 0 N N N -3.668 2.657  19.766 1.139  -2.847 3.553  H122 UIQ 44 
UIQ H131 1H13 H 0 0 N N N -1.507 0.986  19.088 3.613  -1.914 4.122  H131 UIQ 45 
UIQ H132 2H13 H 0 0 N N N -2.629 0.440  20.188 2.186  -0.881 4.463  H132 UIQ 46 
UIQ H141 1H14 H 0 0 N N N 0.107  1.790  20.869 4.201  -0.681 2.215  H141 UIQ 47 
UIQ H142 2H14 H 0 0 N N N -0.472 0.392  21.518 3.269  0.620  3.017  H142 UIQ 48 
UIQ H15  H15  H 0 1 N N N -2.309 1.573  22.897 1.687  0.499  1.357  H15  UIQ 49 
UIQ H16  H16  H 0 1 N N N 0.457  2.505  22.912 3.753  -1.465 0.337  H16  UIQ 50 
UIQ H17  H17  H 0 1 N N N -1.377 1.734  24.861 3.054  1.153  -0.265 H17  UIQ 51 
UIQ H22  H22  H 0 1 N N N 0.058  5.110  22.895 2.121  -2.675 -1.048 H22  UIQ 52 
UIQ H231 1H23 H 0 0 N N N -3.275 2.859  26.224 1.887  1.910  -2.724 H231 UIQ 53 
UIQ H232 2H23 H 0 0 N N N -3.798 4.374  25.636 0.328  1.082  -2.948 H232 UIQ 54 
UIQ H32  H32  H 0 1 N N N -1.292 2.811  28.072 2.212  3.476  -0.901 H32  UIQ 55 
UIQ H31  H31  H 0 1 N N N -0.681 3.864  30.284 1.154  5.066  0.651  H31  UIQ 56 
UIQ H281 1H28 H 0 0 N N N -1.784 8.752  30.543 -2.648 3.490  2.403  H281 UIQ 57 
UIQ H282 2H28 H 0 0 N N N -2.767 7.835  31.557 -3.659 4.725  1.588  H282 UIQ 58 
UIQ H25  H25  H 0 1 N N N -3.417 6.428  26.827 -1.528 1.499  -1.447 H25  UIQ 59 
UIQ H18  H18  H 0 1 N N N -0.155 2.674  26.619 3.957  0.769  -2.579 H18  UIQ 60 
UIQ H411 1H41 H 0 0 N N N 1.390  1.224  24.345 6.122  -0.228 -1.854 H411 UIQ 61 
UIQ H412 2H41 H 0 0 N N N 1.958  1.286  26.095 5.510  0.952  -0.670 H412 UIQ 62 
UIQ H413 3H41 H 0 0 N N N 0.421  0.459  25.510 5.347  -0.792 -0.355 H413 UIQ 63 
UIQ H421 1H42 H 0 0 N N N 0.772  4.766  25.576 3.775  -2.165 -1.758 H421 UIQ 64 
UIQ H422 2H42 H 0 0 N N N 2.168  3.720  26.142 2.786  -1.374 -3.009 H422 UIQ 65 
UIQ H423 3H42 H 0 0 N N N 1.628  3.881  24.397 4.542  -1.548 -3.241 H423 UIQ 66 
# 
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 
UIQ N1  C3   DOUB N Z 1  
UIQ N1  HN1  SING N N 2  
UIQ C3  N2   SING N N 3  
UIQ C3  C4   SING N N 4  
UIQ N2  HN21 SING N N 5  
UIQ N2  HN22 SING N N 6  
UIQ C4  C9   DOUB Y N 7  
UIQ C4  C5   SING Y N 8  
UIQ C9  C8   SING Y N 9  
UIQ C9  H9   SING N N 10 
UIQ C8  C7   DOUB Y N 11 
UIQ C8  H8   SING N N 12 
UIQ C7  C6   SING Y N 13 
UIQ C7  C10  SING N N 14 
UIQ C6  C5   DOUB Y N 15 
UIQ C6  H6   SING N N 16 
UIQ C5  H5   SING N N 17 
UIQ C10 N11  SING N N 18 
UIQ C10 C22  SING N N 19 
UIQ C10 H10  SING N N 20 
UIQ N11 C12  SING N N 21 
UIQ N11 C15  SING N N 22 
UIQ C12 C13  SING N N 23 
UIQ C12 H121 SING N N 24 
UIQ C12 H122 SING N N 25 
UIQ C13 C14  SING N N 26 
UIQ C13 H131 SING N N 27 
UIQ C13 H132 SING N N 28 
UIQ C14 C15  SING N N 29 
UIQ C14 H141 SING N N 30 
UIQ C14 H142 SING N N 31 
UIQ C15 C16  SING N N 32 
UIQ C15 H15  SING N N 33 
UIQ C16 C17  SING N N 34 
UIQ C16 C22  SING N N 35 
UIQ C16 H16  SING N N 36 
UIQ C17 N19  SING N N 37 
UIQ C17 C18  SING N N 38 
UIQ C17 H17  SING N N 39 
UIQ N19 C20  SING N N 40 
UIQ N19 C23  SING N N 41 
UIQ C20 O21  DOUB N N 42 
UIQ C20 C22  SING N N 43 
UIQ C22 H22  SING N N 44 
UIQ C23 C24  SING N N 45 
UIQ C23 H231 SING N N 46 
UIQ C23 H232 SING N N 47 
UIQ C24 C32  DOUB Y N 48 
UIQ C24 C25  SING Y N 49 
UIQ C32 C31  SING Y N 50 
UIQ C32 H32  SING N N 51 
UIQ C31 C30  DOUB Y N 52 
UIQ C31 H31  SING N N 53 
UIQ C30 O29  SING N N 54 
UIQ C30 C26  SING Y N 55 
UIQ O29 C28  SING N N 56 
UIQ C28 O27  SING N N 57 
UIQ C28 H281 SING N N 58 
UIQ C28 H282 SING N N 59 
UIQ O27 C26  SING N N 60 
UIQ C26 C25  DOUB Y N 61 
UIQ C25 H25  SING N N 62 
UIQ C18 C41  SING N N 63 
UIQ C18 C42  SING N N 64 
UIQ C18 H18  SING N N 65 
UIQ C41 H411 SING N N 66 
UIQ C41 H412 SING N N 67 
UIQ C41 H413 SING N N 68 
UIQ C42 H421 SING N N 69 
UIQ C42 H422 SING N N 70 
UIQ C42 H423 SING N N 71 
# 
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 
UIQ SMILES           ACDLabs              10.04 O=C1N(C(C(C)C)C4C1C(c2ccc(C(=[N@H])N)cc2)N3CCCC34)Cc5ccc6OCOc6c5 
UIQ InChI            InChI                1.02b 
InChI=1/C27H32N4O3/c1-15(2)24-22-19-4-3-11-30(19)25(17-6-8-18(9-7-17)26(28)29)23(22)27(32)31(24)13-16-5-10-20-21(12-16)34-14-33-20/h5-10,12,15,19,22-25H,3-4,11,13-14H2,1-2H3,(H3,28,29)/t19-,22-,23-,24+,25-/m0/s1/f/h28H,29H2/b28-26- 
UIQ InChIKey         InChI                1.02b TZROHICTGLJYJF-CCTADIIJDA 
UIQ SMILES_CANONICAL CACTVS               3.341 CC(C)[C@@H]1[C@H]2[C@@H]3CCCN3[C@H]([C@H]2C(=O)N1Cc4ccc5OCOc5c4)c6ccc(cc6)C(N)=N 
UIQ SMILES           CACTVS               3.341 CC(C)[CH]1[CH]2[CH]3CCCN3[CH]([CH]2C(=O)N1Cc4ccc5OCOc5c4)c6ccc(cc6)C(N)=N 
UIQ SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 [H]/N=C(/c1ccc(cc1)[C@H]2[C@@H]3[C@H]([C@H]4[N@@]2CCC4)[C@H](N(C3=O)Cc5ccc6c(c5)OCO6)C(C)C)\N 
UIQ SMILES           "OpenEye OEToolkits" 1.5.0 [H]N=C(c1ccc(cc1)C2C3C(C4N2CCC4)C(N(C3=O)Cc5ccc6c(c5)OCO6)C(C)C)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 
UIQ "SYSTEMATIC NAME" ACDLabs              10.04 4-[(1R,3aS,4R,8aS,8bR)-2-(1,3-benzodioxol-5-ylmethyl)-1-(1-methylethyl)-3-oxodecahydropyrrolo[3,4-a]pyrrolizin-4-yl]benzenecarboximidamide                    
UIQ "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 4-[(1R,3aS,4R,5S,8aS,8bR)-2-(1,3-benzodioxol-5-ylmethyl)-3-oxo-1-propan-2-yl-1,3a,4,6,7,8,8a,8b-octahydropyrrolo[4,3-a]pyrrolizin-4-yl]benzenecarboximidamide 
# 
