data_F25
# 
_chem_comp.id                                    F25 
_chem_comp.name                                  4-(1R,3AS,4R,8AS,8BR)-[1-DIFLUOROMETHYL-2-(4-FLUOROBENZYL)-3-OXODECAHYDROPYRROLO[3,4-A]PYRROLIZIN-4-YL]BENZAMIDINE 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C24 H27 F3 N4 O" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         ? 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2006-05-17 
_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                        444.493 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     F25 
_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                  EBI 
# 
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 
F25 O21  O21  O 0 1 N N N 16.864 -12.817 22.565 0.891  -0.530 1.649  O21  F25 1  
F25 C20  C20  C 0 1 N N N 17.504 -12.527 21.609 -0.230 -0.786 1.263  C20  F25 2  
F25 N19  N19  N 0 1 N N N 18.548 -13.281 21.236 -1.288 0.057  1.344  N19  F25 3  
F25 C23  C23  C 0 1 N N N 18.959 -14.528 21.874 -1.223 1.406  1.911  C23  F25 4  
F25 C24  C24  C 0 1 Y N N 19.866 -14.279 23.046 -1.033 2.409  0.802  C24  F25 5  
F25 C32  C32  C 0 1 Y N N 21.252 -14.356 22.899 -2.131 3.032  0.240  C32  F25 6  
F25 C31  C31  C 0 1 Y N N 22.104 -14.121 23.965 -1.958 3.952  -0.778 C31  F25 7  
F25 C30  C30  C 0 1 Y N N 21.567 -13.799 25.198 -0.685 4.248  -1.233 C30  F25 8  
F25 F29  F29  F 0 1 N N N 22.366 -13.566 26.257 -0.514 5.147  -2.227 F29  F25 9  
F25 C26  C26  C 0 1 Y N N 20.191 -13.740 25.373 0.414  3.624  -0.668 C26  F25 10 
F25 C25  C25  C 0 1 Y N N 19.353 -13.974 24.304 0.239  2.709  0.353  C25  F25 11 
F25 C17  C17  C 0 1 N N S 19.115 -12.873 19.957 -2.506 -0.555 0.802  C17  F25 12 
F25 C16  C16  C 0 1 N N R 18.101 -11.830 19.441 -2.027 -1.748 -0.054 C16  F25 13 
F25 C15  C15  C 0 1 N N S 17.126 -12.382 18.415 -1.643 -1.259 -1.459 C15  F25 14 
F25 N11  N11  N 0 1 N N N 15.805 -12.324 19.069 -0.348 -1.862 -1.798 N11  F25 15 
F25 C12  C12  C 0 1 N N N 14.758 -12.093 18.053 -0.723 -3.108 -2.621 C12  F25 16 
F25 C13  C13  C 0 1 N N N 15.507 -11.904 16.745 -1.933 -2.633 -3.462 C13  F25 17 
F25 C14  C14  C 0 1 N N N 16.962 -11.631 17.105 -2.697 -1.715 -2.480 C14  F25 18 
F25 C10  C10  C 0 1 N N R 15.898 -11.223 20.056 0.271  -2.394 -0.574 C10  F25 19 
F25 C7   C7   C 0 1 Y N N 14.755 -11.193 21.013 1.611  -1.741 -0.356 C7   F25 20 
F25 C8   C8   C 0 1 Y N N 13.999 -12.307 21.323 2.673  -2.486 0.122  C8   F25 21 
F25 C9   C9   C 0 1 Y N N 12.954 -12.212 22.237 3.903  -1.888 0.322  C9   F25 22 
F25 C4   C4   C 0 1 Y N N 12.625 -10.995 22.823 4.072  -0.545 0.043  C4   F25 23 
F25 C5   C5   C 0 1 Y N N 13.374 -9.890  22.515 3.008  0.202  -0.430 C5   F25 24 
F25 C6   C6   C 0 1 Y N N 14.429 -9.988  21.612 1.779  -0.398 -0.634 C6   F25 25 
F25 C3   C3   C 0 1 N N N 11.479 -10.930 23.782 5.413  0.108  0.260  C3   F25 26 
F25 N1   N1   N 0 1 N N N 10.700 -11.988 24.045 6.114  -0.569 1.359  N1   F25 27 
F25 N2   N2   N 0 1 N N N 11.197 -9.819  24.440 5.219  1.524  0.600  N2   F25 28 
F25 C22  C22  C 0 1 N N S 17.284 -11.392 20.653 -0.658 -2.078 0.607  C22  F25 29 
F25 C18  C18  C 0 1 N N N 20.481 -12.237 20.126 -3.403 -1.048 1.939  C18  F25 30 
F25 F33  F33  F 0 1 N N N 20.958 -11.879 18.894 -3.854 0.047  2.685  F33  F25 31 
F25 F32  F32  F 0 1 N N N 20.445 -11.085 20.857 -4.501 -1.731 1.404  F32  F25 32 
F25 H231 1H23 H 0 0 N N N 19.509 -15.128 21.134 -2.151 1.622  2.441  H231 F25 33 
F25 H232 2H23 H 0 0 N N N 18.062 -15.057 22.228 -0.385 1.469  2.605  H232 F25 34 
F25 H25  H25  H 0 1 N N N 21.668 -14.604 21.934 -3.125 2.801  0.595  H25  F25 35 
F25 H26  H26  H 0 1 N N N 23.174 -14.188 23.835 -2.816 4.438  -1.218 H26  F25 36 
F25 H28  H28  H 0 1 N N N 19.778 -13.511 26.344 1.408  3.854  -1.022 H28  F25 37 
F25 H29  H29  H 0 1 N N N 18.283 -13.920 24.444 1.096  2.221  0.794  H29  F25 38 
F25 H17  H17  H 0 1 N N N 19.266 -13.722 19.275 -3.044 0.162  0.181  H17  F25 39 
F25 H16  H16  H 0 1 N N N 18.662 -11.019 18.952 -2.724 -2.585 -0.062 H16  F25 40 
F25 H15  H15  H 0 1 N N N 17.524 -13.368 18.133 -1.546 -0.174 -1.471 H15  F25 41 
F25 H121 1H12 H 0 0 N N N 14.136 -11.220 18.298 -1.008 -3.938 -1.975 H121 F25 42 
F25 H122 2H12 H 0 0 N N N 14.073 -12.951 17.993 0.105  -3.392 -3.270 H122 F25 43 
F25 H131 1H13 H 0 0 N N N 15.082 -11.071 16.166 -2.552 -3.480 -3.759 H131 F25 44 
F25 H132 2H13 H 0 0 N N N 15.430 -12.810 16.125 -1.601 -2.072 -4.335 H132 F25 45 
F25 H142 2H14 H 0 0 N N N 17.159 -10.555 17.223 -3.109 -0.855 -3.008 H142 F25 46 
F25 H141 1H14 H 0 0 N N N 17.670 -11.954 16.327 -3.491 -2.271 -1.981 H141 F25 47 
F25 H10  H10  H 0 1 N N N 15.798 -10.221 19.613 0.397  -3.473 -0.664 H10  F25 48 
F25 H8   H8   H 0 1 N N N 14.220 -13.255 20.854 2.542  -3.536 0.340  H8   F25 49 
F25 H9   H9   H 0 1 N N N 12.390 -13.096 22.495 4.733  -2.470 0.695  H9   F25 50 
F25 H5   H5   H 0 1 N N N 13.145 -8.940  22.974 3.140  1.251  -0.648 H5   F25 51 
F25 H6   H6   H 0 1 N N N 15.005 -9.106  21.374 0.950  0.184  -1.007 H6   F25 52 
F25 H33  3H3  H 0 1 N N N 12.004 -11.069 22.808 6.006  0.031  -0.652 H33  F25 53 
F25 H12  H12  H 0 1 N N N 11.171 -12.598 24.682 5.531  -0.473 2.177  H12  F25 54 
F25 HN1  HN1  H 0 1 N N N 10.506 -12.479 23.196 6.133  -1.551 1.130  HN1  F25 55 
F25 H23  H23  H 0 1 N N N 11.924 -9.149  24.289 6.138  1.918  0.736  H23  F25 56 
F25 HN2  HN2  H 0 1 N N N 11.126 -10.019 25.417 4.831  1.968  -0.218 HN2  F25 57 
F25 H22  H22  H 0 1 N N N 17.513 -10.465 21.200 -0.724 -2.903 1.317  H22  F25 58 
F25 H18  H18  H 0 1 N N N 21.108 -12.980 20.641 -2.837 -1.719 2.584  H18  F25 59 
# 
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 
F25 O21 C20  DOUB N N 1  
F25 C20 N19  SING N N 2  
F25 C20 C22  SING N N 3  
F25 N19 C23  SING N N 4  
F25 N19 C17  SING N N 5  
F25 C23 C24  SING N N 6  
F25 C23 H231 SING N N 7  
F25 C23 H232 SING N N 8  
F25 C24 C32  DOUB Y N 9  
F25 C24 C25  SING Y N 10 
F25 C32 C31  SING Y N 11 
F25 C32 H25  SING N N 12 
F25 C31 C30  DOUB Y N 13 
F25 C31 H26  SING N N 14 
F25 C30 F29  SING N N 15 
F25 C30 C26  SING Y N 16 
F25 C26 C25  DOUB Y N 17 
F25 C26 H28  SING N N 18 
F25 C25 H29  SING N N 19 
F25 C17 C16  SING N N 20 
F25 C17 C18  SING N N 21 
F25 C17 H17  SING N N 22 
F25 C16 C15  SING N N 23 
F25 C16 C22  SING N N 24 
F25 C16 H16  SING N N 25 
F25 C15 N11  SING N N 26 
F25 C15 C14  SING N N 27 
F25 C15 H15  SING N N 28 
F25 N11 C12  SING N N 29 
F25 N11 C10  SING N N 30 
F25 C12 C13  SING N N 31 
F25 C12 H121 SING N N 32 
F25 C12 H122 SING N N 33 
F25 C13 C14  SING N N 34 
F25 C13 H131 SING N N 35 
F25 C13 H132 SING N N 36 
F25 C14 H142 SING N N 37 
F25 C14 H141 SING N N 38 
F25 C10 C7   SING N N 39 
F25 C10 C22  SING N N 40 
F25 C10 H10  SING N N 41 
F25 C7  C8   DOUB Y N 42 
F25 C7  C6   SING Y N 43 
F25 C8  C9   SING Y N 44 
F25 C8  H8   SING N N 45 
F25 C9  C4   DOUB Y N 46 
F25 C9  H9   SING N N 47 
F25 C4  C5   SING Y N 48 
F25 C4  C3   SING N N 49 
F25 C5  C6   DOUB Y N 50 
F25 C5  H5   SING N N 51 
F25 C6  H6   SING N N 52 
F25 C3  N1   SING N N 53 
F25 C3  N2   SING N N 54 
F25 C3  H33  SING N N 55 
F25 N1  H12  SING N N 56 
F25 N1  HN1  SING N N 57 
F25 N2  H23  SING N N 58 
F25 N2  HN2  SING N N 59 
F25 C22 H22  SING N N 60 
F25 C18 F33  SING N N 61 
F25 C18 F32  SING N N 62 
F25 C18 H18  SING N N 63 
# 
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 
F25 SMILES           ACDLabs              10.04 Fc1ccc(cc1)CN2C(=O)C5C(C2C(F)F)C3N(CCC3)C5c4ccc(cc4)C(N)N                                                                                                                            
F25 InChI            InChI                1.02b InChI=1/C24H27F3N4O/c25-16-9-3-13(4-10-16)12-31-21(22(26)27)18-17-2-1-11-30(17)20(19(18)24(31)32)14-5-7-15(8-6-14)23(28)29/h3-10,17-23H,1-2,11-12,28-29H2/t17-,18-,19-,20-,21-/m0/s1 
F25 InChIKey         InChI                1.02b VPNYXOTTXAXSIH-SXYSDOLCBW                                                                                                                                                            
F25 SMILES_CANONICAL CACTVS               3.341 NC(N)c1ccc(cc1)[C@H]2[C@@H]3[C@H]([C@@H]4CCCN24)[C@@H](C(F)F)N(Cc5ccc(F)cc5)C3=O                                                                                                     
F25 SMILES           CACTVS               3.341 NC(N)c1ccc(cc1)[CH]2[CH]3[CH]([CH]4CCCN24)[CH](C(F)F)N(Cc5ccc(F)cc5)C3=O                                                                                                             
F25 SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 c1cc(ccc1CN2[C@@H]([C@H]3[C@@H]4CCC[N@@]4[C@H]([C@H]3C2=O)c5ccc(cc5)C(N)N)C(F)F)F                                                                                                    
F25 SMILES           "OpenEye OEToolkits" 1.5.0 c1cc(ccc1CN2C(C3C4CCCN4C(C3C2=O)c5ccc(cc5)C(N)N)C(F)F)F                                                                                                                              
# 
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 
F25 "SYSTEMATIC NAME" ACDLabs              10.04 (1S,3aS,4R,8aS,8bR)-4-[4-(diaminomethyl)phenyl]-1-(difluoromethyl)-2-(4-fluorobenzyl)octahydropyrrolo[3,4-a]pyrrolizin-3(2H)-one                            
F25 "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 (1S,3aS,4R,5S,8aS,8bR)-4-[4-(diaminomethyl)phenyl]-1-(difluoromethyl)-2-[(4-fluorophenyl)methyl]-1,3a,4,6,7,8,8a,8b-octahydropyrrolo[4,3-a]pyrrolizin-3-one 
# 
