data_FSN
# 
_chem_comp.id                                    FSN 
_chem_comp.name                                  "(3ASR,4RS,8ASR,8BRS)-4-(2-(4-FLUOROBENZYL)-1,3-DIOXODEACAHYDROPYRROLO[3,4-A] PYRROLIZIN-4-YL)BENZAMIDINE" 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C23 H24 F N4 O2" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         ? 
_chem_comp.pdbx_formal_charge                    1 
_chem_comp.pdbx_initial_date                     2003-04-08 
_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                        407.461 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     FSN 
_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        1OYT 
_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 
FSN O21  O21  O 0 1 N N N 16.695 -12.816 22.729 -0.004 0.972  -0.598 O21  FSN 1  
FSN C20  C20  C 0 1 N N N 17.409 -12.545 21.780 0.329  -0.174 -0.388 C20  FSN 2  
FSN N19  N19  N 0 1 N N N 18.531 -13.329 21.430 1.237  -0.568 0.534  N19  FSN 3  
FSN C23  C23  C 0 1 N N N 18.867 -14.543 22.173 1.941  0.380  1.401  C23  FSN 4  
FSN C24  C24  C 0 1 Y N N 19.788 -14.211 23.315 3.212  0.828  0.728  C24  FSN 5  
FSN C32  C32  C 0 1 Y N N 19.251 -14.080 24.610 3.204  1.941  -0.093 C32  FSN 6  
FSN C31  C31  C 0 1 Y N N 20.106 -13.806 25.677 4.369  2.353  -0.711 C31  FSN 7  
FSN C30  C30  C 0 1 Y N N 21.475 -13.667 25.413 5.545  1.651  -0.509 C30  FSN 8  
FSN F29  F29  F 0 1 N N N 22.247 -13.424 26.487 6.685  2.053  -1.113 F29  FSN 9  
FSN C26  C26  C 0 1 Y N N 22.058 -13.774 24.142 5.553  0.537  0.313  C26  FSN 10 
FSN C25  C25  C 0 1 Y N N 21.174 -14.052 23.069 4.387  0.130  0.935  C25  FSN 11 
FSN C17  C17  C 0 1 N N N 19.064 -12.906 20.178 1.445  -1.889 0.586  C17  FSN 12 
FSN O18  O18  O 0 1 N N N 20.042 -13.392 19.632 2.219  -2.447 1.334  O18  FSN 13 
FSN C16  C16  C 0 1 N N R 18.245 -11.812 19.663 0.565  -2.576 -0.434 C16  FSN 14 
FSN C15  C15  C 0 1 N N S 17.217 -12.198 18.600 -0.519 -3.404 0.286  C15  FSN 15 
FSN N11  N11  N 0 1 N N N 15.799 -12.440 19.140 -1.633 -2.429 0.529  N11  FSN 16 
FSN C12  C12  C 0 1 N N N 14.969 -11.997 17.983 -2.868 -3.281 0.474  C12  FSN 17 
FSN C13  C13  C 0 1 N N N 15.891 -12.193 16.736 -2.602 -4.362 -0.592 C13  FSN 18 
FSN C14  C14  C 0 1 N N N 17.251 -11.672 17.223 -1.068 -4.456 -0.698 C14  FSN 19 
FSN C10  C10  C 0 1 N N R 15.863 -11.337 20.194 -1.676 -1.616 -0.709 C10  FSN 20 
FSN C7   C7   C 0 1 Y N N 14.670 -11.204 21.092 -2.347 -0.293 -0.443 C7   FSN 21 
FSN C8   C8   C 0 1 Y N N 13.928 -12.350 21.361 -3.166 0.269  -1.406 C8   FSN 22 
FSN C9   C9   C 0 1 Y N N 12.851 -12.291 22.235 -3.784 1.480  -1.169 C9   FSN 23 
FSN C4   C4   C 0 1 Y N N 12.524 -11.044 22.837 -3.580 2.138  0.045  C4   FSN 24 
FSN C5   C5   C 0 1 Y N N 13.270 -9.890  22.573 -2.748 1.568  1.009  C5   FSN 25 
FSN C6   C6   C 0 1 Y N N 14.356 -9.961  21.695 -2.141 0.354  0.762  C6   FSN 26 
FSN C3   C3   C 0 1 N N N 11.383 -11.001 23.737 -4.239 3.436  0.305  C3   FSN 27 
FSN N1   N1   N 1 1 N N N 10.552 -12.064 23.887 -4.509 4.261  -0.705 N1   FSN 28 
FSN N2   N2   N 0 1 N N N 11.079 -9.910  24.485 -4.562 3.781  1.550  N2   FSN 29 
FSN C22  C22  C 0 1 N N S 17.247 -11.443 20.807 -0.199 -1.400 -1.098 C22  FSN 30 
FSN H231 1H23 H 0 0 N N N 19.291 -15.334 21.511 1.304  1.244  1.587  H231 FSN 31 
FSN H232 2H23 H 0 0 N N N 17.957 -15.088 22.516 2.183  -0.104 2.348  H232 FSN 32 
FSN H32  H32  H 0 1 N N N 18.168 -14.191 24.787 2.286  2.488  -0.250 H32  FSN 33 
FSN H31  H31  H 0 1 N N N 19.710 -13.702 26.701 4.362  3.222  -1.353 H31  FSN 34 
FSN H26  H26  H 0 1 N N N 23.144 -13.647 23.995 6.469  -0.011 0.471  H26  FSN 35 
FSN H25  H25  H 0 1 N N N 21.565 -14.145 22.042 4.393  -0.739 1.576  H25  FSN 36 
FSN H16  H16  H 0 1 N N N 18.979 -11.064 19.282 1.136  -3.167 -1.150 H16  FSN 37 
FSN H15  H15  H 0 1 N N N 17.706 -13.170 18.357 -0.156 -3.850 1.212  H15  FSN 38 
FSN H121 1H12 H 0 0 N N N 14.560 -10.965 18.087 -3.731 -2.677 0.194  H121 FSN 39 
FSN H122 2H12 H 0 0 N N N 13.985 -12.515 17.906 -3.029 -3.743 1.449  H122 FSN 40 
FSN H131 1H13 H 0 0 N N N 15.517 -11.713 15.802 -3.030 -4.062 -1.549 H131 FSN 41 
FSN H132 2H13 H 0 0 N N N 15.910 -13.231 16.331 -3.018 -5.318 -0.274 H132 FSN 42 
FSN H141 1H14 H 0 0 N N N 18.137 -11.955 16.608 -0.746 -4.226 -1.714 H141 FSN 43 
FSN H142 2H14 H 0 0 N N N 17.427 -10.576 17.117 -0.731 -5.452 -0.412 H142 FSN 44 
FSN H10  H10  H 0 1 N N N 15.756 -10.323 19.743 -2.201 -2.155 -1.498 H10  FSN 45 
FSN H8   H8   H 0 1 N N N 14.194 -13.307 20.881 -3.324 -0.241 -2.345 H8   FSN 46 
FSN H9   H9   H 0 1 N N N 12.273 -13.207 22.445 -4.424 1.917  -1.921 H9   FSN 47 
FSN H5   H5   H 0 1 N N N 13.004 -8.933  23.053 -2.586 2.073  1.950  H5   FSN 48 
FSN H6   H6   H 0 1 N N N 14.951 -9.057  21.483 -1.500 -0.090 1.510  H6   FSN 49 
FSN HN11 1HN1 H 0 0 N N N 9.752  -12.034 24.518 -4.273 4.010  -1.612 HN11 FSN 50 
FSN HN12 2HN1 H 0 0 N N N 10.781 -12.884 23.325 -4.941 5.112  -0.534 HN12 FSN 51 
FSN HN21 1HN2 H 0 0 N N N 10.999 -9.116  23.850 -4.994 4.632  1.721  HN21 FSN 52 
FSN HN22 2HN2 H 0 0 N N N 10.279 -9.880  25.116 -4.370 3.179  2.286  HN22 FSN 53 
FSN H22  H22  H 0 1 N N N 17.422 -10.468 21.319 -0.053 -1.357 -2.177 H22  FSN 54 
# 
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 
FSN O21 C20  DOUB N N 1  
FSN C20 N19  SING N N 2  
FSN C20 C22  SING N N 3  
FSN N19 C23  SING N N 4  
FSN N19 C17  SING N N 5  
FSN C23 C24  SING N N 6  
FSN C23 H231 SING N N 7  
FSN C23 H232 SING N N 8  
FSN C24 C32  DOUB Y N 9  
FSN C24 C25  SING Y N 10 
FSN C32 C31  SING Y N 11 
FSN C32 H32  SING N N 12 
FSN C31 C30  DOUB Y N 13 
FSN C31 H31  SING N N 14 
FSN C30 F29  SING N N 15 
FSN C30 C26  SING Y N 16 
FSN C26 C25  DOUB Y N 17 
FSN C26 H26  SING N N 18 
FSN C25 H25  SING N N 19 
FSN C17 O18  DOUB N N 20 
FSN C17 C16  SING N N 21 
FSN C16 C15  SING N N 22 
FSN C16 C22  SING N N 23 
FSN C16 H16  SING N N 24 
FSN C15 N11  SING N N 25 
FSN C15 C14  SING N N 26 
FSN C15 H15  SING N N 27 
FSN N11 C12  SING N N 28 
FSN N11 C10  SING N N 29 
FSN C12 C13  SING N N 30 
FSN C12 H121 SING N N 31 
FSN C12 H122 SING N N 32 
FSN C13 C14  SING N N 33 
FSN C13 H131 SING N N 34 
FSN C13 H132 SING N N 35 
FSN C14 H141 SING N N 36 
FSN C14 H142 SING N N 37 
FSN C10 C7   SING N N 38 
FSN C10 C22  SING N N 39 
FSN C10 H10  SING N N 40 
FSN C7  C8   DOUB Y N 41 
FSN C7  C6   SING Y N 42 
FSN C8  C9   SING Y N 43 
FSN C8  H8   SING N N 44 
FSN C9  C4   DOUB Y N 45 
FSN C9  H9   SING N N 46 
FSN C4  C5   SING Y N 47 
FSN C4  C3   SING N N 48 
FSN C5  C6   DOUB Y N 49 
FSN C5  H5   SING N N 50 
FSN C6  H6   SING N N 51 
FSN C3  N1   DOUB N N 52 
FSN C3  N2   SING N N 53 
FSN N1  HN11 SING N N 54 
FSN N1  HN12 SING N N 55 
FSN N2  HN21 SING N N 56 
FSN N2  HN22 SING N N 57 
FSN C22 H22  SING N N 58 
# 
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 
FSN SMILES           ACDLabs              10.04 Fc1ccc(cc1)CN2C(=O)C5C(C2=O)C3N(CCC3)C5c4ccc(C(=[NH2+])\N)cc4                                                                                                                                                 
FSN InChI            InChI                1.02b InChI=1/C23H23FN4O2/c24-16-9-3-13(4-10-16)12-28-22(29)18-17-2-1-11-27(17)20(19(18)23(28)30)14-5-7-15(8-6-14)21(25)26/h3-10,17-20H,1-2,11-12H2,(H3,25,26)/p+1/t17-,18-,19-,20-/m0/s1/fC23H24FN4O2/h25-26H2/q+1 
FSN InChIKey         InChI                1.02b GJYCQHGTXMVIBG-JWYNHXOJDN                                                                                                                                                                                     
FSN SMILES_CANONICAL CACTVS               3.341 NC(=[NH2+])c1ccc(cc1)[C@H]2[C@@H]3[C@H]([C@@H]4CCCN24)C(=O)N(Cc5ccc(F)cc5)C3=O                                                                                                                                
FSN SMILES           CACTVS               3.341 NC(=[NH2+])c1ccc(cc1)[CH]2[CH]3[CH]([CH]4CCCN24)C(=O)N(Cc5ccc(F)cc5)C3=O                                                                                                                                      
FSN SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 c1cc(ccc1CN2C(=O)[C@H]3[C@@H]4CCC[N@@]4[C@H]([C@H]3C2=O)c5ccc(cc5)C(=[NH2+])N)F                                                                                                                               
FSN SMILES           "OpenEye OEToolkits" 1.5.0 c1cc(ccc1CN2C(=O)C3C4CCCN4C(C3C2=O)c5ccc(cc5)C(=[NH2+])N)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 
FSN "SYSTEMATIC NAME" ACDLabs              10.04 amino{4-[(3aS,4R,8aS,8bR)-2-(4-fluorobenzyl)-1,3-dioxodecahydropyrrolo[3,4-a]pyrrolizin-4-yl]phenyl}methaniminium                                         
FSN "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 [[4-[(3aS,4R,5S,8aS,8bR)-2-[(4-fluorophenyl)methyl]-1,3-dioxo-4,6,7,8,8a,8b-hexahydro-3aH-pyrrolo[3,4-a]pyrrolizin-4-yl]phenyl]-amino-methylidene]azanium 
# 
