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 2011-06-04 _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 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" F25 InChI InChI 1.03 "InChI=1S/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 1.03 VPNYXOTTXAXSIH-SXYSDOLCSA-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 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" # loop_ _pdbx_chem_comp_audit.comp_id _pdbx_chem_comp_audit.action_type _pdbx_chem_comp_audit.date _pdbx_chem_comp_audit.processing_site F25 "Create component" 2006-05-17 EBI F25 "Modify descriptor" 2011-06-04 RCSB #