data_FIR
# 
_chem_comp.id                                    FIR 
_chem_comp.name                                  "(2R,4S)-2-AMINOFORMYL-6-FLUORO-SPIRO[CHROMAN-4,4'-IMIDAZOLIDINE]-2',5'-DIONE" 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C12 H10 F N3 O4" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         FIDARESTAT(STEREOISOMER) 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2004-08-24 
_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                        279.224 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     FIR 
_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        1X97 
_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 
FIR O3I  O3I  O 0 1 N N N 15.917 -5.597  20.515 3.636  1.482  -1.108 O3I  FIR 1  
FIR O6I  O6I  O 0 1 N N N 15.006 -5.698  16.043 1.409  -2.417 -0.818 O6I  FIR 2  
FIR N1I  N1I  N 0 1 N N N 17.028 -6.461  18.682 1.645  1.040  -0.132 N1I  FIR 3  
FIR C2I  C2I  C 0 1 N N N 16.103 -5.858  19.302 2.755  0.698  -0.815 C2I  FIR 4  
FIR N4   N4   N 0 1 N N N 15.086 -5.417  18.408 2.778  -0.601 -1.134 N4   FIR 5  
FIR O10  O10  O 0 1 N N N 17.757 -7.748  14.831 -1.709 -0.121 1.413  O10  FIR 6  
FIR C16  C16  C 0 1 Y N N 16.383 -9.674  15.115 -2.872 0.165  -0.604 C16  FIR 7  
FIR C11  C11  C 0 1 Y N N 16.879 -8.465  15.603 -1.659 0.004  0.066  C11  FIR 8  
FIR C12  C12  C 0 1 Y N N 16.434 -8.050  16.851 -0.484 -0.034 -0.663 C12  FIR 9  
FIR C13  C13  C 0 1 Y N N 15.557 -8.812  17.620 -0.522 0.068  -2.044 C13  FIR 10 
FIR C14  C14  C 0 1 Y N N 15.151 -10.012 17.114 -1.727 0.220  -2.704 C14  FIR 11 
FIR C15  C15  C 0 1 Y N N 15.554 -10.453 15.891 -2.905 0.272  -1.977 C15  FIR 12 
FIR C9   C9   C 0 1 N N R 18.543 -6.743  15.462 -0.497 0.319  2.007  C9   FIR 13 
FIR C5   C5   C 0 1 N N N 15.418 -5.804  17.175 1.678  -1.242 -0.688 C5   FIR 14 
FIR F17  F17  F 0 1 N N N 14.320 -10.778 17.880 -1.755 0.317  -4.051 F17  FIR 15 
FIR O20  O20  O 0 1 N N N 19.408 -5.207  13.643 -1.602 -0.252 4.012  O20  FIR 16 
FIR N21  N21  N 0 1 N N N 20.774 -5.977  15.132 0.456  0.529  4.280  N21  FIR 17 
FIR C19  C19  C 0 1 N N N 19.516 -5.934  14.649 -0.588 0.177  3.504  C19  FIR 18 
FIR C7I  C7I  C 0 1 N N S 16.750 -6.612  17.273 0.853  -0.186 0.007  C7I  FIR 19 
FIR C8I  C8I  C 0 1 N N N 17.565 -5.897  16.224 0.660  -0.540 1.480  C8I  FIR 20 
FIR H1I  H1I  H 0 1 N N N 17.230 -7.363  19.114 1.415  1.921  0.200  H1I  FIR 21 
FIR HN4  HN4  H 0 1 N N N 14.236 -4.895  18.622 3.497  -1.029 -1.625 HN4  FIR 22 
FIR H16  H16  H 0 1 N N N 16.650 -10.019 14.102 -3.793 0.206  -0.042 H16  FIR 23 
FIR H13  H13  H 0 1 N N N 15.193 -8.474  18.605 0.397  0.030  -2.610 H13  FIR 24 
FIR H15  H15  H 0 1 N N N 15.210 -11.437 15.530 -3.849 0.397  -2.487 H15  FIR 25 
FIR H9   H9   H 0 1 N N N 19.289 -7.273  16.100 -0.322 1.363  1.749  H9   FIR 26 
FIR H211 1H21 H 0 0 N N N 21.434 -5.428  14.581 0.397  0.438  5.244  H211 FIR 27 
FIR H212 2H21 H 0 0 N N N 20.862 -6.572  15.956 1.268  0.870  3.874  H212 FIR 28 
FIR H8I1 1H8I H 0 0 N N N 16.888 -5.368  15.513 1.571  -0.319 2.037  H8I1 FIR 29 
FIR H8I2 2H8I H 0 0 N N N 18.093 -5.028  16.682 0.412  -1.597 1.578  H8I2 FIR 30 
# 
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 
FIR O3I C2I  DOUB N N 1  
FIR O6I C5   DOUB N N 2  
FIR N1I C2I  SING N N 3  
FIR N1I C7I  SING N N 4  
FIR N1I H1I  SING N N 5  
FIR C2I N4   SING N N 6  
FIR N4  C5   SING N N 7  
FIR N4  HN4  SING N N 8  
FIR O10 C11  SING N N 9  
FIR O10 C9   SING N N 10 
FIR C16 C11  DOUB Y N 11 
FIR C16 C15  SING Y N 12 
FIR C16 H16  SING N N 13 
FIR C11 C12  SING Y N 14 
FIR C12 C13  DOUB Y N 15 
FIR C12 C7I  SING N N 16 
FIR C13 C14  SING Y N 17 
FIR C13 H13  SING N N 18 
FIR C14 C15  DOUB Y N 19 
FIR C14 F17  SING N N 20 
FIR C15 H15  SING N N 21 
FIR C9  C19  SING N N 22 
FIR C9  C8I  SING N N 23 
FIR C9  H9   SING N N 24 
FIR C5  C7I  SING N N 25 
FIR O20 C19  DOUB N N 26 
FIR N21 C19  SING N N 27 
FIR N21 H211 SING N N 28 
FIR N21 H212 SING N N 29 
FIR C7I C8I  SING N N 30 
FIR C8I H8I1 SING N N 31 
FIR C8I H8I2 SING N N 32 
# 
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 
FIR SMILES           ACDLabs              10.04 Fc3ccc2OC(C(=O)N)CC1(C(=O)NC(=O)N1)c2c3                                                                                                            
FIR InChI            InChI                1.02b InChI=1/C12H10FN3O4/c13-5-1-2-7-6(3-5)12(4-8(20-7)9(14)17)10(18)15-11(19)16-12/h1-3,8H,4H2,(H2,14,17)(H2,15,16,18,19)/t8-,12+/m1/s1/f/h15-16H,14H2 
FIR InChIKey         InChI                1.02b WAAPEIZFCHNLKK-XLMRNDBGDA                                                                                                                          
FIR SMILES_CANONICAL CACTVS               3.341 NC(=O)[C@H]1C[C@]2(NC(=O)NC2=O)c3cc(F)ccc3O1                                                                                                       
FIR SMILES           CACTVS               3.341 NC(=O)[CH]1C[C]2(NC(=O)NC2=O)c3cc(F)ccc3O1                                                                                                         
FIR SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 c1cc2c(cc1F)[C@@]3(C[C@@H](O2)C(=O)N)C(=O)NC(=O)N3                                                                                                 
FIR SMILES           "OpenEye OEToolkits" 1.5.0 c1cc2c(cc1F)C3(CC(O2)C(=O)N)C(=O)NC(=O)N3                                                                                                          
# 
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 
FIR "SYSTEMATIC NAME" ACDLabs              10.04 "(2R,4S)-6-fluoro-2',5'-dioxo-2,3-dihydrospiro[chromene-4,4'-imidazolidine]-2-carboxamide" 
FIR "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "(2R,4S)-6-fluoro-2',5'-dioxo-spiro[chroman-4,4'-imidazolidine]-2-carboxamide"             
# 
