data_OTF
# 
_chem_comp.id                                    OTF 
_chem_comp.name                                  "(1S,2S,3S)-1-fluoranyl-2-[4-(5-fluoranylpyrimidin-2-yl)phenyl]-N-oxidanyl-3-phenyl-cyclopropane-1-carboxamide" 
_chem_comp.type                                  non-polymer 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C20 H15 F2 N3 O2" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         ? 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2015-05-22 
_chem_comp.pdbx_modified_date                    2016-02-05 
_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                        367.349 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     OTF 
_chem_comp.pdbx_model_coordinates_details        ? 
_chem_comp.pdbx_model_coordinates_missing_flag   N 
_chem_comp.pdbx_ideal_coordinates_details        Corina 
_chem_comp.pdbx_ideal_coordinates_missing_flag   N 
_chem_comp.pdbx_model_coordinates_db_code        5A2S 
_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 
OTF C1  C1  C 0 1 N N N -26.000 -29.652 -73.211 3.398  -1.607 0.184  C1  OTF 1  
OTF C2  C2  C 0 1 N N S -27.034 -30.593 -73.832 2.158  -0.956 -0.371 C2  OTF 2  
OTF C3  C3  C 0 1 N N S -28.205 -31.194 -73.017 1.395  0.005  0.542  C3  OTF 3  
OTF C4  C4  C 0 1 N N S -28.487 -30.151 -74.104 2.208  0.551  -0.633 C4  OTF 4  
OTF F5  F5  F 0 1 N N N -26.519 -31.383 -74.750 1.408  -1.740 -1.254 F5  OTF 5  
OTF O6  O6  O 0 1 N N N -26.013 -29.180 -72.085 3.810  -1.291 1.280  O6  OTF 6  
OTF N7  N7  N 0 1 N N N -24.958 -29.421 -73.995 4.046  -2.546 -0.534 N7  OTF 7  
OTF O8  O8  O 0 1 N N N -23.868 -28.703 -73.514 5.211  -3.158 -0.012 O8  OTF 8  
OTF C9  C9  C 0 1 Y N N -29.035 -28.871 -73.588 3.494  1.269  -0.316 C9  OTF 9  
OTF C10 C10 C 0 1 Y N N -30.142 -28.883 -72.750 4.261  1.798  -1.337 C10 OTF 10 
OTF C11 C11 C 0 1 Y N N -30.687 -27.689 -72.278 5.441  2.457  -1.046 C11 OTF 11 
OTF C12 C12 C 0 1 Y N N -30.127 -26.474 -72.657 5.853  2.588  0.267  C12 OTF 12 
OTF C13 C13 C 0 1 Y N N -29.022 -26.462 -73.504 5.086  2.060  1.289  C13 OTF 13 
OTF C14 C14 C 0 1 Y N N -28.486 -27.658 -73.977 3.904  1.405  0.998  C14 OTF 14 
OTF C15 C15 C 0 1 Y N N -28.519 -32.637 -73.291 -0.107 0.035  0.422  C15 OTF 15 
OTF C16 C16 C 0 1 Y N N -28.927 -33.161 -74.530 -0.892 -0.153 1.546  C16 OTF 16 
OTF C17 C17 C 0 1 Y N N -29.191 -34.524 -74.700 -2.268 -0.127 1.442  C17 OTF 17 
OTF C18 C18 C 0 1 Y N N -29.057 -35.408 -73.636 -2.866 0.090  0.202  C18 OTF 18 
OTF C19 C19 C 0 1 Y N N -28.641 -34.886 -72.406 -2.070 0.278  -0.927 C19 OTF 19 
OTF C20 C20 C 0 1 Y N N -28.381 -33.527 -72.236 -0.696 0.256  -0.810 C20 OTF 20 
OTF C21 C21 C 0 1 Y N N -29.305 -36.889 -73.755 -4.344 0.118  0.084  C21 OTF 21 
OTF N22 N22 N 0 1 Y N N -29.292 -37.637 -72.618 -4.894 0.325  -1.105 N22 OTF 22 
OTF C23 C23 C 0 1 Y N N -29.488 -38.965 -72.626 -6.208 0.357  -1.245 C23 OTF 23 
OTF C24 C24 C 0 1 Y N N -29.702 -39.626 -73.828 -7.013 0.169  -0.129 C24 OTF 24 
OTF C25 C25 C 0 1 Y N N -29.704 -38.853 -75.004 -6.403 -0.045 1.100  C25 OTF 25 
OTF N26 N26 N 0 1 Y N N -29.503 -37.517 -74.948 -5.083 -0.069 1.169  N26 OTF 26 
OTF F27 F27 F 0 1 N N N -29.897 -40.972 -73.824 -8.360 0.195  -0.237 F27 OTF 27 
OTF H7  H7  H 0 1 N N N -24.955 -29.763 -74.935 3.714  -2.802 -1.409 H7  OTF 28 
OTF H3  H3  H 0 1 N N N -28.296 -30.852 -71.975 1.790  0.167  1.545  H3  OTF 29 
OTF H4  H4  H 0 1 N N N -28.934 -30.539 -75.032 1.657  0.931  -1.493 H4  OTF 30 
OTF H8  H8  H 0 1 N N N -24.037 -28.432 -72.619 5.605  -3.818 -0.599 H8  OTF 31 
OTF H10 H10 H 0 1 N N N -30.585 -29.825 -72.461 3.939  1.696  -2.363 H10 OTF 32 
OTF H14 H14 H 0 1 N N N -27.640 -27.641 -74.649 3.303  0.996  1.796  H14 OTF 33 
OTF H11 H11 H 0 1 N N N -31.543 -27.708 -71.619 6.041  2.869  -1.844 H11 OTF 34 
OTF H12 H12 H 0 1 N N N -30.546 -25.546 -72.297 6.775  3.102  0.495  H12 OTF 35 
OTF H13 H13 H 0 1 N N N -28.578 -25.522 -73.796 5.409  2.162  2.314  H13 OTF 36 
OTF H16 H16 H 0 1 N N N -29.039 -32.494 -75.372 -0.427 -0.321 2.506  H16 OTF 37 
OTF H20 H20 H 0 1 N N N -28.068 -33.162 -71.269 -0.078 0.407  -1.683 H20 OTF 38 
OTF H17 H17 H 0 1 N N N -29.502 -34.893 -75.666 -2.879 -0.274 2.320  H17 OTF 39 
OTF H19 H19 H 0 1 N N N -28.518 -35.554 -71.566 -2.529 0.446  -1.890 H19 OTF 40 
OTF H23 H23 H 0 1 N N N -29.479 -39.518 -71.699 -6.650 0.526  -2.216 H23 OTF 41 
OTF H25 H25 H 0 1 N N N -29.867 -39.331 -75.959 -7.000 -0.194 1.988  H25 OTF 42 
# 
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 
OTF C1  C2  SING N N 1  
OTF C1  O6  DOUB N N 2  
OTF C1  N7  SING N N 3  
OTF C2  C3  SING N N 4  
OTF C2  C4  SING N N 5  
OTF C2  F5  SING N N 6  
OTF C3  C4  SING N N 7  
OTF C3  C15 SING N N 8  
OTF C4  C9  SING N N 9  
OTF N7  O8  SING N N 10 
OTF C9  C10 SING Y N 11 
OTF C9  C14 DOUB Y N 12 
OTF C10 C11 DOUB Y N 13 
OTF C11 C12 SING Y N 14 
OTF C12 C13 DOUB Y N 15 
OTF C13 C14 SING Y N 16 
OTF C15 C16 SING Y N 17 
OTF C15 C20 DOUB Y N 18 
OTF C16 C17 DOUB Y N 19 
OTF C17 C18 SING Y N 20 
OTF C18 C19 DOUB Y N 21 
OTF C18 C21 SING N N 22 
OTF C19 C20 SING Y N 23 
OTF C21 N22 SING Y N 24 
OTF C21 N26 DOUB Y N 25 
OTF N22 C23 DOUB Y N 26 
OTF C23 C24 SING Y N 27 
OTF C24 C25 DOUB Y N 28 
OTF C24 F27 SING N N 29 
OTF C25 N26 SING Y N 30 
OTF N7  H7  SING N N 31 
OTF C3  H3  SING N N 32 
OTF C4  H4  SING N N 33 
OTF O8  H8  SING N N 34 
OTF C10 H10 SING N N 35 
OTF C14 H14 SING N N 36 
OTF C11 H11 SING N N 37 
OTF C12 H12 SING N N 38 
OTF C13 H13 SING N N 39 
OTF C16 H16 SING N N 40 
OTF C20 H20 SING N N 41 
OTF C17 H17 SING N N 42 
OTF C19 H19 SING N N 43 
OTF C23 H23 SING N N 44 
OTF C25 H25 SING N N 45 
# 
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 
OTF InChI            InChI                1.03  "InChI=1S/C20H15F2N3O2/c21-15-10-23-18(24-11-15)14-8-6-13(7-9-14)17-16(12-4-2-1-3-5-12)20(17,22)19(26)25-27/h1-11,16-17,27H,(H,25,26)/t16-,17-,20+/m1/s1" 
OTF InChIKey         InChI                1.03  MREATSZIGJDNKB-HLIPFELVSA-N                                                                                                                               
OTF SMILES_CANONICAL CACTVS               3.385 "ONC(=O)[C@]1(F)[C@@H]([C@H]1c2ccc(cc2)c3ncc(F)cn3)c4ccccc4"                                                                                              
OTF SMILES           CACTVS               3.385 "ONC(=O)[C]1(F)[CH]([CH]1c2ccc(cc2)c3ncc(F)cn3)c4ccccc4"                                                                                                  
OTF SMILES_CANONICAL "OpenEye OEToolkits" 1.7.6 "c1ccc(cc1)[C@@H]2[C@H]([C@@]2(C(=O)NO)F)c3ccc(cc3)c4ncc(cn4)F"                                                                                           
OTF SMILES           "OpenEye OEToolkits" 1.7.6 "c1ccc(cc1)C2C(C2(C(=O)NO)F)c3ccc(cc3)c4ncc(cn4)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 
OTF "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.7.6 "(1S,2S,3S)-1-fluoranyl-2-[4-(5-fluoranylpyrimidin-2-yl)phenyl]-N-oxidanyl-3-phenyl-cyclopropane-1-carboxamide" 
# 
loop_
_pdbx_chem_comp_audit.comp_id 
_pdbx_chem_comp_audit.action_type 
_pdbx_chem_comp_audit.date 
_pdbx_chem_comp_audit.processing_site 
OTF "Create component"   2015-05-22 EBI  
OTF "Other modification" 2015-05-27 EBI  
OTF "Initial release"    2016-02-10 RCSB 
# 
