data_EFZ
# 
_chem_comp.id                                    EFZ 
_chem_comp.name                                  (-)-6-CHLORO-4-CYCLOPROPYLETHYNYL-4-TRIFLUOROMETHYL-1,4-DIHYDRO-2H-3,1-BENZOXAZIN-2-ONE 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C14 H9 Cl F3 N O2" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         DMP-266 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2000-08-15 
_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                        315.675 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     EFZ 
_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        1JKH 
_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 
EFZ CL   CL   CL 0 0 N N N -4.665 -32.811 24.129 3.000  -0.531 -2.874 CL   EFZ 1  
EFZ F1   F1   F  0 1 N N N 0.754  -37.406 23.978 -2.234 -1.627 1.695  F1   EFZ 2  
EFZ F2   F2   F  0 1 N N N -1.224 -36.905 24.576 -0.063 -1.567 2.401  F2   EFZ 3  
EFZ F3   F3   F  0 1 N N N -0.843 -37.496 22.566 -0.568 -2.385 0.328  F3   EFZ 4  
EFZ O1   O1   O  0 1 N N N 1.556  -35.723 20.059 -0.624 1.525  3.802  O1   EFZ 5  
EFZ O2   O2   O  0 1 N N N 0.948  -35.286 22.156 -1.108 0.964  1.706  O2   EFZ 6  
EFZ N    N    N  0 1 N N N -0.625 -35.162 20.409 1.095  1.228  2.428  N    EFZ 7  
EFZ C1   C1   C  0 1 Y N N -1.609 -34.574 21.277 1.557  0.804  1.177  C1   EFZ 8  
EFZ C2   C2   C  0 1 Y N N -2.808 -34.013 20.773 2.888  0.974  0.823  C2   EFZ 9  
EFZ C3   C3   C  0 1 Y N N -3.739 -33.466 21.678 3.327  0.562  -0.419 C3   EFZ 10 
EFZ C4   C4   C  0 1 Y N N -3.498 -33.484 23.047 2.445  -0.026 -1.308 C4   EFZ 11 
EFZ C5   C5   C  0 1 Y N N -2.332 -34.024 23.556 1.121  -0.214 -0.950 C5   EFZ 12 
EFZ C6   C6   C  0 1 Y N N -1.406 -34.605 22.675 0.679  0.191  0.291  C6   EFZ 13 
EFZ C7   C7   C  0 1 N N S -0.096 -35.286 23.197 -0.754 -0.029 0.703  C7   EFZ 14 
EFZ C8   C8   C  0 1 N N N 0.455  -34.607 24.391 -1.637 0.113  -0.465 C8   EFZ 15 
EFZ C9   C9   C  0 1 N N N 0.890  -34.050 25.320 -2.340 0.227  -1.398 C9   EFZ 16 
EFZ C10  C10  C  0 1 N N N 1.519  -33.218 26.667 -3.222 0.369  -2.568 C10  EFZ 17 
EFZ C11  C11  C  0 1 N N N 2.254  -32.340 26.203 -3.211 1.712  -3.302 C11  EFZ 18 
EFZ C12  C12  C  0 1 N N N 1.063  -32.072 26.592 -2.560 0.485  -3.942 C12  EFZ 19 
EFZ C13  C13  C  0 1 N N N -0.357 -36.796 23.583 -0.908 -1.432 1.295  C13  EFZ 20 
EFZ C14  C14  C  0 1 N N N 0.681  -35.412 20.804 -0.227 1.250  2.688  C14  EFZ 21 
EFZ HN   HN   H  0 1 N N N -0.868 -35.418 19.452 1.727  1.506  3.109  HN   EFZ 22 
EFZ H2   H2   H  0 1 N N N -3.014 -34.002 19.689 3.578  1.429  1.518  H2   EFZ 23 
EFZ H3   H3   H  0 1 N N N -4.674 -33.014 21.307 4.361  0.700  -0.698 H3   EFZ 24 
EFZ H5   H5   H  0 1 N N N -2.144 -33.991 24.642 0.434  -0.679 -1.643 H5   EFZ 25 
EFZ H101 1H10 H  0 0 N N N 1.613  -33.977 27.477 -4.171 -0.163 -2.509 H101 EFZ 26 
EFZ H111 1H11 H  0 0 N N N 3.274  -31.951 26.429 -4.152 2.062  -3.726 H111 EFZ 27 
EFZ H112 2H11 H  0 0 N N N 2.836  -32.201 25.262 -2.550 2.490  -2.918 H112 EFZ 28 
EFZ H121 1H12 H  0 0 N N N 0.161  -31.599 26.136 -1.471 0.455  -3.980 H121 EFZ 29 
EFZ H122 2H12 H  0 0 N N N 0.599  -31.349 27.303 -3.073 0.027  -4.788 H122 EFZ 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 
EFZ CL  C4   SING N N 1  
EFZ F1  C13  SING N N 2  
EFZ F2  C13  SING N N 3  
EFZ F3  C13  SING N N 4  
EFZ O1  C14  DOUB N N 5  
EFZ O2  C7   SING N N 6  
EFZ O2  C14  SING N N 7  
EFZ N   C1   SING N N 8  
EFZ N   C14  SING N N 9  
EFZ N   HN   SING N N 10 
EFZ C1  C2   DOUB Y N 11 
EFZ C1  C6   SING Y N 12 
EFZ C2  C3   SING Y N 13 
EFZ C2  H2   SING N N 14 
EFZ C3  C4   DOUB Y N 15 
EFZ C3  H3   SING N N 16 
EFZ C4  C5   SING Y N 17 
EFZ C5  C6   DOUB Y N 18 
EFZ C5  H5   SING N N 19 
EFZ C6  C7   SING N N 20 
EFZ C7  C8   SING N N 21 
EFZ C7  C13  SING N N 22 
EFZ C8  C9   TRIP N N 23 
EFZ C9  C10  SING N N 24 
EFZ C10 C11  SING N N 25 
EFZ C10 C12  SING N N 26 
EFZ C10 H101 SING N N 27 
EFZ C11 C12  SING N N 28 
EFZ C11 H111 SING N N 29 
EFZ C11 H112 SING N N 30 
EFZ C12 H121 SING N N 31 
EFZ C12 H122 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 
EFZ SMILES           ACDLabs              10.04 FC(F)(F)C3(C#CC1CC1)OC(=O)Nc2c3cc(Cl)cc2                                                                                       
EFZ InChI            InChI                1.02b InChI=1/C14H9ClF3NO2/c15-9-3-4-11-10(7-9)13(14(16,17)18,21-12(20)19-11)6-5-8-1-2-8/h3-4,7-8H,1-2H2,(H,19,20)/t13-/m0/s1/f/h19H 
EFZ InChIKey         InChI                1.02b XPOQHMRABVBWPR-VKDSSWMGDD                                                                                                      
EFZ SMILES_CANONICAL CACTVS               3.341 FC(F)(F)[C@]1(OC(=O)Nc2ccc(Cl)cc12)C#CC3CC3                                                                                    
EFZ SMILES           CACTVS               3.341 FC(F)(F)[C]1(OC(=O)Nc2ccc(Cl)cc12)C#CC3CC3                                                                                     
EFZ SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 c1cc2c(cc1Cl)[C@@](OC(=O)N2)(C#CC3CC3)C(F)(F)F                                                                                 
EFZ SMILES           "OpenEye OEToolkits" 1.5.0 c1cc2c(cc1Cl)C(OC(=O)N2)(C#CC3CC3)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 
EFZ "SYSTEMATIC NAME" ACDLabs              10.04 (4S)-6-chloro-4-(cyclopropylethynyl)-4-(trifluoromethyl)-1,4-dihydro-2H-3,1-benzoxazin-2-one 
EFZ "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 (4S)-6-chloro-4-(2-cyclopropylethynyl)-4-(trifluoromethyl)-1H-3,1-benzoxazin-2-one           
# 
