data_FEQ
# 
_chem_comp.id                                    FEQ 
_chem_comp.name                                  "(1~{S},2~{S},5~{S},6~{R})-5-(2,4-dinitrophenoxy)-6-fluoranyl-3-(hydroxymethyl)cyclohex-3-ene-1,2-diol" 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C13 H13 F N2 O8" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         ? 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2018-06-25 
_chem_comp.pdbx_modified_date                    2018-08-17 
_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                        344.249 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     FEQ 
_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        6GWF 
_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 
FEQ OAU O1  O -1 1 N N N 9.892  -14.443 -22.023 -3.090 -3.085 0.915  OAU FEQ 1  
FEQ NAT N1  N 1  1 N N N 8.593  -14.969 -21.732 -2.079 -2.478 0.609  NAT FEQ 2  
FEQ OAV O2  O 0  1 N N N 8.434  -16.299 -21.844 -0.998 -3.036 0.651  OAV FEQ 3  
FEQ CAN C1  C 0  1 Y N N 7.477  -14.232 -21.487 -2.166 -1.064 0.179  CAN FEQ 4  
FEQ CAO C2  C 0  1 Y N N 6.295  -14.536 -22.164 -3.393 -0.430 0.131  CAO FEQ 5  
FEQ CAP C3  C 0  1 Y N N 5.110  -13.838 -21.899 -3.475 0.890  -0.271 CAP FEQ 6  
FEQ NAS N2  N 1  1 N N N 3.964  -14.072 -22.597 -4.790 1.567  -0.322 NAS FEQ 7  
FEQ OAX O3  O -1 1 N N N 3.974  -15.063 -23.645 -4.864 2.730  -0.675 OAX FEQ 8  
FEQ OAW O4  O 0  1 N N N 2.791  -12.940 -22.512 -5.799 0.960  -0.010 OAW FEQ 9  
FEQ CAQ C4  C 0  1 Y N N 5.123  -12.813 -20.946 -2.330 1.580  -0.625 CAQ FEQ 10 
FEQ CAR C5  C 0  1 Y N N 6.294  -12.518 -20.243 -1.101 0.951  -0.578 CAR FEQ 11 
FEQ CAM C6  C 0  1 Y N N 7.455  -13.244 -20.484 -1.015 -0.373 -0.170 CAM FEQ 12 
FEQ OAL O5  O 0  1 N N N 8.614  -12.929 -19.847 0.193  -0.993 -0.118 OAL FEQ 13 
FEQ CAA C7  C 0  1 N N S 8.689  -12.792 -18.378 1.319  -0.262 -0.608 CAA FEQ 14 
FEQ CAB C8  C 0  1 N N N 8.813  -14.079 -17.752 1.834  0.642  0.473  CAB FEQ 15 
FEQ CAE C9  C 0  1 N N R 9.923  -11.908 -18.128 2.411  -1.242 -1.041 CAE FEQ 16 
FEQ FAH F1  F 0  1 N N N 9.955  -10.708 -19.081 2.638  -2.173 -0.022 FAH FEQ 17 
FEQ CAD C10 C 0  1 N N S 11.150 -12.699 -18.502 3.694  -0.448 -1.316 CAD FEQ 18 
FEQ OAG O6  O 0  1 N N N 12.428 -11.940 -18.478 3.413  0.621  -2.221 OAG FEQ 19 
FEQ CAC C11 C 0  1 N N S 11.266 -13.939 -17.568 4.205  0.120  0.010  CAC FEQ 20 
FEQ OAF O7  O 0  1 N N N 11.967 -13.511 -16.358 5.253  1.056  -0.249 OAF FEQ 21 
FEQ CAI C12 C 0  1 N N N 10.032 -14.596 -17.309 3.090  0.812  0.739  CAI FEQ 22 
FEQ CAJ C13 C 0  1 N N N 10.135 -15.919 -16.725 3.455  1.763  1.849  CAJ FEQ 23 
FEQ OAK O8  O 0  1 N N N 8.877  -16.599 -16.497 2.264  2.315  2.415  OAK FEQ 24 
FEQ H1  H1  H 0  1 N N N 6.294  -15.322 -22.904 -4.289 -0.967 0.407  H1  FEQ 25 
FEQ H2  H2  H 0  1 N N N 4.223  -12.247 -20.753 -2.396 2.611  -0.939 H2  FEQ 26 
FEQ H3  H3  H 0  1 N N N 6.297  -11.724 -19.511 -0.207 1.490  -0.854 H3  FEQ 27 
FEQ H4  H4  H 0  1 N N N 7.795  -12.270 -18.007 1.013  0.340  -1.464 H4  FEQ 28 
FEQ H5  H5  H 0  1 N N N 7.922  -14.674 -17.618 1.113  1.185  1.066  H5  FEQ 29 
FEQ H6  H6  H 0  1 N N N 9.963  -11.579 -17.079 2.099  -1.760 -1.948 H6  FEQ 30 
FEQ H7  H7  H 0  1 N N N 11.002 -13.078 -19.524 4.447  -1.107 -1.750 H7  FEQ 31 
FEQ H8  H8  H 0  1 N N N 13.143 -12.515 -18.726 3.070  0.332  -3.077 H8  FEQ 32 
FEQ H9  H9  H 0  1 N N N 11.922 -14.653 -18.088 4.591  -0.691 0.626  H9  FEQ 33 
FEQ H10 H10 H 0  1 N N N 12.054 -14.248 -15.765 5.627  1.458  0.548  H10 FEQ 34 
FEQ H11 H11 H 0  1 N N N 10.739 -16.542 -17.401 4.008  1.226  2.620  H11 FEQ 35 
FEQ H12 H12 H 0  1 N N N 10.649 -15.823 -15.757 4.074  2.566  1.451  H12 FEQ 36 
FEQ H13 H13 H 0  1 N N N 9.043  -17.453 -16.115 2.424  2.937  3.137  H13 FEQ 37 
# 
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 
FEQ OAX NAS SING N N 1  
FEQ NAS OAW DOUB N N 2  
FEQ NAS CAP SING N N 3  
FEQ CAO CAP DOUB Y N 4  
FEQ CAO CAN SING Y N 5  
FEQ OAU NAT SING N N 6  
FEQ CAP CAQ SING Y N 7  
FEQ OAV NAT DOUB N N 8  
FEQ NAT CAN SING N N 9  
FEQ CAN CAM DOUB Y N 10 
FEQ CAQ CAR DOUB Y N 11 
FEQ CAM CAR SING Y N 12 
FEQ CAM OAL SING N N 13 
FEQ OAL CAA SING N N 14 
FEQ FAH CAE SING N N 15 
FEQ CAD OAG SING N N 16 
FEQ CAD CAE SING N N 17 
FEQ CAD CAC SING N N 18 
FEQ CAA CAE SING N N 19 
FEQ CAA CAB SING N N 20 
FEQ CAB CAI DOUB N N 21 
FEQ CAC CAI SING N N 22 
FEQ CAC OAF SING N N 23 
FEQ CAI CAJ SING N N 24 
FEQ CAJ OAK SING N N 25 
FEQ CAO H1  SING N N 26 
FEQ CAQ H2  SING N N 27 
FEQ CAR H3  SING N N 28 
FEQ CAA H4  SING N N 29 
FEQ CAB H5  SING N N 30 
FEQ CAE H6  SING N N 31 
FEQ CAD H7  SING N N 32 
FEQ OAG H8  SING N N 33 
FEQ CAC H9  SING N N 34 
FEQ OAF H10 SING N N 35 
FEQ CAJ H11 SING N N 36 
FEQ CAJ H12 SING N N 37 
FEQ OAK H13 SING N N 38 
# 
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 
FEQ InChI            InChI                1.03  "InChI=1S/C13H13FN2O8/c14-11-10(3-6(5-17)12(18)13(11)19)24-9-2-1-7(15(20)21)4-8(9)16(22)23/h1-4,10-13,17-19H,5H2/t10-,11-,12-,13+/m0/s1" 
FEQ InChIKey         InChI                1.03  WVAYSDIDYBKDLD-ZDEQEGDKSA-N                                                                                                              
FEQ SMILES_CANONICAL CACTVS               3.385 "OCC1=C[C@H](Oc2ccc(cc2[N+]([O-])=O)[N+]([O-])=O)[C@H](F)[C@@H](O)[C@H]1O"                                                               
FEQ SMILES           CACTVS               3.385 "OCC1=C[CH](Oc2ccc(cc2[N+]([O-])=O)[N+]([O-])=O)[CH](F)[CH](O)[CH]1O"                                                                    
FEQ SMILES_CANONICAL "OpenEye OEToolkits" 2.0.6 "c1cc(c(cc1[N+](=O)[O-])[N+](=O)[O-])O[C@H]2C=C([C@@H]([C@@H]([C@H]2F)O)O)CO"                                                            
FEQ SMILES           "OpenEye OEToolkits" 2.0.6 "c1cc(c(cc1[N+](=O)[O-])[N+](=O)[O-])OC2C=C(C(C(C2F)O)O)CO"                                                                              
# 
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 
FEQ "SYSTEMATIC NAME" "OpenEye OEToolkits" 2.0.6 "(1~{S},2~{S},5~{S},6~{R})-5-(2,4-dinitrophenoxy)-6-fluoranyl-3-(hydroxymethyl)cyclohex-3-ene-1,2-diol" 
# 
loop_
_pdbx_chem_comp_audit.comp_id 
_pdbx_chem_comp_audit.action_type 
_pdbx_chem_comp_audit.date 
_pdbx_chem_comp_audit.processing_site 
FEQ "Create component" 2018-06-25 RCSB 
FEQ "Initial release"  2018-08-22 RCSB 
# 
