data_TOL
# 
_chem_comp.id                                    TOL 
_chem_comp.name                                  TOLRESTAT 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C16 H14 F3 N O3 S" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         ? 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     1999-07-08 
_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                        357.347 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     TOL 
_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        1AE4 
_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 
TOL C1   C1   C 0 1 N N N -34.178 28.542 -1.388 -0.843 0.093  3.962  C1   TOL 1  
TOL F1   F1   F 0 1 N N N -35.235 27.715 -1.606 -1.515 -1.117 4.160  F1   TOL 2  
TOL F2   F2   F 0 1 N N N -33.154 27.796 -0.901 0.017  0.330  5.040  F2   TOL 3  
TOL F3   F3   F 0 1 N N N -33.780 29.017 -2.598 -1.773 1.134  3.871  F3   TOL 4  
TOL C2   C2   C 0 1 Y N N -34.564 29.679 -0.417 -0.042 0.022  2.687  C2   TOL 5  
TOL C3   C3   C 0 1 Y N N -34.249 31.046 -0.635 1.321  0.086  2.727  C3   TOL 6  
TOL O1   O1   O 0 1 N N N -33.587 31.398 -1.721 1.951  0.214  3.925  O1   TOL 7  
TOL C4   C4   C 0 1 N N N -32.906 32.634 -1.578 3.353  0.247  3.652  C4   TOL 8  
TOL C5   C5   C 0 1 Y N N -34.646 32.009 0.320  2.077  0.017  1.554  C5   TOL 9  
TOL C6   C6   C 0 1 Y N N -35.344 31.630 1.471  1.473  -0.110 0.340  C6   TOL 10 
TOL C7   C7   C 0 1 Y N N -35.657 30.274 1.692  0.076  -0.173 0.264  C7   TOL 11 
TOL C8   C8   C 0 1 Y N N -36.363 29.905 2.861  -0.612 -0.310 -1.017 C8   TOL 12 
TOL C9   C9   C 0 1 Y N N -36.676 28.553 3.080  -2.000 -0.366 -1.025 C9   TOL 13 
TOL C10  C10  C 0 1 Y N N -36.293 27.580 2.154  -2.716 -0.294 0.161  C10  TOL 14 
TOL C11  C11  C 0 1 Y N N -35.595 27.951 0.998  -2.096 -0.166 1.367  C11  TOL 15 
TOL C12  C12  C 0 1 Y N N -35.270 29.298 0.754  -0.695 -0.104 1.450  C12  TOL 16 
TOL C13  C13  C 0 1 N N N -36.814 30.889 3.914  0.149  -0.385 -2.275 C13  TOL 17 
TOL S1   S1   S 0 1 N N N -38.430 31.458 3.898  0.759  -1.890 -2.818 S1   TOL 18 
TOL N1   N1   N 0 1 N N N -35.955 31.292 4.851  0.367  0.729  -2.999 N1   TOL 19 
TOL C14  C14  C 0 1 N N N -34.618 30.712 4.906  -0.052 2.033  -2.480 C14  TOL 20 
TOL C15  C15  C 0 1 N N N -36.322 32.294 5.847  1.024  0.638  -4.306 C15  TOL 21 
TOL C16  C16  C 0 1 N N N -36.393 33.703 5.231  -0.016 0.448  -5.379 C16  TOL 22 
TOL O2   O2   O 0 1 N N N -36.865 34.638 5.823  -1.186 0.395  -5.083 O2   TOL 23 
TOL O3   O3   O 0 1 N N N -35.889 33.817 3.998  0.356  0.339  -6.664 O3   TOL 24 
TOL H41  1H4  H 0 1 N N N -32.346 32.931 -2.495 3.903  0.349  4.587  H41  TOL 25 
TOL H42  2H4  H 0 1 N N N -33.607 33.440 -1.260 3.649  -0.676 3.155  H42  TOL 26 
TOL H43  3H4  H 0 1 N N N -32.232 32.617 -0.689 3.577  1.095  3.004  H43  TOL 27 
TOL H5   H5   H 0 1 N N N -34.407 33.074 0.164  3.154  0.066  1.611  H5   TOL 28 
TOL H6   H6   H 0 1 N N N -35.646 32.398 2.202  2.068  -0.162 -0.559 H6   TOL 29 
TOL H9   H9   H 0 1 N N N -37.227 28.252 3.986  -2.527 -0.467 -1.962 H9   TOL 30 
TOL H10  H10  H 0 1 N N N -36.541 26.520 2.335  -3.794 -0.340 0.128  H10  TOL 31 
TOL H11  H11  H 0 1 N N N -35.298 27.174 0.272  -2.688 -0.113 2.269  H11  TOL 32 
TOL H141 1H14 H 0 0 N N N -33.899 31.049 5.689  -0.597 1.894  -1.546 H141 TOL 33 
TOL H142 2H14 H 0 0 N N N -34.715 29.603 4.968  0.826  2.652  -2.299 H142 TOL 34 
TOL H143 3H14 H 0 0 N N N -34.136 30.836 3.907  -0.698 2.524  -3.208 H143 TOL 35 
TOL H151 1H15 H 0 0 N N N -37.273 32.026 6.363  1.580  1.556  -4.497 H151 TOL 36 
TOL H152 2H15 H 0 0 N N N -35.635 32.266 6.724  1.709  -0.209 -4.310 H152 TOL 37 
TOL HO3  HO3  H 0 1 N N N -35.932 34.686 3.617  -0.311 0.217  -7.352 HO3  TOL 38 
# 
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 
TOL C1  F1   SING N N 1  
TOL C1  F2   SING N N 2  
TOL C1  F3   SING N N 3  
TOL C1  C2   SING N N 4  
TOL C2  C3   DOUB Y N 5  
TOL C2  C12  SING Y N 6  
TOL C3  O1   SING N N 7  
TOL C3  C5   SING Y N 8  
TOL O1  C4   SING N N 9  
TOL C4  H41  SING N N 10 
TOL C4  H42  SING N N 11 
TOL C4  H43  SING N N 12 
TOL C5  C6   DOUB Y N 13 
TOL C5  H5   SING N N 14 
TOL C6  C7   SING Y N 15 
TOL C6  H6   SING N N 16 
TOL C7  C8   DOUB Y N 17 
TOL C7  C12  SING Y N 18 
TOL C8  C9   SING Y N 19 
TOL C8  C13  SING N N 20 
TOL C9  C10  DOUB Y N 21 
TOL C9  H9   SING N N 22 
TOL C10 C11  SING Y N 23 
TOL C10 H10  SING N N 24 
TOL C11 C12  DOUB Y N 25 
TOL C11 H11  SING N N 26 
TOL C13 S1   DOUB N N 27 
TOL C13 N1   SING N N 28 
TOL N1  C14  SING N N 29 
TOL N1  C15  SING N N 30 
TOL C14 H141 SING N N 31 
TOL C14 H142 SING N N 32 
TOL C14 H143 SING N N 33 
TOL C15 C16  SING N N 34 
TOL C15 H151 SING N N 35 
TOL C15 H152 SING N N 36 
TOL C16 O2   DOUB N N 37 
TOL C16 O3   SING N N 38 
TOL O3  HO3  SING N N 39 
# 
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 
TOL SMILES           ACDLabs              10.04 "O=C(O)CN(C(=S)c2c1ccc(OC)c(c1ccc2)C(F)(F)F)C"                                                                          
TOL SMILES_CANONICAL CACTVS               3.341 "COc1ccc2c(cccc2c1C(F)(F)F)C(=S)N(C)CC(O)=O"                                                                            
TOL SMILES           CACTVS               3.341 "COc1ccc2c(cccc2c1C(F)(F)F)C(=S)N(C)CC(O)=O"                                                                            
TOL SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 "CN(CC(=O)O)C(=S)c1cccc2c1ccc(c2C(F)(F)F)OC"                                                                            
TOL SMILES           "OpenEye OEToolkits" 1.5.0 "CN(CC(=O)O)C(=S)c1cccc2c1ccc(c2C(F)(F)F)OC"                                                                            
TOL InChI            InChI                1.03  "InChI=1S/C16H14F3NO3S/c1-20(8-13(21)22)15(24)11-5-3-4-10-9(11)6-7-12(23-2)14(10)16(17,18)19/h3-7H,8H2,1-2H3,(H,21,22)" 
TOL InChIKey         InChI                1.03  LUBHDINQXIHVLS-UHFFFAOYSA-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 
TOL "SYSTEMATIC NAME" ACDLabs              10.04 "N-{[6-methoxy-5-(trifluoromethyl)naphthalen-1-yl]carbonothioyl}-N-methylglycine"         
TOL "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "2-[[6-methoxy-5-(trifluoromethyl)naphthalen-1-yl]carbothioyl-methyl-amino]ethanoic acid" 
# 
loop_
_pdbx_chem_comp_audit.comp_id 
_pdbx_chem_comp_audit.action_type 
_pdbx_chem_comp_audit.date 
_pdbx_chem_comp_audit.processing_site 
TOL "Create component"  1999-07-08 EBI  
TOL "Modify descriptor" 2011-06-04 RCSB 
# 
