data_G8U
# 
_chem_comp.id                                    G8U 
_chem_comp.name                                  "3-chloro-6-(hydroxymethyl)-2-methyl-5-{4-[3-(trifluoromethoxy)phenoxy]phenyl}pyridin-4-ol" 
_chem_comp.type                                  non-polymer 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C20 H15 Cl F3 N O4" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         ? 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2014-07-27 
_chem_comp.pdbx_modified_date                    2015-01-09 
_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                        425.786 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     G8U 
_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        4UUF 
_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 
G8U C1   C1   C  0 1 N N N 31.860 87.455 9.179  -7.376 0.170  0.177  C1   G8U 1  
G8U F1   F1   F  0 1 N N N 32.639 87.654 8.131  -7.267 1.229  -0.731 F1   G8U 2  
G8U F2   F2   F  0 1 N N N 30.654 87.103 8.775  -7.198 0.651  1.478  F2   G8U 3  
G8U F3   F3   F  0 1 N N N 31.783 88.576 9.872  -8.643 -0.412 0.064  F3   G8U 4  
G8U C4   C4   C  0 1 Y N N 32.307 85.104 9.665  -5.079 -0.403 -0.045 C4   G8U 5  
G8U C5   C5   C  0 1 Y N N 32.630 84.675 8.381  -4.057 -1.301 -0.312 C5   G8U 6  
G8U C6   C6   C  0 1 Y N N 32.522 83.329 8.041  -2.736 -0.883 -0.250 C6   G8U 7  
G8U C7   C7   C  0 1 Y N N 32.106 82.413 9.000  -2.441 0.433  0.079  C7   G8U 8  
G8U C8   C8   C  0 1 Y N N 31.785 82.837 10.284 -3.461 1.326  0.344  C8   G8U 9  
G8U C9   C9   C  0 1 Y N N 31.887 84.182 10.616 -4.779 0.911  0.283  C9   G8U 10 
G8U O10  O10  O  0 1 N N N 32.839 82.870 6.784  -1.732 -1.760 -0.510 O10  G8U 11 
G8U C11  C11  C  0 1 Y N N 32.515 83.505 5.609  -0.453 -1.310 -0.426 C11  G8U 12 
G8U C12  C12  C  0 1 Y N N 31.508 82.982 4.805  0.231  -1.388 0.779  C12  G8U 13 
G8U C13  C13  C  0 1 Y N N 31.174 83.604 3.606  1.529  -0.931 0.868  C13  G8U 14 
G8U C14  C14  C  0 1 Y N N 31.849 84.750 3.204  2.154  -0.390 -0.255 C14  G8U 15 
G8U C15  C15  C  0 1 Y N N 32.860 85.271 4.000  1.465  -0.313 -1.464 C15  G8U 16 
G8U C16  C16  C  0 1 Y N N 33.195 84.648 5.197  0.169  -0.777 -1.547 C16  G8U 17 
G8U C17  C17  C  0 1 Y N N 31.491 85.407 1.919  3.550  0.102  -0.162 C17  G8U 18 
G8U C18  C18  C  0 1 Y N N 32.148 84.984 0.661  4.604  -0.785 0.102  C18  G8U 19 
G8U C19  C19  C  0 1 Y N N 31.742 85.675 -0.581 5.894  -0.269 0.178  C19  G8U 20 
G8U C20  C20  C  0 1 Y N N 30.712 86.738 -0.484 6.091  1.086  -0.008 C20  G8U 21 
G8U C22  C22  C  0 1 Y N N 30.476 86.492 1.854  3.837  1.452  -0.343 C22  G8U 22 
G8U O23  O23  O  0 1 N N N 33.009 84.082 0.644  4.372  -2.110 0.279  O23  G8U 23 
G8U C24  C24  C  0 1 N N N 29.780 86.953 3.110  2.720  2.420  -0.633 C24  G8U 24 
G8U O25  O25  O  0 1 N N N 30.735 87.494 4.029  2.205  2.937  0.595  O25  G8U 25 
G8U CL   CL   CL 0 0 N N N 32.473 85.242 -2.162 7.241  -1.316 0.503  CL   G8U 26 
G8U C27  C27  C  0 1 N N N 30.285 87.453 -1.731 7.485  1.651  0.072  C27  G8U 27 
G8U N28  N28  N  0 1 Y N N 30.155 87.072 0.688  5.076  1.893  -0.255 N28  G8U 28 
G8U O29  O29  O  0 1 N N N 32.406 86.429 10.008 -6.375 -0.808 -0.111 O29  G8U 29 
G8U H5   H5   H  0 1 N N N 32.966 85.390 7.644  -4.289 -2.324 -0.567 H5   G8U 30 
G8U H9   H9   H  0 1 N N N 31.640 84.511 11.614 -5.575 1.611  0.491  H9   G8U 31 
G8U H7   H7   H  0 1 N N N 32.032 81.366 8.746  -1.413 0.759  0.128  H7   G8U 32 
G8U H8   H8   H  0 1 N N N 31.456 82.121 11.023 -3.230 2.349  0.600  H8   G8U 33 
G8U H12  H12  H  0 1 N N N 30.983 82.090 5.112  -0.254 -1.807 1.649  H12  G8U 34 
G8U H16  H16  H  0 1 N N N 33.987 85.053 5.810  -0.365 -0.721 -2.485 H16  G8U 35 
G8U H13  H13  H  0 1 N N N 30.389 83.195 2.987  2.061  -0.992 1.806  H13  G8U 36 
G8U H15  H15  H  0 1 N N N 33.387 86.161 3.689  1.947  0.105  -2.335 H15  G8U 37 
G8U H23  H23  H  0 1 N N N 33.314 83.951 -0.246 4.409  -2.629 -0.536 H23  G8U 38 
G8U H271 H271 H  0 0 N N N 29.520 88.203 -1.481 7.943  1.631  -0.917 H271 G8U 39 
G8U H272 H272 H  0 0 N N N 31.154 87.953 -2.183 7.441  2.679  0.432  H272 G8U 40 
G8U H273 H273 H  0 0 N N N 29.868 86.728 -2.445 8.081  1.051  0.760  H273 G8U 41 
G8U H241 H241 H  0 0 N N N 29.042 87.727 2.854  3.099  3.241  -1.242 H241 G8U 42 
G8U H242 H242 H  0 0 N N N 29.268 86.099 3.577  1.924  1.905  -1.173 H242 G8U 43 
G8U H25  H25  H  0 1 N N N 30.289 87.782 4.817  1.481  3.568  0.484  H25  G8U 44 
# 
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 
G8U C1  F1   SING N N 1  
G8U C1  F2   SING N N 2  
G8U C1  F3   SING N N 3  
G8U C1  O29  SING N N 4  
G8U C4  C5   SING Y N 5  
G8U C4  C9   DOUB Y N 6  
G8U C4  O29  SING N N 7  
G8U C5  C6   DOUB Y N 8  
G8U C6  C7   SING Y N 9  
G8U C6  O10  SING N N 10 
G8U C7  C8   DOUB Y N 11 
G8U C8  C9   SING Y N 12 
G8U O10 C11  SING N N 13 
G8U C11 C12  SING Y N 14 
G8U C11 C16  DOUB Y N 15 
G8U C12 C13  DOUB Y N 16 
G8U C13 C14  SING Y N 17 
G8U C14 C15  DOUB Y N 18 
G8U C14 C17  SING N N 19 
G8U C15 C16  SING Y N 20 
G8U C17 C18  SING Y N 21 
G8U C17 C22  DOUB Y N 22 
G8U C18 C19  DOUB Y N 23 
G8U C18 O23  SING N N 24 
G8U C19 C20  SING Y N 25 
G8U C19 CL   SING N N 26 
G8U C20 C27  SING N N 27 
G8U C20 N28  DOUB Y N 28 
G8U C22 C24  SING N N 29 
G8U C22 N28  SING Y N 30 
G8U C24 O25  SING N N 31 
G8U C5  H5   SING N N 32 
G8U C9  H9   SING N N 33 
G8U C7  H7   SING N N 34 
G8U C8  H8   SING N N 35 
G8U C12 H12  SING N N 36 
G8U C16 H16  SING N N 37 
G8U C13 H13  SING N N 38 
G8U C15 H15  SING N N 39 
G8U O23 H23  SING N N 40 
G8U C27 H271 SING N N 41 
G8U C27 H272 SING N N 42 
G8U C27 H273 SING N N 43 
G8U C24 H241 SING N N 44 
G8U C24 H242 SING N N 45 
G8U O25 H25  SING N N 46 
# 
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 
G8U SMILES           ACDLabs              12.01 "Clc1c(O)c(c(nc1C)CO)c3ccc(Oc2cccc(OC(F)(F)F)c2)cc3"                                                                                         
G8U InChI            InChI                1.03  "InChI=1S/C20H15ClF3NO4/c1-11-18(21)19(27)17(16(10-26)25-11)12-5-7-13(8-6-12)28-14-3-2-4-15(9-14)29-20(22,23)24/h2-9,26H,10H2,1H3,(H,25,27)" 
G8U InChIKey         InChI                1.03  YYKKTOLSPFTXSV-UHFFFAOYSA-N                                                                                                                  
G8U SMILES_CANONICAL CACTVS               3.385 "Cc1nc(CO)c(c(O)c1Cl)c2ccc(Oc3cccc(OC(F)(F)F)c3)cc2"                                                                                         
G8U SMILES           CACTVS               3.385 "Cc1nc(CO)c(c(O)c1Cl)c2ccc(Oc3cccc(OC(F)(F)F)c3)cc2"                                                                                         
G8U SMILES_CANONICAL "OpenEye OEToolkits" 1.7.6 "Cc1c(c(c(c(n1)CO)c2ccc(cc2)Oc3cccc(c3)OC(F)(F)F)O)Cl"                                                                                       
G8U SMILES           "OpenEye OEToolkits" 1.7.6 "Cc1c(c(c(c(n1)CO)c2ccc(cc2)Oc3cccc(c3)OC(F)(F)F)O)Cl"                                                                                       
# 
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 
G8U "SYSTEMATIC NAME" ACDLabs              12.01 "3-chloro-6-(hydroxymethyl)-2-methyl-5-{4-[3-(trifluoromethoxy)phenoxy]phenyl}pyridin-4-ol"      
G8U "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.7.6 "5-chloranyl-2-(hydroxymethyl)-6-methyl-3-[4-[3-(trifluoromethyloxy)phenoxy]phenyl]pyridin-4-ol" 
# 
loop_
_pdbx_chem_comp_audit.comp_id 
_pdbx_chem_comp_audit.action_type 
_pdbx_chem_comp_audit.date 
_pdbx_chem_comp_audit.processing_site 
G8U "Create component" 2014-07-27 EBI  
G8U "Initial release"  2015-01-14 RCSB 
# 
