data_234
# 
_chem_comp.id                                    234 
_chem_comp.name                                  "5-{2-FLUORO-5-[3-(3-HYDROXY-2-METHOXYCARBONYL-PHENOXY)-PROPENYL]-PHENYL}-ISOXAZOLE-3-CARBOXYLIC ACID" 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C21 H16 F N O7" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         "COMPOUND 9" 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2003-07-22 
_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                        413.353 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     234 
_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        1Q1M 
_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 
234 C1   C1   C 0 1 Y N N 33.046 31.094 18.433 1.884  -0.786 3.453  C1   234 1  
234 C2   C2   C 0 1 Y N N 32.506 30.481 19.609 0.593  -0.247 3.473  C2   234 2  
234 C3   C3   C 0 1 Y N N 31.114 30.620 19.843 -0.162 -0.215 2.303  C3   234 3  
234 C4   C4   C 0 1 Y N N 30.274 31.334 18.952 0.368  -0.731 1.124  C4   234 4  
234 C5   C5   C 0 1 Y N N 30.839 31.926 17.792 1.658  -1.266 1.116  C5   234 5  
234 C6   C6   C 0 1 Y N N 32.225 31.812 17.526 2.406  -1.291 2.275  C6   234 6  
234 C7   C7   C 0 1 Y N N 33.294 29.705 20.623 0.035  0.292  4.731  C7   234 7  
234 O12  O12  O 0 1 Y N N 32.689 29.167 21.747 -0.376 1.552  4.955  O12  234 8  
234 N13  N13  N 0 1 Y N N 33.709 28.520 22.477 -0.785 1.696  6.083  N13  234 9  
234 C14  C14  C 0 1 Y N N 34.887 28.661 21.814 -0.712 0.583  6.772  C14  234 10 
234 C15  C15  C 0 1 Y N N 34.619 29.433 20.605 -0.168 -0.392 5.897  C15  234 11 
234 C16  C16  C 0 1 N N N 36.254 28.126 22.225 -1.121 0.382  8.183  C16  234 12 
234 O1   O1   O 0 1 N N N 37.224 28.872 22.225 -1.630 1.410  8.889  O1   234 13 
234 O2   O2   O 0 1 N N N 36.288 26.800 22.580 -0.997 -0.707 8.702  O2   234 14 
234 C8   C8   C 0 1 N N N 28.809 31.486 19.196 -0.429 -0.706 -0.119 C8   234 15 
234 C32  C32  C 0 1 Y N N 24.749 29.996 21.499 -0.825 -0.411 -4.615 C32  234 16 
234 C33  C33  C 0 1 Y N N 23.927 31.186 21.541 -2.031 -1.094 -4.614 C33  234 17 
234 C34  C34  C 0 1 Y N N 22.540 31.119 21.836 -2.823 -1.108 -5.746 C34  234 18 
234 C35  C35  C 0 1 Y N N 21.937 29.867 22.099 -2.427 -0.439 -6.889 C35  234 19 
234 C36  C36  C 0 1 Y N N 22.700 28.669 22.072 -1.228 0.254  -6.911 C36  234 20 
234 C37  C37  C 0 1 Y N N 24.111 28.708 21.778 -0.415 0.276  -5.767 C37  234 21 
234 C38  C38  C 0 1 N N N 24.870 27.420 21.767 0.859  1.009  -5.778 C38  234 22 
234 O11  O11  O 0 1 N N N 24.934 26.728 22.766 0.891  2.178  -5.447 O11  234 23 
234 O4   O4   O 0 1 N N N 25.460 27.098 20.602 1.992  0.384  -6.155 O4   234 24 
234 C39  C39  C 0 1 N N N 26.211 25.866 20.531 3.251  1.108  -6.166 C39  234 25 
234 O14  O14  O 0 1 N N N 22.009 27.492 22.347 -0.841 0.909  -8.033 O14  234 26 
234 O3   O3   O 0 1 N N N 26.155 30.039 21.202 -0.049 -0.398 -3.502 O3   234 27 
234 C40  C40  C 0 1 N N N 26.650 31.150 20.467 -0.735 -1.166 -2.511 C40  234 28 
234 C41  C41  C 0 1 N N N 28.131 30.979 20.266 0.078  -1.192 -1.243 C41  234 29 
234 F1   F1   F 0 1 N N N 34.352 31.014 18.142 2.621  -0.814 4.585  F1   234 30 
234 H3   H3   H 0 1 N N N 30.672 30.160 20.743 -1.159 0.199  2.313  H3   234 31 
234 H5   H5   H 0 1 N N N 30.194 32.481 17.090 2.072  -1.662 0.200  H5   234 32 
234 H6   H6   H 0 1 N N N 32.659 32.276 16.625 3.402  -1.707 2.264  H6   234 33 
234 H15  H15  H 0 1 N N N 35.307 29.758 19.807 0.040  -1.431 6.105  H15  234 34 
234 HO1  HO1  H 0 1 N N N 38.076 28.539 22.481 -1.897 1.279  9.809  HO1  234 35 
234 H8   H8   H 0 1 N N N 28.150 32.038 18.505 -1.427 -0.291 -0.113 H8   234 36 
234 H33  H33  H 0 1 N N N 24.372 32.176 21.342 -2.350 -1.620 -3.726 H33  234 37 
234 H34  H34  H 0 1 N N N 21.932 32.039 21.861 -3.760 -1.646 -5.738 H34  234 38 
234 H35  H35  H 0 1 N N N 20.859 29.824 22.328 -3.054 -0.457 -7.768 H35  234 39 
234 H391 1H39 H 0 0 N N N 25.556 25.023 20.852 4.049  0.443  -6.496 H391 234 40 
234 H392 2H39 H 0 0 N N N 26.700 25.599 19.565 3.177  1.955  -6.849 H392 234 41 
234 H393 3H39 H 0 0 N N N 26.978 25.861 21.340 3.471  1.469  -5.161 H393 234 42 
234 H14  H14  H 0 1 N N N 22.519 26.691 22.329 -0.326 0.282  -8.560 H14  234 43 
234 H401 1H40 H 0 0 N N N 26.395 32.124 20.945 -1.706 -0.715 -2.310 H401 234 44 
234 H402 2H40 H 0 0 N N N 26.105 31.302 19.506 -0.875 -2.185 -2.873 H402 234 45 
234 H41  H41  H 0 1 N N N 28.781 30.431 20.969 1.076  -1.606 -1.250 H41  234 46 
# 
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 
234 C1  C2   DOUB Y N 1  
234 C1  C6   SING Y N 2  
234 C1  F1   SING N N 3  
234 C2  C3   SING Y N 4  
234 C2  C7   SING N N 5  
234 C3  C4   DOUB Y N 6  
234 C3  H3   SING N N 7  
234 C4  C5   SING Y N 8  
234 C4  C8   SING N N 9  
234 C5  C6   DOUB Y N 10 
234 C5  H5   SING N N 11 
234 C6  H6   SING N N 12 
234 C7  O12  SING Y N 13 
234 C7  C15  DOUB Y N 14 
234 O12 N13  SING Y N 15 
234 N13 C14  DOUB Y N 16 
234 C14 C15  SING Y N 17 
234 C14 C16  SING N N 18 
234 C15 H15  SING N N 19 
234 C16 O1   SING N N 20 
234 C16 O2   DOUB N N 21 
234 O1  HO1  SING N N 22 
234 C8  C41  DOUB N E 23 
234 C8  H8   SING N N 24 
234 C32 C33  DOUB Y N 25 
234 C32 C37  SING Y N 26 
234 C32 O3   SING N N 27 
234 C33 C34  SING Y N 28 
234 C33 H33  SING N N 29 
234 C34 C35  DOUB Y N 30 
234 C34 H34  SING N N 31 
234 C35 C36  SING Y N 32 
234 C35 H35  SING N N 33 
234 C36 C37  DOUB Y N 34 
234 C36 O14  SING N N 35 
234 C37 C38  SING N N 36 
234 C38 O11  DOUB N N 37 
234 C38 O4   SING N N 38 
234 O4  C39  SING N N 39 
234 C39 H391 SING N N 40 
234 C39 H392 SING N N 41 
234 C39 H393 SING N N 42 
234 O14 H14  SING N N 43 
234 O3  C40  SING N N 44 
234 C40 C41  SING N N 45 
234 C40 H401 SING N N 46 
234 C40 H402 SING N N 47 
234 C41 H41  SING N N 48 
# 
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 
234 SMILES           ACDLabs              10.04 O=C(O)c3noc(c2c(F)ccc(/C=C/COc1cccc(O)c1C(=O)OC)c2)c3                                                                                                       
234 InChI            InChI                1.02b InChI=1/C21H16FNO7/c1-28-21(27)19-16(24)5-2-6-17(19)29-9-3-4-12-7-8-14(22)13(10-12)18-11-15(20(25)26)23-30-18/h2-8,10-11,24H,9H2,1H3,(H,25,26)/b4-3+/f/h25H 
234 InChIKey         InChI                1.02b QKHWJUMLYAYZFS-CAKMTQNUDZ                                                                                                                                   
234 SMILES_CANONICAL CACTVS               3.341 COC(=O)c1c(O)cccc1OC/C=C/c2ccc(F)c(c2)c3onc(c3)C(O)=O                                                                                                       
234 SMILES           CACTVS               3.341 COC(=O)c1c(O)cccc1OCC=Cc2ccc(F)c(c2)c3onc(c3)C(O)=O                                                                                                         
234 SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 COC(=O)c1c(cccc1OC\C=C\c2ccc(c(c2)c3cc(no3)C(=O)O)F)O                                                                                                       
234 SMILES           "OpenEye OEToolkits" 1.5.0 COC(=O)c1c(cccc1OCC=Cc2ccc(c(c2)c3cc(no3)C(=O)O)F)O                                                                                                         
# 
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 
234 "SYSTEMATIC NAME" ACDLabs              10.04 "5-(2-fluoro-5-{(1E)-3-[3-hydroxy-2-(methoxycarbonyl)phenoxy]prop-1-en-1-yl}phenyl)isoxazole-3-carboxylic acid" 
234 "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "5-[2-fluoro-5-[(E)-3-(3-hydroxy-2-methoxycarbonyl-phenoxy)prop-1-enyl]phenyl]-1,2-oxazole-3-carboxylic acid"   
# 
