data_699
# 
_chem_comp.id                                    699 
_chem_comp.name                                  "(2S,4S,5R)-2-ISOBUTYL-5-(2-THIENYL)-1-[4-(TRIFLUOROMETHYL)BENZOYL]PYRROLIDINE-2,4-DICARBOXYLIC ACID" 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C22 H22 F3 N O5 S" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         ? 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2006-12-18 
_chem_comp.pdbx_modified_date                    2008-10-14 
_chem_comp.pdbx_ambiguous_flag                   ? 
_chem_comp.pdbx_release_status                   REL 
_chem_comp.pdbx_replaced_by                      ? 
_chem_comp.pdbx_replaces                         ? 
_chem_comp.formula_weight                        469.474 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     699 
_chem_comp.pdbx_model_coordinates_details        ? 
_chem_comp.pdbx_model_coordinates_missing_flag   N 
_chem_comp.pdbx_ideal_coordinates_details        "OpenEye/OEToolkits V1.4.2" 
_chem_comp.pdbx_ideal_coordinates_missing_flag   N 
_chem_comp.pdbx_model_coordinates_db_code        2JC0 
_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 
699 F54  F54  F 0 1 N N N 5.441  41.379 51.934 -8.406 -1.135 3.489  F54  699 1  
699 C51  C51  C 0 1 N N N 5.264  42.694 51.608 -8.560 -0.864 2.159  C51  699 2  
699 F52  F52  F 0 1 N N N 4.625  43.357 52.594 -9.758 -0.215 2.065  F52  699 3  
699 F53  F53  F 0 1 N N N 4.661  42.947 50.429 -8.752 -2.075 1.559  F53  699 4  
699 C2   C2   C 0 1 Y N N 6.599  43.415 51.537 -7.421 -0.105 1.568  C2   699 5  
699 C1   C1   C 0 1 Y N N 7.367  43.637 52.720 -6.336 0.258  2.366  C1   699 6  
699 C6   C6   C 0 1 Y N N 8.580  44.353 52.676 -5.270 0.969  1.814  C6   699 7  
699 C3   C3   C 0 1 Y N N 7.042  43.947 50.294 -7.440 0.243  0.218  C3   699 8  
699 C4   C4   C 0 1 Y N N 8.238  44.659 50.256 -6.375 0.953  -0.335 C4   699 9  
699 C5   C5   C 0 1 Y N N 9.028  44.845 51.429 -5.294 1.313  0.466  C5   699 10 
699 C11  C11  C 0 1 N N N 10.297 45.670 51.337 -4.173 2.062  -0.115 C11  699 11 
699 O13  O13  O 0 1 N N N 10.221 46.917 51.554 -4.263 3.289  -0.047 O13  699 12 
699 N12  N12  N 0 1 N N N 11.490 45.101 50.970 -3.088 1.369  -0.667 N12  699 13 
699 C17  C17  C 0 1 N N S 12.805 45.857 50.967 -3.010 -0.062 -1.042 C17  699 14 
699 C34  C34  C 0 1 N N N 12.741 46.992 49.901 -2.660 -0.881 0.170  C34  699 15 
699 O36  O36  O 0 1 N N N 11.825 46.766 49.005 -3.563 -1.875 0.353  O36  699 16 
699 O35  O35  O 0 1 N N N 13.559 47.866 49.747 -1.695 -0.687 0.894  O35  699 17 
699 C33  C33  C 0 1 N N N 13.038 46.453 52.405 -4.267 -0.636 -1.703 C33  699 18 
699 C37  C37  C 0 1 N N N 13.247 45.471 53.585 -4.078 -2.065 -2.234 C37  699 19 
699 C44  C44  C 0 1 N N N 13.844 46.224 54.744 -2.937 -2.167 -3.247 C44  699 20 
699 C40  C40  C 0 1 N N N 11.926 44.847 54.063 -3.818 -3.018 -1.065 C40  699 21 
699 C16  C16  C 0 1 N N N 13.766 44.724 50.466 -1.850 -0.130 -2.062 C16  699 22 
699 C15  C15  C 0 1 N N S 13.101 43.421 50.842 -0.962 1.073  -1.759 C15  699 23 
699 C22  C22  C 0 1 N N N 13.605 42.155 50.166 0.162  0.687  -0.840 C22  699 24 
699 O25  O25  O 0 1 N N N 12.882 41.077 50.530 0.951  1.757  -0.573 O25  699 25 
699 O24  O24  O 0 1 N N N 14.687 42.132 49.622 0.346  -0.433 -0.388 O24  699 26 
699 C14  C14  C 0 1 N N R 11.636 43.676 50.575 -1.945 2.121  -1.220 C14  699 27 
699 C20  C20  C 0 1 Y N N 11.219 43.348 49.164 -1.321 3.104  -0.244 C20  699 28 
699 S29  S29  S 0 1 Y N N 10.230 41.993 48.840 -0.656 4.563  -0.837 S29  699 29 
699 C26  C26  C 0 1 Y N N 11.610 44.043 47.995 -1.204 2.991  1.120  C26  699 30 
699 C27  C27  C 0 1 Y N N 11.015 43.386 46.877 -0.556 4.123  1.692  C27  699 31 
699 C28  C28  C 0 1 Y N N 10.263 42.299 47.164 -0.205 5.055  0.739  C28  699 32 
699 H1   H1   H 0 1 N N N 7.015  43.247 53.690 -6.313 -0.009 3.419  H1   699 33 
699 H3   H3   H 0 1 N N N 6.462  43.808 49.366 -8.281 -0.035 -0.412 H3   699 34 
699 H6   H6   H 0 1 N N N 9.165  44.524 53.596 -4.430 1.245  2.445  H6   699 35 
699 H4   H4   H 0 1 N N N 8.562  45.079 49.289 -6.400 1.218  -1.389 H4   699 36 
699 H14  H14  H 0 1 N N N 10.946 43.012 51.147 -2.348 2.706  -2.058 H14  699 37 
699 H331 1H33 H 0 0 N N N 12.198 47.143 52.652 -5.091 -0.603 -0.982 H331 699 38 
699 H332 2H33 H 0 0 N N N 13.896 47.164 52.368 -4.541 0.025  -2.532 H332 699 39 
699 H161 1H16 H 0 0 N N N 14.808 44.820 50.852 -2.242 -0.018 -3.082 H161 699 40 
699 H162 2H16 H 0 0 N N N 14.017 44.800 49.382 -1.307 -1.082 -2.020 H162 699 41 
699 H36  H36  H 0 1 N N N 11.786 47.458 48.355 -3.351 -2.423 1.139  H36  699 42 
699 H37  H37  H 0 1 N N N 13.917 44.655 53.227 -5.004 -2.385 -2.728 H37  699 43 
699 H441 1H44 H 0 0 N N N 13.236 47.113 55.033 -1.996 -1.801 -2.822 H441 699 44 
699 H442 2H44 H 0 0 N N N 14.781 46.761 54.466 -3.152 -1.587 -4.149 H442 699 45 
699 H443 3H44 H 0 0 N N N 13.994 45.517 55.593 -2.786 -3.206 -3.558 H443 699 46 
699 H401 1H40 H 0 0 N N N 11.384 44.356 53.221 -2.899 -2.752 -0.532 H401 699 47 
699 H402 2H40 H 0 0 N N N 11.179 45.633 54.320 -3.719 -4.050 -1.418 H402 699 48 
699 H403 3H40 H 0 0 N N N 12.076 44.140 54.912 -4.646 -2.990 -0.348 H403 699 49 
699 H15  H15  H 0 1 N N N 13.343 43.178 51.903 -0.475 1.438  -2.672 H15  699 50 
699 H25  H25  H 0 1 N N N 13.197 40.286 50.108 1.691  1.526  0.028  H25  699 51 
699 H26  H26  H 0 1 N N N 12.260 44.934 47.961 -1.564 2.141  1.687  H26  699 52 
699 H28  H28  H 0 1 N N N 9.809  41.806 46.288 0.297  6.000  0.895  H28  699 53 
699 H27  H27  H 0 1 N N N 11.132 43.707 45.828 -0.357 4.247  2.748  H27  699 54 
# 
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 
699 F54 C51  SING N N 1  
699 C51 F52  SING N N 2  
699 C51 F53  SING N N 3  
699 C51 C2   SING N N 4  
699 C2  C1   SING Y N 5  
699 C2  C3   DOUB Y N 6  
699 C1  C6   DOUB Y N 7  
699 C1  H1   SING N N 8  
699 C6  C5   SING Y N 9  
699 C6  H6   SING N N 10 
699 C3  C4   SING Y N 11 
699 C3  H3   SING N N 12 
699 C4  C5   DOUB Y N 13 
699 C4  H4   SING N N 14 
699 C5  C11  SING N N 15 
699 C11 O13  DOUB N N 16 
699 C11 N12  SING N N 17 
699 N12 C17  SING N N 18 
699 N12 C14  SING N N 19 
699 C17 C34  SING N N 20 
699 C17 C33  SING N N 21 
699 C17 C16  SING N N 22 
699 C34 O36  SING N N 23 
699 C34 O35  DOUB N N 24 
699 O36 H36  SING N N 25 
699 C33 C37  SING N N 26 
699 C33 H331 SING N N 27 
699 C33 H332 SING N N 28 
699 C37 C44  SING N N 29 
699 C37 C40  SING N N 30 
699 C37 H37  SING N N 31 
699 C44 H441 SING N N 32 
699 C44 H442 SING N N 33 
699 C44 H443 SING N N 34 
699 C40 H401 SING N N 35 
699 C40 H402 SING N N 36 
699 C40 H403 SING N N 37 
699 C16 C15  SING N N 38 
699 C16 H161 SING N N 39 
699 C16 H162 SING N N 40 
699 C15 C22  SING N N 41 
699 C15 C14  SING N N 42 
699 C15 H15  SING N N 43 
699 C22 O25  SING N N 44 
699 C22 O24  DOUB N N 45 
699 O25 H25  SING N N 46 
699 C14 C20  SING N N 47 
699 C14 H14  SING N N 48 
699 C20 S29  SING Y N 49 
699 C20 C26  DOUB Y N 50 
699 S29 C28  SING Y N 51 
699 C26 C27  SING Y N 52 
699 C26 H26  SING N N 53 
699 C27 C28  DOUB Y N 54 
699 C27 H27  SING N N 55 
699 C28 H28  SING N N 56 
# 
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 
699 SMILES           ACDLabs              10.04 FC(F)(F)c1ccc(cc1)C(=O)N2C(C(=O)O)(CC(C(=O)O)C2c3sccc3)CC(C)C                                                                                                                                      
699 InChI            InChI                1.02b InChI=1/C22H22F3NO5S/c1-12(2)10-21(20(30)31)11-15(19(28)29)17(16-4-3-9-32-16)26(21)18(27)13-5-7-14(8-6-13)22(23,24)25/h3-9,12,15,17H,10-11H2,1-2H3,(H,28,29)(H,30,31)/t15-,17+,21-/m0/s1/f/h28,30H 
699 InChIKey         InChI                1.02b ZNCZVHCYBGHCHA-IYXOVQEUDI                                                                                                                                                                          
699 SMILES_CANONICAL CACTVS               3.341 CC(C)C[C@]1(C[C@@H]([C@@H](N1C(=O)c2ccc(cc2)C(F)(F)F)c3sccc3)C(O)=O)C(O)=O                                                                                                                         
699 SMILES           CACTVS               3.341 CC(C)C[C]1(C[CH]([CH](N1C(=O)c2ccc(cc2)C(F)(F)F)c3sccc3)C(O)=O)C(O)=O                                                                                                                              
699 SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 CC(C)C[C@]1(C[C@@H]([C@@H](N1C(=O)c2ccc(cc2)C(F)(F)F)c3cccs3)C(=O)O)C(=O)O                                                                                                                         
699 SMILES           "OpenEye OEToolkits" 1.5.0 CC(C)CC1(CC(C(N1C(=O)c2ccc(cc2)C(F)(F)F)c3cccs3)C(=O)O)C(=O)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 
699 "SYSTEMATIC NAME" ACDLabs              10.04 "(2S,4S,5R)-2-(2-methylpropyl)-5-thiophen-2-yl-1-{[4-(trifluoromethyl)phenyl]carbonyl}pyrrolidine-2,4-dicarboxylic acid" 
699 "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "(2S,4S,5R)-2-(2-methylpropyl)-5-thiophen-2-yl-1-[4-(trifluoromethyl)phenyl]carbonyl-pyrrolidine-2,4-dicarboxylic acid"  
# 
