data_RP4
# 
_chem_comp.id                                    RP4 
_chem_comp.name                                  "(1S,4S,5S)-1,4,5-TRIHYDROXY-3-[3-(PHENYLTHIO)PHENYL]CYCLOHEX-2-ENE-1-CARBOXYLIC ACID" 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C19 H18 O5 S" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         ? 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2006-03-31 
_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                        358.408 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     RP4 
_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        ? 
_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 
RP4 O3   O3   O 0 1 N N N 169.211 108.213 -0.621 -2.286 -3.017 0.097  O3   RP4 1  
RP4 C2   C2   C 0 1 N N N 169.085 108.425 0.596  -2.514 -2.309 -0.856 C2   RP4 2  
RP4 O1   O1   O 0 1 N N N 167.931 108.246 1.189  -2.508 -2.828 -2.094 O1   RP4 3  
RP4 C4   C4   C 0 1 N N R 170.161 108.878 1.562  -2.805 -0.844 -0.655 C4   RP4 4  
RP4 O5   O5   O 0 1 N N N 169.973 108.055 2.740  -3.773 -0.417 -1.615 O5   RP4 5  
RP4 C12  C12  C 0 1 N N N 171.589 108.611 1.085  -3.359 -0.627 0.755  C12  RP4 6  
RP4 C10  C10  C 0 1 N N R 172.608 109.214 2.037  -3.405 0.881  1.032  C10  RP4 7  
RP4 O11  O11  O 0 1 N N N 173.903 108.824 1.607  -4.081 1.122  2.268  O11  RP4 8  
RP4 C8   C8   C 0 1 N N R 172.483 110.732 2.014  -1.971 1.408  1.119  C8   RP4 9  
RP4 O9   O9   O 0 1 N N N 172.940 111.208 3.277  -1.985 2.836  1.136  O9   RP4 10 
RP4 C7   C7   C 0 1 N N N 171.077 111.229 1.853  -1.174 0.931  -0.062 C7   RP4 11 
RP4 C6   C6   C 0 1 N N N 170.024 110.370 1.826  -1.540 -0.059 -0.840 C6   RP4 12 
RP4 C13  C13  C 0 1 Y N N 170.889 112.720 1.768  0.095  1.624  -0.368 C13  RP4 13 
RP4 C25  C25  C 0 1 Y N N 172.008 113.576 1.643  0.086  2.965  -0.755 C25  RP4 14 
RP4 C24  C24  C 0 1 Y N N 171.868 114.977 1.580  1.272  3.610  -1.040 C24  RP4 15 
RP4 C23  C23  C 0 1 Y N N 170.592 115.558 1.644  2.473  2.933  -0.943 C23  RP4 16 
RP4 C15  C15  C 0 1 Y N N 169.486 114.699 1.769  2.493  1.597  -0.557 C15  RP4 17 
RP4 C14  C14  C 0 1 Y N N 169.621 113.296 1.844  1.306  0.942  -0.264 C14  RP4 18 
RP4 S16  S16  S 0 1 N N N 167.936 115.351 1.841  4.027  0.739  -0.434 S16  RP4 19 
RP4 C17  C17  C 0 1 Y N N 167.607 116.592 0.734  3.469  -0.791 0.238  C17  RP4 20 
RP4 C22  C22  C 0 1 Y N N 166.986 116.283 -0.473 3.190  -1.861 -0.604 C22  RP4 21 
RP4 C21  C21  C 0 1 Y N N 166.695 117.295 -1.388 2.753  -3.059 -0.074 C21  RP4 22 
RP4 C20  C20  C 0 1 Y N N 167.040 118.606 -1.069 2.593  -3.194 1.293  C20  RP4 23 
RP4 C19  C19  C 0 1 Y N N 167.649 118.918 0.135  2.869  -2.131 2.134  C19  RP4 24 
RP4 C18  C18  C 0 1 Y N N 167.918 117.909 1.044  3.311  -0.933 1.611  C18  RP4 25 
RP4 H1   H1   H 0 1 N N N 167.290 107.952 0.553  -2.321 -3.768 -2.223 H1   RP4 26 
RP4 H5   H5   H 0 1 N N N 169.932 107.141 2.485  -3.387 -0.571 -2.488 H5   RP4 27 
RP4 H121 1H12 H 0 0 N N N 171.719 109.074 0.096  -2.709 -1.113 1.483  H121 RP4 28 
RP4 H122 2H12 H 0 0 N N N 171.750 107.524 1.033  -4.364 -1.042 0.822  H122 RP4 29 
RP4 H10  H10  H 0 1 N N N 172.434 108.861 3.064  -3.932 1.386  0.222  H10  RP4 30 
RP4 H11  H11  H 0 1 N N N 173.910 108.737 0.661  -4.081 2.079  2.404  H11  RP4 31 
RP4 H8   H8   H 0 1 N N N 173.064 111.092 1.152  -1.512 1.039  2.036  H8   RP4 32 
RP4 H9   H9   H 0 1 N N N 173.042 110.476 3.874  -1.064 3.124  1.204  H9   RP4 33 
RP4 H6   H6   H 0 1 N N N 169.036 110.769 2.002  -0.892 -0.325 -1.662 H6   RP4 34 
RP4 H25  H25  H 0 1 N N N 172.997 113.144 1.595  -0.851 3.498  -0.833 H25  RP4 35 
RP4 H24  H24  H 0 1 N N N 172.742 115.603 1.482  1.262  4.647  -1.341 H24  RP4 36 
RP4 H23  H23  H 0 1 N N N 170.464 116.629 1.599  3.398  3.442  -1.167 H23  RP4 37 
RP4 H14  H14  H 0 1 N N N 168.747 112.672 1.960  1.320  -0.096 0.036  H14  RP4 38 
RP4 H22  H22  H 0 1 N N N 166.729 115.259 -0.701 3.315  -1.756 -1.672 H22  RP4 39 
RP4 H21  H21  H 0 1 N N N 166.211 117.066 -2.326 2.536  -3.891 -0.727 H21  RP4 40 
RP4 H20  H20  H 0 1 N N N 166.828 119.395 -1.775 2.251  -4.132 1.706  H20  RP4 41 
RP4 H19  H19  H 0 1 N N N 167.912 119.940 0.363  2.741  -2.240 3.201  H19  RP4 42 
RP4 H18  H18  H 0 1 N N N 168.370 118.147 1.995  3.527  -0.103 2.268  H18  RP4 43 
# 
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 
RP4 O3  C2   DOUB N N 1  
RP4 C2  O1   SING N N 2  
RP4 C2  C4   SING N N 3  
RP4 O1  H1   SING N N 4  
RP4 C4  O5   SING N N 5  
RP4 C4  C12  SING N N 6  
RP4 C4  C6   SING N N 7  
RP4 O5  H5   SING N N 8  
RP4 C12 C10  SING N N 9  
RP4 C12 H121 SING N N 10 
RP4 C12 H122 SING N N 11 
RP4 C10 O11  SING N N 12 
RP4 C10 C8   SING N N 13 
RP4 C10 H10  SING N N 14 
RP4 O11 H11  SING N N 15 
RP4 C8  O9   SING N N 16 
RP4 C8  C7   SING N N 17 
RP4 C8  H8   SING N N 18 
RP4 O9  H9   SING N N 19 
RP4 C7  C6   DOUB N N 20 
RP4 C7  C13  SING N N 21 
RP4 C6  H6   SING N N 22 
RP4 C13 C25  DOUB Y N 23 
RP4 C13 C14  SING Y N 24 
RP4 C25 C24  SING Y N 25 
RP4 C25 H25  SING N N 26 
RP4 C24 C23  DOUB Y N 27 
RP4 C24 H24  SING N N 28 
RP4 C23 C15  SING Y N 29 
RP4 C23 H23  SING N N 30 
RP4 C15 C14  DOUB Y N 31 
RP4 C15 S16  SING N N 32 
RP4 C14 H14  SING N N 33 
RP4 S16 C17  SING N N 34 
RP4 C17 C22  DOUB Y N 35 
RP4 C17 C18  SING Y N 36 
RP4 C22 C21  SING Y N 37 
RP4 C22 H22  SING N N 38 
RP4 C21 C20  DOUB Y N 39 
RP4 C21 H21  SING N N 40 
RP4 C20 C19  SING Y N 41 
RP4 C20 H20  SING N N 42 
RP4 C19 C18  DOUB Y N 43 
RP4 C19 H19  SING N N 44 
RP4 C18 H18  SING N N 45 
# 
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 
RP4 SMILES           ACDLabs              10.04 O=C(O)C3(O)C=C(c2cccc(Sc1ccccc1)c2)C(O)C(O)C3                                                                                                                
RP4 InChI            InChI                1.02b InChI=1/C19H18O5S/c20-16-11-19(24,18(22)23)10-15(17(16)21)12-5-4-8-14(9-12)25-13-6-2-1-3-7-13/h1-10,16-17,20-21,24H,11H2,(H,22,23)/t16-,17-,19+/m1/s1/f/h22H 
RP4 InChIKey         InChI                1.02b QMNMNSINKIFYBV-QPLKNTIUDY                                                                                                                                    
RP4 SMILES_CANONICAL CACTVS               3.341 O[C@@H]1C[C@@](O)(C=C([C@H]1O)c2cccc(Sc3ccccc3)c2)C(O)=O                                                                                                     
RP4 SMILES           CACTVS               3.341 O[CH]1C[C](O)(C=C([CH]1O)c2cccc(Sc3ccccc3)c2)C(O)=O                                                                                                          
RP4 SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 c1ccc(cc1)Sc2cccc(c2)C3=C[C@](C[C@H]([C@@H]3O)O)(C(=O)O)O                                                                                                    
RP4 SMILES           "OpenEye OEToolkits" 1.5.0 c1ccc(cc1)Sc2cccc(c2)C3=CC(CC(C3O)O)(C(=O)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 
RP4 "SYSTEMATIC NAME" ACDLabs              10.04 "(1R,4R,5R)-1,4,5-trihydroxy-3-[3-(phenylsulfanyl)phenyl]cyclohex-2-ene-1-carboxylic acid" 
RP4 "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "(1R,4R,5R)-1,4,5-trihydroxy-3-(3-phenylsulfanylphenyl)cyclohex-2-ene-1-carboxylic acid"   
# 
