data_RYU
# 
_chem_comp.id                                    RYU 
_chem_comp.name                                  "(2E,3S)-3-HYDROXY-5'-[(4-HYDROXYPIPERIDIN-1-YL)SULFONYL]-3-METHYL-1,3-DIHYDRO-2,3'-BIINDOL-2'(1'H)-ONE" 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C22 H23 N3 O5 S" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         ? 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2005-01-11 
_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                        441.500 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     RYU 
_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        2BHH 
_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 
RYU C1   C1   C 0 1 Y N N 3.825  24.406 7.696  3.071  0.645  -3.860 C1   RYU 1  
RYU C2   C2   C 0 1 Y N N 5.096  24.090 7.067  3.672  0.396  -5.082 C2   RYU 2  
RYU C3   C3   C 0 1 Y N N 5.496  24.694 5.807  2.957  -0.229 -6.086 C3   RYU 3  
RYU C4   C4   C 0 1 Y N N 4.758  25.817 5.250  1.647  -0.608 -5.877 C4   RYU 4  
RYU C5   C5   C 0 1 Y N N 3.588  26.250 5.990  1.034  -0.361 -4.649 C5   RYU 5  
RYU C6   C6   C 0 1 Y N N 3.069  25.489 7.103  1.766  0.269  -3.646 C6   RYU 6  
RYU C7   C7   C 0 1 N N S 1.766  25.991 7.489  0.841  0.394  -2.458 C7   RYU 7  
RYU C71  C71  C 0 1 N N N 1.769  26.231 8.974  0.625  1.866  -2.100 C71  RYU 8  
RYU O71  O71  O 0 1 N N N 0.809  25.103 7.207  1.367  -0.318 -1.337 O71  RYU 9  
RYU C8   C8   C 0 1 N N N 1.714  27.198 6.676  -0.454 -0.233 -2.925 C8   RYU 10 
RYU N9   N9   N 0 1 N N N 2.776  27.383 5.761  -0.255 -0.644 -4.204 N9   RYU 11 
RYU C10  C10  C 0 1 N N N 0.725  28.249 6.797  -1.602 -0.361 -2.199 C10  RYU 12 
RYU C11  C11  C 0 1 N N N 0.855  29.681 6.329  -2.906 -0.844 -2.669 C11  RYU 13 
RYU O11  O11  O 0 1 N N N 1.776  30.013 5.589  -3.167 -1.211 -3.801 O11  RYU 14 
RYU N12  N12  N 0 1 N N N -0.018 30.578 6.773  -3.760 -0.812 -1.633 N12  RYU 15 
RYU C13  C13  C 0 1 Y N N -0.807 29.774 7.628  -3.142 -0.341 -0.481 C13  RYU 16 
RYU C14  C14  C 0 1 Y N N -0.431 28.372 7.658  -1.802 -0.050 -0.765 C14  RYU 17 
RYU C15  C15  C 0 1 Y N N -1.055 27.351 8.485  -0.965 0.445  0.228  C15  RYU 18 
RYU C16  C16  C 0 1 Y N N -1.975 27.886 9.469  -1.456 0.639  1.503  C16  RYU 19 
RYU C17  C17  C 0 1 Y N N -2.455 29.259 9.404  -2.779 0.347  1.789  C17  RYU 20 
RYU C18  C18  C 0 1 Y N N -1.878 30.234 8.490  -3.620 -0.139 0.809  C18  RYU 21 
RYU S19  S19  S 0 1 N N N -2.562 27.004 10.927 -0.399 1.260  2.768  S19  RYU 22 
RYU O19  O19  O 0 1 N N N -1.514 27.557 12.212 0.651  1.939  2.094  O19  RYU 23 
RYU O1   O1   O 0 1 N N N -4.158 27.658 10.824 -1.259 1.836  3.742  O1   RYU 24 
RYU N20  N20  N 0 1 N N N -2.512 25.242 11.153 0.307  -0.042 3.507  N20  RYU 25 
RYU C21  C21  C 0 1 N N N -2.302 24.618 12.479 1.583  -0.580 3.016  C21  RYU 26 
RYU C22  C22  C 0 1 N N N -1.004 23.819 12.532 2.574  -0.641 4.182  C22  RYU 27 
RYU C23  C23  C 0 1 N N N -0.836 22.868 11.344 1.955  -1.441 5.331  C23  RYU 28 
RYU O23  O23  O 0 1 N N N 0.349  22.064 11.374 2.889  -1.528 6.409  O23  RYU 29 
RYU C24  C24  C 0 1 N N N -1.071 23.592 10.020 0.682  -0.742 5.814  C24  RYU 30 
RYU C25  C25  C 0 1 N N N -2.385 24.350 9.992  -0.326 -0.678 4.669  C25  RYU 31 
RYU H1   H1   H 0 1 N N N 3.457  23.852 8.576  3.627  1.134  -3.074 H1   RYU 32 
RYU H2   H2   H 0 1 N N N 5.775  23.373 7.558  4.697  0.691  -5.250 H2   RYU 33 
RYU H3   H3   H 0 1 N N N 6.371  24.296 5.266  3.426  -0.423 -7.039 H3   RYU 34 
RYU H4   H4   H 0 1 N N N 5.071  26.312 4.316  1.095  -1.097 -6.666 H4   RYU 35 
RYU H711 1H71 H 0 0 N N N 0.766  26.617 9.271  1.549  2.282  -1.698 H711 RYU 36 
RYU H712 2H71 H 0 0 N N N 2.599  26.901 9.298  0.337  2.419  -2.995 H712 RYU 37 
RYU H713 3H71 H 0 0 N N N 2.068  25.327 9.553  -0.164 1.947  -1.354 H713 RYU 38 
RYU H71  H71  H 0 1 N N N -0.045 25.432 7.460  2.204  0.106  -1.103 H71  RYU 39 
RYU H9   H9   H 0 1 N N N 2.920  28.146 5.099  -0.931 -1.083 -4.744 H9   RYU 40 
RYU H12  H12  H 0 1 N N N -0.097 31.572 6.557  -4.691 -1.082 -1.682 H12  RYU 41 
RYU H15  H15  H 0 1 N N N -0.848 26.273 8.374  0.066  0.673  0.004  H15  RYU 42 
RYU H17  H17  H 0 1 N N N -3.280 29.569 10.067 -3.157 0.501  2.789  H17  RYU 43 
RYU H18  H18  H 0 1 N N N -2.239 31.276 8.455  -4.650 -0.363 1.044  H18  RYU 44 
RYU H211 1H21 H 0 0 N N N -3.176 23.992 12.775 1.428  -1.581 2.615  H211 RYU 45 
RYU H212 2H21 H 0 0 N N N -2.345 25.376 13.295 1.977  0.070  2.235  H212 RYU 46 
RYU H221 1H22 H 0 0 N N N -0.915 23.268 13.498 3.493  -1.127 3.854  H221 RYU 47 
RYU H222 2H22 H 0 0 N N N -0.124 24.497 12.626 2.798  0.369  4.523  H222 RYU 48 
RYU H23  H23  H 0 1 N N N -1.679 22.144 11.432 1.708  -2.444 4.983  H23  RYU 49 
RYU HA   HA   H 0 1 N N N 0.453  21.474 10.637 2.461  -2.038 7.109  HA   RYU 50 
RYU H241 1H24 H 0 0 N N N -0.216 24.264 9.775  0.255  -1.300 6.647  H241 RYU 51 
RYU H242 2H24 H 0 0 N N N -0.998 22.886 9.160  0.924  0.269  6.139  H242 RYU 52 
RYU H251 1H25 H 0 0 N N N -2.517 24.904 9.034  -1.194 -0.095 4.979  H251 RYU 53 
RYU H252 2H25 H 0 0 N N N -3.255 23.657 9.911  -0.639 -1.688 4.401  H252 RYU 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 
RYU C1  C2   DOUB Y N 1  
RYU C1  C6   SING Y N 2  
RYU C1  H1   SING N N 3  
RYU C2  C3   SING Y N 4  
RYU C2  H2   SING N N 5  
RYU C3  C4   DOUB Y N 6  
RYU C3  H3   SING N N 7  
RYU C4  C5   SING Y N 8  
RYU C4  H4   SING N N 9  
RYU C5  C6   DOUB Y N 10 
RYU C5  N9   SING N N 11 
RYU C6  C7   SING N N 12 
RYU C7  C71  SING N N 13 
RYU C7  O71  SING N N 14 
RYU C7  C8   SING N N 15 
RYU C71 H711 SING N N 16 
RYU C71 H712 SING N N 17 
RYU C71 H713 SING N N 18 
RYU O71 H71  SING N N 19 
RYU C8  N9   SING N N 20 
RYU C8  C10  DOUB N Z 21 
RYU N9  H9   SING N N 22 
RYU C10 C11  SING N N 23 
RYU C10 C14  SING N N 24 
RYU C11 O11  DOUB N N 25 
RYU C11 N12  SING N N 26 
RYU N12 C13  SING N N 27 
RYU N12 H12  SING N N 28 
RYU C13 C14  DOUB Y N 29 
RYU C13 C18  SING Y N 30 
RYU C14 C15  SING Y N 31 
RYU C15 C16  DOUB Y N 32 
RYU C15 H15  SING N N 33 
RYU C16 C17  SING Y N 34 
RYU C16 S19  SING N N 35 
RYU C17 C18  DOUB Y N 36 
RYU C17 H17  SING N N 37 
RYU C18 H18  SING N N 38 
RYU S19 O19  DOUB N N 39 
RYU S19 O1   DOUB N N 40 
RYU S19 N20  SING N N 41 
RYU N20 C21  SING N N 42 
RYU N20 C25  SING N N 43 
RYU C21 C22  SING N N 44 
RYU C21 H211 SING N N 45 
RYU C21 H212 SING N N 46 
RYU C22 C23  SING N N 47 
RYU C22 H221 SING N N 48 
RYU C22 H222 SING N N 49 
RYU C23 O23  SING N N 50 
RYU C23 C24  SING N N 51 
RYU C23 H23  SING N N 52 
RYU O23 HA   SING N N 53 
RYU C24 C25  SING N N 54 
RYU C24 H241 SING N N 55 
RYU C24 H242 SING N N 56 
RYU C25 H251 SING N N 57 
RYU C25 H252 SING N N 58 
# 
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 
RYU SMILES           ACDLabs              10.04 O=S(=O)(c4cc3\C(=C2\Nc1ccccc1C2(O)C)C(=O)Nc3cc4)N5CCC(O)CC5                                                                                                                                 
RYU InChI            InChI                1.02b InChI=1/C22H23N3O5S/c1-22(28)16-4-2-3-5-18(16)23-20(22)19-15-12-14(6-7-17(15)24-21(19)27)31(29,30)25-10-8-13(26)9-11-25/h2-7,12-13,23,26,28H,8-11H2,1H3,(H,24,27)/b20-19-/t22-/m0/s1/f/h24H 
RYU InChIKey         InChI                1.02b AYOAIABDFUJDKQ-RIZUXENUDX                                                                                                                                                                   
RYU SMILES_CANONICAL CACTVS               3.341 C[C@@]1(O)\C(Nc2ccccc12)=C3\C(=O)Nc4ccc(cc34)[S](=O)(=O)N5CCC(O)CC5                                                                                                                         
RYU SMILES           CACTVS               3.341 C[C]1(O)C(Nc2ccccc12)=C3C(=O)Nc4ccc(cc34)[S](=O)(=O)N5CCC(O)CC5                                                                                                                             
RYU SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 C[C@@]1(c2ccccc2NC1=C3c4cc(ccc4NC3=O)S(=O)(=O)N5CCC(CC5)O)O                                                                                                                                 
RYU SMILES           "OpenEye OEToolkits" 1.5.0 CC1(c2ccccc2NC1=C3c4cc(ccc4NC3=O)S(=O)(=O)N5CCC(CC5)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 
RYU "SYSTEMATIC NAME" ACDLabs              10.04 "(2Z,3S)-3-hydroxy-5'-[(4-hydroxypiperidin-1-yl)sulfonyl]-3-methyl-1,3-dihydro-2,3'-biindol-2'(1'H)-one" 
RYU "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 3-[(3S)-3-hydroxy-3-methyl-1H-indol-2-ylidene]-5-(4-hydroxypiperidin-1-yl)sulfonyl-1H-indol-2-one        
# 
