data_LS3
# 
_chem_comp.id                                    LS3 
_chem_comp.name                                  3-{[(2,2-DIOXIDO-1,3-DIHYDRO-2-BENZOTHIEN-5-YL)AMINO]METHYLENE}-5-(1,3-OXAZOL-5-YL)-1,3-DIHYDRO-2H-INDOL-2-ONE 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C20 H15 N3 O4 S" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         ? 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2001-11-21 
_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                        393.416 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     LS3 
_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        1KE7 
_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 
LS3 O5   O5   O 0 1 N N N -10.910 52.353 11.763 3.725  0.037  0.647  O5   LS3 1  
LS3 C6   C6   C 0 1 N N N -10.187 51.869 12.620 2.980  0.020  1.611  C6   LS3 2  
LS3 N7   N7   N 0 1 N N N -9.642  52.527 13.699 3.358  -0.012 2.900  N7   LS3 3  
LS3 C8   C8   C 0 1 Y N N -8.813  51.686 14.393 2.260  -0.024 3.751  C8   LS3 4  
LS3 C9   C9   C 0 1 Y N N -7.997  51.908 15.613 2.168  -0.055 5.141  C9   LS3 5  
LS3 C10  C10  C 0 1 Y N N -7.134  50.793 16.109 0.937  -0.061 5.755  C10  LS3 6  
LS3 C11  C11  C 0 1 Y N N -7.015  49.494 15.355 -0.235 -0.036 4.994  C11  LS3 7  
LS3 C12  C12  C 0 1 Y N N -6.139  48.427 15.820 -1.554 -0.043 5.663  C12  LS3 8  
LS3 O13  O13  O 0 1 Y N N -5.834  48.223 17.142 -2.645 0.665  5.299  O13  LS3 9  
LS3 C14  C14  C 0 1 Y N N -5.182  47.017 17.181 -3.627 0.374  6.163  C14  LS3 10 
LS3 N15  N15  N 0 1 Y N N -4.876  46.575 15.941 -3.182 -0.481 7.040  N15  LS3 11 
LS3 C16  C16  C 0 1 Y N N -5.464  47.414 15.061 -1.902 -0.767 6.757  C16  LS3 12 
LS3 C17  C17  C 0 1 Y N N -7.873  49.331 14.139 -0.157 -0.005 3.603  C17  LS3 13 
LS3 C18  C18  C 0 1 Y N N -8.792  50.406 13.706 1.086  0.000  2.986  C18  LS3 14 
LS3 C19  C19  C 0 1 N N N -9.753  50.438 12.623 1.514  0.036  1.567  C19  LS3 15 
LS3 C20  C20  C 0 1 N N N -10.173 49.412 11.846 0.716  0.074  0.460  C20  LS3 16 
LS3 N21  N21  N 0 1 N N N -10.942 49.382 10.582 1.276  0.104  -0.780 N21  LS3 17 
LS3 C22  C22  C 0 1 Y N N -11.117 48.283 9.773  0.459  0.144  -1.913 C22  LS3 18 
LS3 C23  C23  C 0 1 Y N N -10.010 47.344 9.394  1.020  0.179  -3.176 C23  LS3 19 
LS3 C24  C24  C 0 1 Y N N -10.297 46.197 8.533  0.222  0.214  -4.323 C24  LS3 20 
LS3 C25  C25  C 0 1 N N N -9.336  45.163 8.091  0.776  0.249  -5.748 C25  LS3 21 
LS3 S26  S26  S 0 1 N N N -9.921  44.450 6.562  -0.706 -0.194 -6.741 S26  LS3 22 
LS3 O27  O27  O 0 1 N N N -9.684  43.032 6.511  -0.736 -1.600 -6.944 O27  LS3 23 
LS3 O28  O28  O 0 1 N N N -9.457  45.308 5.509  -0.810 0.682  -7.855 O28  LS3 24 
LS3 C29  C29  C 0 1 N N N -11.631 44.871 6.985  -1.963 0.268  -5.481 C29  LS3 25 
LS3 C30  C30  C 0 1 Y N N -11.638 45.995 7.968  -1.145 0.223  -4.189 C30  LS3 26 
LS3 C31  C31  C 0 1 Y N N -12.762 46.882 8.351  -1.708 0.193  -2.909 C31  LS3 27 
LS3 C32  C32  C 0 1 Y N N -12.488 48.036 9.241  -0.923 0.153  -1.782 C32  LS3 28 
LS3 H7N  NH7  H 0 1 N N N -9.826  53.499 13.949 4.281  -0.025 3.199  H7N  LS3 29 
LS3 H91  1H9  H 0 1 N N N -8.031  52.878 16.138 3.067  -0.075 5.738  H91  LS3 30 
LS3 H101 1H10 H 0 0 N N N -6.574  50.931 17.049 0.876  -0.085 6.833  H101 LS3 31 
LS3 H141 1H14 H 0 0 N N N -4.932  46.466 18.103 -4.626 0.783  6.138  H141 LS3 32 
LS3 H161 1H16 H 0 0 N N N -5.406  47.298 13.966 -1.263 -1.444 7.305  H161 LS3 33 
LS3 H171 1H17 H 0 0 N N N -7.827  48.400 13.550 -1.058 0.014  3.009  H171 LS3 34 
LS3 H201 1H20 H 0 0 N N N -9.842  48.467 12.308 -0.357 0.082  0.569  H201 LS3 35 
LS3 H21N NH21 H 0 0 N N N -10.555 50.118 9.991  2.241  0.098  -0.877 H21N LS3 36 
LS3 H231 1H23 H 0 0 N N N -8.978  47.498 9.751  2.095  0.177  -3.279 H231 LS3 37 
LS3 H251 1H25 H 0 0 N N N -9.148  44.393 8.875  1.566  -0.489 -5.877 H251 LS3 38 
LS3 H252 2H25 H 0 0 N N N -8.296  45.556 8.007  1.131  1.247  -6.003 H252 LS3 39 
LS3 H291 1H29 H 0 0 N N N -12.204 43.988 7.351  -2.774 -0.459 -5.454 H291 LS3 40 
LS3 H292 2H29 H 0 0 N N N -12.245 45.097 6.082  -2.348 1.271  -5.664 H292 LS3 41 
LS3 H311 1H31 H 0 0 N N N -13.783 46.687 7.981  -2.783 0.200  -2.804 H311 LS3 42 
LS3 H321 1H32 H 0 0 N N N -13.312 48.718 9.510  -1.377 0.129  -0.802 H321 LS3 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 
LS3 O5  C6   DOUB N N 1  
LS3 C6  N7   SING N N 2  
LS3 C6  C19  SING N N 3  
LS3 N7  C8   SING N N 4  
LS3 N7  H7N  SING N N 5  
LS3 C8  C9   DOUB Y N 6  
LS3 C8  C18  SING Y N 7  
LS3 C9  C10  SING Y N 8  
LS3 C9  H91  SING N N 9  
LS3 C10 C11  DOUB Y N 10 
LS3 C10 H101 SING N N 11 
LS3 C11 C12  SING N N 12 
LS3 C11 C17  SING Y N 13 
LS3 C12 O13  SING Y N 14 
LS3 C12 C16  DOUB Y N 15 
LS3 O13 C14  SING Y N 16 
LS3 C14 N15  DOUB Y N 17 
LS3 C14 H141 SING N N 18 
LS3 N15 C16  SING Y N 19 
LS3 C16 H161 SING N N 20 
LS3 C17 C18  DOUB Y N 21 
LS3 C17 H171 SING N N 22 
LS3 C18 C19  SING N N 23 
LS3 C19 C20  DOUB N Z 24 
LS3 C20 N21  SING N N 25 
LS3 C20 H201 SING N N 26 
LS3 N21 C22  SING N N 27 
LS3 N21 H21N SING N N 28 
LS3 C22 C23  DOUB Y N 29 
LS3 C22 C32  SING Y N 30 
LS3 C23 C24  SING Y N 31 
LS3 C23 H231 SING N N 32 
LS3 C24 C25  SING N N 33 
LS3 C24 C30  DOUB Y N 34 
LS3 C25 S26  SING N N 35 
LS3 C25 H251 SING N N 36 
LS3 C25 H252 SING N N 37 
LS3 S26 O27  DOUB N N 38 
LS3 S26 O28  DOUB N N 39 
LS3 S26 C29  SING N N 40 
LS3 C29 C30  SING N N 41 
LS3 C29 H291 SING N N 42 
LS3 C29 H292 SING N N 43 
LS3 C30 C31  SING Y N 44 
LS3 C31 C32  DOUB Y N 45 
LS3 C31 H311 SING N N 46 
LS3 C32 H321 SING N N 47 
# 
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 
LS3 SMILES           ACDLabs              10.04 O=C3Nc2ccc(c1ocnc1)cc2/C3=C/Nc4ccc5c(c4)CS(=O)(=O)C5                                                                                                      
LS3 InChI            InChI                1.02b InChI=1/C20H15N3O4S/c24-20-17(7-22-15-3-1-13-9-28(25,26)10-14(13)5-15)16-6-12(2-4-18(16)23-20)19-8-21-11-27-19/h1-8,11,22H,9-10H2,(H,23,24)/b17-7-/f/h23H 
LS3 InChIKey         InChI                1.02b FTQYGMLRLRXBPT-NXRJOORFDQ                                                                                                                                 
LS3 SMILES_CANONICAL CACTVS               3.341 O=C\1Nc2ccc(cc2C\1=C/Nc3ccc4C[S](=O)(=O)Cc4c3)c5ocnc5                                                                                                     
LS3 SMILES           CACTVS               3.341 O=C1Nc2ccc(cc2C1=CNc3ccc4C[S](=O)(=O)Cc4c3)c5ocnc5                                                                                                        
LS3 SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 c1cc2c(cc1c3cnco3)C(=CNc4ccc5c(c4)CS(=O)(=O)C5)C(=O)N2                                                                                                    
LS3 SMILES           "OpenEye OEToolkits" 1.5.0 c1cc2c(cc1c3cnco3)C(=CNc4ccc5c(c4)CS(=O)(=O)C5)C(=O)N2                                                                                                    
# 
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 
LS3 "SYSTEMATIC NAME" ACDLabs              10.04 (3Z)-3-{[(2,2-dioxido-1,3-dihydro-2-benzothiophen-5-yl)amino]methylidene}-5-(1,3-oxazol-5-yl)-1,3-dihydro-2H-indol-2-one 
LS3 "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 3-[[(2,2-dioxo-1,3-dihydro-2-benzothiophen-5-yl)amino]methylidene]-5-(1,3-oxazol-5-yl)-1H-indol-2-one                    
# 
