data_OB3
# 
_chem_comp.id                                    OB3 
_chem_comp.name                                  "(1S,2R,4S)-N-(2-chlorophenyl)-5,6-bis(4-hydroxyphenyl)-N-methyl-7-oxabicyclo[2.2.1]hept-5-ene-2-sulfonamide" 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C25 H22 Cl 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                     2015-05-21 
_chem_comp.pdbx_modified_date                    2016-05-27 
_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                        483.964 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     OB3 
_chem_comp.pdbx_model_coordinates_details        ? 
_chem_comp.pdbx_model_coordinates_missing_flag   N 
_chem_comp.pdbx_ideal_coordinates_details        Corina 
_chem_comp.pdbx_ideal_coordinates_missing_flag   N 
_chem_comp.pdbx_model_coordinates_db_code        4ZWH 
_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 
OB3 C01 C1  C  0 1 Y N N 2.609  -15.607 -8.572  -3.205 3.480  -1.362 C01 OB3 1  
OB3 C02 C2  C  0 1 Y N N 1.590  -15.592 -9.456  -3.328 3.838  -0.026 C02 OB3 2  
OB3 C03 C3  C  0 1 Y N N 0.976  -14.412 -9.664  -2.811 3.017  0.969  C03 OB3 3  
OB3 C04 C4  C  0 1 Y N N 1.367  -13.297 -9.017  -2.174 1.842  0.633  C04 OB3 4  
OB3 C05 C5  C  0 1 Y N N 2.398  -13.290 -8.139  -2.049 1.477  -0.710 C05 OB3 5  
OB3 C06 C6  C  0 1 Y N N 2.998  -14.485 -7.936  -2.570 2.306  -1.707 C06 OB3 6  
OB3 O01 O1  O  0 1 N N N 1.187  -16.720 -10.110 -3.955 4.996  0.310  O01 OB3 7  
OB3 C07 C7  C  0 1 N N N 2.764  -12.150 -7.502  -1.368 0.222  -1.075 C07 OB3 8  
OB3 C08 C8  C  0 1 N N N 3.933  -11.490 -7.281  -1.772 -1.040 -0.784 C08 OB3 9  
OB3 C09 C9  C  0 1 N N S 3.524  -10.270 -6.456  -0.715 -1.970 -1.388 C09 OB3 10 
OB3 C10 C10 C  0 1 Y N N 5.233  -11.669 -7.617  -2.980 -1.436 -0.038 C10 OB3 11 
OB3 C11 C11 C  0 1 N N S 1.722  -11.280 -6.798  -0.064 0.075  -1.864 C11 OB3 12 
OB3 C12 C12 C  0 1 Y N N 6.247  -11.310 -6.798  -4.247 -1.167 -0.563 C12 OB3 13 
OB3 C13 C13 C  0 1 Y N N 7.537  -11.465 -7.133  -5.373 -1.539 0.138  C13 OB3 14 
OB3 C14 C14 C  0 1 Y N N 7.889  -11.981 -8.323  -5.251 -2.180 1.364  C14 OB3 15 
OB3 C15 C15 C  0 1 Y N N 6.891  -12.338 -9.153  -3.994 -2.449 1.890  C15 OB3 16 
OB3 C16 C16 C  0 1 Y N N 5.595  -12.182 -8.814  -2.862 -2.086 1.194  C16 OB3 17 
OB3 O02 O2  O  0 1 N N N 9.190  -12.143 -8.675  -6.365 -2.544 2.052  O02 OB3 18 
OB3 C17 C17 C  0 1 N N R 1.918  -11.543 -5.297  1.001  -0.364 -0.813 C17 OB3 19 
OB3 C18 C18 C  0 1 N N N 3.200  -10.721 -5.026  0.538  -1.812 -0.471 C18 OB3 20 
OB3 S01 S1  S  0 1 N N N 0.405  -11.149 -4.290  2.664  -0.366 -1.537 S01 OB3 21 
OB3 O03 O3  O  0 1 N N N 2.233  -9.977  -6.936  -0.306 -1.190 -2.561 O03 OB3 22 
OB3 N01 N1  N  0 1 N N N -0.830 -12.147 -4.896  3.634  -0.980 -0.344 N01 OB3 23 
OB3 O04 O4  O  0 1 N N N 0.390  -9.741  -4.665  2.751  -1.320 -2.586 O04 OB3 24 
OB3 O05 O5  O  0 1 N N N 1.012  -11.568 -3.035  3.131  0.965  -1.717 O05 OB3 25 
OB3 C19 C19 C  0 1 Y N N -1.855 -11.752 -5.563  4.229  -0.122 0.585  C19 OB3 26 
OB3 C20 C20 C  0 1 N N N -0.662 -13.601 -4.626  3.868  -2.424 -0.262 C20 OB3 27 
OB3 C21 C21 C  0 1 Y N N -2.922 -10.987 -5.210  3.527  0.274  1.717  C21 OB3 28 
OB3 C22 C22 C  0 1 Y N N -3.908 -10.705 -6.081  4.119  1.123  2.633  C22 OB3 29 
OB3 C23 C23 C  0 1 Y N N -3.880 -11.171 -7.336  5.408  1.578  2.423  C23 OB3 30 
OB3 C24 C24 C  0 1 Y N N -2.843 -11.927 -7.708  6.109  1.186  1.298  C24 OB3 31 
OB3 C25 C25 C  0 1 Y N N -1.868 -12.202 -6.843  5.525  0.333  0.381  C25 OB3 32 
OB3 CL1 CL1 CL 0 0 N N N -3.195 -10.267 -3.658  1.909  -0.296 1.980  CL1 OB3 33 
OB3 H1  H1  H  0 1 N N N 3.122  -16.536 -8.371  -3.612 4.119  -2.131 H1  OB3 34 
OB3 H2  H2  H  0 1 N N N 0.154  -14.358 -10.363 -2.908 3.300  2.006  H2  OB3 35 
OB3 H3  H3  H  0 1 N N N 0.839  -12.374 -9.206  -1.772 1.205  1.407  H3  OB3 36 
OB3 H4  H4  H  0 1 N N N 3.820  -14.542 -7.238  -2.479 2.026  -2.746 H4  OB3 37 
OB3 H5  H5  H  0 1 N N N 1.729  -17.453 -9.842  -4.906 4.900  0.452  H5  OB3 38 
OB3 H6  H6  H  0 1 N N N 4.249  -9.444  -6.502  -1.038 -2.994 -1.572 H6  OB3 39 
OB3 H7  H7  H  0 1 N N N 0.692  -11.440 -7.149  0.210  0.928  -2.485 H7  OB3 40 
OB3 H8  H8  H  0 1 N N N 6.009  -10.881 -5.836  -4.343 -0.668 -1.516 H8  OB3 41 
OB3 H9  H9  H  0 1 N N N 8.306  -11.170 -6.434  -6.353 -1.331 -0.267 H9  OB3 42 
OB3 H10 H10 H  0 1 N N N 7.135  -12.761 -10.116 -3.904 -2.951 2.842  H10 OB3 43 
OB3 H11 H11 H  0 1 N N N 4.828  -12.474 -9.516  -1.884 -2.296 1.603  H11 OB3 44 
OB3 H12 H12 H  0 1 N N N 9.749  -11.838 -7.970  -6.684 -3.432 1.842  H12 OB3 45 
OB3 H13 H13 H  0 1 N N N 2.125  -12.611 -5.133  0.963  0.273  0.070  H13 OB3 46 
OB3 H14 H14 H  0 1 N N N 4.002  -11.342 -4.601  0.265  -1.901 0.580  H14 OB3 47 
OB3 H15 H15 H  0 1 N N N 3.006  -9.867  -4.361  1.307  -2.537 -0.735 H15 OB3 48 
OB3 H16 H16 H  0 1 N N N 0.260  -13.763 -4.048  4.745  -2.685 -0.856 H16 OB3 49 
OB3 H17 H17 H  0 1 N N N -1.524 -13.969 -4.051  4.037  -2.706 0.777  H17 OB3 50 
OB3 H18 H18 H  0 1 N N N -0.598 -14.146 -5.579  2.998  -2.956 -0.646 H18 OB3 51 
OB3 H19 H19 H  0 1 N N N -4.737 -10.091 -5.762  3.574  1.431  3.513  H19 OB3 52 
OB3 H20 H20 H  0 1 N N N -4.675 -10.942 -8.030  5.868  2.241  3.141  H20 OB3 53 
OB3 H21 H21 H  0 1 N N N -2.795 -12.317 -8.714  7.115  1.544  1.137  H21 OB3 54 
OB3 H22 H22 H  0 1 N N N -1.045 -12.815 -7.178  6.074  0.027  -0.498 H22 OB3 55 
# 
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 
OB3 O01 C02 SING N N 1  
OB3 C03 C02 DOUB Y N 2  
OB3 C03 C04 SING Y N 3  
OB3 C02 C01 SING Y N 4  
OB3 C15 C16 DOUB Y N 5  
OB3 C15 C14 SING Y N 6  
OB3 C04 C05 DOUB Y N 7  
OB3 C16 C10 SING Y N 8  
OB3 O02 C14 SING N N 9  
OB3 C01 C06 DOUB Y N 10 
OB3 C14 C13 DOUB Y N 11 
OB3 C05 C06 SING Y N 12 
OB3 C05 C07 SING N N 13 
OB3 C24 C23 DOUB Y N 14 
OB3 C24 C25 SING Y N 15 
OB3 C10 C08 SING N N 16 
OB3 C10 C12 DOUB Y N 17 
OB3 C07 C08 DOUB N N 18 
OB3 C07 C11 SING N N 19 
OB3 C23 C22 SING Y N 20 
OB3 C08 C09 SING N N 21 
OB3 C13 C12 SING Y N 22 
OB3 O03 C11 SING N N 23 
OB3 O03 C09 SING N N 24 
OB3 C25 C19 DOUB Y N 25 
OB3 C11 C17 SING N N 26 
OB3 C09 C18 SING N N 27 
OB3 C22 C21 DOUB Y N 28 
OB3 C19 C21 SING Y N 29 
OB3 C19 N01 SING N N 30 
OB3 C17 C18 SING N N 31 
OB3 C17 S01 SING N N 32 
OB3 C21 CL1 SING N N 33 
OB3 N01 C20 SING N N 34 
OB3 N01 S01 SING N N 35 
OB3 O04 S01 DOUB N N 36 
OB3 S01 O05 DOUB N N 37 
OB3 C01 H1  SING N N 38 
OB3 C03 H2  SING N N 39 
OB3 C04 H3  SING N N 40 
OB3 C06 H4  SING N N 41 
OB3 O01 H5  SING N N 42 
OB3 C09 H6  SING N N 43 
OB3 C11 H7  SING N N 44 
OB3 C12 H8  SING N N 45 
OB3 C13 H9  SING N N 46 
OB3 C15 H10 SING N N 47 
OB3 C16 H11 SING N N 48 
OB3 O02 H12 SING N N 49 
OB3 C17 H13 SING N N 50 
OB3 C18 H14 SING N N 51 
OB3 C18 H15 SING N N 52 
OB3 C20 H16 SING N N 53 
OB3 C20 H17 SING N N 54 
OB3 C20 H18 SING N N 55 
OB3 C22 H19 SING N N 56 
OB3 C23 H20 SING N N 57 
OB3 C24 H21 SING N N 58 
OB3 C25 H22 SING N N 59 
# 
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 
OB3 SMILES           ACDLabs              12.01 "c1cc(ccc1O)C2=C(C3CC(C2O3)S(=O)(N(C)c4c(Cl)cccc4)=O)c5ccc(cc5)O"                                                                                                                   
OB3 InChI            InChI                1.03  "InChI=1S/C25H22ClNO5S/c1-27(20-5-3-2-4-19(20)26)33(30,31)22-14-21-23(15-6-10-17(28)11-7-15)24(25(22)32-21)16-8-12-18(29)13-9-16/h2-13,21-22,25,28-29H,14H2,1H3/t21-,22+,25+/m0/s1" 
OB3 InChIKey         InChI                1.03  UOCUJSGNIGCJMB-SGIRGMQISA-N                                                                                                                                                         
OB3 SMILES_CANONICAL CACTVS               3.385 "CN(c1ccccc1Cl)[S](=O)(=O)[C@@H]2C[C@@H]3O[C@H]2C(=C3c4ccc(O)cc4)c5ccc(O)cc5"                                                                                                       
OB3 SMILES           CACTVS               3.385 "CN(c1ccccc1Cl)[S](=O)(=O)[CH]2C[CH]3O[CH]2C(=C3c4ccc(O)cc4)c5ccc(O)cc5"                                                                                                            
OB3 SMILES_CANONICAL "OpenEye OEToolkits" 1.9.2 "CN(c1ccccc1Cl)S(=O)(=O)[C@@H]2C[C@H]3C(=C([C@@H]2O3)c4ccc(cc4)O)c5ccc(cc5)O"                                                                                                       
OB3 SMILES           "OpenEye OEToolkits" 1.9.2 "CN(c1ccccc1Cl)S(=O)(=O)C2CC3C(=C(C2O3)c4ccc(cc4)O)c5ccc(cc5)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 
OB3 "SYSTEMATIC NAME" ACDLabs              12.01 "(1S,2R,4S)-N-(2-chlorophenyl)-5,6-bis(4-hydroxyphenyl)-N-methyl-7-oxabicyclo[2.2.1]hept-5-ene-2-sulfonamide" 
OB3 "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.9.2 "(1S,4S,5R)-N-(2-chlorophenyl)-2,3-bis(4-hydroxyphenyl)-N-methyl-7-oxabicyclo[2.2.1]hept-2-ene-5-sulfonamide" 
# 
loop_
_pdbx_chem_comp_audit.comp_id 
_pdbx_chem_comp_audit.action_type 
_pdbx_chem_comp_audit.date 
_pdbx_chem_comp_audit.processing_site 
OB3 "Create component" 2015-05-21 RCSB 
OB3 "Initial release"  2016-06-01 RCSB 
# 
