data_E4D
# 
_chem_comp.id                                    E4D 
_chem_comp.name                                  (2S,3R)-2-(4-(2-(PIPERIDIN-1-YL)ETHOXY)PHENYL)-2,3-DIHYDRO-3-(4-HYDROXYPHENYL)BENZO[B][1,4]OXATHIIN-6-OL 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C27 H29 N O4 S" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         "COMPOUND 4-D" 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2004-03-10 
_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                        463.588 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     E4D 
_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        1SJ0 
_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 
E4D C1   C1   C 0 1 N N R 31.172 -0.238 28.707 -0.005 1.419  -1.965 C1   E4D 1  
E4D C2   C2   C 0 1 N N S 31.276 -1.669 28.177 -1.112 0.389  -1.682 C2   E4D 2  
E4D O3   O3   O 0 1 N N N 30.050 -2.369 28.431 -0.886 -0.754 -2.480 O3   E4D 3  
E4D C4   C4   C 0 1 Y N N 28.861 -1.948 27.967 -1.046 -0.527 -3.802 C4   E4D 4  
E4D C5   C5   C 0 1 Y N N 27.932 -2.901 27.580 -1.431 -1.639 -4.559 C5   E4D 5  
E4D C6   C6   C 0 1 Y N N 26.724 -2.535 27.003 -1.574 -1.556 -5.925 C6   E4D 6  
E4D C7   C7   C 0 1 Y N N 26.346 -1.183 27.031 -1.339 -0.354 -6.577 C7   E4D 7  
E4D O8   O8   O 0 1 N N N 25.128 -0.857 26.584 -1.469 -0.269 -7.928 O8   E4D 8  
E4D C9   C9   C 0 1 Y N N 27.284 -0.215 27.426 -0.970 0.756  -5.840 C9   E4D 9  
E4D C10  C10  C 0 1 Y N N 28.555 -0.563 27.854 -0.830 0.675  -4.456 C10  E4D 10 
E4D S11  S11  S 0 1 N N N 29.608 0.457  28.191 -0.376 2.146  -3.590 S11  E4D 11 
E4D C12  C12  C 0 1 Y N N 32.470 0.480  28.420 1.337  0.736  -1.999 C12  E4D 12 
E4D C13  C13  C 0 1 Y N N 32.680 1.380  27.373 1.728  0.038  -3.127 C13  E4D 13 
E4D C14  C14  C 0 1 Y N N 33.932 1.987  27.205 2.961  -0.582 -3.164 C14  E4D 14 
E4D C15  C15  C 0 1 Y N N 34.976 1.698  28.099 3.803  -0.516 -2.063 C15  E4D 15 
E4D O16  O16  O 0 1 N N N 36.191 2.251  27.923 5.014  -1.131 -2.094 O16  E4D 16 
E4D C17  C17  C 0 1 Y N N 34.783 0.784  29.143 3.408  0.184  -0.932 C17  E4D 17 
E4D C18  C18  C 0 1 Y N N 33.519 0.203  29.311 2.176  0.808  -0.903 C18  E4D 18 
E4D C19  C19  C 0 1 Y N N 31.630 -1.840 26.702 -1.083 0.003  -0.226 C19  E4D 19 
E4D C20  C20  C 0 1 Y N N 32.648 -2.767 26.448 -1.838 0.710  0.690  C20  E4D 20 
E4D C21  C21  C 0 1 Y N N 33.073 -3.050 25.148 -1.817 0.354  2.025  C21  E4D 21 
E4D C22  C22  C 0 1 Y N N 32.496 -2.352 24.060 -1.029 -0.706 2.446  C22  E4D 22 
E4D C23  C23  C 0 1 Y N N 31.455 -1.471 24.295 -0.268 -1.410 1.525  C23  E4D 23 
E4D C24  C24  C 0 1 Y N N 31.047 -1.171 25.623 -0.296 -1.054 0.191  C24  E4D 24 
E4D O25  O25  O 0 1 N N N 32.911 -2.572 22.785 -1.003 -1.054 3.760  O25  E4D 25 
E4D C26  C26  C 0 1 N N N 34.002 -3.400 22.346 -1.878 -0.155 4.443  C26  E4D 26 
E4D C27  C27  C 0 1 N N N 33.655 -4.384 21.206 -1.894 -0.494 5.935  C27  E4D 27 
E4D N28  N28  N 0 1 N N N 32.800 -4.012 20.054 -0.536 -0.366 6.481  N28  E4D 28 
E4D C29  C29  C 0 1 N N N 31.597 -3.241 20.319 -0.176 1.052  6.389  C29  E4D 29 
E4D C30  C30  C 0 1 N N N 30.557 -3.264 19.177 1.230  1.266  6.949  C30  E4D 30 
E4D C31  C31  C 0 1 N N N 31.187 -2.912 17.813 1.253  0.859  8.426  C31  E4D 31 
E4D C32  C32  C 0 1 N N N 32.413 -3.842 17.617 0.760  -0.586 8.550  C32  E4D 32 
E4D C33  C33  C 0 1 N N N 33.434 -3.674 18.776 -0.622 -0.704 7.906  C33  E4D 33 
E4D H1   H1   H 0 1 N N N 31.102 -0.142 29.816 -0.010 2.194  -1.199 H1   E4D 34 
E4D H2   H2   H 0 1 N N N 32.145 -2.091 28.734 -2.083 0.820  -1.928 H2   E4D 35 
E4D H5   H5   H 0 1 N N N 28.158 -3.970 27.734 -1.619 -2.580 -4.062 H5   E4D 36 
E4D H6   H6   H 0 1 N N N 26.081 -3.299 26.534 -1.871 -2.427 -6.491 H6   E4D 37 
E4D HO8  HO8  H 0 1 N N N 24.872 0.058  26.603 -0.605 -0.481 -8.306 HO8  E4D 38 
E4D H9   H9   H 0 1 N N N 27.014 0.854  27.399 -0.790 1.695  -6.342 H9   E4D 39 
E4D H13  H13  H 0 1 N N N 31.856 1.612  26.678 1.070  -0.016 -3.982 H13  E4D 40 
E4D H14  H14  H 0 1 N N N 34.095 2.690  26.371 3.266  -1.127 -4.045 H14  E4D 41 
E4D H16  H16  H 0 1 N N N 36.897 2.056  28.528 4.881  -2.028 -1.757 H16  E4D 42 
E4D H17  H17  H 0 1 N N N 35.613 0.526  29.822 4.063  0.240  -0.075 H17  E4D 43 
E4D H18  H18  H 0 1 N N N 33.347 -0.483 30.158 1.868  1.353  -0.023 H18  E4D 44 
E4D H20  H20  H 0 1 N N N 33.128 -3.288 27.294 -2.451 1.536  0.361  H20  E4D 45 
E4D H21  H21  H 0 1 N N N 33.852 -3.813 24.983 -2.411 0.904  2.740  H21  E4D 46 
E4D H23  H23  H 0 1 N N N 30.953 -1.010 23.428 0.345  -2.237 1.851  H23  E4D 47 
E4D H24  H24  H 0 1 N N N 30.271 -0.412 25.818 0.295  -1.602 -0.526 H24  E4D 48 
E4D H261 1H26 H 0 0 N N N 34.440 -3.951 23.211 -2.885 -0.249 4.038  H261 E4D 49 
E4D H262 2H26 H 0 0 N N N 34.874 -2.768 22.057 -1.526 0.867  4.307  H262 E4D 50 
E4D H271 1H27 H 0 0 N N N 33.209 -5.293 21.673 -2.246 -1.517 6.071  H271 E4D 51 
E4D H272 2H27 H 0 0 N N N 34.616 -4.774 20.797 -2.561 0.191  6.457  H272 E4D 52 
E4D H291 1H29 H 0 0 N N N 31.860 -2.190 20.584 -0.203 1.365  5.346  H291 E4D 53 
E4D H292 2H29 H 0 0 N N N 31.129 -3.568 21.277 -0.889 1.644  6.963  H292 E4D 54 
E4D H301 1H30 H 0 0 N N N 29.691 -2.600 19.406 1.502  2.317  6.857  H301 E4D 55 
E4D H302 2H30 H 0 0 N N N 30.023 -4.242 19.136 1.941  0.655  6.392  H302 E4D 56 
E4D H311 1H31 H 0 0 N N N 31.440 -1.830 17.716 0.598  1.517  8.996  H311 E4D 57 
E4D H312 2H31 H 0 0 N N N 30.460 -2.966 16.970 2.270  0.932  8.809  H312 E4D 58 
E4D H321 1H32 H 0 0 N N N 32.892 -3.686 16.622 0.697  -0.860 9.603  H321 E4D 59 
E4D H322 2H32 H 0 0 N N N 32.105 -4.906 17.492 1.457  -1.253 8.041  H322 E4D 60 
E4D H331 1H33 H 0 0 N N N 34.365 -4.263 18.602 -1.311 -0.018 8.400  H331 E4D 61 
E4D H332 2H33 H 0 0 N N N 33.887 -2.655 18.790 -0.987 -1.725 8.016  H332 E4D 62 
# 
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 
E4D C1  C2   SING N N 1  
E4D C1  S11  SING N N 2  
E4D C1  C12  SING N N 3  
E4D C1  H1   SING N N 4  
E4D C2  O3   SING N N 5  
E4D C2  C19  SING N N 6  
E4D C2  H2   SING N N 7  
E4D O3  C4   SING N N 8  
E4D C4  C5   DOUB Y N 9  
E4D C4  C10  SING Y N 10 
E4D C5  C6   SING Y N 11 
E4D C5  H5   SING N N 12 
E4D C6  C7   DOUB Y N 13 
E4D C6  H6   SING N N 14 
E4D C7  O8   SING N N 15 
E4D C7  C9   SING Y N 16 
E4D O8  HO8  SING N N 17 
E4D C9  C10  DOUB Y N 18 
E4D C9  H9   SING N N 19 
E4D C10 S11  SING N N 20 
E4D C12 C13  DOUB Y N 21 
E4D C12 C18  SING Y N 22 
E4D C13 C14  SING Y N 23 
E4D C13 H13  SING N N 24 
E4D C14 C15  DOUB Y N 25 
E4D C14 H14  SING N N 26 
E4D C15 O16  SING N N 27 
E4D C15 C17  SING Y N 28 
E4D O16 H16  SING N N 29 
E4D C17 C18  DOUB Y N 30 
E4D C17 H17  SING N N 31 
E4D C18 H18  SING N N 32 
E4D C19 C20  DOUB Y N 33 
E4D C19 C24  SING Y N 34 
E4D C20 C21  SING Y N 35 
E4D C20 H20  SING N N 36 
E4D C21 C22  DOUB Y N 37 
E4D C21 H21  SING N N 38 
E4D C22 C23  SING Y N 39 
E4D C22 O25  SING N N 40 
E4D C23 C24  DOUB Y N 41 
E4D C23 H23  SING N N 42 
E4D C24 H24  SING N N 43 
E4D O25 C26  SING N N 44 
E4D C26 C27  SING N N 45 
E4D C26 H261 SING N N 46 
E4D C26 H262 SING N N 47 
E4D C27 N28  SING N N 48 
E4D C27 H271 SING N N 49 
E4D C27 H272 SING N N 50 
E4D N28 C29  SING N N 51 
E4D N28 C33  SING N N 52 
E4D C29 C30  SING N N 53 
E4D C29 H291 SING N N 54 
E4D C29 H292 SING N N 55 
E4D C30 C31  SING N N 56 
E4D C30 H301 SING N N 57 
E4D C30 H302 SING N N 58 
E4D C31 C32  SING N N 59 
E4D C31 H311 SING N N 60 
E4D C31 H312 SING N N 61 
E4D C32 C33  SING N N 62 
E4D C32 H321 SING N N 63 
E4D C32 H322 SING N N 64 
E4D C33 H331 SING N N 65 
E4D C33 H332 SING N N 66 
# 
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 
E4D SMILES           ACDLabs              10.04 O2c5c(SC(c1ccc(O)cc1)C2c4ccc(OCCN3CCCCC3)cc4)cc(O)cc5                                                                                                                         
E4D InChI            InChI                1.02b InChI=1/C27H29NO4S/c29-21-8-4-20(5-9-21)27-26(32-24-13-10-22(30)18-25(24)33-27)19-6-11-23(12-7-19)31-17-16-28-14-2-1-3-15-28/h4-13,18,26-27,29-30H,1-3,14-17H2/t26-,27+/m0/s1 
E4D InChIKey         InChI                1.02b TWZNCTCQAGRUGQ-RRPNLBNLBL                                                                                                                                                     
E4D SMILES_CANONICAL CACTVS               3.341 Oc1ccc(cc1)[C@H]2Sc3cc(O)ccc3O[C@H]2c4ccc(OCCN5CCCCC5)cc4                                                                                                                     
E4D SMILES           CACTVS               3.341 Oc1ccc(cc1)[CH]2Sc3cc(O)ccc3O[CH]2c4ccc(OCCN5CCCCC5)cc4                                                                                                                       
E4D SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 c1cc(ccc1[C@@H]2[C@@H](Oc3ccc(cc3S2)O)c4ccc(cc4)OCCN5CCCCC5)O                                                                                                                 
E4D SMILES           "OpenEye OEToolkits" 1.5.0 c1cc(ccc1C2C(Oc3ccc(cc3S2)O)c4ccc(cc4)OCCN5CCCCC5)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 
E4D "SYSTEMATIC NAME" ACDLabs              10.04 (2S,3R)-3-(4-hydroxyphenyl)-2-[4-(2-piperidin-1-ylethoxy)phenyl]-2,3-dihydro-1,4-benzoxathiin-6-ol 
E4D "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 (2S,3R)-3-(4-hydroxyphenyl)-2-[4-(2-piperidin-1-ylethoxy)phenyl]-2,3-dihydro-1,4-benzoxathiin-6-ol 
# 
