data_RAL
# 
_chem_comp.id                                    RAL 
_chem_comp.name                                  RALOXIFENE 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C28 H27 N O4 S" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         ? 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     1999-07-08 
_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                        473.583 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     RAL 
_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        1QKN 
_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 
RAL C1   C1   C 0 1 Y N N 16.931 29.525 8.729  2.444  0.825  -3.610 C1   RAL 1  
RAL C2   C2   C 0 1 Y N N 15.839 30.128 8.103  3.478  0.398  -4.401 C2   RAL 2  
RAL C3   C3   C 0 1 Y N N 15.155 31.132 8.777  3.348  -0.722 -5.215 C3   RAL 3  
RAL O3   O3   O 0 1 N N N 14.066 31.718 8.166  4.385  -1.129 -5.994 O3   RAL 4  
RAL C4   C4   C 0 1 Y N N 15.578 31.529 10.065 2.150  -1.419 -5.225 C4   RAL 5  
RAL C5   C5   C 0 1 Y N N 16.646 30.947 10.657 1.106  -0.994 -4.430 C5   RAL 6  
RAL S6   S6   S 0 1 Y N N 17.361 31.237 12.147 -0.542 -1.590 -4.161 S6   RAL 7  
RAL C7   C7   C 0 1 Y N N 18.599 30.111 12.067 -1.096 -0.382 -2.975 C7   RAL 8  
RAL C8   C8   C 0 1 Y N N 19.604 29.881 13.140 -2.411 -0.284 -2.314 C8   RAL 9  
RAL C9   C9   C 0 1 Y N N 19.230 29.554 14.413 -2.969 -1.406 -1.694 C9   RAL 10 
RAL C10  C10  C 0 1 Y N N 20.162 29.321 15.430 -4.197 -1.310 -1.078 C10  RAL 11 
RAL C11  C11  C 0 1 Y N N 21.512 29.427 15.143 -4.881 -0.100 -1.073 C11  RAL 12 
RAL O11  O11  O 0 1 N N N 22.447 29.204 16.139 -6.092 -0.010 -0.464 O11  RAL 13 
RAL C12  C12  C 0 1 Y N N 21.914 29.760 13.857 -4.333 1.015  -1.693 C12  RAL 14 
RAL C13  C13  C 0 1 Y N N 20.961 29.985 12.866 -3.103 0.930  -2.307 C13  RAL 15 
RAL C14  C14  C 0 1 Y N N 17.351 29.908 9.989  1.211  0.135  -3.598 C14  RAL 16 
RAL C15  C15  C 0 1 Y N N 18.477 29.445 10.813 0.005  0.449  -2.826 C15  RAL 17 
RAL C16  C16  C 0 1 N N N 19.347 28.422 10.448 -0.033 1.600  -1.923 C16  RAL 18 
RAL O16  O16  O 0 1 N N N 19.245 27.333 11.042 -0.392 2.687  -2.338 O16  RAL 19 
RAL C17  C17  C 0 1 Y N N 20.363 28.588 9.414  0.362  1.442  -0.509 C17  RAL 20 
RAL C18  C18  C 0 1 Y N N 21.123 27.508 8.970  0.431  2.559  0.326  C18  RAL 21 
RAL C19  C19  C 0 1 Y N N 22.123 27.612 7.971  0.800  2.408  1.645  C19  RAL 22 
RAL C20  C20  C 0 1 Y N N 22.325 28.877 7.445  1.103  1.147  2.143  C20  RAL 23 
RAL C21  C21  C 0 1 Y N N 21.572 29.949 7.896  1.034  0.033  1.315  C21  RAL 24 
RAL C22  C22  C 0 1 Y N N 20.606 29.830 8.850  0.661  0.175  -0.002 C22  RAL 25 
RAL O23  O23  O 0 1 N N N 23.230 29.279 6.466  1.466  1.002  3.443  O23  RAL 26 
RAL C24  C24  C 0 1 N N N 23.464 28.353 5.432  1.828  -0.368 3.621  C24  RAL 27 
RAL C25  C25  C 0 1 N N N 24.776 28.790 4.794  2.308  -0.587 5.057  C25  RAL 28 
RAL N26  N26  N 0 1 N N N 24.743 29.712 3.643  1.230  -0.240 5.992  N26  RAL 29 
RAL C27  C27  C 0 1 N N N 26.071 29.594 2.985  1.752  -0.471 7.343  C27  RAL 30 
RAL C28  C28  C 0 1 N N N 26.179 30.450 1.724  0.677  -0.137 8.378  C28  RAL 31 
RAL C29  C29  C 0 1 N N N 25.959 31.932 2.094  -0.530 -1.055 8.165  C29  RAL 32 
RAL C30  C30  C 0 1 N N N 24.604 32.042 2.797  -1.012 -0.915 6.718  C30  RAL 33 
RAL C31  C31  C 0 1 N N N 24.539 31.117 4.020  0.151  -1.209 5.769  C31  RAL 34 
RAL H1   H1   H 0 1 N N N 17.479 28.720 8.211  2.573  1.698  -2.987 H1   RAL 35 
RAL H2   H2   H 0 1 N N N 15.522 29.816 7.093  4.411  0.942  -4.393 H2   RAL 36 
RAL HO3  HO3  H 0 1 N N N 13.598 32.404 8.626  4.292  -0.677 -6.843 HO3  RAL 37 
RAL H4   H4   H 0 1 N N N 15.056 32.321 10.628 2.035  -2.291 -5.851 H4   RAL 38 
RAL H9   H9   H 0 1 N N N 18.150 29.476 14.624 -2.437 -2.346 -1.697 H9   RAL 39 
RAL H10  H10  H 0 1 N N N 19.835 29.055 16.449 -4.628 -2.176 -0.598 H10  RAL 40 
RAL HO1  HO1  H 0 1 N N N 23.373 29.276 15.942 -5.922 0.163  0.471  HO1  RAL 41 
RAL H12  H12  H 0 1 N N N 22.988 29.845 13.623 -4.869 1.953  -1.687 H12  RAL 42 
RAL H13  H13  H 0 1 N N N 21.286 30.250 11.846 -2.676 1.799  -2.784 H13  RAL 43 
RAL H18  H18  H 0 1 N N N 20.923 26.525 9.430  0.197  3.540  -0.060 H18  RAL 44 
RAL H19  H19  H 0 1 N N N 22.715 26.750 7.619  0.854  3.271  2.292  H19  RAL 45 
RAL H21  H21  H 0 1 N N N 21.751 30.951 7.472  1.270  -0.945 1.706  H21  RAL 46 
RAL H22  H22  H 0 1 N N N 20.032 30.720 9.159  0.608  -0.690 -0.646 H22  RAL 47 
RAL H241 1H24 H 0 0 N N N 23.459 27.290 5.769  0.962  -1.000 3.427  H241 RAL 48 
RAL H242 2H24 H 0 0 N N N 22.619 28.262 4.709  2.629  -0.625 2.927  H242 RAL 49 
RAL H251 1H25 H 0 0 N N N 25.430 29.226 5.584  2.584  -1.633 5.192  H251 RAL 50 
RAL H252 2H25 H 0 0 N N N 25.355 27.881 4.508  3.175  0.045  5.251  H252 RAL 51 
RAL H271 1H27 H 0 0 N N N 26.894 29.827 3.699  2.042  -1.517 7.445  H271 RAL 52 
RAL H272 2H27 H 0 0 N N N 26.317 28.528 2.768  2.624  0.162  7.507  H272 RAL 53 
RAL H281 1H28 H 0 0 N N N 27.140 30.287 1.183  1.077  -0.287 9.381  H281 RAL 54 
RAL H282 2H28 H 0 0 N N N 25.486 30.107 0.920  0.369  0.902  8.260  H282 RAL 55 
RAL H291 1H29 H 0 0 N N N 26.795 32.356 2.697  -0.239 -2.089 8.355  H291 RAL 56 
RAL H292 2H29 H 0 0 N N N 26.048 32.614 1.217  -1.331 -0.769 8.846  H292 RAL 57 
RAL H301 1H30 H 0 0 N N N 24.366 33.097 3.067  -1.820 -1.623 6.533  H301 RAL 58 
RAL H302 2H30 H 0 0 N N N 23.760 31.852 2.093  -1.371 0.099  6.550  H302 RAL 59 
RAL H311 1H31 H 0 0 N N N 23.587 31.253 4.585  -0.194 -1.136 4.738  H311 RAL 60 
RAL H312 2H31 H 0 0 N N N 25.257 31.435 4.811  0.525  -2.216 5.955  H312 RAL 61 
# 
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 
RAL C1  C2   DOUB Y N 1  
RAL C1  C14  SING Y N 2  
RAL C1  H1   SING N N 3  
RAL C2  C3   SING Y N 4  
RAL C2  H2   SING N N 5  
RAL C3  O3   SING N N 6  
RAL C3  C4   DOUB Y N 7  
RAL O3  HO3  SING N N 8  
RAL C4  C5   SING Y N 9  
RAL C4  H4   SING N N 10 
RAL C5  S6   SING Y N 11 
RAL C5  C14  DOUB Y N 12 
RAL S6  C7   SING Y N 13 
RAL C7  C8   SING N N 14 
RAL C7  C15  DOUB Y N 15 
RAL C8  C9   SING Y N 16 
RAL C8  C13  DOUB Y N 17 
RAL C9  C10  DOUB Y N 18 
RAL C9  H9   SING N N 19 
RAL C10 C11  SING Y N 20 
RAL C10 H10  SING N N 21 
RAL C11 O11  SING N N 22 
RAL C11 C12  DOUB Y N 23 
RAL O11 HO1  SING N N 24 
RAL C12 C13  SING Y N 25 
RAL C12 H12  SING N N 26 
RAL C13 H13  SING N N 27 
RAL C14 C15  SING Y N 28 
RAL C15 C16  SING N N 29 
RAL C16 O16  DOUB N N 30 
RAL C16 C17  SING N N 31 
RAL C17 C18  DOUB Y N 32 
RAL C17 C22  SING Y N 33 
RAL C18 C19  SING Y N 34 
RAL C18 H18  SING N N 35 
RAL C19 C20  DOUB Y N 36 
RAL C19 H19  SING N N 37 
RAL C20 C21  SING Y N 38 
RAL C20 O23  SING N N 39 
RAL C21 C22  DOUB Y N 40 
RAL C21 H21  SING N N 41 
RAL C22 H22  SING N N 42 
RAL O23 C24  SING N N 43 
RAL C24 C25  SING N N 44 
RAL C24 H241 SING N N 45 
RAL C24 H242 SING N N 46 
RAL C25 N26  SING N N 47 
RAL C25 H251 SING N N 48 
RAL C25 H252 SING N N 49 
RAL N26 C27  SING N N 50 
RAL N26 C31  SING N N 51 
RAL C27 C28  SING N N 52 
RAL C27 H271 SING N N 53 
RAL C27 H272 SING N N 54 
RAL C28 C29  SING N N 55 
RAL C28 H281 SING N N 56 
RAL C28 H282 SING N N 57 
RAL C29 C30  SING N N 58 
RAL C29 H291 SING N N 59 
RAL C29 H292 SING N N 60 
RAL C30 C31  SING N N 61 
RAL C30 H301 SING N N 62 
RAL C30 H302 SING N N 63 
RAL C31 H311 SING N N 64 
RAL C31 H312 SING N N 65 
# 
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 
RAL SMILES           ACDLabs              10.04 O=C(c1c3ccc(O)cc3sc1c2ccc(O)cc2)c5ccc(OCCN4CCCCC4)cc5                                                                                                       
RAL InChI            InChI                1.02b InChI=1/C28H27NO4S/c30-21-8-4-20(5-9-21)28-26(24-13-10-22(31)18-25(24)34-28)27(32)19-6-11-23(12-7-19)33-17-16-29-14-2-1-3-15-29/h4-13,18,30-31H,1-3,14-17H2 
RAL InChIKey         InChI                1.02b GZUITABIAKMVPG-UHFFFAOYAG                                                                                                                                   
RAL SMILES_CANONICAL CACTVS               3.341 Oc1ccc(cc1)c2sc3cc(O)ccc3c2C(=O)c4ccc(OCCN5CCCCC5)cc4                                                                                                       
RAL SMILES           CACTVS               3.341 Oc1ccc(cc1)c2sc3cc(O)ccc3c2C(=O)c4ccc(OCCN5CCCCC5)cc4                                                                                                       
RAL SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 c1cc(ccc1c2c(c3ccc(cc3s2)O)C(=O)c4ccc(cc4)OCCN5CCCCC5)O                                                                                                     
RAL SMILES           "OpenEye OEToolkits" 1.5.0 c1cc(ccc1c2c(c3ccc(cc3s2)O)C(=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 
RAL "SYSTEMATIC NAME" ACDLabs              10.04 [6-hydroxy-2-(4-hydroxyphenyl)-1-benzothiophen-3-yl][4-(2-piperidin-1-ylethoxy)phenyl]methanone  
RAL "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 [6-hydroxy-2-(4-hydroxyphenyl)-1-benzothiophen-3-yl]-[4-(2-piperidin-1-ylethoxy)phenyl]methanone 
# 
