data_E3O
# 
_chem_comp.id                                    E3O 
_chem_comp.name                                  (16ALPHA,17ALPHA)-ESTRA-1,3,5(10)-TRIENE-3,16,17-TRIOL 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C18 H24 O3" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         ? 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2006-10-17 
_chem_comp.pdbx_modified_date                    2008-10-14 
_chem_comp.pdbx_ambiguous_flag                   ? 
_chem_comp.pdbx_release_status                   REL 
_chem_comp.pdbx_replaced_by                      ? 
_chem_comp.pdbx_replaces                         ? 
_chem_comp.formula_weight                        288.381 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     E3O 
_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        2J7Y 
_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 
E3O C2   C2   C 0 1 N N S 49.783 31.900 76.276 -3.345 0.866  -3.199 C2   E3O 1  
E3O C3   C3   C 0 1 N N N 50.429 31.897 74.896 -4.467 0.426  -2.222 C3   E3O 2  
E3O C4   C4   C 0 1 N N N 49.551 31.276 73.809 -5.834 0.229  -2.906 C4   E3O 3  
E3O C5   C5   C 0 1 N N S 49.145 29.868 74.264 -6.248 1.456  -3.733 C5   E3O 4  
E3O C6   C6   C 0 1 N N N 50.386 28.968 74.315 -6.559 2.638  -2.780 C6   E3O 5  
E3O C7   C7   C 0 1 N N R 48.093 29.170 73.403 -7.442 1.275  -4.698 C7   E3O 6  
E3O O1   O1   O 0 1 N N N 47.065 30.082 73.019 -7.389 0.019  -5.368 O1   E3O 7  
E3O C8   C8   C 0 1 N N R 47.533 28.079 74.338 -7.238 2.415  -5.723 C8   E3O 8  
E3O O2   O2   O 0 1 N N N 46.111 27.965 74.230 -7.686 2.063  -7.020 O2   E3O 9  
E3O C9   C9   C 0 1 N N N 47.897 28.493 75.765 -5.731 2.741  -5.726 C9   E3O 10 
E3O C10  C10  C 0 1 N N S 48.448 29.924 75.611 -5.119 1.735  -4.751 C10  E3O 11 
E3O C12  C12  C 0 1 N N R 49.346 30.482 76.723 -3.796 2.081  -4.065 C12  E3O 12 
E3O C14  C14  C 0 1 N N N 48.687 30.554 78.081 -2.686 2.418  -5.063 C14  E3O 13 
E3O C15  C15  C 0 1 N N N 49.669 30.949 79.189 -1.445 2.895  -4.315 C15  E3O 14 
E3O C16  C16  C 0 1 Y N N 50.521 32.157 78.797 -1.087 2.051  -3.117 C16  E3O 15 
E3O C17  C17  C 0 1 Y N N 51.231 32.850 79.745 0.175  2.251  -2.529 C17  E3O 16 
E3O C18  C18  C 0 1 Y N N 52.011 33.968 79.386 0.565  1.520  -1.410 C18  E3O 17 
E3O O3   O3   O 0 1 N N N 52.685 34.657 80.341 1.790  1.721  -0.856 O3   E3O 18 
E3O C19  C19  C 0 1 Y N N 52.059 34.377 78.056 -0.302 0.581  -0.866 C19  E3O 19 
E3O C20  C20  C 0 1 Y N N 51.366 33.726 77.047 -1.562 0.380  -1.435 C20  E3O 20 
E3O C21  C21  C 0 1 Y N N 50.601 32.604 77.339 -1.987 1.122  -2.551 C21  E3O 21 
E3O H2   H2   H 0 1 N N N 48.859 32.513 76.161 -3.180 0.017  -3.879 H2   E3O 22 
E3O H3C1 1H3C H 0 0 N N N 51.426 31.399 74.929 -4.566 1.170  -1.421 H3C1 E3O 23 
E3O H3C2 2H3C H 0 0 N N N 50.745 32.927 74.607 -4.206 -0.521 -1.737 H3C2 E3O 24 
E3O H12  H12  H 0 1 N N N 50.206 29.785 76.856 -3.949 2.954  -3.414 H12  E3O 25 
E3O H4C1 1H4C H 0 0 N N N 50.041 31.279 72.808 -5.767 -0.660 -3.546 H4C1 E3O 26 
E3O H4C2 2H4C H 0 0 N N N 48.673 31.913 73.550 -6.595 0.008  -2.148 H4C2 E3O 27 
E3O H6C1 1H6C H 0 0 N N N 51.193 29.400 74.951 -5.664 2.923  -2.217 H6C1 E3O 28 
E3O H6C2 2H6C H 0 0 N N N 50.937 28.955 73.346 -6.902 3.509  -3.346 H6C2 E3O 29 
E3O H6C3 3H6C H 0 0 N N N 50.091 27.945 74.646 -7.341 2.361  -2.066 H6C3 E3O 30 
E3O H7   H7   H 0 1 N N N 48.510 28.760 72.453 -8.413 1.345  -4.198 H7   E3O 31 
E3O H10  H10  H 0 1 N N N 47.611 30.657 75.688 -4.939 0.819  -5.338 H10  E3O 32 
E3O H1   H1   H 0 1 N N N 46.411 29.648 72.484 -6.453 -0.232 -5.411 H1   E3O 33 
E3O H8   H8   H 0 1 N N N 47.966 27.089 74.062 -7.791 3.307  -5.408 H8   E3O 34 
E3O HA   HA   H 0 1 N N N 45.766 27.293 74.806 -6.936 1.645  -7.477 HA   E3O 35 
E3O H9C1 1H9C H 0 0 N N N 47.060 28.401 76.496 -5.575 3.764  -5.365 H9C1 E3O 36 
E3O H9C2 2H9C H 0 0 N N N 48.589 27.789 76.284 -5.286 2.664  -6.723 H9C2 E3O 37 
E3O H141 1H14 H 0 0 N N N 48.168 29.598 78.326 -3.002 3.203  -5.759 H141 E3O 38 
E3O H142 2H14 H 0 0 N N N 47.806 31.237 78.064 -2.443 1.534  -5.667 H142 E3O 39 
E3O H151 1H15 H 0 0 N N N 50.306 30.085 79.491 -1.612 3.922  -3.965 H151 E3O 40 
E3O H152 2H15 H 0 0 N N N 49.140 31.124 80.155 -0.602 2.920  -5.017 H152 E3O 41 
E3O H17  H17  H 0 1 N N N 51.175 32.509 80.793 0.865  2.981  -2.945 H17  E3O 42 
E3O H3   H3   H 0 1 N N N 53.211 35.410 80.099 1.703  1.936  0.087  H3   E3O 43 
E3O H19  H19  H 0 1 N N N 52.672 35.254 77.790 0.003  0.000  -0.002 H19  E3O 44 
E3O H20  H20  H 0 1 N N N 51.423 34.101 76.011 -2.198 -0.378 -0.987 H20  E3O 45 
# 
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 
E3O C2  C3   SING N N 1  
E3O C2  C12  SING N N 2  
E3O C2  C21  SING N N 3  
E3O C2  H2   SING N N 4  
E3O C3  C4   SING N N 5  
E3O C3  H3C1 SING N N 6  
E3O C3  H3C2 SING N N 7  
E3O C4  C5   SING N N 8  
E3O C4  H4C1 SING N N 9  
E3O C4  H4C2 SING N N 10 
E3O C5  C6   SING N N 11 
E3O C5  C7   SING N N 12 
E3O C5  C10  SING N N 13 
E3O C6  H6C1 SING N N 14 
E3O C6  H6C2 SING N N 15 
E3O C6  H6C3 SING N N 16 
E3O C7  O1   SING N N 17 
E3O C7  C8   SING N N 18 
E3O C7  H7   SING N N 19 
E3O O1  H1   SING N N 20 
E3O C8  O2   SING N N 21 
E3O C8  C9   SING N N 22 
E3O C8  H8   SING N N 23 
E3O O2  HA   SING N N 24 
E3O C9  C10  SING N N 25 
E3O C9  H9C1 SING N N 26 
E3O C9  H9C2 SING N N 27 
E3O C10 C12  SING N N 28 
E3O C10 H10  SING N N 29 
E3O C12 C14  SING N N 30 
E3O C12 H12  SING N N 31 
E3O C14 C15  SING N N 32 
E3O C14 H141 SING N N 33 
E3O C14 H142 SING N N 34 
E3O C15 C16  SING N N 35 
E3O C15 H151 SING N N 36 
E3O C15 H152 SING N N 37 
E3O C16 C17  DOUB Y N 38 
E3O C16 C21  SING Y N 39 
E3O C17 C18  SING Y N 40 
E3O C17 H17  SING N N 41 
E3O C18 O3   SING N N 42 
E3O C18 C19  DOUB Y N 43 
E3O O3  H3   SING N N 44 
E3O C19 C20  SING Y N 45 
E3O C19 H19  SING N N 46 
E3O C20 C21  DOUB Y N 47 
E3O C20 H20  SING N N 48 
# 
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 
E3O SMILES           ACDLabs              10.04 Oc1cc4c(cc1)C3CCC2(C(CC(O)C2O)C3CC4)C                                                                                                                  
E3O InChI            InChI                1.02b InChI=1/C18H24O3/c1-18-7-6-13-12-5-3-11(19)8-10(12)2-4-14(13)15(18)9-16(20)17(18)21/h3,5,8,13-17,19-21H,2,4,6-7,9H2,1H3/t13-,14-,15+,16-,17-,18+/m1/s1 
E3O InChIKey         InChI                1.02b PROQIPRRNZUXQM-PNVOZDDCBG                                                                                                                              
E3O SMILES_CANONICAL CACTVS               3.341 C[C@]12CC[C@H]3[C@@H](CCc4cc(O)ccc34)[C@@H]1C[C@@H](O)[C@H]2O                                                                                          
E3O SMILES           CACTVS               3.341 C[C]12CC[CH]3[CH](CCc4cc(O)ccc34)[CH]1C[CH](O)[CH]2O                                                                                                   
E3O SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 C[C@]12CC[C@@H]3c4ccc(cc4CC[C@H]3[C@@H]1C[C@H]([C@H]2O)O)O                                                                                             
E3O SMILES           "OpenEye OEToolkits" 1.5.0 CC12CCC3c4ccc(cc4CCC3C1CC(C2O)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 
E3O "SYSTEMATIC NAME" ACDLabs              10.04 (9beta,13alpha,14beta,16alpha,17alpha)-estra-1(10),2,4-triene-3,16,17-triol                                  
E3O "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 (8R,9S,13S,14S,16R,17S)-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthrene-3,16,17-triol 
# 
