data_FRR
# 
_chem_comp.id                                    FRR 
_chem_comp.name                                  (3R,5Z,8S,9S,11E)-8,9,16-TRIHYDROXY-14-METHOXY-3-METHYL-3,4,9,10-TETRAHYDRO-1H-2-BENZOXACYCLOTETRADECINE-1,7(8H)-DIONE 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C19 H22 O7" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         ? 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2006-10-26 
_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                        362.374 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     FRR 
_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        ? 
_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 
FRR C11  C11  C 0 1 Y N N 18.855 37.420 45.268 -1.615 0.017  -1.422  C11  FRR 1  
FRR C2   C2   C 0 1 Y N N 17.578 38.005 45.232 -2.119 0.587  -2.600  C2   FRR 2  
FRR C3   C3   C 0 1 Y N N 17.367 39.116 44.365 -1.413 1.598  -3.281  C3   FRR 3  
FRR C14  C14  C 0 1 Y N N 18.434 39.599 43.597 -0.190 2.021  -2.731  C14  FRR 4  
FRR C15  C15  C 0 1 Y N N 19.695 39.009 43.667 0.318  1.445  -1.563  C15  FRR 5  
FRR C16  C16  C 0 1 Y N N 19.896 37.916 44.500 -0.394 0.443  -0.910  C16  FRR 6  
FRR C23  C23  C 0 1 N N N 16.074 39.807 44.240 -1.964 2.246  -4.485  C23  FRR 7  
FRR C17  C17  C 0 1 N N N 15.338 39.854 43.108 -1.234 2.776  -5.480  C17  FRR 8  
FRR O15  O15  O 0 1 N N N 15.273 37.842 45.985 -3.274 -0.570 -4.223  O15  FRR 9  
FRR C26  C26  C 0 1 N N N 16.549 37.375 46.140 -3.430 0.084  -3.043  C26  FRR 10 
FRR C31  C31  C 0 1 N N S 13.973 37.670 46.710 -4.431 -1.280 -4.723  C31  FRR 11 
FRR C18  C18  C 0 1 N N N 12.928 38.182 45.723 -4.299 -1.440 -6.245  C18  FRR 12 
FRR C24  C24  C 0 1 N N S 12.924 39.498 42.405 -1.471 2.503  -7.948  C24  FRR 13 
FRR C34  C34  C 0 1 N N N 13.897 40.368 43.148 -1.852 3.355  -6.725  C34  FRR 14 
FRR C39  C39  C 0 1 N N S 11.456 39.764 42.515 -2.587 2.414  -8.999  C39  FRR 15 
FRR C40  C40  C 0 1 N N N 11.410 38.500 43.341 -3.825 1.679  -8.483  C40  FRR 16 
FRR C41  C41  C 0 1 N N N 10.666 38.516 44.640 -3.605 0.346  -7.856  C41  FRR 17 
FRR C42  C42  C 0 1 N N N 11.471 37.774 45.710 -4.484 -0.132 -6.966  C42  FRR 18 
FRR O38  O38  O 0 1 N N N 16.831 36.516 46.981 -4.446 0.213  -2.380  O38  FRR 19 
FRR O40  O40  O 0 1 N N N 11.954 37.475 42.985 -4.954 2.156  -8.583  O40  FRR 20 
FRR O42  O42  O 0 1 N N N 13.305 38.991 41.207 -0.312 3.085  -8.549  O42  FRR 21 
FRR O44  O44  O 0 1 N N N 10.898 40.931 43.071 -2.963 3.707  -9.452  O44  FRR 22 
FRR O46  O46  O 0 1 N N N 19.129 36.461 45.973 -2.289 -0.968 -0.760  O46  FRR 23 
FRR O48  O48  O 0 1 N N N 20.728 39.514 42.900 1.507  1.872  -1.057  O48  FRR 24 
FRR C59  C59  C 0 1 N N N 21.981 39.570 43.577 1.969  1.242  0.137   C59  FRR 25 
FRR C62  C62  C 0 1 N N N 13.709 36.254 47.217 -4.478 -2.651 -4.052  C62  FRR 26 
FRR H46  H46  H 0 1 N N N 19.200 35.682 45.435 -2.749 -0.598 0.009   H46  FRR 27 
FRR H16  H16  H 0 1 N N N 20.869 37.450 44.549 0.002  -0.001 -0.000  H16  FRR 28 
FRR H591 1H59 H 0 0 N N N 22.797 39.584 42.839 3.018  1.499  0.303   H591 FRR 29 
FRR H592 2H59 H 0 0 N N N 22.026 40.482 44.191 1.858  0.159  0.045   H592 FRR 30 
FRR H593 3H59 H 0 0 N N N 22.088 38.687 44.224 1.371  1.597  0.980   H593 FRR 31 
FRR H14  H14  H 0 1 N N N 18.277 40.442 42.940 0.383  2.820  -3.198  H14  FRR 32 
FRR H23  H23  H 0 1 N N N 15.687 40.311 45.113 -3.048 2.254  -4.568  H23  FRR 33 
FRR H17  H17  H 0 1 N N N 15.768 39.528 42.172 -0.148 2.766  -5.444  H17  FRR 34 
FRR H341 1H34 H 0 0 N N N 13.580 40.413 44.200 -2.939 3.397  -6.597  H341 FRR 35 
FRR H342 2H34 H 0 0 N N N 13.891 41.352 42.657 -1.499 4.387  -6.840  H342 FRR 36 
FRR H24  H24  H 0 1 N N N 13.039 38.654 43.101 -1.178 1.494  -7.635  H24  FRR 37 
FRR H42  H42  H 0 1 N N N 13.394 39.697 40.578 0.117  2.377  -9.053  H42  FRR 38 
FRR H39  H39  H 0 1 N N N 10.873 39.959 41.603 -2.228 1.875  -9.883  H39  FRR 39 
FRR H44  H44  H 0 1 N N N 10.772 40.809 44.005 -2.543 3.834  -10.318 H44  FRR 40 
FRR H41  H41  H 0 1 N N N 9.705  38.982 44.799 -2.694 -0.188 -8.099  H41  FRR 41 
FRR H1   H1   H 0 1 N N N 11.047 37.041 46.380 -5.385 0.428  -6.729  H1   FRR 42 
FRR H181 1H18 H 0 0 N N N 12.909 39.271 45.880 -5.067 -2.131 -6.611  H181 FRR 43 
FRR H182 2H18 H 0 0 N N N 13.281 37.722 44.788 -3.320 -1.872 -6.489  H182 FRR 44 
FRR H31  H31  H 0 1 N N N 13.961 38.234 47.654 -5.348 -0.723 -4.489  H31  FRR 45 
FRR H621 1H62 H 0 0 N N N 13.646 35.564 46.363 -4.136 -2.583 -3.015  H621 FRR 46 
FRR H622 2H62 H 0 0 N N N 14.530 35.943 47.879 -5.498 -3.046 -4.054  H622 FRR 47 
FRR H623 3H62 H 0 0 N N N 12.761 36.235 47.774 -3.834 -3.360 -4.581  H623 FRR 48 
# 
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 
FRR C11 O46  SING N N 1  
FRR C11 C16  SING Y N 2  
FRR C11 C2   DOUB Y N 3  
FRR C2  C26  SING N N 4  
FRR C2  C3   SING Y N 5  
FRR C3  C14  DOUB Y N 6  
FRR C3  C23  SING N N 7  
FRR C14 C15  SING Y N 8  
FRR C14 H14  SING N N 9  
FRR C15 C16  DOUB Y N 10 
FRR C15 O48  SING N N 11 
FRR C16 H16  SING N N 12 
FRR C23 H23  SING N N 13 
FRR C23 C17  DOUB N N 14 
FRR C17 H17  SING N N 15 
FRR C17 C34  SING N N 16 
FRR O15 C31  SING N N 17 
FRR O15 C26  SING N N 18 
FRR C26 O38  DOUB N N 19 
FRR C31 C18  SING N N 20 
FRR C31 H31  SING N N 21 
FRR C31 C62  SING N N 22 
FRR C18 C42  SING N N 23 
FRR C18 H181 SING N N 24 
FRR C18 H182 SING N N 25 
FRR C24 C34  SING N N 26 
FRR C24 H24  SING N N 27 
FRR C24 O42  SING N N 28 
FRR C24 C39  SING N N 29 
FRR C34 H341 SING N N 30 
FRR C34 H342 SING N N 31 
FRR C39 H39  SING N N 32 
FRR C39 O44  SING N N 33 
FRR C39 C40  SING N N 34 
FRR C40 O40  DOUB N N 35 
FRR C40 C41  SING N N 36 
FRR C41 H41  SING N N 37 
FRR C41 C42  DOUB N N 38 
FRR C42 H1   SING N N 39 
FRR O42 H42  SING N N 40 
FRR O44 H44  SING N N 41 
FRR O46 H46  SING N N 42 
FRR O48 C59  SING N N 43 
FRR C59 H591 SING N N 44 
FRR C59 H592 SING N N 45 
FRR C59 H593 SING N N 46 
FRR C62 H621 SING N N 47 
FRR C62 H622 SING N N 48 
FRR C62 H623 SING N N 49 
# 
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 
FRR SMILES           ACDLabs              10.04 O=C1OC(CC=CC(=O)C(O)C(O)CC=Cc2cc(OC)cc(O)c12)C                                                                                                                    
FRR InChI            InChI                1.02b InChI=1/C19H22O7/c1-11-5-3-7-14(20)18(23)15(21)8-4-6-12-9-13(25-2)10-16(22)17(12)19(24)26-11/h3-4,6-7,9-11,15,18,21-23H,5,8H2,1-2H3/b6-4+,7-3-/t11-,15+,18-/m1/s1 
FRR InChIKey         InChI                1.02b NEQZWEXWOFPKOT-QHSZRYGNBE                                                                                                                                         
FRR SMILES_CANONICAL CACTVS               3.341 COc1cc(O)c2C(=O)O[C@H](C)C\C=C/C(=O)[C@@H](O)[C@@H](O)C/C=C/c2c1                                                                                                  
FRR SMILES           CACTVS               3.341 COc1cc(O)c2C(=O)O[CH](C)CC=CC(=O)[CH](O)[CH](O)CC=Cc2c1                                                                                                           
FRR SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 C[C@@H]1CC=CC(=O)[C@H]([C@H](C\C=C\c2cc(cc(c2C(=O)O1)O)OC)O)O                                                                                                     
FRR SMILES           "OpenEye OEToolkits" 1.5.0 CC1CC=CC(=O)C(C(CC=Cc2cc(cc(c2C(=O)O1)O)OC)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 
FRR "SYSTEMATIC NAME" ACDLabs              10.04 (3R,5Z,8S,9S,11E)-8,9,16-trihydroxy-14-methoxy-3-methyl-3,4,9,10-tetrahydro-1H-2-benzoxacyclotetradecine-1,7(8H)-dione  
FRR "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 (4R,9S,10S,12E)-9,10,18-trihydroxy-16-methoxy-4-methyl-3-oxabicyclo[12.4.0]octadeca-1(18),6,12,14,16-pentaene-2,8-dione 
# 
