data_FL9
# 
_chem_comp.id                                    FL9 
_chem_comp.name                                  
;3',5'-DIBROMO-2',4,4',6'-TETRAHYDROXY AURONE
;
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C15 H8 Br2 O6" 
_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                        444.028 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     FL9 
_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        1THC 
_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 
FL9 C2     C2   C  0 1 N N N 22.241 43.489 27.075 -1.288 -0.271 1.787  C2     FL9 1  
FL9 C3     C3   C  0 1 N N N 22.095 43.341 28.549 -2.048 -0.251 3.043  C3     FL9 2  
FL9 C3A    C3A  C  0 1 Y N N 20.868 44.052 28.841 -1.033 -0.039 4.087  C3A    FL9 3  
FL9 C4     C4   C  0 1 Y N N 20.166 44.303 30.018 -1.102 0.074  5.482  C4     FL9 4  
FL9 C5     C5   C  0 1 Y N N 19.003 45.034 29.972 0.056  0.275  6.209  C5     FL9 5  
FL9 C6     C6   C  0 1 Y N N 18.546 45.487 28.741 1.280  0.363  5.555  C6     FL9 6  
FL9 C7     C7   C  0 1 Y N N 19.213 45.283 27.536 1.353  0.256  4.175  C7     FL9 7  
FL9 C7A    C7A  C  0 1 Y N N 20.363 44.558 27.639 0.202  0.049  3.426  C7A    FL9 8  
FL9 C21    C21  C  0 1 N N N 22.950 42.733 26.224 -1.802 -0.442 0.540  C21    FL9 9  
FL9 "C1'"  C1*  C  0 1 Y N N 22.578 42.838 24.795 -0.942 -0.281 -0.635 "C1'"  FL9 10 
FL9 "C2'"  C2*  C  0 1 Y N N 22.391 41.631 24.096 -1.512 -0.107 -1.908 "C2'"  FL9 11 
FL9 "C3'"  C3*  C  0 1 Y N N 22.038 41.684 22.739 -0.691 0.049  -3.012 "C3'"  FL9 12 
FL9 "C4'"  C4*  C  0 1 Y N N 21.875 42.896 22.069 0.687  0.022  -2.862 "C4'"  FL9 13 
FL9 "C5'"  C5*  C  0 1 Y N N 22.058 44.066 22.797 1.254  -0.154 -1.603 "C5'"  FL9 14 
FL9 "C6'"  C6*  C  0 1 Y N N 22.399 44.056 24.139 0.451  -0.306 -0.496 "C6'"  FL9 15 
FL9 BR1    BR1  BR 0 0 N N N 21.786 40.106 21.766 -1.451 0.290  -4.727 BR1    FL9 16 
FL9 BR2    BR2  BR 0 0 N N N 21.834 45.715 21.909 3.136  -0.189 -1.413 BR2    FL9 17 
FL9 O1     O1   O  0 1 N N N 21.158 44.242 26.582 0.017  -0.089 2.095  O1     FL9 18 
FL9 O3     O3   O  0 1 N N N 22.854 42.748 29.299 -3.252 -0.381 3.189  O3     FL9 19 
FL9 O4     O4   O  0 1 N N N 20.640 43.827 31.204 -2.299 -0.011 6.115  O4     FL9 20 
FL9 O6     O6   O  0 1 N N N 17.382 46.207 28.714 2.413  0.561  6.275  O6     FL9 21 
FL9 "O2'"  O2*  O  0 1 N N N 22.565 40.496 24.761 -2.861 -0.082 -2.053 "O2'"  FL9 22 
FL9 "O4'"  O4*  O  0 1 N N N 21.528 42.872 20.762 1.488  0.170  -3.949 "O4'"  FL9 23 
FL9 H5     H5   H  0 1 N N N 18.449 45.251 30.900 0.011  0.364  7.284  H5     FL9 24 
FL9 H7     H7   H  0 1 N N N 18.855 45.669 26.566 2.310  0.331  3.680  H7     FL9 25 
FL9 H21    H21  H  0 1 N N N 23.746 42.099 26.649 -2.844 -0.697 0.416  H21    FL9 26 
FL9 "H6'"  H6*  H  0 1 N N N 22.526 45.008 24.680 0.895  -0.443 0.479  "H6'"  FL9 27 
FL9 HO4    HO4  H  0 1 N N N 20.161 43.998 32.006 -2.654 0.886  6.165  HO4    FL9 28 
FL9 HO6    HO6  H  0 1 N N N 17.069 46.516 27.872 2.756  -0.313 6.504  HO6    FL9 29 
FL9 "HO2'" *HO2 H  0 0 N N N 22.438 39.681 24.289 -3.142 -0.993 -2.215 "HO2'" FL9 30 
FL9 "HO4'" *HO4 H  0 0 N N N 21.417 43.697 20.305 1.649  -0.715 -4.300 "HO4'" FL9 31 
# 
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 
FL9 C2    C3     SING N N 1  
FL9 C2    C21    DOUB N Z 2  
FL9 C2    O1     SING N N 3  
FL9 C3    C3A    SING N N 4  
FL9 C3    O3     DOUB N N 5  
FL9 C3A   C4     DOUB Y N 6  
FL9 C3A   C7A    SING Y N 7  
FL9 C4    C5     SING Y N 8  
FL9 C4    O4     SING N N 9  
FL9 C5    C6     DOUB Y N 10 
FL9 C5    H5     SING N N 11 
FL9 C6    C7     SING Y N 12 
FL9 C6    O6     SING N N 13 
FL9 C7    C7A    DOUB Y N 14 
FL9 C7    H7     SING N N 15 
FL9 C7A   O1     SING N N 16 
FL9 C21   "C1'"  SING N N 17 
FL9 C21   H21    SING N N 18 
FL9 "C1'" "C2'"  DOUB Y N 19 
FL9 "C1'" "C6'"  SING Y N 20 
FL9 "C2'" "C3'"  SING Y N 21 
FL9 "C2'" "O2'"  SING N N 22 
FL9 "C3'" "C4'"  DOUB Y N 23 
FL9 "C3'" BR1    SING N N 24 
FL9 "C4'" "C5'"  SING Y N 25 
FL9 "C4'" "O4'"  SING N N 26 
FL9 "C5'" "C6'"  DOUB Y N 27 
FL9 "C5'" BR2    SING N N 28 
FL9 "C6'" "H6'"  SING N N 29 
FL9 O4    HO4    SING N N 30 
FL9 O6    HO6    SING N N 31 
FL9 "O2'" "HO2'" SING N N 32 
FL9 "O4'" "HO4'" SING N N 33 
# 
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 
FL9 SMILES           ACDLabs              10.04 Brc1cc(c(O)c(Br)c1O)\C=C3/Oc2cc(O)cc(O)c2C3=O                                                              
FL9 InChI            InChI                1.02b InChI=1/C15H8Br2O6/c16-7-1-5(13(20)12(17)14(7)21)2-10-15(22)11-8(19)3-6(18)4-9(11)23-10/h1-4,18-21H/b10-2- 
FL9 InChIKey         InChI                1.02b BRPKBUNFOZFULQ-SGAXSIHGBH                                                                                  
FL9 SMILES_CANONICAL CACTVS               3.341 Oc1cc(O)c2C(=O)\C(Oc2c1)=C\c3cc(Br)c(O)c(Br)c3O                                                            
FL9 SMILES           CACTVS               3.341 Oc1cc(O)c2C(=O)C(Oc2c1)=Cc3cc(Br)c(O)c(Br)c3O                                                              
FL9 SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 c1c(cc2c(c1O)C(=O)C(=Cc3cc(c(c(c3O)Br)O)Br)O2)O                                                            
FL9 SMILES           "OpenEye OEToolkits" 1.5.0 c1c(cc2c(c1O)C(=O)C(=Cc3cc(c(c(c3O)Br)O)Br)O2)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 
FL9 "SYSTEMATIC NAME" ACDLabs              10.04 (2Z)-2-[(3,5-dibromo-2,4-dihydroxyphenyl)methylidene]-4,6-dihydroxy-1-benzofuran-3(2H)-one 
FL9 "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 2-[(3,5-dibromo-2,4-dihydroxy-phenyl)methylidene]-4,6-dihydroxy-1-benzofuran-3-one         
# 
