data_FL1
# 
_chem_comp.id                                    FL1 
_chem_comp.name                                  "5-{[({2-[4-(AMINOSULFONYL)PHENYL]ETHYL}AMINO)CARBONOTHIOYL]AMINO}-2-(6-HYDROXY-3-OXO-3H-XANTHEN-9-YL)BENZOIC ACID" 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C29 H23 N3 O7 S2" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         (4-SULFAMOYLPHENYLETHYLTHIOUREIDO)FLUORESCEIN 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2005-11-18 
_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                        589.639 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     FL1 
_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   Y 
_chem_comp.pdbx_model_coordinates_db_code        2F14 
_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 
FL1 S1   S1   S 0 1 N N N -6.017 0.883  16.916 10.009 0.666  1.227  S1   FL1 1  
FL1 O1   O1   O 0 1 N N N -5.454 0.995  18.244 9.935  0.022  2.492  O1   FL1 2  
FL1 O2   O2   O 0 1 N N N -7.450 0.947  16.776 10.085 2.070  1.022  O2   FL1 3  
FL1 N1   N1   N 0 1 N N N -5.491 -0.495 16.283 11.339 0.029  0.475  N1   FL1 4  
FL1 C1   C1   C 0 1 Y N N -5.336 2.213  15.941 8.589  0.128  0.332  C1   FL1 5  
FL1 C2   C2   C 0 1 Y N N -3.970 2.158  15.595 7.961  -1.054 0.678  C2   FL1 6  
FL1 C3   C3   C 0 1 Y N N -3.447 3.177  14.849 6.848  -1.476 -0.024 C3   FL1 7  
FL1 C4   C4   C 0 1 Y N N -4.228 4.283  14.413 6.362  -0.715 -1.072 C4   FL1 8  
FL1 C5   C5   C 0 1 Y N N -5.600 4.313  14.776 6.989  0.467  -1.416 C5   FL1 9  
FL1 C6   C6   C 0 1 Y N N -6.167 3.302  15.530 8.100  0.891  -0.712 C6   FL1 10 
FL1 C7   C7   C 0 1 N N N -3.605 5.409  13.571 5.148  -1.175 -1.837 C7   FL1 11 
FL1 C29  C29  C 0 1 N N N -2.078 5.404  13.580 3.887  -0.612 -1.180 C29  FL1 12 
FL1 N2   N2   N 0 1 N N N -1.535 6.575  12.937 2.707  -1.060 -1.924 N2   FL1 13 
FL1 C8   C8   C 0 1 N N N -1.671 7.811  13.379 1.476  -0.684 -1.525 C8   FL1 14 
FL1 S2   S2   S 0 1 N N N -1.748 8.187  15.022 1.291  0.317  -0.148 S2   FL1 15 
FL1 N3   N3   N 0 1 N N N -1.737 8.743  12.395 0.390  -1.095 -2.210 N3   FL1 16 
FL1 C9   C9   C 0 1 Y N N -1.881 10.157 12.335 -0.886 -0.808 -1.730 C9   FL1 17 
FL1 C10  C10  C 0 1 Y N N -1.840 10.927 13.515 -1.882 -0.399 -2.613 C10  FL1 18 
FL1 C11  C11  C 0 1 Y N N -1.975 12.322 13.460 -3.148 -0.113 -2.151 C11  FL1 19 
FL1 C12  C12  C 0 1 Y N N -2.157 12.985 12.201 -3.439 -0.231 -0.789 C12  FL1 20 
FL1 C13  C13  C 0 1 Y N N -2.204 12.193 10.985 -2.431 -0.647 0.108  C13  FL1 21 
FL1 C14  C14  C 0 1 Y N N -2.063 10.796 11.093 -1.161 -0.938 -0.373 C14  FL1 22 
FL1 C15  C15  C 0 1 N N N -2.400 12.795 9.590  -2.727 -0.776 1.550  C15  FL1 23 
FL1 O3   O3   O 0 1 N N N -1.619 13.714 9.234  -1.763 -1.173 2.403  O3   FL1 24 
FL1 O4   O4   O 0 1 N N N -3.330 12.350 8.878  -3.840 -0.525 1.966  O4   FL1 25 
FL1 C16  C16  C 0 1 Y N N -2.290 14.518 12.249 -4.790 0.075  -0.293 C16  FL1 26 
FL1 C17  C17  C 0 1 Y N N 0.227  14.904 12.760 -4.427 2.532  -0.520 C17  FL1 27 
FL1 C18  C18  C 0 1 Y N N 1.267  15.783 13.006 -4.883 3.810  -0.394 C18  FL1 28 
FL1 C19  C19  C 0 1 Y N N 1.070  17.217 13.033 -6.172 4.056  0.082  C19  FL1 29 
FL1 C20  C20  C 0 1 Y N N -0.263 17.701 12.790 -7.006 3.007  0.435  C20  FL1 30 
FL1 C21  C21  C 0 1 Y N N -4.866 17.259 11.859 -7.844 -1.625 0.919  C21  FL1 31 
FL1 C22  C22  C 0 1 Y N N -6.072 16.520 11.589 -7.445 -2.963 0.817  C22  FL1 32 
FL1 C23  C23  C 0 1 Y N N -6.000 15.052 11.543 -6.157 -3.287 0.344  C23  FL1 33 
FL1 C24  C24  C 0 1 Y N N -4.809 14.403 11.752 -5.294 -2.304 -0.016 C24  FL1 34 
FL1 C25  C25  C 0 1 Y N N -3.559 15.132 12.025 -5.684 -0.954 0.082  C25  FL1 35 
FL1 C26  C26  C 0 1 Y N N -3.670 16.582 12.069 -6.974 -0.616 0.555  C26  FL1 36 
FL1 C27  C27  C 0 1 Y N N -1.134 15.364 12.511 -5.255 1.459  -0.162 C27  FL1 37 
FL1 C28  C28  C 0 1 Y N N -1.303 16.808 12.546 -6.560 1.699  0.315  C28  FL1 38 
FL1 O5   O5   O 0 1 Y N N -2.551 17.367 12.321 -7.363 0.671  0.655  O5   FL1 39 
FL1 O6   O6   O 0 1 N N N 2.089  18.023 13.270 -6.612 5.334  0.202  O6   FL1 40 
FL1 O7   O7   O 0 1 N N N -7.192 17.106 11.389 -8.219 -3.856 1.140  O7   FL1 41 
FL1 HN11 1HN1 H 0 0 N N N -4.610 -0.735 16.692 11.934 -0.563 0.961  HN11 FL1 42 
FL1 HN12 2HN1 H 0 0 N N N -5.382 -0.388 15.295 11.521 0.244  -0.453 HN12 FL1 43 
FL1 H2   H2   H 0 1 N N N -3.352 1.331  15.912 8.341  -1.648 1.496  H2   FL1 44 
FL1 H3   H3   H 0 1 N N N -2.402 3.141  14.581 6.357  -2.399 0.245  H3   FL1 45 
FL1 H5   H5   H 0 1 N N N -6.214 5.142  14.457 6.609  1.062  -2.234 H5   FL1 46 
FL1 H6   H6   H 0 1 N N N -7.212 3.334  15.802 8.591  1.815  -0.981 H6   FL1 47 
FL1 H71  1H7  H 0 1 N N N -3.930 6.363  14.012 5.211  -0.820 -2.866 H71  FL1 48 
FL1 H72  2H7  H 0 1 N N N -3.942 5.285  12.531 5.106  -2.265 -1.831 H72  FL1 49 
FL1 H291 1H29 H 0 0 N N N -1.734 4.518  13.026 3.823  -0.967 -0.151 H291 FL1 50 
FL1 H292 2H29 H 0 0 N N N -1.731 5.382  14.624 3.929  0.477  -1.187 H292 FL1 51 
FL1 HN2  HN2  H 0 1 N N N -1.016 6.440  12.093 2.812  -1.626 -2.705 HN2  FL1 52 
FL1 HN3  HN3  H 0 1 N N N -1.667 8.334  11.485 0.498  -1.591 -3.037 HN3  FL1 53 
FL1 H10  H10  H 0 1 N N N -1.704 10.439 14.469 -1.661 -0.306 -3.666 H10  FL1 54 
FL1 H11  H11  H 0 1 N N N -1.942 12.901 14.371 -3.915 0.205  -2.841 H11  FL1 55 
FL1 H14  H14  H 0 1 N N N -2.095 10.196 10.196 -0.385 -1.256 0.308  H14  FL1 56 
FL1 HO4  HO4  H 0 1 N N N -3.343 12.812 8.048  ?      ?      ?      HO4  FL1 57 
FL1 H17  H17  H 0 1 N N N 0.430  13.843 12.752 -3.430 2.346  -0.890 H17  FL1 58 
FL1 H18  H18  H 0 1 N N N 2.256  15.387 13.183 -4.244 4.638  -0.665 H18  FL1 59 
FL1 H20  H20  H 0 1 N N N -0.458 18.763 12.797 -8.001 3.208  0.803  H20  FL1 60 
FL1 H21  H21  H 0 1 N N N -4.891 18.338 11.898 -8.832 -1.382 1.282  H21  FL1 61 
FL1 H23  H23  H 0 1 N N N -6.893 14.479 11.343 -5.856 -4.322 0.267  H23  FL1 62 
FL1 H24  H24  H 0 1 N N N -4.788 13.324 11.715 -4.308 -2.556 -0.378 H24  FL1 63 
FL1 HO7  HO7  H 0 1 N N N -7.627 17.251 12.221 ?      ?      ?      HO7  FL1 64 
# 
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 
FL1 S1  O1   DOUB N N 1  
FL1 S1  O2   DOUB N N 2  
FL1 S1  N1   SING N N 3  
FL1 S1  C1   SING N N 4  
FL1 N1  HN11 SING N N 5  
FL1 N1  HN12 SING N N 6  
FL1 C1  C2   DOUB Y N 7  
FL1 C1  C6   SING Y N 8  
FL1 C2  C3   SING Y N 9  
FL1 C2  H2   SING N N 10 
FL1 C3  C4   DOUB Y N 11 
FL1 C3  H3   SING N N 12 
FL1 C4  C5   SING Y N 13 
FL1 C4  C7   SING N N 14 
FL1 C5  C6   DOUB Y N 15 
FL1 C5  H5   SING N N 16 
FL1 C6  H6   SING N N 17 
FL1 C7  C29  SING N N 18 
FL1 C7  H71  SING N N 19 
FL1 C7  H72  SING N N 20 
FL1 C29 N2   SING N N 21 
FL1 C29 H291 SING N N 22 
FL1 C29 H292 SING N N 23 
FL1 N2  C8   SING N N 24 
FL1 N2  HN2  SING N N 25 
FL1 C8  S2   DOUB N N 26 
FL1 C8  N3   SING N N 27 
FL1 N3  C9   SING N N 28 
FL1 N3  HN3  SING N N 29 
FL1 C9  C10  SING Y N 30 
FL1 C9  C14  DOUB Y N 31 
FL1 C10 C11  DOUB Y N 32 
FL1 C10 H10  SING N N 33 
FL1 C11 C12  SING Y N 34 
FL1 C11 H11  SING N N 35 
FL1 C12 C13  DOUB Y N 36 
FL1 C12 C16  SING N N 37 
FL1 C13 C14  SING Y N 38 
FL1 C13 C15  SING N N 39 
FL1 C14 H14  SING N N 40 
FL1 C15 O3   DOUB N N 41 
FL1 C15 O4   SING N N 42 
FL1 O4  HO4  SING N N 43 
FL1 C16 C25  SING Y N 44 
FL1 C16 C27  DOUB Y N 45 
FL1 C17 C18  DOUB Y N 46 
FL1 C17 C27  SING Y N 47 
FL1 C17 H17  SING N N 48 
FL1 C18 C19  SING Y N 49 
FL1 C18 H18  SING N N 50 
FL1 C19 C20  SING Y N 51 
FL1 C19 O6   DOUB N N 52 
FL1 C20 C28  DOUB Y N 53 
FL1 C20 H20  SING N N 54 
FL1 C21 C22  DOUB Y N 55 
FL1 C21 C26  SING Y N 56 
FL1 C21 H21  SING N N 57 
FL1 C22 C23  SING Y N 58 
FL1 C22 O7   SING N N 59 
FL1 C23 C24  DOUB Y N 60 
FL1 C23 H23  SING N N 61 
FL1 C24 C25  SING Y N 62 
FL1 C24 H24  SING N N 63 
FL1 C25 C26  DOUB Y N 64 
FL1 C26 O5   SING Y N 65 
FL1 C27 C28  SING N N 66 
FL1 C28 O5   SING Y N 67 
FL1 O7  HO7  SING N N 68 
# 
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 
FL1 SMILES           ACDLabs              10.04 O=S(=O)(N)c1ccc(cc1)CCNC(=S)Nc5ccc(C=2c4c(OC=3C=2C=CC(=O)C=3)cc(O)cc4)c(C(=O)O)c5 
FL1 InChI            InChI                1.02b 
InChI=1/C29H23N3O7S2/c30-41(37,38)20-6-1-16(2-7-20)11-12-31-29(40)32-17-3-8-21(24(13-17)28(35)36)27-22-9-4-18(33)14-25(22)39-26-15-19(34)5-10-23(26)27/h1-10,13-15,33H,11-12H2,(H,35,36)(H2,30,37,38)(H2,31,32,40)/f/h31-32,35H,30H2 
FL1 InChIKey         InChI                1.02b ZXJGFVGTIKDQMI-XXGHRNCBCI 
FL1 SMILES_CANONICAL CACTVS               3.341 N[S](=O)(=O)c1ccc(CCNC(=S)Nc2ccc(c(c2)C(O)=O)C3=C4C=CC(=O)C=C4Oc5cc(O)ccc35)cc1 
FL1 SMILES           CACTVS               3.341 N[S](=O)(=O)c1ccc(CCNC(=S)Nc2ccc(c(c2)C(O)=O)C3=C4C=CC(=O)C=C4Oc5cc(O)ccc35)cc1 
FL1 SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 c1cc(ccc1CCNC(=S)Nc2ccc(c(c2)C(=O)O)C3=C4C=CC(=O)C=C4Oc5c3ccc(c5)O)S(=O)(=O)N 
FL1 SMILES           "OpenEye OEToolkits" 1.5.0 c1cc(ccc1CCNC(=S)Nc2ccc(c(c2)C(=O)O)C3=C4C=CC(=O)C=C4Oc5c3ccc(c5)O)S(=O)(=O)N 
# 
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 
FL1 "SYSTEMATIC NAME" ACDLabs              10.04 "2-(6-hydroxy-3-oxo-3H-xanthen-9-yl)-5-({[2-(4-sulfamoylphenyl)ethyl]carbamothioyl}amino)benzoic acid" 
FL1 "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "2-(3-hydroxy-6-oxo-xanthen-9-yl)-5-[2-(4-sulfamoylphenyl)ethylcarbamothioylamino]benzoic acid"        
# 
