data_A4F
#

_chem_comp.id                                   A4F
_chem_comp.name                                 "5-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                              "C20 H13 N O5"
_chem_comp.mon_nstd_parent_comp_id              ?
_chem_comp.pdbx_synonyms                        5-aminofluorescein
_chem_comp.pdbx_formal_charge                   0
_chem_comp.pdbx_initial_date                    2015-05-20
_chem_comp.pdbx_modified_date                   2020-06-17
_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                       347.321
_chem_comp.one_letter_code                      ?
_chem_comp.three_letter_code                    A4F
_chem_comp.pdbx_model_coordinates_details       ?
_chem_comp.pdbx_model_coordinates_missing_flag  N
_chem_comp.pdbx_ideal_coordinates_details       Corina
_chem_comp.pdbx_ideal_coordinates_missing_flag  N
_chem_comp.pdbx_model_coordinates_db_code       4ZS3
_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
A4F  O5   O1   O  0  1  N  N  N  177.839   5.548  33.872  -2.583   0.537   2.897  O5   A4F   1  
A4F  C17  C1   C  0  1  N  N  N  177.219   6.364  33.149  -1.737   0.338   1.869  C17  A4F   2  
A4F  O4   O2   O  0  1  N  N  N  177.226   6.282  31.904  -0.560   0.618   1.987  O4   A4F   3  
A4F  C18  C2   C  0  1  Y  N  N  176.436   7.445  33.772  -2.239  -0.220   0.596  C18  A4F   4  
A4F  C19  C3   C  0  1  Y  N  N  177.085   8.287  34.674  -3.583  -0.540   0.456  C19  A4F   5  
A4F  C20  C4   C  0  1  Y  N  N  176.383   9.315  35.290  -4.050  -1.065  -0.746  C20  A4F   6  
A4F  N1   N1   N  0  1  N  N  N  176.983  10.123  36.149  -5.396  -1.385  -0.884  N1   A4F   7  
A4F  C16  C5   C  0  1  Y  N  N  175.036   9.489  34.992  -3.176  -1.271  -1.810  C16  A4F   8  
A4F  C15  C6   C  0  1  Y  N  N  174.390   8.640  34.091  -1.841  -0.957  -1.685  C15  A4F   9  
A4F  C14  C7   C  0  1  Y  N  N  175.078   7.610  33.454  -1.356  -0.424  -0.487  C14  A4F  10  
A4F  C1   C8   C  0  1  N  N  N  174.407   6.760  32.583   0.068  -0.083  -0.353  C1   A4F  11  
A4F  C13  C9   C  0  1  Y  N  N  173.807   7.210  31.376   1.088  -1.125  -0.196  C13  A4F  12  
A4F  C12  C10  C  0  1  Y  N  N  174.111   8.445  30.792   0.731  -2.479  -0.162  C12  A4F  13  
A4F  C11  C11  C  0  1  Y  N  N  173.488   8.847  29.604   1.696  -3.431  -0.015  C11  A4F  14  
A4F  C10  C12  C  0  1  Y  N  N  172.548   8.025  28.981   3.037  -3.062   0.103  C10  A4F  15  
A4F  O3   O3   O  0  1  N  N  N  171.930   8.390  27.851   3.987  -4.020   0.250  O3   A4F  16  
A4F  C9   C13  C  0  1  Y  N  N  172.244   6.802  29.552   3.408  -1.728   0.073  C9   A4F  17  
A4F  C8   C14  C  0  1  Y  N  N  172.865   6.406  30.723   2.440  -0.745  -0.077  C8   A4F  18  
A4F  O2   O4   O  0  1  N  N  N  172.508   5.181  31.236   2.790   0.557  -0.108  O2   A4F  19  
A4F  C2   C15  C  0  1  N  N  N  174.030   5.494  33.087   0.505   1.262  -0.378  C2   A4F  20  
A4F  C7   C16  C  0  1  N  N  N  173.083   4.717  32.410   1.885   1.547  -0.252  C7   A4F  21  
A4F  C6   C17  C  0  1  N  N  N  172.700   3.469  32.901   2.307   2.862  -0.277  C6   A4F  22  
A4F  C3   C18  C  0  1  N  N  N  174.576   4.978  34.276  -0.425   2.308  -0.533  C3   A4F  23  
A4F  C4   C19  C  0  1  N  N  N  174.200   3.728  34.753   0.000   3.596  -0.555  C4   A4F  24  
A4F  C5   C20  C  0  1  N  N  N  173.260   2.973  34.074   1.372   3.893  -0.425  C5   A4F  25  
A4F  O1   O5   O  0  1  N  N  N  172.905   1.782  34.554   1.749   5.059  -0.447  O1   A4F  26  
A4F  H1   H1   H  0  1  N  N  N  178.278   4.908  33.324  -2.208   0.904   3.710  H1   A4F  27  
A4F  H2   H2   H  0  1  N  N  N  178.132   8.140  34.893  -4.265  -0.383   1.279  H2   A4F  28  
A4F  H3   H3   H  0  1  N  N  N  176.326  10.796  36.488  -6.007  -1.243  -0.144  H3   A4F  29  
A4F  H4   H4   H  0  1  N  N  N  177.339   9.589  36.916  -5.724  -1.751  -1.720  H4   A4F  30  
A4F  H5   H5   H  0  1  N  N  N  174.484  10.289  35.462  -3.547  -1.679  -2.739  H5   A4F  31  
A4F  H6   H6   H  0  1  N  N  N  173.340   8.784  33.885  -1.168  -1.119  -2.514  H6   A4F  32  
A4F  H7   H7   H  0  1  N  N  N  174.834   9.095  31.263  -0.306  -2.768  -0.253  H7   A4F  33  
A4F  H8   H8   H  0  1  N  N  N  173.737   9.802  29.166   1.422  -4.475   0.010  H8   A4F  34  
A4F  H9   H9   H  0  1  N  N  N  172.240   9.247  27.582   4.172  -4.253   1.170  H9   A4F  35  
A4F  H10  H10  H  0  1  N  N  N  171.519   6.154  29.082   4.448  -1.453   0.166  H10  A4F  36  
A4F  H11  H11  H  0  1  N  N  N  171.965   2.885  32.368   3.358   3.095  -0.181  H11  A4F  37  
A4F  H12  H12  H  0  1  N  N  N  175.298   5.562  34.827  -1.477   2.085  -0.633  H12  A4F  38  
A4F  H13  H13  H  0  1  N  N  N  174.644   3.344  35.659  -0.715   4.397  -0.674  H13  A4F  39  
#   #
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
A4F  O3   C10  SING  N  N   1  
A4F  C10  C9   DOUB  Y  N   2  
A4F  C10  C11  SING  Y  N   3  
A4F  C9   C8   SING  Y  N   4  
A4F  C11  C12  DOUB  Y  N   5  
A4F  C8   O2   SING  N  N   6  
A4F  C8   C13  DOUB  Y  N   7  
A4F  C12  C13  SING  Y  N   8  
A4F  O2   C7   SING  N  N   9  
A4F  C13  C1   SING  N  N  10  
A4F  O4   C17  DOUB  N  N  11  
A4F  C7   C6   DOUB  N  N  12  
A4F  C7   C2   SING  N  N  13  
A4F  C1   C2   DOUB  N  N  14  
A4F  C1   C14  SING  N  N  15  
A4F  C6   C5   SING  N  N  16  
A4F  C2   C3   SING  N  N  17  
A4F  C17  C18  SING  N  N  18  
A4F  C17  O5   SING  N  N  19  
A4F  C14  C18  DOUB  Y  N  20  
A4F  C14  C15  SING  Y  N  21  
A4F  C18  C19  SING  Y  N  22  
A4F  C5   O1   DOUB  N  N  23  
A4F  C5   C4   SING  N  N  24  
A4F  C15  C16  DOUB  Y  N  25  
A4F  C3   C4   DOUB  N  N  26  
A4F  C19  C20  DOUB  Y  N  27  
A4F  C16  C20  SING  Y  N  28  
A4F  C20  N1   SING  N  N  29  
A4F  O5   H1   SING  N  N  30  
A4F  C19  H2   SING  N  N  31  
A4F  N1   H3   SING  N  N  32  
A4F  N1   H4   SING  N  N  33  
A4F  C16  H5   SING  N  N  34  
A4F  C15  H6   SING  N  N  35  
A4F  C12  H7   SING  N  N  36  
A4F  C11  H8   SING  N  N  37  
A4F  O3   H9   SING  N  N  38  
A4F  C9   H10  SING  N  N  39  
A4F  C6   H11  SING  N  N  40  
A4F  C3   H12  SING  N  N  41  
A4F  C4   H13  SING  N  N  42  
#   #
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
A4F  SMILES            ACDLabs               12.01  "OC(c1cc(N)ccc1C2=C4C=CC(C=C4Oc3c2ccc(c3)O)=O)=O"  
A4F  InChI             InChI                 1.03   "InChI=1S/C20H13NO5/c21-10-1-4-13(16(7-10)20(24)25)19-14-5-2-11(22)8-17(14)26-18-9-12(23)3-6-15(18)19/h1-9,22H,21H2,(H,24,25)"  
A4F  InChIKey          InChI                 1.03   UTUYQGGHTUQHQQ-UHFFFAOYSA-N  
A4F  SMILES_CANONICAL  CACTVS                3.385  "Nc1ccc(c(c1)C(O)=O)C2=C3C=CC(=O)C=C3Oc4cc(O)ccc24"  
A4F  SMILES            CACTVS                3.385  "Nc1ccc(c(c1)C(O)=O)C2=C3C=CC(=O)C=C3Oc4cc(O)ccc24"  
A4F  SMILES_CANONICAL  "OpenEye OEToolkits"  1.9.2  "c1cc(c(cc1N)C(=O)O)C2=C3C=CC(=O)C=C3Oc4c2ccc(c4)O"  
A4F  SMILES            "OpenEye OEToolkits"  1.9.2  "c1cc(c(cc1N)C(=O)O)C2=C3C=CC(=O)C=C3Oc4c2ccc(c4)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
A4F  "SYSTEMATIC NAME"  ACDLabs               12.01  "5-amino-2-(6-hydroxy-3-oxo-3H-xanthen-9-yl)benzoic acid"  
A4F  "SYSTEMATIC NAME"  "OpenEye OEToolkits"  1.9.2  "5-azanyl-2-(3-oxidanyl-6-oxidanylidene-xanthen-9-yl)benzoic acid"  
#   #
loop_
_pdbx_chem_comp_audit.comp_id
_pdbx_chem_comp_audit.action_type
_pdbx_chem_comp_audit.date
_pdbx_chem_comp_audit.processing_site
A4F  "Create component"  2015-05-20  RCSB  
A4F  "Modify synonyms"   2015-06-29  RCSB  
A4F  "Initial release"   2015-11-04  RCSB  
A4F  "Modify synonyms"   2020-06-05  PDBE  
#
_pdbx_chem_comp_synonyms.ordinal     1
_pdbx_chem_comp_synonyms.comp_id     A4F
_pdbx_chem_comp_synonyms.name        5-aminofluorescein
_pdbx_chem_comp_synonyms.provenance  ?
_pdbx_chem_comp_synonyms.type        ?
##
