data_F5M # _chem_comp.id F5M _chem_comp.name "5-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)-2-(6-hydroxy-3-oxo-3H-xanthen-9-yl)benzoic acid" _chem_comp.type NON-POLYMER _chem_comp.pdbx_type HETAIN _chem_comp.formula "C24 H13 N O7" _chem_comp.mon_nstd_parent_comp_id ? _chem_comp.pdbx_synonyms fluorescein-5-maleimide _chem_comp.pdbx_formal_charge 0 _chem_comp.pdbx_initial_date 2010-04-13 _chem_comp.pdbx_modified_date 2021-03-01 _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 427.363 _chem_comp.one_letter_code ? _chem_comp.three_letter_code F5M _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 3M2J _chem_comp.pdbx_subcomponent_list ? _chem_comp.pdbx_processing_site PDBJ # # 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 F5M C1 C1 C 0 1 Y N N 17.740 12.668 20.003 3.564 -3.598 0.184 C1 F5M 1 F5M O1 O1 O 0 1 N N N 18.363 13.421 20.907 4.294 -4.732 0.335 O1 F5M 2 F5M C2 C2 C 0 1 Y N N 18.280 11.941 19.104 4.209 -2.383 0.023 C2 F5M 3 F5M O2 O2 O 0 1 N N N 19.024 10.433 17.304 4.086 -0.034 -0.290 O2 F5M 4 F5M C3 C3 C 0 1 Y N N 18.142 11.123 18.104 3.467 -1.221 -0.132 C3 F5M 5 F5M O3 O3 O 0 1 N N N 19.766 8.226 13.243 4.013 4.558 -0.900 O3 F5M 6 F5M C4 C4 C 0 1 N N N 18.514 9.603 16.306 3.407 1.122 -0.444 C4 F5M 7 F5M O4 O4 O 0 1 N N N 14.729 6.555 16.516 1.032 0.877 2.038 O4 F5M 8 F5M C5 C5 C 0 1 N N N 19.445 8.922 15.517 4.098 2.307 -0.601 C5 F5M 9 F5M O5 O5 O 0 1 N N N 14.556 7.454 18.593 -0.868 1.283 3.110 O5 F5M 10 F5M C6 C6 C 0 1 N N N 19.055 7.979 14.457 3.398 3.508 -0.761 C6 F5M 11 F5M C7 C7 C 0 1 N N N 17.594 7.887 14.254 1.988 3.516 -0.763 C7 F5M 12 F5M C8 C8 C 0 1 N N N 16.684 8.578 15.050 1.299 2.357 -0.609 C8 F5M 13 F5M C9 C9 C 0 1 N N N 17.116 9.432 16.076 1.991 1.142 -0.447 C9 F5M 14 F5M C10 C10 C 0 1 N N N 16.090 10.134 16.930 1.279 -0.069 -0.288 C10 F5M 15 F5M C11 C11 C 0 1 Y N N 16.665 11.026 17.946 2.059 -1.299 -0.124 C11 F5M 16 F5M C12 C12 C 0 1 Y N N 16.141 11.774 18.861 1.423 -2.537 0.040 C12 F5M 17 F5M C13 C13 C 0 1 Y N N 16.253 12.548 19.864 2.170 -3.668 0.185 C13 F5M 18 F5M C14 C14 C 0 1 Y N N 14.621 9.991 16.652 -0.192 -0.094 -0.286 C14 F5M 19 F5M C15 C15 C 0 1 Y N N 13.989 11.111 16.156 -0.888 -0.568 -1.400 C15 F5M 20 F5M C16 C16 C 0 1 Y N N 12.643 11.108 15.804 -2.266 -0.590 -1.396 C16 F5M 21 F5M C17 C17 C 0 1 Y N N 11.819 9.992 15.923 -2.973 -0.142 -0.285 C17 F5M 22 F5M C18 C18 C 0 1 Y N N 12.409 8.805 16.427 -2.296 0.334 0.833 C18 F5M 23 F5M C19 C19 C 0 1 Y N N 13.783 8.756 16.776 -0.907 0.357 0.845 C19 F5M 24 F5M C20 C20 C 0 1 N N N 14.404 7.498 17.321 -0.182 0.854 2.033 C20 F5M 25 F5M NAB NAB N 0 1 N N N 10.495 10.167 15.546 -4.370 -0.169 -0.293 NAB F5M 26 F5M CAZ CAZ C 0 1 N N N 9.544 9.272 15.439 -5.131 -0.604 -1.312 CAZ F5M 27 F5M CBA CBA C 0 1 N N N 8.184 9.880 15.156 -6.552 -0.468 -0.925 CBA F5M 28 F5M CBB CBB C 0 1 N N N 8.549 11.281 14.682 -6.569 0.046 0.316 CBB F5M 29 F5M CBC CBC C 0 1 N N N 10.013 11.313 15.088 -5.159 0.232 0.721 CBC F5M 30 F5M OBJ OBJ O 0 1 N N N 10.677 12.338 15.060 -4.777 0.673 1.786 OBJ F5M 31 F5M OBK OBK O 0 1 N N N 9.774 8.033 15.347 -4.721 -1.036 -2.370 OBK F5M 32 F5M HO1 HO1 H 0 1 N N N 17.720 13.857 21.454 4.504 -4.944 1.255 HO1 F5M 33 F5M H2 H2 H 0 1 N N N 19.345 12.061 19.235 5.289 -2.340 0.019 H2 F5M 34 F5M H5 H5 H 0 1 N N N 20.496 9.095 15.693 5.178 2.307 -0.600 H5 F5M 35 F5M HO5 HO5 H 0 1 N N N 14.943 6.621 18.838 -0.351 1.600 3.863 HO5 F5M 36 F5M H7 H7 H 0 1 N N N 17.218 7.260 13.459 1.454 4.447 -0.887 H7 F5M 37 F5M H8 H8 H 0 1 N N N 15.626 8.454 14.874 0.219 2.367 -0.611 H8 F5M 38 F5M H12 H12 H 0 1 N N N 15.077 11.709 18.687 0.345 -2.595 0.046 H12 F5M 39 F5M H13 H13 H 0 1 N N N 15.476 13.002 20.462 1.680 -4.623 0.307 H13 F5M 40 F5M H15 H15 H 0 1 N N N 14.558 12.021 16.037 -0.345 -0.918 -2.266 H15 F5M 41 F5M H16 H16 H 0 1 N N N 12.214 12.021 15.418 -2.800 -0.957 -2.260 H16 F5M 42 F5M H18 H18 H 0 1 N N N 11.800 7.921 16.547 -2.850 0.681 1.693 H18 F5M 43 F5M HBA HBA H 0 1 N N N 7.206 9.434 15.263 -7.411 -0.731 -1.525 HBA F5M 44 F5M HBB HBB H 0 1 N N N 7.943 12.033 14.198 -7.444 0.276 0.906 HBB F5M 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 F5M C1 O1 SING N N 1 F5M C1 C2 DOUB Y N 2 F5M C1 C13 SING Y N 3 F5M C2 C3 SING Y N 4 F5M O2 C3 SING N N 5 F5M O2 C4 SING N N 6 F5M C3 C11 DOUB Y N 7 F5M O3 C6 DOUB N N 8 F5M C4 C5 DOUB N N 9 F5M C4 C9 SING N N 10 F5M O4 C20 DOUB N N 11 F5M C5 C6 SING N N 12 F5M O5 C20 SING N N 13 F5M C6 C7 SING N N 14 F5M C7 C8 DOUB N N 15 F5M C8 C9 SING N N 16 F5M C9 C10 DOUB N N 17 F5M C10 C11 SING N N 18 F5M C10 C14 SING N N 19 F5M C11 C12 SING Y N 20 F5M C12 C13 DOUB Y N 21 F5M C14 C15 DOUB Y N 22 F5M C14 C19 SING Y N 23 F5M C15 C16 SING Y N 24 F5M C16 C17 DOUB Y N 25 F5M C17 C18 SING Y N 26 F5M C17 NAB SING N N 27 F5M C18 C19 DOUB Y N 28 F5M C19 C20 SING N N 29 F5M NAB CAZ SING N N 30 F5M NAB CBC SING N N 31 F5M CAZ CBA SING N N 32 F5M CAZ OBK DOUB N N 33 F5M CBA CBB DOUB N N 34 F5M CBB CBC SING N N 35 F5M CBC OBJ DOUB N N 36 F5M O1 HO1 SING N N 37 F5M C2 H2 SING N N 38 F5M C5 H5 SING N N 39 F5M O5 HO5 SING N N 40 F5M C7 H7 SING N N 41 F5M C8 H8 SING N N 42 F5M C12 H12 SING N N 43 F5M C13 H13 SING N N 44 F5M C15 H15 SING N N 45 F5M C16 H16 SING N N 46 F5M C18 H18 SING N N 47 F5M CBA HBA SING N N 48 F5M CBB HBB 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 F5M SMILES ACDLabs 12.01 "O=C1C=CC(=O)N1c5ccc(C=2c4c(OC=3C=2C=CC(=O)C=3)cc(O)cc4)c(C(=O)O)c5" F5M SMILES_CANONICAL CACTVS 3.370 "OC(=O)c1cc(ccc1C2=C3C=CC(=O)C=C3Oc4cc(O)ccc24)N5C(=O)C=CC5=O" F5M SMILES CACTVS 3.370 "OC(=O)c1cc(ccc1C2=C3C=CC(=O)C=C3Oc4cc(O)ccc24)N5C(=O)C=CC5=O" F5M SMILES_CANONICAL "OpenEye OEToolkits" 1.7.0 "c1cc(c(cc1N2C(=O)C=CC2=O)C(=O)O)C3=C4C=CC(=O)C=C4Oc5c3ccc(c5)O" F5M SMILES "OpenEye OEToolkits" 1.7.0 "c1cc(c(cc1N2C(=O)C=CC2=O)C(=O)O)C3=C4C=CC(=O)C=C4Oc5c3ccc(c5)O" F5M InChI InChI 1.03 "InChI=1S/C24H13NO7/c26-13-2-5-16-19(10-13)32-20-11-14(27)3-6-17(20)23(16)15-4-1-12(9-18(15)24(30)31)25-21(28)7-8-22(25)29/h1-11,26H,(H,30,31)" F5M InChIKey InChI 1.03 HFBMFFXWMZRDIY-UHFFFAOYSA-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 F5M "SYSTEMATIC NAME" ACDLabs 12.01 "5-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)-2-(6-hydroxy-3-oxo-3H-xanthen-9-yl)benzoic acid" F5M "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.7.0 "5-(2,5-dioxopyrrol-1-yl)-2-(3-hydroxy-6-oxo-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 F5M "Create component" 2010-04-13 PDBJ F5M "Modify aromatic_flag" 2011-06-04 RCSB F5M "Modify descriptor" 2011-06-04 RCSB F5M "Modify synonyms" 2021-03-01 PDBE # _pdbx_chem_comp_synonyms.ordinal 1 _pdbx_chem_comp_synonyms.comp_id F5M _pdbx_chem_comp_synonyms.name fluorescein-5-maleimide _pdbx_chem_comp_synonyms.provenance ? _pdbx_chem_comp_synonyms.type ? ##