data_F89 # _chem_comp.id F89 _chem_comp.name "S)-2-(5(((1,2-DIHYDRO-3-METHYL-1-OXOBENZO(F)QUINAZOLIN-9-YL)METHYL)AMINO)1-OXO-2-ISOINDOLINYL)GLUTARIC ACID" _chem_comp.type NON-POLYMER _chem_comp.pdbx_type HETAIN _chem_comp.formula "C27 H24 N4 O6" _chem_comp.mon_nstd_parent_comp_id ? _chem_comp.pdbx_synonyms "FOLATE ANALOG 1843U89" _chem_comp.pdbx_formal_charge 0 _chem_comp.pdbx_initial_date 1999-07-08 _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 U18 _chem_comp.formula_weight 500.503 _chem_comp.one_letter_code ? _chem_comp.three_letter_code F89 _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 1SYN _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 F89 C1 C1 C 0 1 Y N N 46.857 37.044 24.079 1.766 -0.399 5.729 C1 F89 1 F89 O1A O1A O 0 1 N N N 46.039 37.671 24.746 1.966 -0.832 4.608 O1A F89 2 F89 N2 N2 N 0 1 Y N N 47.946 36.568 24.713 2.774 -0.276 6.625 N2 F89 3 F89 C3 C3 C 0 1 Y N N 48.750 35.643 24.158 2.528 0.203 7.871 C3 F89 4 F89 C3M C3M C 0 1 N N N 49.908 35.097 24.911 3.681 0.314 8.835 C3M F89 5 F89 N4 N4 N 0 1 Y N N 48.497 35.198 22.919 1.350 0.576 8.272 N4 F89 6 F89 C4A C4A C 0 1 Y N N 47.488 35.708 22.193 0.270 0.506 7.466 C4A F89 7 F89 C5 C5 C 0 1 Y N N 47.225 35.191 20.921 -1.001 0.913 7.908 C5 F89 8 F89 C6 C6 C 0 1 Y N N 46.690 36.076 19.988 -2.084 0.843 7.100 C6 F89 9 F89 C6A C6A C 0 1 Y N N 45.718 36.960 20.455 -1.985 0.359 5.779 C6A F89 10 F89 C7 C7 C 0 1 Y N N 44.734 37.412 19.574 -3.111 0.288 4.945 C7 F89 11 F89 C8 C8 C 0 1 Y N N 43.770 38.317 20.014 -2.983 -0.184 3.673 C8 F89 12 F89 C9 C9 C 0 1 Y N N 43.834 38.845 21.312 -1.748 -0.599 3.186 C9 F89 13 F89 C10 C10 C 0 1 Y N N 44.841 38.404 22.201 -0.632 -0.543 3.969 C10 F89 14 F89 C1B C1B C 0 1 Y N N 45.750 37.388 21.814 -0.728 -0.063 5.279 C1B F89 15 F89 C1A C1A C 0 1 Y N N 46.674 36.752 22.705 0.431 0.015 6.157 C1A F89 16 F89 C11 C11 C 0 1 N N N 42.854 39.874 21.718 -1.641 -1.117 1.775 C11 F89 17 F89 N12 N12 N 0 1 N N N 42.669 40.916 20.714 -1.354 -0.004 0.866 N12 F89 18 F89 C13 C13 C 0 1 Y N N 43.552 42.069 20.638 -1.210 -0.238 -0.496 C13 F89 19 F89 C14 C14 C 0 1 Y N N 44.883 41.973 21.079 -0.943 0.820 -1.360 C14 F89 20 F89 C15 C15 C 0 1 Y N N 45.696 43.108 21.037 -0.797 0.586 -2.705 C15 F89 21 F89 C16 C16 C 0 1 Y N N 45.235 44.320 20.542 -0.926 -0.709 -3.216 C16 F89 22 F89 C17 C17 C 0 1 Y N N 43.919 44.438 20.068 -1.199 -1.768 -2.345 C17 F89 23 F89 C18 C18 C 0 1 Y N N 43.080 43.296 20.123 -1.340 -1.531 -0.997 C18 F89 24 F89 C19 C19 C 0 1 N N N 47.071 43.318 21.460 -0.508 1.482 -3.883 C19 F89 25 F89 C C C 0 1 N N N 46.304 45.310 20.650 -0.727 -0.651 -4.674 C F89 26 F89 O O O 0 1 N N N 46.227 46.505 20.318 -0.774 -1.611 -5.419 O F89 27 F89 N N N 0 1 N N N 47.367 44.714 21.211 -0.485 0.611 -5.064 N F89 28 F89 CA CA C 0 1 N N S 48.748 45.182 21.235 -0.240 1.047 -6.441 CA F89 29 F89 CT CT C 0 1 N N N 48.946 46.303 22.275 -1.434 0.708 -7.295 CT F89 30 F89 O1 O1 O 0 1 N N N 49.669 47.273 22.051 -1.709 1.396 -8.250 O1 F89 31 F89 O2 O2 O 0 1 N N N 48.386 46.202 23.362 -2.193 -0.357 -6.996 O2 F89 32 F89 CB CB C 0 1 N N N 49.151 45.624 19.800 0.997 0.333 -6.988 CB F89 33 F89 CG CG C 0 1 N N N 49.181 44.502 18.760 2.209 0.677 -6.121 CG F89 34 F89 CD CD C 0 1 N N N 50.334 43.506 18.820 3.428 -0.025 -6.661 CD F89 35 F89 OE1 OE1 O 0 1 N N N 50.629 42.933 19.867 3.337 -0.728 -7.639 OE1 F89 36 F89 OE2 OE2 O 0 1 N N N 50.910 43.239 17.767 4.616 0.130 -6.055 OE2 F89 37 F89 HN2 HN2 H 0 1 N N N 48.169 36.919 25.644 3.674 -0.540 6.379 HN2 F89 38 F89 H3M1 1H3M H 0 0 N N N 50.574 34.330 24.451 3.324 0.717 9.783 H3M1 F89 39 F89 H3M2 2H3M H 0 0 N N N 50.540 35.952 25.246 4.113 -0.672 9.000 H3M2 F89 40 F89 H3M3 3H3M H 0 0 N N N 49.534 34.696 25.882 4.439 0.978 8.420 H3M3 F89 41 F89 H5 H5 H 0 1 N N N 47.429 34.137 20.666 -1.115 1.289 8.914 H5 F89 42 F89 H6 H6 H 0 1 N N N 47.018 36.076 18.935 -3.045 1.164 7.474 H6 F89 43 F89 H7 H7 H 0 1 N N N 44.718 37.054 18.530 -4.077 0.606 5.310 H7 F89 44 F89 H8 H8 H 0 1 N N N 42.954 38.615 19.333 -3.852 -0.237 3.035 H8 F89 45 F89 H10 H10 H 0 1 N N N 44.918 38.856 23.204 0.320 -0.868 3.579 H10 F89 46 F89 H111 1H11 H 0 0 N N N 41.878 39.407 21.991 -0.837 -1.850 1.717 H111 F89 47 F89 H112 2H11 H 0 0 N N N 43.127 40.316 22.704 -2.582 -1.587 1.488 H112 F89 48 F89 HN12 2HN1 H 0 0 N N N 41.711 41.259 20.792 -1.264 0.895 1.216 HN12 F89 49 F89 H14 H14 H 0 1 N N N 45.285 41.016 21.454 -0.842 1.823 -0.972 H14 F89 50 F89 H17 H17 H 0 1 N N N 43.555 45.398 19.664 -1.300 -2.772 -2.730 H17 F89 51 F89 H18 H18 H 0 1 N N N 42.041 43.363 19.758 -1.551 -2.350 -0.326 H18 F89 52 F89 H191 1H19 H 0 0 N N N 47.261 43.006 22.513 -1.293 2.232 -3.986 H191 F89 53 F89 H192 2H19 H 0 0 N N N 47.793 42.619 20.976 0.459 1.967 -3.757 H192 F89 54 F89 HA HA H 0 1 N N N 49.420 44.351 21.553 -0.075 2.124 -6.457 HA F89 55 F89 HO2 HO2 H 0 1 N N N 48.508 46.892 24.002 -2.959 -0.575 -7.544 HO2 F89 56 F89 HB1 1HB H 0 1 N N N 48.489 46.452 19.453 0.832 -0.743 -6.972 HB1 F89 57 F89 HB2 2HB H 0 1 N N N 50.131 46.153 19.822 1.179 0.657 -8.013 HB2 F89 58 F89 HG1 1HG H 0 1 N N N 48.214 43.946 18.792 2.374 1.755 -6.138 HG1 F89 59 F89 HG2 2HG H 0 1 N N N 49.134 44.947 17.738 2.027 0.353 -5.097 HG2 F89 60 F89 HOE2 2HOE H 0 0 N N N 51.628 42.618 17.804 5.398 -0.320 -6.401 HOE2 F89 61 # # 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 F89 C1 O1A DOUB N N 1 F89 C1 N2 SING Y N 2 F89 C1 C1A SING Y N 3 F89 N2 C3 SING Y N 4 F89 N2 HN2 SING N N 5 F89 C3 C3M SING N N 6 F89 C3 N4 DOUB Y N 7 F89 C3M H3M1 SING N N 8 F89 C3M H3M2 SING N N 9 F89 C3M H3M3 SING N N 10 F89 N4 C4A SING Y N 11 F89 C4A C5 DOUB Y N 12 F89 C4A C1A SING Y N 13 F89 C5 C6 SING Y N 14 F89 C5 H5 SING N N 15 F89 C6 C6A DOUB Y N 16 F89 C6 H6 SING N N 17 F89 C6A C7 SING Y N 18 F89 C6A C1B SING Y N 19 F89 C7 C8 DOUB Y N 20 F89 C7 H7 SING N N 21 F89 C8 C9 SING Y N 22 F89 C8 H8 SING N N 23 F89 C9 C10 DOUB Y N 24 F89 C9 C11 SING N N 25 F89 C10 C1B SING Y N 26 F89 C10 H10 SING N N 27 F89 C1B C1A DOUB Y N 28 F89 C11 N12 SING N N 29 F89 C11 H111 SING N N 30 F89 C11 H112 SING N N 31 F89 N12 C13 SING N N 32 F89 N12 HN12 SING N N 33 F89 C13 C14 DOUB Y N 34 F89 C13 C18 SING Y N 35 F89 C14 C15 SING Y N 36 F89 C14 H14 SING N N 37 F89 C15 C16 DOUB Y N 38 F89 C15 C19 SING N N 39 F89 C16 C17 SING Y N 40 F89 C16 C SING N N 41 F89 C17 C18 DOUB Y N 42 F89 C17 H17 SING N N 43 F89 C18 H18 SING N N 44 F89 C19 N SING N N 45 F89 C19 H191 SING N N 46 F89 C19 H192 SING N N 47 F89 C O DOUB N N 48 F89 C N SING N N 49 F89 N CA SING N N 50 F89 CA CT SING N N 51 F89 CA CB SING N N 52 F89 CA HA SING N N 53 F89 CT O1 DOUB N N 54 F89 CT O2 SING N N 55 F89 O2 HO2 SING N N 56 F89 CB CG SING N N 57 F89 CB HB1 SING N N 58 F89 CB HB2 SING N N 59 F89 CG CD SING N N 60 F89 CG HG1 SING N N 61 F89 CG HG2 SING N N 62 F89 CD OE1 DOUB N N 63 F89 CD OE2 SING N N 64 F89 OE2 HOE2 SING N N 65 # # 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 F89 SMILES ACDLabs 10.04 "O=C(O)C(N5C(=O)c1c(cc(cc1)NCc4cc3c(ccc2N=C(NC(=O)c23)C)cc4)C5)CCC(=O)O" F89 SMILES_CANONICAL CACTVS 3.341 "CC1=Nc2ccc3ccc(CNc4ccc5c(CN([C@@H](CCC(O)=O)C(O)=O)C5=O)c4)cc3c2C(=O)N1" F89 SMILES CACTVS 3.341 "CC1=Nc2ccc3ccc(CNc4ccc5c(CN([CH](CCC(O)=O)C(O)=O)C5=O)c4)cc3c2C(=O)N1" F89 SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 "CC1=Nc2ccc3ccc(cc3c2C(=O)N1)CNc4ccc5c(c4)CN(C5=O)[C@@H](CCC(=O)O)C(=O)O" F89 SMILES "OpenEye OEToolkits" 1.5.0 "CC1=Nc2ccc3ccc(cc3c2C(=O)N1)CNc4ccc5c(c4)CN(C5=O)C(CCC(=O)O)C(=O)O" F89 InChI InChI 1.03 "InChI=1S/C27H24N4O6/c1-14-29-21-7-4-16-3-2-15(10-20(16)24(21)25(34)30-14)12-28-18-5-6-19-17(11-18)13-31(26(19)35)22(27(36)37)8-9-23(32)33/h2-7,10-11,22,28H,8-9,12-13H2,1H3,(H,32,33)(H,36,37)(H,29,30,34)/t22-/m0/s1" F89 InChIKey InChI 1.03 BRVFNEZMTRVUGW-QFIPXVFZSA-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 F89 "SYSTEMATIC NAME" ACDLabs 10.04 "(2S)-2-(5-{[(3-methyl-1-oxo-1,2-dihydrobenzo[f]quinazolin-9-yl)methyl]amino}-1-oxo-1,3-dihydro-2H-isoindol-2-yl)pentanedioic acid" F89 "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "(2S)-2-[6-[(3-methyl-1-oxo-2H-benzo[f]quinazolin-9-yl)methylamino]-3-oxo-1H-isoindol-2-yl]pentanedioic 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 F89 "Create component" 1999-07-08 RCSB F89 "Modify descriptor" 2011-06-04 RCSB F89 "Modify synonyms" 2021-03-01 PDBE # _pdbx_chem_comp_synonyms.ordinal 1 _pdbx_chem_comp_synonyms.comp_id F89 _pdbx_chem_comp_synonyms.name "FOLATE ANALOG 1843U89" _pdbx_chem_comp_synonyms.provenance ? _pdbx_chem_comp_synonyms.type ? ##