data_4DW # _chem_comp.id 4DW _chem_comp.name "N-{4-[2-(2-amino-4-oxo-4,7-dihydro-3H-pyrrolo[2,3-d]pyrimidin-5-yl)ethyl]benzoyl}-L-glutamic acid" _chem_comp.type NON-POLYMER _chem_comp.pdbx_type HETAIN _chem_comp.formula "C20 H19 N5 O6" _chem_comp.mon_nstd_parent_comp_id ? _chem_comp.pdbx_synonyms pemetrexed _chem_comp.pdbx_formal_charge 0 _chem_comp.pdbx_initial_date 2015-03-05 _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 425.395 _chem_comp.one_letter_code ? _chem_comp.three_letter_code 4DW _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 4ZZ3 _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 4DW C1 C1 C 0 1 Y N N 62.197 48.207 18.685 0.971 0.369 0.381 C1 4DW 1 4DW C2 C2 C 0 1 Y N N 61.011 48.911 18.852 0.681 -0.873 0.917 C2 4DW 2 4DW C3 C3 C 0 1 Y N N 59.867 48.533 18.159 -0.617 -1.339 0.923 C3 4DW 3 4DW C4 C4 C 0 1 Y N N 59.937 47.444 17.300 -1.639 -0.555 0.386 C4 4DW 4 4DW C5 C5 C 0 1 Y N N 61.117 46.732 17.124 -1.340 0.697 -0.154 C5 4DW 5 4DW C6 C6 C 0 1 Y N N 62.257 47.119 17.821 -0.038 1.153 -0.149 C6 4DW 6 4DW C7 C7 C 0 1 N N N 63.407 48.670 19.468 2.392 0.872 0.378 C7 4DW 7 4DW C8 C8 C 0 1 N N N 63.408 48.563 20.979 3.086 0.434 -0.913 C8 4DW 8 4DW C9 C9 C 0 1 Y N N 62.313 47.679 21.540 4.506 0.937 -0.916 C9 4DW 9 4DW C10 C10 C 0 1 Y N N 62.141 46.327 21.280 4.956 2.074 -1.475 C10 4DW 10 4DW N11 N1 N 0 1 Y N N 61.062 45.918 21.963 6.307 2.181 -1.265 N11 4DW 11 4DW C12 C11 C 0 1 Y N N 60.540 46.945 22.648 6.757 1.110 -0.564 C12 4DW 12 4DW C13 C12 C 0 1 Y N N 61.302 48.075 22.406 5.663 0.288 -0.306 C13 4DW 13 4DW C14 C13 C 0 1 N N N 60.945 49.267 23.019 5.877 -0.946 0.451 C14 4DW 14 4DW O15 O1 O 0 1 N N N 61.594 50.283 22.829 4.947 -1.697 0.697 O15 4DW 15 4DW N16 N2 N 0 1 N N N 59.875 49.302 23.825 7.121 -1.233 0.870 N16 4DW 16 4DW C17 C14 C 0 1 N N N 59.152 48.192 24.043 8.130 -0.429 0.610 C17 4DW 17 4DW N18 N3 N 0 1 N N N 59.480 47.027 23.462 7.990 0.723 -0.095 N18 4DW 18 4DW N19 N4 N 0 1 N N N 58.021 48.233 24.898 9.375 -0.774 1.062 N19 4DW 19 4DW C20 C15 C 0 1 N N N 58.653 47.050 16.549 -3.033 -1.048 0.388 C20 4DW 20 4DW O21 O2 O 0 1 N N N 57.669 47.754 16.649 -3.291 -2.139 0.859 O21 4DW 21 4DW N22 N5 N 0 1 N N N 58.662 45.870 15.762 -4.018 -0.288 -0.131 N22 4DW 22 4DW C23 C16 C 0 1 N N S 57.470 45.512 15.080 -5.399 -0.777 -0.129 C23 4DW 23 4DW C24 C17 C 0 1 N N N 57.744 44.900 13.722 -6.346 0.394 -0.165 C24 4DW 24 4DW C25 C18 C 0 1 N N N 59.023 44.109 13.568 -7.151 0.631 0.868 C25 4DW 25 4DW C26 C19 C 0 1 N N N 59.136 43.158 12.396 -8.075 1.774 0.833 C26 4DW 26 4DW O27 O3 O 0 1 N N N 58.200 43.085 11.558 -8.104 2.502 -0.140 O27 4DW 27 4DW O28 O4 O 0 1 N N N 60.164 42.443 12.264 -8.890 2.014 1.880 O28 4DW 28 4DW C29 C20 C 0 1 N N N 56.781 44.482 15.950 -5.627 -1.645 -1.340 C29 4DW 29 4DW O30 O5 O 0 1 N N N 56.246 44.872 17.022 -6.828 -2.206 -1.547 O30 4DW 30 4DW O31 O6 O 0 1 N N N 56.748 43.271 15.607 -4.727 -1.835 -2.124 O31 4DW 31 4DW H1 H1 H 0 1 N N N 60.978 49.756 19.524 1.473 -1.479 1.332 H1 4DW 32 4DW H2 H2 H 0 1 N N N 58.942 49.076 18.286 -0.842 -2.309 1.342 H2 4DW 33 4DW H3 H3 H 0 1 N N N 61.149 45.887 16.453 -2.126 1.309 -0.571 H3 4DW 34 4DW H4 H4 H 0 1 N N N 63.183 46.578 17.692 0.195 2.122 -0.566 H4 4DW 35 4DW H5 H5 H 0 1 N N N 64.265 48.084 19.106 2.392 1.960 0.440 H5 4DW 36 4DW H6 H6 H 0 1 N N N 63.559 49.732 19.223 2.925 0.458 1.235 H6 4DW 37 4DW H7 H7 H 0 1 N N N 64.378 48.153 21.295 3.085 -0.654 -0.975 H7 4DW 38 4DW H8 H8 H 0 1 N N N 63.284 49.573 21.396 2.553 0.847 -1.770 H8 4DW 39 4DW H9 H9 H 0 1 N N N 62.763 45.715 20.643 4.348 2.791 -2.007 H9 4DW 40 4DW H10 H10 H 0 1 N N N 60.701 44.986 21.962 6.861 2.915 -1.574 H10 4DW 41 4DW H11 H11 H 0 1 N N N 58.927 46.213 23.639 8.764 1.283 -0.260 H11 4DW 42 4DW H12 H12 H 0 1 N N N 57.760 49.091 25.341 9.500 -1.595 1.562 H12 4DW 43 4DW H13 H13 H 0 1 N N N 57.485 47.404 25.058 10.134 -0.196 0.882 H13 4DW 44 4DW H14 H14 H 0 1 N N N 59.485 45.306 15.690 -3.812 0.582 -0.507 H14 4DW 45 4DW H15 H15 H 0 1 N N N 56.813 46.386 14.960 -5.576 -1.360 0.775 H15 4DW 46 4DW H16 H16 H 0 1 N N N 57.055 45.023 12.899 -6.372 1.041 -1.029 H16 4DW 47 4DW H17 H17 H 0 1 N N N 59.833 44.219 14.274 -7.125 -0.016 1.733 H17 4DW 48 4DW H18 H18 H 0 1 N N N 60.079 41.906 11.485 -9.480 2.777 1.811 H18 4DW 49 4DW H19 H19 H 0 1 N N N 55.853 44.131 17.468 -6.926 -2.754 -2.337 H19 4DW 50 # # 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 4DW O27 C26 DOUB N N 1 4DW O28 C26 SING N N 2 4DW C26 C25 SING N N 3 4DW C25 C24 DOUB N E 4 4DW C24 C23 SING N N 5 4DW C23 N22 SING N N 6 4DW C23 C29 SING N N 7 4DW O31 C29 DOUB N N 8 4DW N22 C20 SING N N 9 4DW C29 O30 SING N N 10 4DW C20 O21 DOUB N N 11 4DW C20 C4 SING N N 12 4DW C5 C4 DOUB Y N 13 4DW C5 C6 SING Y N 14 4DW C4 C3 SING Y N 15 4DW C6 C1 DOUB Y N 16 4DW C3 C2 DOUB Y N 17 4DW C1 C2 SING Y N 18 4DW C1 C7 SING N N 19 4DW C7 C8 SING N N 20 4DW C8 C9 SING N N 21 4DW C10 C9 DOUB Y N 22 4DW C10 N11 SING Y N 23 4DW C9 C13 SING Y N 24 4DW N11 C12 SING Y N 25 4DW C13 C12 DOUB Y N 26 4DW C13 C14 SING N N 27 4DW C12 N18 SING N N 28 4DW O15 C14 DOUB N N 29 4DW C14 N16 SING N N 30 4DW N18 C17 SING N N 31 4DW N16 C17 DOUB N N 32 4DW C17 N19 SING N N 33 4DW C2 H1 SING N N 34 4DW C3 H2 SING N N 35 4DW C5 H3 SING N N 36 4DW C6 H4 SING N N 37 4DW C7 H5 SING N N 38 4DW C7 H6 SING N N 39 4DW C8 H7 SING N N 40 4DW C8 H8 SING N N 41 4DW C10 H9 SING N N 42 4DW N11 H10 SING N N 43 4DW N18 H11 SING N N 44 4DW N19 H12 SING N N 45 4DW N19 H13 SING N N 46 4DW N22 H14 SING N N 47 4DW C23 H15 SING N N 48 4DW C24 H16 SING N N 49 4DW C25 H17 SING N N 50 4DW O28 H18 SING N N 51 4DW O30 H19 SING N N 52 # # 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 4DW SMILES ACDLabs 12.01 "c1(ccc(cc1)C(=O)NC(C(O)=O)[C@H]=[C@H]C(=O)O)CCc2c3c(nc2)NC(=NC3=O)N" 4DW InChI InChI 1.03 "InChI=1S/C20H19N5O6/c21-20-24-16-15(18(29)25-20)12(9-22-16)6-3-10-1-4-11(5-2-10)17(28)23-13(19(30)31)7-8-14(26)27/h1-2,4-5,7-9,13H,3,6H2,(H,23,28)(H,26,27)(H,30,31)(H4,21,22,24,25,29)/b8-7+/t13-/m0/s1" 4DW InChIKey InChI 1.03 OOPGILDDKAKTLT-GWJCSSMESA-N 4DW SMILES_CANONICAL CACTVS 3.385 "NC1=NC(=O)c2c(CCc3ccc(cc3)C(=O)N[C@@H](/C=C/C(O)=O)C(O)=O)c[nH]c2N1" 4DW SMILES CACTVS 3.385 "NC1=NC(=O)c2c(CCc3ccc(cc3)C(=O)N[CH](C=CC(O)=O)C(O)=O)c[nH]c2N1" 4DW SMILES_CANONICAL "OpenEye OEToolkits" 1.9.2 "c1cc(ccc1CCc2c[nH]c3c2C(=O)N=C(N3)N)C(=O)N[C@@H](/C=C/C(=O)O)C(=O)O" 4DW SMILES "OpenEye OEToolkits" 1.9.2 "c1cc(ccc1CCc2c[nH]c3c2C(=O)N=C(N3)N)C(=O)NC(C=CC(=O)O)C(=O)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 4DW "SYSTEMATIC NAME" ACDLabs 12.01 "(2E,4S)-4-({4-[2-(2-amino-4-oxo-4,7-dihydro-1H-pyrrolo[2,3-d]pyrimidin-5-yl)ethyl]benzoyl}amino)pent-2-enedioic acid" 4DW "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.9.2 "(E,4S)-4-[[4-[2-(2-azanyl-4-oxidanylidene-1,7-dihydropyrrolo[2,3-d]pyrimidin-5-yl)ethyl]phenyl]carbonylamino]pent-2-enedioic 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 4DW "Create component" 2015-03-05 RCSB 4DW "Modify synonyms" 2015-06-10 RCSB 4DW "Initial release" 2015-12-16 RCSB 4DW "Modify synonyms" 2021-03-01 PDBE # _pdbx_chem_comp_synonyms.ordinal 1 _pdbx_chem_comp_synonyms.comp_id 4DW _pdbx_chem_comp_synonyms.name pemetrexed _pdbx_chem_comp_synonyms.provenance ? _pdbx_chem_comp_synonyms.type ? ##