data_MEF # _chem_comp.id MEF _chem_comp.name "N-({4-[(6aR)-3-amino-1-oxo-1,2,5,6,6a,7-hexahydroimidazo[1,5-f]pteridin-8(9H)-yl]phenyl}carbonyl)-L-glutamic acid" _chem_comp.type NON-POLYMER _chem_comp.pdbx_type HETAIN _chem_comp.formula "C20 H23 N7 O6" _chem_comp.mon_nstd_parent_comp_id ? _chem_comp.pdbx_synonyms "5,10-methylene,5,6,7,8-tetrahydrofolate" _chem_comp.pdbx_formal_charge 0 _chem_comp.pdbx_initial_date 2007-12-05 _chem_comp.pdbx_modified_date 2021-03-13 _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 457.440 _chem_comp.one_letter_code ? _chem_comp.three_letter_code MEF _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 3BHR _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 MEF OE2 OE2 O 0 1 N N N 43.954 27.620 44.485 -7.883 2.701 0.413 OE2 MEF 1 MEF CD CD C 0 1 N N N 44.679 26.884 45.155 -7.386 2.066 1.313 CD MEF 2 MEF OE1 OE1 O 0 1 N N N 44.297 26.670 46.415 -7.594 2.432 2.588 OE1 MEF 3 MEF CG CG C 0 1 N N N 45.943 26.224 44.597 -6.537 0.860 1.004 CG MEF 4 MEF CB CB C 0 1 N N N 46.185 26.548 43.107 -6.467 0.660 -0.512 CB MEF 5 MEF CA CA C 0 1 N N S 46.858 25.403 42.317 -5.606 -0.564 -0.826 CA MEF 6 MEF CT CT C 0 1 N N N 48.252 25.052 42.782 -5.636 -0.833 -2.308 CT MEF 7 MEF O1 O1 O 0 1 N N N 48.582 23.895 43.404 -6.803 -1.092 -2.919 O1 MEF 8 MEF O2 O2 O 0 1 N N N 49.102 25.901 42.551 -4.610 -0.816 -2.947 O2 MEF 9 MEF N N N 0 1 N N N 46.018 24.226 42.338 -4.226 -0.312 -0.403 N MEF 10 MEF C C C 0 1 N N N 45.060 24.072 41.422 -3.414 -1.344 -0.102 C MEF 11 MEF O O O 0 1 N N N 44.805 24.921 40.578 -3.826 -2.486 -0.180 O MEF 12 MEF N10 N10 N 0 1 N N N 42.049 19.134 41.518 1.896 -0.373 1.522 N10 MEF 13 MEF CM CM C 0 1 N N N 42.690 18.256 40.509 2.654 0.347 0.466 CM MEF 14 MEF N5 N5 N 0 1 N N N 41.987 18.713 39.268 4.056 -0.028 0.631 N5 MEF 15 MEF C9 C9 C 0 1 N N N 40.595 19.223 41.142 2.650 -1.652 1.678 C9 MEF 16 MEF C6 C6 C 0 1 N N R 40.554 18.803 39.686 4.112 -1.189 1.554 C6 MEF 17 MEF C7 C7 C 0 1 N N N 39.883 19.769 38.782 4.976 -2.245 0.857 C7 MEF 18 MEF N8 N8 N 0 1 N N N 40.259 19.391 37.387 6.266 -1.627 0.510 N8 MEF 19 MEF C8A C8A C 0 1 N N N 41.562 19.295 37.037 6.325 -0.359 -0.043 C8A MEF 20 MEF C4A C4A C 0 1 N N N 42.481 18.936 38.016 5.211 0.479 0.015 C4A MEF 21 MEF N1 N1 N 0 1 N N N 41.949 19.556 35.766 7.440 0.082 -0.636 N1 MEF 22 MEF C2 C2 C 0 1 N N N 43.250 19.451 35.440 7.502 1.291 -1.152 C2 MEF 23 MEF NA2 NA2 N 0 1 N N N 43.612 19.698 34.180 8.667 1.701 -1.749 NA2 MEF 24 MEF N3 N3 N 0 1 N N N 44.182 19.107 36.354 6.444 2.145 -1.111 N3 MEF 25 MEF C4 C4 C 0 1 N N N 43.837 18.842 37.629 5.284 1.758 -0.532 C4 MEF 26 MEF O4 O4 O 0 1 N N N 44.728 18.519 38.444 4.323 2.512 -0.491 O4 MEF 27 MEF C11 C11 C 0 1 Y N N 44.281 22.790 41.428 -2.024 -1.090 0.323 C11 MEF 28 MEF C12 C12 C 0 1 Y N N 44.810 21.632 42.017 -1.181 -2.160 0.636 C12 MEF 29 MEF C13 C13 C 0 1 Y N N 44.069 20.469 42.033 0.115 -1.920 1.032 C13 MEF 30 MEF C16 C16 C 0 1 Y N N 43.021 22.772 40.837 -1.546 0.221 0.408 C16 MEF 31 MEF C15 C15 C 0 1 Y N N 42.282 21.604 40.853 -0.249 0.454 0.805 C15 MEF 32 MEF C14 C14 C 0 1 Y N N 42.796 20.449 41.465 0.587 -0.613 1.121 C14 MEF 33 MEF HOE1 HOE1 H 0 0 N N N 43.493 27.145 46.587 -8.148 3.210 2.736 HOE1 MEF 34 MEF HG HG H 0 1 N N N 46.806 26.587 45.174 -5.532 1.012 1.397 HG MEF 35 MEF HGA HGA H 0 1 N N N 45.813 25.135 44.682 -6.979 -0.023 1.466 HGA MEF 36 MEF HB HB H 0 1 N N N 45.210 26.755 42.641 -7.472 0.508 -0.905 HB MEF 37 MEF HBA HBA H 0 1 N N N 46.870 27.408 43.072 -6.026 1.543 -0.974 HBA MEF 38 MEF HA HA H 0 1 N N N 46.973 25.779 41.290 -5.996 -1.430 -0.291 HA MEF 39 MEF HO1 HO1 H 0 1 N N N 49.512 23.893 43.597 -6.772 -1.258 -3.872 HO1 MEF 40 MEF HN HN H 0 1 N N N 46.155 23.527 43.040 -3.896 0.598 -0.341 HN MEF 41 MEF HM HM H 0 1 N N N 43.779 18.399 40.455 2.300 0.045 -0.520 HM MEF 42 MEF HMA HMA H 0 1 N N N 42.597 17.180 40.716 2.536 1.424 0.590 HMA MEF 43 MEF H9 H9 H 0 1 N N N 39.982 18.556 41.765 2.465 -2.094 2.657 H9 MEF 44 MEF H9A H9A H 0 1 N N N 40.186 20.232 41.296 2.394 -2.352 0.883 H9A MEF 45 MEF H6 H6 H 0 1 N N N 39.980 17.868 39.609 4.520 -0.905 2.524 H6 MEF 46 MEF H7 H7 H 0 1 N N N 38.792 19.719 38.911 5.141 -3.087 1.529 H7 MEF 47 MEF H7A H7A H 0 1 N N N 40.195 20.799 39.007 4.477 -2.589 -0.049 H7A MEF 48 MEF HN8 HN8 H 0 1 N N N 39.863 18.486 37.229 7.088 -2.115 0.672 HN8 MEF 49 MEF HNA2 HNA2 H 0 0 N N N 44.600 19.584 34.078 9.430 1.103 -1.786 HNA2 MEF 50 MEF HNAA HNAA H 0 0 N N N 42.986 19.959 33.445 8.728 2.589 -2.134 HNAA MEF 51 MEF HN3 HN3 H 0 1 N N N 45.142 19.048 36.081 6.521 3.032 -1.496 HN3 MEF 52 MEF H12 H12 H 0 1 N N N 45.796 21.651 42.457 -1.546 -3.174 0.568 H12 MEF 53 MEF H13 H13 H 0 1 N N N 44.474 19.576 42.485 0.767 -2.746 1.274 H13 MEF 54 MEF H16 H16 H 0 1 N N N 42.625 23.662 40.371 -2.194 1.049 0.163 H16 MEF 55 MEF H15 H15 H 0 1 N N N 41.305 21.579 40.393 0.120 1.467 0.871 H15 MEF 56 # # 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 MEF OE2 CD DOUB N N 1 MEF CG CD SING N N 2 MEF CD OE1 SING N N 3 MEF OE1 HOE1 SING N N 4 MEF CB CG SING N N 5 MEF CG HG SING N N 6 MEF CG HGA SING N N 7 MEF CA CB SING N N 8 MEF CB HB SING N N 9 MEF CB HBA SING N N 10 MEF CA N SING N N 11 MEF CA CT SING N N 12 MEF CA HA SING N N 13 MEF O2 CT DOUB N N 14 MEF CT O1 SING N N 15 MEF O1 HO1 SING N N 16 MEF C N SING N N 17 MEF N HN SING N N 18 MEF O C DOUB N N 19 MEF C C11 SING N N 20 MEF CM N10 SING N N 21 MEF C9 N10 SING N N 22 MEF C14 N10 SING N N 23 MEF N5 CM SING N N 24 MEF CM HM SING N N 25 MEF CM HMA SING N N 26 MEF C4A N5 SING N N 27 MEF N5 C6 SING N N 28 MEF C6 C9 SING N N 29 MEF C9 H9 SING N N 30 MEF C9 H9A SING N N 31 MEF C7 C6 SING N N 32 MEF C6 H6 SING N N 33 MEF N8 C7 SING N N 34 MEF C7 H7 SING N N 35 MEF C7 H7A SING N N 36 MEF C8A N8 SING N N 37 MEF N8 HN8 SING N N 38 MEF N1 C8A SING N N 39 MEF C8A C4A DOUB N N 40 MEF C4 C4A SING N N 41 MEF C2 N1 DOUB N N 42 MEF NA2 C2 SING N N 43 MEF C2 N3 SING N N 44 MEF NA2 HNA2 SING N N 45 MEF NA2 HNAA SING N N 46 MEF N3 C4 SING N N 47 MEF N3 HN3 SING N N 48 MEF C4 O4 DOUB N N 49 MEF C16 C11 DOUB Y N 50 MEF C11 C12 SING Y N 51 MEF C12 C13 DOUB Y N 52 MEF C12 H12 SING N N 53 MEF C14 C13 SING Y N 54 MEF C13 H13 SING N N 55 MEF C16 C15 SING Y N 56 MEF C16 H16 SING N N 57 MEF C15 C14 DOUB Y N 58 MEF C15 H15 SING N N 59 # # 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 MEF SMILES ACDLabs 10.04 "O=C(O)C(NC(=O)c1ccc(cc1)N4CC3N(C=2C(=O)NC(=NC=2NC3)N)C4)CCC(=O)O" MEF SMILES_CANONICAL CACTVS 3.341 "NC1=NC2=C(N3CN(C[C@H]3CN2)c4ccc(cc4)C(=O)N[C@@H](CCC(O)=O)C(O)=O)C(=O)N1" MEF SMILES CACTVS 3.341 "NC1=NC2=C(N3CN(C[CH]3CN2)c4ccc(cc4)C(=O)N[CH](CCC(O)=O)C(O)=O)C(=O)N1" MEF SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 "c1cc(ccc1C(=O)N[C@@H](CCC(=O)O)C(=O)O)[N@]2C[C@H]3CNC4=C(N3C2)C(=O)NC(=N4)N" MEF SMILES "OpenEye OEToolkits" 1.5.0 "c1cc(ccc1C(=O)NC(CCC(=O)O)C(=O)O)N2CC3CNC4=C(N3C2)C(=O)NC(=N4)N" MEF InChI InChI 1.03 "InChI=1S/C20H23N7O6/c21-20-24-16-15(18(31)25-20)27-9-26(8-12(27)7-22-16)11-3-1-10(2-4-11)17(30)23-13(19(32)33)5-6-14(28)29/h1-4,12-13H,5-9H2,(H,23,30)(H,28,29)(H,32,33)(H4,21,22,24,25,31)/t12-,13+/m1/s1" MEF InChIKey InChI 1.03 QYNUQALWYRSVHF-OLZOCXBDSA-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 MEF "SYSTEMATIC NAME" ACDLabs 10.04 "N-({4-[(6aR)-3-amino-1-oxo-1,2,5,6,6a,7-hexahydroimidazo[1,5-f]pteridin-8(9H)-yl]phenyl}carbonyl)-L-glutamic acid" MEF "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "(2S)-2-[[4-[(6aR,8R)-3-amino-1-oxo-2,5,6,6a,7,9-hexahydroimidazo[3,4-f]pteridin-8-yl]phenyl]carbonylamino]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 MEF "Create component" 2007-12-05 RCSB MEF "Modify aromatic_flag" 2011-06-04 RCSB MEF "Modify descriptor" 2011-06-04 RCSB MEF "Modify synonyms" 2021-03-13 RCSB # _pdbx_chem_comp_synonyms.ordinal 1 _pdbx_chem_comp_synonyms.comp_id MEF _pdbx_chem_comp_synonyms.name "5,10-methylene,5,6,7,8-tetrahydrofolate" _pdbx_chem_comp_synonyms.provenance PDB _pdbx_chem_comp_synonyms.type ? ##