data_28Z # _chem_comp.id 28Z _chem_comp.name "N-(4-{[(2-amino-4-oxo-3,4-dihydropteridin-6-yl)methyl]amino}benzoyl)-L-gamma-glutamyl-L-glutamic acid" _chem_comp.type NON-POLYMER _chem_comp.pdbx_type HETAIN _chem_comp.formula "C24 H26 N8 O9" _chem_comp.mon_nstd_parent_comp_id ? _chem_comp.pdbx_synonyms ? _chem_comp.pdbx_formal_charge 0 _chem_comp.pdbx_initial_date 2013-09-11 _chem_comp.pdbx_modified_date 2014-06-13 _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 570.511 _chem_comp.one_letter_code ? _chem_comp.three_letter_code 28Z _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 4MCP _chem_comp.pdbx_subcomponent_list "78H GGL GGL" _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 28Z O4 O4 O 0 1 N N N 29.047 47.531 44.912 9.044 -1.037 -1.504 O4 78H 1 28Z C4 C4 C 0 1 N N N 29.346 48.704 45.546 9.160 0.060 -0.990 C4 78H 2 28Z C4A C4A C 0 1 Y N N 29.068 49.974 45.012 8.138 0.583 -0.066 C5 78H 3 28Z N3 N3 N 0 1 N N N 29.939 48.626 46.751 10.234 0.843 -1.241 N3 78H 4 28Z C8A C8A C 0 1 Y N N 29.417 51.095 45.783 8.341 1.865 0.492 C9 78H 5 28Z N5 N5 N 0 1 Y N N 28.472 50.170 43.803 7.055 -0.116 0.245 N5 78H 6 28Z C2 C2 C 0 1 N N N 30.260 49.725 47.457 10.347 2.069 -0.656 C2 78H 7 28Z N8 N8 N 0 1 Y N N 29.170 52.337 45.339 7.433 2.364 1.332 N8 78H 8 28Z N1 N1 N 0 1 N N N 30.001 50.952 46.981 9.448 2.557 0.163 N1 78H 9 28Z C6 C6 C 0 1 Y N N 28.230 51.432 43.365 6.168 0.393 1.077 C6 78H 10 28Z N2 N2 N 0 1 N N N 30.845 49.593 48.642 11.452 2.829 -0.939 N2 78H 11 28Z C7 C7 C 0 1 Y N N 28.593 52.518 44.161 6.362 1.656 1.630 C7 78H 12 28Z C9 C9 C 0 1 N N N 27.581 51.784 42.010 4.936 -0.398 1.432 C10 78H 13 28Z N10 N10 N 0 1 N N N 26.799 50.702 41.379 3.904 -0.177 0.415 N11 78H 14 28Z CBH CBH C 0 1 Y N N 25.660 50.223 41.918 2.670 -0.806 0.530 C15 78H 15 28Z CAL CAL C 0 1 Y N N 25.072 49.091 41.352 2.414 -1.642 1.613 C16 78H 16 28Z CAK CAK C 0 1 Y N N 25.076 50.835 43.029 1.690 -0.595 -0.437 C17 78H 17 28Z CAN CAN C 0 1 Y N N 23.906 48.573 41.932 1.193 -2.267 1.729 C18 78H 18 28Z CAM CAM C 0 1 Y N N 23.925 50.340 43.607 0.467 -1.217 -0.327 C19 78H 19 28Z CBI CBI C 0 1 Y N N 23.340 49.200 43.044 0.210 -2.062 0.757 C20 78H 20 28Z CBF CBF C 0 1 N N N 22.087 48.691 43.699 -1.100 -2.731 0.877 C21 78H 21 28Z OAF OAF O 0 1 N N N 21.574 49.330 44.615 -1.324 -3.462 1.823 O22 78H 22 28Z NBA NBA N 0 1 N N N 21.620 47.500 43.312 -2.047 -2.532 -0.061 N GGL 23 28Z CBO CBO C 0 1 N N S 20.372 47.020 43.949 -3.347 -3.196 0.059 CA GGL 24 28Z CBD CBD C 0 1 N N N 20.608 46.725 45.400 -3.260 -4.581 -0.530 C GGL 25 28Z OAI OAI O 0 1 N N N 21.663 46.105 45.722 -2.219 -4.972 -1.001 O GGL 26 28Z CAS CAS C 0 1 N N N 19.882 45.728 43.257 -4.405 -2.387 -0.695 CB GGL 27 28Z CAQ CAQ C 0 1 N N N 18.686 45.085 43.960 -4.582 -1.025 -0.020 CG GGL 28 28Z CBE CBE C 0 1 N N N 17.897 44.398 42.847 -5.623 -0.228 -0.763 CD GGL 29 28Z OAE OAE O 0 1 N N N 18.305 43.354 42.329 -6.170 -0.703 -1.736 OE1 GGL 30 28Z OAD OAD O 0 1 N N N 19.719 47.161 46.150 -4.339 -5.379 -0.530 OXT GGL 31 28Z N N N 0 1 N N N 16.747 44.957 42.464 -5.948 1.011 -0.345 N GGL 32 28Z CA CA C 0 1 N N S 16.058 44.389 41.292 -6.960 1.786 -1.067 CA GGL 33 28Z C C C 0 1 N N N 17.015 44.523 40.075 -6.313 2.501 -2.225 C GGL 34 28Z OXT OXT O 0 1 N N N 16.865 43.687 39.147 -5.129 2.377 -2.427 O GGL 35 28Z CB CB C 0 1 N N N 14.748 45.169 41.009 -7.588 2.811 -0.121 CB GGL 36 28Z CG CG C 0 1 N N N 15.046 46.649 40.727 -8.350 2.082 0.988 CG GGL 37 28Z CD CD C 0 1 N N N 13.826 47.429 40.186 -8.969 3.092 1.919 CD GGL 38 28Z OE1 OE1 O 0 1 N N N 12.985 46.840 39.464 -8.816 4.273 1.718 OE1 GGL 39 28Z OE2 OE2 O 0 1 N N N 13.771 48.647 40.472 -9.690 2.679 2.974 OE2 GGL 40 28Z O O O 0 1 N N N 17.895 45.437 40.089 -7.054 3.277 -3.033 OXT GGL 41 28Z H4 H4 H 0 1 N N N 30.147 47.725 47.133 10.929 0.530 -1.842 H3 78H 42 28Z H2 H2 H 0 1 N N N 31.089 50.405 49.172 12.132 2.490 -1.543 H21N 78H 43 28Z H3 H3 H 0 1 N N N 31.041 48.682 49.004 11.555 3.705 -0.535 H22N 78H 44 28Z H1 H1 H 0 1 N N N 28.401 53.522 43.811 5.626 2.059 2.309 H71 78H 45 28Z H5 H5 H 0 1 N N N 28.383 52.072 41.315 5.184 -1.458 1.473 H101 78H 46 28Z H6 H6 H 0 1 N N N 26.908 52.640 42.169 4.564 -0.074 2.404 H102 78H 47 28Z H7 H7 H 0 1 N N N 27.419 49.921 41.300 4.082 0.409 -0.337 H11 78H 48 28Z H10 H10 H 0 1 N N N 25.508 48.622 40.482 3.174 -1.800 2.364 H16 78H 49 28Z H8 H8 H 0 1 N N N 25.537 51.718 43.446 1.890 0.057 -1.274 H17 78H 50 28Z H11 H11 H 0 1 N N N 23.445 47.688 41.519 0.996 -2.916 2.569 H18 78H 51 28Z H9 H9 H 0 1 N N N 23.487 50.819 44.470 -0.292 -1.053 -1.077 H19 78H 52 28Z H12 H12 H 0 1 N N N 22.094 46.955 42.620 -1.868 -1.949 -0.815 H GGL 53 28Z H13 H13 H 0 1 N N N 19.591 47.789 43.856 -3.624 -3.265 1.111 HA GGL 54 28Z H15 H15 H 0 1 N N N 19.591 45.973 42.225 -4.084 -2.242 -1.727 HB2 GGL 55 28Z H16 H16 H 0 1 N N N 20.710 45.004 43.242 -5.352 -2.925 -0.681 HB3 GGL 56 28Z H17 H17 H 0 1 N N N 18.070 45.851 44.455 -4.903 -1.170 1.012 HG2 GGL 57 28Z H18 H18 H 0 1 N N N 19.025 44.350 44.705 -3.634 -0.487 -0.034 HG3 GGL 58 28Z H14 H14 H 0 1 N N N 19.939 46.961 47.052 -4.235 -6.258 -0.919 HXT GGL 59 28Z H19 H19 H 0 1 N N N 16.364 45.738 42.958 -5.510 1.391 0.433 H GGL 60 28Z H20 H20 H 0 1 N N N 15.824 43.327 41.459 -7.733 1.115 -1.440 HA GGL 61 28Z H22 H22 H 0 1 N N N 14.087 45.095 41.885 -6.804 3.426 0.321 HB2 GGL 62 28Z H23 H23 H 0 1 N N N 14.248 44.729 40.134 -8.277 3.446 -0.678 HB3 GGL 63 28Z H24 H24 H 0 1 N N N 15.854 46.706 39.983 -9.134 1.468 0.545 HG2 GGL 64 28Z H25 H25 H 0 1 N N N 15.375 47.123 41.663 -7.662 1.447 1.545 HG3 GGL 65 28Z H26 H26 H 0 1 N N N 13.007 49.035 40.061 -10.067 3.364 3.543 HE2 GGL 66 28Z H21 H21 H 0 1 N N N 18.415 45.388 39.296 -6.595 3.715 -3.762 HXT GGL 67 # 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 28Z OXT C DOUB N N 1 28Z OE1 CD DOUB N N 2 28Z C O SING N N 3 28Z C CA SING N N 4 28Z CD OE2 SING N N 5 28Z CD CG SING N N 6 28Z CG CB SING N N 7 28Z CB CA SING N N 8 28Z CA N SING N N 9 28Z CAL CBH DOUB Y N 10 28Z CAL CAN SING Y N 11 28Z N10 CBH SING N N 12 28Z N10 C9 SING N N 13 28Z CBH CAK SING Y N 14 28Z CAN CBI DOUB Y N 15 28Z C9 C6 SING N N 16 28Z OAE CBE DOUB N N 17 28Z N CBE SING N N 18 28Z CBE CAQ SING N N 19 28Z CAK CAM DOUB Y N 20 28Z CBI CAM SING Y N 21 28Z CBI CBF SING N N 22 28Z CAS CBO SING N N 23 28Z CAS CAQ SING N N 24 28Z NBA CBF SING N N 25 28Z NBA CBO SING N N 26 28Z C6 N5 DOUB Y N 27 28Z C6 C7 SING Y N 28 28Z CBF OAF DOUB N N 29 28Z N5 C4A SING Y N 30 28Z CBO CBD SING N N 31 28Z C7 N8 DOUB Y N 32 28Z O4 C4 DOUB N N 33 28Z C4A C4 SING N N 34 28Z C4A C8A DOUB Y N 35 28Z N8 C8A SING Y N 36 28Z CBD OAI DOUB N N 37 28Z CBD OAD SING N N 38 28Z C4 N3 SING N N 39 28Z C8A N1 SING N N 40 28Z N3 C2 SING N N 41 28Z N1 C2 DOUB N N 42 28Z C2 N2 SING N N 43 28Z C7 H1 SING N N 44 28Z N2 H2 SING N N 45 28Z N2 H3 SING N N 46 28Z N3 H4 SING N N 47 28Z C9 H5 SING N N 48 28Z C9 H6 SING N N 49 28Z N10 H7 SING N N 50 28Z CAK H8 SING N N 51 28Z CAM H9 SING N N 52 28Z CAL H10 SING N N 53 28Z CAN H11 SING N N 54 28Z NBA H12 SING N N 55 28Z CBO H13 SING N N 56 28Z OAD H14 SING N N 57 28Z CAS H15 SING N N 58 28Z CAS H16 SING N N 59 28Z CAQ H17 SING N N 60 28Z CAQ H18 SING N N 61 28Z N H19 SING N N 62 28Z CA H20 SING N N 63 28Z O H21 SING N N 64 28Z CB H22 SING N N 65 28Z CB H23 SING N N 66 28Z CG H24 SING N N 67 28Z CG H25 SING N N 68 28Z OE2 H26 SING N N 69 # 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 28Z SMILES ACDLabs 12.01 "O=C(O)C(NC(=O)CCC(C(=O)O)NC(=O)c1ccc(cc1)NCc3nc2c(N=C(N)NC2=O)nc3)CCC(=O)O" 28Z InChI InChI 1.03 "InChI=1S/C24H26N8O9/c25-24-31-19-18(21(37)32-24)28-13(10-27-19)9-26-12-3-1-11(2-4-12)20(36)30-15(23(40)41)5-7-16(33)29-14(22(38)39)6-8-17(34)35/h1-4,10,14-15,26H,5-9H2,(H,29,33)(H,30,36)(H,34,35)(H,38,39)(H,40,41)(H3,25,27,31,32,37)/t14-,15-/m0/s1" 28Z InChIKey InChI 1.03 SDUHYPXROSSGGK-GJZGRUSLSA-N 28Z SMILES_CANONICAL CACTVS 3.385 "NC1=Nc2ncc(CNc3ccc(cc3)C(=O)N[C@@H](CCC(=O)N[C@@H](CCC(O)=O)C(O)=O)C(O)=O)nc2C(=O)N1" 28Z SMILES CACTVS 3.385 "NC1=Nc2ncc(CNc3ccc(cc3)C(=O)N[CH](CCC(=O)N[CH](CCC(O)=O)C(O)=O)C(O)=O)nc2C(=O)N1" 28Z SMILES_CANONICAL "OpenEye OEToolkits" 1.7.6 "c1cc(ccc1C(=O)N[C@@H](CCC(=O)N[C@@H](CCC(=O)O)C(=O)O)C(=O)O)NCc2cnc3c(n2)C(=O)NC(=N3)N" 28Z SMILES "OpenEye OEToolkits" 1.7.6 "c1cc(ccc1C(=O)NC(CCC(=O)NC(CCC(=O)O)C(=O)O)C(=O)O)NCc2cnc3c(n2)C(=O)NC(=N3)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 28Z "SYSTEMATIC NAME" ACDLabs 12.01 "N-(4-{[(2-amino-4-oxo-3,4-dihydropteridin-6-yl)methyl]amino}benzoyl)-L-gamma-glutamyl-L-glutamic acid" 28Z "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.7.6 "(2S)-2-[[(4S)-4-[[4-[(2-azanyl-4-oxidanylidene-3H-pteridin-6-yl)methylamino]phenyl]carbonylamino]-5-oxidanyl-5-oxidanylidene-pentanoyl]amino]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 28Z "Create component" 2013-09-11 RCSB 28Z "Initial release" 2014-06-18 RCSB #