data_83A # _chem_comp.id 83A _chem_comp.name "N-(4-{[2-(2-amino-4-oxo-4,7-dihydro-3H-pyrrolo[2,3-d]pyrimidin-6-yl)ethyl]amino}benzene-1-carbonyl)-L-glutamic acid" _chem_comp.type NON-POLYMER _chem_comp.pdbx_type HETAIN _chem_comp.formula "C20 H22 N6 O6" _chem_comp.mon_nstd_parent_comp_id ? _chem_comp.pdbx_synonyms "antifolate AGF183" _chem_comp.pdbx_formal_charge 0 _chem_comp.pdbx_initial_date 2016-03-28 _chem_comp.pdbx_modified_date 2020-06-17 _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 442.425 _chem_comp.one_letter_code ? _chem_comp.three_letter_code 83A _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 5IZQ _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 83A C1 C1 C 0 1 Y N N -4.343 22.096 -7.122 6.258 -0.012 0.691 C1 83A 1 83A N1 N1 N 0 1 N N N -3.767 21.408 -9.279 7.895 -1.639 1.242 N1 83A 2 83A O1 O1 O 0 1 N N N -5.939 21.229 -8.643 7.128 -0.227 2.799 O1 83A 3 83A C2 C2 C 0 1 N N N -4.790 21.570 -8.366 7.106 -0.617 1.645 C2 83A 4 83A N2 N2 N 0 1 N N N -1.982 22.161 -7.880 7.079 -1.506 -0.950 N2 83A 5 83A O2 O2 O 0 1 N N N -10.431 20.817 2.001 -4.980 2.267 -0.663 O2 83A 6 83A C3 C3 C 0 1 N N N -2.445 21.699 -9.045 7.860 -2.063 -0.053 C3 83A 7 83A N3 N3 N 0 1 N N N -1.599 21.520 -10.058 8.670 -3.103 -0.433 N3 83A 8 83A O3 O3 O 0 1 N N N -10.289 16.568 2.110 -5.633 1.215 2.423 O3 83A 9 83A C4 C4 C 0 1 Y N N -2.948 22.339 -6.958 6.264 -0.490 -0.627 C4 83A 10 83A N4 N4 N 0 1 Y N N -2.766 22.767 -5.676 5.364 0.254 -1.332 N4 83A 11 83A O4 O4 O 0 1 N N N -12.504 16.386 2.278 -7.683 0.452 2.112 O4 83A 12 83A C5 C5 C 0 1 Y N N -3.977 22.800 -5.034 4.782 1.189 -0.513 C5 83A 13 83A N5 N5 N 0 1 N N N -5.931 22.515 -2.064 1.332 2.608 -1.049 N5 83A 14 83A O5 O5 O 0 1 N N N -14.414 18.896 -1.836 -5.720 -4.354 -1.941 O5 83A 15 83A C6 C6 C 0 1 Y N N -4.950 22.417 -5.881 5.284 1.077 0.728 C6 83A 16 83A N6 N6 N 0 1 N N N -10.338 18.897 0.834 -4.513 0.292 0.240 N6 83A 17 83A O6 O6 O 0 1 N N N -13.204 20.452 -2.830 -6.366 -4.145 0.162 O6 83A 18 83A C7 C7 C 0 1 N N N -4.199 23.103 -3.594 3.739 2.189 -0.941 C7 83A 19 83A C8 C8 C 0 1 N N N -4.869 21.959 -2.860 2.346 1.636 -0.633 C8 83A 20 83A C9 C9 C 0 1 Y N N -6.791 21.831 -1.253 -0.017 2.325 -0.868 C9 83A 21 83A C10 C10 C 0 1 Y N N -6.736 20.470 -0.991 -0.980 3.249 -1.264 C10 83A 22 83A C11 C11 C 0 1 Y N N -7.674 19.861 -0.182 -2.316 2.972 -1.087 C11 83A 23 83A C12 C12 C 0 1 Y N N -8.717 20.623 0.376 -2.707 1.761 -0.509 C12 83A 24 83A C13 C13 C 0 1 Y N N -8.756 21.979 0.123 -1.738 0.834 -0.113 C13 83A 25 83A C14 C14 C 0 1 Y N N -7.821 22.578 -0.677 -0.403 1.115 -0.297 C14 83A 26 83A C15 C15 C 0 1 N N N -9.884 20.113 1.156 -4.138 1.461 -0.318 C15 83A 27 83A C16 C16 C 0 1 N N S -11.605 18.403 1.342 -5.935 -0.006 0.430 C16 83A 28 83A C17 C17 C 0 1 N N N -11.455 16.999 1.957 -6.405 0.599 1.728 C17 83A 29 83A C18 C18 C 0 1 N N N -12.669 18.455 0.245 -6.137 -1.522 0.470 C18 83A 30 83A C19 C19 C 0 1 N N N -12.354 19.497 -0.830 -5.777 -2.121 -0.891 C19 83A 31 83A C20 C20 C 0 1 N N N -13.403 19.625 -1.916 -5.976 -3.614 -0.851 C20 83A 32 83A H1 H1 H 0 1 N N N -4.007 21.051 -10.182 8.484 -2.075 1.878 H1 83A 33 83A H2 H2 H 0 1 N N N -0.628 21.731 -9.942 9.256 -3.524 0.215 H2 83A 34 83A H3 H3 H 0 1 N N N -1.934 21.175 -10.935 8.658 -3.417 -1.351 H3 83A 35 83A H4 H4 H 0 1 N N N -1.888 23.017 -5.268 5.164 0.138 -2.274 H4 83A 36 83A H5 H5 H 0 1 N N N -12.277 15.544 2.655 -7.938 0.857 2.952 H5 83A 37 83A H6 H6 H 0 1 N N N -5.484 23.179 -1.465 1.602 3.448 -1.451 H6 83A 38 83A H7 H7 H 0 1 N N N -14.991 19.073 -2.570 -5.863 -5.308 -1.867 H7 83A 39 83A H8 H8 H 0 1 N N N -6.005 22.364 -5.656 5.020 1.677 1.587 H8 83A 40 83A H9 H9 H 0 1 N N N -9.793 18.315 0.230 -3.842 -0.351 0.515 H9 83A 41 83A H10 H10 H 0 1 N N N -3.226 23.305 -3.121 3.887 3.123 -0.399 H10 83A 42 83A H11 H11 H 0 1 N N N -4.837 23.995 -3.515 3.829 2.372 -2.012 H11 83A 43 83A H12 H12 H 0 1 N N N -5.280 21.239 -3.583 2.257 1.453 0.438 H12 83A 44 83A H13 H13 H 0 1 N N N -4.140 21.452 -2.211 2.198 0.701 -1.175 H13 83A 45 83A H14 H14 H 0 1 N N N -5.946 19.877 -1.427 -0.678 4.185 -1.711 H14 83A 46 83A H15 H15 H 0 1 N N N -7.608 18.803 0.022 -3.062 3.690 -1.394 H15 83A 47 83A H16 H16 H 0 1 N N N -9.539 22.578 0.564 -2.036 -0.102 0.335 H16 83A 48 83A H17 H17 H 0 1 N N N -7.880 23.640 -0.865 0.346 0.398 0.005 H17 83A 49 83A H18 H18 H 0 1 N N N -11.936 19.075 2.148 -6.508 0.416 -0.396 H18 83A 50 83A H19 H19 H 0 1 N N N -13.637 18.704 0.704 -5.496 -1.954 1.239 H19 83A 51 83A H20 H20 H 0 1 N N N -12.733 17.465 -0.231 -7.180 -1.743 0.700 H20 83A 52 83A H21 H21 H 0 1 N N N -11.401 19.221 -1.305 -6.418 -1.689 -1.659 H21 83A 53 83A H22 H22 H 0 1 N N N -12.249 20.475 -0.338 -4.735 -1.899 -1.120 H22 83A 54 # # 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 83A N3 C3 SING N N 1 83A N1 C3 SING N N 2 83A N1 C2 SING N N 3 83A C3 N2 DOUB N N 4 83A O1 C2 DOUB N N 5 83A C2 C1 SING N N 6 83A N2 C4 SING N N 7 83A C1 C4 DOUB Y N 8 83A C1 C6 SING Y N 9 83A C4 N4 SING Y N 10 83A C6 C5 DOUB Y N 11 83A N4 C5 SING Y N 12 83A C5 C7 SING N N 13 83A C7 C8 SING N N 14 83A C8 N5 SING N N 15 83A O6 C20 DOUB N N 16 83A N5 C9 SING N N 17 83A C20 O5 SING N N 18 83A C20 C19 SING N N 19 83A C9 C10 DOUB Y N 20 83A C9 C14 SING Y N 21 83A C10 C11 SING Y N 22 83A C19 C18 SING N N 23 83A C14 C13 DOUB Y N 24 83A C11 C12 DOUB Y N 25 83A C13 C12 SING Y N 26 83A C18 C16 SING N N 27 83A C12 C15 SING N N 28 83A N6 C15 SING N N 29 83A N6 C16 SING N N 30 83A C15 O2 DOUB N N 31 83A C16 C17 SING N N 32 83A C17 O3 DOUB N N 33 83A C17 O4 SING N N 34 83A N1 H1 SING N N 35 83A N3 H2 SING N N 36 83A N3 H3 SING N N 37 83A N4 H4 SING N N 38 83A O4 H5 SING N N 39 83A N5 H6 SING N N 40 83A O5 H7 SING N N 41 83A C6 H8 SING N N 42 83A N6 H9 SING N N 43 83A C7 H10 SING N N 44 83A C7 H11 SING N N 45 83A C8 H12 SING N N 46 83A C8 H13 SING N N 47 83A C10 H14 SING N N 48 83A C11 H15 SING N N 49 83A C13 H16 SING N N 50 83A C14 H17 SING N N 51 83A C16 H18 SING N N 52 83A C18 H19 SING N N 53 83A C18 H20 SING N N 54 83A C19 H21 SING N N 55 83A C19 H22 SING N N 56 # # 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 83A SMILES ACDLabs 12.01 "c31c(N=C(NC1=O)N)nc(CCNc2ccc(C(=O)NC(C(=O)O)CCC(O)=O)cc2)c3" 83A InChI InChI 1.03 "InChI=1S/C20H22N6O6/c21-20-25-16-13(18(30)26-20)9-12(23-16)7-8-22-11-3-1-10(2-4-11)17(29)24-14(19(31)32)5-6-15(27)28/h1-4,9,14,22H,5-8H2,(H,24,29)(H,27,28)(H,31,32)(H4,21,23,25,26,30)/t14-/m0/s1" 83A InChIKey InChI 1.03 UFNWIIALSMNORN-AWEZNQCLSA-N 83A SMILES_CANONICAL CACTVS 3.385 "NC1=Nc2[nH]c(CCNc3ccc(cc3)C(=O)N[C@@H](CCC(O)=O)C(O)=O)cc2C(=O)N1" 83A SMILES CACTVS 3.385 "NC1=Nc2[nH]c(CCNc3ccc(cc3)C(=O)N[CH](CCC(O)=O)C(O)=O)cc2C(=O)N1" 83A SMILES_CANONICAL "OpenEye OEToolkits" 2.0.4 "c1cc(ccc1C(=O)N[C@@H](CCC(=O)O)C(=O)O)NCCc2cc3c([nH]2)N=C(NC3=O)N" 83A SMILES "OpenEye OEToolkits" 2.0.4 "c1cc(ccc1C(=O)NC(CCC(=O)O)C(=O)O)NCCc2cc3c([nH]2)N=C(NC3=O)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 83A "SYSTEMATIC NAME" ACDLabs 12.01 "N-(4-{[2-(2-amino-4-oxo-4,7-dihydro-3H-pyrrolo[2,3-d]pyrimidin-6-yl)ethyl]amino}benzene-1-carbonyl)-L-glutamic acid" 83A "SYSTEMATIC NAME" "OpenEye OEToolkits" 2.0.4 "(2~{S})-2-[[4-[2-(2-azanyl-4-oxidanylidene-3,7-dihydropyrrolo[2,3-d]pyrimidin-6-yl)ethylamino]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 83A "Create component" 2016-03-28 RCSB 83A "Initial release" 2016-08-10 RCSB 83A "Modify synonyms" 2020-06-05 PDBE # _pdbx_chem_comp_synonyms.ordinal 1 _pdbx_chem_comp_synonyms.comp_id 83A _pdbx_chem_comp_synonyms.name "antifolate AGF183" _pdbx_chem_comp_synonyms.provenance ? _pdbx_chem_comp_synonyms.type ? ##