data_MS1 # _chem_comp.id MS1 _chem_comp.name "2-[4-((2-AMINO-4-OXO-3,4-DIHYDRO-PYRIDO[3,2-D]PYRIMIDIN-6-YLMETHYL)-{3-[5-CARBAMOYL-3-(3,4- DIHYDROXY-5-PHOSPHONOOXYMETHYL-TETRAHYDRO-FURAN-2-YL)-3H-IMIDAZOL-4-YL]-ACRYLOYL}-AMINO)-BENZOYLAMINO]- PENTANEDIOIC ACID" _chem_comp.type NON-POLYMER _chem_comp.pdbx_type HETAIN _chem_comp.formula "C32 H34 N9 O15 P" _chem_comp.mon_nstd_parent_comp_id ? _chem_comp.pdbx_synonyms "BETA-DADF; MSA; MULTISUBSTRATE ADDUCT INHIBITOR" _chem_comp.pdbx_formal_charge 0 _chem_comp.pdbx_initial_date 2003-04-25 _chem_comp.pdbx_modified_date 2020-05-27 _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 815.637 _chem_comp.one_letter_code ? _chem_comp.three_letter_code MS1 _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 1OZ0 _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 MS1 OE1 OE1 O 0 1 N N N 70.735 55.366 61.027 -4.503 -0.298 9.128 OE1 MS1 1 MS1 CD CD C 0 1 N N N 70.366 56.386 61.627 -3.283 -0.058 9.634 CD MS1 2 MS1 OE2 OE2 O 0 1 N N N 71.208 57.375 62.051 -2.991 -0.477 10.729 OE2 MS1 3 MS1 CG CG C 0 1 N N N 68.901 56.661 62.000 -2.279 0.734 8.838 CG MS1 4 MS1 CB CB C 0 1 N N N 68.879 57.797 63.023 -0.981 0.862 9.637 CB MS1 5 MS1 CA CA C 0 1 N N S 67.549 58.348 63.678 0.038 1.667 8.828 CA MS1 6 MS1 N N N 0 1 N N N 66.246 57.786 63.199 0.309 0.980 7.563 N MS1 7 MS1 C17 C17 C 0 1 N N N 65.704 57.016 64.166 0.647 1.691 6.469 C17 MS1 8 MS1 O17 O17 O 0 1 N N N 66.367 56.819 65.215 0.727 2.903 6.532 O17 MS1 9 MS1 C14 C14 C 0 1 Y N N 64.323 56.453 64.031 0.920 0.999 5.194 C14 MS1 10 MS1 C13 C13 C 0 1 Y N N 63.669 55.675 65.024 1.271 1.735 4.059 C13 MS1 11 MS1 C12 C12 C 0 1 Y N N 62.326 55.221 64.861 1.526 1.087 2.872 C12 MS1 12 MS1 C11 C11 C 0 1 Y N N 61.532 55.488 63.687 1.435 -0.299 2.801 C11 MS1 13 MS1 C16 C16 C 0 1 Y N N 62.237 56.271 62.676 1.080 -1.035 3.928 C16 MS1 14 MS1 C15 C15 C 0 1 Y N N 63.570 56.748 62.831 0.829 -0.393 5.120 C15 MS1 15 MS1 N10 N10 N 0 1 N N N 60.053 54.964 63.571 1.693 -0.952 1.598 N10 MS1 16 MS1 C42 C42 C 0 1 N N N 59.064 55.184 64.435 2.189 -0.264 0.551 C42 MS1 17 MS1 O42 O42 O 0 1 N N N 57.853 54.921 64.271 2.526 0.896 0.690 O42 MS1 18 MS1 C2P C2P C 0 1 N N N 59.326 55.897 65.760 2.322 -0.913 -0.753 C2P MS1 19 MS1 C3P C3P C 0 1 N N N 59.269 55.958 67.152 2.724 -0.196 -1.827 C3P MS1 20 MS1 C4P C4P C 0 1 Y N N 59.510 56.735 68.351 2.753 -0.816 -3.152 C4P MS1 21 MS1 C5P C5P C 0 1 Y N N 60.208 57.969 68.384 3.439 -1.973 -3.521 C5P MS1 22 MS1 N7 N7 N 0 1 Y N N 60.954 58.007 69.589 3.190 -2.182 -4.826 N7 MS1 23 MS1 C8 C8 C 0 1 Y N N 60.624 56.788 70.114 2.411 -1.239 -5.278 C8 MS1 24 MS1 N9 N9 N 0 1 Y N N 59.768 55.959 69.392 2.119 -0.373 -4.286 N9 MS1 25 MS1 C1 C1 C 0 1 N N R 59.182 54.631 69.619 1.273 0.817 -4.396 C1 MS1 26 MS1 O1 O1 O 0 1 N N N 58.281 54.814 70.695 0.304 0.649 -5.453 O1 MS1 27 MS1 C4 C4 C 0 1 N N R 58.958 54.122 71.712 -0.112 1.987 -5.804 C4 MS1 28 MS1 C5 C5 C 0 1 N N N 59.200 54.991 72.927 -0.726 2.004 -7.205 C5 MS1 29 MS1 O6 O6 O 0 1 N N N 60.656 55.167 73.022 -1.882 1.166 -7.228 O6 MS1 30 MS1 P P P 0 1 N N N 61.389 55.765 74.325 -2.474 1.230 -8.724 P MS1 31 MS1 O9 O9 O 0 1 N N N 60.324 56.641 75.148 -1.454 0.745 -9.680 O9 MS1 32 MS1 O8 O8 O 0 1 N N N 61.936 54.558 75.245 -3.786 0.303 -8.823 O8 MS1 33 MS1 O7 O7 O 0 1 N N N 62.604 56.707 73.851 -2.863 2.751 -9.082 O7 MS1 34 MS1 C3 C3 C 0 1 N N S 60.368 53.754 71.247 1.185 2.825 -5.772 C3 MS1 35 MS1 O3 O3 O 0 1 N N N 60.724 52.465 71.723 0.925 4.131 -5.252 O3 MS1 36 MS1 C2 C2 C 0 1 N N R 60.347 53.729 69.751 2.118 2.039 -4.822 C2 MS1 37 MS1 O2 O2 O 0 1 N N N 60.104 52.511 69.049 2.465 2.836 -3.688 O2 MS1 38 MS1 C6 C6 C 0 1 N N N 60.197 59.091 67.349 4.275 -2.813 -2.643 C6 MS1 39 MS1 O62 O62 O 0 1 N N N 59.291 59.223 66.558 4.496 -2.465 -1.499 O62 MS1 40 MS1 N1 N1 N 0 1 N N N 61.191 59.965 67.265 4.794 -3.966 -3.109 N1 MS1 41 MS1 C9 C9 C 0 1 N N N 59.682 54.176 62.331 1.425 -2.387 1.472 C9 MS1 42 MS1 C6F C6F C 0 1 Y N N 60.161 54.687 60.981 0.051 -2.592 0.889 C6F MS1 43 MS1 N5F N5F N 0 1 Y N N 59.558 55.772 60.477 -0.645 -1.547 0.503 N5F MS1 44 MS1 C4A C4A C 0 1 Y N N 59.886 56.271 59.304 -1.856 -1.683 -0.019 C4A MS1 45 MS1 C8A C8A C 0 1 Y N N 60.956 55.671 58.490 -2.433 -2.963 -0.163 C8A MS1 46 MS1 N1F N1F N 0 1 Y N N 61.302 56.243 57.193 -3.672 -3.077 -0.694 N1F MS1 47 MS1 C2F C2F C 0 1 Y N N 60.683 57.291 56.719 -4.352 -2.026 -1.080 C2F MS1 48 MS1 N2F N2F N 0 1 N N N 61.047 57.794 55.491 -5.603 -2.215 -1.611 N2F MS1 49 MS1 N3F N3F N 0 1 Y N N 59.612 57.951 57.464 -3.872 -0.753 -0.977 N3F MS1 50 MS1 C4F C4F C 0 1 Y N N 59.182 57.518 58.698 -2.644 -0.519 -0.461 C4F MS1 51 MS1 O4F O4F O 0 1 N N N 58.274 58.149 59.240 -2.206 0.611 -0.365 O4F MS1 52 MS1 C8F C8F C 0 1 Y N N 61.626 54.538 59.011 -1.701 -4.085 0.250 C8F MS1 53 MS1 C7F C7F C 0 1 Y N N 61.223 54.018 60.277 -0.454 -3.883 0.777 C7F MS1 54 MS1 C C C 0 1 N N N 67.545 59.894 63.665 1.316 1.793 9.615 C MS1 55 MS1 O O O 0 1 N N N 66.699 60.594 63.066 1.475 2.728 10.364 O MS1 56 MS1 OT OT O 0 1 N N N 68.589 60.414 64.400 2.279 0.867 9.484 OT MS1 57 MS1 HE1 HE1 H 0 1 N N N 70.149 54.678 60.732 -5.147 -0.806 9.639 HE1 MS1 58 MS1 HG1 1HG H 0 1 N N N 68.261 56.869 61.110 -2.680 1.727 8.633 HG1 MS1 59 MS1 HG2 2HG H 0 1 N N N 68.368 55.748 62.357 -2.078 0.223 7.896 HG2 MS1 60 MS1 HB1 1HB H 0 1 N N N 69.563 57.508 63.854 -0.581 -0.130 9.841 HB1 MS1 61 MS1 HB2 2HB H 0 1 N N N 69.408 58.665 62.566 -1.183 1.373 10.578 HB2 MS1 62 MS1 HA HA H 0 1 N N N 67.593 57.959 64.722 -0.362 2.660 8.624 HA MS1 63 MS1 HN HN H 0 1 N N N 65.774 57.914 62.303 0.245 0.013 7.512 HN MS1 64 MS1 H13 H13 H 0 1 N N N 64.218 55.416 65.945 1.343 2.811 4.114 H13 MS1 65 MS1 H12 H12 H 0 1 N N N 61.880 54.635 65.682 1.797 1.655 1.994 H12 MS1 66 MS1 H16 H16 H 0 1 N N N 61.727 56.519 61.729 1.009 -2.111 3.870 H16 MS1 67 MS1 H15 H15 H 0 1 N N N 64.019 57.346 62.020 0.558 -0.964 5.995 H15 MS1 68 MS1 H2P H2P H 0 1 N N N 59.808 56.883 65.658 2.099 -1.965 -0.858 H2P MS1 69 MS1 H3P H3P H 0 1 N N N 58.857 54.969 67.418 3.023 0.834 -1.707 H3P MS1 70 MS1 H8 H8 H 0 1 N N N 61.035 56.482 71.090 2.055 -1.162 -6.295 H8 MS1 71 MS1 H1 H1 H 0 1 N N N 58.557 54.150 68.830 0.772 1.015 -3.449 H1 MS1 72 MS1 H4 H4 H 0 1 N N N 58.318 53.240 71.952 -0.826 2.366 -5.073 H4 MS1 73 MS1 H51 1H5 H 0 1 N N N 58.637 55.953 72.902 -1.011 3.024 -7.464 H51 MS1 74 MS1 H52 2H5 H 0 1 N N N 58.740 54.587 73.859 0.004 1.636 -7.926 H52 MS1 75 MS1 HO8 HO8 H 0 1 N N N 62.368 54.910 76.013 -4.108 0.370 -9.733 HO8 MS1 76 MS1 HO7 HO7 H 0 1 N N N 63.036 57.059 74.619 -3.529 3.028 -8.438 HO7 MS1 77 MS1 H3 H3 H 0 1 N N N 61.107 54.492 71.636 1.621 2.892 -6.769 H3 MS1 78 MS1 HO3 HO3 H 0 1 N N N 61.599 52.236 71.434 1.767 4.606 -5.257 HO3 MS1 79 MS1 H2 H2 H 0 1 N N N 61.342 53.968 69.309 3.016 1.715 -5.349 H2 MS1 80 MS1 HO2 HO2 H 0 1 N N N 60.852 51.931 69.133 2.936 3.610 -4.024 HO2 MS1 81 MS1 HN11 1HN1 H 0 0 N N N 61.954 59.853 67.931 5.344 -4.519 -2.531 HN11 MS1 82 MS1 HN12 2HN1 H 0 0 N N N 61.183 60.714 66.573 4.614 -4.246 -4.020 HN12 MS1 83 MS1 H91 1H9 H 0 1 N N N 60.015 53.119 62.458 1.477 -2.854 2.455 H91 MS1 84 MS1 H92 2H9 H 0 1 N N N 58.574 54.048 62.299 2.169 -2.839 0.815 H92 MS1 85 MS1 H2F1 1H2F H 0 0 N N N 60.563 58.612 55.120 -5.965 -3.111 -1.693 H2F1 MS1 86 MS1 H2F2 2H2F H 0 0 N N N 60.991 57.043 54.802 -6.125 -1.451 -1.903 H2F2 MS1 87 MS1 H3F H3F H 0 1 N N N 59.130 58.771 57.096 -4.417 -0.009 -1.278 H3F MS1 88 MS1 H8F H8F H 0 1 N N N 62.446 54.069 58.441 -2.109 -5.080 0.155 H8F MS1 89 MS1 H7F H7F H 0 1 N N N 61.717 53.126 60.698 0.137 -4.725 1.105 H7F MS1 90 MS1 HOT HOT H 0 1 N N N 68.586 61.364 64.392 3.100 0.948 9.989 HOT MS1 91 # 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 MS1 OE1 CD SING N N 1 MS1 OE1 HE1 SING N N 2 MS1 CD OE2 DOUB N N 3 MS1 CD CG SING N N 4 MS1 CG CB SING N N 5 MS1 CG HG1 SING N N 6 MS1 CG HG2 SING N N 7 MS1 CB CA SING N N 8 MS1 CB HB1 SING N N 9 MS1 CB HB2 SING N N 10 MS1 CA N SING N N 11 MS1 CA C SING N N 12 MS1 CA HA SING N N 13 MS1 N C17 SING N N 14 MS1 N HN SING N N 15 MS1 C17 O17 DOUB N N 16 MS1 C17 C14 SING N N 17 MS1 C14 C13 DOUB Y N 18 MS1 C14 C15 SING Y N 19 MS1 C13 C12 SING Y N 20 MS1 C13 H13 SING N N 21 MS1 C12 C11 DOUB Y N 22 MS1 C12 H12 SING N N 23 MS1 C11 C16 SING Y N 24 MS1 C11 N10 SING N N 25 MS1 C16 C15 DOUB Y N 26 MS1 C16 H16 SING N N 27 MS1 C15 H15 SING N N 28 MS1 N10 C42 SING N N 29 MS1 N10 C9 SING N N 30 MS1 C42 O42 DOUB N N 31 MS1 C42 C2P SING N N 32 MS1 C2P C3P DOUB N E 33 MS1 C2P H2P SING N N 34 MS1 C3P C4P SING N N 35 MS1 C3P H3P SING N N 36 MS1 C4P C5P DOUB Y N 37 MS1 C4P N9 SING Y N 38 MS1 C5P N7 SING Y N 39 MS1 C5P C6 SING N N 40 MS1 N7 C8 DOUB Y N 41 MS1 C8 N9 SING Y N 42 MS1 C8 H8 SING N N 43 MS1 N9 C1 SING N N 44 MS1 C1 O1 SING N N 45 MS1 C1 C2 SING N N 46 MS1 C1 H1 SING N N 47 MS1 O1 C4 SING N N 48 MS1 C4 C5 SING N N 49 MS1 C4 C3 SING N N 50 MS1 C4 H4 SING N N 51 MS1 C5 O6 SING N N 52 MS1 C5 H51 SING N N 53 MS1 C5 H52 SING N N 54 MS1 O6 P SING N N 55 MS1 P O9 DOUB N N 56 MS1 P O8 SING N N 57 MS1 P O7 SING N N 58 MS1 O8 HO8 SING N N 59 MS1 O7 HO7 SING N N 60 MS1 C3 O3 SING N N 61 MS1 C3 C2 SING N N 62 MS1 C3 H3 SING N N 63 MS1 O3 HO3 SING N N 64 MS1 C2 O2 SING N N 65 MS1 C2 H2 SING N N 66 MS1 O2 HO2 SING N N 67 MS1 C6 O62 DOUB N N 68 MS1 C6 N1 SING N N 69 MS1 N1 HN11 SING N N 70 MS1 N1 HN12 SING N N 71 MS1 C9 C6F SING N N 72 MS1 C9 H91 SING N N 73 MS1 C9 H92 SING N N 74 MS1 C6F N5F DOUB Y N 75 MS1 C6F C7F SING Y N 76 MS1 N5F C4A SING Y N 77 MS1 C4A C8A DOUB Y N 78 MS1 C4A C4F SING Y N 79 MS1 C8A N1F SING Y N 80 MS1 C8A C8F SING Y N 81 MS1 N1F C2F DOUB Y N 82 MS1 C2F N2F SING N N 83 MS1 C2F N3F SING Y N 84 MS1 N2F H2F1 SING N N 85 MS1 N2F H2F2 SING N N 86 MS1 N3F C4F SING Y N 87 MS1 N3F H3F SING N N 88 MS1 C4F O4F DOUB N N 89 MS1 C8F C7F DOUB Y N 90 MS1 C8F H8F SING N N 91 MS1 C7F H7F SING N N 92 MS1 C O DOUB N N 93 MS1 C OT SING N N 94 MS1 OT HOT SING N N 95 # 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 MS1 SMILES ACDLabs 10.04 "O=C(O)C(NC(=O)c1ccc(cc1)N(C(=O)\C=C\c2c(ncn2C3OC(C(O)C3O)COP(=O)(O)O)C(=O)N)Cc5nc4c(N=C(N)NC4=O)cc5)CCC(=O)O" MS1 SMILES_CANONICAL CACTVS 3.341 "NC(=O)c1ncn([C@@H]2O[C@H](CO[P](O)(O)=O)[C@@H](O)[C@H]2O)c1/C=C/C(=O)N(Cc3ccc4N=C(N)NC(=O)c4n3)c5ccc(cc5)C(=O)N[C@@H](CCC(O)=O)C(O)=O" MS1 SMILES CACTVS 3.341 "NC(=O)c1ncn([CH]2O[CH](CO[P](O)(O)=O)[CH](O)[CH]2O)c1C=CC(=O)N(Cc3ccc4N=C(N)NC(=O)c4n3)c5ccc(cc5)C(=O)N[CH](CCC(O)=O)C(O)=O" MS1 SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 "c1cc(ccc1C(=O)N[C@@H](CCC(=O)O)C(=O)O)N(Cc2ccc3c(n2)C(=O)NC(=N3)N)C(=O)\C=C\c4c(ncn4[C@H]5[C@@H]([C@@H]([C@H](O5)COP(=O)(O)O)O)O)C(=O)N" MS1 SMILES "OpenEye OEToolkits" 1.5.0 "c1cc(ccc1C(=O)NC(CCC(=O)O)C(=O)O)N(Cc2ccc3c(n2)C(=O)NC(=N3)N)C(=O)C=Cc4c(ncn4C5C(C(C(O5)COP(=O)(O)O)O)O)C(=O)N" MS1 InChI InChI 1.03 "InChI=1S/C32H34N9O15P/c33-27(47)24-19(41(13-35-24)30-26(46)25(45)20(56-30)12-55-57(52,53)54)8-9-21(42)40(11-15-3-6-17-23(36-15)29(49)39-32(34)38-17)16-4-1-14(2-5-16)28(48)37-18(31(50)51)7-10-22(43)44/h1-6,8-9,13,18,20,25-26,30,45-46H,7,10-12H2,(H2,33,47)(H,37,48)(H,43,44)(H,50,51)(H2,52,53,54)(H3,34,38,39,49)/b9-8+/t18-,20+,25+,26+,30+/m0/s1" MS1 InChIKey InChI 1.03 XRZABKCMPVBQFX-UGTLBTQMSA-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 MS1 "SYSTEMATIC NAME" ACDLabs 10.04 "N-{[4-([(2-amino-4-oxo-3,4-dihydropyrido[3,2-d]pyrimidin-6-yl)methyl]{(2E)-3-[4-carbamoyl-1-(5-O-phosphono-beta-D-ribofuranosyl)-1H-imidazol-5-yl]prop-2-enoyl}amino)phenyl]carbonyl}-L-glutamic acid" MS1 "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "(2S)-2-[[4-[[(E)-3-[5-aminocarbonyl-3-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(phosphonooxymethyl)oxolan-2-yl]imidazol-4-yl]prop-2-enoyl]-[(2-amino-4-oxo-3H-pyrido[5,6-d]pyrimidin-6-yl)methyl]amino]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 MS1 "Create component" 2003-04-25 RCSB MS1 "Modify descriptor" 2011-06-04 RCSB MS1 "Modify synonyms" 2020-05-27 PDBE # loop_ _pdbx_chem_comp_synonyms.ordinal _pdbx_chem_comp_synonyms.comp_id _pdbx_chem_comp_synonyms.name _pdbx_chem_comp_synonyms.provenance _pdbx_chem_comp_synonyms.type 1 MS1 BETA-DADF ? ? 2 MS1 MSA ? ? 3 MS1 "MULTISUBSTRATE ADDUCT INHIBITOR" ? ? #