data_BGD # _chem_comp.id BGD _chem_comp.name "N-BENZOYL-L-GLUTAMYL-[4-PHOSPHONO(DIFLUOROMETHYL)]-L-PHENYLALANINE-[4-PHOSPHONO(DIFLUORO-METHYL)]-L-PHENYLALANINEAMIDE" _chem_comp.type NON-POLYMER _chem_comp.pdbx_type HETAIN _chem_comp.formula "C32 H34 F4 N4 O12 P2" _chem_comp.mon_nstd_parent_comp_id ? _chem_comp.pdbx_synonyms "4-BENZOYLAMINO-4-{1-{1-CARBAMOYL-2-[4-(DIFLUORO-PHOSPHONO-METHYL)-PHENYL]-ETHYLCARBAMOYL}-2-[4-(DIFLUORO-PHOSPHONO-METHYL)-PHENYL]-ETHYLCARBAMOYL}-BUTYRIC ACID" _chem_comp.pdbx_formal_charge 0 _chem_comp.pdbx_initial_date 2002-05-16 _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 804.573 _chem_comp.one_letter_code ? _chem_comp.three_letter_code BGD _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 1LQF _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 BGD C1 C1 C 0 1 N N N 73.768 -1.444 -16.675 -1.414 -1.139 0.797 C1 BGD 1 BGD O2 O2 O 0 1 N N N 72.855 -1.114 -17.476 -1.443 -0.343 -0.117 O2 BGD 2 BGD C3 C3 C 0 1 N N N 76.228 -0.915 -16.413 -1.622 -3.610 0.818 C3 BGD 3 BGD C4 C4 C 0 1 N N N 76.519 -1.173 -17.933 -2.605 -4.772 0.975 C4 BGD 4 BGD C5 C5 C 0 1 N N N 76.601 0.117 -18.748 -1.848 -6.075 0.965 C5 BGD 5 BGD O6 O6 O 0 1 N N N 77.655 0.368 -19.376 -0.646 -6.074 0.845 O6 BGD 6 BGD O7 O7 O 0 1 N N N 75.619 0.929 -18.825 -2.510 -7.236 1.090 O7 BGD 7 BGD C8 C8 C 0 1 N N N 73.841 0.761 -14.045 -4.485 -2.781 -0.314 C8 BGD 8 BGD O9 O9 O 0 1 N N N 73.240 1.575 -14.790 -4.867 -3.345 0.693 O9 BGD 9 BGD C10 C10 C 0 1 Y N N 73.678 0.879 -12.551 -5.364 -2.713 -1.501 C10 BGD 10 BGD C11 C11 C 0 1 Y N N 72.823 1.940 -11.951 -6.632 -3.294 -1.469 C11 BGD 11 BGD C12 C12 C 0 1 Y N N 74.359 -0.064 -11.631 -4.931 -2.062 -2.657 C12 BGD 12 BGD C13 C13 C 0 1 Y N N 72.649 2.055 -10.491 -7.447 -3.227 -2.580 C13 BGD 13 BGD C14 C14 C 0 1 Y N N 74.179 0.062 -10.177 -5.753 -2.006 -3.763 C14 BGD 14 BGD C15 C15 C 0 1 Y N N 73.329 1.113 -9.596 -7.010 -2.585 -3.724 C15 BGD 15 BGD N16 N16 N 0 1 N N N 74.620 -0.226 -14.616 -3.261 -2.219 -0.349 N16 BGD 16 BGD C17 C17 C 0 1 N N S 74.777 -0.407 -16.118 -2.390 -2.287 0.828 C17 BGD 17 BGD N18 N18 N 0 1 N N N 73.949 -2.683 -16.210 -0.509 -0.997 1.786 N18 BGD 18 BGD C19 C19 C 0 1 N N S 73.138 -3.870 -16.531 0.439 0.119 1.756 C19 BGD 19 BGD C20 C20 C 0 1 N N N 72.857 -4.503 -15.159 1.671 -0.248 2.544 C20 BGD 20 BGD O21 O21 O 0 1 N N N 73.741 -4.469 -14.306 1.748 -1.334 3.078 O21 BGD 21 BGD C22 C22 C 0 1 N N N 73.925 -4.923 -17.370 -0.211 1.358 2.373 C22 BGD 22 BGD C23 C23 C 0 1 Y N N 74.257 -4.581 -18.802 -1.370 1.797 1.515 C23 BGD 23 BGD C24 C24 C 0 1 Y N N 75.364 -5.270 -19.444 -2.636 1.297 1.756 C24 BGD 24 BGD C25 C25 C 0 1 Y N N 75.735 -4.990 -20.819 -3.699 1.699 0.969 C25 BGD 25 BGD C26 C26 C 0 1 Y N N 73.497 -3.574 -19.570 -1.168 2.704 0.492 C26 BGD 26 BGD C27 C27 C 0 1 Y N N 73.863 -3.287 -20.947 -2.230 3.103 -0.298 C27 BGD 27 BGD C28 C28 C 0 1 Y N N 74.989 -3.987 -21.610 -3.496 2.602 -0.058 C28 BGD 28 BGD C29 C29 C 0 1 N N N 75.413 -3.683 -23.127 -4.654 3.040 -0.917 C29 BGD 29 BGD F30 F30 F 0 1 N N N 75.882 -2.358 -23.136 -4.205 3.279 -2.220 F30 BGD 30 BGD F31 F31 F 0 1 N N N 76.515 -4.518 -23.483 -5.627 2.035 -0.936 F31 BGD 31 BGD P32 P32 P 0 1 N N N 74.347 -3.792 -24.324 -5.374 4.569 -0.232 P32 BGD 32 BGD O33 O33 O 0 1 N N N 75.030 -3.292 -25.668 -6.456 5.046 -1.122 O33 BGD 33 BGD O34 O34 O 0 1 N N N 73.888 -5.286 -24.565 -5.974 4.271 1.232 O34 BGD 34 BGD O35 O35 O 0 1 N N N 73.060 -2.904 -24.042 -4.231 5.698 -0.124 O35 BGD 35 BGD N36 N36 N 0 1 N N N 71.672 -5.060 -14.921 2.686 0.632 2.656 N36 BGD 36 BGD C37 C37 C 0 1 N N S 71.364 -5.662 -13.605 3.882 0.276 3.422 C37 BGD 37 BGD C38 C38 C 0 1 N N N 69.917 -5.134 -13.242 5.074 1.091 2.915 C38 BGD 38 BGD C39 C39 C 0 1 Y N N 69.267 -5.516 -11.943 5.381 0.700 1.492 C39 BGD 39 BGD C40 C40 C 0 1 Y N N 68.199 -6.451 -11.996 4.774 1.368 0.445 C40 BGD 40 BGD C41 C41 C 0 1 Y N N 67.492 -6.879 -10.797 5.055 1.010 -0.860 C41 BGD 41 BGD C42 C42 C 0 1 Y N N 69.666 -4.962 -10.637 6.273 -0.324 1.234 C42 BGD 42 BGD C43 C43 C 0 1 Y N N 68.958 -5.384 -9.406 6.551 -0.685 -0.071 C43 BGD 43 BGD C44 C44 C 0 1 Y N N 67.847 -6.365 -9.473 5.944 -0.017 -1.118 C44 BGD 44 BGD C45 C45 C 0 1 N N N 67.034 -6.861 -8.199 6.249 -0.409 -2.541 C45 BGD 45 BGD F46 F46 F 0 1 N N N 66.398 -8.099 -8.446 6.584 -1.766 -2.589 F46 BGD 46 BGD F47 F47 F 0 1 N N N 67.911 -7.104 -7.156 5.125 -0.177 -3.340 F47 BGD 47 BGD P48 P48 P 0 1 N N N 65.871 -5.873 -7.723 7.649 0.584 -3.157 P48 BGD 48 BGD O49 O49 O 0 1 N N N 66.429 -4.542 -7.112 7.870 0.289 -4.590 O49 BGD 49 BGD O50 O50 O 0 1 N N N 64.961 -5.469 -8.937 7.316 2.149 -2.977 O50 BGD 50 BGD O51 O51 O 0 1 N N N 65.022 -6.590 -6.662 8.976 0.218 -2.322 O51 BGD 51 BGD C52 C52 C 0 1 N N N 71.432 -7.232 -13.642 3.653 0.577 4.881 C52 BGD 52 BGD O53 O53 O 0 1 N N N 71.379 -7.873 -12.559 2.594 1.042 5.244 O53 BGD 53 BGD N54 N54 N 0 1 N N N 71.548 -7.809 -14.747 4.624 0.328 5.781 N54 BGD 54 BGD H31 1H3 H 0 1 N N N 76.982 -0.215 -15.984 -1.086 -3.712 -0.126 H31 BGD 55 BGD H32 2H3 H 0 1 N N N 76.453 -1.827 -15.812 -0.910 -3.623 1.643 H32 BGD 56 BGD H41A 1H4 H 0 0 N N N 75.770 -1.874 -18.369 -3.141 -4.670 1.918 H41A BGD 57 BGD H42A 2H4 H 0 0 N N N 77.440 -1.787 -18.064 -3.317 -4.759 0.149 H42A BGD 58 BGD H7 H7 H 0 1 N N N 75.670 1.731 -19.332 -2.024 -8.072 1.083 H7 BGD 59 BGD H11 H11 H 0 1 N N N 72.304 2.660 -12.606 -6.975 -3.797 -0.576 H11 BGD 60 BGD H12 H12 H 0 1 N N N 75.004 -0.865 -12.031 -3.950 -1.610 -2.689 H12 BGD 61 BGD H13 H13 H 0 1 N N N 72.009 2.847 -10.067 -8.429 -3.676 -2.556 H13 BGD 62 BGD H14 H14 H 0 1 N N N 74.693 -0.648 -9.507 -5.418 -1.506 -4.660 H14 BGD 63 BGD H15 H15 H 0 1 N N N 73.203 1.194 -8.503 -7.651 -2.535 -4.592 H15 BGD 64 BGD H16 H16 H 0 1 N N N 75.080 -0.822 -13.928 -2.956 -1.769 -1.152 H16 BGD 65 BGD H17 H17 H 0 1 N N N 74.583 0.574 -16.611 -2.996 -2.225 1.732 H17 BGD 66 BGD H18 H18 H 0 1 N N N 74.748 -2.725 -15.577 -0.486 -1.634 2.517 H18 BGD 67 BGD H19 H19 H 0 1 N N N 72.238 -3.580 -17.122 0.719 0.331 0.724 H19 BGD 68 BGD H221 1H22 H 0 0 N N N 73.379 -5.895 -17.343 -0.570 1.119 3.374 H221 BGD 69 BGD H222 2H22 H 0 0 N N N 74.863 -5.193 -16.831 0.522 2.162 2.432 H222 BGD 70 BGD H24 H24 H 0 1 N N N 75.936 -6.022 -18.875 -2.795 0.591 2.558 H24 BGD 71 BGD H25 H25 H 0 1 N N N 76.583 -5.539 -21.262 -4.688 1.308 1.156 H25 BGD 72 BGD H26 H26 H 0 1 N N N 72.651 -3.033 -19.113 -0.179 3.095 0.305 H26 BGD 73 BGD H27 H27 H 0 1 N N N 73.279 -2.529 -21.495 -2.071 3.808 -1.100 H27 BGD 74 BGD H34 H34 H 0 1 N N N 73.258 -5.350 -25.273 -5.238 3.964 1.778 H34 BGD 75 BGD H35 H35 H 0 1 N N N 72.430 -2.968 -24.750 -4.653 6.488 0.241 H35 BGD 76 BGD H36 H36 H 0 1 N N N 71.029 -5.027 -15.712 2.624 1.501 2.229 H36 BGD 77 BGD H37 H37 H 0 1 N N N 72.113 -5.370 -12.832 4.090 -0.787 3.299 H37 BGD 78 BGD H381 1H38 H 0 0 N N N 69.226 -5.411 -14.072 4.832 2.153 2.956 H381 BGD 79 BGD H382 2H38 H 0 0 N N N 69.923 -4.021 -13.315 5.943 0.892 3.542 H382 BGD 80 BGD H40 H40 H 0 1 N N N 67.914 -6.851 -12.984 4.079 2.171 0.647 H40 BGD 81 BGD H41 H41 H 0 1 N N N 66.670 -7.608 -10.894 4.580 1.532 -1.677 H41 BGD 82 BGD H42 H42 H 0 1 N N N 70.492 -4.233 -10.581 6.748 -0.845 2.051 H42 BGD 83 BGD H43 H43 H 0 1 N N N 69.261 -4.964 -8.432 7.245 -1.488 -0.273 H43 BGD 84 BGD H50 H50 H 0 1 N N N 64.270 -4.882 -8.654 8.080 2.638 -3.314 H50 BGD 85 BGD H51 H51 H 0 1 N N N 64.331 -6.003 -6.379 8.822 0.505 -1.412 H51 BGD 86 BGD H541 1H54 H 0 0 N N N 71.592 -8.828 -14.771 4.476 0.522 6.720 H541 BGD 87 BGD H542 2H54 H 0 0 N N N 71.591 -7.290 -15.624 5.470 -0.048 5.491 H542 BGD 88 # # 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 BGD C1 O2 DOUB N N 1 BGD C1 C17 SING N N 2 BGD C1 N18 SING N N 3 BGD C3 C4 SING N N 4 BGD C3 C17 SING N N 5 BGD C3 H31 SING N N 6 BGD C3 H32 SING N N 7 BGD C4 C5 SING N N 8 BGD C4 H41A SING N N 9 BGD C4 H42A SING N N 10 BGD C5 O6 DOUB N N 11 BGD C5 O7 SING N N 12 BGD O7 H7 SING N N 13 BGD C8 O9 DOUB N N 14 BGD C8 C10 SING N N 15 BGD C8 N16 SING N N 16 BGD C10 C11 DOUB Y N 17 BGD C10 C12 SING Y N 18 BGD C11 C13 SING Y N 19 BGD C11 H11 SING N N 20 BGD C12 C14 DOUB Y N 21 BGD C12 H12 SING N N 22 BGD C13 C15 DOUB Y N 23 BGD C13 H13 SING N N 24 BGD C14 C15 SING Y N 25 BGD C14 H14 SING N N 26 BGD C15 H15 SING N N 27 BGD N16 C17 SING N N 28 BGD N16 H16 SING N N 29 BGD C17 H17 SING N N 30 BGD N18 C19 SING N N 31 BGD N18 H18 SING N N 32 BGD C19 C20 SING N N 33 BGD C19 C22 SING N N 34 BGD C19 H19 SING N N 35 BGD C20 O21 DOUB N N 36 BGD C20 N36 SING N N 37 BGD C22 C23 SING N N 38 BGD C22 H221 SING N N 39 BGD C22 H222 SING N N 40 BGD C23 C24 DOUB Y N 41 BGD C23 C26 SING Y N 42 BGD C24 C25 SING Y N 43 BGD C24 H24 SING N N 44 BGD C25 C28 DOUB Y N 45 BGD C25 H25 SING N N 46 BGD C26 C27 DOUB Y N 47 BGD C26 H26 SING N N 48 BGD C27 C28 SING Y N 49 BGD C27 H27 SING N N 50 BGD C28 C29 SING N N 51 BGD C29 F30 SING N N 52 BGD C29 F31 SING N N 53 BGD C29 P32 SING N N 54 BGD P32 O33 DOUB N N 55 BGD P32 O34 SING N N 56 BGD P32 O35 SING N N 57 BGD O34 H34 SING N N 58 BGD O35 H35 SING N N 59 BGD N36 C37 SING N N 60 BGD N36 H36 SING N N 61 BGD C37 C38 SING N N 62 BGD C37 C52 SING N N 63 BGD C37 H37 SING N N 64 BGD C38 C39 SING N N 65 BGD C38 H381 SING N N 66 BGD C38 H382 SING N N 67 BGD C39 C40 DOUB Y N 68 BGD C39 C42 SING Y N 69 BGD C40 C41 SING Y N 70 BGD C40 H40 SING N N 71 BGD C41 C44 DOUB Y N 72 BGD C41 H41 SING N N 73 BGD C42 C43 DOUB Y N 74 BGD C42 H42 SING N N 75 BGD C43 C44 SING Y N 76 BGD C43 H43 SING N N 77 BGD C44 C45 SING N N 78 BGD C45 F46 SING N N 79 BGD C45 F47 SING N N 80 BGD C45 P48 SING N N 81 BGD P48 O49 DOUB N N 82 BGD P48 O50 SING N N 83 BGD P48 O51 SING N N 84 BGD O50 H50 SING N N 85 BGD O51 H51 SING N N 86 BGD C52 O53 DOUB N N 87 BGD C52 N54 SING N N 88 BGD N54 H541 SING N N 89 BGD N54 H542 SING N N 90 # # 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 BGD SMILES ACDLabs 10.04 "FC(F)(c1ccc(cc1)CC(C(=O)N)NC(=O)C(NC(=O)C(NC(=O)c2ccccc2)CCC(=O)O)Cc3ccc(cc3)C(F)(F)P(=O)(O)O)P(=O)(O)O" BGD SMILES_CANONICAL CACTVS 3.341 "NC(=O)[C@H](Cc1ccc(cc1)C(F)(F)[P](O)(O)=O)NC(=O)[C@H](Cc2ccc(cc2)C(F)(F)[P](O)(O)=O)NC(=O)[C@H](CCC(O)=O)NC(=O)c3ccccc3" BGD SMILES CACTVS 3.341 "NC(=O)[CH](Cc1ccc(cc1)C(F)(F)[P](O)(O)=O)NC(=O)[CH](Cc2ccc(cc2)C(F)(F)[P](O)(O)=O)NC(=O)[CH](CCC(O)=O)NC(=O)c3ccccc3" BGD SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 "c1ccc(cc1)C(=O)N[C@@H](CCC(=O)O)C(=O)N[C@@H](Cc2ccc(cc2)C(F)(F)P(=O)(O)O)C(=O)N[C@@H](Cc3ccc(cc3)C(F)(F)P(=O)(O)O)C(=O)N" BGD SMILES "OpenEye OEToolkits" 1.5.0 "c1ccc(cc1)C(=O)NC(CCC(=O)O)C(=O)NC(Cc2ccc(cc2)C(F)(F)P(=O)(O)O)C(=O)NC(Cc3ccc(cc3)C(F)(F)P(=O)(O)O)C(=O)N" BGD InChI InChI 1.03 "InChI=1S/C32H34F4N4O12P2/c33-31(34,53(47,48)49)21-10-6-18(7-11-21)16-24(27(37)43)39-30(46)25(17-19-8-12-22(13-9-19)32(35,36)54(50,51)52)40-29(45)23(14-15-26(41)42)38-28(44)20-4-2-1-3-5-20/h1-13,23-25H,14-17H2,(H2,37,43)(H,38,44)(H,39,46)(H,40,45)(H,41,42)(H2,47,48,49)(H2,50,51,52)/t23-,24-,25-/m0/s1" BGD InChIKey InChI 1.03 UJIWNECQGQOIKP-SDHOMARFSA-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 BGD "SYSTEMATIC NAME" ACDLabs 10.04 "N-(phenylcarbonyl)-L-alpha-glutamyl-4-[difluoro(phosphono)methyl]-L-phenylalanyl-4-[difluoro(phosphono)methyl]-L-phenylalaninamide" BGD "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "(4S)-5-[[(2S)-1-[[(2S)-1-amino-3-[4-(difluoro-phosphono-methyl)phenyl]-1-oxo-propan-2-yl]amino]-3-[4-(difluoro-phosphono-methyl)phenyl]-1-oxo-propan-2-yl]amino]-4-benzamido-5-oxo-pentanoic 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 BGD "Create component" 2002-05-16 RCSB BGD "Modify descriptor" 2011-06-04 RCSB BGD "Modify synonyms" 2021-03-01 PDBE # _pdbx_chem_comp_synonyms.ordinal 1 _pdbx_chem_comp_synonyms.comp_id BGD _pdbx_chem_comp_synonyms.name "4-BENZOYLAMINO-4-{1-{1-CARBAMOYL-2-[4-(DIFLUORO-PHOSPHONO-METHYL)-PHENYL]-ETHYLCARBAMOYL}-2-[4-(DIFLUORO-PHOSPHONO-METHYL)-PHENYL]-ETHYLCARBAMOYL}-BUTYRIC ACID" _pdbx_chem_comp_synonyms.provenance ? _pdbx_chem_comp_synonyms.type ? ##