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                    2008-10-14 
_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 InChI            InChI                1.02b 
;InChI=1/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/f/h38-41,47-48,50-51H,37H2
;
BGD InChIKey         InChI                1.02b UJIWNECQGQOIKP-SWQDJFJZDE 
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 
# 
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" 
# 
