data_BFO
# 
_chem_comp.id                                    BFO 
_chem_comp.name                                  "benzyl N-[(naphthalen-2-ylmethoxy)carbonyl]-L-alanyl-N~5~-[(2R,3S,4S)-3-formyl-2-hydroxy-4-methylhexanoyl]-L-ornithinate" 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C35 H43 N3 O8" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         ? 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2011-08-24 
_chem_comp.pdbx_modified_date                    2024-09-27 
_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                        633.731 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     BFO 
_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        3TDD 
_chem_comp.pdbx_subcomponent_list                ? 
_chem_comp.pdbx_processing_site                  RCSB 
_chem_comp.pdbx_pcm                              Y 
# 
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.pdbx_backbone_atom_flag 
_chem_comp_atom.pdbx_n_terminal_atom_flag 
_chem_comp_atom.pdbx_c_terminal_atom_flag 
_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 
BFO C1   C1   C 0 1 Y N N N N N 16.692 -143.574 14.765 9.369  -0.088 -0.866 C1   BFO 1  
BFO C2   C2   C 0 1 Y N N N N N 17.333 -144.148 13.631 8.149  0.197  -1.397 C2   BFO 2  
BFO C3   C3   C 0 1 Y N N N N N 16.825 -145.348 13.009 7.209  0.936  -0.681 C3   BFO 3  
BFO C4   C4   C 0 1 N N N N N N 17.575 -145.880 11.731 5.868  1.233  -1.302 C4   BFO 4  
BFO O5   O5   O 0 1 N N N N N N 18.141 -144.663 11.155 4.935  0.172  -0.970 O5   BFO 5  
BFO C6   C6   C 0 1 N N N N N N 18.864 -144.569 10.001 3.683  0.286  -1.452 C6   BFO 6  
BFO O7   O7   O 0 1 N N N N N N 19.159 -145.506 9.226  3.379  1.246  -2.132 O7   BFO 7  
BFO N8   N8   N 0 1 N N N N N N 19.196 -143.224 9.874  2.767  -0.665 -1.180 N8   BFO 8  
BFO C9   C9   C 0 1 N N S N N N 19.964 -142.447 8.868  1.405  -0.541 -1.704 C9   BFO 9  
BFO C10  C10  C 0 1 N N N N N N 19.689 -142.940 7.397  1.352  -1.104 -3.126 C10  BFO 10 
BFO C11  C11  C 0 1 N N N N N N 19.595 -140.963 9.041  0.455  -1.312 -0.823 C11  BFO 11 
BFO O12  O12  O 0 1 N N N N N N 20.474 -140.098 9.138  0.875  -1.906 0.147  O12  BFO 12 
BFO N13  N13  N 0 1 N N N N N N 18.248 -140.655 9.076  -0.860 -1.340 -1.114 N13  BFO 13 
BFO C14  C14  C 0 1 N N S N N N 17.514 -139.888 10.135 -1.783 -2.089 -0.257 C14  BFO 14 
BFO C15  C15  C 0 1 N N N N N N 17.812 -138.385 10.121 -1.805 -3.534 -0.685 C15  BFO 15 
BFO O16  O16  O 0 1 N N N N N N 17.625 -137.772 9.069  -1.120 -3.901 -1.610 O16  BFO 16 
BFO O17  O17  O 0 1 N N N N N N 18.240 -137.781 11.273 -2.585 -4.414 -0.038 O17  BFO 17 
BFO C18  C18  C 0 1 N N N N N N 18.454 -136.320 11.179 -2.556 -5.789 -0.505 C18  BFO 18 
BFO C19  C19  C 0 1 Y N N N N N 19.898 -135.843 10.950 -3.487 -6.624 0.335  C19  BFO 19 
BFO C20  C20  C 0 1 Y N N N N N 20.681 -135.413 12.061 -4.810 -6.770 -0.038 C20  BFO 20 
BFO C21  C21  C 0 1 Y N N N N N 22.024 -134.956 11.872 -5.665 -7.536 0.732  C21  BFO 21 
BFO C22  C22  C 0 1 Y N N N N N 22.587 -134.929 10.561 -5.196 -8.158 1.875  C22  BFO 22 
BFO C23  C23  C 0 1 Y N N N N N 21.809 -135.355 9.447  -3.873 -8.013 2.247  C23  BFO 23 
BFO C24  C24  C 0 1 Y N N N N N 20.469 -135.810 9.638  -3.017 -7.250 1.475  C24  BFO 24 
BFO C25  C25  C 0 1 N N N N N N 17.607 -140.542 11.569 -3.189 -1.499 -0.384 C25  BFO 25 
BFO C26  C26  C 0 1 N N N N N N 16.260 -140.270 12.358 -3.195 -0.072 0.167  C26  BFO 26 
BFO C27  C27  C 0 1 N N N N N N 15.103 -141.294 11.983 -4.601 0.518  0.041  C27  BFO 27 
BFO N28  N28  N 0 1 N N N N N N 13.728 -140.712 12.032 -4.606 1.885  0.568  N28  BFO 28 
BFO C29  C29  C 0 1 N N N N N N 12.887 -140.765 13.165 -5.744 2.606  0.559  C29  BFO 29 
BFO O30  O30  O 0 1 N N N N N N 13.199 -141.296 14.229 -6.764 2.124  0.116  O30  BFO 30 
BFO C31  C31  C 0 1 N N R N N N 11.512 -140.115 13.090 -5.749 4.012  1.102  C31  BFO 31 
BFO O32  O32  O 0 1 N N N N N N 10.724 -140.730 12.068 -7.084 4.522  1.092  O32  BFO 32 
BFO C33  C33  C 0 1 N N S N N N 11.597 -138.558 12.840 -4.858 4.899  0.229  C33  BFO 33 
BFO C34  C34  C 0 1 N N S N N N 10.269 -137.755 13.122 -4.764 6.294  0.850  C34  BFO 34 
BFO C35  C35  C 0 1 N N N N N N 9.749  -137.975 14.578 -4.161 6.189  2.252  C35  BFO 35 
BFO C36  C36  C 0 1 N N N N N N 10.540 -136.223 12.841 -3.872 7.181  -0.023 C36  BFO 36 
BFO C37  C37  C 0 1 N N N N N N 9.333  -135.279 13.062 -3.878 8.608  0.528  C37  BFO 37 
BFO C38  C38  C 0 1 N N N N N N 12.021 -138.291 11.402 -5.451 5.002  -1.152 C38  BFO 38 
BFO O39  O39  O 0 1 N N N N N N 13.113 -137.813 11.104 -4.820 4.624  -2.110 O39  BFO 39 
BFO C40  C40  C 0 1 Y N N N N N 15.646 -145.974 13.569 7.483  1.393  0.571  C40  BFO 40 
BFO C41  C41  C 0 1 Y N N N N N 14.985 -145.384 14.730 8.732  1.117  1.154  C41  BFO 41 
BFO C42  C42  C 0 1 Y N N N N N 13.810 -145.979 15.309 9.051  1.572  2.444  C42  BFO 42 
BFO C43  C43  C 0 1 Y N N N N N 13.166 -145.372 16.454 10.271 1.287  2.976  C43  BFO 43 
BFO C44  C44  C 0 1 Y N N N N N 13.691 -144.180 17.033 11.212 0.549  2.260  C44  BFO 44 
BFO C45  C45  C 0 1 Y N N N N N 14.867 -143.583 16.469 10.937 0.093  1.007  C45  BFO 45 
BFO C46  C46  C 0 1 Y N N N N N 15.524 -144.172 15.331 9.688  0.367  0.425  C46  BFO 46 
BFO H1   H1   H 0 1 N N N N N N 17.094 -142.673 15.204 10.086 -0.665 -1.431 H1   BFO 47 
BFO H2   H2   H 0 1 N N N N N N 18.217 -143.676 13.228 7.906  -0.154 -2.389 H2   BFO 48 
BFO H4   H4   H 0 1 N N N N N N 18.357 -146.609 11.991 5.492  2.181  -0.919 H4   BFO 49 
BFO H4A  H4A  H 0 1 N N N N N N 16.887 -146.379 11.033 5.976  1.296  -2.385 H4A  BFO 50 
BFO HN8  HN8  H 0 1 N N N N N N 18.842 -142.660 10.620 3.010  -1.431 -0.637 HN8  BFO 51 
BFO H9   H9   H 0 1 N N N N N N 21.041 -142.595 9.034  1.115  0.510  -1.719 H9   BFO 52 
BFO H10  H10  H 0 1 N N N N N N 20.278 -142.336 6.691  1.642  -2.155 -3.112 H10  BFO 53 
BFO H10A H10A H 0 0 N N N N N N 19.978 -143.997 7.305  0.338  -1.012 -3.516 H10A BFO 54 
BFO H10B H10B H 0 0 N N N N N N 18.619 -142.831 7.168  2.039  -0.547 -3.763 H10B BFO 55 
BFO HN13 HN13 H 0 0 N N N N N N 17.700 -140.981 8.306  -1.196 -0.865 -1.890 HN13 BFO 56 
BFO H14  H14  H 0 1 N N N N N N 16.452 -139.967 9.859  -1.453 -2.022 0.779  H14  BFO 57 
BFO H18  H18  H 0 1 N N N N N N 17.856 -135.960 10.329 -2.873 -5.826 -1.547 H18  BFO 58 
BFO H18A H18A H 0 0 N N N N N N 18.116 -135.882 12.130 -1.541 -6.180 -0.420 H18A BFO 59 
BFO H20  H20  H 0 1 N N N N N N 20.257 -135.432 13.054 -5.177 -6.285 -0.930 H20  BFO 60 
BFO H21  H21  H 0 1 N N N N N N 22.610 -134.632 12.720 -6.699 -7.650 0.442  H21  BFO 61 
BFO H22  H22  H 0 1 N N N N N N 23.601 -134.586 10.414 -5.864 -8.756 2.477  H22  BFO 62 
BFO H23  H23  H 0 1 N N N N N N 22.234 -135.334 8.454  -3.507 -8.498 3.140  H23  BFO 63 
BFO H24  H24  H 0 1 N N N N N N 19.884 -136.131 8.789  -1.982 -7.140 1.763  H24  BFO 64 
BFO H25  H25  H 0 1 N N N N N N 17.762 -141.626 11.469 -3.484 -1.485 -1.433 H25  BFO 65 
BFO H25A H25A H 0 0 N N N N N N 18.451 -140.101 12.120 -3.892 -2.110 0.183  H25A BFO 66 
BFO H26  H26  H 0 1 N N N N N N 16.466 -140.360 13.435 -2.899 -0.086 1.216  H26  BFO 67 
BFO H26A H26A H 0 0 N N N N N N 15.915 -139.254 12.114 -2.492 0.539  -0.400 H26A BFO 68 
BFO H27  H27  H 0 1 N N N N N N 15.284 -141.648 10.957 -4.896 0.533  -1.009 H27  BFO 69 
BFO H27A H27A H 0 0 N N N N N N 15.143 -142.127 12.700 -5.303 -0.092 0.607  H27A BFO 70 
BFO HN28 HN28 H 0 0 N N N N N N 13.382 -140.257 11.212 -3.789 2.271  0.923  HN28 BFO 71 
BFO H31  H31  H 0 1 N N N N N N 11.031 -140.268 14.067 -5.370 4.009  2.124  H31  BFO 72 
BFO HO32 HO32 H 0 0 N N N N N N 9.870  -140.315 12.033 -7.486 4.554  0.213  HO32 BFO 73 
BFO H33  H33  H 0 1 N N N N N N 12.338 -138.196 13.568 -3.862 4.462  0.165  H33  BFO 74 
BFO H34  H34  H 0 1 N N N N N N 9.478  -138.126 12.453 -5.760 6.732  0.914  H34  BFO 75 
BFO H35  H35  H 0 1 N N N N N N 8.825  -137.398 14.729 -4.094 7.183  2.694  H35  BFO 76 
BFO H35A H35A H 0 0 N N N N N N 9.544  -139.044 14.736 -4.796 5.558  2.874  H35A BFO 77 
BFO H35B H35B H 0 0 N N N N N N 10.512 -137.638 15.295 -3.165 5.752  2.188  H35B BFO 78 
BFO H36  H36  H 0 1 N N N N N N 11.342 -135.899 13.521 -2.854 6.792  -0.015 H36  BFO 79 
BFO H36A H36A H 0 0 N N N N N N 10.845 -136.129 11.788 -4.252 7.184  -1.044 H36A BFO 80 
BFO H37  H37  H 0 1 N N N N N N 9.631  -134.244 12.839 -4.896 8.997  0.520  H37  BFO 81 
BFO H37A H37A H 0 0 N N N N N N 8.509  -135.575 12.396 -3.498 8.605  1.550  H37A BFO 82 
BFO H37B H37B H 0 0 N N N N N N 9.001  -135.348 14.108 -3.243 9.240  -0.094 H37B BFO 83 
BFO H38  H38  H 0 1 N Y N N N N 11.330 -138.533 10.608 -6.440 5.415  -1.286 H38  BFO 84 
BFO H40  H40  H 0 1 N N N N N N 15.255 -146.879 13.128 6.744  1.964  1.115  H40  BFO 85 
BFO H42  H42  H 0 1 N N N N N N 13.405 -146.886 14.886 8.333  2.146  3.011  H42  BFO 86 
BFO H43  H43  H 0 1 N N N N N N 12.280 -145.826 16.873 10.514 1.638  3.968  H43  BFO 87 
BFO H44  H44  H 0 1 N N N N N N 13.208 -143.731 17.888 12.172 0.337  2.705  H44  BFO 88 
BFO H45  H45  H 0 1 N N N N N N 15.266 -142.678 16.904 11.676 -0.477 0.464  H45  BFO 89 
# 
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 
BFO C1  C2   DOUB Y N 1  
BFO C1  C46  SING Y N 2  
BFO C2  C3   SING Y N 3  
BFO C3  C4   SING N N 4  
BFO C3  C40  DOUB Y N 5  
BFO C4  O5   SING N N 6  
BFO O5  C6   SING N N 7  
BFO C6  O7   DOUB N N 8  
BFO C6  N8   SING N N 9  
BFO N8  C9   SING N N 10 
BFO C9  C10  SING N N 11 
BFO C9  C11  SING N N 12 
BFO C11 O12  DOUB N N 13 
BFO C11 N13  SING N N 14 
BFO N13 C14  SING N N 15 
BFO C14 C15  SING N N 16 
BFO C14 C25  SING N N 17 
BFO C15 O16  DOUB N N 18 
BFO C15 O17  SING N N 19 
BFO O17 C18  SING N N 20 
BFO C18 C19  SING N N 21 
BFO C19 C20  DOUB Y N 22 
BFO C19 C24  SING Y N 23 
BFO C20 C21  SING Y N 24 
BFO C21 C22  DOUB Y N 25 
BFO C22 C23  SING Y N 26 
BFO C23 C24  DOUB Y N 27 
BFO C25 C26  SING N N 28 
BFO C26 C27  SING N N 29 
BFO C27 N28  SING N N 30 
BFO N28 C29  SING N N 31 
BFO C29 O30  DOUB N N 32 
BFO C29 C31  SING N N 33 
BFO C31 O32  SING N N 34 
BFO C31 C33  SING N N 35 
BFO C33 C34  SING N N 36 
BFO C33 C38  SING N N 37 
BFO C34 C35  SING N N 38 
BFO C34 C36  SING N N 39 
BFO C36 C37  SING N N 40 
BFO C38 O39  DOUB N N 41 
BFO C40 C41  SING Y N 42 
BFO C41 C42  DOUB Y N 43 
BFO C41 C46  SING Y N 44 
BFO C42 C43  SING Y N 45 
BFO C43 C44  DOUB Y N 46 
BFO C44 C45  SING Y N 47 
BFO C45 C46  DOUB Y N 48 
BFO C1  H1   SING N N 49 
BFO C2  H2   SING N N 50 
BFO C4  H4   SING N N 51 
BFO C4  H4A  SING N N 52 
BFO N8  HN8  SING N N 53 
BFO C9  H9   SING N N 54 
BFO C10 H10  SING N N 55 
BFO C10 H10A SING N N 56 
BFO C10 H10B SING N N 57 
BFO N13 HN13 SING N N 58 
BFO C14 H14  SING N N 59 
BFO C18 H18  SING N N 60 
BFO C18 H18A SING N N 61 
BFO C20 H20  SING N N 62 
BFO C21 H21  SING N N 63 
BFO C22 H22  SING N N 64 
BFO C23 H23  SING N N 65 
BFO C24 H24  SING N N 66 
BFO C25 H25  SING N N 67 
BFO C25 H25A SING N N 68 
BFO C26 H26  SING N N 69 
BFO C26 H26A SING N N 70 
BFO C27 H27  SING N N 71 
BFO C27 H27A SING N N 72 
BFO N28 HN28 SING N N 73 
BFO C31 H31  SING N N 74 
BFO O32 HO32 SING N N 75 
BFO C33 H33  SING N N 76 
BFO C34 H34  SING N N 77 
BFO C35 H35  SING N N 78 
BFO C35 H35A SING N N 79 
BFO C35 H35B SING N N 80 
BFO C36 H36  SING N N 81 
BFO C36 H36A SING N N 82 
BFO C37 H37  SING N N 83 
BFO C37 H37A SING N N 84 
BFO C37 H37B SING N N 85 
BFO C38 H38  SING N N 86 
BFO C40 H40  SING N N 87 
BFO C42 H42  SING N N 88 
BFO C43 H43  SING N N 89 
BFO C44 H44  SING N N 90 
BFO C45 H45  SING N N 91 
# 
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 
BFO SMILES           ACDLabs              12.01 "O=CC(C(C)CC)C(O)C(=O)NCCCC(C(=O)OCc1ccccc1)NC(=O)C(NC(=O)OCc3cc2ccccc2cc3)C"                                                                                                                                                                                                           
BFO InChI            InChI                1.03  "InChI=1S/C35H43N3O8/c1-4-23(2)29(20-39)31(40)33(42)36-18-10-15-30(34(43)45-21-25-11-6-5-7-12-25)38-32(41)24(3)37-35(44)46-22-26-16-17-27-13-8-9-14-28(27)19-26/h5-9,11-14,16-17,19-20,23-24,29-31,40H,4,10,15,18,21-22H2,1-3H3,(H,36,42)(H,37,44)(H,38,41)/t23-,24-,29-,30-,31+/m0/s1" 
BFO InChIKey         InChI                1.03  TYMGDBRPOJUXRJ-WRYWSPJMSA-N                                                                                                                                                                                                                                                             
BFO SMILES_CANONICAL CACTVS               3.370 "CC[C@H](C)[C@H](C=O)[C@@H](O)C(=O)NCCC[C@H](NC(=O)[C@H](C)NC(=O)OCc1ccc2ccccc2c1)C(=O)OCc3ccccc3"                                                                                                                                                                                      
BFO SMILES           CACTVS               3.370 "CC[CH](C)[CH](C=O)[CH](O)C(=O)NCCC[CH](NC(=O)[CH](C)NC(=O)OCc1ccc2ccccc2c1)C(=O)OCc3ccccc3"                                                                                                                                                                                            
BFO SMILES_CANONICAL "OpenEye OEToolkits" 1.7.2 "CC[C@H](C)[C@H](C=O)[C@H](C(=O)NCCC[C@@H](C(=O)OCc1ccccc1)NC(=O)[C@H](C)NC(=O)OCc2ccc3ccccc3c2)O"                                                                                                                                                                                      
BFO SMILES           "OpenEye OEToolkits" 1.7.2 "CCC(C)C(C=O)C(C(=O)NCCCC(C(=O)OCc1ccccc1)NC(=O)C(C)NC(=O)OCc2ccc3ccccc3c2)O"                                                                                                                                                                                                           
# 
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 
BFO "SYSTEMATIC NAME" ACDLabs              12.01 "benzyl N-[(naphthalen-2-ylmethoxy)carbonyl]-L-alanyl-N~5~-[(2R,3S,4S)-3-formyl-2-hydroxy-4-methylhexanoyl]-L-ornithinate"                                      
BFO "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.7.2 "(phenylmethyl) (2S)-5-[[(2R,3S,4S)-3-methanoyl-4-methyl-2-oxidanyl-hexanoyl]amino]-2-[[(2S)-2-(naphthalen-2-ylmethoxycarbonylamino)propanoyl]amino]pentanoate" 
# 
loop_
_pdbx_chem_comp_audit.comp_id 
_pdbx_chem_comp_audit.action_type 
_pdbx_chem_comp_audit.date 
_pdbx_chem_comp_audit.processing_site 
BFO "Create component" 2011-08-24 RCSB 
BFO "Modify PCM"       2024-09-27 PDBE 
# 
_pdbx_chem_comp_pcm.pcm_id                             1 
_pdbx_chem_comp_pcm.comp_id                            BFO 
_pdbx_chem_comp_pcm.modified_residue_id                THR 
_pdbx_chem_comp_pcm.type                               None 
_pdbx_chem_comp_pcm.category                           "Covalent chemical modification" 
_pdbx_chem_comp_pcm.position                           "Amino-acid side chain" 
_pdbx_chem_comp_pcm.polypeptide_position               "Any position" 
_pdbx_chem_comp_pcm.comp_id_linking_atom               C38 
_pdbx_chem_comp_pcm.modified_residue_id_linking_atom   OG1 
_pdbx_chem_comp_pcm.uniprot_specific_ptm_accession     ? 
_pdbx_chem_comp_pcm.uniprot_generic_ptm_accession      ? 
# 
