data_VPF
# 
_chem_comp.id                                    VPF 
_chem_comp.name                                  "N-(3-carboxypropanoyl)-L-valyl-N-[(1S)-2-phenyl-1-phosphonoethyl]-L-prolinamide" 
_chem_comp.type                                  peptide-like 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C22 H32 N3 O8 P" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         ? 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2012-02-10 
_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                        497.479 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     VPF 
_chem_comp.pdbx_model_coordinates_details        "not provided" 
_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        3UFA 
_chem_comp.pdbx_subcomponent_list                "SIN VAL PRO XPH" 
_chem_comp.pdbx_processing_site                  PDBJ 
_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 
VPF C1   C1   C 0 1 N N N N N N 13.607 47.492 -0.435 8.618  -1.767 0.091  C1   SIN 1  
VPF O1   O1   O 0 1 N N N N N N 12.707 47.473 -1.308 8.182  -2.869 0.328  O1   SIN 2  
VPF O2   O2   O 0 1 N N N N N N 14.957 47.989 -0.608 9.944  -1.566 0.038  O2   SIN 3  
VPF C2   C2   C 0 1 N N N N N N 13.157 46.826 0.880  7.671  -0.619 -0.151 C2   SIN 4  
VPF C3   C3   C 0 1 N N N N N N 14.269 46.049 1.636  6.228  -1.115 -0.040 C3   SIN 5  
VPF C4   C4   C 0 1 N N N N N N 13.757 45.416 2.906  5.282  0.032  -0.282 C4   SIN 6  
VPF O3   O3   O 0 1 N N N N N N 13.817 46.057 3.965  5.719  1.138  -0.520 O3   SIN 7  
VPF N    N    N 0 1 N N N N N N 12.888 44.418 2.725  3.951  -0.170 -0.234 N    VAL 8  
VPF CA   CA   C 0 1 N N S N N N 12.119 43.875 3.841  3.031  0.945  -0.469 CA   VAL 9  
VPF C    C    C 0 1 N N N N N N 12.730 42.527 4.250  1.715  0.664  0.209  C    VAL 10 
VPF O    O    O 0 1 N N N N N N 13.531 41.965 3.496  1.256  -0.459 0.200  O    VAL 11 
VPF CB   CB   C 0 1 N N N N N N 10.567 43.744 3.491  2.804  1.111  -1.973 CB   VAL 12 
VPF CG1  CG1  C 0 1 N N N N N N 10.301 42.700 2.445  2.236  -0.188 -2.549 CG1  VAL 13 
VPF CG2  CG2  C 0 1 N N N N N N 9.795  43.409 4.712  1.815  2.252  -2.217 CG2  VAL 14 
VPF N1   N1   N 0 1 N N N N N N 13.130 42.229 5.504  1.049  1.659  0.827  N    PRO 15 
VPF CA1  CA1  C 0 1 N N S N N N 13.559 40.890 5.930  -0.193 1.508  1.599  CA   PRO 16 
VPF C5   C5   C 0 1 N N N N N N 12.619 39.777 5.461  -1.278 0.942  0.720  C    PRO 17 
VPF O4   O4   O 0 1 N N N N N N 11.396 39.965 5.442  -1.044 0.686  -0.442 O    PRO 18 
VPF CB1  CB1  C 0 1 N N N N N N 13.637 41.019 7.459  -0.598 2.913  2.094  CB   PRO 19 
VPF CG   CG   C 0 1 N N N N N N 12.730 42.109 7.789  0.129  3.855  1.099  CG   PRO 20 
VPF CD   CD   C 0 1 N N N N N N 12.867 43.089 6.673  1.448  3.078  0.845  CD   PRO 21 
VPF O2P  O2P  O 0 1 N N N N N N 10.631 39.738 5.399  -4.526 -2.485 -0.197 O3   XPH 22 
VPF P    P    P 0 1 N N N N N N 11.350 38.629 4.537  -3.715 -1.668 0.928  P    XPH 23 
VPF O1P  O1P  O 0 1 N N N N N N 11.593 39.336 3.145  -2.377 -2.274 1.110  O2   XPH 24 
VPF CA2  CA2  C 0 1 N N S N N N 12.629 37.787 4.706  -3.530 0.068  0.404  CA   XPH 25 
VPF CB2  CB2  C 0 1 N N N N N N 12.914 37.099 3.338  -4.864 0.798  0.576  CB   XPH 26 
VPF CG3  CG3  C 0 1 Y N N N N N 12.751 37.887 2.044  -5.880 0.218  -0.375 CG   XPH 27 
VPF CD2  CD2  C 0 1 Y N N N N N 13.681 37.768 1.019  -5.946 0.674  -1.678 CD2  XPH 28 
VPF CE2  CE2  C 0 1 Y N N N N N 13.538 38.511 -0.188 -6.877 0.142  -2.550 CE2  XPH 29 
VPF CZ   CZ   C 0 1 Y N N N N N 12.456 39.368 -0.355 -7.743 -0.845 -2.119 CZ   XPH 30 
VPF CE1  CE1  C 0 1 Y N N N N N 11.510 39.496 0.670  -7.677 -1.301 -0.815 CE1  XPH 31 
VPF CD1  CD1  C 0 1 Y N N N N N 11.662 38.757 1.864  -6.742 -0.773 0.055  CD1  XPH 32 
VPF N2   N2   N 0 1 N N N N N N 13.193 38.631 5.060  -2.508 0.720  1.225  N    XPH 33 
VPF OGG  OGG  O 0 1 N Y N N N N 10.203 37.587 4.233  -4.524 -1.725 2.320  O1   XPH 34 
VPF HO2  HO2  H 0 1 N N N N N N 15.067 48.306 -1.497 10.510 -2.333 0.196  HO2  SIN 35 
VPF H21  H21  H 0 1 N N N N N N 12.776 47.613 1.548  7.846  0.159  0.592  H21  SIN 36 
VPF H22  H22  H 0 1 N N N N N N 12.347 46.120 0.645  7.840  -0.213 -1.148 H22  SIN 37 
VPF H31  H31  H 0 1 N N N N N N 14.659 45.258 0.978  6.054  -1.893 -0.783 H31  SIN 38 
VPF H32  H32  H 0 1 N N N N N N 15.080 46.748 1.890  6.060  -1.521 0.958  H32  SIN 39 
VPF H    H    H 0 1 N N N N N N 12.762 44.036 1.809  3.601  -1.055 -0.044 H    VAL 40 
VPF HA   HA   H 0 1 N N N N N N 12.203 44.559 4.698  3.460  1.862  -0.064 HA   VAL 41 
VPF HB   HB   H 0 1 N N N N N N 10.229 44.719 3.111  3.751  1.340  -2.461 HB   VAL 42 
VPF HG11 HG11 H 0 0 N N N N N N 9.221  42.651 2.242  1.289  -0.418 -2.062 HG11 VAL 43 
VPF HG12 HG12 H 0 0 N N N N N N 10.836 42.963 1.521  2.075  -0.071 -3.621 HG12 VAL 44 
VPF HG13 HG13 H 0 0 N N N N N N 10.651 41.722 2.806  2.941  -1.001 -2.375 HG13 VAL 45 
VPF HG21 HG21 H 0 0 N N N N N N 8.728  43.321 4.459  0.861  2.013  -1.747 HG21 VAL 46 
VPF HG22 HG22 H 0 0 N N N N N N 10.154 42.454 5.122  2.210  3.173  -1.790 HG22 VAL 47 
VPF HG23 HG23 H 0 0 N N N N N N 9.930  44.204 5.461  1.668  2.383  -3.290 HG23 VAL 48 
VPF HA1  HA1  H 0 1 N N N N N N 14.568 40.686 5.542  -0.023 0.848  2.450  HA   PRO 49 
VPF HB2  HB2  H 0 1 N N N N N N 13.313 40.086 7.943  -1.678 3.047  2.033  HB2  PRO 50 
VPF HB3  HB3  H 0 1 N N N N N N 14.663 41.260 7.775  -0.245 3.080  3.112  HB3  PRO 51 
VPF HG2  HG2  H 0 1 N N N N N N 11.695 41.742 7.854  -0.444 3.969  0.179  HG2  PRO 52 
VPF HG3  HG3  H 0 1 N N N N N N 13.016 42.572 8.745  0.331  4.825  1.554  HG3  PRO 53 
VPF HD2  HD2  H 0 1 N N N N N N 13.705 43.778 6.853  2.160  3.262  1.650  HD2  PRO 54 
VPF HD3  HD3  H 0 1 N N N N N N 11.940 43.666 6.538  1.878  3.364  -0.115 HD3  PRO 55 
VPF HOP2 HOP2 H 0 0 N N N N N N 11.276 40.354 5.725  -4.061 -2.559 -1.042 H3   XPH 56 
VPF HA2  HA2  H 0 1 N N N N N N 12.421 36.997 5.443  -3.230 0.101  -0.644 HA   XPH 57 
VPF HB1  HB1  H 0 1 N N N N N N 13.957 36.750 3.369  -5.215 0.677  1.600  HB3  XPH 58 
VPF HB21 HB21 H 0 0 N N N N N N 12.239 36.233 3.270  -4.729 1.858  0.361  HB2  XPH 59 
VPF HD21 HD21 H 0 0 N N N N N N 14.524 37.103 1.139  -5.269 1.445  -2.015 HD2  XPH 60 
VPF HE2  HE2  H 0 1 N N N N N N 14.271 38.408 -0.974 -6.929 0.499  -3.568 HE2  XPH 61 
VPF HZ   HZ   H 0 1 N N N N N N 12.346 39.932 -1.270 -8.471 -1.261 -2.800 HG   XPH 62 
VPF HE1  HE1  H 0 1 N N N N N N 10.666 40.159 0.548  -8.354 -2.073 -0.478 HE1  XPH 63 
VPF HD1  HD1  H 0 1 N N N N N N 10.930 38.862 2.651  -6.688 -1.132 1.072  HD1  XPH 64 
VPF HN2  HN2  H 0 1 N N N N N N 14.190 38.560 5.092  -2.715 0.992  2.133  H    XPH 65 
VPF H1   H1   H 0 1 N Y N N N N 9.956  37.646 3.318  -4.132 -1.191 3.024  H1   XPH 66 
# 
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 
VPF C1  O1   DOUB N N 1  
VPF C1  O2   SING N N 2  
VPF C1  C2   SING N N 3  
VPF C2  C3   SING N N 4  
VPF C3  C4   SING N N 5  
VPF C4  O3   DOUB N N 6  
VPF C4  N    SING N N 7  
VPF N   CA   SING N N 8  
VPF CA  C    SING N N 9  
VPF CA  CB   SING N N 10 
VPF C   O    DOUB N N 11 
VPF C   N1   SING N N 12 
VPF CB  CG1  SING N N 13 
VPF CB  CG2  SING N N 14 
VPF N1  CA1  SING N N 15 
VPF N1  CD   SING N N 16 
VPF CA1 C5   SING N N 17 
VPF CA1 CB1  SING N N 18 
VPF C5  O4   DOUB N N 19 
VPF C5  N2   SING N N 20 
VPF CB1 CG   SING N N 21 
VPF CG  CD   SING N N 22 
VPF N2  CA2  SING N N 23 
VPF CA2 HA2  SING N N 24 
VPF CA2 CB2  SING N N 25 
VPF CA2 P    SING N N 26 
VPF CB2 CG3  SING N N 27 
VPF CG3 CD1  DOUB Y N 28 
VPF CG3 CD2  SING Y N 29 
VPF CD1 CE1  SING Y N 30 
VPF CD2 CE2  DOUB Y N 31 
VPF CE1 CZ   DOUB Y N 32 
VPF CE2 CZ   SING Y N 33 
VPF O1P P    DOUB N N 34 
VPF P   O2P  SING N N 35 
VPF P   OGG  SING N N 36 
VPF O2  HO2  SING N N 37 
VPF C2  H21  SING N N 38 
VPF C2  H22  SING N N 39 
VPF C3  H31  SING N N 40 
VPF C3  H32  SING N N 41 
VPF N   H    SING N N 42 
VPF CA  HA   SING N N 43 
VPF CB  HB   SING N N 44 
VPF CG1 HG11 SING N N 45 
VPF CG1 HG12 SING N N 46 
VPF CG1 HG13 SING N N 47 
VPF CG2 HG21 SING N N 48 
VPF CG2 HG22 SING N N 49 
VPF CG2 HG23 SING N N 50 
VPF CA1 HA1  SING N N 51 
VPF CB1 HB2  SING N N 52 
VPF CB1 HB3  SING N N 53 
VPF CG  HG2  SING N N 54 
VPF CG  HG3  SING N N 55 
VPF CD  HD2  SING N N 56 
VPF CD  HD3  SING N N 57 
VPF N2  HN2  SING N N 58 
VPF CB2 HB1  SING N N 59 
VPF CB2 HB21 SING N N 60 
VPF CD1 HD1  SING N N 61 
VPF CD2 HD21 SING N N 62 
VPF CE1 HE1  SING N N 63 
VPF CE2 HE2  SING N N 64 
VPF CZ  HZ   SING N N 65 
VPF O2P HOP2 SING N N 66 
VPF OGG H1   SING N N 67 
# 
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 
VPF SMILES           ACDLabs              12.01 "O=C(NC(Cc1ccccc1)P(=O)(O)O)C2N(C(=O)C(NC(=O)CCC(=O)O)C(C)C)CCC2"                                                                                                                                                           
VPF InChI            InChI                1.03  "InChI=1S/C22H32N3O8P/c1-14(2)20(23-17(26)10-11-19(27)28)22(30)25-12-6-9-16(25)21(29)24-18(34(31,32)33)13-15-7-4-3-5-8-15/h3-5,7-8,14,16,18,20H,6,9-13H2,1-2H3,(H,23,26)(H,24,29)(H,27,28)(H2,31,32,33)/t16-,18-,20-/m0/s1" 
VPF InChIKey         InChI                1.03  KPGFVOVOBVGIMY-QRFRQXIXSA-N                                                                                                                                                                                                 
VPF SMILES_CANONICAL CACTVS               3.370 "CC(C)[C@H](NC(=O)CCC(O)=O)C(=O)N1CCC[C@H]1C(=O)N[C@H](Cc2ccccc2)[P](O)(O)=O"                                                                                                                                               
VPF SMILES           CACTVS               3.370 "CC(C)[CH](NC(=O)CCC(O)=O)C(=O)N1CCC[CH]1C(=O)N[CH](Cc2ccccc2)[P](O)(O)=O"                                                                                                                                                  
VPF SMILES_CANONICAL "OpenEye OEToolkits" 1.7.6 "CC(C)[C@@H](C(=O)N1CCC[C@H]1C(=O)N[C@H](Cc2ccccc2)P(=O)(O)O)NC(=O)CCC(=O)O"                                                                                                                                                
VPF SMILES           "OpenEye OEToolkits" 1.7.6 "CC(C)C(C(=O)N1CCCC1C(=O)NC(Cc2ccccc2)P(=O)(O)O)NC(=O)CCC(=O)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 
VPF "SYSTEMATIC NAME" ACDLabs              12.01 "N-(3-carboxypropanoyl)-L-valyl-N-[(1S)-2-phenyl-1-phosphonoethyl]-L-prolinamide"                                                                         
VPF "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.7.6 "4-[[(2S)-3-methyl-1-oxidanylidene-1-[(2S)-2-[[(1S)-2-phenyl-1-phosphono-ethyl]carbamoyl]pyrrolidin-1-yl]butan-2-yl]amino]-4-oxidanylidene-butanoic 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 
VPF "Create component" 2012-02-10 PDBJ 
VPF "Initial release"  2013-01-18 RCSB 
VPF "Modify PCM"       2024-09-27 PDBE 
# 
_pdbx_chem_comp_pcm.pcm_id                             1 
_pdbx_chem_comp_pcm.comp_id                            VPF 
_pdbx_chem_comp_pcm.modified_residue_id                SER 
_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               P 
_pdbx_chem_comp_pcm.modified_residue_id_linking_atom   OG 
_pdbx_chem_comp_pcm.uniprot_specific_ptm_accession     ? 
_pdbx_chem_comp_pcm.uniprot_generic_ptm_accession      ? 
# 
