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 2013-01-18 _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 # 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 VPF C1 C1 C 0 1 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 12.707 47.473 -1.308 8.182 -2.869 0.328 O1 SIN 2 VPF O2 O2 O 0 1 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 13.157 46.826 0.880 7.671 -0.619 -0.151 C2 SIN 4 VPF C3 C3 C 0 1 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 13.757 45.416 2.906 5.282 0.032 -0.282 C4 SIN 6 VPF O3 O3 O 0 1 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 12.888 44.418 2.725 3.951 -0.170 -0.234 N VAL 8 VPF CA CA C 0 1 N N S 12.119 43.875 3.841 3.031 0.945 -0.469 CA VAL 9 VPF C C C 0 1 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 13.531 41.965 3.496 1.256 -0.459 0.200 O VAL 11 VPF CB CB C 0 1 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 10.301 42.700 2.445 2.236 -0.188 -2.549 CG1 VAL 13 VPF CG2 CG2 C 0 1 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 13.130 42.229 5.504 1.049 1.659 0.827 N PRO 15 VPF CA1 CA1 C 0 1 N N S 13.559 40.890 5.930 -0.193 1.508 1.599 CA PRO 16 VPF C5 C5 C 0 1 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 11.396 39.965 5.442 -1.044 0.686 -0.442 O PRO 18 VPF CB1 CB1 C 0 1 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 12.730 42.109 7.789 0.129 3.855 1.099 CG PRO 20 VPF CD CD C 0 1 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 10.631 39.738 5.399 -4.526 -2.485 -0.197 O3 XPH 22 VPF P P P 0 1 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 11.593 39.336 3.145 -2.377 -2.274 1.110 O2 XPH 24 VPF CA2 CA2 C 0 1 N N S 12.629 37.787 4.706 -3.530 0.068 0.404 CA XPH 25 VPF CB2 CB2 C 0 1 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 12.751 37.887 2.044 -5.880 0.218 -0.375 CG XPH 27 VPF CD2 CD2 C 0 1 Y 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 13.538 38.511 -0.188 -6.877 0.142 -2.550 CE2 XPH 29 VPF CZ CZ C 0 1 Y 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 11.510 39.496 0.670 -7.677 -1.301 -0.815 CE1 XPH 31 VPF CD1 CD1 C 0 1 Y 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 13.193 38.631 5.060 -2.508 0.720 1.225 N XPH 33 VPF OGG OGG O 0 1 N Y 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 15.067 48.306 -1.497 10.510 -2.333 0.196 HO2 SIN 35 VPF H21 H21 H 0 1 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 12.347 46.120 0.645 7.840 -0.213 -1.148 H22 SIN 37 VPF H31 H31 H 0 1 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 15.080 46.748 1.890 6.060 -1.521 0.958 H32 SIN 39 VPF H H H 0 1 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 12.203 44.559 4.698 3.460 1.862 -0.064 HA VAL 41 VPF HB HB H 0 1 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 9.221 42.651 2.242 1.289 -0.418 -2.062 HG11 VAL 43 VPF HG12 HG12 H 0 0 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 10.651 41.722 2.806 2.941 -1.001 -2.375 HG13 VAL 45 VPF HG21 HG21 H 0 0 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 10.154 42.454 5.122 2.210 3.173 -1.790 HG22 VAL 47 VPF HG23 HG23 H 0 0 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 14.568 40.686 5.542 -0.023 0.848 2.450 HA PRO 49 VPF HB2 HB2 H 0 1 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 14.663 41.260 7.775 -0.245 3.080 3.112 HB3 PRO 51 VPF HG2 HG2 H 0 1 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 13.016 42.572 8.745 0.331 4.825 1.554 HG3 PRO 53 VPF HD2 HD2 H 0 1 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 11.940 43.666 6.538 1.878 3.364 -0.115 HD3 PRO 55 VPF HOP2 HOP2 H 0 0 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 12.421 36.997 5.443 -3.230 0.101 -0.644 HA XPH 57 VPF HB1 HB1 H 0 1 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 12.239 36.233 3.270 -4.729 1.858 0.361 HB2 XPH 59 VPF HD21 HD21 H 0 0 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 14.271 38.408 -0.974 -6.929 0.499 -3.568 HE2 XPH 61 VPF HZ HZ H 0 1 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 10.666 40.159 0.548 -8.354 -2.073 -0.478 HE1 XPH 63 VPF HD1 HD1 H 0 1 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 14.190 38.560 5.092 -2.715 0.992 2.133 H XPH 65 VPF H1 H1 H 0 1 N Y 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 #