data_PI4 # _chem_comp.id PI4 _chem_comp.name "1-[2-(8-CARBAMOYLMETHYL-6,9-DIOXO-2-OXA-7,10-DIAZA-BICYCLO[11.2.2]HEPTADECA- 1(16),13(17),14-TRIEN-11-YL)-2-HYDROXY-ETHYL]-PIPERIDINE-2-CARBOXYLIC ACID TERT-BUTYLAMIDE" _chem_comp.type NON-POLYMER _chem_comp.pdbx_type HETAIN _chem_comp.formula "C28 H43 N5 O6" _chem_comp.mon_nstd_parent_comp_id ? _chem_comp.pdbx_synonyms "MACROCYCLIC PEPTIDOMIMETIC INHIBITOR 4" _chem_comp.pdbx_formal_charge 0 _chem_comp.pdbx_initial_date 1999-07-08 _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 545.671 _chem_comp.one_letter_code ? _chem_comp.three_letter_code PI4 _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 1B6L _chem_comp.pdbx_subcomponent_list ? _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 PI4 C1 C1 C 0 1 N N N 6.116 2.819 8.807 1.199 0.648 5.561 C1 PI4 1 PI4 C2 C2 C 0 1 N N N 4.243 3.231 10.445 1.838 -0.123 3.293 C2 PI4 2 PI4 O3 O3 O 0 1 N N N 4.171 4.137 11.275 2.183 0.943 2.832 O3 PI4 3 PI4 C4 C4 C 0 1 N N N 4.789 3.497 9.056 1.979 -0.401 4.768 C4 PI4 4 PI4 N5 N5 N 0 1 N N N 3.877 1.979 10.705 1.317 -1.091 2.486 N5 PI4 5 PI4 C6 C6 C 0 1 N N S 3.311 1.588 12.006 1.206 -0.747 1.052 C6 PI4 6 PI4 C7 C7 C 0 1 N N N 3.967 0.364 12.635 -0.185 -1.080 0.580 C7 PI4 7 PI4 O8 O8 O 0 1 N N N 3.931 -0.732 12.075 -0.442 -2.199 0.189 O8 PI4 8 PI4 C9 C9 C 0 1 N N N 1.814 1.324 11.855 2.229 -1.554 0.251 C9 PI4 9 PI4 C10 C10 C 0 1 N N N 1.077 2.502 11.277 3.621 -1.141 0.654 C10 PI4 10 PI4 O11 O11 O 0 1 N N N 0.512 3.311 12.006 3.779 -0.286 1.499 O11 PI4 11 PI4 N12 N12 N 0 1 N N N 1.098 2.621 9.953 4.691 -1.722 0.075 N12 PI4 12 PI4 N13 N13 N 0 1 N N N 4.556 0.559 13.810 -1.146 -0.135 0.591 N13 PI4 13 PI4 C14 C14 C 0 1 N N S 5.219 -0.533 14.534 -2.502 -0.451 0.134 C14 PI4 14 PI4 C15 C15 C 0 1 N N N 6.735 -0.320 14.535 -3.517 0.208 1.072 C15 PI4 15 PI4 C16 C16 C 0 1 Y N N 7.210 0.441 13.329 -2.886 0.398 2.428 C16 PI4 16 PI4 C17 C17 C 0 1 Y N N 7.333 1.823 13.377 -2.658 -0.696 3.240 C17 PI4 17 PI4 C18 C18 C 0 1 Y N N 7.676 2.546 12.263 -2.074 -0.528 4.481 C18 PI4 18 PI4 C19 C19 C 0 1 Y N N 7.464 -0.206 12.120 -2.535 1.665 2.856 C19 PI4 19 PI4 C20 C20 C 0 1 Y N N 7.811 0.516 10.990 -1.950 1.838 4.096 C20 PI4 20 PI4 C21 C21 C 0 1 Y N N 7.915 1.895 11.074 -1.716 0.740 4.911 C21 PI4 21 PI4 O22 O22 O 0 1 N N N 8.222 2.651 9.971 -1.136 0.908 6.128 O22 PI4 22 PI4 C23 C23 C 0 1 N N N 7.242 3.562 9.512 -0.035 -0.001 6.190 C23 PI4 23 PI4 C24 C24 C 0 1 N N R 4.685 -0.612 15.976 -2.699 0.080 -1.286 C24 PI4 24 PI4 O25 O25 O 0 1 N N N 5.095 0.541 16.717 -3.968 -0.349 -1.784 O25 PI4 25 PI4 C26 C26 C 0 1 N N N 5.172 -1.871 16.673 -1.588 -0.458 -2.190 C26 PI4 26 PI4 N27 N27 N 0 1 N N N 4.423 -3.034 16.141 -1.783 0.043 -3.557 N27 PI4 27 PI4 C28 C28 C 0 1 N N S 5.185 -4.266 16.487 -0.524 -0.188 -4.273 C28 PI4 28 PI4 C29 C29 C 0 1 N N N 4.411 -5.503 16.016 -0.651 0.306 -5.715 C29 PI4 29 PI4 C30 C30 C 0 1 N N N 2.992 -5.579 16.563 -1.758 -0.482 -6.422 C30 PI4 30 PI4 C31 C31 C 0 1 N N N 2.251 -4.280 16.288 -3.054 -0.351 -5.615 C31 PI4 31 PI4 C32 C32 C 0 1 N N N 3.058 -3.080 16.761 -2.801 -0.811 -4.178 C32 PI4 32 PI4 C33 C33 C 0 1 N N N 6.568 -4.231 15.839 0.588 0.559 -3.583 C33 PI4 33 PI4 O34 O34 O 0 1 N N N 6.720 -3.711 14.732 0.327 1.423 -2.774 O34 PI4 34 PI4 C35 C35 C 0 1 N N N 8.962 -4.851 16.086 2.951 1.079 -3.299 C35 PI4 35 PI4 C36 C36 C 0 1 N N N 9.441 -3.485 15.608 4.297 0.586 -3.834 C36 PI4 36 PI4 C37 C37 C 0 1 N N N 9.850 -5.302 17.242 2.933 0.958 -1.774 C37 PI4 37 PI4 C38 C38 C 0 1 N N N 9.093 -5.866 14.956 2.750 2.543 -3.697 C38 PI4 38 PI4 N39 N39 N 0 1 N N N 7.563 -4.780 16.541 1.873 0.266 -3.866 N39 PI4 39 PI4 H11 1H1 H 0 1 N N N 6.089 1.741 9.093 0.886 1.451 4.893 H11 PI4 40 PI4 H12 2H1 H 0 1 N N N 6.319 2.698 7.717 1.834 1.056 6.347 H12 PI4 41 PI4 H41 1H4 H 0 1 N N N 4.857 4.592 8.857 3.032 -0.358 5.046 H41 PI4 42 PI4 H42 2H4 H 0 1 N N N 4.044 3.216 8.274 1.585 -1.392 4.990 H42 PI4 43 PI4 HN5 HN5 H 0 1 N N N 4.026 1.335 9.927 1.036 -1.953 2.832 HN5 PI4 44 PI4 H6 H6 H 0 1 N N N 3.509 2.443 12.693 1.393 0.317 0.917 H6 PI4 45 PI4 H91 1H9 H 0 1 N N N 1.627 0.401 11.257 2.092 -2.616 0.452 H91 PI4 46 PI4 H92 2H9 H 0 1 N N N 1.363 1.004 12.823 2.088 -1.365 -0.812 H92 PI4 47 PI4 H121 1H12 H 0 0 N N N 1.567 1.948 9.346 5.587 -1.456 0.334 H121 PI4 48 PI4 H122 2H12 H 0 0 N N N 0.598 3.419 9.561 4.564 -2.406 -0.600 H122 PI4 49 PI4 H13 H13 H 0 1 N N N 4.500 1.520 14.146 -0.940 0.759 0.904 H13 PI4 50 PI4 H14 H14 H 0 1 N N N 4.996 -1.496 14.019 -2.647 -1.531 0.143 H14 PI4 51 PI4 H151 1H15 H 0 0 N N N 7.070 0.172 15.477 -3.811 1.177 0.668 H151 PI4 52 PI4 H152 2H15 H 0 0 N N N 7.276 -1.289 14.636 -4.396 -0.430 1.165 H152 PI4 53 PI4 H17 H17 H 0 1 N N N 7.153 2.359 14.323 -2.937 -1.684 2.905 H17 PI4 54 PI4 H18 H18 H 0 1 N N N 7.759 3.644 12.322 -1.897 -1.384 5.115 H18 PI4 55 PI4 H19 H19 H 0 1 N N N 7.389 -1.304 12.056 -2.718 2.519 2.221 H19 PI4 56 PI4 H20 H20 H 0 1 N N N 8.002 -0.001 10.034 -1.677 2.828 4.430 H20 PI4 57 PI4 H231 1H23 H 0 0 N N N 7.683 4.356 8.866 0.174 -0.248 7.230 H231 PI4 58 PI4 H232 2H23 H 0 0 N N N 6.860 4.210 10.334 -0.285 -0.910 5.643 H232 PI4 59 PI4 H24 H24 H 0 1 N N N 3.571 -0.645 15.929 -2.663 1.169 -1.275 H24 PI4 60 PI4 H25 H25 H 0 1 N N N 4.765 0.492 17.606 -3.958 -1.316 -1.777 H25 PI4 61 PI4 H261 1H26 H 0 0 N N N 6.276 -2.002 16.591 -1.619 -1.547 -2.195 H261 PI4 62 PI4 H262 2H26 H 0 0 N N N 5.106 -1.794 17.783 -0.621 -0.124 -1.815 H262 PI4 63 PI4 H28 H28 H 0 1 N N N 5.312 -4.315 17.593 -0.298 -1.254 -4.273 H28 PI4 64 PI4 H291 1H29 H 0 0 N N N 4.408 -5.565 14.902 -0.902 1.366 -5.716 H291 PI4 65 PI4 H292 2H29 H 0 0 N N N 4.975 -6.434 16.253 0.293 0.154 -6.237 H292 PI4 66 PI4 H301 1H30 H 0 0 N N N 2.440 -6.464 16.168 -1.909 -0.080 -7.424 H301 PI4 67 PI4 H302 2H30 H 0 0 N N N 2.977 -5.845 17.645 -1.473 -1.532 -6.487 H302 PI4 68 PI4 H311 1H31 H 0 0 N N N 1.968 -4.187 15.213 -3.377 0.689 -5.613 H311 PI4 69 PI4 H312 2H31 H 0 0 N N N 1.228 -4.288 16.732 -3.827 -0.972 -6.066 H312 PI4 70 PI4 H321 1H32 H 0 0 N N N 3.119 -3.049 17.873 -3.727 -0.744 -3.608 H321 PI4 71 PI4 H322 2H32 H 0 0 N N N 2.504 -2.128 16.587 -2.454 -1.844 -4.184 H322 PI4 72 PI4 H361 1H36 H 0 0 N N N 8.792 -3.155 14.763 5.100 1.191 -3.412 H361 PI4 73 PI4 H362 2H36 H 0 0 N N N 9.483 -2.734 16.431 4.441 -0.455 -3.551 H362 PI4 74 PI4 H363 3H36 H 0 0 N N N 10.523 -3.481 15.341 4.310 0.673 -4.921 H363 PI4 75 PI4 H371 1H37 H 0 0 N N N 9.499 -6.301 17.591 3.009 -0.091 -1.492 H371 PI4 76 PI4 H372 2H37 H 0 0 N N N 10.932 -5.298 16.975 3.776 1.509 -1.356 H372 PI4 77 PI4 H373 3H37 H 0 0 N N N 9.892 -4.551 18.065 2.002 1.372 -1.388 H373 PI4 78 PI4 H381 1H38 H 0 0 N N N 8.742 -6.865 15.305 2.763 2.629 -4.783 H381 PI4 79 PI4 H382 2H38 H 0 0 N N N 8.564 -5.535 14.031 1.791 2.894 -3.316 H382 PI4 80 PI4 H383 3H38 H 0 0 N N N 10.128 -5.904 14.544 3.552 3.148 -3.275 H383 PI4 81 PI4 H39 H39 H 0 1 N N N 7.249 -5.150 17.438 2.083 -0.482 -4.446 H39 PI4 82 # # 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 PI4 C1 C4 SING N N 1 PI4 C1 C23 SING N N 2 PI4 C1 H11 SING N N 3 PI4 C1 H12 SING N N 4 PI4 C2 O3 DOUB N N 5 PI4 C2 C4 SING N N 6 PI4 C2 N5 SING N N 7 PI4 C4 H41 SING N N 8 PI4 C4 H42 SING N N 9 PI4 N5 C6 SING N N 10 PI4 N5 HN5 SING N N 11 PI4 C6 C7 SING N N 12 PI4 C6 C9 SING N N 13 PI4 C6 H6 SING N N 14 PI4 C7 O8 DOUB N N 15 PI4 C7 N13 SING N N 16 PI4 C9 C10 SING N N 17 PI4 C9 H91 SING N N 18 PI4 C9 H92 SING N N 19 PI4 C10 O11 DOUB N N 20 PI4 C10 N12 SING N N 21 PI4 N12 H121 SING N N 22 PI4 N12 H122 SING N N 23 PI4 N13 C14 SING N N 24 PI4 N13 H13 SING N N 25 PI4 C14 C15 SING N N 26 PI4 C14 C24 SING N N 27 PI4 C14 H14 SING N N 28 PI4 C15 C16 SING N N 29 PI4 C15 H151 SING N N 30 PI4 C15 H152 SING N N 31 PI4 C16 C17 SING Y N 32 PI4 C16 C19 DOUB Y N 33 PI4 C17 C18 DOUB Y N 34 PI4 C17 H17 SING N N 35 PI4 C18 C21 SING Y N 36 PI4 C18 H18 SING N N 37 PI4 C19 C20 SING Y N 38 PI4 C19 H19 SING N N 39 PI4 C20 C21 DOUB Y N 40 PI4 C20 H20 SING N N 41 PI4 C21 O22 SING N N 42 PI4 O22 C23 SING N N 43 PI4 C23 H231 SING N N 44 PI4 C23 H232 SING N N 45 PI4 C24 O25 SING N N 46 PI4 C24 C26 SING N N 47 PI4 C24 H24 SING N N 48 PI4 O25 H25 SING N N 49 PI4 C26 N27 SING N N 50 PI4 C26 H261 SING N N 51 PI4 C26 H262 SING N N 52 PI4 N27 C28 SING N N 53 PI4 N27 C32 SING N N 54 PI4 C28 C29 SING N N 55 PI4 C28 C33 SING N N 56 PI4 C28 H28 SING N N 57 PI4 C29 C30 SING N N 58 PI4 C29 H291 SING N N 59 PI4 C29 H292 SING N N 60 PI4 C30 C31 SING N N 61 PI4 C30 H301 SING N N 62 PI4 C30 H302 SING N N 63 PI4 C31 C32 SING N N 64 PI4 C31 H311 SING N N 65 PI4 C31 H312 SING N N 66 PI4 C32 H321 SING N N 67 PI4 C32 H322 SING N N 68 PI4 C33 O34 DOUB N N 69 PI4 C33 N39 SING N N 70 PI4 C35 C36 SING N N 71 PI4 C35 C37 SING N N 72 PI4 C35 C38 SING N N 73 PI4 C35 N39 SING N N 74 PI4 C36 H361 SING N N 75 PI4 C36 H362 SING N N 76 PI4 C36 H363 SING N N 77 PI4 C37 H371 SING N N 78 PI4 C37 H372 SING N N 79 PI4 C37 H373 SING N N 80 PI4 C38 H381 SING N N 81 PI4 C38 H382 SING N N 82 PI4 C38 H383 SING N N 83 PI4 N39 H39 SING N N 84 # # 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 PI4 SMILES ACDLabs 10.04 "O=C(NC(C)(C)C)C1N(CCCC1)CC(O)C3NC(=O)C(NC(=O)CCCOc2ccc(cc2)C3)CC(=O)N" PI4 SMILES_CANONICAL CACTVS 3.341 "CC(C)(C)NC(=O)[C@@H]1CCCCN1C[C@@H](O)[C@@H]2Cc3ccc(OCCCC(=O)N[C@@H](CC(N)=O)C(=O)N2)cc3" PI4 SMILES CACTVS 3.341 "CC(C)(C)NC(=O)[CH]1CCCCN1C[CH](O)[CH]2Cc3ccc(OCCCC(=O)N[CH](CC(N)=O)C(=O)N2)cc3" PI4 SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 "CC(C)(C)NC(=O)[C@@H]1CCCC[N@]1C[C@H]([C@@H]2Cc3ccc(cc3)OCCCC(=O)N[C@H](C(=O)N2)CC(=O)N)O" PI4 SMILES "OpenEye OEToolkits" 1.5.0 "CC(C)(C)NC(=O)C1CCCCN1CC(C2Cc3ccc(cc3)OCCCC(=O)NC(C(=O)N2)CC(=O)N)O" PI4 InChI InChI 1.03 "InChI=1S/C28H43N5O6/c1-28(2,3)32-27(38)22-7-4-5-13-33(22)17-23(34)20-15-18-9-11-19(12-10-18)39-14-6-8-25(36)30-21(16-24(29)35)26(37)31-20/h9-12,20-23,34H,4-8,13-17H2,1-3H3,(H2,29,35)(H,30,36)(H,31,37)(H,32,38)/t20-,21-,22-,23+/m0/s1" PI4 InChIKey InChI 1.03 GHEDXAXQQMZPLE-CWBXHPNXSA-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 PI4 "SYSTEMATIC NAME" ACDLabs 10.04 "(2S)-1-{(2R)-2-[(8S,11S)-8-(2-amino-2-oxoethyl)-6,9-dioxo-2-oxa-7,10-diazabicyclo[11.2.2]heptadeca-1(15),13,16-trien-11-yl]-2-hydroxyethyl}-N-tert-butylpiperidine-2-carboxamide" PI4 "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "(1S,2S)-1-[(2R)-2-[(3S,6S)-6-(2-amino-2-oxo-ethyl)-5,8-dioxo-12-oxa-4,7-diazabicyclo[11.2.2]heptadeca-1(15),13,16-trien-3-yl]-2-hydroxy-ethyl]-N-tert-butyl-piperidine-2-carboxamide" # # loop_ _pdbx_chem_comp_audit.comp_id _pdbx_chem_comp_audit.action_type _pdbx_chem_comp_audit.date _pdbx_chem_comp_audit.processing_site PI4 "Create component" 1999-07-08 PDBJ PI4 "Modify descriptor" 2011-06-04 RCSB PI4 "Modify synonyms" 2021-03-01 PDBE # _pdbx_chem_comp_synonyms.ordinal 1 _pdbx_chem_comp_synonyms.comp_id PI4 _pdbx_chem_comp_synonyms.name "MACROCYCLIC PEPTIDOMIMETIC INHIBITOR 4" _pdbx_chem_comp_synonyms.provenance ? _pdbx_chem_comp_synonyms.type ? ##