data_PI6 # _chem_comp.id PI6 _chem_comp.name "[1-BENZYL-3-(8-SEC-BUTYL-7,10-DIOXO-2-OXA-6,9-DIAZA-BICYCLO[11.2.2] HEPTADECA-1(16),13(17),14-TRIEN-11-YLAMINO)-2-HYDROXY-PROPYL]-CARBAMIC ACID TERT-BUTYL ESTER" _chem_comp.type peptide-like _chem_comp.pdbx_type HETAIN _chem_comp.formula "C33 H48 N4 O6" _chem_comp.mon_nstd_parent_comp_id ? _chem_comp.pdbx_synonyms "MACROCYCLIC PEPTIDOMIMETIC INHIBITOR 6" _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 0EZ _chem_comp.formula_weight 596.757 _chem_comp.one_letter_code ? _chem_comp.three_letter_code PI6 _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 1MTR _chem_comp.pdbx_subcomponent_list "BOC T00 ILE 0D8" _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 PI6 O1 O1 O 0 1 N N N 3.812 -0.151 12.128 5.776 -0.828 0.257 O1 BOC 1 PI6 C C1 C 0 1 N N N 3.839 1.070 12.419 5.427 -0.724 -0.902 C BOC 2 PI6 O2 O2 O 0 1 N N N 2.846 1.907 12.139 6.259 -1.100 -1.891 O2 BOC 3 PI6 CT C2 C 0 1 N N N 1.609 1.362 11.669 7.557 -1.621 -1.500 CT BOC 4 PI6 C1 C3 C 0 1 N N N 1.066 0.359 12.657 7.365 -2.864 -0.628 C1 BOC 5 PI6 C2 C4 C 0 1 N N N 0.650 2.515 11.579 8.356 -1.993 -2.750 C2 BOC 6 PI6 C3 C5 C 0 1 N N N 1.815 0.746 10.269 8.316 -0.555 -0.707 C3 BOC 7 PI6 N N1 N 0 1 N N N 4.892 1.641 12.992 4.206 -0.237 -1.197 N1 T00 8 PI6 CA C6 C 0 1 N N S 6.086 0.898 13.394 3.298 0.166 -0.120 C1 T00 9 PI6 C4 C7 C 0 1 N N R 6.025 0.540 14.867 1.852 0.079 -0.612 C2 T00 10 PI6 OXT O4 O 0 1 N N N 7.214 -0.158 15.210 1.647 1.032 -1.657 O1 T00 11 PI6 CB C8 C 0 1 N N N 7.325 1.731 13.147 3.610 1.605 0.297 C3 T00 12 PI6 CG C9 C 0 1 Y N N 7.517 2.083 11.738 4.991 1.667 0.895 C4 T00 13 PI6 CD1 C10 C 0 1 Y N N 7.852 1.103 10.818 6.085 1.910 0.086 C5 T00 14 PI6 CD2 C11 C 0 1 Y N N 7.277 3.381 11.300 5.164 1.486 2.255 C6 T00 15 PI6 CE1 C12 C 0 1 Y N N 7.934 1.407 9.477 7.352 1.966 0.635 C7 T00 16 PI6 CE2 C13 C 0 1 Y N N 7.359 3.695 9.959 6.431 1.543 2.804 C8 T00 17 PI6 CZ C14 C 0 1 Y N N 7.686 2.701 9.042 7.526 1.780 1.994 C9 T00 18 PI6 CM C15 C 0 1 N N N 4.826 -0.350 15.162 0.900 0.380 0.547 C10 T00 19 PI6 N1 N2 N 0 1 N N N 4.980 -0.749 16.565 -0.487 0.180 0.106 N2 T00 20 PI6 CA1 C16 C 0 1 N N S 4.733 -2.185 16.866 -1.424 0.349 1.224 C11 T00 21 PI6 C5 C17 C 0 1 N N N 5.727 -3.184 16.261 -2.657 -0.480 0.976 C12 T00 22 PI6 O O5 O 0 1 N N N 5.938 -3.213 15.043 -3.727 -0.152 1.445 O2 T00 23 PI6 CB1 C18 C 0 1 N N N 3.307 -2.601 16.485 -1.819 1.824 1.341 C13 T00 24 PI6 CG1 C19 C 0 1 Y N N 3.088 -4.088 16.588 -3.134 2.044 0.638 C14 T00 25 PI6 CD11 C20 C 0 0 Y N N 3.043 -4.729 17.840 -4.317 1.687 1.260 C15 T00 26 PI6 CD21 C21 C 0 0 Y N N 3.069 -4.882 15.437 -3.157 2.604 -0.626 C16 T00 27 PI6 CE11 C22 C 0 0 Y N N 3.007 -6.103 17.928 -5.522 1.878 0.613 C17 T00 28 PI6 CE21 C23 C 0 0 Y N N 3.027 -6.265 15.516 -4.360 2.803 -1.274 C18 T00 29 PI6 CZ1 C24 C 0 1 Y N N 3.006 -6.870 16.757 -5.547 2.434 -0.657 C19 T00 30 PI6 N2 N3 N 0 1 N N N 6.302 -4.005 17.141 -2.548 -1.611 0.210 N ILE 31 PI6 CA2 C25 C 0 1 N N S 7.239 -5.100 16.804 -3.826 -2.346 0.027 CA ILE 32 PI6 C6 C26 C 0 1 N N N 6.869 -6.158 17.847 -4.742 -1.507 -0.825 C ILE 33 PI6 O3 O8 O 0 1 N N N 6.850 -5.873 19.059 -4.320 -0.526 -1.401 O ILE 34 PI6 CB2 C27 C 0 1 N N S 8.739 -4.777 17.039 -4.477 -2.595 1.389 CB ILE 35 PI6 CG11 C28 C 0 0 N N N 9.222 -3.621 16.161 -3.570 -3.497 2.230 CG1 ILE 36 PI6 CG2 C29 C 0 1 N N N 9.576 -6.027 16.773 -5.831 -3.278 1.190 CG2 ILE 37 PI6 CD12 C30 C 0 0 N N N 9.703 -4.059 14.843 -2.286 -2.743 2.582 CD1 ILE 38 PI6 OH O6 O 0 1 N N N 3.018 -8.249 16.778 -6.731 2.610 -1.301 OH 0D8 39 PI6 N3 N4 N 0 1 N N N 6.543 -7.355 17.370 -6.052 -1.867 -0.939 N3 0D8 40 PI6 CA3 C31 C 0 1 N N N 6.161 -8.448 18.247 -6.887 -0.994 -1.792 CA3 0D8 41 PI6 C7 C32 C 0 1 N N N 5.077 -9.284 17.577 -7.246 0.268 -1.006 C7 0D8 42 PI6 C8 C33 C 0 1 N N N 3.687 -8.760 17.916 -7.289 1.466 -1.954 C8 0D8 43 PI6 H11 H1 H 0 1 N N N 0.116 -0.050 12.281 6.825 -3.624 -1.193 H11 BOC 44 PI6 H12 H2 H 0 1 N N N 1.791 -0.458 12.786 8.340 -3.255 -0.334 H12 BOC 45 PI6 H13 H3 H 0 1 N N N 0.895 0.853 13.625 6.796 -2.600 0.262 H13 BOC 46 PI6 H21 H4 H 0 1 N N N -0.325 2.154 11.220 8.492 -1.107 -3.371 H21 BOC 47 PI6 H22 H5 H 0 1 N N N 0.530 2.970 12.573 9.330 -2.384 -2.456 H22 BOC 48 PI6 H23 H6 H 0 1 N N N 1.044 3.265 10.878 7.815 -2.752 -3.315 H23 BOC 49 PI6 H31 H7 H 0 1 N N N 0.864 0.327 9.908 7.747 -0.290 0.184 H31 BOC 50 PI6 H32 H8 H 0 1 N N N 2.160 1.525 9.573 9.290 -0.946 -0.413 H32 BOC 51 PI6 H33 H9 H 0 1 N N N 2.569 -0.053 10.327 8.452 0.331 -1.328 H33 BOC 52 PI6 H H11 H 0 1 N N N 4.867 2.627 13.157 3.927 -0.154 -2.123 H1 T00 53 PI6 HA H13 H 0 1 N N N 6.158 -0.029 12.806 3.431 -0.497 0.735 H2 T00 54 PI6 HC H14 H 0 1 N N N 5.939 1.464 15.458 1.657 -0.924 -0.992 H3 T00 55 PI6 HOR H15 H 0 1 N N N 7.191 -0.390 16.131 1.803 1.949 -1.390 H4 T00 56 PI6 HB2 H16 H 0 1 N N N 7.243 2.660 13.731 3.563 2.255 -0.577 H5 T00 57 PI6 HB3 H17 H 0 1 N N N 8.202 1.161 13.487 2.879 1.936 1.035 H6 T00 58 PI6 HD1 H18 H 0 1 N N N 8.050 0.096 11.154 5.950 2.055 -0.976 H7 T00 59 PI6 HD2 H19 H 0 1 N N N 7.024 4.150 12.015 4.309 1.301 2.888 H8 T00 60 PI6 HE1 H20 H 0 1 N N N 8.191 0.638 8.764 8.207 2.155 0.002 H9 T00 61 PI6 HE2 H21 H 0 1 N N N 7.171 4.704 9.624 6.566 1.402 3.866 H10 T00 62 PI6 HZ H22 H 0 1 N N N 7.747 2.937 7.990 8.516 1.824 2.423 H11 T00 63 PI6 HM2 H24 H 0 1 N N N 3.888 0.207 15.020 1.117 -0.290 1.379 H12 T00 64 PI6 HM3 H25 H 0 1 N N N 4.831 -1.234 14.507 1.034 1.413 0.868 H13 T00 65 PI6 H1 H26 H 0 1 N N N 4.339 -0.208 17.109 -0.601 -0.723 -0.328 H14 T00 66 PI6 HA1 H28 H 0 1 N N N 4.807 -2.299 17.958 -0.949 0.026 2.150 H15 T00 67 PI6 HB21 H29 H 0 0 N N N 2.601 -2.094 17.159 -1.919 2.092 2.393 H16 T00 68 PI6 HB31 H30 H 0 0 N N N 3.114 -2.288 15.448 -1.051 2.444 0.878 H17 T00 69 PI6 HD11 H31 H 0 0 N N N 3.037 -4.136 18.743 -4.297 1.258 2.251 H18 T00 70 PI6 HD21 H32 H 0 0 N N N 3.087 -4.408 14.467 -2.232 2.886 -1.108 H19 T00 71 PI6 HE11 H33 H 0 0 N N N 2.980 -6.585 18.894 -6.445 1.595 1.097 H20 T00 72 PI6 HE21 H34 H 0 0 N N N 3.011 -6.863 14.617 -4.378 3.245 -2.259 H21 T00 73 PI6 H2 H37 H 0 1 N N N 6.082 -3.870 18.107 -1.710 -1.906 -0.178 H ILE 74 PI6 HA2 H39 H 0 1 N N N 7.077 -5.477 15.784 -3.634 -3.297 -0.470 HA ILE 75 PI6 HB H40 H 0 1 N N N 8.867 -4.490 18.093 -4.620 -1.645 1.902 HB ILE 76 PI6 HG12 H41 H 0 0 N N N 8.387 -2.921 16.014 -4.088 -3.780 3.146 HG12 ILE 77 PI6 HG13 H42 H 0 0 N N N 10.044 -3.107 16.680 -3.320 -4.393 1.661 HG13 ILE 78 PI6 HG21 H43 H 0 0 N N N 10.639 -5.799 16.939 -5.774 -3.959 0.341 HG21 ILE 79 PI6 HG22 H44 H 0 0 N N N 9.262 -6.830 17.456 -6.091 -3.838 2.089 HG22 ILE 80 PI6 HG23 H45 H 0 0 N N N 9.429 -6.352 15.732 -6.594 -2.523 0.999 HG23 ILE 81 PI6 HD12 H46 H 0 0 N N N 10.034 -3.184 14.264 -1.674 -2.629 1.688 HD11 ILE 82 PI6 HD13 H47 H 0 0 N N N 10.546 -4.753 14.973 -2.540 -1.758 2.976 HD12 ILE 83 PI6 HD14 H48 H 0 0 N N N 8.889 -4.567 14.306 -1.731 -3.303 3.334 HD13 ILE 84 PI6 H3 H50 H 0 1 N N N 6.561 -7.507 16.382 -6.414 -2.646 -0.489 H3 0D8 85 PI6 HA21 H52 H 0 0 N N N 7.039 -9.080 18.449 -6.331 -0.720 -2.689 HA21 0D8 86 PI6 HA3 H53 H 0 1 N N N 5.777 -8.041 19.194 -7.799 -1.522 -2.073 HA3 0D8 87 PI6 H14 H55 H 0 1 N N N 3.091 -9.583 18.338 -8.323 1.674 -2.230 H14 0D8 88 PI6 H24 H56 H 0 1 N N N 3.783 -7.957 18.661 -6.711 1.242 -2.850 H24 0D8 89 PI6 H89 H89 H 0 1 N N N 5.218 -9.247 16.487 -8.222 0.139 -0.539 H89 0D8 90 PI6 H99 H99 H 0 1 N N N 5.162 -10.325 17.923 -6.495 0.441 -0.235 H99 0D8 91 # # 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 PI6 O1 C DOUB N N 1 PI6 C O2 SING N N 2 PI6 O2 CT SING N N 3 PI6 CT C1 SING N N 4 PI6 CT C2 SING N N 5 PI6 CT C3 SING N N 6 PI6 C1 H11 SING N N 7 PI6 C1 H12 SING N N 8 PI6 C1 H13 SING N N 9 PI6 C2 H21 SING N N 10 PI6 C2 H22 SING N N 11 PI6 C2 H23 SING N N 12 PI6 C3 H31 SING N N 13 PI6 C3 H32 SING N N 14 PI6 C3 H33 SING N N 15 PI6 N CA SING N N 16 PI6 N H SING N N 17 PI6 CA C4 SING N N 18 PI6 CA CB SING N N 19 PI6 CA HA SING N N 20 PI6 C4 OXT SING N N 21 PI6 C4 CM SING N N 22 PI6 C4 HC SING N N 23 PI6 OXT HOR SING N N 24 PI6 CB CG SING N N 25 PI6 CB HB2 SING N N 26 PI6 CB HB3 SING N N 27 PI6 CG CD1 DOUB Y N 28 PI6 CG CD2 SING Y N 29 PI6 CD1 CE1 SING Y N 30 PI6 CD1 HD1 SING N N 31 PI6 CD2 CE2 DOUB Y N 32 PI6 CD2 HD2 SING N N 33 PI6 CE1 CZ DOUB Y N 34 PI6 CE1 HE1 SING N N 35 PI6 CE2 CZ SING Y N 36 PI6 CE2 HE2 SING N N 37 PI6 CZ HZ SING N N 38 PI6 CM HM2 SING N N 39 PI6 CM HM3 SING N N 40 PI6 N1 CA1 SING N N 41 PI6 N1 H1 SING N N 42 PI6 CA1 C5 SING N N 43 PI6 CA1 CB1 SING N N 44 PI6 CA1 HA1 SING N N 45 PI6 C5 O DOUB N N 46 PI6 CB1 CG1 SING N N 47 PI6 CB1 HB21 SING N N 48 PI6 CB1 HB31 SING N N 49 PI6 CG1 CD11 DOUB Y N 50 PI6 CG1 CD21 SING Y N 51 PI6 CD11 CE11 SING Y N 52 PI6 CD11 HD11 SING N N 53 PI6 CD21 CE21 DOUB Y N 54 PI6 CD21 HD21 SING N N 55 PI6 CE11 CZ1 DOUB Y N 56 PI6 CE11 HE11 SING N N 57 PI6 CE21 CZ1 SING Y N 58 PI6 CE21 HE21 SING N N 59 PI6 CZ1 OH SING N N 60 PI6 N2 CA2 SING N N 61 PI6 N2 H2 SING N N 62 PI6 CA2 C6 SING N N 63 PI6 CA2 CB2 SING N N 64 PI6 CA2 HA2 SING N N 65 PI6 C6 O3 DOUB N N 66 PI6 CB2 CG11 SING N N 67 PI6 CB2 CG2 SING N N 68 PI6 CB2 HB SING N N 69 PI6 CG11 CD12 SING N N 70 PI6 CG11 HG12 SING N N 71 PI6 CG11 HG13 SING N N 72 PI6 CG2 HG21 SING N N 73 PI6 CG2 HG22 SING N N 74 PI6 CG2 HG23 SING N N 75 PI6 CD12 HD12 SING N N 76 PI6 CD12 HD13 SING N N 77 PI6 CD12 HD14 SING N N 78 PI6 N3 CA3 SING N N 79 PI6 N3 H3 SING N N 80 PI6 CA3 C7 SING N N 81 PI6 CA3 HA21 SING N N 82 PI6 CA3 HA3 SING N N 83 PI6 C8 H14 SING N N 84 PI6 C8 H24 SING N N 85 PI6 C N SING N N 86 PI6 CM N1 SING N N 87 PI6 C5 N2 SING N N 88 PI6 C6 N3 SING N N 89 PI6 C7 C8 SING N N 90 PI6 C7 H89 SING N N 91 PI6 C7 H99 SING N N 92 PI6 OH C8 SING N N 93 # # 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 PI6 SMILES ACDLabs 12.01 "O=C(OC(C)(C)C)NC(Cc1ccccc1)C(O)CNC3C(=O)NC(C(=O)NCCCOc2ccc(cc2)C3)C(C)CC" PI6 InChI InChI 1.03 "InChI=1S/C33H48N4O6/c1-6-22(2)29-31(40)34-17-10-18-42-25-15-13-24(14-16-25)20-27(30(39)37-29)35-21-28(38)26(19-23-11-8-7-9-12-23)36-32(41)43-33(3,4)5/h7-9,11-16,22,26-29,35,38H,6,10,17-21H2,1-5H3,(H,34,40)(H,36,41)(H,37,39)/t22-,26-,27-,28+,29-/m0/s1" PI6 InChIKey InChI 1.03 RFUKEYSMPSCDLJ-CLFZCTPNSA-N PI6 SMILES_CANONICAL CACTVS 3.370 "CC[C@H](C)[C@@H]1NC(=O)[C@H](Cc2ccc(OCCCNC1=O)cc2)NC[C@@H](O)[C@H](Cc3ccccc3)NC(=O)OC(C)(C)C" PI6 SMILES CACTVS 3.370 "CC[CH](C)[CH]1NC(=O)[CH](Cc2ccc(OCCCNC1=O)cc2)NC[CH](O)[CH](Cc3ccccc3)NC(=O)OC(C)(C)C" PI6 SMILES_CANONICAL "OpenEye OEToolkits" 1.7.6 "CC[C@H](C)[C@H]1C(=O)NCCCOc2ccc(cc2)C[C@@H](C(=O)N1)NC[C@H]([C@H](Cc3ccccc3)NC(=O)OC(C)(C)C)O" PI6 SMILES "OpenEye OEToolkits" 1.7.6 "CCC(C)C1C(=O)NCCCOc2ccc(cc2)CC(C(=O)N1)NCC(C(Cc3ccccc3)NC(=O)OC(C)(C)C)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 PI6 "SYSTEMATIC NAME" ACDLabs 12.01 "tert-butyl [(2S,3R)-4-{[(8S,11S)-8-[(2S)-butan-2-yl]-7,10-dioxo-2-oxa-6,9-diazabicyclo[11.2.2]heptadeca-1(15),13,16-trien-11-yl]amino}-3-hydroxy-1-phenylbutan-2-yl]carbamate" PI6 "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.7.6 "tert-butyl N-[(2S,3R)-4-[[(3S,6S)-6-[(2S)-butan-2-yl]-4,7-bis(oxidanylidene)-12-oxa-5,8-diazabicyclo[11.2.2]heptadeca-1(16),13(17),14-trien-3-yl]amino]-3-oxidanyl-1-phenyl-butan-2-yl]carbamate" # # loop_ _pdbx_chem_comp_audit.comp_id _pdbx_chem_comp_audit.action_type _pdbx_chem_comp_audit.date _pdbx_chem_comp_audit.processing_site PI6 "Create component" 1999-07-08 RCSB PI6 "Modify descriptor" 2011-06-04 RCSB PI6 "Modify subcomponent list" 2012-07-19 RCSB PI6 "Modify atom id" 2012-07-19 RCSB PI6 "Modify model coordinates code" 2012-07-19 RCSB PI6 "Modify synonyms" 2021-03-01 PDBE # _pdbx_chem_comp_synonyms.ordinal 1 _pdbx_chem_comp_synonyms.comp_id PI6 _pdbx_chem_comp_synonyms.name "MACROCYCLIC PEPTIDOMIMETIC INHIBITOR 6" _pdbx_chem_comp_synonyms.provenance ? _pdbx_chem_comp_synonyms.type ? ##