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                    2008-10-14 
_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 InChI            InChI                1.02b 
InChI=1/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/f/h30-32H,29H2 
PI4 InChIKey         InChI                1.02b GHEDXAXQQMZPLE-YUKRBRBYDT 
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 
# 
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 
# 
