data_PI3
# 
_chem_comp.id                                    PI3 
_chem_comp.name                                  "11-[1-HYDROXY-2-(3-METHYL-BUTYLAMINO)-ETHYL]-8-ISOPROPYL-2-OXA-7,10- DIAZA-BICYCLO[11.2.2]HEPTADECA-1(16),13(17),14-TRIENE-6,9-DIONE" 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C24 H39 N3 O4" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         "MACROCYCLIC PEPTIDOMIMETIC INHIBITOR 3" 
_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                        433.584 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     PI3 
_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        ? 
_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 
PI3 C1   C1   C 0 1 N N N 5.468  4.378  9.415  1.486  -0.739 -5.192 C1   PI3 1  
PI3 C2   C2   C 0 1 N N N 3.584  3.447  10.857 2.255  -0.310 -2.874 C2   PI3 2  
PI3 O3   O3   O 0 1 N N N 3.480  4.199  11.826 2.395  -1.461 -2.516 O3   PI3 3  
PI3 C4   C4   C 0 1 N N N 3.988  3.998  9.497  2.447  0.070  -4.319 C4   PI3 4  
PI3 N5   N5   N 0 1 N N N 3.362  2.136  10.926 1.921  0.658  -1.975 N5   PI3 5  
PI3 C6   C6   C 0 1 N N S 2.952  1.469  12.182 1.746  0.211  -0.577 C6   PI3 6  
PI3 C7   C7   C 0 1 N N N 3.920  0.379  12.666 0.439  0.751  -0.055 C7   PI3 7  
PI3 O8   O8   O 0 1 N N N 3.962  -0.721 12.107 0.394  1.857  0.439  O8   PI3 8  
PI3 C9   C9   C 0 1 N N N 1.535  0.873  12.037 2.900  0.738  0.278  C9   PI3 9  
PI3 C10  C10  C 0 1 N N N 1.212  -0.011 13.217 2.773  0.188  1.700  C10  PI3 10 
PI3 C11  C11  C 0 1 N N N 0.511  1.996  11.917 4.230  0.285  -0.326 C11  PI3 11 
PI3 N12  N12  N 0 1 N N N 4.661  0.693  13.727 -0.680 0.005  -0.136 N12  PI3 12 
PI3 C13  C13  C 0 1 N N S 5.656  -0.235 14.320 -1.954 0.523  0.368  C13  PI3 13 
PI3 C14  C14  C 0 1 N N N 7.070  0.400  14.263 -3.073 0.151  -0.609 C14  PI3 14 
PI3 C15  C15  C 0 1 Y N N 7.359  1.131  12.965 -2.486 -0.026 -1.986 C15  PI3 15 
PI3 C16  C16  C 0 1 Y N N 7.236  2.516  12.892 -2.057 1.077  -2.700 C16  PI3 16 
PI3 C17  C17  C 0 1 Y N N 7.343  3.184  11.692 -1.512 0.918  -3.959 C17  PI3 17 
PI3 C18  C18  C 0 1 Y N N 7.619  0.433  11.786 -2.375 -1.291 -2.532 C18  PI3 18 
PI3 C19  C19  C 0 1 Y N N 7.724  1.094  10.572 -1.831 -1.456 -3.792 C19  PI3 19 
PI3 C20  C20  C 0 1 Y N N 7.577  2.468  10.532 -1.395 -0.350 -4.508 C20  PI3 20 
PI3 O21  O21  O 0 1 N N N 7.573  3.125  9.323  -0.855 -0.509 -5.744 O21  PI3 21 
PI3 C22  C22  C 0 1 N N N 6.301  3.307  8.703  0.395  0.181  -5.740 C22  PI3 22 
PI3 C23  C23  C 0 1 N N R 5.291  -0.607 15.786 -2.248 -0.090 1.738  C23  PI3 23 
PI3 O24  O24  O 0 1 N N N 5.247  0.567  16.597 -3.492 0.413  2.228  O24  PI3 24 
PI3 C25  C25  C 0 1 N N N 6.301  -1.595 16.386 -1.129 0.279  2.713  C25  PI3 25 
PI3 N26  N26  N 0 1 N N N 6.192  -2.946 15.811 -1.411 -0.309 4.029  N26  PI3 26 
PI3 C27  C27  C 0 1 N N N 5.204  -3.897 16.347 -0.305 0.081  4.913  C27  PI3 27 
PI3 C28  C28  C 0 1 N N N 3.972  -3.655 15.478 -0.536 -0.502 6.308  C28  PI3 28 
PI3 C29  C29  C 0 1 N N N 2.870  -4.691 15.684 0.616  -0.095 7.229  C29  PI3 29 
PI3 C30  C30  C 0 1 N N N 3.258  -5.991 15.026 0.384  -0.678 8.624  C30  PI3 30 
PI3 C31  C31  C 0 1 N N N 2.679  -4.913 17.171 1.933  -0.631 6.664  C31  PI3 31 
PI3 H11  1H1  H 0 1 N N N 5.602  5.376  8.938  1.030  -1.528 -4.595 H11  PI3 32 
PI3 H12A 2H1  H 0 0 N N N 5.882  4.606  10.424 2.036  -1.184 -6.022 H12A PI3 33 
PI3 H41  1H4  H 0 1 N N N 3.341  4.859  9.210  3.474  -0.140 -4.617 H41  PI3 34 
PI3 H42  2H4  H 0 1 N N N 3.716  3.285  8.683  2.244  1.133  -4.445 H42  PI3 35 
PI3 HN5  HN5  H 0 1 N N N 3.502  1.654  10.038 1.805  1.585  -2.237 HN5  PI3 36 
PI3 H6   H6   H 0 1 N N N 2.965  2.268  12.959 1.732  -0.877 -0.540 H6   PI3 37 
PI3 H9   H9   H 0 1 N N N 1.497  0.250  11.112 2.865  1.827  0.305  H9   PI3 38 
PI3 H101 1H10 H 0 0 N N N 0.188  -0.441 13.112 3.595  0.563  2.309  H101 PI3 39 
PI3 H102 2H10 H 0 0 N N N 1.982  -0.803 13.365 1.825  0.511  2.131  H102 PI3 40 
PI3 H103 3H10 H 0 0 N N N 1.339  0.526  14.185 2.808  -0.900 1.673  H103 PI3 41 
PI3 H111 1H11 H 0 0 N N N -0.512 1.565  11.812 4.227  -0.798 -0.441 H111 PI3 42 
PI3 H112 2H11 H 0 0 N N N 0.577  2.716  12.765 4.365  0.754  -1.301 H112 PI3 43 
PI3 H113 3H11 H 0 0 N N N 0.756  2.699  11.087 5.047  0.578  0.333  H113 PI3 44 
PI3 H12  H12  H 0 1 N N N 4.469  1.630  14.080 -0.643 -0.879 -0.531 H12  PI3 45 
PI3 H13  H13  H 0 1 N N N 5.648  -1.175 13.721 -1.896 1.607  0.459  H13  PI3 46 
PI3 H141 1H14 H 0 0 N N N 7.235  1.071  15.137 -3.542 -0.778 -0.290 H141 PI3 47 
PI3 H142 2H14 H 0 0 N N N 7.853  -0.366 14.465 -3.817 0.947  -0.631 H142 PI3 48 
PI3 H16  H16  H 0 1 N N N 7.048  3.099  13.809 -2.149 2.065  -2.272 H16  PI3 49 
PI3 H17  H17  H 0 1 N N N 7.242  4.281  11.660 -1.178 1.781  -4.517 H17  PI3 50 
PI3 H18  H18  H 0 1 N N N 7.744  -0.662 11.814 -2.714 -2.152 -1.974 H18  PI3 51 
PI3 H19  H19  H 0 1 N N N 7.923  0.530  9.644  -1.745 -2.444 -4.218 H19  PI3 52 
PI3 H221 1H22 H 0 0 N N N 5.744  2.343  8.628  0.648  0.480  -6.758 H221 PI3 53 
PI3 H222 2H22 H 0 0 N N N 6.407  3.532  7.616  0.318  1.068  -5.110 H222 PI3 54 
PI3 H23  H23  H 0 1 N N N 4.287  -1.093 15.766 -2.306 -1.174 1.646  H23  PI3 55 
PI3 H24  H24  H 0 1 N N N 5.024  0.339  17.492 -3.398 1.373  2.295  H24  PI3 56 
PI3 H251 1H25 H 0 0 N N N 7.341  -1.205 16.294 -1.070 1.364  2.806  H251 PI3 57 
PI3 H252 2H25 H 0 0 N N N 6.215  -1.626 17.497 -0.180 -0.104 2.339  H252 PI3 58 
PI3 H26  H26  H 0 1 N N N 7.112  -3.385 15.842 -1.353 -1.310 3.917  H26  PI3 59 
PI3 H271 1H27 H 0 0 N N N 5.549  -4.956 16.374 -0.257 1.168  4.977  H271 PI3 60 
PI3 H272 2H27 H 0 0 N N N 5.021  -3.806 17.443 0.633  -0.300 4.510  H272 PI3 61 
PI3 H281 1H28 H 0 0 N N N 3.577  -2.623 15.630 -0.584 -1.589 6.244  H281 PI3 62 
PI3 H282 2H28 H 0 0 N N N 4.254  -3.588 14.401 -1.474 -0.120 6.710  H282 PI3 63 
PI3 H29  H29  H 0 1 N N N 1.920  -4.324 15.228 0.663  0.991  7.292  H29  PI3 64 
PI3 H301 1H30 H 0 0 N N N 2.453  -6.747 15.176 1.205  -0.388 9.280  H301 PI3 65 
PI3 H302 2H30 H 0 0 N N N 3.509  -5.855 13.948 -0.553 -0.296 9.026  H302 PI3 66 
PI3 H303 3H30 H 0 0 N N N 4.249  -6.359 15.378 0.337  -1.765 8.560  H303 PI3 67 
PI3 H311 1H31 H 0 0 N N N 1.874  -5.669 17.321 1.885  -1.718 6.600  H311 PI3 68 
PI3 H312 2H31 H 0 0 N N N 3.628  -5.193 17.685 2.098  -0.215 5.670  H312 PI3 69 
PI3 H313 3H31 H 0 0 N N N 2.479  -3.963 17.720 2.754  -0.341 7.320  H313 PI3 70 
# 
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 
PI3 C1  C4   SING N N 1  
PI3 C1  C22  SING N N 2  
PI3 C1  H11  SING N N 3  
PI3 C1  H12A SING N N 4  
PI3 C2  O3   DOUB N N 5  
PI3 C2  C4   SING N N 6  
PI3 C2  N5   SING N N 7  
PI3 C4  H41  SING N N 8  
PI3 C4  H42  SING N N 9  
PI3 N5  C6   SING N N 10 
PI3 N5  HN5  SING N N 11 
PI3 C6  C7   SING N N 12 
PI3 C6  C9   SING N N 13 
PI3 C6  H6   SING N N 14 
PI3 C7  O8   DOUB N N 15 
PI3 C7  N12  SING N N 16 
PI3 C9  C10  SING N N 17 
PI3 C9  C11  SING N N 18 
PI3 C9  H9   SING N N 19 
PI3 C10 H101 SING N N 20 
PI3 C10 H102 SING N N 21 
PI3 C10 H103 SING N N 22 
PI3 C11 H111 SING N N 23 
PI3 C11 H112 SING N N 24 
PI3 C11 H113 SING N N 25 
PI3 N12 C13  SING N N 26 
PI3 N12 H12  SING N N 27 
PI3 C13 C14  SING N N 28 
PI3 C13 C23  SING N N 29 
PI3 C13 H13  SING N N 30 
PI3 C14 C15  SING N N 31 
PI3 C14 H141 SING N N 32 
PI3 C14 H142 SING N N 33 
PI3 C15 C16  SING Y N 34 
PI3 C15 C18  DOUB Y N 35 
PI3 C16 C17  DOUB Y N 36 
PI3 C16 H16  SING N N 37 
PI3 C17 C20  SING Y N 38 
PI3 C17 H17  SING N N 39 
PI3 C18 C19  SING Y N 40 
PI3 C18 H18  SING N N 41 
PI3 C19 C20  DOUB Y N 42 
PI3 C19 H19  SING N N 43 
PI3 C20 O21  SING N N 44 
PI3 O21 C22  SING N N 45 
PI3 C22 H221 SING N N 46 
PI3 C22 H222 SING N N 47 
PI3 C23 O24  SING N N 48 
PI3 C23 C25  SING N N 49 
PI3 C23 H23  SING N N 50 
PI3 O24 H24  SING N N 51 
PI3 C25 N26  SING N N 52 
PI3 C25 H251 SING N N 53 
PI3 C25 H252 SING N N 54 
PI3 N26 C27  SING N N 55 
PI3 N26 H26  SING N N 56 
PI3 C27 C28  SING N N 57 
PI3 C27 H271 SING N N 58 
PI3 C27 H272 SING N N 59 
PI3 C28 C29  SING N N 60 
PI3 C28 H281 SING N N 61 
PI3 C28 H282 SING N N 62 
PI3 C29 C30  SING N N 63 
PI3 C29 C31  SING N N 64 
PI3 C29 H29  SING N N 65 
PI3 C30 H301 SING N N 66 
PI3 C30 H302 SING N N 67 
PI3 C30 H303 SING N N 68 
PI3 C31 H311 SING N N 69 
PI3 C31 H312 SING N N 70 
PI3 C31 H313 SING N N 71 
# 
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 
PI3 SMILES           ACDLabs              10.04 O=C1NC(C(O)CNCCC(C)C)Cc2ccc(OCCCC(=O)NC1C(C)C)cc2                                                                                                                                                           
PI3 InChI            InChI                1.02b InChI=1/C24H39N3O4/c1-16(2)11-12-25-15-21(28)20-14-18-7-9-19(10-8-18)31-13-5-6-22(29)27-23(17(3)4)24(30)26-20/h7-10,16-17,20-21,23,25,28H,5-6,11-15H2,1-4H3,(H,26,30)(H,27,29)/t20-,21+,23-/m0/s1/f/h26-27H 
PI3 InChIKey         InChI                1.02b IUDJFSQFSQZRNP-PQZUULDADQ                                                                                                                                                                                   
PI3 SMILES_CANONICAL CACTVS               3.341 CC(C)CCNC[C@@H](O)[C@@H]1Cc2ccc(OCCCC(=O)N[C@@H](C(C)C)C(=O)N1)cc2                                                                                                                                          
PI3 SMILES           CACTVS               3.341 CC(C)CCNC[CH](O)[CH]1Cc2ccc(OCCCC(=O)N[CH](C(C)C)C(=O)N1)cc2                                                                                                                                                
PI3 SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 CC(C)CCNC[C@H]([C@@H]1Cc2ccc(cc2)OCCCC(=O)N[C@H](C(=O)N1)C(C)C)O                                                                                                                                            
PI3 SMILES           "OpenEye OEToolkits" 1.5.0 CC(C)CCNCC(C1Cc2ccc(cc2)OCCCC(=O)NC(C(=O)N1)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 
PI3 "SYSTEMATIC NAME" ACDLabs              10.04 (8S,11S)-11-{(1R)-1-hydroxy-2-[(3-methylbutyl)amino]ethyl}-8-(1-methylethyl)-2-oxa-7,10-diazabicyclo[11.2.2]heptadeca-1(15),13,16-triene-6,9-dione 
PI3 "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 (3S,6S)-3-[(1R)-1-hydroxy-2-(3-methylbutylamino)ethyl]-6-propan-2-yl-12-oxa-4,7-diazabicyclo[11.2.2]heptadeca-1(15),13,16-triene-5,8-dione         
# 
