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                                  NON-POLYMER 
_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                    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                        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        ? 
_chem_comp.pdbx_ideal_coordinates_missing_flag   N 
_chem_comp.pdbx_model_coordinates_db_code        1B6M 
_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 
PI6 O1   O1   O 0 1 N N N 2.808  1.969   12.124 2.146  0.433  -4.686 O1   PI6 1  
PI6 O2   O2   O 0 1 N N N 3.835  -0.032  12.046 0.959  -1.236 -3.833 O2   PI6 2  
PI6 C3   C3   C 0 1 N N N 1.077  0.320   12.634 4.454  0.390  -5.461 C3   PI6 3  
PI6 C4   C4   C 0 1 N N N 0.556  2.486   11.539 3.738  -0.967 -3.490 C4   PI6 4  
PI6 C5   C5   C 0 1 N N N 1.809  0.765   10.258 2.957  -1.584 -5.782 C5   PI6 5  
PI6 C6   C6   C 0 1 N N N 1.587  1.371   11.646 3.308  -0.420 -4.852 C6   PI6 6  
PI6 C7   C7   C 0 1 N N N 3.821  1.158   12.399 1.011  -0.068 -4.164 C7   PI6 7  
PI6 N8   N8   N 0 1 N N N 4.828  1.713   13.068 -0.068 0.724  -4.010 N8   PI6 8  
PI6 C9   C9   C 0 1 N N S 6.033  0.966   13.447 -1.303 0.177  -3.442 C9   PI6 9  
PI6 C10  C10  C 0 1 N N N 7.275  1.805   13.183 -1.807 -0.965 -4.324 C10  PI6 10 
PI6 C11  C11  C 0 1 Y N N 7.475  2.132   11.746 -2.079 -0.446 -5.713 C11  PI6 11 
PI6 C12  C12  C 0 1 Y N N 7.865  1.146   10.850 -1.078 -0.462 -6.665 C12  PI6 12 
PI6 C13  C13  C 0 1 Y N N 7.235  3.417   11.276 -3.332 0.039  -6.035 C13  PI6 13 
PI6 C14  C14  C 0 1 Y N N 8.017  1.435   9.508  -1.327 0.014  -7.939 C14  PI6 14 
PI6 C15  C15  C 0 1 Y N N 7.385  3.717   9.934  -3.581 0.520  -7.308 C15  PI6 15 
PI6 C16  C16  C 0 1 Y N N 7.772  2.723   9.046  -2.579 0.505  -8.260 C16  PI6 16 
PI6 C17  C17  C 0 1 N N R 6.008  0.539   14.904 -1.026 -0.349 -2.032 C17  PI6 17 
PI6 O18  O18  O 0 1 N N N 7.205  -0.189  15.192 -2.231 -0.882 -1.479 O18  PI6 18 
PI6 C19  C19  C 0 1 N N N 4.804  -0.349  15.187 -0.522 0.794  -1.150 C19  PI6 19 
PI6 N20  N20  N 0 1 N N N 4.892  -0.754  16.600 -0.257 0.288  0.202  N20  PI6 20 
PI6 C21  C21  C 0 1 N N S 4.673  -2.201  16.861 0.221  1.429  0.994  C21  PI6 21 
PI6 C22  C22  C 0 1 N N N 3.267  -2.654  16.446 -0.971 2.278  1.436  C22  PI6 22 
PI6 C23  C23  C 0 1 Y N N 3.121  -4.151  16.570 -1.658 1.611  2.600  C23  PI6 23 
PI6 C24  C24  C 0 1 Y N N 3.091  -4.767  17.823 -1.349 1.991  3.893  C24  PI6 24 
PI6 C25  C25  C 0 1 Y N N 3.131  -6.148  17.942 -1.978 1.381  4.962  C25  PI6 25 
PI6 C26  C26  C 0 1 Y N N 3.169  -4.963  15.439 -2.595 0.621  2.373  C26  PI6 26 
PI6 C27  C27  C 0 1 Y N N 3.209  -6.339  15.547 -3.227 0.009  3.438  C27  PI6 27 
PI6 C28  C28  C 0 1 Y N N 3.198  -6.928  16.795 -2.920 0.388  4.736  C28  PI6 28 
PI6 O29  O29  O 0 1 N N N 3.305  -8.296  16.863 -3.540 -0.212 5.786  O29  PI6 29 
PI6 C30  C30  C 0 1 N N N 3.790  -8.941  18.029 -2.545 -0.976 6.471  C30  PI6 30 
PI6 C31  C31  C 0 1 N N N 5.689  -3.186  16.291 0.958  0.925  2.207  C31  PI6 31 
PI6 O32  O32  O 0 1 N N N 5.996  -3.175  15.097 1.339  1.696  3.063  O32  PI6 32 
PI6 N33  N33  N 0 1 N N N 6.187  -4.050  17.169 1.190  -0.414 2.327  N33  PI6 33 
PI6 C34  C34  C 0 1 N N S 7.152  -5.100  16.815 1.936  -0.836 3.530  C34  PI6 34 
PI6 C35  C35  C 0 1 N N N 6.912  -6.178  17.865 0.965  -1.040 4.664  C35  PI6 35 
PI6 O36  O36  O 0 1 N N N 7.047  -5.922  19.064 0.725  -0.138 5.438  O36  PI6 36 
PI6 C37  C37  C 0 1 N N S 8.628  -4.637  16.895 2.949  0.244  3.912  C37  PI6 37 
PI6 C38  C38  C 0 1 N N N 8.898  -3.565  15.839 3.806  0.593  2.693  C38  PI6 38 
PI6 C39  C39  C 0 1 N N N 9.567  -5.831  16.696 3.847  -0.272 5.037  C39  PI6 39 
PI6 C40  C40  C 0 1 N N N 10.344 -3.398  15.484 4.818  1.674  3.074  C40  PI6 40 
PI6 N41  N41  N 0 1 N N N 6.508  -7.362  17.415 0.359  -2.254 4.806  N41  PI6 41 
PI6 C42  C42  C 0 1 N N N 6.254  -8.457  18.335 -0.550 -2.391 5.964  C42  PI6 42 
PI6 C43  C43  C 0 1 N N N 5.213  -9.454  17.845 -1.969 -2.029 5.522  C43  PI6 43 
PI6 H31  1H3  H 0 1 N N N 0.132  -0.142  12.264 5.326  -0.250 -5.586 H31  PI6 44 
PI6 H32  2H3  H 0 1 N N N 1.853  -0.448  12.857 4.147  0.780  -6.432 H32  PI6 45 
PI6 H33A 3H3  H 0 0 N N N 0.957  0.740   13.659 4.704  1.219  -4.799 H33A PI6 46 
PI6 H41A 1H4  H 0 0 N N N -0.388 2.023   11.169 3.988  -0.138 -2.828 H41A PI6 47 
PI6 H42  2H4  H 0 1 N N N 0.423  3.052   12.490 2.922  -1.545 -3.056 H42  PI6 48 
PI6 H43  3H4  H 0 1 N N N 0.899  3.341   10.911 4.611  -1.608 -3.615 H43  PI6 49 
PI6 H51  1H5  H 0 1 N N N 0.864  0.302   9.888  2.651  -1.194 -6.752 H51  PI6 50 
PI6 H52  2H5  H 0 1 N N N 2.219  1.510   9.537  3.830  -2.225 -5.907 H52  PI6 51 
PI6 H53  3H5  H 0 1 N N N 2.659  0.043   10.248 2.141  -2.161 -5.348 H53  PI6 52 
PI6 H8   H8   H 0 1 N N N 4.678  2.697   13.287 -0.026 1.656  -4.275 H8   PI6 53 
PI6 H9   H9   H 0 1 N N N 6.058  0.043   12.821 -2.059 0.961  -3.395 H9   PI6 54 
PI6 H101 1H10 H 0 0 N N N 7.263  2.732   13.801 -1.051 -1.749 -4.371 H101 PI6 55 
PI6 H102 2H10 H 0 0 N N N 8.181  1.312   13.605 -2.726 -1.372 -3.902 H102 PI6 56 
PI6 H12  H12  H 0 1 N N N 8.056  0.120   11.208 -0.100 -0.846 -6.414 H12  PI6 57 
PI6 H13  H13  H 0 1 N N N 6.921  4.208   11.977 -4.115 0.051  -5.292 H13  PI6 58 
PI6 H14  H14  H 0 1 N N N 8.332  0.641   8.809  -0.544 0.002  -8.682 H14  PI6 59 
PI6 H15  H15  H 0 1 N N N 7.197  4.742   9.574  -4.558 0.904  -7.559 H15  PI6 60 
PI6 H16  H16  H 0 1 N N N 7.884  2.956   7.973  -2.773 0.878  -9.255 H16  PI6 61 
PI6 H17  H17  H 0 1 N N N 5.937  1.448   15.545 -0.270 -1.133 -2.079 H17  PI6 62 
PI6 H18  H18  H 0 1 N N N 7.189  -0.456  16.103 -2.872 -0.158 -1.455 H18  PI6 63 
PI6 H191 1H19 H 0 0 N N N 3.832  0.134   14.929 -1.278 1.577  -1.103 H191 PI6 64 
PI6 H192 2H19 H 0 0 N N N 4.722  -1.213  14.487 0.396  1.200  -1.573 H192 PI6 65 
PI6 H20  H20  H 0 1 N N N 4.252  -0.195  17.165 0.516  -0.355 0.125  H20  PI6 66 
PI6 H21  H21  H 0 1 N N N 4.812  -2.244  17.966 0.893  2.035  0.386  H21  PI6 67 
PI6 H221 1H22 H 0 0 N N N 2.476  -2.115  17.018 -0.622 3.266  1.738  H221 PI6 68 
PI6 H222 2H22 H 0 0 N N N 3.006  -2.299  15.421 -1.673 2.378  0.609  H222 PI6 69 
PI6 H24  H24  H 0 1 N N N 3.034  -4.151  18.736 -0.615 2.764  4.068  H24  PI6 70 
PI6 H25  H25  H 0 1 N N N 3.109  -6.620  18.938 -1.736 1.678  5.972  H25  PI6 71 
PI6 H26  H26  H 0 1 N N N 3.175  -4.506  14.435 -2.834 0.326  1.362  H26  PI6 72 
PI6 H27  H27  H 0 1 N N N 3.249  -6.965  14.639 -3.960 -0.764 3.260  H27  PI6 73 
PI6 H301 1H30 H 0 0 N N N 3.710  -8.277  18.921 -1.747 -0.314 6.807  H301 PI6 74 
PI6 H302 2H30 H 0 0 N N N 3.104  -9.757  18.355 -2.995 -1.470 7.332  H302 PI6 75 
PI6 H33  H33  H 0 1 N N N 5.829  -3.907  18.113 0.884  -1.050 1.661  H33  PI6 76 
PI6 H34  H34  H 0 1 N N N 7.003  -5.428  15.760 2.459  -1.770 3.326  H34  PI6 77 
PI6 H37  H37  H 0 1 N N N 8.816  -4.201  17.903 2.419  1.135  4.250  H37  PI6 78 
PI6 H381 1H38 H 0 0 N N N 8.292  -3.759  14.923 3.165  0.961  1.892  H381 PI6 79 
PI6 H382 2H38 H 0 0 N N N 8.459  -2.589  16.153 4.335  -0.297 2.355  H382 PI6 80 
PI6 H391 1H39 H 0 0 N N N 10.629 -5.497  16.753 4.454  -1.098 4.667  H391 PI6 81 
PI6 H392 2H39 H 0 0 N N N 9.349  -6.656  17.413 4.499  0.532  5.380  H392 PI6 82 
PI6 H393 3H39 H 0 0 N N N 9.352  -6.376  15.747 3.230  -0.617 5.866  H393 PI6 83 
PI6 H401 1H40 H 0 0 N N N 10.540 -2.616  14.713 5.429  1.922  2.206  H401 PI6 84 
PI6 H402 2H40 H 0 0 N N N 10.949 -3.203  16.399 4.289  2.565  3.413  H402 PI6 85 
PI6 H403 3H40 H 0 0 N N N 10.782 -4.373  15.169 5.459  1.306  3.876  H403 PI6 86 
PI6 H41  H41  H 0 1 N N N 6.397  -7.427  16.403 0.516  -2.984 4.187  H41  PI6 87 
PI6 H421 1H42 H 0 0 N N N 7.204  -8.979  18.591 -0.232 -1.717 6.760  H421 PI6 88 
PI6 H422 2H42 H 0 0 N N N 5.975  -8.065  19.341 -0.531 -3.420 6.324  H422 PI6 89 
PI6 H431 1H43 H 0 0 N N N 5.348  -10.448 18.330 -2.596 -2.921 5.545  H431 PI6 90 
PI6 H432 2H43 H 0 0 N N N 5.402  -9.745  16.785 -1.943 -1.630 4.508  H432 PI6 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  C6   SING N N 1  
PI6 O1  C7   SING N N 2  
PI6 O2  C7   DOUB N N 3  
PI6 C3  C6   SING N N 4  
PI6 C3  H31  SING N N 5  
PI6 C3  H32  SING N N 6  
PI6 C3  H33A SING N N 7  
PI6 C4  C6   SING N N 8  
PI6 C4  H41A SING N N 9  
PI6 C4  H42  SING N N 10 
PI6 C4  H43  SING N N 11 
PI6 C5  C6   SING N N 12 
PI6 C5  H51  SING N N 13 
PI6 C5  H52  SING N N 14 
PI6 C5  H53  SING N N 15 
PI6 C7  N8   SING N N 16 
PI6 N8  C9   SING N N 17 
PI6 N8  H8   SING N N 18 
PI6 C9  C10  SING N N 19 
PI6 C9  C17  SING N N 20 
PI6 C9  H9   SING N N 21 
PI6 C10 C11  SING N N 22 
PI6 C10 H101 SING N N 23 
PI6 C10 H102 SING N N 24 
PI6 C11 C12  DOUB Y N 25 
PI6 C11 C13  SING Y N 26 
PI6 C12 C14  SING Y N 27 
PI6 C12 H12  SING N N 28 
PI6 C13 C15  DOUB Y N 29 
PI6 C13 H13  SING N N 30 
PI6 C14 C16  DOUB Y N 31 
PI6 C14 H14  SING N N 32 
PI6 C15 C16  SING Y N 33 
PI6 C15 H15  SING N N 34 
PI6 C16 H16  SING N N 35 
PI6 C17 O18  SING N N 36 
PI6 C17 C19  SING N N 37 
PI6 C17 H17  SING N N 38 
PI6 O18 H18  SING N N 39 
PI6 C19 N20  SING N N 40 
PI6 C19 H191 SING N N 41 
PI6 C19 H192 SING N N 42 
PI6 N20 C21  SING N N 43 
PI6 N20 H20  SING N N 44 
PI6 C21 C22  SING N N 45 
PI6 C21 C31  SING N N 46 
PI6 C21 H21  SING N N 47 
PI6 C22 C23  SING N N 48 
PI6 C22 H221 SING N N 49 
PI6 C22 H222 SING N N 50 
PI6 C23 C24  SING Y N 51 
PI6 C23 C26  DOUB Y N 52 
PI6 C24 C25  DOUB Y N 53 
PI6 C24 H24  SING N N 54 
PI6 C25 C28  SING Y N 55 
PI6 C25 H25  SING N N 56 
PI6 C26 C27  SING Y N 57 
PI6 C26 H26  SING N N 58 
PI6 C27 C28  DOUB Y N 59 
PI6 C27 H27  SING N N 60 
PI6 C28 O29  SING N N 61 
PI6 O29 C30  SING N N 62 
PI6 C30 C43  SING N N 63 
PI6 C30 H301 SING N N 64 
PI6 C30 H302 SING N N 65 
PI6 C31 O32  DOUB N N 66 
PI6 C31 N33  SING N N 67 
PI6 N33 C34  SING N N 68 
PI6 N33 H33  SING N N 69 
PI6 C34 C35  SING N N 70 
PI6 C34 C37  SING N N 71 
PI6 C34 H34  SING N N 72 
PI6 C35 O36  DOUB N N 73 
PI6 C35 N41  SING N N 74 
PI6 C37 C38  SING N N 75 
PI6 C37 C39  SING N N 76 
PI6 C37 H37  SING N N 77 
PI6 C38 C40  SING N N 78 
PI6 C38 H381 SING N N 79 
PI6 C38 H382 SING N N 80 
PI6 C39 H391 SING N N 81 
PI6 C39 H392 SING N N 82 
PI6 C39 H393 SING N N 83 
PI6 C40 H401 SING N N 84 
PI6 C40 H402 SING N N 85 
PI6 C40 H403 SING N N 86 
PI6 N41 C42  SING N N 87 
PI6 N41 H41  SING N N 88 
PI6 C42 C43  SING N N 89 
PI6 C42 H421 SING N N 90 
PI6 C42 H422 SING N N 91 
PI6 C43 H431 SING N N 92 
PI6 C43 H432 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              10.04 O=C(OC(C)(C)C)NC(Cc1ccccc1)C(O)CNC3C(=O)NC(C(=O)NCCCOc2ccc(cc2)C3)C(C)CC 
PI6 InChI            InChI                1.02b 
;InChI=1/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/f/h34,36-37H
;
PI6 InChIKey         InChI                1.02b RFUKEYSMPSCDLJ-PEKOINBIDZ 
PI6 SMILES_CANONICAL CACTVS               3.341 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               3.341 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" 1.5.0 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" 1.5.0 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              10.04 "tert-butyl [(1S,2R)-1-benzyl-2-hydroxy-3-{[(8S,11S)-8-[(1S)-1-methylpropyl]-7,10-dioxo-2-oxa-6,9-diazabicyclo[11.2.2]heptadeca-1(15),13,16-trien-11-yl]amino}propyl]carbamate"  
PI6 "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "tert-butyl N-[(2S,3R)-4-[[(3S,6S)-6-[(2S)-butan-2-yl]-4,7-dioxo-12-oxa-5,8-diazabicyclo[11.2.2]heptadeca-1(15),13,16-trien-3-yl]amino]-3-hydroxy-1-phenyl-butan-2-yl]carbamate" 
# 
