data_PI2
# 
_chem_comp.id                                    PI2 
_chem_comp.name                                  "2-{11-[1-HYDROXY-2-(3-METHYL-BUTYLAMINO)-ETHYL] -6,9-DIOXO-2-OXA-7,10-DIAZA-BICYCLO[11.2.2]HEPTADECA- 1(16),13(17),14-TRIEN-8-YL}-ACETAMIDE" 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C23 H36 N4 O5" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         "MACROCYCLIC PEPTIDOMIMETIC INHIBITOR 2" 
_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                        448.556 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     PI2 
_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 
PI2 C1   C1   C 0 1 N N N 5.847 4.076  9.162  1.137  -0.725 -5.140 C1   PI2 1  
PI2 C2   C2   C 0 1 N N N 3.998 3.228  10.678 1.961  -0.301 -2.840 C2   PI2 2  
PI2 O3   O3   O 0 1 N N N 3.995 4.070  11.577 2.109  -1.452 -2.488 O3   PI2 3  
PI2 C4   C4   C 0 1 N N N 4.408 3.611  9.265  2.119  0.082  -4.289 C4   PI2 4  
PI2 N5   N5   N 0 1 N N N 3.670 1.953  10.875 1.649  0.667  -1.932 N5   PI2 5  
PI2 C6   C6   C 0 1 N N S 3.229 1.455  12.190 1.507  0.217  -0.530 C6   PI2 6  
PI2 C7   C7   C 0 1 N N N 4.078 0.320  12.744 0.214  0.757  0.023  C7   PI2 7  
PI2 O8   O8   O 0 1 N N N 4.035 -0.810 12.248 0.182  1.863  0.520  O8   PI2 8  
PI2 C9   C9   C 0 1 N N N 1.766 1.037  12.096 2.682  0.742  0.297  C9   PI2 9  
PI2 C10  C10  C 0 1 N N N 0.891 2.155  11.586 3.973  0.211  -0.270 C10  PI2 10 
PI2 O11  O11  O 0 1 N N N 0.490 3.025  12.349 3.956  -0.514 -1.241 O11  PI2 11 
PI2 N12  N12  N 0 1 N N N 0.651 2.179  10.278 5.148  0.544  0.301  N12  PI2 12 
PI2 N13  N13  N 0 1 N N N 4.830 0.629  13.797 -0.907 0.012  -0.032 N13  PI2 13 
PI2 C14  C14  C 0 1 N N S 5.727 -0.342 14.444 -2.168 0.530  0.503  C14  PI2 14 
PI2 C15  C15  C 0 1 N N N 7.155 0.202  14.374 -3.310 0.161  -0.448 C15  PI2 15 
PI2 C16  C16  C 0 1 Y N N 7.436 0.889  13.062 -2.756 -0.015 -1.839 C16  PI2 16 
PI2 C17  C17  C 0 1 Y N N 7.369 2.278  12.959 -2.344 1.090  -2.561 C17  PI2 17 
PI2 C18  C18  C 0 1 Y N N 7.523 2.913  11.743 -1.830 0.932  -3.833 C18  PI2 18 
PI2 C19  C19  C 0 1 Y N N 7.675 0.151  11.906 -2.660 -1.279 -2.389 C19  PI2 19 
PI2 C20  C20  C 0 1 Y N N 7.829 0.774  10.683 -2.146 -1.441 -3.662 C20  PI2 20 
PI2 C21  C21  C 0 1 Y N N 7.751 2.154  10.606 -1.727 -0.335 -4.386 C21  PI2 21 
PI2 O22  O22  O 0 1 N N N 7.881 2.777  9.388  -1.216 -0.493 -5.636 O22  PI2 22 
PI2 C23  C23  C 0 1 N N N 6.724 2.972  8.596  0.034  0.197  -5.660 C23  PI2 23 
PI2 C24  C24  C 0 1 N N R 5.326 -0.614 15.909 -2.430 -0.084 1.879  C24  PI2 24 
PI2 O25  O25  O 0 1 N N N 5.371 0.604  16.657 -3.662 0.419  2.399  O25  PI2 25 
PI2 C26  C26  C 0 1 N N N 6.264 -1.635 16.549 -1.287 0.282  2.827  C26  PI2 26 
PI2 N27  N27  N 0 1 N N N 6.107 -2.979 15.978 -1.539 -0.308 4.149  N27  PI2 27 
PI2 C28  C28  C 0 1 N N N 5.461 -3.765 17.040 -0.411 0.079  5.006  C28  PI2 28 
PI2 C29  C29  C 0 1 N N N 4.249 -4.299 16.342 -0.609 -0.505 6.406  C29  PI2 29 
PI2 C30  C30  C 0 1 N N N 3.010 -4.341 17.217 0.564  -0.101 7.299  C30  PI2 30 
PI2 C31  C31  C 0 1 N N N 1.813 -4.531 16.315 0.366  -0.686 8.699  C31  PI2 31 
PI2 C32  C32  C 0 1 N N N 3.126 -5.466 18.224 1.867  -0.637 6.702  C32  PI2 32 
PI2 H11  1H1  H 0 1 N N N 5.936 5.019  8.574  0.694  -1.515 -4.533 H11  PI2 33 
PI2 H12  2H1  H 0 1 N N N 6.232 4.451  10.138 1.667  -1.169 -5.983 H12  PI2 34 
PI2 H41  1H4  H 0 1 N N N 3.714 4.376  8.845  3.139  -0.129 -4.612 H41  PI2 35 
PI2 H42  2H4  H 0 1 N N N 4.210 2.774  8.555  1.914  1.145  -4.408 H42  PI2 36 
PI2 HN5  HN5  H 0 1 N N N 3.754 1.372  10.040 1.529  1.594  -2.189 HN5  PI2 37 
PI2 H6   H6   H 0 1 N N N 3.355 2.292  12.914 1.493  -0.871 -0.496 H6   PI2 38 
PI2 H91  1H9  H 0 1 N N N 1.647 0.116  11.478 2.691  1.831  0.265  H91  PI2 39 
PI2 H92  2H9  H 0 1 N N N 1.393 0.644  13.070 2.576  0.409  1.330  H92  PI2 40 
PI2 H121 1H12 H 0 0 N N N 0.985 1.454  9.642  5.979  0.202  -0.063 H121 PI2 41 
PI2 H122 2H12 H 0 0 N N N 0.059 2.934  9.933  5.162  1.124  1.078  H122 PI2 42 
PI2 H13  H13  H 0 1 N N N 4.720 1.595  14.103 -0.880 -0.871 -0.430 H13  PI2 43 
PI2 H14  H14  H 0 1 N N N 5.652 -1.315 13.905 -2.107 1.615  0.594  H14  PI2 44 
PI2 H151 1H15 H 0 0 N N N 7.374 0.873  15.236 -3.772 -0.769 -0.119 H151 PI2 45 
PI2 H152 2H15 H 0 0 N N N 7.903 -0.599 14.579 -4.054 0.958  -0.450 H152 PI2 46 
PI2 H17  H17  H 0 1 N N N 7.190 2.888  13.860 -2.425 2.076  -2.129 H17  PI2 47 
PI2 H18  H18  H 0 1 N N N 7.464 4.012  11.680 -1.509 1.795  -4.397 H18  PI2 48 
PI2 H19  H19  H 0 1 N N N 7.743 -0.948 11.960 -2.986 -2.140 -1.825 H19  PI2 49 
PI2 H20  H20  H 0 1 N N N 8.012 0.174  9.775  -2.072 -2.429 -4.092 H20  PI2 50 
PI2 H231 1H23 H 0 0 N N N 6.153 2.023  8.464  0.263  0.497  -6.683 H231 PI2 51 
PI2 H232 2H23 H 0 0 N N N 6.985 3.163  7.529  -0.027 1.082  -5.027 H232 PI2 52 
PI2 H24  H24  H 0 1 N N N 4.289 -1.025 15.917 -2.491 -1.169 1.786  H24  PI2 53 
PI2 H25  H25  H 0 1 N N N 5.124 0.436  17.558 -3.565 1.378  2.465  H25  PI2 54 
PI2 H261 1H26 H 0 0 N N N 7.324 -1.296 16.491 -1.226 1.366  2.920  H261 PI2 55 
PI2 H262 2H26 H 0 0 N N N 6.141 -1.653 17.657 -0.348 -0.102 2.430  H262 PI2 56 
PI2 H27  H27  H 0 1 N N N 6.975 -3.386 15.631 -1.484 -1.309 4.034  H27  PI2 57 
PI2 H281 1H28 H 0 0 N N N 6.109 -4.537 17.516 -0.361 1.166  5.071  H281 PI2 58 
PI2 H282 2H28 H 0 0 N N N 5.254 -3.205 17.981 0.516  -0.302 4.581  H282 PI2 59 
PI2 H291 1H29 H 0 0 N N N 4.050 -3.726 15.405 -0.659 -1.592 6.341  H291 PI2 60 
PI2 H292 2H29 H 0 0 N N N 4.456 -5.303 15.906 -1.537 -0.124 6.831  H292 PI2 61 
PI2 H30  H30  H 0 1 N N N 2.896 -3.391 17.791 0.614  0.985  7.364  H30  PI2 62 
PI2 H311 1H31 H 0 0 N N N 0.902 -4.561 16.958 1.203  -0.398 9.335  H311 PI2 63 
PI2 H312 2H31 H 0 0 N N N 1.749 -3.759 15.512 -0.561 -0.304 9.124  H312 PI2 64 
PI2 H313 3H31 H 0 0 N N N 1.906 -5.424 15.654 0.316  -1.773 8.634  H313 PI2 65 
PI2 H321 1H32 H 0 0 N N N 2.215 -5.496 18.867 1.817  -1.724 6.638  H321 PI2 66 
PI2 H322 2H32 H 0 0 N N N 3.324 -6.447 17.733 2.009  -0.220 5.705  H322 PI2 67 
PI2 H323 3H32 H 0 0 N N N 4.061 -5.392 18.826 2.704  -0.348 7.338  H323 PI2 68 
# 
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 
PI2 C1  C4   SING N N 1  
PI2 C1  C23  SING N N 2  
PI2 C1  H11  SING N N 3  
PI2 C1  H12  SING N N 4  
PI2 C2  O3   DOUB N N 5  
PI2 C2  C4   SING N N 6  
PI2 C2  N5   SING N N 7  
PI2 C4  H41  SING N N 8  
PI2 C4  H42  SING N N 9  
PI2 N5  C6   SING N N 10 
PI2 N5  HN5  SING N N 11 
PI2 C6  C7   SING N N 12 
PI2 C6  C9   SING N N 13 
PI2 C6  H6   SING N N 14 
PI2 C7  O8   DOUB N N 15 
PI2 C7  N13  SING N N 16 
PI2 C9  C10  SING N N 17 
PI2 C9  H91  SING N N 18 
PI2 C9  H92  SING N N 19 
PI2 C10 O11  DOUB N N 20 
PI2 C10 N12  SING N N 21 
PI2 N12 H121 SING N N 22 
PI2 N12 H122 SING N N 23 
PI2 N13 C14  SING N N 24 
PI2 N13 H13  SING N N 25 
PI2 C14 C15  SING N N 26 
PI2 C14 C24  SING N N 27 
PI2 C14 H14  SING N N 28 
PI2 C15 C16  SING N N 29 
PI2 C15 H151 SING N N 30 
PI2 C15 H152 SING N N 31 
PI2 C16 C17  SING Y N 32 
PI2 C16 C19  DOUB Y N 33 
PI2 C17 C18  DOUB Y N 34 
PI2 C17 H17  SING N N 35 
PI2 C18 C21  SING Y N 36 
PI2 C18 H18  SING N N 37 
PI2 C19 C20  SING Y N 38 
PI2 C19 H19  SING N N 39 
PI2 C20 C21  DOUB Y N 40 
PI2 C20 H20  SING N N 41 
PI2 C21 O22  SING N N 42 
PI2 O22 C23  SING N N 43 
PI2 C23 H231 SING N N 44 
PI2 C23 H232 SING N N 45 
PI2 C24 O25  SING N N 46 
PI2 C24 C26  SING N N 47 
PI2 C24 H24  SING N N 48 
PI2 O25 H25  SING N N 49 
PI2 C26 N27  SING N N 50 
PI2 C26 H261 SING N N 51 
PI2 C26 H262 SING N N 52 
PI2 N27 C28  SING N N 53 
PI2 N27 H27  SING N N 54 
PI2 C28 C29  SING N N 55 
PI2 C28 H281 SING N N 56 
PI2 C28 H282 SING N N 57 
PI2 C29 C30  SING N N 58 
PI2 C29 H291 SING N N 59 
PI2 C29 H292 SING N N 60 
PI2 C30 C31  SING N N 61 
PI2 C30 C32  SING N N 62 
PI2 C30 H30  SING N N 63 
PI2 C31 H311 SING N N 64 
PI2 C31 H312 SING N N 65 
PI2 C31 H313 SING N N 66 
PI2 C32 H321 SING N N 67 
PI2 C32 H322 SING N N 68 
PI2 C32 H323 SING N N 69 
# 
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 
PI2 SMILES           ACDLabs              10.04 O=C1NC(C(O)CNCCC(C)C)Cc2ccc(OCCCC(=O)NC1CC(=O)N)cc2 
PI2 InChI            InChI                1.02b 
InChI=1/C23H36N4O5/c1-15(2)9-10-25-14-20(28)18-12-16-5-7-17(8-6-16)32-11-3-4-22(30)26-19(13-21(24)29)23(31)27-18/h5-8,15,18-20,25,28H,3-4,9-14H2,1-2H3,(H2,24,29)(H,26,30)(H,27,31)/t18-,19-,20+/m0/s1/f/h26-27H,24H2 
PI2 InChIKey         InChI                1.02b SCRDVDSVEKGWGQ-NYFAVRRRDL 
PI2 SMILES_CANONICAL CACTVS               3.341 CC(C)CCNC[C@@H](O)[C@@H]1Cc2ccc(OCCCC(=O)N[C@@H](CC(N)=O)C(=O)N1)cc2 
PI2 SMILES           CACTVS               3.341 CC(C)CCNC[CH](O)[CH]1Cc2ccc(OCCCC(=O)N[CH](CC(N)=O)C(=O)N1)cc2 
PI2 SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 CC(C)CCNC[C@H]([C@@H]1Cc2ccc(cc2)OCCCC(=O)N[C@H](C(=O)N1)CC(=O)N)O 
PI2 SMILES           "OpenEye OEToolkits" 1.5.0 CC(C)CCNCC(C1Cc2ccc(cc2)OCCCC(=O)NC(C(=O)N1)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 
PI2 "SYSTEMATIC NAME" ACDLabs              10.04 2-[(8S,11S)-11-{(1R)-1-hydroxy-2-[(3-methylbutyl)amino]ethyl}-6,9-dioxo-2-oxa-7,10-diazabicyclo[11.2.2]heptadeca-1(15),13,16-trien-8-yl]acetamide 
PI2 "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 2-[(3S,6S)-3-[(1R)-1-hydroxy-2-(3-methylbutylamino)ethyl]-5,8-dioxo-12-oxa-4,7-diazabicyclo[11.2.2]heptadeca-1(15),13,16-trien-6-yl]ethanamide    
# 
