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                   2020-06-17
_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  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"  
PI2  InChI             InChI                 1.03   "InChI=1S/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"  
PI2  InChIKey          InChI                 1.03   SCRDVDSVEKGWGQ-SLFFLAALSA-N  
#   #
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"  
#   #
loop_
_pdbx_chem_comp_audit.comp_id
_pdbx_chem_comp_audit.action_type
_pdbx_chem_comp_audit.date
_pdbx_chem_comp_audit.processing_site
PI2  "Create component"   1999-07-08  PDBJ  
PI2  "Modify descriptor"  2011-06-04  RCSB  
PI2  "Modify synonyms"    2020-06-05  PDBE  
#
_pdbx_chem_comp_synonyms.ordinal     1
_pdbx_chem_comp_synonyms.comp_id     PI2
_pdbx_chem_comp_synonyms.name        "MACROCYCLIC PEPTIDOMIMETIC INHIBITOR 2"
_pdbx_chem_comp_synonyms.provenance  ?
_pdbx_chem_comp_synonyms.type        ?
##
