data_CZP
#

_chem_comp.id                                   CZP
_chem_comp.name                                 
;(8R)-8-(CYCLOPENTYLMETHYL)-2-HYDROPEROXY-2-(4-HYDROXYBENZYL)-6-(4-HYDROXYPHENYL)-7,8-DIHYDROIMIDAZO[1,2-A]PYRAZIN-3(2H)
-ONE
;

_chem_comp.type                                 NON-POLYMER
_chem_comp.pdbx_type                            HETAIN
_chem_comp.formula                              "C25 H27 N3 O5"
_chem_comp.mon_nstd_parent_comp_id              ?
_chem_comp.pdbx_synonyms                        CP-COELENETERAZINE
_chem_comp.pdbx_formal_charge                   0
_chem_comp.pdbx_initial_date                    2003-07-07
_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                       449.499
_chem_comp.one_letter_code                      ?
_chem_comp.three_letter_code                    CZP
_chem_comp.pdbx_model_coordinates_details       ?
_chem_comp.pdbx_model_coordinates_missing_flag  Y
_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                 RCSB
#   #
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
CZP  O25   O25   O  0  1  N  N  N  -5.024  -3.418  -4.631   2.938   5.930   -0.259  O25   CZP   1  
CZP  C22   C22   C  0  1  Y  N  N  -4.175  -2.586  -4.093   2.723   4.977   -1.207  C22   CZP   2  
CZP  C23   C23   C  0  1  Y  N  N  -3.636  -1.550  -4.832   2.011   5.293   -2.364  C23   CZP   3  
CZP  C24   C24   C  0  1  Y  N  N  -2.775  -0.631  -4.301   1.790   4.316   -3.335  C24   CZP   4  
CZP  C21   C21   C  0  1  Y  N  N  -3.696  -2.713  -2.806   3.214   3.685   -1.021  C21   CZP   5  
CZP  C20   C20   C  0  1  Y  N  N  -2.797  -1.799  -2.267   2.993   2.708   -1.992  C20   CZP   6  
CZP  C19   C19   C  0  1  Y  N  N  -2.326  -0.757  -3.008   2.281   3.021   -3.152  C19   CZP   7  
CZP  C6    C6    C  0  1  N  N  N  -1.387   0.245  -2.473   2.048   1.989   -4.180  C6    CZP   8  
CZP  N7    N7    N  0  1  N  N  N  -1.137   1.320  -3.274   0.910   1.213   -4.078  N7    CZP   9  
CZP  C8    C8    C  0  1  N  N  N  -0.346   2.281  -2.914   0.589   0.107   -4.970  C8    CZP  10  
CZP  C26   C26   C  0  1  N  N  N  -0.072   3.466  -3.845   0.591  -1.193   -4.177  C26   CZP  11  
CZP  C27   C27   C  0  1  N  N  N   1.186   3.331  -4.625  -0.376  -1.141   -3.007  C27   CZP  12  
CZP  C28   C28   C  0  1  N  N  N   1.464   4.665  -5.285  -1.825  -0.930   -3.434  C28   CZP  13  
CZP  C29   C29   C  0  1  N  N  N   2.331   4.319  -6.473  -2.637  -1.364   -2.217  C29   CZP  14  
CZP  C30   C30   C  0  1  N  N  N   1.974   2.872  -6.832  -1.749  -2.334   -1.437  C30   CZP  15  
CZP  C31   C31   C  0  1  N  N  N   1.080   2.329  -5.735  -0.453  -2.453   -2.231  C31   CZP  16  
CZP  C9    C9    C  0  1  N  N  N   0.232   2.167  -1.585   1.588   0.025   -6.106  C9    CZP  17  
CZP  N4    N4    N  0  1  N  N  N  -0.024   1.124  -0.820   2.665   0.840   -6.123  N4    CZP  18  
CZP  C5    C5    C  0  1  N  N  N  -0.821   0.132  -1.218   2.921   1.802   -5.185  C5    CZP  19  
CZP  N1    N1    N  0  1  N  N  N   1.080   3.028  -1.007   1.479  -0.811   -7.092  N1    CZP  20  
CZP  C2    C2    C  0  1  N  N  S   1.458   2.543   0.304   2.674  -0.566   -7.940  C2    CZP  21  
CZP  C3    C3    C  0  1  N  N  N   0.665   1.256   0.346   3.414   0.558   -7.232  C3    CZP  22  
CZP  O18   O18   O  0  1  N  N  N   0.619   0.480   1.276   4.444   1.085   -7.622  O18   CZP  23  
CZP  O32   O32   O  0  1  N  N  N   0.920   3.311   1.399   2.434  -0.147   -9.274  O32   CZP  24  
CZP  C10   C10   C  0  1  N  N  N   2.987   2.459   0.267   3.524  -1.828   -7.969  C10   CZP  25  
CZP  C11   C11   C  0  1  Y  N  N   3.596   1.853   1.525   2.819  -2.962   -8.665  C11   CZP  26  
CZP  C12   C12   C  0  1  Y  N  N   4.067   0.536   1.520   2.019  -3.824   -7.928  C12   CZP  27  
CZP  C13   C13   C  0  1  Y  N  N   4.642  -0.014   2.675   1.366  -4.874   -8.573  C13   CZP  28  
CZP  C14   C14   C  0  1  Y  N  N   4.752   0.765   3.853   1.519  -5.052   -9.948  C14   CZP  29  
CZP  O17   O17   O  0  1  N  N  N   5.229   0.342   4.958   0.883  -6.078  -10.576  O17   CZP  30  
CZP  C15   C15   C  0  1  Y  N  N   4.298   2.072   3.824   2.325  -4.179  -10.678  C15   CZP  31  
CZP  C16   C16   C  0  1  Y  N  N   3.714   2.611   2.658   2.978  -3.128  -10.034  C16   CZP  32  
CZP  O1    O1    O  0  1  N  N  N       ?       ?       ?   1.629   1.058   -9.158  O1    CZP  33  
CZP  H25   H25   H  0  1  N  N  N  -5.394  -4.130  -4.123   2.231   5.909    0.406  H25   CZP  34  
CZP  H23   H23   H  0  1  N  N  N  -3.906  -1.452  -5.897   1.626   6.298   -2.515  H23   CZP  35  
CZP  H24   H24   H  0  1  N  N  N  -2.440   0.218  -4.920   1.234   4.578   -4.232  H24   CZP  36  
CZP  H21   H21   H  0  1  N  N  N  -4.039  -3.564  -2.194   3.769   3.433   -0.121  H21   CZP  37  
CZP  H20   H20   H  0  1  N  N  N  -2.449  -1.903  -1.226   3.383   1.706   -1.833  H20   CZP  38  
CZP  HN7   HN7   H  0  1  N  N  N  -2.034   1.735  -3.524   0.285   1.403   -3.302  HN7   CZP  39  
CZP  H8    H8    H  0  1  N  N  N   0.244   3.087  -3.409  -0.405   0.264   -5.402  H8    CZP  40  
CZP  H261  1H26  H  0  0  N  N  N  -0.082   4.425  -3.276   0.318  -2.020   -4.839  H261  CZP  41  
CZP  H262  2H26  H  0  0  N  N  N  -0.939   3.643  -4.523   1.602  -1.388   -3.806  H262  CZP  42  
CZP  H27   H27   H  0  1  N  N  N   1.982   3.002  -3.918  -0.072  -0.333   -2.331  H27   CZP  43  
CZP  H281  1H28  H  0  0  N  N  N   1.907   5.428  -4.603  -2.074  -1.567   -4.292  H281  CZP  44  
CZP  H282  2H28  H  0  0  N  N  N   0.548   5.247  -5.542  -2.031   0.107   -3.715  H282  CZP  45  
CZP  H291  1H29  H  0  0  N  N  N   3.420   4.482  -6.296  -3.583  -1.827   -2.515  H291  CZP  46  
CZP  H292  2H29  H  0  0  N  N  N   2.229   5.031  -7.325  -2.879  -0.497   -1.591  H292  CZP  47  
CZP  H301  1H30  H  0  0  N  N  N   2.873   2.237  -7.012  -1.547  -1.931   -0.437  H301  CZP  48  
CZP  H302  2H30  H  0  0  N  N  N   1.520   2.777  -7.846  -2.228  -3.310   -1.306  H302  CZP  49  
CZP  H311  1H31  H  0  0  N  N  N   0.034   2.124  -6.062   0.415  -2.605   -1.582  H311  CZP  50  
CZP  H312  2H31  H  0  0  N  N  N   1.323   1.285  -5.428  -0.515  -3.306   -2.918  H312  CZP  51  
CZP  H5    H5    H  0  1  N  N  N  -1.001  -0.728  -0.551   3.825   2.388   -5.308  H5    CZP  52  
CZP  H101  1H10  H  0  0  N  N  N   3.431   3.460   0.057   3.780  -2.124   -6.945  H101  CZP  53  
CZP  H102  2H10  H  0  0  N  N  N   3.329   1.909  -0.640   4.476  -1.620   -8.472  H102  CZP  54  
CZP  H12   H12   H  0  1  N  N  N   3.985  -0.071   0.603   1.894  -3.693   -6.857  H12   CZP  55  
CZP  H13   H13   H  0  1  N  N  N   5.006  -1.055   2.657   0.740  -5.551   -7.998  H13   CZP  56  
CZP  H17   H17   H  0  1  N  N  N   5.303   0.864   5.748   0.519  -6.698   -9.924  H17   CZP  57  
CZP  H15   H15   H  0  1  N  N  N   4.402   2.687   4.734   2.449  -4.312  -11.750  H15   CZP  58  
CZP  H16   H16   H  0  1  N  N  N   3.341   3.649   2.632   3.604  -2.453  -10.611  H16   CZP  59  
CZP  HO1   HO1   H  0  1  N  N  N  -0.354   0.506   0.722   0.776   0.625   -9.335  HO1   CZP  60  
#   #
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
CZP  O25  C22   SING  N  N   1  
CZP  O25  H25   SING  N  N   2  
CZP  C22  C23   DOUB  Y  N   3  
CZP  C22  C21   SING  Y  N   4  
CZP  C23  C24   SING  Y  N   5  
CZP  C23  H23   SING  N  N   6  
CZP  C24  C19   DOUB  Y  N   7  
CZP  C24  H24   SING  N  N   8  
CZP  C21  C20   DOUB  Y  N   9  
CZP  C21  H21   SING  N  N  10  
CZP  C20  C19   SING  Y  N  11  
CZP  C20  H20   SING  N  N  12  
CZP  C19  C6    SING  N  N  13  
CZP  C6   N7    SING  N  N  14  
CZP  C6   C5    DOUB  N  N  15  
CZP  N7   C8    SING  N  N  16  
CZP  N7   HN7   SING  N  N  17  
CZP  C8   C26   SING  N  N  18  
CZP  C8   C9    SING  N  N  19  
CZP  C8   H8    SING  N  N  20  
CZP  C26  C27   SING  N  N  21  
CZP  C26  H261  SING  N  N  22  
CZP  C26  H262  SING  N  N  23  
CZP  C27  C28   SING  N  N  24  
CZP  C27  C31   SING  N  N  25  
CZP  C27  H27   SING  N  N  26  
CZP  C28  C29   SING  N  N  27  
CZP  C28  H281  SING  N  N  28  
CZP  C28  H282  SING  N  N  29  
CZP  C29  C30   SING  N  N  30  
CZP  C29  H291  SING  N  N  31  
CZP  C29  H292  SING  N  N  32  
CZP  C30  C31   SING  N  N  33  
CZP  C30  H301  SING  N  N  34  
CZP  C30  H302  SING  N  N  35  
CZP  C31  H311  SING  N  N  36  
CZP  C31  H312  SING  N  N  37  
CZP  C9   N4    SING  N  N  38  
CZP  C9   N1    DOUB  N  N  39  
CZP  N4   C5    SING  N  N  40  
CZP  N4   C3    SING  N  N  41  
CZP  C5   H5    SING  N  N  42  
CZP  N1   C2    SING  N  N  43  
CZP  C2   C3    SING  N  N  44  
CZP  C2   O32   SING  N  N  45  
CZP  C2   C10   SING  N  N  46  
CZP  C3   O18   DOUB  N  N  47  
CZP  O32  O1    SING  N  N  48  
CZP  C10  C11   SING  N  N  49  
CZP  C10  H101  SING  N  N  50  
CZP  C10  H102  SING  N  N  51  
CZP  C11  C12   DOUB  Y  N  52  
CZP  C11  C16   SING  Y  N  53  
CZP  C12  C13   SING  Y  N  54  
CZP  C12  H12   SING  N  N  55  
CZP  C13  C14   DOUB  Y  N  56  
CZP  C13  H13   SING  N  N  57  
CZP  C14  O17   SING  N  N  58  
CZP  C14  C15   SING  Y  N  59  
CZP  O17  H17   SING  N  N  60  
CZP  C15  C16   DOUB  Y  N  61  
CZP  C15  H15   SING  N  N  62  
CZP  C16  H16   SING  N  N  63  
CZP  O1   HO1   SING  N  N  64  
#   #
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
CZP  SMILES            ACDLabs               10.04  "O=C1N3C=C(NC(C3=NC1(OO)Cc2ccc(O)cc2)CC4CCCC4)c5ccc(O)cc5"  
CZP  SMILES_CANONICAL  CACTVS                3.341  "OO[C@]1(Cc2ccc(O)cc2)N=C3[C@H](CC4CCCC4)NC(=CN3C1=O)c5ccc(O)cc5"  
CZP  SMILES            CACTVS                3.341  "OO[C]1(Cc2ccc(O)cc2)N=C3[CH](CC4CCCC4)NC(=CN3C1=O)c5ccc(O)cc5"  
CZP  SMILES_CANONICAL  "OpenEye OEToolkits"  1.5.0  "c1cc(ccc1C[C@@]2(C(=O)N3C=C(NC(C3=N2)CC4CCCC4)c5ccc(cc5)O)OO)O"  
CZP  SMILES            "OpenEye OEToolkits"  1.5.0  "c1cc(ccc1CC2(C(=O)N3C=C(NC(C3=N2)CC4CCCC4)c5ccc(cc5)O)OO)O"  
CZP  InChI             InChI                 1.03   "InChI=1S/C25H27N3O5/c29-19-9-5-17(6-10-19)14-25(33-32)24(31)28-15-22(18-7-11-20(30)12-8-18)26-21(23(28)27-25)13-16-3-1-2-4-16/h5-12,15-16,21,26,29-30,32H,1-4,13-14H2/t21-,25-/m0/s1"  
CZP  InChIKey          InChI                 1.03   XOSFCMOTHZJUQK-OFVILXPXSA-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
CZP  "SYSTEMATIC NAME"  ACDLabs               10.04  "(2S,8S)-8-(cyclopentylmethyl)-2-hydroperoxy-2-(4-hydroxybenzyl)-6-(4-hydroxyphenyl)-7,8-dihydroimidazo[1,2-a]pyrazin-3(2H)-one"  
CZP  "SYSTEMATIC NAME"  "OpenEye OEToolkits"  1.5.0  "(2S)-8-(cyclopentylmethyl)-2-hydroperoxy-6-(4-hydroxyphenyl)-2-[(4-hydroxyphenyl)methyl]-7,8-dihydroimidazo[3,2-a]pyrazin-3-one"  
#   #
loop_
_pdbx_chem_comp_audit.comp_id
_pdbx_chem_comp_audit.action_type
_pdbx_chem_comp_audit.date
_pdbx_chem_comp_audit.processing_site
CZP  "Create component"   2003-07-07  RCSB  
CZP  "Modify descriptor"  2011-06-04  RCSB  
CZP  "Modify synonyms"    2020-06-05  PDBE  
#
_pdbx_chem_comp_synonyms.ordinal     1
_pdbx_chem_comp_synonyms.comp_id     CZP
_pdbx_chem_comp_synonyms.name        CP-COELENETERAZINE
_pdbx_chem_comp_synonyms.provenance  ?
_pdbx_chem_comp_synonyms.type        ?
##
