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                    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                        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 InChI            InChI                1.02b InChI=1/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                1.02b XOSFCMOTHZJUQK-OFVILXPXBW                                                                                                                                                           
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                                                                                                                          
# 
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 
# 
