data_CZN
# 
_chem_comp.id                                    CZN 
_chem_comp.name                                  (2S,8R)-8-BENZYL-2-HYDROPEROXY-6-(4-HYDROXYPHENYL)-2-(2-NAPHTHYLMETHYL)-7,8-DIHYDROIMIDAZO[1,2-A]PYRAZIN-3(2H)-ONE 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C30 H25 N3 O4" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         N-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                        491.537 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     CZN 
_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        1UHK 
_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 
CZN O21  O21  O 0 1 N N N -0.978 1.121  0.692  -0.794 2.897  -1.898 O21  CZN 1  
CZN C3   C3   C 0 1 N N N -0.994 0.195  1.479  -0.468 1.930  -1.243 C3   CZN 2  
CZN N4   N4   N 0 1 N N N -0.253 -0.943 1.311  -1.272 1.082  -0.579 N4   CZN 3  
CZN C5   C5   C 0 1 N N N 0.610  -1.266 0.322  -2.673 1.115  -0.487 C5   CZN 4  
CZN C9   C9   C 0 1 N N N -0.482 -1.759 2.328  -0.527 0.099  0.055  C9   CZN 5  
CZN C8   C8   C 0 1 N N S 0.192  -3.061 2.375  -1.230 -0.976 0.872  C8   CZN 6  
CZN N7   N7   N 0 1 N N N 1.027  -3.346 1.397  -2.456 -0.334 1.393  N7   CZN 7  
CZN C6   C6   C 0 1 N N N 1.247  -2.519 0.373  -3.256 0.398  0.496  C6   CZN 8  
CZN C22  C22  C 0 1 Y N N 2.243  -2.956 -0.648 -4.728 0.382  0.629  C22  CZN 9  
CZN C23  C23  C 0 1 Y N N 2.801  -4.227 -0.574 -5.449 1.577  0.585  C23  CZN 10 
CZN C24  C24  C 0 1 Y N N 3.724  -4.687 -1.504 -6.821 1.557  0.710  C24  CZN 11 
CZN C25  C25  C 0 1 Y N N 4.115  -3.877 -2.546 -7.488 0.350  0.879  C25  CZN 12 
CZN C26  C26  C 0 1 Y N N 3.579  -2.615 -2.615 -6.775 -0.840 0.923  C26  CZN 13 
CZN C27  C27  C 0 1 Y N N 2.643  -2.147 -1.695 -5.402 -0.830 0.794  C27  CZN 14 
CZN O28  O28  O 0 1 N N N 5.045  -4.336 -3.448 -8.841 0.335  1.001  O28  CZN 15 
CZN C29  C29  C 0 1 N N N -0.001 -4.014 3.525  -1.589 -2.167 -0.019 C29  CZN 16 
CZN C30  C30  C 0 1 Y N N -0.851 -5.193 3.220  -0.326 -2.827 -0.510 C30  CZN 17 
CZN C31  C31  C 0 1 Y N N -2.044 -5.337 3.912  0.320  -3.758 0.281  C31  CZN 18 
CZN C32  C32  C 0 1 Y N N -2.847 -6.426 3.657  1.479  -4.362 -0.169 C32  CZN 19 
CZN C33  C33  C 0 1 Y N N -2.484 -7.349 2.704  1.990  -4.037 -1.411 C33  CZN 20 
CZN C34  C34  C 0 1 Y N N -1.299 -7.193 2.010  1.343  -3.107 -2.203 C34  CZN 21 
CZN C35  C35  C 0 1 Y N N -0.470 -6.113 2.260  0.183  -2.505 -1.754 C35  CZN 22 
CZN N1   N1   N 0 1 N N N -1.364 -1.248 3.188  0.731  0.229  -0.139 N1   CZN 23 
CZN C2   C2   C 0 1 N N S -1.789 0.076  2.761  0.936  1.411  -0.992 C2   CZN 24 
CZN O36  O36  O 0 1 N N N -1.243 1.062  3.636  1.561  1.040  -2.222 O36  CZN 25 
CZN O37  O37  O 0 1 N N N -0.006 0.887  3.937  0.638  0.128  -2.909 O37  CZN 26 
CZN C10  C10  C 0 1 N N N -3.304 0.122  2.715  1.774  2.462  -0.261 C10  CZN 27 
CZN C11  C11  C 0 1 Y N N -3.803 1.515  2.369  3.146  1.904  0.019  C11  CZN 28 
CZN C12  C12  C 0 1 Y N N -4.209 1.783  1.081  3.375  1.243  1.187  C12  CZN 29 
CZN C13  C13  C 0 1 Y N N -4.690 3.057  0.745  4.651  0.717  1.449  C13  CZN 30 
CZN C14  C14  C 0 1 Y N N -5.074 3.373  -0.551 4.924  0.024  2.640  C14  CZN 31 
CZN C18  C18  C 0 1 Y N N -4.741 4.080  1.811  5.685  0.894  0.496  C18  CZN 32 
CZN C19  C19  C 0 1 Y N N -4.301 3.770  3.084  5.412  1.588  -0.696 C19  CZN 33 
CZN C20  C20  C 0 1 Y N N -3.862 2.481  3.365  4.163  2.079  -0.918 C20  CZN 34 
CZN C17  C17  C 0 1 Y N N -5.205 5.356  1.490  6.963  0.373  0.761  C17  CZN 35 
CZN C16  C16  C 0 1 Y N N -5.602 5.637  0.185  7.190  -0.293 1.926  C16  CZN 36 
CZN C15  C15  C 0 1 Y N N -5.548 4.654  -0.834 6.174  -0.467 2.863  C15  CZN 37 
CZN H5   H5   H 0 1 N N N 0.786  -0.540 -0.490 -3.264 1.695  -1.180 H5   CZN 38 
CZN H8   H8   H 0 1 N N N -0.652 -3.762 2.574  -0.594 -1.300 1.696  H8   CZN 39 
CZN HN7  HN7  H 0 1 N N N 0.749  -4.247 1.009  -2.702 -0.416 2.328  HN7  CZN 40 
CZN H23  H23  H 0 1 N N N 2.501  -4.894 0.252  -4.931 2.515  0.454  H23  CZN 41 
CZN H24  H24  H 0 1 N N N 4.149  -5.701 -1.415 -7.379 2.481  0.676  H24  CZN 42 
CZN H26  H26  H 0 1 N N N 3.911  -1.956 -3.435 -7.297 -1.777 1.055  H26  CZN 43 
CZN H27  H27  H 0 1 N N N 2.218  -1.134 -1.796 -4.849 -1.756 0.828  H27  CZN 44 
CZN H28  H28  H 0 1 N N N 5.315  -3.777 -4.167 -9.202 0.249  0.108  H28  CZN 45 
CZN H291 1H29 H 0 0 N N N -0.398 -3.471 4.414  -2.175 -2.886 0.554  H291 CZN 46 
CZN H292 2H29 H 0 0 N N N 0.987  -4.343 3.924  -2.173 -1.820 -0.871 H292 CZN 47 
CZN H31  H31  H 0 1 N N N -2.353 -4.589 4.662  -0.080 -4.012 1.252  H31  CZN 48 
CZN H32  H32  H 0 1 N N N -3.786 -6.560 4.219  1.984  -5.089 0.450  H32  CZN 49 
CZN H33  H33  H 0 1 N N N -3.141 -8.211 2.497  2.896  -4.509 -1.763 H33  CZN 50 
CZN H34  H34  H 0 1 N N N -1.012 -7.938 1.249  1.743  -2.852 -3.173 H34  CZN 51 
CZN H35  H35  H 0 1 N N N 0.475  -5.988 1.705  -0.323 -1.778 -2.373 H35  CZN 52 
CZN H37  H37  H 0 1 N N N 0.358  1.544  4.520  1.061  -0.124 -3.742 H37  CZN 53 
CZN H101 1H10 H 0 0 N N N -3.754 -0.250 3.665  1.864  3.352  -0.884 H101 CZN 54 
CZN H102 2H10 H 0 0 N N N -3.716 -0.645 2.019  1.289  2.724  0.679  H102 CZN 55 
CZN H12  H12  H 0 1 N N N -4.149 0.983  0.324  2.578  1.120  1.906  H12  CZN 56 
CZN H14  H14  H 0 1 N N N -5.003 2.614  -1.348 4.146  -0.119 3.375  H14  CZN 57 
CZN H19  H19  H 0 1 N N N -4.300 4.545  3.869  6.190  1.730  -1.431 H19  CZN 58 
CZN H20  H20  H 0 1 N N N -3.556 2.221  4.392  3.956  2.611  -1.834 H20  CZN 59 
CZN H17  H17  H 0 1 N N N -5.258 6.139  2.265  7.760  0.500  0.044  H17  CZN 60 
CZN H16  H16  H 0 1 N N N -5.964 6.653  -0.045 8.173  -0.692 2.127  H16  CZN 61 
CZN H15  H15  H 0 1 N N N -5.879 4.889  -1.860 6.381  -1.000 3.779  H15  CZN 62 
# 
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 
CZN O21 C3   DOUB N N 1  
CZN C3  N4   SING N N 2  
CZN C3  C2   SING N N 3  
CZN N4  C5   SING N N 4  
CZN N4  C9   SING N N 5  
CZN C5  C6   DOUB N N 6  
CZN C5  H5   SING N N 7  
CZN C9  C8   SING N N 8  
CZN C9  N1   DOUB N N 9  
CZN C8  N7   SING N N 10 
CZN C8  C29  SING N N 11 
CZN C8  H8   SING N N 12 
CZN N7  C6   SING N N 13 
CZN N7  HN7  SING N N 14 
CZN C6  C22  SING N N 15 
CZN C22 C23  DOUB Y N 16 
CZN C22 C27  SING Y N 17 
CZN C23 C24  SING Y N 18 
CZN C23 H23  SING N N 19 
CZN C24 C25  DOUB Y N 20 
CZN C24 H24  SING N N 21 
CZN C25 C26  SING Y N 22 
CZN C25 O28  SING N N 23 
CZN C26 C27  DOUB Y N 24 
CZN C26 H26  SING N N 25 
CZN C27 H27  SING N N 26 
CZN O28 H28  SING N N 27 
CZN C29 C30  SING N N 28 
CZN C29 H291 SING N N 29 
CZN C29 H292 SING N N 30 
CZN C30 C31  DOUB Y N 31 
CZN C30 C35  SING Y N 32 
CZN C31 C32  SING Y N 33 
CZN C31 H31  SING N N 34 
CZN C32 C33  DOUB Y N 35 
CZN C32 H32  SING N N 36 
CZN C33 C34  SING Y N 37 
CZN C33 H33  SING N N 38 
CZN C34 C35  DOUB Y N 39 
CZN C34 H34  SING N N 40 
CZN C35 H35  SING N N 41 
CZN N1  C2   SING N N 42 
CZN C2  O36  SING N N 43 
CZN C2  C10  SING N N 44 
CZN O36 O37  SING N N 45 
CZN O37 H37  SING N N 46 
CZN C10 C11  SING N N 47 
CZN C10 H101 SING N N 48 
CZN C10 H102 SING N N 49 
CZN C11 C12  DOUB Y N 50 
CZN C11 C20  SING Y N 51 
CZN C12 C13  SING Y N 52 
CZN C12 H12  SING N N 53 
CZN C13 C14  DOUB Y N 54 
CZN C13 C18  SING Y N 55 
CZN C14 C15  SING Y N 56 
CZN C14 H14  SING N N 57 
CZN C18 C19  SING Y N 58 
CZN C18 C17  DOUB Y N 59 
CZN C19 C20  DOUB Y N 60 
CZN C19 H19  SING N N 61 
CZN C20 H20  SING N N 62 
CZN C17 C16  SING Y N 63 
CZN C17 H17  SING N N 64 
CZN C16 C15  DOUB Y N 65 
CZN C16 H16  SING N N 66 
CZN C15 H15  SING N N 67 
# 
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 
CZN SMILES           ACDLabs              10.04 O=C1N4C=C(NC(C4=NC1(OO)Cc3cc2ccccc2cc3)Cc5ccccc5)c6ccc(O)cc6                                                                                                                             
CZN InChI            InChI                1.02b InChI=1/C30H25N3O4/c34-25-14-12-23(13-15-25)27-19-33-28(26(31-27)17-20-6-2-1-3-7-20)32-30(37-36,29(33)35)18-21-10-11-22-8-4-5-9-24(22)16-21/h1-16,19,26,31,34,36H,17-18H2/t26-,30-/m0/s1 
CZN InChIKey         InChI                1.02b OMOBIXPIGAIKCC-YZNIXAGQBW                                                                                                                                                                
CZN SMILES_CANONICAL CACTVS               3.341 OO[C@]1(Cc2ccc3ccccc3c2)N=C4[C@H](Cc5ccccc5)NC(=CN4C1=O)c6ccc(O)cc6                                                                                                                      
CZN SMILES           CACTVS               3.341 OO[C]1(Cc2ccc3ccccc3c2)N=C4[CH](Cc5ccccc5)NC(=CN4C1=O)c6ccc(O)cc6                                                                                                                        
CZN SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 c1ccc(cc1)CC2C3=N[C@@](C(=O)N3C=C(N2)c4ccc(cc4)O)(Cc5ccc6ccccc6c5)OO                                                                                                                     
CZN SMILES           "OpenEye OEToolkits" 1.5.0 c1ccc(cc1)CC2C3=NC(C(=O)N3C=C(N2)c4ccc(cc4)O)(Cc5ccc6ccccc6c5)OO                                                                                                                         
# 
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 
CZN "SYSTEMATIC NAME" ACDLabs              10.04 (2S,8S)-8-benzyl-2-hydroperoxy-6-(4-hydroxyphenyl)-2-(naphthalen-2-ylmethyl)-7,8-dihydroimidazo[1,2-a]pyrazin-3(2H)-one  
CZN "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 (2S)-2-hydroperoxy-6-(4-hydroxyphenyl)-2-(naphthalen-2-ylmethyl)-8-(phenylmethyl)-7,8-dihydroimidazo[3,2-a]pyrazin-3-one 
# 
