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 2021-03-01 _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 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" CZN InChI InChI 1.03 "InChI=1S/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 1.03 OMOBIXPIGAIKCC-YZNIXAGQSA-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 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" # # loop_ _pdbx_chem_comp_audit.comp_id _pdbx_chem_comp_audit.action_type _pdbx_chem_comp_audit.date _pdbx_chem_comp_audit.processing_site CZN "Create component" 2003-07-07 RCSB CZN "Modify descriptor" 2011-06-04 RCSB CZN "Modify synonyms" 2021-03-01 PDBE # _pdbx_chem_comp_synonyms.ordinal 1 _pdbx_chem_comp_synonyms.comp_id CZN _pdbx_chem_comp_synonyms.name N-COELENETERAZINE _pdbx_chem_comp_synonyms.provenance ? _pdbx_chem_comp_synonyms.type ? ##