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 ? ##