data_O23 # _chem_comp.id O23 _chem_comp.name "N-cyclopropyl-4-{8-[(thiophen-2-ylmethyl)amino]imidazo[1,2-a]pyrazin-3-yl}benzamide" _chem_comp.type NON-POLYMER _chem_comp.pdbx_type HETAIN _chem_comp.formula "C21 H19 N5 O S" _chem_comp.mon_nstd_parent_comp_id ? _chem_comp.pdbx_synonyms ? _chem_comp.pdbx_formal_charge 0 _chem_comp.pdbx_initial_date 2014-10-02 _chem_comp.pdbx_modified_date 2015-02-06 _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 389.473 _chem_comp.one_letter_code ? _chem_comp.three_letter_code O23 _chem_comp.pdbx_model_coordinates_details ? _chem_comp.pdbx_model_coordinates_missing_flag N _chem_comp.pdbx_ideal_coordinates_details Corina _chem_comp.pdbx_ideal_coordinates_missing_flag N _chem_comp.pdbx_model_coordinates_db_code 3WZK _chem_comp.pdbx_subcomponent_list ? _chem_comp.pdbx_processing_site PDBJ # 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 O23 O O O 0 1 N N N 5.313 -34.404 -16.548 -6.769 -1.751 0.338 O O23 1 O23 C C C 0 1 N N N 4.252 -33.788 -16.498 -6.154 -0.731 0.092 C O23 2 O23 N N N 0 1 N N N 3.790 -33.134 -17.571 -6.819 0.421 -0.125 N O23 3 O23 C1 C1 C 0 1 N N N 4.620 -33.047 -18.765 -8.283 0.445 -0.063 C1 O23 4 O23 C3 C3 C 0 1 N N N 4.278 -31.832 -19.625 -8.940 1.613 0.675 C3 O23 5 O23 C2 C2 C 0 1 N N N 5.478 -31.793 -18.680 -9.005 1.539 -0.852 C2 O23 6 O23 C4 C4 C 0 1 Y N N 3.476 -33.777 -15.205 -4.680 -0.753 0.036 C4 O23 7 O23 C9 C9 C 0 1 Y N N 2.679 -32.680 -14.873 -3.990 -1.948 0.266 C9 O23 8 O23 C8 C8 C 0 1 Y N N 1.962 -32.674 -13.669 -2.626 -1.969 0.214 C8 O23 9 O23 C7 C7 C 0 1 Y N N 2.029 -33.758 -12.792 -1.918 -0.795 -0.069 C7 O23 10 O23 C6 C6 C 0 1 Y N N 2.844 -34.843 -13.122 -2.609 0.399 -0.299 C6 O23 11 O23 C5 C5 C 0 1 Y N N 3.557 -34.861 -14.327 -3.973 0.419 -0.253 C5 O23 12 O23 C10 C10 C 0 1 Y N N 1.243 -33.692 -11.512 -0.445 -0.818 -0.124 C10 O23 13 O23 N2 N2 N 0 1 Y N N 0.705 -34.813 -10.979 0.396 0.252 0.026 N2 O23 14 O23 C13 C13 C 0 1 Y N N 0.690 -36.128 -11.317 0.194 1.586 0.257 C13 O23 15 O23 C14 C14 C 0 1 Y N N 0.026 -37.087 -10.524 1.250 2.419 0.360 C14 O23 16 O23 N3 N3 N 0 1 Y N N -0.626 -36.736 -9.388 2.502 1.969 0.241 N3 O23 17 O23 C15 C15 C 0 1 Y N N -0.637 -35.436 -9.007 2.753 0.695 0.018 C15 O23 18 O23 C12 C12 C 0 1 Y N N 0.064 -34.421 -9.856 1.676 -0.220 -0.098 C12 O23 19 O23 N1 N1 N 0 1 Y N N 0.185 -33.079 -9.704 1.623 -1.526 -0.315 N1 O23 20 O23 C11 C11 C 0 1 Y N N 0.923 -32.593 -10.731 0.356 -1.923 -0.332 C11 O23 21 O23 N4 N4 N 0 1 N N N -1.274 -35.014 -7.894 4.061 0.252 -0.103 N4 O23 22 O23 C16 C16 C 0 1 N N N -1.905 -35.934 -6.969 5.170 1.201 0.017 C16 O23 23 O23 C17 C17 C 0 1 Y N N -0.914 -36.426 -5.937 6.477 0.471 -0.152 C17 O23 24 O23 S S S 0 1 Y N N -0.275 -35.242 -4.835 7.403 -0.265 1.150 S O23 25 O23 C20 C20 C 0 1 Y N N 0.715 -36.382 -3.976 8.632 -0.802 0.013 C20 O23 26 O23 C19 C19 C 0 1 Y N N 0.519 -37.631 -4.577 8.298 -0.420 -1.221 C19 O23 27 O23 C18 C18 C 0 1 Y N N -0.372 -37.676 -5.657 7.106 0.279 -1.312 C18 O23 28 O23 H1 H1 H 0 1 N N N 2.885 -32.710 -17.553 -6.329 1.235 -0.321 H1 O23 29 O23 H2 H2 H 0 1 N N N 5.025 -33.952 -19.242 -8.766 -0.530 0.004 H2 O23 30 O23 H3 H3 H 0 1 N N N 4.435 -31.866 -20.713 -9.856 1.407 1.229 H3 O23 31 O23 H4 H4 H 0 1 N N N 3.382 -31.234 -19.402 -8.283 2.364 1.115 H4 O23 32 O23 H5 H5 H 0 1 N N N 6.499 -31.797 -19.088 -8.392 2.241 -1.416 H5 O23 33 O23 H6 H6 H 0 1 N N N 5.446 -31.166 -17.777 -9.964 1.285 -1.303 H6 O23 34 O23 H7 H7 H 0 1 N N N 2.615 -31.836 -15.544 -4.536 -2.853 0.485 H7 O23 35 O23 H8 H8 H 0 1 N N N 1.350 -31.821 -13.417 -2.093 -2.891 0.393 H8 O23 36 O23 H9 H9 H 0 1 N N N 2.925 -35.677 -12.441 -2.063 1.305 -0.518 H9 O23 37 O23 H10 H10 H 0 1 N N N 4.170 -35.714 -14.578 -4.507 1.340 -0.435 H10 O23 38 O23 H11 H11 H 0 1 N N N 1.199 -36.447 -12.215 -0.810 1.971 0.356 H11 O23 39 O23 H12 H12 H 0 1 N N N 0.037 -38.123 -10.828 1.080 3.470 0.542 H12 O23 40 O23 H13 H13 H 0 1 N N N 1.203 -31.565 -10.905 0.012 -2.936 -0.483 H13 O23 41 O23 H14 H14 H 0 1 N N N -0.598 -34.504 -7.362 4.242 -0.687 -0.267 H14 O23 42 O23 H15 H15 H 0 1 N N N -2.732 -35.420 -6.458 5.078 1.966 -0.754 H15 O23 43 O23 H16 H16 H 0 1 N N N -2.299 -36.795 -7.529 5.141 1.671 1.000 H16 O23 44 O23 H17 H17 H 0 1 N N N 1.360 -36.168 -3.137 9.521 -1.357 0.273 H17 O23 45 O23 H18 H18 H 0 1 N N N 1.029 -38.516 -4.226 8.909 -0.641 -2.083 H18 O23 46 O23 H19 H19 H 0 1 N N N -0.610 -38.575 -6.207 6.716 0.643 -2.251 H19 O23 47 # 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 O23 C3 C1 SING N N 1 O23 C3 C2 SING N N 2 O23 C1 C2 SING N N 3 O23 C1 N SING N N 4 O23 N C SING N N 5 O23 O C DOUB N N 6 O23 C C4 SING N N 7 O23 C4 C9 DOUB Y N 8 O23 C4 C5 SING Y N 9 O23 C9 C8 SING Y N 10 O23 C5 C6 DOUB Y N 11 O23 C8 C7 DOUB Y N 12 O23 C6 C7 SING Y N 13 O23 C7 C10 SING N N 14 O23 C10 N2 SING Y N 15 O23 C10 C11 DOUB Y N 16 O23 C13 N2 SING Y N 17 O23 C13 C14 DOUB Y N 18 O23 N2 C12 SING Y N 19 O23 C11 N1 SING Y N 20 O23 C14 N3 SING Y N 21 O23 C12 N1 DOUB Y N 22 O23 C12 C15 SING Y N 23 O23 N3 C15 DOUB Y N 24 O23 C15 N4 SING N N 25 O23 N4 C16 SING N N 26 O23 C16 C17 SING N N 27 O23 C17 C18 DOUB Y N 28 O23 C17 S SING Y N 29 O23 C18 C19 SING Y N 30 O23 S C20 SING Y N 31 O23 C19 C20 DOUB Y N 32 O23 N H1 SING N N 33 O23 C1 H2 SING N N 34 O23 C3 H3 SING N N 35 O23 C3 H4 SING N N 36 O23 C2 H5 SING N N 37 O23 C2 H6 SING N N 38 O23 C9 H7 SING N N 39 O23 C8 H8 SING N N 40 O23 C6 H9 SING N N 41 O23 C5 H10 SING N N 42 O23 C13 H11 SING N N 43 O23 C14 H12 SING N N 44 O23 C11 H13 SING N N 45 O23 N4 H14 SING N N 46 O23 C16 H15 SING N N 47 O23 C16 H16 SING N N 48 O23 C20 H17 SING N N 49 O23 C19 H18 SING N N 50 O23 C18 H19 SING N N 51 # 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 O23 SMILES ACDLabs 12.01 "O=C(NC1CC1)c2ccc(cc2)c3cnc4c(nccn34)NCc5sccc5" O23 InChI InChI 1.03 "InChI=1S/C21H19N5OS/c27-21(25-16-7-8-16)15-5-3-14(4-6-15)18-13-24-20-19(22-9-10-26(18)20)23-12-17-2-1-11-28-17/h1-6,9-11,13,16H,7-8,12H2,(H,22,23)(H,25,27)" O23 InChIKey InChI 1.03 YUHKXKGPLTYXSO-UHFFFAOYSA-N O23 SMILES_CANONICAL CACTVS 3.385 "O=C(NC1CC1)c2ccc(cc2)c3cnc4n3ccnc4NCc5sccc5" O23 SMILES CACTVS 3.385 "O=C(NC1CC1)c2ccc(cc2)c3cnc4n3ccnc4NCc5sccc5" O23 SMILES_CANONICAL "OpenEye OEToolkits" 1.7.6 "c1cc(sc1)CNc2c3ncc(n3ccn2)c4ccc(cc4)C(=O)NC5CC5" O23 SMILES "OpenEye OEToolkits" 1.7.6 "c1cc(sc1)CNc2c3ncc(n3ccn2)c4ccc(cc4)C(=O)NC5CC5" # 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 O23 "SYSTEMATIC NAME" ACDLabs 12.01 "N-cyclopropyl-4-{8-[(thiophen-2-ylmethyl)amino]imidazo[1,2-a]pyrazin-3-yl}benzamide" O23 "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.7.6 "N-cyclopropyl-4-[8-(thiophen-2-ylmethylamino)imidazo[1,2-a]pyrazin-3-yl]benzamide" # loop_ _pdbx_chem_comp_audit.comp_id _pdbx_chem_comp_audit.action_type _pdbx_chem_comp_audit.date _pdbx_chem_comp_audit.processing_site O23 "Create component" 2014-10-02 PDBJ O23 "Initial release" 2015-02-11 RCSB #