data_2OL # _chem_comp.id 2OL _chem_comp.name "1-({1-(2-aminopyrimidin-4-yl)-2-[(2-methoxyethyl)amino]-1H-benzimidazol-6-yl}ethynyl)cyclohexanol" _chem_comp.type NON-POLYMER _chem_comp.pdbx_type HETAIN _chem_comp.formula "C22 H26 N6 O2" _chem_comp.mon_nstd_parent_comp_id ? _chem_comp.pdbx_synonyms ? _chem_comp.pdbx_formal_charge 0 _chem_comp.pdbx_initial_date 2013-12-17 _chem_comp.pdbx_modified_date 2014-02-07 _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 406.481 _chem_comp.one_letter_code ? _chem_comp.three_letter_code 2OL _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 4O0T _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 2OL C1 C1 C 0 1 N N N 13.355 -11.834 15.513 7.955 -0.229 0.358 C1 2OL 1 2OL O2 O2 O 0 1 N N N 13.008 -12.591 14.352 6.639 -0.779 0.442 O2 2OL 2 2OL C3 C3 C 0 1 N N N 12.407 -13.860 14.626 6.265 -1.568 -0.688 C3 2OL 3 2OL C4 C4 C 0 1 N N N 12.624 -14.775 13.416 4.845 -2.102 -0.491 C4 2OL 4 2OL N5 N5 N 0 1 N N N 13.813 -15.612 13.615 3.901 -0.983 -0.471 N5 2OL 5 2OL C6 C6 C 0 1 Y N N 15.016 -15.351 12.992 2.553 -1.221 -0.303 C6 2OL 6 2OL N7 N7 N 0 1 Y N N 15.204 -14.545 11.974 2.000 -2.406 -0.243 N7 2OL 7 2OL C8 C8 C 0 1 Y N N 16.520 -14.533 11.624 0.659 -2.279 -0.068 C8 2OL 8 2OL C9 C9 C 0 1 Y N N 17.246 -13.859 10.626 -0.382 -3.205 0.057 C9 2OL 9 2OL C10 C10 C 0 1 Y N N 18.595 -14.040 10.508 -1.664 -2.773 0.228 C10 2OL 10 2OL C11 C11 C 0 1 Y N N 19.258 -14.914 11.373 -1.952 -1.404 0.278 C11 2OL 11 2OL C12 C12 C 0 1 Y N N 18.553 -15.584 12.369 -0.926 -0.469 0.155 C12 2OL 12 2OL C13 C13 C 0 1 Y N N 17.185 -15.409 12.508 0.376 -0.903 -0.018 C13 2OL 13 2OL N14 N14 N 0 1 Y N N 16.207 -15.921 13.368 1.594 -0.253 -0.169 N14 2OL 14 2OL C15 C15 C 0 1 Y N N 16.347 -16.826 14.433 1.801 1.125 -0.176 C15 2OL 15 2OL C16 C16 C 0 1 Y N N 17.415 -17.720 14.562 0.995 1.957 -0.952 C16 2OL 16 2OL C17 C17 C 0 1 Y N N 17.462 -18.574 15.653 1.237 3.318 -0.929 C17 2OL 17 2OL N18 N18 N 0 1 Y N N 16.491 -18.531 16.552 2.220 3.788 -0.176 N18 2OL 18 2OL C19 C19 C 0 1 Y N N 15.489 -17.676 16.411 2.970 2.973 0.551 C19 2OL 19 2OL N20 N20 N 0 1 Y N N 15.419 -16.845 15.379 2.766 1.664 0.560 N20 2OL 20 2OL N21 N21 N 0 1 N N N 14.487 -17.648 17.364 3.988 3.502 1.325 N21 2OL 21 2OL C22 C22 C 0 1 N N N 20.673 -15.114 11.283 -3.303 -0.964 0.457 C22 2OL 22 2OL C23 C23 C 0 1 N N N 21.817 -15.351 11.255 -4.411 -0.603 0.603 C23 2OL 23 2OL C24 C24 C 0 1 N N N 23.264 -15.624 11.219 -5.799 -0.150 0.786 C24 2OL 24 2OL C25 C25 C 0 1 N N N 23.765 -15.806 12.649 -5.838 1.380 0.806 C25 2OL 25 2OL C26 C26 C 0 1 N N N 25.226 -16.255 12.660 -5.296 1.921 -0.518 C26 2OL 26 2OL C27 C27 C 0 1 N N N 25.374 -17.567 11.895 -6.157 1.404 -1.672 C27 2OL 27 2OL C28 C28 C 0 1 N N N 24.925 -17.360 10.450 -6.118 -0.125 -1.692 C28 2OL 28 2OL C29 C29 C 0 1 N N N 23.464 -16.917 10.421 -6.661 -0.667 -0.368 C29 2OL 29 2OL O30 O30 O 0 1 N N N 23.966 -14.554 10.589 -6.306 -0.656 2.023 O30 2OL 30 2OL H1 H1 H 0 1 N N N 13.808 -10.879 15.207 8.025 0.413 -0.519 H1 2OL 31 2OL H2 H2 H 0 1 N N N 12.450 -11.637 16.106 8.163 0.356 1.254 H2 2OL 32 2OL H3 H3 H 0 1 N N N 14.074 -12.403 16.120 8.682 -1.038 0.276 H3 2OL 33 2OL H4 H4 H 0 1 N N N 11.329 -13.729 14.803 6.300 -0.954 -1.588 H4 2OL 34 2OL H5 H5 H 0 1 N N N 12.873 -14.306 15.517 6.957 -2.404 -0.793 H5 2OL 35 2OL H6 H6 H 0 1 N N N 12.761 -14.159 12.515 4.593 -2.776 -1.310 H6 2OL 36 2OL H7 H7 H 0 1 N N N 11.743 -15.421 13.287 4.788 -2.643 0.454 H7 2OL 37 2OL H8 H8 H 0 1 N N N 13.551 -16.536 13.338 4.223 -0.074 -0.575 H8 2OL 38 2OL H9 H9 H 0 1 N N N 16.733 -13.193 9.948 -0.170 -4.263 0.019 H9 2OL 39 2OL H10 H10 H 0 1 N N N 19.148 -13.508 9.748 -2.464 -3.493 0.324 H10 2OL 40 2OL H11 H11 H 0 1 N N N 19.078 -16.247 13.041 -1.146 0.587 0.193 H11 2OL 41 2OL H12 H12 H 0 1 N N N 18.197 -17.745 13.817 0.200 1.548 -1.558 H12 2OL 42 2OL H13 H13 H 0 1 N N N 18.282 -19.267 15.768 0.632 3.991 -1.518 H13 2OL 43 2OL H14 H14 H 0 1 N N N 13.810 -16.956 17.116 4.146 4.460 1.330 H14 2OL 44 2OL H15 H15 H 0 1 N N N 14.046 -18.544 17.410 4.545 2.917 1.861 H15 2OL 45 2OL H16 H16 H 0 1 N N N 23.678 -14.850 13.186 -6.867 1.715 0.942 H16 2OL 46 2OL H17 H17 H 0 1 N N N 23.150 -16.567 13.152 -5.225 1.748 1.628 H17 2OL 47 2OL H18 H18 H 0 1 N N N 25.555 -16.400 13.700 -5.324 3.011 -0.503 H18 2OL 48 2OL H19 H19 H 0 1 N N N 25.848 -15.483 12.183 -4.268 1.586 -0.654 H19 2OL 49 2OL H20 H20 H 0 1 N N N 24.750 -18.340 12.367 -7.186 1.739 -1.536 H20 2OL 50 2OL H21 H21 H 0 1 N N N 26.427 -17.885 11.911 -5.771 1.790 -2.615 H21 2OL 51 2OL H22 H22 H 0 1 N N N 25.031 -18.304 9.896 -6.732 -0.494 -2.514 H22 2OL 52 2OL H23 H23 H 0 1 N N N 25.551 -16.587 9.980 -5.090 -0.461 -1.827 H23 2OL 53 2OL H24 H24 H 0 1 N N N 23.161 -16.746 9.377 -6.633 -1.757 -0.382 H24 2OL 54 2OL H25 H25 H 0 1 N N N 22.839 -17.710 10.859 -7.689 -0.332 -0.232 H25 2OL 55 2OL H26 H26 H 0 1 N N N 23.839 -13.755 11.087 -6.310 -1.621 2.081 H26 2OL 56 # 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 2OL C29 C28 SING N N 1 2OL C29 C24 SING N N 2 2OL C28 C27 SING N N 3 2OL C10 C9 DOUB Y N 4 2OL C10 C11 SING Y N 5 2OL O30 C24 SING N N 6 2OL C9 C8 SING Y N 7 2OL C24 C23 SING N N 8 2OL C24 C25 SING N N 9 2OL C23 C22 TRIP N N 10 2OL C22 C11 SING N N 11 2OL C11 C12 DOUB Y N 12 2OL C8 N7 SING Y N 13 2OL C8 C13 DOUB Y N 14 2OL C27 C26 SING N N 15 2OL N7 C6 DOUB Y N 16 2OL C12 C13 SING Y N 17 2OL C13 N14 SING Y N 18 2OL C25 C26 SING N N 19 2OL C6 N14 SING Y N 20 2OL C6 N5 SING N N 21 2OL N14 C15 SING N N 22 2OL C4 N5 SING N N 23 2OL C4 C3 SING N N 24 2OL O2 C3 SING N N 25 2OL O2 C1 SING N N 26 2OL C15 C16 DOUB Y N 27 2OL C15 N20 SING Y N 28 2OL C16 C17 SING Y N 29 2OL N20 C19 DOUB Y N 30 2OL C17 N18 DOUB Y N 31 2OL C19 N18 SING Y N 32 2OL C19 N21 SING N N 33 2OL C1 H1 SING N N 34 2OL C1 H2 SING N N 35 2OL C1 H3 SING N N 36 2OL C3 H4 SING N N 37 2OL C3 H5 SING N N 38 2OL C4 H6 SING N N 39 2OL C4 H7 SING N N 40 2OL N5 H8 SING N N 41 2OL C9 H9 SING N N 42 2OL C10 H10 SING N N 43 2OL C12 H11 SING N N 44 2OL C16 H12 SING N N 45 2OL C17 H13 SING N N 46 2OL N21 H14 SING N N 47 2OL N21 H15 SING N N 48 2OL C25 H16 SING N N 49 2OL C25 H17 SING N N 50 2OL C26 H18 SING N N 51 2OL C26 H19 SING N N 52 2OL C27 H20 SING N N 53 2OL C27 H21 SING N N 54 2OL C28 H22 SING N N 55 2OL C28 H23 SING N N 56 2OL C29 H24 SING N N 57 2OL C29 H25 SING N N 58 2OL O30 H26 SING N N 59 # 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 2OL SMILES ACDLabs 12.01 "OC4(C#Cc1ccc2nc(NCCOC)n(c2c1)c3nc(ncc3)N)CCCCC4" 2OL InChI InChI 1.03 "InChI=1S/C22H26N6O2/c1-30-14-13-25-21-26-17-6-5-16(7-11-22(29)9-3-2-4-10-22)15-18(17)28(21)19-8-12-24-20(23)27-19/h5-6,8,12,15,29H,2-4,9-10,13-14H2,1H3,(H,25,26)(H2,23,24,27)" 2OL InChIKey InChI 1.03 RZXMIHOUHYSGJO-UHFFFAOYSA-N 2OL SMILES_CANONICAL CACTVS 3.385 "COCCNc1nc2ccc(cc2n1c3ccnc(N)n3)C#CC4(O)CCCCC4" 2OL SMILES CACTVS 3.385 "COCCNc1nc2ccc(cc2n1c3ccnc(N)n3)C#CC4(O)CCCCC4" 2OL SMILES_CANONICAL "OpenEye OEToolkits" 1.7.6 "COCCNc1nc2ccc(cc2n1c3ccnc(n3)N)C#CC4(CCCCC4)O" 2OL SMILES "OpenEye OEToolkits" 1.7.6 "COCCNc1nc2ccc(cc2n1c3ccnc(n3)N)C#CC4(CCCCC4)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 2OL "SYSTEMATIC NAME" ACDLabs 12.01 "1-({1-(2-aminopyrimidin-4-yl)-2-[(2-methoxyethyl)amino]-1H-benzimidazol-6-yl}ethynyl)cyclohexanol" 2OL "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.7.6 "1-[2-[3-(2-azanylpyrimidin-4-yl)-2-(2-methoxyethylamino)benzimidazol-5-yl]ethynyl]cyclohexan-1-ol" # loop_ _pdbx_chem_comp_audit.comp_id _pdbx_chem_comp_audit.action_type _pdbx_chem_comp_audit.date _pdbx_chem_comp_audit.processing_site 2OL "Create component" 2013-12-17 RCSB 2OL "Initial release" 2014-02-12 RCSB #