data_2HL # _chem_comp.id 2HL _chem_comp.name "1-[(1-benzoylpiperidin-4-yl)methyl]-N-(pyridin-3-yl)-1H-benzimidazole-5-carboxamide" _chem_comp.type NON-POLYMER _chem_comp.pdbx_type HETAIN _chem_comp.formula "C26 H25 N5 O2" _chem_comp.mon_nstd_parent_comp_id ? _chem_comp.pdbx_synonyms ? _chem_comp.pdbx_formal_charge 0 _chem_comp.pdbx_initial_date 2013-10-22 _chem_comp.pdbx_modified_date 2014-02-14 _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 439.509 _chem_comp.one_letter_code ? _chem_comp.three_letter_code 2HL _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 4N9E _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 2HL C1 C1 C 0 1 Y N N 9.301 4.090 -5.825 8.658 -2.477 0.686 C1 2HL 1 2HL C2 C2 C 0 1 Y N N 10.070 3.191 -6.539 7.358 -2.932 0.554 C2 2HL 2 2HL C3 C3 C 0 1 Y N N 11.450 3.318 -6.543 6.405 -2.140 -0.054 C3 2HL 3 2HL C4 C4 C 0 1 Y N N 12.053 4.346 -5.808 6.755 -0.878 -0.537 C4 2HL 4 2HL C5 C5 C 0 1 Y N N 11.251 5.251 -5.089 8.069 -0.426 -0.401 C5 2HL 5 2HL C6 C6 C 0 1 Y N N 9.876 5.125 -5.094 9.012 -1.227 0.209 C6 2HL 6 2HL C7 C7 C 0 1 N N N 13.535 4.496 -5.799 5.740 -0.025 -1.189 C7 2HL 7 2HL O8 O8 O 0 1 N N N 14.108 4.890 -6.803 6.063 0.720 -2.093 O8 2HL 8 2HL N9 N9 N 0 1 N N N 14.265 4.197 -4.696 4.456 -0.074 -0.782 N9 2HL 9 2HL C10 C10 C 0 1 N N N 15.729 4.361 -4.715 4.072 -0.876 0.388 C10 2HL 10 2HL C11 C11 C 0 1 N N N 16.077 5.349 -3.590 3.307 0.019 1.369 C11 2HL 11 2HL C12 C12 C 0 1 N N N 15.647 4.735 -2.247 2.131 0.676 0.643 C12 2HL 12 2HL C13 C13 C 0 1 N N N 14.131 4.453 -2.207 2.657 1.550 -0.498 C13 2HL 13 2HL C14 C14 C 0 1 N N N 13.635 3.698 -3.452 3.415 0.678 -1.497 C14 2HL 14 2HL C15 C15 C 0 1 N N N 16.120 5.632 -1.082 1.345 1.544 1.628 C15 2HL 15 2HL N16 N16 N 0 1 Y N N 15.345 6.857 -0.807 0.153 2.077 0.966 N16 2HL 16 2HL C17 C17 C 0 1 Y N N 14.387 7.469 -1.565 0.043 3.291 0.359 C17 2HL 17 2HL N18 N18 N 0 1 Y N N 13.933 8.527 -0.958 -1.154 3.442 -0.126 N18 2HL 18 2HL C19 C19 C 0 1 Y N N 14.561 8.667 0.244 -1.895 2.334 0.137 C19 2HL 19 2HL C20 C20 C 0 1 Y N N 15.467 7.605 0.352 -1.063 1.441 0.837 C20 2HL 20 2HL C21 C21 C 0 1 Y N N 16.261 7.485 1.484 -1.550 0.203 1.240 C21 2HL 21 2HL C22 C22 C 0 1 Y N N 16.154 8.395 2.499 -2.836 -0.153 0.957 C22 2HL 22 2HL C23 C23 C 0 1 Y N N 15.281 9.485 2.384 -3.678 0.722 0.257 C23 2HL 23 2HL C24 C24 C 0 1 Y N N 14.449 9.600 1.274 -3.210 1.969 -0.147 C24 2HL 24 2HL C25 C25 C 0 1 N N N 15.081 10.400 3.519 -5.067 0.324 -0.044 C25 2HL 25 2HL O26 O26 O 0 1 N N N 14.547 11.487 3.410 -5.799 1.082 -0.650 O26 2HL 26 2HL N27 N27 N 0 1 N N N 15.407 9.834 4.706 -5.525 -0.880 0.354 N27 2HL 27 2HL C28 C28 C 0 1 Y N N 15.196 10.294 6.006 -6.804 -1.302 -0.024 C28 2HL 28 2HL C29 C29 C 0 1 Y N N 15.954 9.797 7.072 -7.389 -0.821 -1.193 C29 2HL 29 2HL C30 C30 C 0 1 Y N N 15.610 10.234 8.342 -8.657 -1.269 -1.526 C30 2HL 30 2HL C31 C31 C 0 1 Y N N 14.529 11.081 8.523 -9.295 -2.171 -0.694 C31 2HL 31 2HL N32 N32 N 0 1 Y N N 13.805 11.498 7.499 -8.713 -2.607 0.406 N32 2HL 32 2HL C33 C33 C 0 1 Y N N 14.093 11.115 6.273 -7.505 -2.211 0.757 C33 2HL 33 2HL H1 H1 H 0 1 N N N 8.226 3.987 -5.835 9.399 -3.099 1.166 H1 2HL 34 2HL H2 H2 H 0 1 N N N 9.597 2.393 -7.092 7.088 -3.908 0.928 H2 2HL 35 2HL H3 H3 H 0 1 N N N 12.057 2.628 -7.110 5.391 -2.497 -0.156 H3 2HL 36 2HL H4 H4 H 0 1 N N N 11.714 6.050 -4.529 8.346 0.550 -0.772 H4 2HL 37 2HL H5 H5 H 0 1 N N N 9.258 5.817 -4.541 10.027 -0.876 0.318 H5 2HL 38 2HL H6 H6 H 0 1 N N N 16.221 3.394 -4.536 3.433 -1.701 0.072 H6 2HL 39 2HL H7 H7 H 0 1 N N N 16.053 4.763 -5.686 4.966 -1.268 0.872 H7 2HL 40 2HL H8 H8 H 0 1 N N N 17.161 5.535 -3.582 2.934 -0.585 2.196 H8 2HL 41 2HL H9 H9 H 0 1 N N N 15.544 6.297 -3.752 3.975 0.790 1.753 H9 2HL 42 2HL H10 H10 H 0 1 N N N 16.163 3.769 -2.147 1.477 -0.096 0.238 H10 2HL 43 2HL H11 H11 H 0 1 N N N 13.596 5.412 -2.141 1.820 2.036 -0.999 H11 2HL 44 2HL H12 H12 H 0 1 N N N 13.909 3.847 -1.316 3.330 2.307 -0.096 H12 2HL 45 2HL H13 H13 H 0 1 N N N 12.545 3.824 -3.532 3.876 1.310 -2.255 H13 2HL 46 2HL H14 H14 H 0 1 N N N 13.874 2.630 -3.337 2.721 -0.018 -1.969 H14 2HL 47 2HL H15 H15 H 0 1 N N N 16.104 5.020 -0.168 1.045 0.940 2.485 H15 2HL 48 2HL H16 H16 H 0 1 N N N 17.154 5.938 -1.301 1.972 2.368 1.967 H16 2HL 49 2HL H17 H17 H 0 1 N N N 14.053 7.123 -2.532 0.835 4.022 0.290 H17 2HL 50 2HL H18 H18 H 0 1 N N N 16.966 6.670 1.563 -0.909 -0.479 1.779 H18 2HL 51 2HL H19 H19 H 0 1 N N N 16.746 8.273 3.394 -3.208 -1.117 1.273 H19 2HL 52 2HL H20 H20 H 0 1 N N N 13.727 10.401 1.211 -3.858 2.644 -0.687 H20 2HL 53 2HL H21 H21 H 0 1 N N N 15.870 8.950 4.640 -4.967 -1.453 0.903 H21 2HL 54 2HL H22 H22 H 0 1 N N N 16.768 9.106 6.913 -6.868 -0.117 -1.824 H22 2HL 55 2HL H23 H23 H 0 1 N N N 16.188 9.912 9.195 -9.142 -0.918 -2.424 H23 2HL 56 2HL H24 H24 H 0 1 N N N 14.273 11.407 9.520 -10.283 -2.524 -0.949 H24 2HL 57 2HL H25 H25 H 0 1 N N N 13.466 11.440 5.456 -7.059 -2.593 1.663 H25 2HL 58 # 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 2HL O8 C7 DOUB N N 1 2HL C3 C2 DOUB Y N 2 2HL C3 C4 SING Y N 3 2HL C2 C1 SING Y N 4 2HL C1 C6 DOUB Y N 5 2HL C4 C7 SING N N 6 2HL C4 C5 DOUB Y N 7 2HL C7 N9 SING N N 8 2HL C6 C5 SING Y N 9 2HL C10 N9 SING N N 10 2HL C10 C11 SING N N 11 2HL N9 C14 SING N N 12 2HL C11 C12 SING N N 13 2HL C14 C13 SING N N 14 2HL C12 C13 SING N N 15 2HL C12 C15 SING N N 16 2HL C17 N18 DOUB Y N 17 2HL C17 N16 SING Y N 18 2HL C15 N16 SING N N 19 2HL N18 C19 SING Y N 20 2HL N16 C20 SING Y N 21 2HL C19 C20 DOUB Y N 22 2HL C19 C24 SING Y N 23 2HL C20 C21 SING Y N 24 2HL C24 C23 DOUB Y N 25 2HL C21 C22 DOUB Y N 26 2HL C23 C22 SING Y N 27 2HL C23 C25 SING N N 28 2HL O26 C25 DOUB N N 29 2HL C25 N27 SING N N 30 2HL N27 C28 SING N N 31 2HL C28 C33 DOUB Y N 32 2HL C28 C29 SING Y N 33 2HL C33 N32 SING Y N 34 2HL C29 C30 DOUB Y N 35 2HL N32 C31 DOUB Y N 36 2HL C30 C31 SING Y N 37 2HL C1 H1 SING N N 38 2HL C2 H2 SING N N 39 2HL C3 H3 SING N N 40 2HL C5 H4 SING N N 41 2HL C6 H5 SING N N 42 2HL C10 H6 SING N N 43 2HL C10 H7 SING N N 44 2HL C11 H8 SING N N 45 2HL C11 H9 SING N N 46 2HL C12 H10 SING N N 47 2HL C13 H11 SING N N 48 2HL C13 H12 SING N N 49 2HL C14 H13 SING N N 50 2HL C14 H14 SING N N 51 2HL C15 H15 SING N N 52 2HL C15 H16 SING N N 53 2HL C17 H17 SING N N 54 2HL C21 H18 SING N N 55 2HL C22 H19 SING N N 56 2HL C24 H20 SING N N 57 2HL N27 H21 SING N N 58 2HL C29 H22 SING N N 59 2HL C30 H23 SING N N 60 2HL C31 H24 SING N N 61 2HL C33 H25 SING N N 62 # 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 2HL SMILES ACDLabs 12.01 "O=C(c1ccccc1)N5CCC(Cn3c4ccc(C(=O)Nc2cccnc2)cc4nc3)CC5" 2HL InChI InChI 1.03 "InChI=1S/C26H25N5O2/c32-25(29-22-7-4-12-27-16-22)21-8-9-24-23(15-21)28-18-31(24)17-19-10-13-30(14-11-19)26(33)20-5-2-1-3-6-20/h1-9,12,15-16,18-19H,10-11,13-14,17H2,(H,29,32)" 2HL InChIKey InChI 1.03 UROBXDPDOFZURE-UHFFFAOYSA-N 2HL SMILES_CANONICAL CACTVS 3.385 "O=C(Nc1cccnc1)c2ccc3n(CC4CCN(CC4)C(=O)c5ccccc5)cnc3c2" 2HL SMILES CACTVS 3.385 "O=C(Nc1cccnc1)c2ccc3n(CC4CCN(CC4)C(=O)c5ccccc5)cnc3c2" 2HL SMILES_CANONICAL "OpenEye OEToolkits" 1.7.6 "c1ccc(cc1)C(=O)N2CCC(CC2)Cn3cnc4c3ccc(c4)C(=O)Nc5cccnc5" 2HL SMILES "OpenEye OEToolkits" 1.7.6 "c1ccc(cc1)C(=O)N2CCC(CC2)Cn3cnc4c3ccc(c4)C(=O)Nc5cccnc5" # 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 2HL "SYSTEMATIC NAME" ACDLabs 12.01 "1-[(1-benzoylpiperidin-4-yl)methyl]-N-(pyridin-3-yl)-1H-benzimidazole-5-carboxamide" 2HL "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.7.6 "1-[[1-(phenylcarbonyl)piperidin-4-yl]methyl]-N-pyridin-3-yl-benzimidazole-5-carboxamide" # loop_ _pdbx_chem_comp_audit.comp_id _pdbx_chem_comp_audit.action_type _pdbx_chem_comp_audit.date _pdbx_chem_comp_audit.processing_site 2HL "Create component" 2013-10-22 RCSB 2HL "Initial release" 2014-02-19 RCSB #