data_014 # _chem_comp.id 014 _chem_comp.name "1-(5-chloro-6-fluoro-1H-benzimidazol-2-yl)-1H-pyrazole-4-carboxylic acid" _chem_comp.type NON-POLYMER _chem_comp.pdbx_type HETAIN _chem_comp.formula "C11 H6 Cl F N4 O2" _chem_comp.mon_nstd_parent_comp_id ? _chem_comp.pdbx_synonyms ? _chem_comp.pdbx_formal_charge 0 _chem_comp.pdbx_initial_date 2010-09-15 _chem_comp.pdbx_modified_date 2011-06-04 _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 280.642 _chem_comp.one_letter_code ? _chem_comp.three_letter_code 014 _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 3OUH _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 014 F F F 0 1 N N N 44.785 23.752 3.583 -5.106 1.369 0.007 F 014 1 014 CL CL CL 0 0 N N N 45.830 21.891 1.901 -5.198 -1.572 0.003 CL 014 2 014 C1 C1 C 0 1 N N N 36.581 17.490 4.338 5.412 -0.806 0.004 C1 014 3 014 N1 N1 N 0 1 Y N N 38.649 20.201 5.774 2.782 1.688 -0.001 N1 014 4 014 O1 O1 O 0 1 N N N 35.449 17.485 4.948 6.600 -0.171 0.008 O1 014 5 014 C2 C2 C 0 1 Y N N 37.633 18.457 4.743 4.161 -0.028 0.002 C2 014 6 014 N2 N2 N 0 1 Y N N 39.471 19.523 4.895 2.030 0.508 -0.003 N2 014 7 014 O2 O2 O 0 1 N N N 36.833 16.778 3.316 5.372 -2.020 -0.001 O2 014 8 014 C3 C3 C 0 1 Y N N 37.505 19.469 5.701 4.050 1.383 0.002 C3 014 9 014 N3 N3 N 0 1 Y N N 40.856 21.281 4.940 -0.205 1.500 -0.007 N3 014 10 014 C4 C4 C 0 1 Y N N 38.892 18.563 4.206 2.878 -0.538 -0.001 C4 014 11 014 N4 N4 N 0 1 Y N N 41.423 19.505 3.637 -0.047 -0.682 -0.007 N4 014 12 014 C5 C5 C 0 1 Y N N 40.621 20.015 4.581 0.642 0.429 -0.005 C5 014 13 014 C6 C6 C 0 1 Y N N 42.020 21.529 4.291 -1.496 1.003 -0.004 C6 014 14 014 C7 C7 C 0 1 Y N N 42.832 22.636 4.322 -2.753 1.591 0.001 C7 014 15 014 C8 C8 C 0 1 Y N N 43.965 22.679 3.577 -3.882 0.797 0.003 C8 014 16 014 C10 C10 C 0 1 Y N N 44.305 21.627 2.804 -3.767 -0.589 0.000 C10 014 17 014 C11 C11 C 0 1 Y N N 43.526 20.479 2.741 -2.527 -1.187 -0.004 C11 014 18 014 C12 C12 C 0 1 Y N N 42.369 20.437 3.486 -1.375 -0.396 -0.006 C12 014 19 014 HO1 HO1 H 0 1 N N N 34.859 16.879 4.516 7.393 -0.724 0.009 HO1 014 20 014 H3 H3 H 0 1 N N N 36.622 19.644 6.298 4.871 2.083 0.003 H3 014 21 014 H4 H4 H 0 1 N N N 39.314 17.986 3.397 2.606 -1.583 -0.002 H4 014 22 014 H7 H7 H 0 1 N N N 42.567 23.478 4.944 -2.848 2.667 0.003 H7 014 23 014 H11 H11 H 0 1 N N N 43.820 19.642 2.125 -2.445 -2.264 -0.006 H11 014 24 014 HN3 HN3 H 0 1 N N N 40.318 21.883 5.529 0.052 2.436 -0.006 HN3 014 25 # 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 014 C8 F SING N N 1 014 CL C10 SING N N 2 014 O2 C1 DOUB N N 3 014 C1 C2 SING N N 4 014 C1 O1 SING N N 5 014 N2 N1 SING Y N 6 014 C3 N1 DOUB Y N 7 014 O1 HO1 SING N N 8 014 C4 C2 DOUB Y N 9 014 C2 C3 SING Y N 10 014 C4 N2 SING Y N 11 014 C5 N2 SING Y N 12 014 C3 H3 SING N N 13 014 C6 N3 SING Y N 14 014 C5 N3 SING Y N 15 014 C4 H4 SING N N 16 014 C12 N4 SING Y N 17 014 N4 C5 DOUB Y N 18 014 C12 C6 DOUB Y N 19 014 C6 C7 SING Y N 20 014 C8 C7 DOUB Y N 21 014 C7 H7 SING N N 22 014 C10 C8 SING Y N 23 014 C11 C10 DOUB Y N 24 014 C11 C12 SING Y N 25 014 C11 H11 SING N N 26 014 N3 HN3 SING N N 27 # 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 014 SMILES ACDLabs 12.01 "O=C(O)c1cn(nc1)c2nc3c(n2)cc(F)c(Cl)c3" 014 SMILES_CANONICAL CACTVS 3.370 "OC(=O)c1cnn(c1)c2[nH]c3cc(F)c(Cl)cc3n2" 014 SMILES CACTVS 3.370 "OC(=O)c1cnn(c1)c2[nH]c3cc(F)c(Cl)cc3n2" 014 SMILES_CANONICAL "OpenEye OEToolkits" 1.7.0 "c1c2c(cc(c1F)Cl)nc([nH]2)n3cc(cn3)C(=O)O" 014 SMILES "OpenEye OEToolkits" 1.7.0 "c1c2c(cc(c1F)Cl)nc([nH]2)n3cc(cn3)C(=O)O" 014 InChI InChI 1.03 "InChI=1S/C11H6ClFN4O2/c12-6-1-8-9(2-7(6)13)16-11(15-8)17-4-5(3-14-17)10(18)19/h1-4H,(H,15,16)(H,18,19)" 014 InChIKey InChI 1.03 VOINEICHGDKMIS-UHFFFAOYSA-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 014 "SYSTEMATIC NAME" ACDLabs 12.01 "1-(5-chloro-6-fluoro-1H-benzimidazol-2-yl)-1H-pyrazole-4-carboxylic acid" 014 "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.7.0 "1-(5-chloro-6-fluoro-1H-benzimidazol-2-yl)pyrazole-4-carboxylic acid" # loop_ _pdbx_chem_comp_audit.comp_id _pdbx_chem_comp_audit.action_type _pdbx_chem_comp_audit.date _pdbx_chem_comp_audit.processing_site 014 "Create component" 2010-09-15 RCSB 014 "Modify aromatic_flag" 2011-06-04 RCSB 014 "Modify descriptor" 2011-06-04 RCSB #