data_6BC # _chem_comp.id 6BC _chem_comp.name "5-chloro-7-hydroxy-6-(phenylmethyl)pyrazolo[1,5-a]pyrimidine-3-carbonitrile" _chem_comp.type non-polymer _chem_comp.pdbx_type HETAIN _chem_comp.formula "C14 H9 Cl N4 O" _chem_comp.mon_nstd_parent_comp_id ? _chem_comp.pdbx_synonyms ? _chem_comp.pdbx_formal_charge 0 _chem_comp.pdbx_initial_date 2011-03-11 _chem_comp.pdbx_modified_date 2011-08-19 _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 284.700 _chem_comp.one_letter_code ? _chem_comp.three_letter_code 6BC _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 2YC5 _chem_comp.pdbx_subcomponent_list ? _chem_comp.pdbx_processing_site EBI # 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 6BC CL17 CL17 CL 0 0 N N N 13.885 58.716 -17.398 -0.662 -2.562 0.784 CL17 6BC 1 6BC C16 C16 C 0 1 Y N N 15.374 58.310 -18.218 0.251 -1.098 0.589 C16 6BC 2 6BC N18 N18 N 0 1 Y N N 16.130 59.362 -18.503 1.477 -1.147 0.108 N18 6BC 3 6BC C4 C4 C 0 1 Y N N 17.257 59.047 -19.163 2.198 -0.036 -0.051 C4 6BC 4 6BC C8 C8 C 0 1 Y N N 15.630 56.963 -18.515 -0.319 0.128 0.934 C8 6BC 5 6BC C6 C6 C 0 1 Y N N 16.808 56.701 -19.224 0.410 1.273 0.775 C6 6BC 6 6BC O7 O7 O 0 1 N N N 17.160 55.489 -19.565 -0.118 2.474 1.103 O7 6BC 7 6BC N5 N5 N 0 1 Y N N 17.617 57.794 -19.471 1.682 1.186 0.280 N5 6BC 8 6BC N19 N19 N 0 1 Y N N 18.816 57.730 -20.179 2.653 2.156 0.008 N19 6BC 9 6BC C20 C20 C 0 1 Y N N 19.240 59.007 -20.270 3.724 1.580 -0.469 C20 6BC 10 6BC C1 C1 C 0 1 Y N N 18.269 59.802 -19.651 3.501 0.192 -0.531 C1 6BC 11 6BC C2 C2 C 0 1 N N N 18.356 61.132 -19.547 4.424 -0.800 -0.995 C2 6BC 12 6BC N3 N3 N 0 1 N N N 18.431 62.277 -19.446 5.156 -1.587 -1.363 N3 6BC 13 6BC C9 C9 C 0 1 N N N 14.674 55.901 -18.109 -1.724 0.189 1.477 C9 6BC 14 6BC C10 C10 C 0 1 Y N N 13.689 55.366 -19.114 -2.703 0.224 0.333 C10 6BC 15 6BC C15 C15 C 0 1 Y N N 14.018 55.184 -20.439 -3.203 -0.956 -0.186 C15 6BC 16 6BC C14 C14 C 0 1 Y N N 13.042 54.652 -21.312 -4.101 -0.924 -1.236 C14 6BC 17 6BC C13 C13 C 0 1 Y N N 11.774 54.337 -20.863 -4.501 0.289 -1.766 C13 6BC 18 6BC C12 C12 C 0 1 Y N N 11.456 54.600 -19.534 -4.003 1.469 -1.247 C12 6BC 19 6BC C11 C11 C 0 1 Y N N 12.432 55.074 -18.682 -3.107 1.437 -0.194 C11 6BC 20 6BC H91C H91C H 0 0 N N N 15.284 55.043 -17.789 -1.914 -0.691 2.092 H91C 6BC 21 6BC H92C H92C H 0 0 N N N 14.042 56.389 -17.353 -1.840 1.088 2.083 H92C 6BC 22 6BC H20 H20 H 0 1 N N N 20.154 59.350 -20.732 4.631 2.085 -0.766 H20 6BC 23 6BC H15 H15 H 0 1 N N N 15.001 55.442 -20.803 -2.890 -1.903 0.228 H15 6BC 24 6BC H11 H11 H 0 1 N N N 12.191 55.218 -17.639 -2.721 2.359 0.214 H11 6BC 25 6BC H14 H14 H 0 1 N N N 13.292 54.489 -22.350 -4.491 -1.845 -1.642 H14 6BC 26 6BC H13 H13 H 0 1 N N N 11.046 53.897 -21.528 -5.203 0.314 -2.587 H13 6BC 27 6BC H12 H12 H 0 1 N N N 10.452 54.434 -19.172 -4.315 2.416 -1.662 H12 6BC 28 6BC H7 H7 H 0 1 N N N 17.245 55.438 -20.510 0.479 3.220 0.953 H7 6BC 29 # 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 6BC CL17 C16 SING N N 1 6BC C16 N18 DOUB Y N 2 6BC C16 C8 SING Y N 3 6BC N18 C4 SING Y N 4 6BC C4 N5 SING Y N 5 6BC C4 C1 DOUB Y N 6 6BC C8 C6 DOUB Y N 7 6BC C8 C9 SING N N 8 6BC C6 O7 SING N N 9 6BC C6 N5 SING Y N 10 6BC N5 N19 SING Y N 11 6BC N19 C20 DOUB Y N 12 6BC C20 C1 SING Y N 13 6BC C1 C2 SING N N 14 6BC C2 N3 TRIP N N 15 6BC C9 C10 SING N N 16 6BC C10 C15 SING Y N 17 6BC C10 C11 DOUB Y N 18 6BC C15 C14 DOUB Y N 19 6BC C14 C13 SING Y N 20 6BC C13 C12 DOUB Y N 21 6BC C12 C11 SING Y N 22 6BC C9 H91C SING N N 23 6BC C9 H92C SING N N 24 6BC C20 H20 SING N N 25 6BC C15 H15 SING N N 26 6BC C11 H11 SING N N 27 6BC C14 H14 SING N N 28 6BC C13 H13 SING N N 29 6BC C12 H12 SING N N 30 6BC O7 H7 SING N N 31 # 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 6BC SMILES_CANONICAL CACTVS 3.352 "Oc1n2ncc(C#N)c2nc(Cl)c1Cc3ccccc3" 6BC SMILES CACTVS 3.352 "Oc1n2ncc(C#N)c2nc(Cl)c1Cc3ccccc3" 6BC SMILES_CANONICAL "OpenEye OEToolkits" 1.6.1 "c1ccc(cc1)Cc2c(nc3c(cnn3c2O)C#N)Cl" 6BC SMILES "OpenEye OEToolkits" 1.6.1 "c1ccc(cc1)Cc2c(nc3c(cnn3c2O)C#N)Cl" 6BC InChI InChI 1.03 "InChI=1S/C14H9ClN4O/c15-12-11(6-9-4-2-1-3-5-9)14(20)19-13(18-12)10(7-16)8-17-19/h1-5,8,20H,6H2" 6BC InChIKey InChI 1.03 HOHNWEMSRSQMGQ-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 6BC "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.6.1 "5-chloro-7-hydroxy-6-(phenylmethyl)pyrazolo[1,5-a]pyrimidine-3-carbonitrile" # loop_ _pdbx_chem_comp_audit.comp_id _pdbx_chem_comp_audit.action_type _pdbx_chem_comp_audit.date _pdbx_chem_comp_audit.processing_site 6BC "Create component" 2011-03-11 EBI 6BC "Modify name" 2011-03-21 EBI 6BC "Modify formula" 2011-03-21 EBI 6BC "Other modification" 2011-03-21 EBI 6BC "Modify aromatic_flag" 2011-06-04 RCSB 6BC "Modify descriptor" 2011-06-04 RCSB #