data_1OB # _chem_comp.id 1OB _chem_comp.name "5-(4-cyanobenzyl)-N-(4-fluorophenyl)-7-hydroxypyrazolo[1,5-a]pyrimidine-3-carboxamide" _chem_comp.type NON-POLYMER _chem_comp.pdbx_type HETAIN _chem_comp.formula "C21 H14 F N5 O2" _chem_comp.mon_nstd_parent_comp_id ? _chem_comp.pdbx_synonyms ? _chem_comp.pdbx_formal_charge 0 _chem_comp.pdbx_initial_date 2013-04-09 _chem_comp.pdbx_modified_date 2013-05-10 _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 387.367 _chem_comp.one_letter_code ? _chem_comp.three_letter_code 1OB _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 4K18 _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 1OB C1 C1 C 0 1 Y N N -18.174 -35.613 5.268 -1.788 2.918 -1.268 C1 1OB 1 1OB C2 C2 C 0 1 Y N N -18.500 -36.944 5.471 -0.592 3.605 -1.254 C2 1OB 2 1OB C3 C3 C 0 1 Y N N -19.830 -37.308 5.708 -0.022 3.983 -0.036 C3 1OB 3 1OB C4 C4 C 0 1 Y N N -20.823 -36.323 5.726 -0.669 3.662 1.159 C4 1OB 4 1OB C5 C5 C 0 1 Y N N -20.475 -34.998 5.514 -1.864 2.974 1.130 C5 1OB 5 1OB C6 C6 C 0 1 Y N N -19.157 -34.641 5.279 -2.423 2.603 -0.080 C6 1OB 6 1OB C7 C7 C 0 1 N N N -18.785 -33.196 5.064 -3.730 1.853 -0.104 C7 1OB 7 1OB C8 C8 C 0 1 Y N N -18.104 -32.924 3.745 -3.459 0.371 -0.060 C8 1OB 8 1OB C9 C9 C 0 1 Y N N -17.283 -31.804 3.644 -4.522 -0.530 -0.072 C9 1OB 9 1OB C10 C10 C 0 1 Y N N -16.664 -31.548 2.451 -4.262 -1.873 -0.033 C10 1OB 10 1OB N11 N11 N 0 1 Y N N -16.872 -32.363 1.389 -2.963 -2.295 0.017 N11 1OB 11 1OB C12 C12 C 0 1 Y N N -17.691 -33.438 1.531 -1.953 -1.375 0.028 C12 1OB 12 1OB N13 N13 N 0 1 Y N N -18.292 -33.707 2.694 -2.218 -0.069 -0.016 N13 1OB 13 1OB C14 C14 C 0 1 Y N N -17.700 -34.076 0.285 -0.747 -2.100 0.083 C14 1OB 14 1OB C15 C15 C 0 1 Y N N -16.883 -33.342 -0.585 -1.090 -3.465 0.104 C15 1OB 15 1OB N16 N16 N 0 1 Y N N -16.385 -32.333 0.078 -2.392 -3.571 0.071 N16 1OB 16 1OB C17 C17 C 0 1 N N N -18.485 -35.251 -0.038 0.606 -1.540 0.112 C17 1OB 17 1OB O18 O18 O 0 1 N N N -18.442 -35.696 -1.171 0.766 -0.333 0.088 O18 1OB 18 1OB N19 N19 N 0 1 N N N -19.261 -35.731 0.963 1.674 -2.361 0.165 N19 1OB 19 1OB C20 C20 C 0 1 Y N N -20.138 -36.823 0.939 2.968 -1.831 0.095 C20 1OB 20 1OB C21 C21 C 0 1 Y N N -20.664 -37.243 2.157 3.248 -0.601 0.675 C21 1OB 21 1OB C22 C22 C 0 1 Y N N -21.539 -38.310 2.212 4.525 -0.080 0.605 C22 1OB 22 1OB C23 C23 C 0 1 Y N N -21.895 -38.958 1.041 5.526 -0.784 -0.044 C23 1OB 23 1OB C24 C24 C 0 1 Y N N -21.379 -38.550 -0.176 5.249 -2.010 -0.624 C24 1OB 24 1OB C25 C25 C 0 1 Y N N -20.507 -37.477 -0.231 3.974 -2.538 -0.550 C25 1OB 25 1OB F26 F26 F 0 1 N N N -22.745 -40.003 1.083 6.775 -0.273 -0.112 F26 1OB 26 1OB O27 O27 O 0 1 N N N -15.866 -30.481 2.277 -5.275 -2.768 -0.044 O27 1OB 27 1OB C28 C28 C 0 1 N N N -20.168 -38.677 5.925 1.219 4.695 -0.014 C28 1OB 28 1OB N29 N29 N 0 1 N N N -20.428 -39.768 6.096 2.204 5.261 0.004 N29 1OB 29 1OB H1 H1 H 0 1 N N N -17.145 -35.333 5.100 -2.232 2.628 -2.209 H1 1OB 30 1OB H2 H2 H 0 1 N N N -17.729 -37.700 5.446 -0.097 3.849 -2.182 H2 1OB 31 1OB H3 H3 H 0 1 N N N -21.854 -36.593 5.904 -0.233 3.951 2.104 H3 1OB 32 1OB H4 H4 H 0 1 N N N -21.240 -34.236 5.532 -2.365 2.725 2.054 H4 1OB 33 1OB H5 H5 H 0 1 N N N -18.105 -32.890 5.873 -4.329 2.138 0.762 H5 1OB 34 1OB H6 H6 H 0 1 N N N -19.704 -32.593 5.109 -4.272 2.096 -1.017 H6 1OB 35 1OB H7 H7 H 0 1 N N N -17.138 -31.150 4.491 -5.540 -0.172 -0.112 H7 1OB 36 1OB H9 H9 H 0 1 N N N -16.697 -33.571 -1.624 -0.393 -4.289 0.148 H9 1OB 37 1OB H10 H10 H 0 1 N N N -19.200 -35.242 1.833 1.546 -3.318 0.252 H10 1OB 38 1OB H11 H11 H 0 1 N N N -20.386 -36.731 3.066 2.468 -0.052 1.181 H11 1OB 39 1OB H12 H12 H 0 1 N N N -21.942 -38.636 3.159 4.744 0.876 1.056 H12 1OB 40 1OB H13 H13 H 0 1 N N N -21.656 -39.068 -1.082 6.030 -2.557 -1.130 H13 1OB 41 1OB H14 H14 H 0 1 N N N -20.114 -37.148 -1.181 3.758 -3.494 -1.002 H14 1OB 42 1OB H8 H8 H 0 1 N N N -15.803 -29.996 3.091 -6.154 -2.367 -0.080 H8 1OB 43 # 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 1OB O18 C17 DOUB N N 1 1OB C15 N16 DOUB Y N 2 1OB C15 C14 SING Y N 3 1OB C25 C24 DOUB Y N 4 1OB C25 C20 SING Y N 5 1OB C24 C23 SING Y N 6 1OB C17 C14 SING N N 7 1OB C17 N19 SING N N 8 1OB N16 N11 SING Y N 9 1OB C14 C12 DOUB Y N 10 1OB C20 N19 SING N N 11 1OB C20 C21 DOUB Y N 12 1OB C23 F26 SING N N 13 1OB C23 C22 DOUB Y N 14 1OB N11 C12 SING Y N 15 1OB N11 C10 SING Y N 16 1OB C12 N13 SING Y N 17 1OB C21 C22 SING Y N 18 1OB O27 C10 SING N N 19 1OB C10 C9 DOUB Y N 20 1OB N13 C8 DOUB Y N 21 1OB C9 C8 SING Y N 22 1OB C8 C7 SING N N 23 1OB C7 C6 SING N N 24 1OB C1 C6 DOUB Y N 25 1OB C1 C2 SING Y N 26 1OB C6 C5 SING Y N 27 1OB C2 C3 DOUB Y N 28 1OB C5 C4 DOUB Y N 29 1OB C3 C4 SING Y N 30 1OB C3 C28 SING N N 31 1OB C28 N29 TRIP N N 32 1OB C1 H1 SING N N 33 1OB C2 H2 SING N N 34 1OB C4 H3 SING N N 35 1OB C5 H4 SING N N 36 1OB C7 H5 SING N N 37 1OB C7 H6 SING N N 38 1OB C9 H7 SING N N 39 1OB C15 H9 SING N N 40 1OB N19 H10 SING N N 41 1OB C21 H11 SING N N 42 1OB C22 H12 SING N N 43 1OB C24 H13 SING N N 44 1OB C25 H14 SING N N 45 1OB O27 H8 SING N N 46 # 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 1OB SMILES ACDLabs 12.01 "Fc1ccc(cc1)NC(=O)c2c3nc(cc(O)n3nc2)Cc4ccc(C#N)cc4" 1OB InChI InChI 1.03 "InChI=1S/C21H14FN5O2/c22-15-5-7-16(8-6-15)26-21(29)18-12-24-27-19(28)10-17(25-20(18)27)9-13-1-3-14(11-23)4-2-13/h1-8,10,12,28H,9H2,(H,26,29)" 1OB InChIKey InChI 1.03 GVDYBVYAFKPQRT-UHFFFAOYSA-N 1OB SMILES_CANONICAL CACTVS 3.370 "Oc1cc(Cc2ccc(cc2)C#N)nc3n1ncc3C(=O)Nc4ccc(F)cc4" 1OB SMILES CACTVS 3.370 "Oc1cc(Cc2ccc(cc2)C#N)nc3n1ncc3C(=O)Nc4ccc(F)cc4" 1OB SMILES_CANONICAL "OpenEye OEToolkits" 1.7.6 "c1cc(ccc1Cc2cc(n3c(n2)c(cn3)C(=O)Nc4ccc(cc4)F)O)C#N" 1OB SMILES "OpenEye OEToolkits" 1.7.6 "c1cc(ccc1Cc2cc(n3c(n2)c(cn3)C(=O)Nc4ccc(cc4)F)O)C#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 1OB "SYSTEMATIC NAME" ACDLabs 12.01 "5-(4-cyanobenzyl)-N-(4-fluorophenyl)-7-hydroxypyrazolo[1,5-a]pyrimidine-3-carboxamide" 1OB "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.7.6 "5-[(4-cyanophenyl)methyl]-N-(4-fluorophenyl)-7-oxidanyl-pyrazolo[1,5-a]pyrimidine-3-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 1OB "Create component" 2013-04-09 RCSB 1OB "Initial release" 2013-05-15 RCSB #