data_4W4 # _chem_comp.id 4W4 _chem_comp.name "5-butyl-2-[(4-chloro-2-fluorobenzyl)amino]-7-oxo-4,7-dihydropyrazolo[1,5-a]pyrimidine-3-carbonitrile" _chem_comp.type NON-POLYMER _chem_comp.pdbx_type HETAIN _chem_comp.formula "C18 H17 Cl F N5 O" _chem_comp.mon_nstd_parent_comp_id ? _chem_comp.pdbx_synonyms ? _chem_comp.pdbx_formal_charge 0 _chem_comp.pdbx_initial_date 2015-06-09 _chem_comp.pdbx_modified_date 2015-06-26 _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 373.812 _chem_comp.one_letter_code ? _chem_comp.three_letter_code 4W4 _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 5BWX _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 4W4 C1 C1 C 0 1 N N N -3.704 40.788 21.601 8.590 1.802 -1.628 C1 4W4 1 4W4 C2 C2 C 0 1 N N N -4.671 40.167 22.601 8.023 1.227 -0.328 C2 4W4 2 4W4 C3 C3 C 0 1 N N N -5.476 39.027 21.968 6.597 0.729 -0.570 C3 4W4 3 4W4 C4 C4 C 0 1 N N N -6.711 38.558 22.730 6.030 0.154 0.730 C4 4W4 4 4W4 C5 C5 C 0 1 N N N -7.565 39.685 23.122 4.625 -0.336 0.492 C5 4W4 5 4W4 C6 C6 C 0 1 N N N -7.569 40.239 24.338 4.403 -1.637 0.198 C6 4W4 6 4W4 C7 C7 C 0 1 N N N -8.385 41.395 24.716 3.085 -2.088 -0.023 C7 4W4 7 4W4 O8 O1 O 0 1 N N N -8.431 41.947 25.814 2.876 -3.259 -0.288 O8 4W4 8 4W4 N9 N1 N 0 1 Y N N -9.124 41.839 23.631 2.056 -1.219 0.059 N9 4W4 9 4W4 N10 N2 N 0 1 Y N N -9.968 42.930 23.737 0.677 -1.387 -0.110 N10 4W4 10 4W4 C11 C8 C 0 1 Y N N -10.499 43.050 22.520 0.077 -0.237 0.073 C11 4W4 11 4W4 N12 N3 N 0 1 N N N -11.398 44.025 22.212 -1.295 -0.010 -0.012 N12 4W4 12 4W4 C13 C9 C 0 1 N N N -11.614 45.246 23.030 -2.202 -1.115 -0.331 C13 4W4 13 4W4 C14 C10 C 0 1 Y N N -11.965 46.350 22.083 -3.621 -0.608 -0.361 C14 4W4 14 4W4 C15 C11 C 0 1 Y N N -13.253 46.765 21.831 -4.263 -0.424 -1.571 C15 4W4 15 4W4 C16 C12 C 0 1 Y N N -13.535 47.743 20.906 -5.564 0.040 -1.600 C16 4W4 16 4W4 C17 C13 C 0 1 Y N N -12.508 48.335 20.208 -6.226 0.322 -0.418 C17 4W4 17 4W4 CL1 CL1 CL 0 0 N N N -12.877 49.542 19.028 -7.858 0.912 -0.456 CL1 4W4 18 4W4 C19 C14 C 0 1 Y N N -11.205 47.947 20.448 -5.584 0.139 0.794 C19 4W4 19 4W4 C20 C15 C 0 1 Y N N -10.955 46.958 21.371 -4.283 -0.331 0.823 C20 4W4 20 4W4 F21 F1 F 0 1 N N N -9.692 46.576 21.582 -3.655 -0.511 2.006 F21 4W4 21 4W4 C22 C16 C 0 1 Y N N -10.008 42.051 21.642 1.063 0.737 0.372 C22 4W4 22 4W4 C23 C17 C 0 1 N N N -10.335 41.844 20.286 0.836 2.125 0.640 C23 4W4 23 4W4 N24 N4 N 0 1 N N N -10.600 41.657 19.176 0.655 3.226 0.854 N24 4W4 24 4W4 C25 C18 C 0 1 Y N N -9.134 41.295 22.385 2.295 0.087 0.355 C25 4W4 25 4W4 N26 N5 N 0 1 N N N -8.362 40.226 22.103 3.576 0.530 0.577 N26 4W4 26 4W4 H1 H1 H 0 1 N N N -3.144 41.600 22.087 9.606 2.157 -1.455 H1 4W4 27 4W4 H2 H2 H 0 1 N N N -3.001 40.020 21.246 8.601 1.026 -2.394 H2 4W4 28 4W4 H3 H3 H 0 1 N N N -4.268 41.192 20.747 7.967 2.632 -1.960 H3 4W4 29 4W4 H4 H4 H 0 1 N N N -4.099 39.771 23.453 8.647 0.397 0.004 H4 4W4 30 4W4 H5 H5 H 0 1 N N N -5.366 40.942 22.955 8.012 2.003 0.438 H5 4W4 31 4W4 H6 H6 H 0 1 N N N -5.805 39.363 20.974 5.974 1.559 -0.902 H6 4W4 32 4W4 H7 H7 H 0 1 N N N -4.803 38.164 21.859 6.608 -0.046 -1.336 H7 4W4 33 4W4 H8 H8 H 0 1 N N N -7.290 37.878 22.088 6.654 -0.676 1.062 H8 4W4 34 4W4 H9 H9 H 0 1 N N N -6.390 38.022 23.635 6.019 0.930 1.496 H9 4W4 35 4W4 H10 H10 H 0 1 N N N -6.928 39.806 25.092 5.230 -2.328 0.133 H10 4W4 36 4W4 H12 H12 H 0 1 N N N -11.143 44.351 21.302 -1.650 0.880 0.140 H12 4W4 37 4W4 H13 H13 H 0 1 N N N -10.696 45.499 23.581 -1.943 -1.529 -1.306 H13 4W4 38 4W4 H14 H14 H 0 1 N N N -12.436 45.083 23.742 -2.110 -1.892 0.429 H14 4W4 39 4W4 H15 H15 H 0 1 N N N -14.066 46.309 22.376 -3.748 -0.644 -2.495 H15 4W4 40 4W4 H16 H16 H 0 1 N N N -14.557 48.044 20.729 -6.065 0.184 -2.546 H16 4W4 41 4W4 H17 H17 H 0 1 N N N -10.390 48.415 19.916 -6.100 0.359 1.717 H17 4W4 42 4W4 H11 H11 H 0 1 N N N -8.358 39.827 21.186 3.734 1.462 0.792 H11 4W4 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 4W4 CL1 C17 SING N N 1 4W4 N24 C23 TRIP N N 2 4W4 C17 C19 DOUB Y N 3 4W4 C17 C16 SING Y N 4 4W4 C23 C22 SING N N 5 4W4 C19 C20 SING Y N 6 4W4 C16 C15 DOUB Y N 7 4W4 C20 F21 SING N N 8 4W4 C20 C14 DOUB Y N 9 4W4 C1 C2 SING N N 10 4W4 C22 C25 DOUB Y N 11 4W4 C22 C11 SING Y N 12 4W4 C15 C14 SING Y N 13 4W4 C3 C2 SING N N 14 4W4 C3 C4 SING N N 15 4W4 C14 C13 SING N N 16 4W4 N26 C25 SING N N 17 4W4 N26 C5 SING N N 18 4W4 N12 C11 SING N N 19 4W4 N12 C13 SING N N 20 4W4 C25 N9 SING Y N 21 4W4 C11 N10 DOUB Y N 22 4W4 C4 C5 SING N N 23 4W4 C5 C6 DOUB N N 24 4W4 N9 N10 SING Y N 25 4W4 N9 C7 SING N N 26 4W4 C6 C7 SING N N 27 4W4 C7 O8 DOUB N N 28 4W4 C1 H1 SING N N 29 4W4 C1 H2 SING N N 30 4W4 C1 H3 SING N N 31 4W4 C2 H4 SING N N 32 4W4 C2 H5 SING N N 33 4W4 C3 H6 SING N N 34 4W4 C3 H7 SING N N 35 4W4 C4 H8 SING N N 36 4W4 C4 H9 SING N N 37 4W4 C6 H10 SING N N 38 4W4 N12 H12 SING N N 39 4W4 C13 H13 SING N N 40 4W4 C13 H14 SING N N 41 4W4 C15 H15 SING N N 42 4W4 C16 H16 SING N N 43 4W4 C19 H17 SING N N 44 4W4 N26 H11 SING N N 45 # 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 4W4 SMILES ACDLabs 12.01 "CCCCC3=CC(=O)n2nc(NCc1ccc(cc1F)Cl)c(c2N3)C#N" 4W4 InChI InChI 1.03 "InChI=1S/C18H17ClFN5O/c1-2-3-4-13-8-16(26)25-18(23-13)14(9-21)17(24-25)22-10-11-5-6-12(19)7-15(11)20/h5-8,23H,2-4,10H2,1H3,(H,22,24)" 4W4 InChIKey InChI 1.03 MRXJYWNXFPIXSE-UHFFFAOYSA-N 4W4 SMILES_CANONICAL CACTVS 3.385 "CCCCC1=CC(=O)n2nc(NCc3ccc(Cl)cc3F)c(C#N)c2N1" 4W4 SMILES CACTVS 3.385 "CCCCC1=CC(=O)n2nc(NCc3ccc(Cl)cc3F)c(C#N)c2N1" 4W4 SMILES_CANONICAL "OpenEye OEToolkits" 1.9.2 "CCCCC1=CC(=O)n2c(c(c(n2)NCc3ccc(cc3F)Cl)C#N)N1" 4W4 SMILES "OpenEye OEToolkits" 1.9.2 "CCCCC1=CC(=O)n2c(c(c(n2)NCc3ccc(cc3F)Cl)C#N)N1" # 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 4W4 "SYSTEMATIC NAME" ACDLabs 12.01 "5-butyl-2-[(4-chloro-2-fluorobenzyl)amino]-7-oxo-4,7-dihydropyrazolo[1,5-a]pyrimidine-3-carbonitrile" 4W4 "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.9.2 "5-butyl-2-[(4-chloranyl-2-fluoranyl-phenyl)methylamino]-7-oxidanylidene-4H-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 4W4 "Create component" 2015-06-09 EBI 4W4 "Initial release" 2015-07-01 RCSB #