data_S19 # _chem_comp.id S19 _chem_comp.name "2-{[(3R,4R)-3-aminotetrahydro-2H-pyran-4-yl]amino}-4-[(4-methylphenyl)amino]pyrimidine-5-carboxamide" _chem_comp.type NON-POLYMER _chem_comp.pdbx_type HETAIN _chem_comp.formula "C17 H22 N6 O2" _chem_comp.mon_nstd_parent_comp_id ? _chem_comp.pdbx_synonyms GSK143 _chem_comp.pdbx_formal_charge 0 _chem_comp.pdbx_initial_date 2011-07-12 _chem_comp.pdbx_modified_date 2020-06-17 _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 342.396 _chem_comp.one_letter_code ? _chem_comp.three_letter_code S19 _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 3SRV _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 S19 C1 C1 C 0 1 N N N -0.616 20.313 -71.519 -3.534 4.932 0.032 C1 S19 1 S19 C2 C2 C 0 1 Y N N 0.844 20.116 -71.256 -3.286 3.446 0.063 C2 S19 2 S19 C3 C3 C 0 1 Y N N 1.588 19.264 -72.044 -4.240 2.576 -0.433 C3 S19 3 S19 C4 C4 C 0 1 Y N N 2.934 19.061 -71.807 -4.016 1.214 -0.406 C4 S19 4 S19 C5 C5 C 0 1 Y N N 3.571 19.712 -70.767 -2.830 0.717 0.120 C5 S19 5 S19 N6 N6 N 0 1 N N N 4.955 19.499 -70.565 -2.599 -0.661 0.148 N6 S19 6 S19 C7 C7 C 0 1 Y N N 5.705 19.802 -69.405 -1.314 -1.149 0.020 C7 S19 7 S19 N8 N8 N 0 1 Y N N 5.185 20.479 -68.363 -0.281 -0.318 -0.054 N8 S19 8 S19 C9 C9 C 0 1 Y N N 5.985 20.701 -67.294 0.954 -0.782 -0.176 C9 S19 9 S19 N10 N10 N 0 1 N N N 5.449 21.377 -66.262 2.000 0.114 -0.250 N10 S19 10 S19 C11 C11 C 0 1 N N R 4.041 21.693 -66.107 3.375 -0.375 -0.386 C11 S19 11 S19 C12 C12 C 0 1 N N N 3.868 22.975 -65.321 3.947 -0.688 1.000 C12 S19 12 S19 C13 C13 C 0 1 N N N 2.398 23.346 -65.337 4.004 0.602 1.824 C13 S19 13 S19 O14 O14 O 0 1 N N N 1.670 22.290 -64.738 4.796 1.571 1.134 O14 S19 14 S19 C15 C15 C 0 1 N N N 1.718 21.102 -65.508 4.283 1.938 -0.148 C15 S19 15 S19 C16 C16 C 0 1 N N R 3.166 20.591 -65.530 4.238 0.702 -1.051 C16 S19 16 S19 N17 N17 N 0 1 N N N 3.526 20.235 -64.156 3.656 1.064 -2.350 N17 S19 17 S19 N18 N18 N 0 1 Y N N 7.257 20.304 -67.181 1.216 -2.083 -0.231 N18 S19 18 S19 C19 C19 C 0 1 Y N N 7.764 19.640 -68.221 0.247 -2.977 -0.164 C19 S19 19 S19 C20 C20 C 0 1 Y N N 7.068 19.345 -69.366 -1.075 -2.539 -0.029 C20 S19 20 S19 C21 C21 C 0 1 N N N 7.716 18.588 -70.454 -2.185 -3.501 0.055 C21 S19 21 S19 N22 N22 N 0 1 N N N 9.075 18.483 -70.367 -1.929 -4.822 0.134 N22 S19 22 S19 O23 O23 O 0 1 N N N 7.055 18.064 -71.328 -3.335 -3.105 0.053 O23 S19 23 S19 C24 C24 C 0 1 Y N N 2.820 20.567 -69.988 -1.873 1.593 0.617 C24 S19 24 S19 C25 C25 C 0 1 Y N N 1.464 20.768 -70.205 -2.102 2.955 0.582 C25 S19 25 S19 H1 H1 H 0 1 N N N -1.195 19.570 -70.951 -3.164 5.343 -0.907 H1 S19 26 S19 H1A H1A H 0 1 N N N -0.912 21.325 -71.206 -4.604 5.123 0.115 H1A S19 27 S19 H1B H1B H 0 1 N N N -0.815 20.189 -72.594 -3.015 5.405 0.865 H1B S19 28 S19 H3 H3 H 0 1 N N N 1.110 18.746 -72.862 -5.162 2.963 -0.841 H3 S19 29 S19 H4 H4 H 0 1 N N N 3.493 18.388 -72.440 -4.761 0.535 -0.793 H4 S19 30 S19 HN6 HN6 H 0 1 N N N 5.458 19.089 -71.326 -3.342 -1.275 0.258 HN6 S19 31 S19 HN10 HN10 H 0 0 N N N 5.672 20.825 -65.458 1.826 1.067 -0.211 HN10 S19 32 S19 H11 H11 H 0 1 N N N 3.676 21.817 -67.137 3.382 -1.277 -0.997 H11 S19 33 S19 H12 H12 H 0 1 N N N 4.205 22.827 -64.285 3.307 -1.413 1.503 H12 S19 34 S19 H12A H12A H 0 0 N N N 4.462 23.779 -65.781 4.951 -1.099 0.896 H12A S19 35 S19 H13 H13 H 0 1 N N N 2.240 24.277 -64.773 2.994 0.989 1.962 H13 S19 36 S19 H13A H13A H 0 0 N N N 2.060 23.493 -66.373 4.450 0.393 2.796 H13A S19 37 S19 H15 H15 H 0 1 N N N 1.062 20.341 -65.060 3.278 2.343 -0.036 H15 S19 38 S19 H15A H15A H 0 0 N N N 1.381 21.310 -66.534 4.931 2.691 -0.596 H15A S19 39 S19 H16 H16 H 0 1 N N N 3.299 19.698 -66.159 5.248 0.320 -1.197 H16 S19 40 S19 HN17 HN17 H 0 0 N N N 2.921 19.509 -63.830 4.208 1.773 -2.808 HN17 S19 41 S19 HN1A HN1A H 0 0 N N N 4.473 19.915 -64.132 3.551 0.251 -2.938 HN1A S19 42 S19 H19 H19 H 0 1 N N N 8.791 19.313 -68.157 0.472 -4.032 -0.210 H19 S19 43 S19 HN22 HN22 H 0 0 N N N 9.580 17.951 -71.047 -1.012 -5.139 0.135 HN22 S19 44 S19 HN2A HN2A H 0 0 N N N 9.565 18.938 -69.623 -2.661 -5.456 0.189 HN2A S19 45 S19 H24 H24 H 0 1 N N N 3.304 21.098 -69.182 -0.950 1.211 1.027 H24 S19 46 S19 H25 H25 H 0 1 N N N 0.899 21.426 -69.561 -1.357 3.637 0.964 H25 S19 47 # # 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 S19 C1 C2 SING N N 1 S19 C1 H1 SING N N 2 S19 C1 H1A SING N N 3 S19 C1 H1B SING N N 4 S19 C3 C2 DOUB Y N 5 S19 C2 C25 SING Y N 6 S19 C3 C4 SING Y N 7 S19 C3 H3 SING N N 8 S19 C4 C5 DOUB Y N 9 S19 C4 H4 SING N N 10 S19 C5 N6 SING N N 11 S19 C5 C24 SING Y N 12 S19 N6 C7 SING N N 13 S19 N6 HN6 SING N N 14 S19 C7 C20 DOUB Y N 15 S19 C7 N8 SING Y N 16 S19 N8 C9 DOUB Y N 17 S19 C9 N18 SING Y N 18 S19 C9 N10 SING N N 19 S19 N10 C11 SING N N 20 S19 N10 HN10 SING N N 21 S19 C11 C16 SING N N 22 S19 C11 C12 SING N N 23 S19 C11 H11 SING N N 24 S19 C13 C12 SING N N 25 S19 C12 H12 SING N N 26 S19 C12 H12A SING N N 27 S19 C13 O14 SING N N 28 S19 C13 H13 SING N N 29 S19 C13 H13A SING N N 30 S19 C15 O14 SING N N 31 S19 C16 C15 SING N N 32 S19 C15 H15 SING N N 33 S19 C15 H15A SING N N 34 S19 C16 N17 SING N N 35 S19 C16 H16 SING N N 36 S19 N17 HN17 SING N N 37 S19 N17 HN1A SING N N 38 S19 C19 N18 DOUB Y N 39 S19 C20 C19 SING Y N 40 S19 C19 H19 SING N N 41 S19 C21 C20 SING N N 42 S19 O23 C21 DOUB N N 43 S19 C21 N22 SING N N 44 S19 N22 HN22 SING N N 45 S19 N22 HN2A SING N N 46 S19 C25 C24 DOUB Y N 47 S19 C24 H24 SING N N 48 S19 C25 H25 SING N N 49 # # 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 S19 SMILES ACDLabs 12.01 "O=C(N)c1c(nc(nc1)NC2CCOCC2N)Nc3ccc(cc3)C" S19 InChI InChI 1.03 "InChI=1S/C17H22N6O2/c1-10-2-4-11(5-3-10)21-16-12(15(19)24)8-20-17(23-16)22-14-6-7-25-9-13(14)18/h2-5,8,13-14H,6-7,9,18H2,1H3,(H2,19,24)(H2,20,21,22,23)/t13-,14+/m0/s1" S19 InChIKey InChI 1.03 KBPYMFSSFLOJPH-UONOGXRCSA-N S19 SMILES_CANONICAL CACTVS 3.370 "Cc1ccc(Nc2nc(N[C@@H]3CCOC[C@@H]3N)ncc2C(N)=O)cc1" S19 SMILES CACTVS 3.370 "Cc1ccc(Nc2nc(N[CH]3CCOC[CH]3N)ncc2C(N)=O)cc1" S19 SMILES_CANONICAL "OpenEye OEToolkits" 1.7.2 "Cc1ccc(cc1)Nc2c(cnc(n2)N[C@@H]3CCOC[C@@H]3N)C(=O)N" S19 SMILES "OpenEye OEToolkits" 1.7.2 "Cc1ccc(cc1)Nc2c(cnc(n2)NC3CCOCC3N)C(=O)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 S19 "SYSTEMATIC NAME" ACDLabs 12.01 "2-{[(3R,4R)-3-aminotetrahydro-2H-pyran-4-yl]amino}-4-[(4-methylphenyl)amino]pyrimidine-5-carboxamide" S19 "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.7.2 "2-[[(3R,4R)-3-azanyloxan-4-yl]amino]-4-[(4-methylphenyl)amino]pyrimidine-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 S19 "Create component" 2011-07-12 RCSB S19 "Modify synonyms" 2020-06-05 PDBE # _pdbx_chem_comp_synonyms.ordinal 1 _pdbx_chem_comp_synonyms.comp_id S19 _pdbx_chem_comp_synonyms.name GSK143 _pdbx_chem_comp_synonyms.provenance ? _pdbx_chem_comp_synonyms.type ? ##