data_21G # _chem_comp.id 21G _chem_comp.name "(2S,3S)-3-[[5-fluoranyl-2-(5-fluoranyl-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrimidin-4-yl]amino]bicyclo[2.2.2]octane-2-carboxylic acid" _chem_comp.type NON-POLYMER _chem_comp.pdbx_type HETAIN _chem_comp.formula "C20 H19 F2 N5 O2" _chem_comp.mon_nstd_parent_comp_id ? _chem_comp.pdbx_synonyms "3-[[5-fluoro-2-(5-fluoro-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrimidin-4-yl]amino]bicyclo[2.2.2]octane-2-carboxylic acid; VX787; (2S,3S)-3-((5-fluoro-2-(5-fluoro-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrimidin-4-yl)amino)bicyclo[2.2.2]octane-2-carboxylic acid" _chem_comp.pdbx_formal_charge 0 _chem_comp.pdbx_initial_date 2014-03-03 _chem_comp.pdbx_modified_date 2020-11-26 _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 399.394 _chem_comp.one_letter_code ? _chem_comp.three_letter_code 21G _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 4P1U _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 21G C1 C1 C 0 1 Y N N -47.410 -4.733 1.570 4.499 -0.598 0.106 C1 21G 1 21G C2 C2 C 0 1 Y N N -46.092 -4.886 1.157 5.829 -0.214 0.142 C2 21G 2 21G C3 C3 C 0 1 Y N N -45.699 -4.388 -0.079 6.156 1.122 -0.043 C3 21G 3 21G C5 C4 C 0 1 Y N N -47.838 -3.599 -0.528 3.942 1.722 -0.300 C5 21G 4 21G C6 C5 C 0 1 Y N N -48.299 -4.080 0.716 3.538 0.388 -0.121 C6 21G 5 21G C7 C6 C 0 1 Y N N -49.726 -3.736 0.781 2.071 0.385 -0.234 C7 21G 6 21G N4 N1 N 0 1 Y N N -46.556 -3.777 -0.878 5.230 2.034 -0.250 N4 21G 7 21G C8 C7 C 0 1 Y N N -50.038 -3.088 -0.369 1.700 1.670 -0.464 C8 21G 8 21G N9 N2 N 0 1 Y N N -48.919 -3.002 -1.154 2.803 2.468 -0.505 N9 21G 9 21G C11 C8 C 0 1 Y N N -50.614 -4.002 1.917 1.177 -0.787 -0.119 C11 21G 10 21G N12 N3 N 0 1 Y N N -51.874 -3.579 1.907 1.704 -1.982 0.115 N12 21G 11 21G C13 C9 C 0 1 Y N N -52.679 -3.787 2.945 0.935 -3.056 0.225 C13 21G 12 21G C14 C10 C 0 1 Y N N -52.168 -4.446 4.047 -0.435 -2.923 0.094 C14 21G 13 21G C15 C11 C 0 1 Y N N -50.836 -4.875 4.031 -0.962 -1.650 -0.153 C15 21G 14 21G N16 N4 N 0 1 Y N N -50.097 -4.625 2.961 -0.134 -0.617 -0.246 N16 21G 15 21G N17 N5 N 0 1 N N N -50.315 -5.536 5.133 -2.330 -1.470 -0.292 N17 21G 16 21G C18 C12 C 0 1 N N S -48.967 -6.104 5.195 -2.870 -0.133 -0.549 C18 21G 17 21G C20 C13 C 0 1 N N S -49.047 -7.290 6.184 -3.056 0.606 0.777 C20 21G 18 21G C22 C14 C 0 1 N N N -47.909 -7.189 7.226 -4.530 0.976 0.953 C22 21G 19 21G C23 C15 C 0 1 N N N -46.560 -7.040 6.510 -4.971 1.879 -0.201 C23 21G 20 21G C24 C16 C 0 1 N N N -46.549 -5.729 5.705 -4.785 1.140 -1.527 C24 21G 21 21G C25 C17 C 0 1 N N N -47.945 -5.085 5.734 -4.221 -0.256 -1.258 C25 21G 22 21G C26 C18 C 0 1 N N N -48.230 -4.714 7.205 -5.193 -1.037 -0.371 C26 21G 23 21G C27 C19 C 0 1 N N N -48.164 -5.961 8.109 -5.379 -0.298 0.955 C27 21G 24 21G C28 C20 C 0 1 N N N -49.026 -8.635 5.487 -2.221 1.861 0.775 C28 21G 25 21G O29 O1 O 0 1 N N N -49.333 -9.619 6.122 -0.889 1.779 0.633 O29 21G 26 21G O30 O2 O 0 1 N N N -48.673 -8.752 4.190 -2.750 2.939 0.900 O30 21G 27 21G F31 F1 F 0 1 N N N -52.930 -4.683 5.134 -1.247 -3.998 0.200 F31 21G 28 21G F32 F2 F 0 1 N N N -45.200 -5.519 1.956 6.798 -1.131 0.354 F32 21G 29 21G H1 H1 H 0 1 N N N -47.738 -5.110 2.528 4.214 -1.630 0.246 H1 21G 30 21G H2 H2 H 0 1 N N N -44.672 -4.503 -0.393 7.194 1.420 -0.015 H2 21G 31 21G H3 H3 H 0 1 N N N -51.013 -2.701 -0.625 0.683 2.009 -0.596 H3 21G 32 21G H4 H4 H 0 1 N N N -48.887 -2.568 -2.054 2.789 3.427 -0.656 H4 21G 33 21G H5 H5 H 0 1 N N N -53.705 -3.450 2.927 1.374 -4.024 0.415 H5 21G 34 21G H6 H6 H 0 1 N N N -50.367 -4.883 5.888 -2.929 -2.229 -0.219 H6 21G 35 21G H7 H7 H 0 1 N N N -48.648 -6.465 4.206 -2.178 0.423 -1.181 H7 21G 36 21G H8 H8 H 0 1 N N N -50.000 -7.205 6.726 -2.743 -0.038 1.599 H8 21G 37 21G H9 H9 H 0 1 N N N -47.899 -8.096 7.848 -4.663 1.502 1.898 H9 21G 38 21G H10 H10 H 0 1 N N N -46.411 -7.890 5.828 -6.021 2.143 -0.075 H10 21G 39 21G H11 H11 H 0 1 N N N -45.750 -7.020 7.254 -4.367 2.787 -0.202 H11 21G 40 21G H12 H12 H 0 1 N N N -46.268 -5.943 4.663 -5.747 1.052 -2.032 H12 21G 41 21G H13 H13 H 0 1 N N N -45.818 -5.036 6.147 -4.092 1.696 -2.159 H13 21G 42 21G H14 H14 H 0 1 N N N -47.954 -4.179 5.111 -4.088 -0.783 -2.203 H14 21G 43 21G H15 H15 H 0 1 N N N -47.481 -3.983 7.544 -6.155 -1.125 -0.876 H15 21G 44 21G H16 H16 H 0 1 N N N -49.234 -4.270 7.277 -4.791 -2.032 -0.180 H16 21G 45 21G H17 H17 H 0 1 N N N -47.345 -5.850 8.835 -5.065 -0.942 1.777 H17 21G 46 21G H18 H18 H 0 1 N N N -49.117 -6.081 8.646 -6.429 -0.035 1.081 H18 21G 47 21G H19 H19 H 0 1 N N N -49.274 -10.387 5.566 -0.395 2.611 0.637 H19 21G 48 # # 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 21G N9 C5 SING Y N 1 21G N9 C8 SING Y N 2 21G N4 C5 SING Y N 3 21G N4 C3 DOUB Y N 4 21G C5 C6 DOUB Y N 5 21G C8 C7 DOUB Y N 6 21G C3 C2 SING Y N 7 21G C6 C7 SING Y N 8 21G C6 C1 SING Y N 9 21G C7 C11 SING N N 10 21G C2 C1 DOUB Y N 11 21G C2 F32 SING N N 12 21G N12 C11 DOUB Y N 13 21G N12 C13 SING Y N 14 21G C11 N16 SING Y N 15 21G C13 C14 DOUB Y N 16 21G N16 C15 DOUB Y N 17 21G C15 C14 SING Y N 18 21G C15 N17 SING N N 19 21G C14 F31 SING N N 20 21G O30 C28 DOUB N N 21 21G N17 C18 SING N N 22 21G C18 C25 SING N N 23 21G C18 C20 SING N N 24 21G C28 O29 SING N N 25 21G C28 C20 SING N N 26 21G C24 C25 SING N N 27 21G C24 C23 SING N N 28 21G C25 C26 SING N N 29 21G C20 C22 SING N N 30 21G C23 C22 SING N N 31 21G C26 C27 SING N N 32 21G C22 C27 SING N N 33 21G C1 H1 SING N N 34 21G C3 H2 SING N N 35 21G C8 H3 SING N N 36 21G N9 H4 SING N N 37 21G C13 H5 SING N N 38 21G N17 H6 SING N N 39 21G C18 H7 SING N N 40 21G C20 H8 SING N N 41 21G C22 H9 SING N N 42 21G C23 H10 SING N N 43 21G C23 H11 SING N N 44 21G C24 H12 SING N N 45 21G C24 H13 SING N N 46 21G C25 H14 SING N N 47 21G C26 H15 SING N N 48 21G C26 H16 SING N N 49 21G C27 H17 SING N N 50 21G C27 H18 SING N N 51 21G O29 H19 SING N N 52 # # 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 21G SMILES ACDLabs 12.01 "O=C(O)C5C1CCC(CC1)C5Nc2nc(ncc2F)c4c3cc(F)cnc3nc4" 21G InChI InChI 1.03 "InChI=1S/C20H19F2N5O2/c21-11-5-12-13(7-24-17(12)23-6-11)18-25-8-14(22)19(27-18)26-16-10-3-1-9(2-4-10)15(16)20(28)29/h5-10,15-16H,1-4H2,(H,23,24)(H,28,29)(H,25,26,27)/t9-,10+,15-,16-/m0/s1" 21G InChIKey InChI 1.03 JGPXDNKSIXAZEQ-UIHHKEIPSA-N 21G SMILES_CANONICAL CACTVS 3.385 "OC(=O)[C@H]1C2CCC(CC2)[C@@H]1Nc3nc(ncc3F)c4c[nH]c5ncc(F)cc45" 21G SMILES CACTVS 3.385 "OC(=O)[CH]1C2CCC(CC2)[CH]1Nc3nc(ncc3F)c4c[nH]c5ncc(F)cc45" 21G SMILES_CANONICAL "OpenEye OEToolkits" 1.9.2 "c1c(cnc2c1c(c[nH]2)c3ncc(c(n3)N[C@@H]4[C@H](C5CCC4CC5)C(=O)O)F)F" 21G SMILES "OpenEye OEToolkits" 1.9.2 "c1c(cnc2c1c(c[nH]2)c3ncc(c(n3)NC4C5CCC(C4C(=O)O)CC5)F)F" # # 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 21G "SYSTEMATIC NAME" ACDLabs 12.01 "(1R,2S,3S,4R)-3-{[5-fluoro-2-(5-fluoro-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrimidin-4-yl]amino}bicyclo[2.2.2]octane-2-carboxylic acid" 21G "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.9.2 "(2S,3S)-3-[[5-fluoranyl-2-(5-fluoranyl-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrimidin-4-yl]amino]bicyclo[2.2.2]octane-2-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 21G "Create component" 2014-03-03 RCSB 21G "Initial release" 2014-07-30 RCSB 21G "Modify descriptor" 2014-09-05 RCSB 21G "Modify synonyms" 2020-11-26 PDBE # # loop_ _pdbx_chem_comp_synonyms.ordinal _pdbx_chem_comp_synonyms.comp_id _pdbx_chem_comp_synonyms.name _pdbx_chem_comp_synonyms.provenance _pdbx_chem_comp_synonyms.type 1 21G "3-[[5-fluoro-2-(5-fluoro-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrimidin-4-yl]amino]bicyclo[2.2.2]octane-2-carboxylic acid" PUBCHEM ? 2 21G VX787 PUBCHEM ? 3 21G 67976417 PUBCHEM ? 4 21G "(2S,3S)-3-((5-fluoro-2-(5-fluoro-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrimidin-4-yl)amino)bicyclo[2.2.2]octane-2-carboxylic acid" AUTHOR ? ##