data_73A # _chem_comp.id 73A _chem_comp.name "(2E)-3-[4-amino-5-(4-chlorophenyl)-7-(2-methoxyethyl)-7H-pyrrolo[2,3-d]pyrimidin-6-yl]-2-cyano-N-(propan-2-yl)prop-2-enamide" _chem_comp.type NON-POLYMER _chem_comp.pdbx_type HETAIN _chem_comp.formula "C22 H23 Cl N6 O2" _chem_comp.mon_nstd_parent_comp_id ? _chem_comp.pdbx_synonyms "Rao-IV-151, unbound form" _chem_comp.pdbx_formal_charge 0 _chem_comp.pdbx_initial_date 2016-08-18 _chem_comp.pdbx_modified_date 2021-03-13 _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 438.910 _chem_comp.one_letter_code ? _chem_comp.three_letter_code 73A _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 5T0P _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 73A C2 C1 C 0 1 Y N N -11.498 37.590 -5.832 -3.138 -0.522 -0.515 C2 73A 1 73A N1 N1 N 0 1 Y N N -13.012 35.620 -6.841 -3.916 -3.097 -0.881 N1 73A 2 73A N2 N2 N 0 1 Y N N -12.788 37.584 -5.470 -4.388 -0.832 -0.859 N2 73A 3 73A C3 C2 C 0 1 Y N N -10.878 36.663 -6.682 -2.211 -1.570 -0.348 C3 73A 4 73A O1 O1 O 0 1 N N N -11.250 40.702 -2.540 -4.300 3.648 0.942 O1 73A 5 73A C8 C3 C 0 1 Y N N -6.807 35.109 -9.410 2.724 -2.944 0.829 C8 73A 6 73A C7 C4 C 0 1 Y N N -7.684 36.044 -9.918 2.073 -2.261 1.843 C7 73A 7 73A C1 C5 C 0 1 Y N N -13.461 36.575 -6.025 -4.750 -2.085 -1.033 C1 73A 8 73A C17 C6 C 0 1 N N N -7.400 41.354 -1.350 3.852 4.893 -0.854 C17 73A 9 73A C4 C7 C 0 1 Y N N -9.503 37.077 -6.789 -0.940 -0.952 0.023 C4 73A 10 73A N3 N3 N 0 1 N N N -7.765 36.828 -2.879 1.223 0.100 -2.510 N3 73A 11 73A C5 C8 C 0 1 Y N N -8.494 36.463 -7.683 0.335 -1.645 0.303 C5 73A 12 73A C6 C9 C 0 1 Y N N -8.511 36.734 -9.050 0.883 -1.613 1.587 C6 73A 13 73A C9 C10 C 0 1 Y N N -6.763 34.825 -8.061 2.186 -2.980 -0.447 C9 73A 14 73A N4 N4 N 0 1 N N N -6.325 40.385 -3.325 3.115 2.565 -0.722 N4 73A 15 73A C11 C11 C 0 1 Y N N -9.362 38.143 -6.035 -1.171 0.424 0.058 C11 73A 16 73A C13 C12 C 0 1 N N N -7.429 38.679 -4.641 0.936 1.520 -0.390 C13 73A 17 73A C14 C13 C 0 1 N N N -7.631 37.639 -3.675 1.096 0.729 -1.572 C14 73A 18 73A C12 C14 C 0 1 N N N -8.236 38.891 -5.703 -0.219 1.406 0.372 C12 73A 19 73A O O2 O 0 1 N N N -5.350 39.645 -5.246 1.858 3.127 1.022 O 73A 20 73A C15 C15 C 0 1 N N N -6.277 39.611 -4.432 1.994 2.454 0.017 C15 73A 21 73A C16 C16 C 0 1 N N N -7.569 40.974 -2.807 4.170 3.497 -0.317 C16 73A 22 73A C18 C17 C 0 1 N N N -7.973 42.162 -3.654 5.512 3.026 -0.882 C18 73A 23 73A N5 N5 N 0 1 Y N N -10.558 38.525 -5.446 -2.494 0.659 -0.272 N5 73A 24 73A C19 C18 C 0 1 N N N -10.814 39.754 -4.674 -3.116 1.984 -0.349 C19 73A 25 73A C20 C19 C 0 1 N N N -11.399 39.513 -3.301 -3.694 2.356 1.017 C20 73A 26 73A C21 C20 C 0 1 N N N -12.249 41.696 -2.784 -4.874 4.093 2.173 C21 73A 27 73A C C21 C 0 1 Y N N -11.709 35.639 -7.198 -2.643 -2.893 -0.551 C 73A 28 73A N N6 N 0 1 N N N -11.276 34.700 -8.043 -1.775 -3.954 -0.394 N 73A 29 73A C10 C22 C 0 1 Y N N -7.605 35.507 -7.200 0.997 -2.335 -0.715 C10 73A 30 73A CL CL1 CL 0 0 N N N -5.682 34.324 -10.485 4.225 -3.753 1.156 CL 73A 31 73A H1 H1 H 0 1 N N N -7.725 36.235 -10.980 2.497 -2.237 2.835 H1 73A 32 73A H2 H2 H 0 1 N N N -14.512 36.524 -5.781 -5.774 -2.295 -1.301 H2 73A 33 73A H3 H3 H 0 1 N N N -7.107 40.466 -0.771 3.796 4.860 -1.942 H3 73A 34 73A H4 H4 H 0 1 N N N -6.620 42.124 -1.260 2.897 5.229 -0.451 H4 73A 35 73A H5 H5 H 0 1 N N N -8.351 41.748 -0.961 4.637 5.587 -0.552 H5 73A 36 73A H6 H6 H 0 1 N N N -9.177 37.491 -9.436 0.376 -1.081 2.379 H6 73A 37 73A H7 H7 H 0 1 N N N -6.080 34.080 -7.681 2.698 -3.514 -1.234 H7 73A 38 73A H8 H8 H 0 1 N N N -5.473 40.566 -2.834 3.223 2.029 -1.523 H8 73A 39 73A H9 H9 H 0 1 N N N -7.985 39.716 -6.354 -0.385 2.072 1.206 H9 73A 40 73A H10 H10 H 0 1 N N N -8.368 40.221 -2.872 4.226 3.531 0.771 H10 73A 41 73A H11 H11 H 0 1 N N N -8.904 42.595 -3.259 5.455 2.992 -1.970 H11 73A 42 73A H12 H12 H 0 1 N N N -7.176 42.919 -3.627 6.297 3.719 -0.580 H12 73A 43 73A H13 H13 H 0 1 N N N -8.133 41.835 -4.692 5.738 2.031 -0.499 H13 73A 44 73A H14 H14 H 0 1 N N N -9.861 40.291 -4.554 -2.367 2.720 -0.640 H14 73A 45 73A H15 H15 H 0 1 N N N -11.517 40.379 -5.244 -3.916 1.967 -1.090 H15 73A 46 73A H16 H16 H 0 1 N N N -12.466 39.259 -3.390 -2.894 2.373 1.758 H16 73A 47 73A H17 H17 H 0 1 N N N -10.865 38.687 -2.809 -4.443 1.620 1.308 H17 73A 48 73A H18 H18 H 0 1 N N N -12.053 42.576 -2.154 -5.313 5.081 2.033 H18 73A 49 73A H19 H19 H 0 1 N N N -12.222 41.991 -3.843 -5.647 3.393 2.488 H19 73A 50 73A H20 H20 H 0 1 N N N -13.241 41.286 -2.543 -4.098 4.146 2.937 H20 73A 51 73A H21 H21 H 0 1 N N N -12.035 34.097 -8.290 -2.089 -4.862 -0.523 H21 73A 52 73A H22 H22 H 0 1 N N N -10.914 35.135 -8.868 -0.849 -3.791 -0.153 H22 73A 53 73A H23 H23 H 0 1 N N N -7.572 35.295 -6.142 0.578 -2.364 -1.710 H23 73A 54 # # 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 73A CL C8 SING N N 1 73A C7 C8 DOUB Y N 2 73A C7 C6 SING Y N 3 73A C8 C9 SING Y N 4 73A C6 C5 DOUB Y N 5 73A C9 C10 DOUB Y N 6 73A N C SING N N 7 73A C5 C10 SING Y N 8 73A C5 C4 SING N N 9 73A C N1 DOUB Y N 10 73A C C3 SING Y N 11 73A N1 C1 SING Y N 12 73A C4 C3 SING Y N 13 73A C4 C11 DOUB Y N 14 73A C3 C2 DOUB Y N 15 73A C11 C12 SING N N 16 73A C11 N5 SING Y N 17 73A C1 N2 DOUB Y N 18 73A C2 N2 SING Y N 19 73A C2 N5 SING Y N 20 73A C12 C13 DOUB N E 21 73A N5 C19 SING N N 22 73A O C15 DOUB N N 23 73A C19 C20 SING N N 24 73A C13 C15 SING N N 25 73A C13 C14 SING N N 26 73A C15 N4 SING N N 27 73A C14 N3 TRIP N N 28 73A C18 C16 SING N N 29 73A N4 C16 SING N N 30 73A C20 O1 SING N N 31 73A C16 C17 SING N N 32 73A C21 O1 SING N N 33 73A C7 H1 SING N N 34 73A C1 H2 SING N N 35 73A C17 H3 SING N N 36 73A C17 H4 SING N N 37 73A C17 H5 SING N N 38 73A C6 H6 SING N N 39 73A C9 H7 SING N N 40 73A N4 H8 SING N N 41 73A C12 H9 SING N N 42 73A C16 H10 SING N N 43 73A C18 H11 SING N N 44 73A C18 H12 SING N N 45 73A C18 H13 SING N N 46 73A C19 H14 SING N N 47 73A C19 H15 SING N N 48 73A C20 H16 SING N N 49 73A C20 H17 SING N N 50 73A C21 H18 SING N N 51 73A C21 H19 SING N N 52 73A C21 H20 SING N N 53 73A N H21 SING N N 54 73A N H22 SING N N 55 73A C10 H23 SING N N 56 # # 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 73A SMILES ACDLabs 12.01 "c21ncnc(c1c(c(/C=C(/C(NC(C)C)=O)C#N)n2CCOC)c3ccc(cc3)Cl)N" 73A InChI InChI 1.03 "InChI=1S/C22H23ClN6O2/c1-13(2)28-22(30)15(11-24)10-17-18(14-4-6-16(23)7-5-14)19-20(25)26-12-27-21(19)29(17)8-9-31-3/h4-7,10,12-13H,8-9H2,1-3H3,(H,28,30)(H2,25,26,27)/b15-10+" 73A InChIKey InChI 1.03 VJGVUTLADNGMJV-XNTDXEJSSA-N 73A SMILES_CANONICAL CACTVS 3.385 "COCCn1c(\C=C(/C#N)C(=O)NC(C)C)c(c2ccc(Cl)cc2)c3c(N)ncnc13" 73A SMILES CACTVS 3.385 "COCCn1c(C=C(C#N)C(=O)NC(C)C)c(c2ccc(Cl)cc2)c3c(N)ncnc13" 73A SMILES_CANONICAL "OpenEye OEToolkits" 2.0.5 "CC(C)NC(=O)/C(=C/c1c(c2c(ncnc2n1CCOC)N)c3ccc(cc3)Cl)/C#N" 73A SMILES "OpenEye OEToolkits" 2.0.5 "CC(C)NC(=O)C(=Cc1c(c2c(ncnc2n1CCOC)N)c3ccc(cc3)Cl)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 73A "SYSTEMATIC NAME" ACDLabs 12.01 "(2E)-3-[4-amino-5-(4-chlorophenyl)-7-(2-methoxyethyl)-7H-pyrrolo[2,3-d]pyrimidin-6-yl]-2-cyano-N-(propan-2-yl)prop-2-enamide" 73A "SYSTEMATIC NAME" "OpenEye OEToolkits" 2.0.5 "(~{E})-3-[4-azanyl-5-(4-chlorophenyl)-7-(2-methoxyethyl)pyrrolo[2,3-d]pyrimidin-6-yl]-2-cyano-~{N}-propan-2-yl-prop-2-enamide" # # loop_ _pdbx_chem_comp_audit.comp_id _pdbx_chem_comp_audit.action_type _pdbx_chem_comp_audit.date _pdbx_chem_comp_audit.processing_site 73A "Create component" 2016-08-18 RCSB 73A "Initial release" 2017-08-23 RCSB 73A "Modify synonyms" 2021-03-13 RCSB # _pdbx_chem_comp_synonyms.ordinal 1 _pdbx_chem_comp_synonyms.comp_id 73A _pdbx_chem_comp_synonyms.name "Rao-IV-151, unbound form" _pdbx_chem_comp_synonyms.provenance PDB _pdbx_chem_comp_synonyms.type ? ##