data_71D # _chem_comp.id 71D _chem_comp.name ;(2R)-3-[4-amino-5-(4-chlorophenyl)-7-(2-methoxyethyl)-7H-pyrrolo[2,3-d]pyrimidin-6-yl]-2-cyano-N-(propan-2-yl)propanami de ; _chem_comp.type NON-POLYMER _chem_comp.pdbx_type HETAIN _chem_comp.formula "C22 H25 Cl N6 O2" _chem_comp.mon_nstd_parent_comp_id ? _chem_comp.pdbx_synonyms "Rao-IV-151, bound form" _chem_comp.pdbx_formal_charge 0 _chem_comp.pdbx_initial_date 2016-08-10 _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 440.926 _chem_comp.one_letter_code ? _chem_comp.three_letter_code 71D _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 5SWH _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 71D C1 C1 C 0 1 Y N N -12.389 -35.572 5.870 3.802 3.312 1.337 C1 71D 1 71D C2 C2 C 0 1 Y N N -10.504 -36.756 5.929 1.812 2.445 0.569 C2 71D 2 71D C3 C3 C 0 1 Y N N -9.898 -35.836 6.793 2.425 1.184 0.474 C3 71D 3 71D C4 C4 C 0 1 Y N N -8.652 -36.421 7.187 1.390 0.262 -0.013 C4 71D 4 71D C5 C5 C 0 1 Y N N -7.688 -35.751 8.085 1.547 -1.189 -0.276 C5 71D 5 71D C6 C6 C 0 1 Y N N -6.727 -34.886 7.582 1.429 -1.681 -1.575 C6 71D 6 71D C13 C7 C 0 1 N N R -6.093 -38.309 6.314 -1.947 0.133 0.542 C13 71D 7 71D C14 C8 C 0 1 N N N -6.109 -37.465 5.114 -1.352 -0.982 1.297 C14 71D 8 71D C15 C9 C 0 1 N N N -5.147 -39.493 6.084 -3.319 -0.263 0.060 C15 71D 9 71D C16 C10 C 0 1 N N N -2.925 -40.318 6.829 -5.607 -0.987 0.479 C16 71D 10 71D C17 C11 C 0 1 N N N -1.557 -39.722 7.126 -5.614 -2.476 0.127 C17 71D 11 71D C18 C12 C 0 1 N N N -2.839 -41.436 5.809 -6.633 -0.719 1.582 C18 71D 12 71D C19 C13 C 0 1 N N N -9.433 -38.269 4.274 -0.476 3.381 0.123 C19 71D 13 71D C20 C14 C 0 1 N N N -9.844 -39.725 4.203 -0.386 4.093 -1.229 C20 71D 14 71D O O1 O 0 1 N N N -5.568 -40.568 5.654 -3.563 -0.278 -1.128 O 71D 15 71D N4 N1 N 0 1 N N N -3.853 -39.272 6.372 -4.274 -0.602 0.948 N4 71D 16 71D N3 N2 N 0 1 N N N -6.163 -36.825 4.174 -0.892 -1.842 1.880 N3 71D 17 71D C12 C15 C 0 1 N N N -7.533 -38.760 6.689 -1.060 0.466 -0.659 C12 71D 18 71D C11 C16 C 0 1 Y N N -8.576 -37.646 6.574 0.263 0.999 -0.174 C11 71D 19 71D N5 N3 N 0 1 Y N N -9.593 -37.769 5.650 0.511 2.299 0.171 N5 71D 20 71D O1 O2 O 0 1 N N N -8.966 -40.418 3.304 -1.367 5.130 -1.286 O1 71D 21 71D C21 C17 C 0 1 N N N -9.481 -41.685 2.875 -1.368 5.861 -2.514 C21 71D 22 71D N2 N4 N 0 1 Y N N -11.754 -36.667 5.445 2.538 3.473 1.009 N2 71D 23 71D N1 N5 N 0 1 Y N N -11.937 -34.601 6.668 4.418 2.146 1.252 N1 71D 24 71D C C18 C 0 1 Y N N -10.680 -34.705 7.147 3.775 1.061 0.829 C 71D 25 71D N N6 N 0 1 N N N -10.238 -33.729 7.939 4.421 -0.160 0.752 N 71D 26 71D C10 C19 C 0 1 Y N N -7.770 -35.934 9.460 1.819 -2.064 0.774 C10 71D 27 71D C9 C20 C 0 1 Y N N -6.921 -35.260 10.317 1.964 -3.413 0.524 C9 71D 28 71D C8 C21 C 0 1 Y N N -5.981 -34.408 9.794 1.840 -3.898 -0.767 C8 71D 29 71D CL CL1 CL 0 0 N N N -4.899 -33.576 10.872 2.024 -5.596 -1.074 CL 71D 30 71D C7 C22 C 0 1 Y N N -5.871 -34.210 8.435 1.576 -3.032 -1.814 C7 71D 31 71D H1 H1 H 0 1 N N N -13.405 -35.456 5.522 4.360 4.168 1.685 H1 71D 32 71D H2 H2 H 0 1 N N N -6.646 -34.739 6.515 1.222 -1.006 -2.392 H2 71D 33 71D H3 H3 H 0 1 N N N -5.699 -37.720 7.155 -2.028 1.007 1.188 H3 71D 34 71D H4 H4 H 0 1 N N N -3.316 -40.745 7.765 -5.864 -0.403 -0.405 H4 71D 35 71D H5 H5 H 0 1 N N N -1.661 -38.917 7.868 -6.606 -2.762 -0.222 H5 71D 36 71D H6 H6 H 0 1 N N N -0.895 -40.505 7.525 -4.883 -2.666 -0.659 H6 71D 37 71D H7 H7 H 0 1 N N N -1.126 -39.314 6.200 -5.357 -3.059 1.011 H7 71D 38 71D H8 H8 H 0 1 N N N -2.142 -42.207 6.168 -6.377 -1.303 2.466 H8 71D 39 71D H9 H9 H 0 1 N N N -3.835 -41.880 5.667 -6.629 0.342 1.833 H9 71D 40 71D H10 H10 H 0 1 N N N -2.478 -41.032 4.852 -7.625 -1.006 1.233 H10 71D 41 71D H11 H11 H 0 1 N N N -8.380 -38.172 3.971 -0.274 4.093 0.923 H11 71D 42 71D H12 H12 H 0 1 N N N -10.066 -37.678 3.595 -1.476 2.966 0.249 H12 71D 43 71D H13 H13 H 0 1 N N N -10.879 -39.798 3.837 0.607 4.525 -1.346 H13 71D 44 71D H14 H14 H 0 1 N N N -9.777 -40.176 5.204 -0.568 3.376 -2.030 H14 71D 45 71D H15 H15 H 0 1 N N N -3.500 -38.342 6.270 -4.079 -0.590 1.898 H15 71D 46 71D H16 H16 H 0 1 N N N -7.826 -39.581 6.018 -0.895 -0.435 -1.250 H16 71D 47 71D H17 H17 H 0 1 N N N -7.524 -39.122 7.728 -1.551 1.219 -1.276 H17 71D 48 71D H18 H18 H 0 1 N N N -8.763 -42.161 2.191 -0.395 6.330 -2.659 H18 71D 49 71D H19 H19 H 0 1 N N N -9.638 -42.332 3.750 -1.570 5.181 -3.342 H19 71D 50 71D H20 H20 H 0 1 N N N -10.438 -41.534 2.354 -2.140 6.630 -2.479 H20 71D 51 71D H21 H21 H 0 1 N N N -10.955 -33.041 8.053 3.938 -0.945 0.449 H21 71D 52 71D H22 H22 H 0 1 N N N -9.995 -34.108 8.832 5.356 -0.231 1.000 H22 71D 53 71D H23 H23 H 0 1 N N N -8.507 -36.612 9.864 1.916 -1.687 1.782 H23 71D 54 71D H24 H24 H 0 1 N N N -6.996 -35.402 11.385 2.175 -4.093 1.337 H24 71D 55 71D H25 H25 H 0 1 N N N -5.126 -33.535 8.040 1.484 -3.414 -2.820 H25 71D 56 # # 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 71D C21 O1 SING N N 1 71D O1 C20 SING N N 2 71D N3 C14 TRIP N N 3 71D C20 C19 SING N N 4 71D C19 N5 SING N N 5 71D C14 C13 SING N N 6 71D N2 C1 DOUB Y N 7 71D N2 C2 SING Y N 8 71D N5 C2 SING Y N 9 71D N5 C11 SING Y N 10 71D O C15 DOUB N N 11 71D C18 C16 SING N N 12 71D C1 N1 SING Y N 13 71D C2 C3 DOUB Y N 14 71D C15 C13 SING N N 15 71D C15 N4 SING N N 16 71D C13 C12 SING N N 17 71D N4 C16 SING N N 18 71D C11 C12 SING N N 19 71D C11 C4 DOUB Y N 20 71D N1 C DOUB Y N 21 71D C3 C SING Y N 22 71D C3 C4 SING Y N 23 71D C16 C17 SING N N 24 71D C N SING N N 25 71D C4 C5 SING N N 26 71D C6 C5 DOUB Y N 27 71D C6 C7 SING Y N 28 71D C5 C10 SING Y N 29 71D C7 C8 DOUB Y N 30 71D C10 C9 DOUB Y N 31 71D C8 C9 SING Y N 32 71D C8 CL SING N N 33 71D C1 H1 SING N N 34 71D C6 H2 SING N N 35 71D C13 H3 SING N N 36 71D C16 H4 SING N N 37 71D C17 H5 SING N N 38 71D C17 H6 SING N N 39 71D C17 H7 SING N N 40 71D C18 H8 SING N N 41 71D C18 H9 SING N N 42 71D C18 H10 SING N N 43 71D C19 H11 SING N N 44 71D C19 H12 SING N N 45 71D C20 H13 SING N N 46 71D C20 H14 SING N N 47 71D N4 H15 SING N N 48 71D C12 H16 SING N N 49 71D C12 H17 SING N N 50 71D C21 H18 SING N N 51 71D C21 H19 SING N N 52 71D C21 H20 SING N N 53 71D N H21 SING N N 54 71D N H22 SING N N 55 71D C10 H23 SING N N 56 71D C9 H24 SING N N 57 71D C7 H25 SING N N 58 # # 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 71D SMILES ACDLabs 12.01 "c3nc(c1c(n(CCOC)c(c1c2ccc(Cl)cc2)CC(C#N)C(NC(C)C)=O)n3)N" 71D InChI InChI 1.03 "InChI=1S/C22H25ClN6O2/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/h4-7,12-13,15H,8-10H2,1-3H3,(H,28,30)(H2,25,26,27)/t15-/m1/s1" 71D InChIKey InChI 1.03 GWOKLTYKEJQNOY-OAHLLOKOSA-N 71D SMILES_CANONICAL CACTVS 3.385 "COCCn1c(C[C@H](C#N)C(=O)NC(C)C)c(c2ccc(Cl)cc2)c3c(N)ncnc13" 71D SMILES CACTVS 3.385 "COCCn1c(C[CH](C#N)C(=O)NC(C)C)c(c2ccc(Cl)cc2)c3c(N)ncnc13" 71D SMILES_CANONICAL "OpenEye OEToolkits" 2.0.5 "CC(C)NC(=O)[C@H](Cc1c(c2c(ncnc2n1CCOC)N)c3ccc(cc3)Cl)C#N" 71D 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 71D "SYSTEMATIC NAME" ACDLabs 12.01 "(2R)-3-[4-amino-5-(4-chlorophenyl)-7-(2-methoxyethyl)-7H-pyrrolo[2,3-d]pyrimidin-6-yl]-2-cyano-N-(propan-2-yl)propanamide" 71D "SYSTEMATIC NAME" "OpenEye OEToolkits" 2.0.5 "(2~{R})-3-[4-azanyl-5-(4-chlorophenyl)-7-(2-methoxyethyl)pyrrolo[2,3-d]pyrimidin-6-yl]-2-cyano-~{N}-propan-2-yl-propanamide" # # loop_ _pdbx_chem_comp_audit.comp_id _pdbx_chem_comp_audit.action_type _pdbx_chem_comp_audit.date _pdbx_chem_comp_audit.processing_site 71D "Create component" 2016-08-10 RCSB 71D "Modify synonyms" 2016-08-18 RCSB 71D "Initial release" 2017-08-16 RCSB 71D "Modify synonyms" 2020-06-05 PDBE # _pdbx_chem_comp_synonyms.ordinal 1 _pdbx_chem_comp_synonyms.comp_id 71D _pdbx_chem_comp_synonyms.name "Rao-IV-151, bound form" _pdbx_chem_comp_synonyms.provenance ? _pdbx_chem_comp_synonyms.type ? ##