data_HRA # _chem_comp.id HRA _chem_comp.name "1,5-anhydro-2-{[5-(2-chloro-4-phenoxybenzene-1-carbonyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl]amino}-2,3,4-trideoxy-D-erythro-hexitol" _chem_comp.type NON-POLYMER _chem_comp.pdbx_type HETAIN _chem_comp.formula "C25 H23 Cl N4 O4" _chem_comp.mon_nstd_parent_comp_id ? _chem_comp.pdbx_synonyms ? _chem_comp.pdbx_formal_charge 0 _chem_comp.pdbx_initial_date 2018-07-18 _chem_comp.pdbx_modified_date 2018-08-31 _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 478.928 _chem_comp.one_letter_code ? _chem_comp.three_letter_code HRA _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 6E4F _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 HRA C1 C1 C 0 1 N N N 23.888 6.516 1.563 -3.113 -1.509 1.458 C1 HRA 1 HRA C2 C2 C 0 1 N N N 25.024 7.012 0.692 -4.000 -2.755 1.381 C2 HRA 2 HRA C3 C3 C 0 1 N N S 24.721 8.283 0.091 -3.572 -3.603 0.180 C3 HRA 3 HRA C4 C4 C 0 1 N N N 22.306 7.853 0.079 -2.817 -1.665 -1.015 C4 HRA 4 HRA C5 C5 C 0 1 Y N N 19.294 7.040 6.655 1.278 0.981 -0.465 C5 HRA 5 HRA C6 C6 C 0 1 Y N N 18.819 7.110 7.971 2.127 -0.036 -0.840 C6 HRA 6 HRA C7 C7 C 0 1 Y N N 18.425 5.923 8.569 2.678 -0.876 0.122 C7 HRA 7 HRA C9 C8 C 0 1 Y N N 18.991 4.679 6.613 1.535 0.329 1.852 C9 HRA 8 HRA C10 C9 C 0 1 Y N N 19.383 5.854 5.943 0.974 1.173 0.886 C10 HRA 9 HRA C11 C10 C 0 1 N N N 19.848 5.905 4.583 0.075 2.269 1.294 C11 HRA 10 HRA C12 C11 C 0 1 Y N N 17.698 5.090 3.673 -0.301 4.344 -0.115 C12 HRA 11 HRA C13 C12 C 0 1 Y N N 19.011 5.488 3.473 -0.613 3.072 0.274 C13 HRA 12 HRA C14 C13 C 0 1 Y N N 20.301 5.625 1.197 -2.566 1.516 -0.625 C14 HRA 13 HRA C16 C14 C 0 1 Y N N 18.092 4.885 1.519 -2.072 3.761 -1.362 C16 HRA 14 HRA C C15 C 0 1 N N N 25.935 8.511 -0.859 -4.492 -4.819 0.060 C HRA 15 HRA O O1 O 0 1 N N N 25.631 9.648 -1.536 -4.023 -5.670 -0.988 O HRA 16 HRA O1 O2 O 0 1 N N N 23.439 8.293 -0.645 -3.661 -2.819 -1.011 O1 HRA 17 HRA C18 C16 C 0 1 N N R 22.588 6.486 0.725 -3.213 -0.739 0.138 C18 HRA 18 HRA N3 N1 N 0 1 N N N 21.497 6.118 1.583 -2.310 0.414 0.171 N3 HRA 19 HRA C15 C17 C 0 1 Y N N 19.259 5.378 2.090 -1.775 2.668 -0.533 C15 HRA 20 HRA N1 N2 N 0 1 Y N N 20.174 5.366 -0.126 -3.569 1.508 -1.499 N1 HRA 21 HRA C17 C18 C 0 1 Y N N 18.988 4.833 -0.537 -3.815 2.558 -2.261 C17 HRA 22 HRA N2 N3 N 0 1 Y N N 17.922 4.603 0.211 -3.098 3.659 -2.205 N2 HRA 23 HRA N N4 N 0 1 Y N N 17.151 4.767 2.487 -1.168 4.752 -1.077 N HRA 24 HRA O3 O3 O 0 1 N N N 20.965 6.406 4.337 -0.098 2.508 2.475 O3 HRA 25 HRA CL CL1 CL 0 0 N N N 19.111 3.136 5.866 1.155 0.556 3.530 CL HRA 26 HRA C8 C19 C 0 1 Y N N 18.547 4.722 7.904 2.375 -0.693 1.466 C8 HRA 27 HRA O2 O4 O 0 1 N N N 17.954 5.932 9.843 3.515 -1.876 -0.252 O2 HRA 28 HRA C19 C20 C 0 1 Y N N 16.949 6.798 10.188 4.759 -1.540 -0.683 C19 HRA 29 HRA C24 C21 C 0 1 Y N N 16.968 7.281 11.516 5.178 -0.218 -0.634 C24 HRA 30 HRA C23 C22 C 0 1 Y N N 15.968 8.174 11.966 6.443 0.121 -1.073 C23 HRA 31 HRA C22 C23 C 0 1 Y N N 14.925 8.552 11.058 7.292 -0.856 -1.560 C22 HRA 32 HRA C21 C24 C 0 1 Y N N 14.911 8.076 9.748 6.877 -2.174 -1.611 C21 HRA 33 HRA C20 C25 C 0 1 Y N N 15.944 7.190 9.294 5.615 -2.519 -1.168 C20 HRA 34 HRA H1 H1 H 0 1 N N N 24.116 5.503 1.926 -3.448 -0.873 2.278 H1 HRA 35 HRA H2 H2 H 0 1 N N N 23.758 7.192 2.421 -2.078 -1.808 1.629 H2 HRA 36 HRA H3 H3 H 0 1 N N N 25.209 6.277 -0.105 -3.891 -3.338 2.295 H3 HRA 37 HRA H4 H4 H 0 1 N N N 25.927 7.117 1.311 -5.041 -2.454 1.263 H4 HRA 38 HRA H5 H5 H 0 1 N N N 24.717 9.075 0.854 -2.544 -3.937 0.319 H5 HRA 39 HRA H6 H6 H 0 1 N N N 22.070 8.585 0.865 -1.780 -1.977 -0.891 H6 HRA 40 HRA H7 H7 H 0 1 N N N 21.450 7.762 -0.606 -2.927 -1.135 -1.961 H7 HRA 41 HRA H8 H8 H 0 1 N N N 19.606 7.954 6.172 0.851 1.632 -1.213 H8 HRA 42 HRA H9 H9 H 0 1 N N N 18.762 8.051 8.498 2.366 -0.182 -1.883 H9 HRA 43 HRA H10 H10 H 0 1 N N N 17.195 5.046 4.628 0.508 4.936 0.286 H10 HRA 44 HRA H11 H11 H 0 1 N N N 26.050 7.665 -1.553 -4.493 -5.369 1.001 H11 HRA 45 HRA H12 H12 H 0 1 N N N 26.862 8.639 -0.281 -5.505 -4.488 -0.168 H12 HRA 46 HRA H13 H13 H 0 1 N N N 26.333 9.854 -2.142 -4.560 -6.464 -1.121 H13 HRA 47 HRA H14 H14 H 0 1 N N N 22.706 5.739 -0.074 -4.238 -0.397 -0.005 H14 HRA 48 HRA H15 H15 H 0 1 N N N 21.874 5.429 2.202 -1.533 0.405 0.752 H15 HRA 49 HRA H16 H16 H 0 1 N N N 18.911 4.572 -1.582 -4.639 2.511 -2.957 H16 HRA 50 HRA H17 H17 H 0 1 N N N 16.202 4.485 2.343 -1.145 5.621 -1.507 H17 HRA 51 HRA H18 H18 H 0 1 N N N 18.288 3.804 8.410 2.808 -1.345 2.210 H18 HRA 52 HRA H19 H19 H 0 1 N N N 17.750 6.966 12.191 4.515 0.545 -0.254 H19 HRA 53 HRA H20 H20 H 0 1 N N N 15.990 8.563 12.973 6.769 1.150 -1.035 H20 HRA 54 HRA H21 H21 H 0 1 N N N 14.140 9.214 11.393 8.281 -0.589 -1.903 H21 HRA 55 HRA H22 H22 H 0 1 N N N 14.122 8.374 9.074 7.542 -2.934 -1.992 H22 HRA 56 HRA H23 H23 H 0 1 N N N 15.947 6.830 8.276 5.291 -3.549 -1.207 H23 HRA 57 # 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 HRA O C SING N N 1 HRA C C3 SING N N 2 HRA O1 C4 SING N N 3 HRA O1 C3 SING N N 4 HRA C17 N1 DOUB Y N 5 HRA C17 N2 SING Y N 6 HRA N1 C14 SING Y N 7 HRA C4 C18 SING N N 8 HRA C3 C2 SING N N 9 HRA N2 C16 DOUB Y N 10 HRA C2 C1 SING N N 11 HRA C18 C1 SING N N 12 HRA C18 N3 SING N N 13 HRA C14 N3 SING N N 14 HRA C14 C15 DOUB Y N 15 HRA C16 C15 SING Y N 16 HRA C16 N SING Y N 17 HRA C15 C13 SING Y N 18 HRA N C12 SING Y N 19 HRA C13 C12 DOUB Y N 20 HRA C13 C11 SING N N 21 HRA O3 C11 DOUB N N 22 HRA C11 C10 SING N N 23 HRA CL C9 SING N N 24 HRA C10 C9 DOUB Y N 25 HRA C10 C5 SING Y N 26 HRA C9 C8 SING Y N 27 HRA C5 C6 DOUB Y N 28 HRA C8 C7 DOUB Y N 29 HRA C6 C7 SING Y N 30 HRA C7 O2 SING N N 31 HRA C20 C21 DOUB Y N 32 HRA C20 C19 SING Y N 33 HRA C21 C22 SING Y N 34 HRA O2 C19 SING N N 35 HRA C19 C24 DOUB Y N 36 HRA C22 C23 DOUB Y N 37 HRA C24 C23 SING Y N 38 HRA C1 H1 SING N N 39 HRA C1 H2 SING N N 40 HRA C2 H3 SING N N 41 HRA C2 H4 SING N N 42 HRA C3 H5 SING N N 43 HRA C4 H6 SING N N 44 HRA C4 H7 SING N N 45 HRA C5 H8 SING N N 46 HRA C6 H9 SING N N 47 HRA C12 H10 SING N N 48 HRA C H11 SING N N 49 HRA C H12 SING N N 50 HRA O H13 SING N N 51 HRA C18 H14 SING N N 52 HRA N3 H15 SING N N 53 HRA C17 H16 SING N N 54 HRA N H17 SING N N 55 HRA C8 H18 SING N N 56 HRA C24 H19 SING N N 57 HRA C23 H20 SING N N 58 HRA C22 H21 SING N N 59 HRA C21 H22 SING N N 60 HRA C20 H23 SING N N 61 # 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 HRA SMILES ACDLabs 12.01 "C1CC(CO)OCC1Nc5c4c(C(c3ccc(Oc2ccccc2)cc3Cl)=O)cnc4ncn5" HRA InChI InChI 1.03 "InChI=1S/C25H23ClN4O4/c26-21-10-17(34-16-4-2-1-3-5-16)8-9-19(21)23(32)20-11-27-24-22(20)25(29-14-28-24)30-15-6-7-18(12-31)33-13-15/h1-5,8-11,14-15,18,31H,6-7,12-13H2,(H2,27,28,29,30)/t15-,18+/m1/s1" HRA InChIKey InChI 1.03 JSFCZQSJQXFJDS-QAPCUYQASA-N HRA SMILES_CANONICAL CACTVS 3.385 "OC[C@@H]1CC[C@H](CO1)Nc2ncnc3[nH]cc(C(=O)c4ccc(Oc5ccccc5)cc4Cl)c23" HRA SMILES CACTVS 3.385 "OC[CH]1CC[CH](CO1)Nc2ncnc3[nH]cc(C(=O)c4ccc(Oc5ccccc5)cc4Cl)c23" HRA SMILES_CANONICAL "OpenEye OEToolkits" 2.0.6 "c1ccc(cc1)Oc2ccc(c(c2)Cl)C(=O)c3c[nH]c4c3c(ncn4)N[C@@H]5CC[C@H](OC5)CO" HRA SMILES "OpenEye OEToolkits" 2.0.6 "c1ccc(cc1)Oc2ccc(c(c2)Cl)C(=O)c3c[nH]c4c3c(ncn4)NC5CCC(OC5)CO" # 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 HRA "SYSTEMATIC NAME" ACDLabs 12.01 "1,5-anhydro-2-{[5-(2-chloro-4-phenoxybenzene-1-carbonyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl]amino}-2,3,4-trideoxy-D-erythro-hexitol" HRA "SYSTEMATIC NAME" "OpenEye OEToolkits" 2.0.6 "(2-chloranyl-4-phenoxy-phenyl)-[4-[[(3~{R},6~{S})-6-(hydroxymethyl)oxan-3-yl]amino]-7~{H}-pyrrolo[2,3-d]pyrimidin-5-yl]methanone" # loop_ _pdbx_chem_comp_audit.comp_id _pdbx_chem_comp_audit.action_type _pdbx_chem_comp_audit.date _pdbx_chem_comp_audit.processing_site HRA "Create component" 2018-07-18 RCSB HRA "Initial release" 2018-09-05 RCSB #