data_14S # _chem_comp.id 14S _chem_comp.name "4-(cyclopentylamino)-2-[(2-methoxybenzyl)amino]-N-[3-(2-oxopyrrolidin-1-yl)propyl]pyrimidine-5-carboxamide" _chem_comp.type NON-POLYMER _chem_comp.pdbx_type HETAIN _chem_comp.formula "C25 H34 N6 O3" _chem_comp.mon_nstd_parent_comp_id ? _chem_comp.pdbx_synonyms ? _chem_comp.pdbx_formal_charge 0 _chem_comp.pdbx_initial_date 2012-10-09 _chem_comp.pdbx_modified_date 2013-03-08 _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 466.576 _chem_comp.one_letter_code ? _chem_comp.three_letter_code 14S _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 4FF8 _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 14S O33 O33 O 0 1 N N N 35.869 9.190 20.329 -7.642 1.423 -2.106 O33 14S 1 14S C28 C28 C 0 1 N N N 34.798 9.600 20.755 -7.944 1.666 -0.956 C28 14S 2 14S C32 C32 C 0 1 N N N 34.499 9.759 22.226 -8.887 2.766 -0.522 C32 14S 3 14S C34 C34 C 0 1 N N N 33.016 10.207 22.240 -8.610 2.927 0.991 C34 14S 4 14S C29 C29 C 0 1 N N N 32.620 10.544 20.779 -8.055 1.534 1.360 C29 14S 5 14S N24 N24 N 0 1 N N N 33.742 9.976 20.035 -7.494 0.993 0.116 N24 14S 6 14S C21 C21 C 0 1 N N N 33.608 9.854 18.583 -6.560 -0.134 0.053 C21 14S 7 14S C19 C19 C 0 1 N N N 34.311 11.075 17.990 -5.124 0.387 0.139 C19 14S 8 14S C15 C15 C 0 1 N N N 34.732 10.858 16.540 -4.149 -0.790 0.073 C15 14S 9 14S N10 N10 N 0 1 N N N 34.887 12.114 15.829 -2.774 -0.290 0.156 N10 14S 10 14S C6 C6 C 0 1 N N N 33.864 12.813 15.338 -1.740 -1.153 0.117 C6 14S 11 14S O11 O11 O 0 1 N N N 32.712 12.443 15.466 -1.948 -2.347 0.013 O11 14S 12 14S C2 C2 C 0 1 Y N N 34.140 14.103 14.622 -0.359 -0.651 0.200 C2 14S 13 14S C1 C1 C 0 1 Y N N 33.197 15.125 14.537 0.734 -1.543 0.273 C1 14S 14 14S N4 N4 N 0 1 N N N 31.977 14.972 15.113 0.529 -2.906 0.269 N4 14S 15 14S C8 C8 C 0 1 N N N 30.914 15.969 15.074 1.659 -3.817 0.464 C8 14S 16 14S C14 C14 C 0 1 N N N 31.080 17.028 16.155 2.325 -4.132 -0.891 C14 14S 17 14S C18 C18 C 0 1 N N N 29.959 16.879 17.173 2.730 -5.623 -0.778 C18 14S 18 14S C17 C17 C 0 1 N N N 29.113 15.688 16.748 1.544 -6.241 0.002 C17 14S 19 14S C13 C13 C 0 1 N N N 29.578 15.285 15.351 1.163 -5.159 1.032 C13 14S 20 14S C5 C5 C 0 1 Y N N 35.377 14.289 14.027 -0.092 0.722 0.202 C5 14S 21 14S N9 N9 N 0 1 Y N N 35.654 15.428 13.390 1.160 1.132 0.278 N9 14S 22 14S C7 C7 C 0 1 Y N N 34.745 16.417 13.305 2.163 0.266 0.351 C7 14S 23 14S N3 N3 N 0 1 Y N N 33.526 16.267 13.877 1.962 -1.044 0.346 N3 14S 24 14S N12 N12 N 0 1 N N N 35.086 17.551 12.651 3.455 0.743 0.427 N12 14S 25 14S C16 C16 C 0 1 N N N 34.142 18.645 12.511 3.703 2.187 0.427 C16 14S 26 14S C20 C20 C 0 1 Y N N 34.560 19.895 13.249 5.186 2.441 0.518 C20 14S 27 14S C23 C23 C 0 1 Y N N 35.910 20.163 13.481 5.756 2.776 1.731 C23 14S 28 14S C27 C27 C 0 1 Y N N 36.289 21.321 14.153 7.117 3.010 1.815 C27 14S 29 14S C30 C30 C 0 1 Y N N 35.313 22.210 14.593 7.909 2.909 0.687 C30 14S 30 14S C25 C25 C 0 1 Y N N 33.965 21.946 14.364 7.343 2.576 -0.529 C25 14S 31 14S C22 C22 C 0 1 Y N N 33.584 20.783 13.696 5.980 2.335 -0.615 C22 14S 32 14S O26 O26 O 0 1 N N N 32.253 20.532 13.460 5.422 2.001 -1.808 O26 14S 33 14S C31 C31 C 0 1 N N N 31.321 20.395 14.529 6.299 1.909 -2.932 C31 14S 34 14S H1 H1 H 0 1 N N N 34.628 8.806 22.760 -8.662 3.692 -1.051 H1 14S 35 14S H2 H2 H 0 1 N N N 35.146 10.524 22.680 -9.922 2.470 -0.691 H2 14S 36 14S H3 H3 H 0 1 N N N 32.898 11.096 22.876 -7.867 3.704 1.171 H3 14S 37 14S H4 H4 H 0 1 N N N 32.381 9.395 22.624 -9.531 3.138 1.536 H4 14S 38 14S H5 H5 H 0 1 N N N 32.544 11.630 20.624 -7.279 1.626 2.119 H5 14S 39 14S H6 H6 H 0 1 N N N 31.669 10.066 20.500 -8.859 0.891 1.719 H6 14S 40 14S H7 H7 H 0 1 N N N 32.546 9.848 18.297 -6.751 -0.812 0.885 H7 14S 41 14S H8 H8 H 0 1 N N N 34.088 8.929 18.231 -6.697 -0.667 -0.888 H8 14S 42 14S H9 H9 H 0 1 N N N 35.208 11.292 18.589 -4.933 1.065 -0.693 H9 14S 43 14S H10 H10 H 0 1 N N N 33.625 11.933 18.034 -4.988 0.920 1.080 H10 14S 44 14S H11 H11 H 0 1 N N N 33.965 10.254 16.033 -4.340 -1.467 0.905 H11 14S 45 14S H12 H12 H 0 1 N N N 35.691 10.320 16.525 -4.286 -1.322 -0.868 H12 14S 46 14S H13 H13 H 0 1 N N N 35.811 12.474 15.701 -2.609 0.662 0.238 H13 14S 47 14S H14 H14 H 0 1 N N N 31.587 14.148 14.702 -0.364 -3.262 0.136 H14 14S 48 14S H15 H15 H 0 1 N N N 30.879 16.454 14.087 2.386 -3.370 1.143 H15 14S 49 14S H16 H16 H 0 1 N N N 32.051 16.896 16.654 1.615 -3.991 -1.707 H16 14S 50 14S H17 H17 H 0 1 N N N 31.035 18.029 15.701 3.206 -3.507 -1.038 H17 14S 51 14S H18 H18 H 0 1 N N N 30.381 16.703 18.173 2.821 -6.074 -1.766 H18 14S 52 14S H19 H19 H 0 1 N N N 29.343 17.790 17.190 3.661 -5.728 -0.220 H19 14S 53 14S H20 H20 H 0 1 N N N 28.050 15.969 16.726 0.709 -6.441 -0.669 H20 14S 54 14S H21 H21 H 0 1 N N N 29.257 14.853 17.449 1.855 -7.157 0.505 H21 14S 55 14S H22 H22 H 0 1 N N N 28.835 15.604 14.605 1.649 -5.363 1.986 H22 14S 56 14S H23 H23 H 0 1 N N N 29.702 14.193 15.301 0.081 -5.131 1.162 H23 14S 57 14S H24 H24 H 0 1 N N N 36.121 13.508 14.079 -0.900 1.436 0.143 H24 14S 58 14S H25 H25 H 0 1 N N N 35.345 17.278 11.724 4.199 0.123 0.481 H25 14S 59 14S H26 H26 H 0 1 N N N 34.044 18.887 11.442 3.316 2.622 -0.494 H26 14S 60 14S H27 H27 H 0 1 N N N 33.168 18.318 12.903 3.203 2.642 1.282 H27 14S 61 14S H28 H28 H 0 1 N N N 36.663 19.469 13.138 5.140 2.855 2.614 H28 14S 62 14S H29 H29 H 0 1 N N N 37.334 21.528 14.332 7.561 3.271 2.764 H29 14S 63 14S H30 H30 H 0 1 N N N 35.603 23.110 15.115 8.971 3.092 0.755 H30 14S 64 14S H31 H31 H 0 1 N N N 33.214 22.643 14.704 7.962 2.498 -1.410 H31 14S 65 14S H32 H32 H 0 1 N N N 30.319 20.199 14.120 6.783 2.872 -3.094 H32 14S 66 14S H33 H33 H 0 1 N N N 31.624 19.557 15.174 7.057 1.150 -2.740 H33 14S 67 14S H34 H34 H 0 1 N N N 31.301 21.323 15.119 5.727 1.636 -3.818 H34 14S 68 # 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 14S C16 N12 SING N N 1 14S C16 C20 SING N N 2 14S N12 C7 SING N N 3 14S C20 C23 DOUB Y N 4 14S C20 C22 SING Y N 5 14S C7 N9 DOUB Y N 6 14S C7 N3 SING Y N 7 14S N9 C5 SING Y N 8 14S O26 C22 SING N N 9 14S O26 C31 SING N N 10 14S C23 C27 SING Y N 11 14S C22 C25 DOUB Y N 12 14S N3 C1 DOUB Y N 13 14S C5 C2 DOUB Y N 14 14S C27 C30 DOUB Y N 15 14S C25 C30 SING Y N 16 14S C1 C2 SING Y N 17 14S C1 N4 SING N N 18 14S C2 C6 SING N N 19 14S C8 N4 SING N N 20 14S C8 C13 SING N N 21 14S C8 C14 SING N N 22 14S C6 O11 DOUB N N 23 14S C6 N10 SING N N 24 14S C13 C17 SING N N 25 14S N10 C15 SING N N 26 14S C14 C18 SING N N 27 14S C15 C19 SING N N 28 14S C17 C18 SING N N 29 14S C19 C21 SING N N 30 14S C21 N24 SING N N 31 14S N24 C28 SING N N 32 14S N24 C29 SING N N 33 14S O33 C28 DOUB N N 34 14S C28 C32 SING N N 35 14S C29 C34 SING N N 36 14S C32 C34 SING N N 37 14S C32 H1 SING N N 38 14S C32 H2 SING N N 39 14S C34 H3 SING N N 40 14S C34 H4 SING N N 41 14S C29 H5 SING N N 42 14S C29 H6 SING N N 43 14S C21 H7 SING N N 44 14S C21 H8 SING N N 45 14S C19 H9 SING N N 46 14S C19 H10 SING N N 47 14S C15 H11 SING N N 48 14S C15 H12 SING N N 49 14S N10 H13 SING N N 50 14S N4 H14 SING N N 51 14S C8 H15 SING N N 52 14S C14 H16 SING N N 53 14S C14 H17 SING N N 54 14S C18 H18 SING N N 55 14S C18 H19 SING N N 56 14S C17 H20 SING N N 57 14S C17 H21 SING N N 58 14S C13 H22 SING N N 59 14S C13 H23 SING N N 60 14S C5 H24 SING N N 61 14S N12 H25 SING N N 62 14S C16 H26 SING N N 63 14S C16 H27 SING N N 64 14S C23 H28 SING N N 65 14S C27 H29 SING N N 66 14S C30 H30 SING N N 67 14S C25 H31 SING N N 68 14S C31 H32 SING N N 69 14S C31 H33 SING N N 70 14S C31 H34 SING N N 71 # 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 14S SMILES ACDLabs 12.01 "O=C4N(CCCNC(=O)c2cnc(nc2NC1CCCC1)NCc3ccccc3OC)CCC4" 14S InChI InChI 1.03 "InChI=1S/C25H34N6O3/c1-34-21-11-5-2-8-18(21)16-27-25-28-17-20(23(30-25)29-19-9-3-4-10-19)24(33)26-13-7-15-31-14-6-12-22(31)32/h2,5,8,11,17,19H,3-4,6-7,9-10,12-16H2,1H3,(H,26,33)(H2,27,28,29,30)" 14S InChIKey InChI 1.03 ZXZLVQGNVOKCAS-UHFFFAOYSA-N 14S SMILES_CANONICAL CACTVS 3.370 "COc1ccccc1CNc2ncc(C(=O)NCCCN3CCCC3=O)c(NC4CCCC4)n2" 14S SMILES CACTVS 3.370 "COc1ccccc1CNc2ncc(C(=O)NCCCN3CCCC3=O)c(NC4CCCC4)n2" 14S SMILES_CANONICAL "OpenEye OEToolkits" 1.7.6 "COc1ccccc1CNc2ncc(c(n2)NC3CCCC3)C(=O)NCCCN4CCCC4=O" 14S SMILES "OpenEye OEToolkits" 1.7.6 "COc1ccccc1CNc2ncc(c(n2)NC3CCCC3)C(=O)NCCCN4CCCC4=O" # 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 14S "SYSTEMATIC NAME" ACDLabs 12.01 "4-(cyclopentylamino)-2-[(2-methoxybenzyl)amino]-N-[3-(2-oxopyrrolidin-1-yl)propyl]pyrimidine-5-carboxamide" 14S "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.7.6 "4-(cyclopentylamino)-2-[(2-methoxyphenyl)methylamino]-N-[3-(2-oxidanylidenepyrrolidin-1-yl)propyl]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 14S "Create component" 2012-10-09 RCSB 14S "Initial release" 2013-03-13 RCSB #