data_58H # _chem_comp.id 58H _chem_comp.name "methyl (4R)-4-(2-chloro-4-fluorophenyl)-6-{[4-(3-hydroxypenta-1,4-diyn-3-yl)piperidin-1-yl]methyl}-2-(pyridin-2-yl)-1,4-dihydropyrimidine-5-carboxylate" _chem_comp.type NON-POLYMER _chem_comp.pdbx_type HETAIN _chem_comp.formula "C28 H26 Cl F N4 O3" _chem_comp.mon_nstd_parent_comp_id ? _chem_comp.pdbx_synonyms ? _chem_comp.pdbx_formal_charge 0 _chem_comp.pdbx_initial_date 2015-08-20 _chem_comp.pdbx_modified_date 2016-02-12 _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 520.982 _chem_comp.one_letter_code ? _chem_comp.three_letter_code 58H _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 5D7Y _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 58H C14 C1 C 0 1 N N N 188.001 -3.969 235.821 5.729 -1.119 2.201 C14 58H 1 58H C11 C2 C 0 1 N N N 188.660 -6.046 237.947 3.163 -1.006 0.846 C11 58H 2 58H CL3 CL1 CL 0 0 N N N 191.550 -11.275 239.968 -4.569 2.345 0.199 CL3 58H 3 58H C01 C3 C 0 1 N N N 186.841 -12.839 238.261 -0.144 3.382 -3.516 C01 58H 4 58H O02 O1 O 0 1 N N N 187.950 -11.969 238.017 -0.884 2.484 -2.686 O02 58H 5 58H C03 C4 C 0 1 N N N 188.739 -12.409 237.010 -0.311 1.294 -2.408 C03 58H 6 58H C04 C5 C 0 1 N N N 189.989 -11.636 236.965 -0.987 0.357 -1.593 C04 58H 7 58H C05 C6 C 0 1 N N N 190.090 -10.295 236.844 -0.469 -0.875 -1.428 C05 58H 8 58H C06 C7 C 0 1 N N N 188.911 -9.344 236.735 0.829 -1.247 -2.099 C06 58H 9 58H N07 N1 N 0 1 N N N 188.610 -8.565 238.010 1.955 -0.790 -1.274 N07 58H 10 58H C08 C8 C 0 1 N N N 187.132 -8.290 238.208 3.207 -0.796 -2.043 C08 58H 11 58H C09 C9 C 0 1 N N N 186.614 -7.290 237.188 4.326 -0.180 -1.201 C09 58H 12 58H C10 C10 C 0 1 N N N 187.644 -6.210 236.796 4.493 -0.988 0.089 C10 58H 13 58H C12 C11 C 0 1 N N N 189.441 -7.329 238.232 2.077 -1.599 -0.055 C12 58H 14 58H C13 C12 C 0 1 N N N 186.972 -4.867 236.383 5.570 -0.341 0.962 C13 58H 15 58H C15 C13 C 0 1 N N N 188.802 -3.280 235.251 5.857 -1.739 3.190 C15 58H 16 58H O16 O2 O 0 1 N N N 186.429 -4.257 237.551 5.181 0.996 1.285 O16 58H 17 58H C17 C14 C 0 1 N N N 185.911 -5.086 235.380 6.847 -0.317 0.230 C17 58H 18 58H C18 C15 C 0 1 N N N 185.075 -5.254 234.534 7.865 -0.298 -0.354 C18 58H 19 58H N19 N2 N 0 1 N N N 191.373 -9.782 236.781 -1.127 -1.788 -0.647 N19 58H 20 58H C20 C16 C 0 1 N N N 192.503 -10.556 236.933 -2.455 -1.584 -0.331 C20 58H 21 58H C21 C17 C 0 1 Y N N 193.808 -9.860 237.095 -3.268 -2.722 0.160 C21 58H 22 58H C22 C18 C 0 1 Y N N 194.841 -10.513 237.762 -4.609 -2.524 0.481 C22 58H 23 58H C23 C19 C 0 1 Y N N 196.012 -9.818 237.973 -5.356 -3.598 0.939 C23 58H 24 58H C24 C20 C 0 1 Y N N 196.108 -8.523 237.489 -4.736 -4.832 1.060 C24 58H 25 58H C25 C21 C 0 1 Y N N 195.022 -7.947 236.845 -3.399 -4.956 0.722 C25 58H 26 58H N26 N3 N 0 1 Y N N 193.844 -8.578 236.648 -2.714 -3.921 0.285 N26 58H 27 58H N27 N4 N 0 1 N N N 192.499 -11.843 237.009 -3.004 -0.420 -0.455 N27 58H 28 58H C28 C22 C 0 1 N N R 191.203 -12.533 237.047 -2.269 0.753 -0.918 C28 58H 29 58H C29 C23 C 0 1 Y N N 191.152 -13.422 238.290 -1.955 1.641 0.258 C29 58H 30 58H C30 C24 C 0 1 Y N N 191.268 -12.934 239.608 -2.954 2.407 0.834 C30 58H 31 58H C32 C25 C 0 1 Y N N 191.125 -13.784 240.701 -2.665 3.222 1.913 C32 58H 32 58H C33 C26 C 0 1 Y N N 190.872 -15.122 240.481 -1.377 3.271 2.418 C33 58H 33 58H C35 C27 C 0 1 Y N N 190.807 -15.643 239.199 -0.379 2.504 1.842 C35 58H 34 58H C36 C28 C 0 1 Y N N 190.937 -14.799 238.104 -0.670 1.686 0.766 C36 58H 35 58H O37 O3 O 0 1 N N N 188.516 -13.351 236.267 0.788 1.028 -2.859 O37 58H 36 58H F34 F1 F 0 1 N N N 190.682 -15.932 241.524 -1.094 4.067 3.472 F34 58H 37 58H H1 H1 H 0 1 N N N 189.373 -5.253 237.677 3.263 -1.616 1.744 H1 58H 38 58H H2 H2 H 0 1 N N N 188.116 -5.756 238.858 2.888 0.011 1.126 H2 58H 39 58H H3 H3 H 0 1 N N N 186.234 -12.437 239.086 -0.717 4.298 -3.660 H3 58H 40 58H H4 H4 H 0 1 N N N 186.224 -12.910 237.353 0.806 3.619 -3.037 H4 58H 41 58H H5 H5 H 0 1 N N N 187.212 -13.838 238.532 0.042 2.914 -4.482 H5 58H 42 58H H6 H6 H 0 1 N N N 189.124 -8.622 235.933 0.880 -2.330 -2.216 H6 58H 43 58H H7 H7 H 0 1 N N N 188.019 -9.931 236.472 0.880 -0.773 -3.079 H7 58H 44 58H H9 H9 H 0 1 N N N 186.975 -7.885 239.218 3.469 -1.822 -2.301 H9 58H 45 58H H10 H10 H 0 1 N N N 186.575 -9.232 238.101 3.075 -0.215 -2.955 H10 58H 46 58H H11 H11 H 0 1 N N N 185.730 -6.789 237.611 5.258 -0.199 -1.766 H11 58H 47 58H H12 H12 H 0 1 N N N 186.325 -7.839 236.280 4.071 0.851 -0.955 H12 58H 48 58H H13 H13 H 0 1 N N N 188.195 -6.582 235.920 4.787 -2.009 -0.157 H13 58H 49 58H H14 H14 H 0 1 N N N 190.315 -7.366 237.566 2.344 -2.621 -0.322 H14 58H 50 58H H15 H15 H 0 1 N N N 189.778 -7.313 239.279 1.125 -1.600 0.477 H15 58H 51 58H H16 H16 H 0 1 N N N 189.509 -2.672 234.748 5.971 -2.294 4.074 H16 58H 52 58H H17 H17 H 0 1 N N N 187.120 -4.121 238.188 5.058 1.567 0.514 H17 58H 53 58H H18 H18 H 0 1 N N N 184.337 -5.402 233.787 8.776 -0.281 -0.877 H18 58H 54 58H H19 H19 H 0 1 N N N 194.728 -11.532 238.103 -5.060 -1.549 0.375 H19 58H 55 58H H20 H20 H 0 1 N N N 196.836 -10.272 238.503 -6.398 -3.475 1.196 H20 58H 56 58H H21 H21 H 0 1 N N N 197.024 -7.964 237.612 -5.291 -5.688 1.414 H21 58H 57 58H H22 H22 H 0 1 N N N 195.125 -6.936 236.480 -2.913 -5.916 0.816 H22 58H 58 58H H23 H23 H 0 1 N N N 191.211 -13.401 241.707 -3.445 3.820 2.362 H23 58H 59 58H H24 H24 H 0 1 N N N 190.656 -16.702 239.052 0.626 2.542 2.235 H24 58H 60 58H H25 H25 H 0 1 N N N 190.873 -15.202 237.104 0.108 1.085 0.319 H25 58H 61 58H H8 H8 H 0 1 N N N 191.486 -8.802 236.617 -0.663 -2.574 -0.319 H8 58H 62 58H H26 H26 H 0 1 N N N 191.163 -13.205 236.177 -2.889 1.305 -1.625 H26 58H 63 # 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 58H C18 C17 TRIP N N 1 58H C15 C14 TRIP N N 2 58H C17 C13 SING N N 3 58H C14 C13 SING N N 4 58H O37 C03 DOUB N N 5 58H C13 C10 SING N N 6 58H C13 O16 SING N N 7 58H N26 C25 DOUB Y N 8 58H N26 C21 SING Y N 9 58H C06 C05 SING N N 10 58H C06 N07 SING N N 11 58H N19 C05 SING N N 12 58H N19 C20 SING N N 13 58H C10 C09 SING N N 14 58H C10 C11 SING N N 15 58H C05 C04 DOUB N N 16 58H C25 C24 SING Y N 17 58H C20 N27 DOUB N N 18 58H C20 C21 SING N N 19 58H C04 C03 SING N N 20 58H C04 C28 SING N N 21 58H N27 C28 SING N N 22 58H C03 O02 SING N N 23 58H C28 C29 SING N N 24 58H C21 C22 DOUB Y N 25 58H C09 C08 SING N N 26 58H C24 C23 DOUB Y N 27 58H C22 C23 SING Y N 28 58H C11 C12 SING N N 29 58H N07 C08 SING N N 30 58H N07 C12 SING N N 31 58H O02 C01 SING N N 32 58H C36 C29 DOUB Y N 33 58H C36 C35 SING Y N 34 58H C29 C30 SING Y N 35 58H C35 C33 DOUB Y N 36 58H C30 CL3 SING N N 37 58H C30 C32 DOUB Y N 38 58H C33 C32 SING Y N 39 58H C33 F34 SING N N 40 58H C11 H1 SING N N 41 58H C11 H2 SING N N 42 58H C01 H3 SING N N 43 58H C01 H4 SING N N 44 58H C01 H5 SING N N 45 58H C06 H6 SING N N 46 58H C06 H7 SING N N 47 58H C08 H9 SING N N 48 58H C08 H10 SING N N 49 58H C09 H11 SING N N 50 58H C09 H12 SING N N 51 58H C10 H13 SING N N 52 58H C12 H14 SING N N 53 58H C12 H15 SING N N 54 58H C15 H16 SING N N 55 58H O16 H17 SING N N 56 58H C18 H18 SING N N 57 58H C22 H19 SING N N 58 58H C23 H20 SING N N 59 58H C24 H21 SING N N 60 58H C25 H22 SING N N 61 58H C32 H23 SING N N 62 58H C35 H24 SING N N 63 58H C36 H25 SING N N 64 58H N19 H8 SING N N 65 58H C28 H26 SING N N 66 # 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 58H SMILES ACDLabs 12.01 "C(C(C4CCN(CC1=C(C(OC)=O)C(N=C(N1)c2ccccn2)c3c(Cl)cc(F)cc3)CC4)(O)C#C)#C" 58H InChI InChI 1.03 "InChI=1S/C28H26ClFN4O3/c1-4-28(36,5-2)18-11-14-34(15-12-18)17-23-24(27(35)37-3)25(20-10-9-19(30)16-21(20)29)33-26(32-23)22-8-6-7-13-31-22/h1-2,6-10,13,16,18,25,36H,11-12,14-15,17H2,3H3,(H,32,33)" 58H InChIKey InChI 1.03 GKZRJYVILONFJM-UHFFFAOYSA-N 58H SMILES_CANONICAL CACTVS 3.385 "COC(=O)C1=C(CN2CC[C@@H](CC2)C(O)(C#C)C#C)NC(=N[C@H]1c3ccc(F)cc3Cl)c4ccccn4" 58H SMILES CACTVS 3.385 "COC(=O)C1=C(CN2CC[CH](CC2)C(O)(C#C)C#C)NC(=N[CH]1c3ccc(F)cc3Cl)c4ccccn4" 58H SMILES_CANONICAL "OpenEye OEToolkits" 1.9.2 "COC(=O)C1=C(NC(=NC1c2ccc(cc2Cl)F)c3ccccn3)CN4CCC(CC4)C(C#C)(C#C)O" 58H SMILES "OpenEye OEToolkits" 1.9.2 "COC(=O)C1=C(NC(=NC1c2ccc(cc2Cl)F)c3ccccn3)CN4CCC(CC4)C(C#C)(C#C)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 58H "SYSTEMATIC NAME" ACDLabs 12.01 "methyl (4R)-4-(2-chloro-4-fluorophenyl)-6-{[4-(3-hydroxypenta-1,4-diyn-3-yl)piperidin-1-yl]methyl}-2-(pyridin-2-yl)-1,4-dihydropyrimidine-5-carboxylate" 58H "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.9.2 "methyl 4-(2-chloranyl-4-fluoranyl-phenyl)-6-[[4-(3-oxidanylpenta-1,4-diyn-3-yl)piperidin-1-yl]methyl]-2-pyridin-2-yl-1,4-dihydropyrimidine-5-carboxylate" # loop_ _pdbx_chem_comp_audit.comp_id _pdbx_chem_comp_audit.action_type _pdbx_chem_comp_audit.date _pdbx_chem_comp_audit.processing_site 58H "Create component" 2015-08-20 RCSB 58H "Initial release" 2016-02-17 RCSB #