data_1RP # _chem_comp.id 1RP _chem_comp.name "6-fluoro-3-oxo-4-(5-O-phosphono-beta-D-ribofuranosyl)-3,4-dihydropyrazine-2-carboxamide" _chem_comp.type NON-POLYMER _chem_comp.pdbx_type HETAIN _chem_comp.formula "C10 H13 F N3 O9 P" _chem_comp.mon_nstd_parent_comp_id ? _chem_comp.pdbx_synonyms ? _chem_comp.pdbx_formal_charge 0 _chem_comp.pdbx_initial_date 2013-05-09 _chem_comp.pdbx_modified_date 2013-08-09 _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 369.197 _chem_comp.one_letter_code ? _chem_comp.three_letter_code 1RP _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 4KN6 _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 1RP OAG OAG O 0 1 N N N 0.804 -26.420 -18.801 -6.086 -0.217 0.212 OAG 1RP 1 1RP PAX PAX P 0 1 N N N 1.219 -24.957 -19.134 -4.819 -1.202 0.340 PAX 1RP 2 1RP OAH OAH O 0 1 N N N 0.026 -24.152 -19.495 -5.042 -2.204 1.580 OAH 1RP 3 1RP OAC OAC O 0 1 N N N 2.193 -24.970 -20.285 -4.675 -1.985 -0.907 OAC 1RP 4 1RP "O5'" "O5'" O 0 1 N N N 1.935 -24.326 -17.900 -3.486 -0.333 0.585 "O5'" 1RP 5 1RP "C5'" "C5'" C 0 1 N N N 3.255 -24.649 -17.679 -2.960 0.575 -0.385 "C5'" 1RP 6 1RP "C4'" "C4'" C 0 1 N N R 3.830 -24.209 -16.441 -1.693 1.232 0.167 "C4'" 1RP 7 1RP "O4'" "O4'" O 0 1 N N N 4.928 -23.350 -16.675 -0.622 0.267 0.253 "O4'" 1RP 8 1RP "C3'" "C3'" C 0 1 N N S 2.830 -23.407 -15.702 -1.176 2.309 -0.813 "C3'" 1RP 9 1RP "O3'" "O3'" O 0 1 N N N 2.436 -24.090 -14.583 -1.596 3.609 -0.396 "O3'" 1RP 10 1RP "C2'" "C2'" C 0 1 N N R 3.497 -22.192 -15.336 0.362 2.185 -0.729 "C2'" 1RP 11 1RP "O2'" "O2'" O 0 1 N N N 3.280 -21.907 -14.017 0.938 3.405 -0.258 "O2'" 1RP 12 1RP "C1'" "C1'" C 0 1 N N R 4.942 -22.476 -15.574 0.592 1.048 0.291 "C1'" 1RP 13 1RP NAW NAW N 0 1 N N N 5.624 -21.257 -15.827 1.739 0.228 -0.109 NAW 1RP 14 1RP CAQ CAQ C 0 1 N N N 5.455 -20.668 -17.022 2.823 0.135 0.691 CAQ 1RP 15 1RP OAD OAD O 0 1 N N N 4.616 -21.266 -17.986 2.865 0.729 1.754 OAD 1RP 16 1RP CAJ CAJ C 0 1 N N N 6.411 -20.712 -14.896 1.720 -0.447 -1.278 CAJ 1RP 17 1RP CAP CAP C 0 1 N N N 7.074 -19.511 -15.163 2.790 -1.219 -1.662 CAP 1RP 18 1RP FAI FAI F 0 1 N N N 7.852 -18.950 -14.273 2.737 -1.882 -2.839 FAI 1RP 19 1RP NAL NAL N 0 1 N N N 6.903 -18.926 -16.360 3.871 -1.329 -0.907 NAL 1RP 20 1RP CAR CAR C 0 1 N N N 6.115 -19.472 -17.289 3.949 -0.696 0.253 CAR 1RP 21 1RP CAO CAO C 0 1 N N N 5.944 -18.766 -18.645 5.153 -0.825 1.095 CAO 1RP 22 1RP OAB OAB O 0 1 N N N 5.130 -19.229 -19.512 5.216 -0.241 2.159 OAB 1RP 23 1RP NAA NAA N 0 1 N N N 6.704 -17.592 -18.914 6.183 -1.591 0.684 NAA 1RP 24 1RP H1 H1 H 0 1 N N N 1.249 -27.018 -19.390 -6.241 0.329 0.995 H1 1RP 25 1RP H2 H2 H 0 1 N N N 0.127 -23.813 -20.377 -5.829 -2.760 1.500 H2 1RP 26 1RP H3 H3 H 0 1 N N N 3.340 -25.745 -17.714 -2.718 0.031 -1.298 H3 1RP 27 1RP H4 H4 H 0 1 N N N 3.846 -24.209 -18.496 -3.701 1.343 -0.605 H4 1RP 28 1RP H5 H5 H 0 1 N N N 4.136 -25.073 -15.833 -1.889 1.672 1.144 H5 1RP 29 1RP H6 H6 H 0 1 N N N 1.974 -23.189 -16.358 -1.521 2.102 -1.826 H6 1RP 30 1RP H7 H7 H 0 1 N N N 1.794 -23.576 -14.108 -1.299 4.324 -0.975 H7 1RP 31 1RP H8 H8 H 0 1 N N N 3.172 -21.365 -15.985 0.777 1.918 -1.702 H8 1RP 32 1RP H9 H9 H 0 1 N N N 3.727 -21.100 -13.789 0.772 4.166 -0.831 H9 1RP 33 1RP H10 H10 H 0 1 N N N 5.365 -22.975 -14.690 0.748 1.459 1.288 H10 1RP 34 1RP H11 H11 H 0 1 N N N 6.535 -21.198 -13.939 0.853 -0.379 -1.918 H11 1RP 35 1RP H14 H14 H 0 1 N N N 6.603 -17.121 -19.790 6.132 -2.058 -0.165 H14 1RP 36 1RP H15 H15 H 0 1 N N N 7.339 -17.239 -18.227 6.975 -1.677 1.238 H15 1RP 37 # 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 1RP OAC PAX DOUB N N 1 1RP OAB CAO DOUB N N 2 1RP OAH PAX SING N N 3 1RP PAX OAG SING N N 4 1RP PAX "O5'" SING N N 5 1RP NAA CAO SING N N 6 1RP CAO CAR SING N N 7 1RP OAD CAQ DOUB N N 8 1RP "O5'" "C5'" SING N N 9 1RP "C5'" "C4'" SING N N 10 1RP CAR CAQ SING N N 11 1RP CAR NAL DOUB N N 12 1RP CAQ NAW SING N N 13 1RP "O4'" "C4'" SING N N 14 1RP "O4'" "C1'" SING N N 15 1RP "C4'" "C3'" SING N N 16 1RP NAL CAP SING N N 17 1RP NAW "C1'" SING N N 18 1RP NAW CAJ SING N N 19 1RP "C3'" "C2'" SING N N 20 1RP "C3'" "O3'" SING N N 21 1RP "C1'" "C2'" SING N N 22 1RP "C2'" "O2'" SING N N 23 1RP CAP CAJ DOUB N N 24 1RP CAP FAI SING N N 25 1RP OAG H1 SING N N 26 1RP OAH H2 SING N N 27 1RP "C5'" H3 SING N N 28 1RP "C5'" H4 SING N N 29 1RP "C4'" H5 SING N N 30 1RP "C3'" H6 SING N N 31 1RP "O3'" H7 SING N N 32 1RP "C2'" H8 SING N N 33 1RP "O2'" H9 SING N N 34 1RP "C1'" H10 SING N N 35 1RP CAJ H11 SING N N 36 1RP NAA H14 SING N N 37 1RP NAA H15 SING N N 38 # 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 1RP SMILES ACDLabs 12.01 "O=P(O)(O)OCC2OC(N1C(=O)C(=NC(F)=C1)C(=O)N)C(O)C2O" 1RP InChI InChI 1.03 "InChI=1S/C10H13FN3O9P/c11-4-1-14(9(18)5(13-4)8(12)17)10-7(16)6(15)3(23-10)2-22-24(19,20)21/h1,3,6-7,10,15-16H,2H2,(H2,12,17)(H2,19,20,21)/t3-,6-,7-,10-/m1/s1" 1RP InChIKey InChI 1.03 RWCWUNIDADUVEZ-KAFVXXCXSA-N 1RP SMILES_CANONICAL CACTVS 3.370 "NC(=O)C1=NC(=CN([C@@H]2O[C@H](CO[P](O)(O)=O)[C@@H](O)[C@H]2O)C1=O)F" 1RP SMILES CACTVS 3.370 "NC(=O)C1=NC(=CN([CH]2O[CH](CO[P](O)(O)=O)[CH](O)[CH]2O)C1=O)F" 1RP SMILES_CANONICAL "OpenEye OEToolkits" 1.7.6 "C1=C(N=C(C(=O)N1[C@H]2[C@@H]([C@@H]([C@H](O2)COP(=O)(O)O)O)O)C(=O)N)F" 1RP SMILES "OpenEye OEToolkits" 1.7.6 "C1=C(N=C(C(=O)N1C2C(C(C(O2)COP(=O)(O)O)O)O)C(=O)N)F" # 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 1RP "SYSTEMATIC NAME" ACDLabs 12.01 "6-fluoro-3-oxo-4-(5-O-phosphono-beta-D-ribofuranosyl)-3,4-dihydropyrazine-2-carboxamide" 1RP "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.7.6 "[(2R,3S,4R,5R)-5-(3-aminocarbonyl-5-fluoranyl-2-oxidanylidene-pyrazin-1-yl)-3,4-bis(oxidanyl)oxolan-2-yl]methyl dihydrogen phosphate" # loop_ _pdbx_chem_comp_audit.comp_id _pdbx_chem_comp_audit.action_type _pdbx_chem_comp_audit.date _pdbx_chem_comp_audit.processing_site 1RP "Create component" 2013-05-09 RCSB 1RP "Other modification" 2013-05-09 RCSB 1RP "Initial release" 2013-08-14 RCSB #