data_GFL # _chem_comp.id GFL _chem_comp.name "2-AMINO-9-(2-DEOXY-2-FLUORO-5-O-PHOSPHONO-BETA-D-ARABINOFURANOSYL)-1,9-DIHYDRO-6H-PURIN-6-ONE" _chem_comp.type "DNA LINKING" _chem_comp.pdbx_type ATOMN _chem_comp.formula "C10 H13 F N5 O7 P" _chem_comp.mon_nstd_parent_comp_id DG _chem_comp.pdbx_synonyms "2'-FLUORO-2-DEOXY-GUANOSINE-5'-MONOPHOSPHATE" _chem_comp.pdbx_formal_charge 0 _chem_comp.pdbx_initial_date 2006-09-07 _chem_comp.pdbx_modified_date 2021-03-01 _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 365.212 _chem_comp.one_letter_code G _chem_comp.three_letter_code GFL _chem_comp.pdbx_model_coordinates_details ? _chem_comp.pdbx_model_coordinates_missing_flag N _chem_comp.pdbx_ideal_coordinates_details ? _chem_comp.pdbx_ideal_coordinates_missing_flag N _chem_comp.pdbx_model_coordinates_db_code ? _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 GFL O3P O3P O 0 1 N Y N -9.951 2.872 9.172 5.663 -1.915 -1.302 O3P GFL 1 GFL P P P 0 1 N N N -9.616 2.281 7.702 5.050 -0.836 -0.276 P GFL 2 GFL O1P O1P O 0 1 N N N -10.702 1.354 7.312 4.844 -1.472 1.044 O1P GFL 3 GFL O2P O2P O 0 1 N N N -8.212 1.812 7.696 6.070 0.400 -0.123 O2P GFL 4 GFL "O5'" O5* O 0 1 N N N -9.713 3.591 6.757 3.640 -0.301 -0.840 "O5'" GFL 5 GFL "C5'" C5* C 0 1 N N N -9.677 4.918 7.322 3.093 0.558 0.163 "C5'" GFL 6 GFL "C4'" C4* C 0 1 N N R -8.273 5.501 7.402 1.745 1.104 -0.312 "C4'" GFL 7 GFL "O4'" O4* O 0 1 N N N -7.384 4.654 8.172 0.778 0.036 -0.413 "O4'" GFL 8 GFL "C3'" C3* C 0 1 N N R -7.636 5.658 6.007 1.155 2.073 0.736 "C3'" GFL 9 GFL "O3'" O3* O 0 1 N N N -7.586 7.060 5.627 1.426 3.428 0.373 "O3'" GFL 10 GFL "C2'" C2* C 0 1 N N S -6.251 5.078 6.177 -0.366 1.793 0.693 "C2'" GFL 11 GFL "C1'" C1* C 0 1 N N R -6.084 4.933 7.669 -0.512 0.685 -0.374 "C1'" GFL 12 GFL N9 N9 N 0 1 Y N N -5.068 3.918 7.996 -1.551 -0.269 0.020 N9 GFL 13 GFL C8 C8 C 0 1 Y N N -5.179 2.605 8.308 -1.360 -1.433 0.706 C8 GFL 14 GFL N7 N7 N 0 1 Y N N -4.081 1.957 8.554 -2.502 -2.032 0.884 N7 GFL 15 GFL C5 C5 C 0 1 Y N N -3.114 2.963 8.385 -3.489 -1.291 0.326 C5 GFL 16 GFL C6 C6 C 0 1 N N N -1.690 2.920 8.508 -4.891 -1.442 0.214 C6 GFL 17 GFL O6 O6 O 0 1 N N N -0.967 1.971 8.808 -5.454 -2.415 0.686 O6 GFL 18 GFL N1 N1 N 0 1 N N N -1.123 4.159 8.247 -5.592 -0.478 -0.423 N1 GFL 19 GFL C2 C2 C 0 1 N N N -1.824 5.296 7.912 -4.952 0.603 -0.951 C2 GFL 20 GFL N2 N2 N 0 1 N N N -1.117 6.390 7.692 -5.688 1.563 -1.598 N2 GFL 21 GFL N3 N3 N 0 1 N N N -3.139 5.345 7.797 -3.650 0.755 -0.854 N3 GFL 22 GFL C4 C4 C 0 1 Y N N -3.721 4.157 8.044 -2.892 -0.155 -0.232 C4 GFL 23 GFL F F F 0 1 N N N -6.172 3.860 5.559 -0.816 1.339 1.937 F GFL 24 GFL HO3P HO3P H 0 0 N N N -10.017 2.157 9.794 6.505 -2.209 -0.928 HO3P GFL 25 GFL HO2P HO2P H 0 0 N N N -7.915 1.712 6.799 6.177 0.785 -1.004 HO2P GFL 26 GFL "H5'1" 1H5* H 0 0 N N N -10.288 5.578 6.688 3.777 1.387 0.344 "H5'1" GFL 27 GFL "H5'2" 2H5* H 0 0 N N N -10.061 4.847 8.350 2.952 -0.005 1.086 "H5'2" GFL 28 GFL "H4'" H4* H 0 1 N N N -8.391 6.482 7.885 1.857 1.606 -1.273 "H4'" GFL 29 GFL "H3'" H3* H 0 1 N N N -8.203 5.153 5.211 1.556 1.856 1.726 "H3'" GFL 30 GFL "HO3'" HO3* H 0 0 N N N -7.575 7.600 6.408 1.035 3.985 1.061 "HO3'" GFL 31 GFL "H2'" H2* H 0 1 N N N -5.468 5.709 5.732 -0.911 2.689 0.395 "H2'" GFL 32 GFL "H1'" H1* H 0 1 N N N -5.696 5.845 8.147 -0.746 1.122 -1.344 "H1'" GFL 33 GFL H8 H8 H 0 1 N N N -6.141 2.117 8.350 -0.405 -1.802 1.049 H8 GFL 34 GFL HN1 HN1 H 0 1 N N N -0.127 4.232 8.307 -6.554 -0.560 -0.512 HN1 GFL 35 GFL HN21 1HN2 H 0 0 N N N -1.714 7.156 7.453 -5.247 2.340 -1.976 HN21 GFL 36 GFL HN22 2HN2 H 0 0 N N N -0.121 6.445 7.756 -6.650 1.463 -1.681 HN22 GFL 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 GFL O3P P SING N N 1 GFL O3P HO3P SING N N 2 GFL P O1P DOUB N N 3 GFL P O2P SING N N 4 GFL P "O5'" SING N N 5 GFL O2P HO2P SING N N 6 GFL "O5'" "C5'" SING N N 7 GFL "C5'" "C4'" SING N N 8 GFL "C5'" "H5'1" SING N N 9 GFL "C5'" "H5'2" SING N N 10 GFL "C4'" "O4'" SING N N 11 GFL "C4'" "C3'" SING N N 12 GFL "C4'" "H4'" SING N N 13 GFL "O4'" "C1'" SING N N 14 GFL "C3'" "O3'" SING N N 15 GFL "C3'" "C2'" SING N N 16 GFL "C3'" "H3'" SING N N 17 GFL "O3'" "HO3'" SING N N 18 GFL "C2'" "C1'" SING N N 19 GFL "C2'" F SING N N 20 GFL "C2'" "H2'" SING N N 21 GFL "C1'" N9 SING N N 22 GFL "C1'" "H1'" SING N N 23 GFL N9 C8 SING Y N 24 GFL N9 C4 SING Y N 25 GFL C8 N7 DOUB Y N 26 GFL C8 H8 SING N N 27 GFL N7 C5 SING Y N 28 GFL C5 C6 SING N N 29 GFL C5 C4 DOUB Y N 30 GFL C6 O6 DOUB N N 31 GFL C6 N1 SING N N 32 GFL N1 C2 SING N N 33 GFL N1 HN1 SING N N 34 GFL C2 N2 SING N N 35 GFL C2 N3 DOUB N N 36 GFL N2 HN21 SING N N 37 GFL N2 HN22 SING N N 38 GFL N3 C4 SING N N 39 # # 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 GFL SMILES ACDLabs 10.04 "O=C1c2ncn(c2N=C(N)N1)C3OC(C(O)C3F)COP(=O)(O)O" GFL SMILES_CANONICAL CACTVS 3.341 "NC1=Nc2n(cnc2C(=O)N1)[C@@H]3O[C@H](CO[P](O)(O)=O)[C@@H](O)[C@@H]3F" GFL SMILES CACTVS 3.341 "NC1=Nc2n(cnc2C(=O)N1)[CH]3O[CH](CO[P](O)(O)=O)[CH](O)[CH]3F" GFL SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 "c1nc2c(n1[C@H]3[C@H]([C@@H]([C@H](O3)COP(=O)(O)O)O)F)N=C(NC2=O)N" GFL SMILES "OpenEye OEToolkits" 1.5.0 "c1nc2c(n1C3C(C(C(O3)COP(=O)(O)O)O)F)N=C(NC2=O)N" GFL InChI InChI 1.03 "InChI=1S/C10H13FN5O7P/c11-4-6(17)3(1-22-24(19,20)21)23-9(4)16-2-13-5-7(16)14-10(12)15-8(5)18/h2-4,6,9,17H,1H2,(H2,19,20,21)(H3,12,14,15,18)/t3-,4+,6-,9-/m1/s1" GFL InChIKey InChI 1.03 ZTDPJNQLNRZPCT-AYQXTPAHSA-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 GFL "SYSTEMATIC NAME" ACDLabs 10.04 "2-amino-9-(2-deoxy-2-fluoro-5-O-phosphono-beta-D-arabinofuranosyl)-1,9-dihydro-6H-purin-6-one" GFL "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "[(2R,3R,4S,5R)-5-(2-amino-6-oxo-1H-purin-9-yl)-4-fluoro-3-hydroxy-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 GFL "Create component" 2006-09-07 RCSB GFL "Modify descriptor" 2011-06-04 RCSB GFL "Modify synonyms" 2021-03-01 PDBE # _pdbx_chem_comp_synonyms.ordinal 1 _pdbx_chem_comp_synonyms.comp_id GFL _pdbx_chem_comp_synonyms.name "2'-FLUORO-2-DEOXY-GUANOSINE-5'-MONOPHOSPHATE" _pdbx_chem_comp_synonyms.provenance ? _pdbx_chem_comp_synonyms.type ? ##