data_GFC # _chem_comp.id GFC _chem_comp.name "5'-O-[(S)-{[(S)-[(S)-chloro(fluoro)phosphonomethyl](hydroxy)phosphoryl]oxy}(hydroxy)phosphoryl]-2'-deoxyguanosine" _chem_comp.type NON-POLYMER _chem_comp.pdbx_type HETAIN _chem_comp.formula "C11 H16 Cl F N5 O12 P3" _chem_comp.mon_nstd_parent_comp_id ? _chem_comp.pdbx_synonyms ? _chem_comp.pdbx_formal_charge 0 _chem_comp.pdbx_initial_date 2009-09-14 _chem_comp.pdbx_modified_date 2011-06-04 _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 557.644 _chem_comp.one_letter_code ? _chem_comp.three_letter_code GFC _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 3JPT _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 GFC N1 N1 N 0 1 N N N 9.716 8.825 8.103 -8.062 2.264 0.205 N1 GFC 1 GFC C2 C2 C 0 1 N N N 8.446 8.967 7.583 -7.632 1.567 1.295 C2 GFC 2 GFC N2 N2 N 0 1 N N N 8.344 9.531 6.359 -8.363 1.627 2.455 N2 GFC 3 GFC N3 N3 N 0 1 N N N 7.353 8.596 8.217 -6.538 0.839 1.267 N3 GFC 4 GFC C4 C4 C 0 1 Y N N 7.625 8.090 9.438 -5.794 0.751 0.159 C4 GFC 5 GFC C5 C5 C 0 1 Y N N 8.847 7.923 10.052 -6.183 1.443 -0.994 C5 GFC 6 GFC C6 C6 C 0 1 N N N 10.011 8.291 9.356 -7.362 2.223 -0.950 C6 GFC 7 GFC O6 O6 O 0 1 N N N 11.182 8.175 9.717 -7.738 2.842 -1.931 O6 GFC 8 GFC N7 N7 N 0 1 Y N N 8.693 7.374 11.318 -5.261 1.179 -1.952 N7 GFC 9 GFC C8 C8 C 0 1 Y N N 7.404 7.207 11.440 -4.352 0.384 -1.467 C8 GFC 10 GFC N9 N9 N 0 1 Y N N 6.702 7.605 10.326 -4.639 0.092 -0.165 N9 GFC 11 GFC PA PA P 0 1 N N N 5.057 5.042 14.665 1.740 -1.905 -0.666 PA GFC 12 GFC PB PB P 0 1 N N N 3.954 2.704 13.726 4.122 -0.145 -0.569 PB GFC 13 GFC PG PG P 0 1 N N N 3.795 1.141 16.416 6.279 1.797 0.094 PG GFC 14 GFC "C1'" "C1'" C 0 1 N N R 5.267 7.508 10.094 -3.854 -0.769 0.723 "C1'" GFC 15 GFC O1A O1A O 0 1 N N N 3.956 5.015 15.652 1.580 -1.670 -2.118 O1A GFC 16 GFC O1B O1B O 0 1 N N N 3.976 2.267 12.063 3.856 0.625 -1.957 O1B GFC 17 GFC O1G O1G O 0 1 N N N 3.446 2.730 16.976 6.013 2.567 -1.295 O1G GFC 18 GFC "C2'" "C2'" C 0 1 N N N 4.842 6.117 9.601 -4.427 -2.199 0.707 "C2'" GFC 19 GFC O2A O2A O 0 1 N N N 6.681 5.181 15.214 2.335 -3.382 -0.424 O2A GFC 20 GFC O2B O2B O 0 1 N N N 2.689 3.229 14.303 5.137 -1.201 -0.777 O2B GFC 21 GFC O2G O2G O 0 1 N N N 4.742 0.110 17.415 6.813 2.844 1.194 O2G GFC 22 GFC "C3'" "C3'" C 0 1 N N S 4.383 5.453 10.885 -3.243 -3.077 0.236 "C3'" GFC 23 GFC "O3'" "O3'" O 0 1 N N N 3.439 4.403 10.628 -3.185 -4.297 0.979 "O3'" GFC 24 GFC O3A O3A O 0 1 N N N 4.957 3.824 13.775 2.751 -0.812 -0.053 O3A GFC 25 GFC C3B C3B C 0 1 N N S 4.543 1.258 14.742 4.727 1.041 0.677 C3B GFC 26 GFC F3B F3B F 0 1 N N N 4.351 0.080 14.094 3.767 2.040 0.874 F3B GFC 27 GFC CL3B CL3B CL 0 0 N N N 6.287 1.458 14.959 5.025 0.179 2.232 CL3B GFC 28 GFC O3G O3G O 0 1 N N N 2.471 0.479 16.332 7.295 0.740 -0.115 O3G GFC 29 GFC "C4'" "C4'" C 0 1 N N R 3.721 6.627 11.599 -2.023 -2.176 0.558 "C4'" GFC 30 GFC "O4'" "O4'" O 0 1 N N N 4.604 7.736 11.337 -2.497 -0.847 0.255 "O4'" GFC 31 GFC "C5'" "C5'" C 0 1 N N N 3.524 6.469 13.088 -0.835 -2.540 -0.335 "C5'" GFC 32 GFC "O5'" "O5'" O 0 1 N N N 4.778 6.313 13.744 0.308 -1.778 0.059 "O5'" GFC 33 GFC HN1 HN1 H 0 1 N N N 10.483 9.128 7.538 -8.876 2.788 0.258 HN1 GFC 34 GFC HN2 HN2 H 0 1 N N N 7.444 9.663 5.943 -9.173 2.160 2.491 HN2 GFC 35 GFC HN2A HN2A H 0 0 N N N 9.168 9.816 5.870 -8.070 1.137 3.239 HN2A GFC 36 GFC H8 H8 H 0 1 N N N 6.937 6.799 12.324 -3.497 0.012 -2.013 H8 GFC 37 GFC "H1'" "H1'" H 0 1 N N N 5.002 8.247 9.323 -3.876 -0.372 1.738 "H1'" GFC 38 GFC "H2'" "H2'" H 0 1 N N N 4.036 6.172 8.854 -4.747 -2.493 1.707 "H2'" GFC 39 GFC "H2'A" "H2'A" H 0 0 N N N 5.675 5.574 9.130 -5.257 -2.270 0.004 "H2'A" GFC 40 GFC "H3'" "H3'" H 0 1 N N N 5.189 4.967 11.454 -3.308 -3.278 -0.833 "H3'" GFC 41 GFC "HO3'" "HO3'" H 0 0 N N N 3.172 4.008 11.450 -3.969 -4.854 0.881 "HO3'" GFC 42 GFC "H4'" "H4'" H 0 1 N N N 2.694 6.745 11.222 -1.753 -2.257 1.610 "H4'" GFC 43 GFC "H5'" "H5'" H 0 1 N N N 3.020 7.364 13.482 -0.615 -3.603 -0.232 "H5'" GFC 44 GFC "H5'A" "H5'A" H 0 0 N N N 2.905 5.579 13.277 -1.079 -2.319 -1.374 "H5'A" GFC 45 GFC H13 H13 H 0 1 N N N 3.119 2.423 11.683 3.200 1.333 -1.895 H13 GFC 46 GFC H14 H14 H 0 1 N N N 2.509 2.823 17.102 5.357 3.274 -1.233 H14 GFC 47 GFC H15 H15 H 0 1 N N N 6.692 5.229 16.163 2.466 -3.605 0.508 H15 GFC 48 GFC H16 H16 H 0 1 N N N 4.220 -0.637 17.685 7.638 3.286 0.950 H16 GFC 49 # 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 GFC N1 C2 SING N N 1 GFC N1 C6 SING N N 2 GFC N1 HN1 SING N N 3 GFC C2 N2 SING N N 4 GFC C2 N3 DOUB N N 5 GFC N2 HN2 SING N N 6 GFC N2 HN2A SING N N 7 GFC N3 C4 SING N N 8 GFC C4 C5 DOUB Y N 9 GFC C4 N9 SING Y N 10 GFC C5 C6 SING N N 11 GFC C5 N7 SING Y N 12 GFC C6 O6 DOUB N N 13 GFC N7 C8 DOUB Y N 14 GFC C8 N9 SING Y N 15 GFC C8 H8 SING N N 16 GFC N9 "C1'" SING N N 17 GFC PA O1A DOUB N N 18 GFC PA O2A SING N N 19 GFC PA O3A SING N N 20 GFC PA "O5'" SING N N 21 GFC PB O1B SING N N 22 GFC PB O2B DOUB N N 23 GFC PB O3A SING N N 24 GFC PB C3B SING N N 25 GFC PG O1G SING N N 26 GFC PG O2G SING N N 27 GFC PG C3B SING N N 28 GFC PG O3G DOUB N N 29 GFC "C1'" "C2'" SING N N 30 GFC "C1'" "O4'" SING N N 31 GFC "C1'" "H1'" SING N N 32 GFC "C2'" "C3'" SING N N 33 GFC "C2'" "H2'" SING N N 34 GFC "C2'" "H2'A" SING N N 35 GFC "C3'" "O3'" SING N N 36 GFC "C3'" "C4'" SING N N 37 GFC "C3'" "H3'" SING N N 38 GFC "O3'" "HO3'" SING N N 39 GFC C3B F3B SING N N 40 GFC C3B CL3B SING N N 41 GFC "C4'" "O4'" SING N N 42 GFC "C4'" "C5'" SING N N 43 GFC "C4'" "H4'" SING N N 44 GFC "C5'" "O5'" SING N N 45 GFC "C5'" "H5'" SING N N 46 GFC "C5'" "H5'A" SING N N 47 GFC O1B H13 SING N N 48 GFC O1G H14 SING N N 49 GFC O2A H15 SING N N 50 GFC O2G H16 SING N N 51 # 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 GFC SMILES ACDLabs 11.02 "O=P(O)(O)C(Cl)(F)P(=O)(O)OP(=O)(O)OCC3OC(n2cnc1c2N=C(N)NC1=O)CC3O" GFC SMILES_CANONICAL CACTVS 3.352 "NC1=Nc2n(cnc2C(=O)N1)[C@H]3C[C@H](O)[C@@H](CO[P](O)(=O)O[P](O)(=O)[C@@](F)(Cl)[P](O)(O)=O)O3" GFC SMILES CACTVS 3.352 "NC1=Nc2n(cnc2C(=O)N1)[CH]3C[CH](O)[CH](CO[P](O)(=O)O[P](O)(=O)[C](F)(Cl)[P](O)(O)=O)O3" GFC SMILES_CANONICAL "OpenEye OEToolkits" 1.7.0 "c1nc2c(n1[C@H]3C[C@@H]([C@H](O3)CO[P@](=O)(O)O[P@](=O)([C@](F)(P(=O)(O)O)Cl)O)O)N=C(NC2=O)N" GFC SMILES "OpenEye OEToolkits" 1.7.0 "c1nc2c(n1C3CC(C(O3)COP(=O)(O)OP(=O)(C(F)(P(=O)(O)O)Cl)O)O)N=C(NC2=O)N" GFC InChI InChI 1.03 "InChI=1S/C11H16ClFN5O12P3/c12-11(13,31(21,22)23)32(24,25)30-33(26,27)28-2-5-4(19)1-6(29-5)18-3-15-7-8(18)16-10(14)17-9(7)20/h3-6,19H,1-2H2,(H,24,25)(H,26,27)(H2,21,22,23)(H3,14,16,17,20)/t4-,5+,6+,11+/m0/s1" GFC InChIKey InChI 1.03 YYWHXOYNXRQZKR-XUSYNCDOSA-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 GFC "SYSTEMATIC NAME" ACDLabs 11.02 "5'-O-[(S)-{[(S)-[(S)-chloro(fluoro)phosphonomethyl](hydroxy)phosphoryl]oxy}(hydroxy)phosphoryl]-2'-deoxyguanosine" GFC "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.6.1 "[(S)-[[[(2R,3S,5R)-5-(2-azanyl-6-oxo-1H-purin-9-yl)-3-hydroxy-oxolan-2-yl]methoxy-hydroxy-phosphoryl]oxy-hydroxy-phosphoryl]-chloro-fluoro-methyl]phosphonic acid" # loop_ _pdbx_chem_comp_audit.comp_id _pdbx_chem_comp_audit.action_type _pdbx_chem_comp_audit.date _pdbx_chem_comp_audit.processing_site GFC "Create component" 2009-09-14 RCSB GFC "Modify descriptor" 2011-06-04 RCSB #