data_SGP # _chem_comp.id SGP _chem_comp.name "GUANOSINE-2',3'-CYCLOPHOSPHOROTHIOATE" _chem_comp.type NON-POLYMER _chem_comp.pdbx_type HETAIN _chem_comp.formula "C10 H12 N5 O6 P S" _chem_comp.mon_nstd_parent_comp_id ? _chem_comp.pdbx_synonyms ? _chem_comp.pdbx_formal_charge 0 _chem_comp.pdbx_initial_date 1999-07-08 _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 361.271 _chem_comp.one_letter_code ? _chem_comp.three_letter_code SGP _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 1RSN _chem_comp.pdbx_subcomponent_list ? _chem_comp.pdbx_processing_site EBI # 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 SGP P P P 0 1 N N S 27.530 3.673 21.963 1.744 -0.007 2.477 P SGP 1 SGP S1P S1P S 0 1 N N N 28.921 3.934 23.364 2.298 1.458 3.485 S1P SGP 2 SGP O1P O1P O 0 1 N N N 27.558 4.683 20.978 2.898 -1.122 2.343 O1P SGP 3 SGP "O5'" O5* O 0 1 N N N 24.001 -0.382 21.146 -4.259 -0.843 2.829 "O5'" SGP 4 SGP "C5'" C5* C 0 1 N N N 24.565 0.215 19.979 -3.096 -0.045 3.057 "C5'" SGP 5 SGP "C4'" C4* C 0 1 N N R 25.387 1.442 20.157 -1.903 -0.662 2.325 "C4'" SGP 6 SGP "O4'" O4* O 0 1 N N N 24.748 2.756 20.066 -2.156 -0.688 0.911 "O4'" SGP 7 SGP "C3'" C3* C 0 1 N N R 26.169 1.614 21.442 -0.643 0.198 2.552 "C3'" SGP 8 SGP "O3'" O3* O 0 1 N N N 27.507 2.339 21.194 0.385 -0.657 3.103 "O3'" SGP 9 SGP "C2'" C2* C 0 1 N N R 25.238 2.475 22.329 -0.196 0.593 1.121 "C2'" SGP 10 SGP "O2'" O2* O 0 1 N N N 26.139 3.501 22.743 1.230 0.465 1.008 "O2'" SGP 11 SGP "C1'" C1* C 0 1 N N R 24.289 3.145 21.331 -0.889 -0.481 0.251 "C1'" SGP 12 SGP N9 N9 N 0 1 Y N N 22.905 3.203 21.365 -1.092 0.011 -1.113 N9 SGP 13 SGP C8 C8 C 0 1 Y N N 22.060 2.624 20.490 -2.170 0.717 -1.564 C8 SGP 14 SGP N7 N7 N 0 1 Y N N 20.781 2.871 20.674 -2.020 0.991 -2.827 N7 SGP 15 SGP C5 C5 C 0 1 Y N N 20.764 3.702 21.787 -0.842 0.479 -3.260 C5 SGP 16 SGP C6 C6 C 0 1 N N N 19.752 4.353 22.505 -0.172 0.469 -4.506 C6 SGP 17 SGP O6 O6 O 0 1 N N N 18.533 4.351 22.324 -0.662 1.007 -5.484 O6 SGP 18 SGP N1 N1 N 0 1 N N N 20.178 5.071 23.594 1.027 -0.148 -4.584 N1 SGP 19 SGP C2 C2 C 0 1 N N N 21.513 5.193 23.944 1.563 -0.751 -3.485 C2 SGP 20 SGP N2 N2 N 0 1 N N N 21.746 5.957 25.030 2.781 -1.374 -3.595 N2 SGP 21 SGP N3 N3 N 0 1 N N N 22.480 4.600 23.310 0.951 -0.748 -2.323 N3 SGP 22 SGP C4 C4 C 0 1 Y N N 22.068 3.907 22.204 -0.237 -0.152 -2.168 C4 SGP 23 SGP HOP1 1HOP H 0 0 N N N 26.894 4.558 20.309 3.089 -1.436 3.237 HOP1 SGP 24 SGP "HO5'" *HO5 H 0 0 N N N 23.476 -1.165 21.032 -4.987 -0.421 3.306 "HO5'" SGP 25 SGP "H5'1" 1H5* H 0 0 N N N 25.160 -0.549 19.427 -2.887 -0.005 4.126 "H5'1" SGP 26 SGP "H5'2" 2H5* H 0 0 N N N 23.753 0.420 19.243 -3.269 0.963 2.683 "H5'2" SGP 27 SGP "H4'" H4* H 0 1 N N N 26.015 1.194 19.270 -1.729 -1.675 2.689 "H4'" SGP 28 SGP "H3'" H3* H 0 1 N N N 26.436 0.637 21.908 -0.840 1.066 3.181 "H3'" SGP 29 SGP "H2'" H2* H 0 1 N N N 24.699 1.947 23.150 -0.525 1.595 0.842 "H2'" SGP 30 SGP "H1'" H1* H 0 1 N N N 24.369 4.198 21.686 -0.306 -1.402 0.242 "H1'" SGP 31 SGP H8 H8 H 0 1 N N N 22.399 1.978 19.662 -3.019 1.005 -0.962 H8 SGP 32 SGP HN1 HN1 H 0 1 N N N 19.472 5.533 24.167 1.505 -0.168 -5.427 HN1 SGP 33 SGP HN21 1HN2 H 0 0 N N N 22.728 6.046 25.287 3.177 -1.805 -2.822 HN21 SGP 34 SGP HN22 2HN2 H 0 0 N N N 21.202 5.617 25.823 3.243 -1.389 -4.448 HN22 SGP 35 # 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 SGP P S1P DOUB N N 1 SGP P O1P SING N N 2 SGP P "O3'" SING N N 3 SGP P "O2'" SING N N 4 SGP O1P HOP1 SING N N 5 SGP "O5'" "C5'" SING N N 6 SGP "O5'" "HO5'" SING N N 7 SGP "C5'" "C4'" SING N N 8 SGP "C5'" "H5'1" SING N N 9 SGP "C5'" "H5'2" SING N N 10 SGP "C4'" "O4'" SING N N 11 SGP "C4'" "C3'" SING N N 12 SGP "C4'" "H4'" SING N N 13 SGP "O4'" "C1'" SING N N 14 SGP "C3'" "O3'" SING N N 15 SGP "C3'" "C2'" SING N N 16 SGP "C3'" "H3'" SING N N 17 SGP "C2'" "O2'" SING N N 18 SGP "C2'" "C1'" SING N N 19 SGP "C2'" "H2'" SING N N 20 SGP "C1'" N9 SING N N 21 SGP "C1'" "H1'" SING N N 22 SGP N9 C8 SING Y N 23 SGP N9 C4 SING Y N 24 SGP C8 N7 DOUB Y N 25 SGP C8 H8 SING N N 26 SGP N7 C5 SING Y N 27 SGP C5 C6 SING N N 28 SGP C5 C4 DOUB Y N 29 SGP C6 O6 DOUB N N 30 SGP C6 N1 SING N N 31 SGP N1 C2 SING N N 32 SGP N1 HN1 SING N N 33 SGP C2 N2 SING N N 34 SGP C2 N3 DOUB N N 35 SGP N2 HN21 SING N N 36 SGP N2 HN22 SING N N 37 SGP N3 C4 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 SGP SMILES ACDLabs 10.04 "S=P1(OC2C(OC(C2O1)CO)n3c4N=C(N)NC(=O)c4nc3)O" SGP SMILES_CANONICAL CACTVS 3.341 "NC1=Nc2n(cnc2C(=O)N1)[C@@H]3O[C@H](CO)[C@H]4O[P@](O)(=S)O[C@@H]34" SGP SMILES CACTVS 3.341 "NC1=Nc2n(cnc2C(=O)N1)[CH]3O[CH](CO)[CH]4O[P](O)(=S)O[CH]34" SGP SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 "c1nc2c(n1[C@H]3[C@H]4[C@@H]([C@H](O3)CO)O[P@](=S)(O4)O)N=C(NC2=O)N" SGP SMILES "OpenEye OEToolkits" 1.5.0 "c1nc2c(n1C3C4C(C(O3)CO)OP(=S)(O4)O)N=C(NC2=O)N" SGP InChI InChI 1.03 "InChI=1S/C10H12N5O6PS/c11-10-13-7-4(8(17)14-10)12-2-15(7)9-6-5(3(1-16)19-9)20-22(18,23)21-6/h2-3,5-6,9,16H,1H2,(H,18,23)(H3,11,13,14,17)/t3-,5-,6-,9-,22+/m1/s1" SGP InChIKey InChI 1.03 QZEROIIFJLCOOE-FHIGPPGSSA-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 SGP "SYSTEMATIC NAME" ACDLabs 10.04 "2-amino-9-[(2S,3aR,4R,6R,6aR)-2-hydroxy-6-(hydroxymethyl)-2-sulfidotetrahydrofuro[3,4-d][1,3,2]dioxaphosphol-4-yl]-1,9-dihydro-6H-purin-6-one" SGP "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "2-amino-9-[(1R,3S,5R,6R,8R)-3-hydroxy-8-(hydroxymethyl)-3-sulfanylidene-2,4,7-trioxa-3$l^{5}-phosphabicyclo[3.3.0]octan-6-yl]-1H-purin-6-one" # loop_ _pdbx_chem_comp_audit.comp_id _pdbx_chem_comp_audit.action_type _pdbx_chem_comp_audit.date _pdbx_chem_comp_audit.processing_site SGP "Create component" 1999-07-08 EBI SGP "Modify descriptor" 2011-06-04 RCSB #