data_XGA # _chem_comp.id XGA _chem_comp.name "6-AMINO-3-(2-DEOXY-5-O-PHOSPHONO-BETA-D-ERYTHRO-PENTOFURANOSYL)-3,7-DIHYDRO-8H-IMIDAZO[4,5-G]QUINAZOLIN-8-ONE" _chem_comp.type "DNA LINKING" _chem_comp.pdbx_type ATOMN _chem_comp.formula "C14 H16 N5 O7 P" _chem_comp.mon_nstd_parent_comp_id ? _chem_comp.pdbx_synonyms ? _chem_comp.pdbx_formal_charge 0 _chem_comp.pdbx_initial_date 2006-09-26 _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 397.280 _chem_comp.one_letter_code N _chem_comp.three_letter_code XGA _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 2ICZ _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 XGA P P P 0 1 N N N 5.030 -5.869 6.802 1.592 -1.245 -4.964 P XGA 1 XGA OP1 O1P O 0 1 N N N 5.861 -7.087 6.937 0.339 -0.227 -4.868 OP1 XGA 2 XGA OP2 O2P O 0 1 N N N 4.191 -5.420 7.937 2.575 -0.951 -6.059 OP2 XGA 3 XGA "C5'" "C5'" C 0 1 N N N 6.388 -4.478 5.011 1.348 -1.500 -2.377 "C5'" XGA 4 XGA "O5'" "O5'" O 0 1 N N N 5.989 -4.650 6.375 2.211 -1.232 -3.468 "O5'" XGA 5 XGA "C4'" "C4'" C 0 1 N N R 6.965 -3.087 4.767 2.156 -1.432 -1.088 "C4'" XGA 6 XGA "O4'" "O4'" O 0 1 N N N 5.929 -2.236 4.255 2.678 -0.093 -0.958 "O4'" XGA 7 XGA "C3'" "C3'" C 0 1 N N S 7.491 -2.384 6.018 1.309 -1.697 0.152 "C3'" XGA 8 XGA "C2'" "C2'" C 0 1 N N N 6.378 -1.423 6.406 0.878 -0.312 0.578 "C2'" XGA 9 XGA "C1'" "C1'" C 0 1 N N R 5.798 -1.054 5.047 2.101 0.516 0.211 "C1'" XGA 10 XGA N9 N9 N 0 1 Y N N 4.404 -0.640 5.091 1.818 1.923 -0.049 N9 XGA 11 XGA C8 C8 C 0 1 Y N N 3.478 -0.972 6.051 1.434 2.448 -1.251 C8 XGA 12 XGA N7 N7 N 0 1 Y N N 2.304 -0.443 5.806 1.250 3.747 -1.183 N7 XGA 13 XGA C4 C4 C 0 1 Y N N 3.269 1.555 2.260 2.192 4.238 2.851 C4 XGA 14 XGA C5 C5 C 0 1 Y N N 1.942 1.675 2.724 1.832 5.384 2.125 C5 XGA 15 XGA N3 N3 N 0 1 N N N 3.691 2.149 1.137 2.529 4.287 4.217 N3 XGA 16 XGA C2 C2 C 0 1 N N N 2.785 2.881 0.451 2.506 5.436 4.830 C2 XGA 17 XGA N2 N2 N 0 1 N N N 3.190 3.484 -0.692 2.820 5.570 6.156 N2 XGA 18 XGA N1 N1 N 0 1 N N N 1.501 3.047 0.825 2.158 6.608 4.171 N1 XGA 19 XGA C6 C6 C 0 1 N N N 1.043 2.443 1.980 1.809 6.682 2.832 C6 XGA 20 XGA O6 O6 O 0 1 N N N -0.131 2.578 2.325 1.502 7.720 2.259 O6 XGA 21 XGA C10 C10 C 0 1 Y N N 3.770 0.160 4.166 1.887 2.952 0.855 C10 XGA 22 XGA C11 C11 C 0 1 Y N N 2.464 0.262 4.643 1.528 4.079 0.123 C11 XGA 23 XGA CP CP C 0 1 Y N N 1.535 1.025 3.921 1.496 5.330 0.762 CP XGA 24 XGA CD CD C 0 1 Y N N 4.189 0.796 2.982 2.223 2.990 2.209 CD XGA 25 XGA "O3'" "O3'" O 0 1 N N N 8.609 -1.590 5.614 2.127 -2.250 1.180 "O3'" XGA 26 XGA OP3 O3P O 0 1 N Y N 4.085 -6.043 5.509 0.886 -2.697 -5.051 OP3 XGA 27 XGA HO1P HO1P H 0 0 N N N 6.039 -7.447 6.076 -0.163 -0.014 -5.684 HO1P XGA 28 XGA HO3P HO3P H 0 0 N N N 3.176 -6.077 5.783 0.508 -2.990 -5.907 HO3P XGA 29 XGA "H5'1" "1H5'" H 0 0 N N N 5.508 -4.615 4.365 0.551 -0.756 -2.359 "H5'1" XGA 30 XGA "H5'2" "2H5'" H 0 0 N N N 7.167 -5.220 4.782 0.917 -2.495 -2.497 "H5'2" XGA 31 XGA "H4'" "H4'" H 0 1 N N N 7.806 -3.244 4.075 3.008 -2.117 -1.157 "H4'" XGA 32 XGA "H3'" "H3'" H 0 1 N N N 7.771 -3.077 6.825 0.475 -2.383 -0.018 "H3'" XGA 33 XGA "H2'1" "1H2'" H 0 0 N N N 6.759 -0.544 6.946 0.008 0.008 -0.009 "H2'1" XGA 34 XGA "H2'2" "2H2'" H 0 0 N N N 5.641 -1.855 7.099 0.635 -0.225 1.641 "H2'2" XGA 35 XGA "H1'" "H1'" H 0 1 N N N 6.336 -0.185 4.639 2.853 0.503 1.007 "H1'" XGA 36 XGA H8 H8 H 0 1 N N N 3.692 -1.595 6.906 1.306 1.839 -2.136 H8 XGA 37 XGA HN21 1HN2 H 0 0 N N N 2.425 3.985 -1.097 3.442 6.298 6.422 HN21 XGA 38 XGA HN22 2HN2 H 0 0 N N N 4.113 3.436 -1.073 2.413 4.935 6.804 HN22 XGA 39 XGA HN1 HN1 H 0 1 N N N 0.883 3.604 0.270 2.160 7.471 4.707 HN1 XGA 40 XGA HP HP H 0 1 N N N 0.518 1.118 4.272 1.218 6.218 0.205 HP XGA 41 XGA HD HD H 0 1 N N N 5.208 0.697 2.638 2.498 2.088 2.747 HD XGA 42 XGA "HO3'" H3T H 0 0 N Y N 8.553 -1.414 4.682 1.537 -2.451 1.923 "HO3'" XGA 43 # 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 XGA P OP3 SING N N 1 XGA P "O5'" SING N N 2 XGA P OP1 SING N N 3 XGA P OP2 DOUB N N 4 XGA OP1 HO1P SING N N 5 XGA "C5'" "C4'" SING N N 6 XGA "C5'" "O5'" SING N N 7 XGA "C5'" "H5'1" SING N N 8 XGA "C5'" "H5'2" SING N N 9 XGA "C4'" "O4'" SING N N 10 XGA "C4'" "C3'" SING N N 11 XGA "C4'" "H4'" SING N N 12 XGA "O4'" "C1'" SING N N 13 XGA "C3'" "O3'" SING N N 14 XGA "C3'" "C2'" SING N N 15 XGA "C3'" "H3'" SING N N 16 XGA "C2'" "C1'" SING N N 17 XGA "C2'" "H2'1" SING N N 18 XGA "C2'" "H2'2" SING N N 19 XGA "C1'" N9 SING N N 20 XGA "C1'" "H1'" SING N N 21 XGA N9 C10 SING Y N 22 XGA N9 C8 SING Y N 23 XGA C8 N7 DOUB Y N 24 XGA C8 H8 SING N N 25 XGA N7 C11 SING Y N 26 XGA C4 N3 SING N N 27 XGA C4 C5 DOUB Y N 28 XGA C4 CD SING Y N 29 XGA C5 C6 SING N N 30 XGA C5 CP SING Y N 31 XGA N3 C2 DOUB N N 32 XGA C2 N2 SING N N 33 XGA C2 N1 SING N N 34 XGA N2 HN21 SING N N 35 XGA N2 HN22 SING N N 36 XGA N1 C6 SING N N 37 XGA N1 HN1 SING N N 38 XGA C6 O6 DOUB N N 39 XGA C10 CD DOUB Y N 40 XGA C10 C11 SING Y N 41 XGA C11 CP DOUB Y N 42 XGA CP HP SING N N 43 XGA CD HD SING N N 44 XGA "O3'" "HO3'" SING N N 45 XGA OP3 HO3P SING N N 46 # 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 XGA SMILES ACDLabs 10.04 "O=C2c3cc1ncn(c1cc3N=C(N)N2)C4OC(C(O)C4)COP(=O)(O)O" XGA SMILES_CANONICAL CACTVS 3.341 "NC1=Nc2cc3n(cnc3cc2C(=O)N1)[C@H]4C[C@H](O)[C@@H](CO[P](O)(O)=O)O4" XGA SMILES CACTVS 3.341 "NC1=Nc2cc3n(cnc3cc2C(=O)N1)[CH]4C[CH](O)[CH](CO[P](O)(O)=O)O4" XGA SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 "c1c2c(cc3c1ncn3[C@H]4C[C@@H]([C@H](O4)COP(=O)(O)O)O)N=C(NC2=O)N" XGA SMILES "OpenEye OEToolkits" 1.5.0 "c1c2c(cc3c1ncn3C4CC(C(O4)COP(=O)(O)O)O)N=C(NC2=O)N" XGA InChI InChI 1.03 "InChI=1S/C14H16N5O7P/c15-14-17-7-2-9-8(1-6(7)13(21)18-14)16-5-19(9)12-3-10(20)11(26-12)4-25-27(22,23)24/h1-2,5,10-12,20H,3-4H2,(H2,22,23,24)(H3,15,17,18,21)/t10-,11+,12+/m0/s1" XGA InChIKey InChI 1.03 WZVWDCOJGSHXAJ-QJPTWQEYSA-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 XGA "SYSTEMATIC NAME" ACDLabs 10.04 "6-amino-3-(2-deoxy-5-O-phosphono-beta-D-erythro-pentofuranosyl)-3,7-dihydro-8H-imidazo[4,5-g]quinazolin-8-one" XGA "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "[(2R,3S,5R)-5-(6-amino-8-oxo-7H-pyrimido[5,4-f]benzimidazol-3-yl)-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 XGA "Create component" 2006-09-26 RCSB XGA "Modify descriptor" 2011-06-04 RCSB #