data_GGH # _chem_comp.id GGH _chem_comp.name "2'-DEOXY-5'-O-(HYDROXY{[HYDROXY(PHOSPHONOMETHYL)PHOSPHORYL]OXY}PHOSPHORYL)GUANOSINE" _chem_comp.type NON-POLYMER _chem_comp.pdbx_type HETAIN _chem_comp.formula "C11 H18 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 2006-10-26 _chem_comp.pdbx_modified_date 2011-06-04 _chem_comp.pdbx_ambiguous_flag ? _chem_comp.pdbx_release_status REL _chem_comp.pdbx_replaced_by ? _chem_comp.pdbx_replaces ? _chem_comp.formula_weight 505.208 _chem_comp.one_letter_code ? _chem_comp.three_letter_code GGH _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 2ISP _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 GGH C2 C2 C 0 1 N N N 8.390 8.976 7.484 2.203 4.026 2.765 C2 GGH 1 GGH C4 C4 C 0 1 Y N N 7.540 8.162 9.357 1.882 2.959 0.840 C4 GGH 2 GGH C5 C5 C 0 1 Y N N 8.757 8.037 9.997 1.528 4.070 0.114 C5 GGH 3 GGH C6 C6 C 0 1 N N N 9.936 8.390 9.302 1.494 5.351 0.765 C6 GGH 4 GGH P1 P1 P 0 1 N N R 4.966 5.093 14.656 1.614 -1.239 -4.980 P1 GGH 5 GGH P2 P2 P 0 1 N N R 3.911 2.776 13.678 -0.739 0.188 -6.024 P2 GGH 6 GGH O6 O6 O 0 1 N N N 11.109 8.310 9.687 1.191 6.394 0.200 O6 GGH 7 GGH O1A O1A O 0 1 N N N 3.847 5.038 15.637 0.891 -2.679 -5.122 O1A GGH 8 GGH O2A O2A O 0 1 N N N 6.357 5.249 15.158 2.623 -0.941 -6.051 O2A GGH 9 GGH O3A O3A O 0 1 N N N 4.935 3.868 13.775 0.376 -0.202 -4.926 O3A GGH 10 GGH "O5'" "O5'" O 0 1 N N N 4.663 6.334 13.699 2.205 -1.233 -3.473 "O5'" GGH 11 GGH O1B O1B O 0 1 N N N 3.928 2.304 12.271 -1.514 -0.962 -6.592 O1B GGH 12 GGH O2B O2B O 0 1 N N N 2.615 3.155 14.301 0.082 1.064 -7.105 O2B GGH 13 GGH C3B C3B C 0 1 N N N 4.632 1.271 14.532 -1.742 1.418 -5.162 C3B GGH 14 GGH P3 P3 P 0 1 N N N 4.006 1.089 16.287 -2.852 1.037 -3.787 P3 GGH 15 GGH O1G O1G O 0 1 N N N 3.598 2.450 16.746 -3.717 -0.208 -4.343 O1G GGH 16 GGH O2G O2G O 0 1 N N N 5.058 0.353 17.038 -1.872 0.361 -2.695 O2G GGH 17 GGH O3G O3G O 0 1 N N N 2.800 0.227 16.192 -3.652 2.207 -3.297 O3G GGH 18 GGH "C5'" "C5'" C 0 1 N N N 3.417 6.439 13.007 1.348 -1.500 -2.377 "C5'" GGH 19 GGH "C4'" "C4'" C 0 1 N N R 3.637 6.618 11.523 2.156 -1.432 -1.088 "C4'" GGH 20 GGH "O4'" "O4'" O 0 1 N N N 4.482 7.754 11.249 2.678 -0.093 -0.958 "O4'" GGH 21 GGH "C1'" "C1'" C 0 1 N N R 5.172 7.539 10.013 2.101 0.516 0.211 "C1'" GGH 22 GGH N9 N9 N 0 1 Y N N 6.605 7.695 10.254 1.818 1.923 -0.049 N9 GGH 23 GGH N3 N3 N 0 1 N N N 7.286 8.613 8.114 2.225 2.866 2.144 N3 GGH 24 GGH N2 N2 N 0 1 N N N 8.309 9.506 6.244 2.519 4.145 4.093 N2 GGH 25 GGH N1 N1 N 0 1 N N N 9.654 8.864 8.025 1.853 5.233 2.115 N1 GGH 26 GGH N7 N7 N 0 1 Y N N 8.588 7.549 11.284 1.247 3.767 -1.185 N7 GGH 27 GGH C8 C8 C 0 1 Y N N 7.299 7.365 11.395 1.431 2.463 -1.253 C8 GGH 28 GGH "C2'" "C2'" C 0 1 N N N 4.805 6.124 9.545 0.878 -0.312 0.578 "C2'" GGH 29 GGH "C3'" "C3'" C 0 1 N N S 4.338 5.462 10.828 1.309 -1.697 0.152 "C3'" GGH 30 GGH "O3'" "O3'" O 0 1 N N N 3.414 4.399 10.574 2.127 -2.250 1.180 "O3'" GGH 31 GGH HO1A HO1A H 0 0 N N N 4.199 5.026 16.519 1.442 -3.470 -5.302 HO1A GGH 32 GGH HO2B HO2B H 0 0 N N N 2.727 3.236 15.241 0.689 0.606 -7.725 HO2B GGH 33 GGH H3B1 1H3B H 0 0 N N N 4.346 0.374 13.963 -1.049 2.188 -4.806 H3B1 GGH 34 GGH H3B2 2H3B H 0 0 N N N 5.724 1.393 14.572 -2.365 1.892 -5.929 H3B2 GGH 35 GGH HO1G HO1G H 0 0 N N N 3.511 2.453 17.692 -4.427 -0.584 -3.779 HO1G GGH 36 GGH HO2G HO2G H 0 0 N N N 5.803 0.196 16.469 -2.242 0.091 -1.827 HO2G GGH 37 GGH "H5'1" "1H5'" H 0 0 N N N 2.865 7.308 13.394 0.546 -0.756 -2.367 "H5'1" GGH 38 GGH "H5'2" "2H5'" H 0 0 N N N 2.845 5.513 13.169 0.912 -2.496 -2.504 "H5'2" GGH 39 GGH "H4'" "H4'" H 0 1 N N N 2.611 6.722 11.142 3.008 -2.117 -1.157 "H4'" GGH 40 GGH "H1'" "H1'" H 0 1 N N N 4.891 8.259 9.230 2.853 0.503 1.007 "H1'" GGH 41 GGH HN21 1HN2 H 0 0 N N N 9.229 9.734 5.925 1.921 4.687 4.673 HN21 GGH 42 GGH HN22 2HN2 H 0 0 N N N 7.464 9.648 5.728 3.334 3.684 4.426 HN22 GGH 43 GGH HN1 HN1 H 0 1 N N N 10.427 9.145 7.456 1.862 6.083 2.672 HN1 GGH 44 GGH H8 H8 H 0 1 N N N 6.826 6.992 12.292 1.302 1.855 -2.139 H8 GGH 45 GGH "H2'1" "1H2'" H 0 0 N N N 4.014 6.138 8.781 0.008 0.008 -0.009 "H2'1" GGH 46 GGH "H2'2" "2H2'" H 0 0 N N N 5.640 5.595 9.062 0.635 -0.225 1.641 "H2'2" GGH 47 GGH "H3'" "H3'" H 0 1 N N N 5.152 4.999 11.405 0.475 -2.383 -0.018 "H3'" GGH 48 GGH "HO3'" "HO3'" H 0 0 N N N 3.209 4.372 9.647 2.084 -3.213 1.077 "HO3'" GGH 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 GGH C2 N2 SING N N 1 GGH C2 N1 SING N N 2 GGH C2 N3 DOUB N N 3 GGH C4 N3 SING N N 4 GGH C4 C5 DOUB Y N 5 GGH C4 N9 SING Y N 6 GGH C5 C6 SING N N 7 GGH C5 N7 SING Y N 8 GGH C6 N1 SING N N 9 GGH C6 O6 DOUB N N 10 GGH P1 "O5'" SING N N 11 GGH P1 O3A SING N N 12 GGH P1 O2A DOUB N N 13 GGH P1 O1A SING N N 14 GGH P2 O1B DOUB N N 15 GGH P2 O3A SING N N 16 GGH P2 O2B SING N N 17 GGH P2 C3B SING N N 18 GGH O1A HO1A SING N N 19 GGH "O5'" "C5'" SING N N 20 GGH O2B HO2B SING N N 21 GGH C3B P3 SING N N 22 GGH C3B H3B1 SING N N 23 GGH C3B H3B2 SING N N 24 GGH P3 O3G DOUB N N 25 GGH P3 O1G SING N N 26 GGH P3 O2G SING N N 27 GGH O1G HO1G SING N N 28 GGH O2G HO2G SING N N 29 GGH "C5'" "C4'" SING N N 30 GGH "C5'" "H5'1" SING N N 31 GGH "C5'" "H5'2" SING N N 32 GGH "C4'" "C3'" SING N N 33 GGH "C4'" "O4'" SING N N 34 GGH "C4'" "H4'" SING N N 35 GGH "O4'" "C1'" SING N N 36 GGH "C1'" "C2'" SING N N 37 GGH "C1'" N9 SING N N 38 GGH "C1'" "H1'" SING N N 39 GGH N9 C8 SING Y N 40 GGH N2 HN21 SING N N 41 GGH N2 HN22 SING N N 42 GGH N1 HN1 SING N N 43 GGH N7 C8 DOUB Y N 44 GGH C8 H8 SING N N 45 GGH "C2'" "C3'" SING N N 46 GGH "C2'" "H2'1" SING N N 47 GGH "C2'" "H2'2" SING N N 48 GGH "C3'" "O3'" SING N N 49 GGH "C3'" "H3'" SING N N 50 GGH "O3'" "HO3'" 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 GGH SMILES ACDLabs 10.04 "O=P(O)(O)CP(=O)(O)OP(=O)(O)OCC3OC(n2cnc1c2N=C(N)NC1=O)CC3O" GGH SMILES_CANONICAL CACTVS 3.341 "NC1=Nc2n(cnc2C(=O)N1)[C@H]3C[C@H](O)[C@@H](CO[P@](O)(=O)O[P@@](O)(=O)C[P](O)(O)=O)O3" GGH SMILES CACTVS 3.341 "NC1=Nc2n(cnc2C(=O)N1)[CH]3C[CH](O)[CH](CO[P](O)(=O)O[P](O)(=O)C[P](O)(O)=O)O3" GGH SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 "c1nc2c(n1[C@H]3C[C@@H]([C@H](O3)CO[P@@](=O)(O)O[P@@](=O)(CP(=O)(O)O)O)O)N=C(NC2=O)N" GGH SMILES "OpenEye OEToolkits" 1.5.0 "c1nc2c(n1C3CC(C(O3)COP(=O)(O)OP(=O)(CP(=O)(O)O)O)O)N=C(NC2=O)N" GGH InChI InChI 1.03 "InChI=1S/C11H18N5O12P3/c12-11-14-9-8(10(18)15-11)13-3-16(9)7-1-5(17)6(27-7)2-26-31(24,25)28-30(22,23)4-29(19,20)21/h3,5-7,17H,1-2,4H2,(H,22,23)(H,24,25)(H2,19,20,21)(H3,12,14,15,18)/t5-,6+,7+/m0/s1" GGH InChIKey InChI 1.03 QEUKZZGYDFTBEI-RRKCRQDMSA-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 GGH "SYSTEMATIC NAME" ACDLabs 10.04 "2'-deoxy-5'-O-[(R)-hydroxy{[(R)-hydroxy(phosphonomethyl)phosphoryl]oxy}phosphoryl]guanosine" GGH "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "[[[(2R,3S,5R)-5-(2-amino-6-oxo-1H-purin-9-yl)-3-hydroxy-oxolan-2-yl]methoxy-hydroxy-phosphoryl]oxy-hydroxy-phosphoryl]methylphosphonic 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 GGH "Create component" 2006-10-26 RCSB GGH "Modify descriptor" 2011-06-04 RCSB #