data_GNP # _chem_comp.id GNP _chem_comp.name "PHOSPHOAMINOPHOSPHONIC ACID-GUANYLATE ESTER" _chem_comp.type NON-POLYMER _chem_comp.pdbx_type HETAIN _chem_comp.formula "C10 H17 N6 O13 P3" _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 GTN _chem_comp.formula_weight 522.196 _chem_comp.one_letter_code ? _chem_comp.three_letter_code GNP _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 1CTQ _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 GNP PG PG P 0 1 N N N 4.935 31.507 21.691 -1.231 -0.295 7.212 PG GNP 1 GNP O1G O1G O 0 1 N N N 4.899 32.144 23.047 -1.759 1.078 7.063 O1G GNP 2 GNP O2G O2G O 0 1 N N N 4.129 32.343 20.710 -2.158 -1.118 8.240 O2G GNP 3 GNP O3G O3G O 0 1 N N N 4.556 30.076 21.650 0.274 -0.234 7.778 O3G GNP 4 GNP N3B N3B N 0 1 N N N 6.611 31.682 21.302 -1.236 -1.064 5.714 N3B GNP 5 GNP PB PB P 0 1 N N R 7.202 31.350 19.762 -0.252 -0.151 4.699 PB GNP 6 GNP O1B O1B O 0 1 N N N 7.408 29.908 19.616 -0.795 1.221 4.589 O1B GNP 7 GNP O2B O2B O 0 1 N N N 6.425 32.127 18.752 1.237 -0.091 5.307 O2B GNP 8 GNP O3A O3A O 0 1 N N N 8.690 32.006 19.856 -0.209 -0.830 3.240 O3A GNP 9 GNP PA PA P 0 1 N N S 9.197 33.390 19.367 0.744 0.089 2.326 PA GNP 10 GNP O1A O1A O 0 1 N N N 9.236 33.433 17.890 0.185 1.458 2.252 O1A GNP 11 GNP O2A O2A O 0 1 N N N 8.532 34.468 20.185 2.216 0.145 2.974 O2A GNP 12 GNP "O5'" O5* O 0 1 N N N 10.648 33.354 19.815 0.832 -0.534 0.845 "O5'" GNP 13 GNP "C5'" C5* C 0 1 N N N 11.013 33.228 21.198 1.688 0.322 0.086 "C5'" GNP 14 GNP "C4'" C4* C 0 1 N N R 12.433 33.663 21.389 1.815 -0.217 -1.339 "C4'" GNP 15 GNP "O4'" O4* O 0 1 N N N 13.401 32.943 20.714 0.524 -0.237 -1.986 "O4'" GNP 16 GNP "C3'" C3* C 0 1 N N S 12.657 35.142 20.956 2.674 0.734 -2.202 "C3'" GNP 17 GNP "O3'" O3* O 0 1 N N N 13.626 35.786 21.804 4.018 0.258 -2.285 "O3'" GNP 18 GNP "C2'" C2* C 0 1 N N R 13.257 34.966 19.546 1.997 0.695 -3.592 "C2'" GNP 19 GNP "O2'" O2* O 0 1 N N N 14.067 36.035 19.166 2.904 0.196 -4.577 "O2'" GNP 20 GNP "C1'" C1* C 0 1 N N R 14.116 33.758 19.817 0.808 -0.272 -3.402 "C1'" GNP 21 GNP N9 N9 N 0 1 Y N N 14.351 32.999 18.572 -0.352 0.188 -4.166 N9 GNP 22 GNP C8 C8 C 0 1 Y N N 13.285 32.569 17.679 -1.315 1.051 -3.730 C8 GNP 23 GNP N7 N7 N 0 1 Y N N 13.785 31.834 16.715 -2.196 1.240 -4.668 N7 GNP 24 GNP C5 C5 C 0 1 Y N N 15.262 31.974 16.869 -1.853 0.512 -5.759 C5 GNP 25 GNP C6 C6 C 0 1 Y N N 16.309 31.355 16.084 -2.423 0.330 -7.041 C6 GNP 26 GNP O6 O6 O 0 1 N N N 16.242 30.767 15.067 -3.453 0.902 -7.354 O6 GNP 27 GNP N1 N1 N 0 1 Y N N 17.523 31.709 16.581 -1.794 -0.489 -7.912 N1 GNP 28 GNP C2 C2 C 0 1 Y N N 17.576 32.330 17.793 -0.646 -1.129 -7.549 C2 GNP 29 GNP N2 N2 N 0 1 N N N 18.953 32.527 18.141 -0.033 -1.960 -8.453 N2 GNP 30 GNP N3 N3 N 0 1 Y N N 16.717 32.788 18.612 -0.107 -0.968 -6.361 N3 GNP 31 GNP C4 C4 C 0 1 Y N N 15.526 32.598 18.035 -0.670 -0.168 -5.449 C4 GNP 32 GNP HOG2 2HOG H 0 0 N N N 4.151 31.939 19.850 -2.127 -0.645 9.083 HOG2 GNP 33 GNP HOG3 3HOG H 0 0 N N N 4.578 29.672 20.790 0.579 -1.147 7.860 HOG3 GNP 34 GNP HNB3 3HNB H 0 0 N N N 7.146 31.125 21.968 -2.175 -0.988 5.353 HNB3 GNP 35 GNP HOB2 2HOB H 0 0 N N N 6.758 31.939 17.882 1.553 -1.004 5.362 HOB2 GNP 36 GNP HOA2 2HOA H 0 0 N N N 8.842 35.314 19.885 2.543 -0.764 3.004 HOA2 GNP 37 GNP "H5'2" 2H5* H 0 0 N N N 10.312 33.778 21.868 1.265 1.326 0.058 "H5'2" GNP 38 GNP "H5'1" 1H5* H 0 0 N N N 10.833 32.198 21.586 2.673 0.356 0.551 "H5'1" GNP 39 GNP "H4'" H4* H 0 1 N N N 12.560 33.493 22.483 2.251 -1.216 -1.329 "H4'" GNP 40 GNP "H3'" H3* H 0 1 N N N 11.732 35.763 21.003 2.652 1.744 -1.793 "H3'" GNP 41 GNP "HO3'" *HO3 H 0 0 N N N 13.762 36.688 21.539 4.505 0.889 -2.833 "HO3'" GNP 42 GNP "H2'" H2* H 0 1 N N N 12.500 34.887 18.730 1.639 1.686 -3.871 "H2'" GNP 43 GNP "HO2'" *HO2 H 0 0 N N N 14.436 35.926 18.297 3.651 0.810 -4.606 "HO2'" GNP 44 GNP "H1'" H1* H 0 1 N N N 15.102 34.070 20.230 1.087 -1.281 -3.708 "H1'" GNP 45 GNP H8 H8 H 0 1 N N N 12.203 32.779 17.728 -1.341 1.509 -2.752 H8 GNP 46 GNP HN1 HN1 H 0 1 N N N 18.375 31.513 16.056 -2.166 -0.630 -8.797 HN1 GNP 47 GNP HN21 1HN2 H 0 0 N N N 18.992 32.991 19.048 0.786 -2.419 -8.210 HN21 GNP 48 GNP HN22 2HN2 H 0 0 N N N 19.471 33.029 17.420 -0.421 -2.092 -9.332 HN22 GNP 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 GNP PG O1G DOUB N N 1 GNP PG O2G SING N N 2 GNP PG O3G SING N N 3 GNP PG N3B SING N N 4 GNP O2G HOG2 SING N N 5 GNP O3G HOG3 SING N N 6 GNP N3B PB SING N N 7 GNP N3B HNB3 SING N N 8 GNP PB O1B DOUB N N 9 GNP PB O2B SING N N 10 GNP PB O3A SING N N 11 GNP O2B HOB2 SING N N 12 GNP O3A PA SING N N 13 GNP PA O1A DOUB N N 14 GNP PA O2A SING N N 15 GNP PA "O5'" SING N N 16 GNP O2A HOA2 SING N N 17 GNP "O5'" "C5'" SING N N 18 GNP "C5'" "C4'" SING N N 19 GNP "C5'" "H5'2" SING N N 20 GNP "C5'" "H5'1" SING N N 21 GNP "C4'" "O4'" SING N N 22 GNP "C4'" "C3'" SING N N 23 GNP "C4'" "H4'" SING N N 24 GNP "O4'" "C1'" SING N N 25 GNP "C3'" "O3'" SING N N 26 GNP "C3'" "C2'" SING N N 27 GNP "C3'" "H3'" SING N N 28 GNP "O3'" "HO3'" SING N N 29 GNP "C2'" "O2'" SING N N 30 GNP "C2'" "C1'" SING N N 31 GNP "C2'" "H2'" SING N N 32 GNP "O2'" "HO2'" SING N N 33 GNP "C1'" N9 SING N N 34 GNP "C1'" "H1'" SING N N 35 GNP N9 C8 SING Y N 36 GNP N9 C4 SING Y N 37 GNP C8 N7 DOUB Y N 38 GNP C8 H8 SING N N 39 GNP N7 C5 SING Y N 40 GNP C5 C6 SING Y N 41 GNP C5 C4 DOUB Y N 42 GNP C6 O6 DOUB N N 43 GNP C6 N1 SING Y N 44 GNP N1 C2 SING Y N 45 GNP N1 HN1 SING N N 46 GNP C2 N2 SING N N 47 GNP C2 N3 DOUB Y N 48 GNP N2 HN21 SING N N 49 GNP N2 HN22 SING N N 50 GNP N3 C4 SING Y 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 GNP SMILES ACDLabs 10.04 "O=P(O)(O)NP(=O)(O)OP(=O)(O)OCC3OC(n2cnc1c2N=C(N)NC1=O)C(O)C3O" GNP SMILES_CANONICAL CACTVS 3.341 "NC1=Nc2n(cnc2C(=O)N1)[C@@H]3O[C@H](CO[P@@](O)(=O)O[P@@](O)(=O)N[P](O)(O)=O)[C@@H](O)[C@H]3O" GNP SMILES CACTVS 3.341 "NC1=Nc2n(cnc2C(=O)N1)[CH]3O[CH](CO[P](O)(=O)O[P](O)(=O)N[P](O)(O)=O)[CH](O)[CH]3O" GNP SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 "c1nc2c(n1[C@H]3[C@@H]([C@@H]([C@H](O3)CO[P@](=O)(O)O[P@@](=O)(NP(=O)(O)O)O)O)O)N=C(NC2=O)N" GNP SMILES "OpenEye OEToolkits" 1.5.0 "c1nc2c(n1C3C(C(C(O3)COP(=O)(O)OP(=O)(NP(=O)(O)O)O)O)O)N=C(NC2=O)N" GNP InChI InChI 1.03 "InChI=1S/C10H17N6O13P3/c11-10-13-7-4(8(19)14-10)12-2-16(7)9-6(18)5(17)3(28-9)1-27-32(25,26)29-31(23,24)15-30(20,21)22/h2-3,5-6,9,17-18H,1H2,(H,25,26)(H3,11,13,14,19)(H4,15,20,21,22,23,24)/t3-,5-,6-,9-/m1/s1" GNP InChIKey InChI 1.03 UQABYHGXWYXDTK-UUOKFMHZSA-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 GNP "SYSTEMATIC NAME" ACDLabs 10.04 "5'-O-[(S)-hydroxy{[(R)-hydroxy(phosphonoamino)phosphoryl]oxy}phosphoryl]guanosine" GNP "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "[[[[(2R,3S,4R,5R)-5-(2-amino-6-oxo-1H-purin-9-yl)-3,4-dihydroxy-oxolan-2-yl]methoxy-hydroxy-phosphoryl]oxy-hydroxy-phosphoryl]amino]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 GNP "Create component" 1999-07-08 RCSB GNP "Modify descriptor" 2011-06-04 RCSB #