data_GCK # _chem_comp.id GCK _chem_comp.name ;PHOSPHORIC ACID 9-(2-GUANIDINOETHOXY-3-(2-DEOXY-BETA-D-ERYTHROPENTOFURANOSYL))-3H-PYRIMIDO-[5,4-B][1,4]-BENZOOXAZIN-2-ONE]-5'-ESTER ; _chem_comp.type "DNA LINKING" _chem_comp.pdbx_type ATOMN _chem_comp.formula "C18 H24 N6 O9 P" _chem_comp.mon_nstd_parent_comp_id DC _chem_comp.pdbx_synonyms ? _chem_comp.pdbx_formal_charge 1 _chem_comp.pdbx_initial_date 2001-12-07 _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 499.392 _chem_comp.one_letter_code C _chem_comp.three_letter_code GCK _chem_comp.pdbx_model_coordinates_details ? _chem_comp.pdbx_model_coordinates_missing_flag N _chem_comp.pdbx_ideal_coordinates_details "OpenEye OEToolkits" _chem_comp.pdbx_ideal_coordinates_missing_flag N _chem_comp.pdbx_model_coordinates_db_code 1KGK _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 GCK P P P 0 1 N N N 7.662 -5.129 20.482 -4.060 -1.522 2.845 P GCK 1 GCK O1P O1P O 0 1 N N N 6.944 -6.421 20.811 -4.581 -2.443 3.910 O1P GCK 2 GCK O2P O2P O 0 1 N N N 7.615 -4.555 19.136 -3.944 -2.170 1.368 O2P GCK 3 GCK "O5'" O5* O 0 1 N N N 7.085 -4.026 21.449 -2.581 -0.926 3.121 "O5'" GCK 4 GCK N1 N1 N 0 1 N N N 7.515 -0.140 22.319 1.164 -2.047 0.989 N1 GCK 5 GCK C6 C6 C 0 1 N N N 7.976 -0.856 21.258 -0.007 -2.763 0.884 C6 GCK 6 GCK C2 C2 C 0 1 N N N 7.583 1.244 22.321 2.366 -2.541 0.452 C2 GCK 7 GCK O2 O2 O 0 1 N N N 7.135 1.839 23.285 3.421 -1.911 0.541 O2 GCK 8 GCK N3 N3 N 0 1 N N N 8.146 1.895 21.267 2.341 -3.769 -0.187 N3 GCK 9 GCK C4 C4 C 0 1 N N N 8.602 1.190 20.231 1.231 -4.450 -0.288 C4 GCK 10 GCK N4 N4 N 0 1 N N N 9.182 1.829 19.206 1.209 -5.672 -0.924 N4 GCK 11 GCK C5 C5 C 0 1 N N N 8.529 -0.237 20.192 -0.055 -3.947 0.274 C5 GCK 12 GCK O8 O8 O 0 1 N N N 8.965 -0.986 19.126 -1.223 -4.678 0.160 O8 GCK 13 GCK C9 C9 C 0 1 Y N N 9.567 -0.316 18.129 -1.168 -5.893 -0.490 C9 GCK 14 GCK C10 C10 C 0 1 Y N N 10.066 -1.079 17.074 -2.363 -6.608 -0.590 C10 GCK 15 GCK C11 C11 C 0 1 Y N N 10.646 -0.423 16.002 -2.377 -7.843 -1.236 C11 GCK 16 GCK C12 C12 C 0 1 Y N N 10.763 0.970 15.962 -1.201 -8.360 -1.779 C12 GCK 17 GCK C13 C13 C 0 1 Y N N 10.294 1.738 17.017 -0.007 -7.644 -1.679 C13 GCK 18 GCK C14 C14 C 0 1 Y N N 9.693 1.065 18.098 0.021 -6.403 -1.033 C14 GCK 19 GCK O15 O15 O 0 1 N N N 10.353 3.103 17.152 1.128 -8.172 -2.219 O15 GCK 20 GCK C16 C16 C 0 1 N N N 11.703 3.674 16.653 0.971 -9.014 -3.359 C16 GCK 21 GCK C17 C17 C 0 1 N N N 12.166 4.717 17.565 2.206 -8.913 -4.234 C17 GCK 22 GCK N18 N18 N 0 1 N N N 11.234 5.796 17.729 2.367 -7.519 -4.708 N18 GCK 23 GCK C19 C19 C 0 1 N N N 11.338 6.980 17.077 3.419 -7.146 -5.529 C19 GCK 24 GCK N20 N20 N 0 1 N N N 10.525 7.939 17.305 3.581 -5.841 -5.982 N20 GCK 25 GCK N21 N21 N 1 1 N N N 12.256 7.117 16.064 4.341 -8.115 -5.910 N21 GCK 26 GCK "C2'" C2* C 0 1 N N N 5.471 -0.906 23.595 0.790 0.372 0.733 "C2'" GCK 27 GCK "C5'" C5* C 0 1 N N N 6.840 -4.327 22.834 -2.017 -0.048 2.160 "C5'" GCK 28 GCK "C4'" C4* C 0 1 N N R 6.409 -3.052 23.558 -0.634 0.377 2.635 "C4'" GCK 29 GCK "O4'" O4* O 0 1 N N N 7.538 -2.150 23.588 0.189 -0.803 2.715 "O4'" GCK 30 GCK "C1'" C1* C 0 1 N N R 6.827 -0.764 23.554 1.157 -0.778 1.657 "C1'" GCK 31 GCK "C3'" C3* C 0 1 N N S 5.266 -2.244 22.953 0.064 1.317 1.662 "C3'" GCK 32 GCK "O3'" O3* O 0 1 N N N 3.958 -2.848 23.212 1.008 2.125 2.360 "O3'" GCK 33 GCK O3P O3P O 0 1 N Y N 9.117 -5.348 20.931 -4.945 -0.191 2.600 O3P GCK 34 GCK HOP2 2HOP H 0 0 N N N 8.065 -3.744 18.930 -4.712 -2.660 1.004 HOP2 GCK 35 GCK H6 H6 H 0 1 N N N 7.910 -1.784 21.266 -0.892 -2.316 1.324 H6 GCK 36 GCK H4 H4 H 0 1 N N N 9.249 2.687 19.210 2.053 -6.066 -1.323 H4 GCK 37 GCK H10 H10 H 0 1 N N N 10.011 -2.007 17.090 -3.282 -6.209 -0.169 H10 GCK 38 GCK H11 H11 H 0 1 N N N 10.967 -0.924 15.287 -3.304 -8.403 -1.316 H11 GCK 39 GCK H12 H12 H 0 1 N N N 11.156 1.381 15.227 -1.221 -9.324 -2.282 H12 GCK 40 GCK H161 1H16 H 0 0 N N N 12.362 2.963 16.607 0.846 -10.042 -3.004 H161 GCK 41 GCK H162 2H16 H 0 0 N N N 11.593 4.043 15.763 0.068 -8.710 -3.899 H162 GCK 42 GCK H171 1H17 H 0 0 N N N 12.340 4.319 18.432 3.109 -9.193 -3.682 H171 GCK 43 GCK H172 2H17 H 0 0 N N N 13.004 5.075 17.231 2.107 -9.562 -5.110 H172 GCK 44 GCK H18 H18 H 0 1 N N N 10.574 5.685 18.269 1.689 -6.830 -4.421 H18 GCK 45 GCK H201 1H20 H 0 0 N N N 9.895 7.840 17.882 4.361 -5.590 -6.585 H201 GCK 46 GCK H202 2H20 H 0 0 N N N 10.608 8.682 16.881 2.934 -5.099 -5.727 H202 GCK 47 GCK H211 1H21 H 0 0 N N N 12.276 7.839 15.597 4.252 -9.079 -5.597 H211 GCK 48 GCK H212 2H21 H 0 0 N N N 12.811 6.481 15.897 5.128 -7.886 -6.512 H212 GCK 49 GCK "H2'1" 1H2* H 0 0 N N N 5.028 -0.204 23.093 0.107 0.030 -0.055 "H2'1" GCK 50 GCK "H2'2" 2H2* H 0 0 N N N 5.143 -0.900 24.508 1.674 0.806 0.256 "H2'2" GCK 51 GCK "H5'1" 1H5* H 0 0 N N N 7.646 -4.680 23.242 -1.946 -0.568 1.202 "H5'1" GCK 52 GCK "H5'2" 2H5* H 0 0 N N N 6.143 -4.997 22.906 -2.666 0.824 2.052 "H5'2" GCK 53 GCK "H4'" H4* H 0 1 N N N 6.172 -3.284 24.480 -0.708 0.804 3.640 "H4'" GCK 54 GCK "H1'" H1* H 0 1 N N N 7.105 -0.259 24.347 2.145 -0.631 2.106 "H1'" GCK 55 GCK "H3'" H3* H 0 1 N N N 5.400 -2.165 21.985 -0.622 1.992 1.141 "H3'" GCK 56 GCK H3T H3T H 0 1 N Y N 3.828 -3.696 22.805 0.752 3.054 2.222 H3T GCK 57 GCK HOP3 3HOP H 0 0 N N N 9.681 -5.393 20.168 -5.917 -0.279 2.499 HOP3 GCK 58 # 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 GCK P O1P DOUB N N 1 GCK P O2P SING N N 2 GCK P "O5'" SING N N 3 GCK P O3P SING N N 4 GCK O2P HOP2 SING N N 5 GCK "O5'" "C5'" SING N N 6 GCK N1 C6 SING N N 7 GCK N1 C2 SING N N 8 GCK N1 "C1'" SING N N 9 GCK C6 C5 DOUB N N 10 GCK C6 H6 SING N N 11 GCK C2 O2 DOUB N N 12 GCK C2 N3 SING N N 13 GCK N3 C4 DOUB N N 14 GCK C4 N4 SING N N 15 GCK C4 C5 SING N N 16 GCK N4 C14 SING N N 17 GCK N4 H4 SING N N 18 GCK C5 O8 SING N N 19 GCK O8 C9 SING N N 20 GCK C9 C10 DOUB Y N 21 GCK C9 C14 SING Y N 22 GCK C10 C11 SING Y N 23 GCK C10 H10 SING N N 24 GCK C11 C12 DOUB Y N 25 GCK C11 H11 SING N N 26 GCK C12 C13 SING Y N 27 GCK C12 H12 SING N N 28 GCK C13 C14 DOUB Y N 29 GCK C13 O15 SING N N 30 GCK O15 C16 SING N N 31 GCK C16 C17 SING N N 32 GCK C16 H161 SING N N 33 GCK C16 H162 SING N N 34 GCK C17 N18 SING N N 35 GCK C17 H171 SING N N 36 GCK C17 H172 SING N N 37 GCK N18 C19 SING N N 38 GCK N18 H18 SING N N 39 GCK C19 N20 SING N N 40 GCK C19 N21 DOUB N N 41 GCK N20 H201 SING N N 42 GCK N20 H202 SING N N 43 GCK N21 H211 SING N N 44 GCK N21 H212 SING N N 45 GCK "C2'" "C1'" SING N N 46 GCK "C2'" "C3'" SING N N 47 GCK "C2'" "H2'1" SING N N 48 GCK "C2'" "H2'2" SING N N 49 GCK "C5'" "C4'" SING N N 50 GCK "C5'" "H5'1" SING N N 51 GCK "C5'" "H5'2" SING N N 52 GCK "C4'" "O4'" SING N N 53 GCK "C4'" "C3'" SING N N 54 GCK "C4'" "H4'" SING N N 55 GCK "O4'" "C1'" SING N N 56 GCK "C1'" "H1'" SING N N 57 GCK "C3'" "O3'" SING N N 58 GCK "C3'" "H3'" SING N N 59 GCK "O3'" H3T SING N N 60 GCK O3P HOP3 SING N N 61 # 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 GCK SMILES ACDLabs 10.04 "O=C3N=C2C(Oc1cccc(OCCNC(=[NH2+])\N)c1N2)=CN3C4OC(C(O)C4)COP(=O)(O)O" GCK SMILES_CANONICAL CACTVS 3.341 "NC(=[NH2+])NCCOc1cccc2OC3=CN([C@H]4C[C@H](O)[C@@H](CO[P](O)(O)=O)O4)C(=O)N=C3Nc12" GCK SMILES CACTVS 3.341 "NC(=[NH2+])NCCOc1cccc2OC3=CN([CH]4C[CH](O)[CH](CO[P](O)(O)=O)O4)C(=O)N=C3Nc12" GCK SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 "c1cc2c(c(c1)OCCNC(=[NH2+])N)NC3=NC(=O)N(C=C3O2)[C@H]4C[C@@H]([C@H](O4)COP(=O)(O)O)O" GCK SMILES "OpenEye OEToolkits" 1.5.0 "c1cc2c(c(c1)OCCNC(=[NH2+])N)NC3=NC(=O)N(C=C3O2)C4CC(C(O4)COP(=O)(O)O)O" GCK InChI InChI 1.03 "InChI=1S/C18H23N6O9P/c19-17(20)21-4-5-30-10-2-1-3-11-15(10)22-16-12(32-11)7-24(18(26)23-16)14-6-9(25)13(33-14)8-31-34(27,28)29/h1-3,7,9,13-14,25H,4-6,8H2,(H4,19,20,21)(H,22,23,26)(H2,27,28,29)/p+1/t9-,13+,14+/m0/s1" GCK InChIKey InChI 1.03 GCBWWBGDWVGEAS-CUOATXAZSA-O # 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 GCK "SYSTEMATIC NAME" ACDLabs 10.04 "9-(2-{[amino(iminio)methyl]amino}ethoxy)-3-(2-deoxy-5-O-phosphono-beta-D-erythro-pentofuranosyl)-3H-pyrimido[5,4-b][1,4]benzoxazin-2(10H)-one" GCK "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "[amino-[2-[[3-[(2R,4S,5R)-4-hydroxy-5-(phosphonooxymethyl)oxolan-2-yl]-2-oxo-10H-pyrimido[5,4-b][1,4]benzoxazin-9-yl]oxy]ethylamino]methylidene]azanium" # loop_ _pdbx_chem_comp_audit.comp_id _pdbx_chem_comp_audit.action_type _pdbx_chem_comp_audit.date _pdbx_chem_comp_audit.processing_site GCK "Create component" 2001-12-07 RCSB GCK "Modify descriptor" 2011-06-04 RCSB #