data_GEK # _chem_comp.id GEK _chem_comp.name ;(2S)-4-[{[(2S,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl]methyl}(carboxylatomethyl)sulfonio] -2-ammoniobutanoate ; _chem_comp.type NON-POLYMER _chem_comp.pdbx_type HETAIN _chem_comp.formula "C16 H22 N6 O7 S" _chem_comp.mon_nstd_parent_comp_id ? _chem_comp.pdbx_synonyms CARBOXY-S-ADENOSYLMETHIONINE _chem_comp.pdbx_formal_charge 0 _chem_comp.pdbx_initial_date 2012-08-29 _chem_comp.pdbx_modified_date 2020-06-17 _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 442.447 _chem_comp.one_letter_code ? _chem_comp.three_letter_code GEK _chem_comp.pdbx_model_coordinates_details ? _chem_comp.pdbx_model_coordinates_missing_flag N _chem_comp.pdbx_ideal_coordinates_details Corina _chem_comp.pdbx_ideal_coordinates_missing_flag N _chem_comp.pdbx_model_coordinates_db_code 4GEK _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 GEK C C C 0 1 N N N 14.491 -14.396 -20.054 -6.875 -2.298 0.049 C GEK 1 GEK N N N 1 1 N N N 15.585 -16.484 -19.241 -6.579 -0.072 -0.878 N GEK 2 GEK O O O -1 1 N N N 14.675 -13.258 -20.542 -6.616 -3.486 0.147 O GEK 3 GEK N1 N1 N 0 1 Y N N 24.176 -22.782 -19.495 7.259 -0.987 0.610 N1 GEK 4 GEK C2 C2 C 0 1 Y N N 23.876 -21.493 -19.076 6.767 0.207 0.887 C2 GEK 5 GEK N3 N3 N 0 1 Y N N 23.216 -20.702 -19.969 5.493 0.499 0.731 N3 GEK 6 GEK C4 C4 C 0 1 Y N N 22.912 -21.164 -21.162 4.638 -0.414 0.281 C4 GEK 7 GEK C5 C5 C 0 1 Y N N 23.168 -22.461 -21.548 5.113 -1.699 -0.028 C5 GEK 8 GEK C6 C6 C 0 1 Y N N 23.864 -23.262 -20.690 6.481 -1.963 0.154 C6 GEK 9 GEK N6 N6 N 0 1 N N N 24.262 -24.623 -21.046 7.006 -3.211 -0.134 N6 GEK 10 GEK N7 N7 N 0 1 Y N N 22.801 -22.653 -22.806 4.052 -2.424 -0.459 N7 GEK 11 GEK C8 C8 C 0 1 Y N N 22.155 -21.539 -23.214 2.983 -1.682 -0.434 C8 GEK 12 GEK N9 N9 N 0 1 Y N N 22.250 -20.577 -22.234 3.293 -0.433 0.015 N9 GEK 13 GEK CA CA C 0 1 N N S 15.657 -15.336 -20.228 -5.939 -1.382 -0.696 CA GEK 14 GEK CB CB C 0 1 N N N 15.721 -15.816 -21.685 -4.647 -1.212 0.104 CB GEK 15 GEK SD SD S 1 1 N N S 17.463 -16.878 -23.520 -2.117 -0.182 0.241 SD GEK 16 GEK CE CE C 0 1 N N N 16.082 -17.254 -24.592 -2.588 1.007 1.529 CE GEK 17 GEK CG CG C 0 1 N N N 16.737 -16.956 -21.861 -3.649 -0.384 -0.708 CG GEK 18 GEK CZ CZ C 0 1 N N N 16.417 -17.056 -26.051 -3.115 2.262 0.884 CZ GEK 19 GEK "C1'" "C1'" C 0 1 N N R 21.647 -19.235 -22.173 2.359 0.684 0.184 "C1'" GEK 20 GEK "C2'" "C2'" C 0 1 N N R 21.949 -18.339 -23.338 2.368 1.596 -1.069 "C2'" GEK 21 GEK "O2'" "O2'" O 0 1 N N N 23.234 -17.778 -23.294 3.404 2.577 -0.978 "O2'" GEK 22 GEK "C3'" "C3'" C 0 1 N N S 20.802 -17.361 -23.274 0.971 2.260 -0.998 "C3'" GEK 23 GEK "O3'" "O3'" O 0 1 N N N 21.166 -16.140 -22.627 1.063 3.555 -0.402 "O3'" GEK 24 GEK "C4'" "C4'" C 0 1 N N S 19.723 -18.140 -22.568 0.149 1.312 -0.103 "C4'" GEK 25 GEK "O4'" "O4'" O 0 1 N N N 20.247 -19.452 -22.264 0.998 0.205 0.241 "O4'" GEK 26 GEK "C5'" "C5'" C 0 1 N N N 18.499 -18.363 -23.472 -1.077 0.809 -0.868 "C5'" GEK 27 GEK OXT OXT O 0 1 N N N 13.513 -14.841 -19.444 -7.893 -1.853 0.551 OXT GEK 28 GEK OZ1 OZ1 O 0 1 N N N 15.512 -17.553 -26.884 -3.285 2.303 -0.322 OZ1 GEK 29 GEK OZ2 OZ2 O -1 1 N N N 17.665 -16.688 -26.389 -3.372 3.238 1.569 OZ2 GEK 30 GEK HN HN H 0 1 N N N 16.368 -17.091 -19.377 -5.952 0.541 -1.378 HN GEK 31 GEK HNA HNA H 0 1 N N N 15.602 -16.123 -18.308 -7.431 -0.184 -1.407 HNA GEK 32 GEK H2 H2 H 0 1 N N N 24.151 -21.136 -18.095 7.434 0.971 1.256 H2 GEK 33 GEK HN6 HN6 H 0 1 N N N 24.753 -25.038 -20.280 7.952 -3.381 -0.004 HN6 GEK 34 GEK HN6A HN6A H 0 0 N N N 23.447 -25.165 -21.253 6.428 -3.916 -0.465 HN6A GEK 35 GEK H8 H8 H 0 1 N N N 21.645 -21.422 -24.159 1.996 -2.008 -0.727 H8 GEK 36 GEK HA HA H 0 1 N N N 16.579 -14.773 -20.023 -5.709 -1.812 -1.671 HA GEK 37 GEK HB HB H 0 1 N N N 14.726 -16.175 -21.987 -4.865 -0.700 1.042 HB GEK 38 GEK HBA HBA H 0 1 N N N 16.016 -14.972 -22.326 -4.219 -2.191 0.316 HBA GEK 39 GEK HE HE H 0 1 N N N 15.789 -18.303 -24.436 -3.361 0.570 2.161 HE GEK 40 GEK HEA HEA H 0 1 N N N 15.241 -16.595 -24.330 -1.716 1.248 2.136 HEA GEK 41 GEK HG HG H 0 1 N N N 17.533 -16.855 -21.109 -3.431 -0.895 -1.646 HG GEK 42 GEK HGA HGA H 0 1 N N N 16.228 -17.922 -21.730 -4.077 0.596 -0.919 HGA GEK 43 GEK "H1'" "H1'" H 0 1 N N N 21.914 -18.734 -21.231 2.605 1.257 1.077 "H1'" GEK 44 GEK "H2'" "H2'" H 0 1 N N N 21.840 -18.930 -24.260 2.473 1.006 -1.980 "H2'" GEK 45 GEK "HO2'" "HO2'" H 0 0 N N N 23.364 -17.224 -24.055 3.450 3.172 -1.739 "HO2'" GEK 46 GEK "H3'" "H3'" H 0 1 N N N 20.466 -17.149 -24.300 0.530 2.328 -1.992 "H3'" GEK 47 GEK "HO3'" "HO3'" H 0 0 N N N 20.417 -15.555 -22.609 1.618 4.176 -0.894 "HO3'" GEK 48 GEK "H4'" "H4'" H 0 1 N N N 19.416 -17.616 -21.651 -0.164 1.834 0.801 "H4'" GEK 49 GEK "H5'" "H5'" H 0 1 N N N 17.908 -19.204 -23.079 -0.754 0.194 -1.708 "H5'" GEK 50 GEK "H5'A" "H5'A" H 0 0 N N N 18.840 -18.599 -24.491 -1.649 1.660 -1.238 "H5'A" GEK 51 GEK H22 H22 H 0 1 N N N 14.738 -16.995 -19.386 -6.792 0.326 0.024 H22 GEK 52 # # 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 GEK C O SING N N 1 GEK C CA SING N N 2 GEK C OXT DOUB N N 3 GEK N CA SING N N 4 GEK N HN SING N N 5 GEK N HNA SING N N 6 GEK N1 C2 DOUB Y N 7 GEK N1 C6 SING Y N 8 GEK C2 N3 SING Y N 9 GEK C2 H2 SING N N 10 GEK N3 C4 DOUB Y N 11 GEK C4 C5 SING Y N 12 GEK C4 N9 SING Y N 13 GEK C5 C6 DOUB Y N 14 GEK C5 N7 SING Y N 15 GEK C6 N6 SING N N 16 GEK N6 HN6 SING N N 17 GEK N6 HN6A SING N N 18 GEK N7 C8 DOUB Y N 19 GEK C8 N9 SING Y N 20 GEK C8 H8 SING N N 21 GEK N9 "C1'" SING N N 22 GEK CA CB SING N N 23 GEK CA HA SING N N 24 GEK CB CG SING N N 25 GEK CB HB SING N N 26 GEK CB HBA SING N N 27 GEK SD CE SING N N 28 GEK SD CG SING N N 29 GEK SD "C5'" SING N N 30 GEK CE CZ SING N N 31 GEK CE HE SING N N 32 GEK CE HEA SING N N 33 GEK CG HG SING N N 34 GEK CG HGA SING N N 35 GEK CZ OZ1 DOUB N N 36 GEK CZ OZ2 SING N N 37 GEK "C1'" "C2'" SING N N 38 GEK "C1'" "O4'" SING N N 39 GEK "C1'" "H1'" SING N N 40 GEK "C2'" "O2'" SING N N 41 GEK "C2'" "C3'" SING N N 42 GEK "C2'" "H2'" SING N N 43 GEK "O2'" "HO2'" SING N N 44 GEK "C3'" "O3'" SING N N 45 GEK "C3'" "C4'" SING N N 46 GEK "C3'" "H3'" SING N N 47 GEK "O3'" "HO3'" SING N N 48 GEK "C4'" "O4'" SING N N 49 GEK "C4'" "C5'" SING N N 50 GEK "C4'" "H4'" SING N N 51 GEK "C5'" "H5'" SING N N 52 GEK "C5'" "H5'A" SING N N 53 GEK N H22 SING N N 54 # # 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 GEK SMILES ACDLabs 12.01 "[O-]C(=O)C[S+](CCC(C([O-])=O)[NH3+])CC3OC(n2cnc1c(ncnc12)N)C(O)C3O" GEK InChI InChI 1.03 "InChI=1S/C16H22N6O7S/c17-7(16(27)28)1-2-30(4-9(23)24)3-8-11(25)12(26)15(29-8)22-6-21-10-13(18)19-5-20-14(10)22/h5-8,11-12,15,25-26H,1-4,17H2,(H3-,18,19,20,23,24,27,28)/t7-,8+,11+,12+,15+,30-/m0/s1" GEK InChIKey InChI 1.03 VFFTYSZNZJBRBG-HEOPWLPUSA-N GEK SMILES_CANONICAL CACTVS 3.370 "Nc1ncnc2n(cnc12)[C@@H]3O[C@H](C[S@+](CC[C@H]([NH3+])C([O-])=O)CC([O-])=O)[C@@H](O)[C@H]3O" GEK SMILES CACTVS 3.370 "Nc1ncnc2n(cnc12)[CH]3O[CH](C[S+](CC[CH]([NH3+])C([O-])=O)CC([O-])=O)[CH](O)[CH]3O" GEK SMILES_CANONICAL "OpenEye OEToolkits" 1.7.6 "c1nc(c2c(n1)n(cn2)[C@H]3[C@@H]([C@@H]([C@H](O3)C[S@+](CC[C@@H](C(=O)[O-])[NH3+])CC(=O)[O-])O)O)N" GEK SMILES "OpenEye OEToolkits" 1.7.6 "c1nc(c2c(n1)n(cn2)C3C(C(C(O3)C[S+](CCC(C(=O)[O-])[NH3+])CC(=O)[O-])O)O)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 GEK "SYSTEMATIC NAME" ACDLabs 12.01 "(2S)-4-[{[(2S,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl]methyl}(carboxylatomethyl)sulfonio]-2-ammoniobutanoate " GEK "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.7.6 "(2S)-4-[[(2S,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-bis(oxidanyl)oxolan-2-yl]methyl-(2-oxidanidyl-2-oxidanylidene-ethyl)sulfonio]-2-azaniumyl-butanoate" # # loop_ _pdbx_chem_comp_audit.comp_id _pdbx_chem_comp_audit.action_type _pdbx_chem_comp_audit.date _pdbx_chem_comp_audit.processing_site GEK "Create component" 2012-08-29 RCSB GEK "Other modification" 2012-10-05 RCSB GEK "Modify name" 2013-06-11 RCSB GEK "Modify synonyms" 2020-06-05 PDBE # _pdbx_chem_comp_synonyms.ordinal 1 _pdbx_chem_comp_synonyms.comp_id GEK _pdbx_chem_comp_synonyms.name CARBOXY-S-ADENOSYLMETHIONINE _pdbx_chem_comp_synonyms.provenance ? _pdbx_chem_comp_synonyms.type ? ##