data_G20 # _chem_comp.id G20 _chem_comp.name "5-N-acetyl-4-guanidino-6-methyl(propyl) carboxamide-4,5-dihydro-2H-pyran-2-carboxylic acid" _chem_comp.type L-saccharide _chem_comp.pdbx_type ATOMS _chem_comp.formula "C14 H23 N5 O5" _chem_comp.mon_nstd_parent_comp_id ? _chem_comp.pdbx_synonyms "4-ACETYL-4-GUANIDINO-6-METHYL(PROPYL)CARBOXAMIDE-4,5-DIHYDRO-2H-PYRAN-2-CARBOXYLIC ACID" _chem_comp.pdbx_formal_charge 0 _chem_comp.pdbx_initial_date 1999-07-08 _chem_comp.pdbx_modified_date 2020-07-17 _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 341.363 _chem_comp.one_letter_code ? _chem_comp.three_letter_code G20 _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 2QWF _chem_comp.pdbx_subcomponent_list ? _chem_comp.pdbx_processing_site RCSB # _pdbx_chem_comp_synonyms.ordinal 1 _pdbx_chem_comp_synonyms.comp_id G20 _pdbx_chem_comp_synonyms.name "4-ACETYL-4-GUANIDINO-6-METHYL(PROPYL)CARBOXAMIDE-4,5-DIHYDRO-2H-PYRAN-2-CARBOXYLIC ACID" _pdbx_chem_comp_synonyms.provenance PDB _pdbx_chem_comp_synonyms.type ? # # 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 G20 C1 C1 C 0 1 N N N 23.631 19.829 64.890 3.269 0.120 -2.195 C1 G20 1 G20 O1A O1A O 0 1 N N N 24.220 20.893 65.141 3.392 -0.136 -3.376 O1A G20 2 G20 O1B O1B O 0 1 N N N 22.404 19.670 65.115 4.350 0.449 -1.460 O1B G20 3 G20 C2 C2 C 0 1 N N N 24.430 18.879 64.220 1.937 0.072 -1.565 C2 G20 4 G20 C3 C3 C 0 1 N N N 23.967 17.697 63.926 0.924 -0.256 -2.344 C3 G20 5 G20 C4 C4 C 0 1 N N S 24.592 16.730 62.821 -0.487 -0.361 -1.826 C4 G20 6 G20 C5 C5 C 0 1 N N R 25.983 16.876 62.786 -0.528 0.255 -0.420 C5 G20 7 G20 N5 N5 N 0 1 N N N 26.592 16.177 61.679 -1.735 -0.188 0.282 N5 G20 8 G20 C10 C10 C 0 1 N N N 27.077 14.949 61.837 -2.468 0.696 0.986 C10 G20 9 G20 O10 O10 O 0 1 N N N 27.057 14.354 62.916 -2.169 1.872 0.981 O10 G20 10 G20 C11 C11 C 0 1 N N N 27.570 14.290 60.559 -3.659 0.225 1.780 C11 G20 11 G20 C6 C6 C 0 1 N N R 26.277 18.367 62.827 0.721 -0.225 0.327 C6 G20 12 G20 O6 O6 O 0 1 N N N 25.739 18.935 63.984 1.875 0.367 -0.255 O6 G20 13 G20 C7 C7 C 0 1 N N N 27.781 18.403 62.922 0.626 0.176 1.777 C7 G20 14 G20 O7 O7 O 0 1 N N N 28.329 18.056 63.976 1.175 1.187 2.162 O7 G20 15 G20 N8 N8 N 0 1 N N N 28.479 18.732 61.821 -0.068 -0.586 2.644 N8 G20 16 G20 C81 C81 C 0 1 N N N 27.982 19.086 60.480 -0.625 -1.868 2.207 C81 G20 17 G20 C9 C9 C 0 1 N N N 29.952 18.690 62.006 -0.266 -0.132 4.023 C9 G20 18 G20 C91 C91 C 0 1 N N N 30.449 17.288 62.443 0.884 -0.637 4.896 C91 G20 19 G20 C92 C92 C 0 1 N N N 31.945 17.121 62.324 0.677 -0.164 6.336 C92 G20 20 G20 NE NE N 0 1 N N N 24.236 15.291 62.936 -1.395 0.369 -2.714 NE G20 21 G20 CZ CZ C 0 1 N N N 23.862 14.335 61.987 -1.984 -0.275 -3.776 CZ G20 22 G20 NH1 NH1 N 0 1 N N N 23.842 14.659 60.699 -1.736 -1.536 -3.992 NH1 G20 23 G20 NH2 NH2 N 0 1 N N N 23.618 13.070 62.357 -2.836 0.409 -4.610 NH2 G20 24 G20 HO1 HO1 H 0 1 N N N 21.953 18.856 64.923 5.224 0.480 -1.873 HO1 G20 25 G20 H3 H3 H 0 1 N N N 23.093 17.524 64.577 1.112 -0.457 -3.388 H3 G20 26 G20 H4 H4 H 0 1 N N N 24.125 17.060 61.864 -0.785 -1.408 -1.777 H4 G20 27 G20 H5 H5 H 0 1 N N N 26.453 16.389 63.672 -0.520 1.342 -0.492 H5 G20 28 G20 HN5 HN5 H 0 1 N N N 26.683 16.568 60.741 -2.006 -1.118 0.240 HN5 G20 29 G20 H111 H111 H 0 0 N N N 27.976 13.260 60.691 -4.160 1.084 2.227 H111 G20 30 G20 H112 H112 H 0 0 N N N 26.764 14.291 59.788 -4.352 -0.296 1.121 H112 G20 31 G20 H113 H113 H 0 0 N N N 28.321 14.940 60.053 -3.326 -0.450 2.567 H113 G20 32 G20 H6 H6 H 0 1 N N N 25.854 18.921 61.956 0.794 -1.311 0.255 H6 G20 33 G20 H811 H811 H 0 0 N N N 28.560 19.358 59.566 -0.459 -1.991 1.137 H811 G20 34 G20 H812 H812 H 0 0 N N N 27.327 18.237 60.173 -0.135 -2.679 2.746 H812 G20 35 G20 H813 H813 H 0 0 N N N 27.268 19.927 60.641 -1.695 -1.889 2.414 H813 G20 36 G20 H91 H91 H 0 1 N N N 30.483 19.038 61.089 -1.209 -0.524 4.402 H91 G20 37 G20 H92 H92 H 0 1 N N N 30.291 19.477 62.718 -0.289 0.957 4.047 H92 G20 38 G20 H911 H911 H 0 0 N N N 30.104 17.050 63.476 1.827 -0.245 4.516 H911 G20 39 G20 H912 H912 H 0 0 N N N 29.915 16.485 61.882 0.907 -1.727 4.872 H912 G20 40 G20 H921 H921 H 0 0 N N N 32.302 16.112 62.638 1.496 -0.524 6.958 H921 G20 41 G20 H922 H922 H 0 0 N N N 32.289 17.358 61.290 0.654 0.925 6.360 H922 G20 42 G20 H923 H923 H 0 0 N N N 32.479 17.923 62.884 -0.266 -0.556 6.715 H923 G20 43 G20 HNE HNE H 0 1 N N N 23.482 15.271 63.623 -1.580 1.307 -2.554 HNE G20 44 G20 HN1 HN1 H 0 1 N N N 24.049 14.796 61.688 -2.151 -1.991 -4.741 HN1 G20 45 G20 HN21 HN21 H 0 0 N N N 23.345 12.372 61.664 -3.252 -0.045 -5.359 HN21 G20 46 G20 HN22 HN22 H 0 0 N N N 22.912 13.082 63.093 -3.021 1.348 -4.449 HN22 G20 47 # # 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 G20 C1 O1A DOUB N N 1 G20 C1 O1B SING N N 2 G20 C1 C2 SING N N 3 G20 O1B HO1 SING N N 4 G20 C2 C3 DOUB N N 5 G20 C2 O6 SING N N 6 G20 C3 C4 SING N N 7 G20 C3 H3 SING N N 8 G20 C4 C5 SING N N 9 G20 C4 NE SING N N 10 G20 C4 H4 SING N N 11 G20 C5 N5 SING N N 12 G20 C5 C6 SING N N 13 G20 C5 H5 SING N N 14 G20 N5 C10 SING N N 15 G20 N5 HN5 SING N N 16 G20 C10 O10 DOUB N N 17 G20 C10 C11 SING N N 18 G20 C11 H111 SING N N 19 G20 C11 H112 SING N N 20 G20 C11 H113 SING N N 21 G20 C6 O6 SING N N 22 G20 C6 C7 SING N N 23 G20 C6 H6 SING N N 24 G20 C7 O7 DOUB N N 25 G20 C7 N8 SING N N 26 G20 N8 C81 SING N N 27 G20 N8 C9 SING N N 28 G20 C81 H811 SING N N 29 G20 C81 H812 SING N N 30 G20 C81 H813 SING N N 31 G20 C9 C91 SING N N 32 G20 C9 H91 SING N N 33 G20 C9 H92 SING N N 34 G20 C91 C92 SING N N 35 G20 C91 H911 SING N N 36 G20 C91 H912 SING N N 37 G20 C92 H921 SING N N 38 G20 C92 H922 SING N N 39 G20 C92 H923 SING N N 40 G20 NE CZ SING N N 41 G20 NE HNE SING N N 42 G20 CZ NH1 DOUB N N 43 G20 CZ NH2 SING N N 44 G20 NH1 HN1 SING N N 45 G20 NH2 HN21 SING N N 46 G20 NH2 HN22 SING N N 47 # # 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 G20 SMILES ACDLabs 10.04 "O=C(O)C=1OC(C(=O)N(CCC)C)C(NC(=O)C)C(NC(=[N@H])N)C=1" G20 SMILES_CANONICAL CACTVS 3.341 "CCCN(C)C(=O)[C@@H]1OC(=C[C@H](NC(N)=N)[C@H]1NC(C)=O)C(O)=O" G20 SMILES CACTVS 3.341 "CCCN(C)C(=O)[CH]1OC(=C[CH](NC(N)=N)[CH]1NC(C)=O)C(O)=O" G20 SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 "[H]/N=C(/N)\N[C@H]1C=C(O[C@H]([C@@H]1NC(=O)C)C(=O)N(C)CCC)C(=O)O" G20 SMILES "OpenEye OEToolkits" 1.5.0 "[H]N=C(N)NC1C=C(OC(C1NC(=O)C)C(=O)N(C)CCC)C(=O)O" G20 InChI InChI 1.03 "InChI=1S/C14H23N5O5/c1-4-5-19(3)12(21)11-10(17-7(2)20)8(18-14(15)16)6-9(24-11)13(22)23/h6,8,10-11H,4-5H2,1-3H3,(H,17,20)(H,22,23)(H4,15,16,18)/t8-,10+,11+/m0/s1" G20 InChIKey InChI 1.03 QPJWMZVTNXFTKV-JMJZKYOTSA-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 G20 "SYSTEMATIC NAME" ACDLabs 10.04 ;(2R,3R,4S)-3-(acetylamino)-4-carbamimidamido-2-[methyl(propyl)carbamoyl]-3,4-dihydro-2H-pyran-6-carboxylic acid (non-preferred name) ; G20 "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "(4S,5R,6R)-5-acetamido-4-carbamimidamido-6-(methyl-propyl-carbamoyl)-5,6-dihydro-4H-pyran-2-carboxylic acid" # # loop_ _pdbx_chem_comp_feature.comp_id _pdbx_chem_comp_feature.type _pdbx_chem_comp_feature.value _pdbx_chem_comp_feature.source _pdbx_chem_comp_feature.support G20 "CARBOHYDRATE ISOMER" L PDB ? G20 "CARBOHYDRATE RING" dihydropyran PDB ? G20 "CARBOHYDRATE PRIMARY CARBONYL GROUP" ketose PDB ? # # loop_ _pdbx_chem_comp_audit.comp_id _pdbx_chem_comp_audit.action_type _pdbx_chem_comp_audit.date _pdbx_chem_comp_audit.processing_site G20 "Create component" 1999-07-08 RCSB G20 "Modify descriptor" 2011-06-04 RCSB G20 "Other modification" 2020-07-03 RCSB G20 "Modify name" 2020-07-17 RCSB G20 "Modify synonyms" 2020-07-17 RCSB G20 "Modify internal type" 2020-07-17 RCSB G20 "Modify linking type" 2020-07-17 RCSB ##