data_FBN # _chem_comp.id FBN _chem_comp.name "5'-deoxy-5'-[4-({[(2,3-dihydroxy-5-nitrophenyl)carbonyl]amino}methyl)-1H-1,2,3-triazol-1-yl]adenosine" _chem_comp.type NON-POLYMER _chem_comp.pdbx_type HETAIN _chem_comp.formula "C20 H20 N10 O8" _chem_comp.mon_nstd_parent_comp_id ? _chem_comp.pdbx_synonyms ;N-[(1-{[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl}-1H-1,2,3-triazol-4-yl)methyl]-2,3-dihy droxy-5-nitrobenzamide ; _chem_comp.pdbx_formal_charge 0 _chem_comp.pdbx_initial_date 2009-09-30 _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 528.435 _chem_comp.one_letter_code ? _chem_comp.three_letter_code FBN _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 3A7D _chem_comp.pdbx_subcomponent_list ? _chem_comp.pdbx_processing_site PDBJ # # 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 FBN C1 C1 C 0 1 Y N N 30.759 -2.475 -9.007 -6.512 0.649 0.567 C1 FBN 1 FBN N2 N2 N 0 1 Y N N 30.451 -1.321 -8.364 -7.432 -0.136 1.116 N2 FBN 2 FBN C3 C3 C 0 1 Y N N 31.074 -0.987 -7.218 -8.544 0.373 1.603 C3 FBN 3 FBN N4 N4 N 0 1 Y N N 32.023 -1.751 -6.645 -8.804 1.667 1.572 N4 FBN 4 FBN C5 C5 C 0 1 Y N N 32.436 -2.923 -7.180 -7.943 2.530 1.043 C5 FBN 5 FBN C6 C6 C 0 1 Y N N 31.789 -3.359 -8.440 -6.741 2.034 0.511 C6 FBN 6 FBN N8 N8 N 0 1 Y N N 31.888 -4.417 -9.270 -5.662 2.593 -0.089 N8 FBN 7 FBN C9 C9 C 0 1 Y N N 31.004 -4.222 -10.289 -4.807 1.663 -0.397 C9 FBN 8 FBN N10 N10 N 0 1 Y N N 30.335 -3.065 -10.127 -5.283 0.446 -0.009 N10 FBN 9 FBN N11 N11 N 0 1 N N N 33.396 -3.674 -6.580 -8.225 3.884 1.015 N11 FBN 10 FBN C15 C15 C 0 1 N N R 29.289 -2.514 -11.015 -4.607 -0.843 -0.176 C15 FBN 11 FBN O16 O16 O 0 1 N N N 28.268 -3.471 -11.288 -3.180 -0.651 -0.292 O16 FBN 12 FBN C17 C17 C 0 1 N N R 27.534 -2.932 -12.397 -2.685 -1.849 -0.930 C17 FBN 13 FBN C18 C18 C 0 1 N N S 28.486 -2.052 -13.170 -3.733 -2.178 -2.017 C18 FBN 14 FBN C19 C19 C 0 1 N N R 29.791 -2.151 -12.408 -5.026 -1.501 -1.509 C19 FBN 15 FBN O21 O21 O 0 1 N N N 27.906 -0.756 -13.087 -3.916 -3.591 -2.124 O21 FBN 16 FBN O23 O23 O 0 1 N N N 30.497 -0.912 -12.435 -6.047 -2.476 -1.287 O23 FBN 17 FBN C27 C27 C 0 1 N N N 27.040 -3.979 -13.356 -1.320 -1.587 -1.569 C27 FBN 18 FBN N29 N29 N 0 1 Y N N 27.915 -5.109 -13.214 -0.333 -1.320 -0.519 N29 FBN 19 FBN C32 C32 C 0 1 Y N N 27.743 -6.172 -12.457 0.836 -1.979 -0.344 C32 FBN 20 FBN C33 C33 C 0 1 Y N N 28.848 -6.951 -12.659 1.430 -1.413 0.732 C33 FBN 21 FBN N34 N34 N 0 1 Y N N 29.693 -6.383 -13.570 0.606 -0.448 1.157 N34 FBN 22 FBN N35 N35 N 0 1 Y N N 29.110 -5.155 -13.953 -0.426 -0.415 0.391 N35 FBN 23 FBN C37 C37 C 0 1 N N N 28.897 -8.245 -11.930 2.758 -1.795 1.334 C37 FBN 24 FBN N38 N38 N 0 1 N N N 27.506 -8.609 -12.112 3.808 -0.931 0.788 N38 FBN 25 FBN C41 C41 C 0 1 N N N 27.247 -9.211 -13.256 5.086 -1.090 1.185 C41 FBN 26 FBN C42 C42 C 0 1 Y N N 25.905 -9.772 -13.608 6.143 -0.220 0.636 C42 FBN 27 FBN O43 O43 O 0 1 N N N 28.158 -9.373 -14.057 5.367 -1.952 1.996 O43 FBN 28 FBN C45 C45 C 0 1 Y N N 24.607 -9.429 -12.974 7.471 -0.383 1.046 C45 FBN 29 FBN C46 C46 C 0 1 Y N N 23.400 -10.119 -13.478 8.460 0.444 0.521 C46 FBN 30 FBN C47 C47 C 0 1 Y N N 23.502 -11.045 -14.503 8.128 1.421 -0.402 C47 FBN 31 FBN C48 C48 C 0 1 Y N N 24.750 -11.318 -15.064 6.813 1.582 -0.807 C48 FBN 32 FBN C49 C49 C 0 1 Y N N 25.909 -10.704 -14.624 5.824 0.767 -0.301 C49 FBN 33 FBN O52 O52 O 0 1 N N N 24.473 -8.521 -11.979 7.793 -1.341 1.951 O52 FBN 34 FBN O53 O53 O 0 1 N N N 22.202 -9.839 -12.933 9.753 0.292 0.914 O53 FBN 35 FBN N54 N54 N 1 1 N N N 24.893 -12.247 -16.089 6.470 2.630 -1.794 N54 FBN 36 FBN O55 O55 O -1 1 N N N 26.017 -12.497 -16.497 7.342 3.349 -2.247 O55 FBN 37 FBN O56 O56 O 0 1 N N N 23.917 -12.811 -16.551 5.314 2.775 -2.152 O56 FBN 38 FBN H3 H3 H 0 1 N N N 30.799 -0.061 -6.735 -9.272 -0.294 2.043 H3 FBN 39 FBN H9 H9 H 0 1 N N N 30.860 -4.903 -11.114 -3.858 1.830 -0.885 H9 FBN 40 FBN HN11 HN11 H 0 0 N N N 33.700 -3.220 -5.743 -9.059 4.214 1.385 HN11 FBN 41 FBN HN1A HN1A H 0 0 N N N 33.022 -4.574 -6.354 -7.588 4.504 0.626 HN1A FBN 42 FBN H15 H15 H 0 1 N N N 28.938 -1.631 -10.462 -4.834 -1.502 0.662 H15 FBN 43 FBN H17 H17 H 0 1 N N N 26.658 -2.405 -11.991 -2.618 -2.663 -0.209 H17 FBN 44 FBN H18 H18 H 0 1 N N N 28.660 -2.310 -14.225 -3.433 -1.757 -2.977 H18 FBN 45 FBN H19 H19 H 0 1 N N N 30.514 -2.874 -12.815 -5.365 -0.746 -2.218 H19 FBN 46 FBN HO21 HO21 H 0 0 N N N 28.451 -0.134 -13.555 -4.564 -3.854 -2.792 HO21 FBN 47 FBN HO23 HO23 H 0 0 N N N 30.788 -0.732 -13.321 -6.348 -2.920 -2.092 HO23 FBN 48 FBN H27 H27 H 0 1 N N N 26.004 -4.262 -13.116 -1.013 -2.462 -2.142 H27 FBN 49 FBN H27A H27A H 0 0 N N N 27.067 -3.599 -14.388 -1.388 -0.724 -2.231 H27A FBN 50 FBN H32 H32 H 0 1 N N N 26.904 -6.384 -11.811 1.217 -2.793 -0.942 H32 FBN 51 FBN H37 H37 H 0 1 N N N 29.605 -8.969 -12.359 2.714 -1.675 2.416 H37 FBN 52 FBN H37A H37A H 0 0 N N N 29.196 -8.149 -10.876 2.981 -2.834 1.092 H37A FBN 53 FBN HN38 HN38 H 0 0 N N N 26.802 -8.420 -11.428 3.583 -0.244 0.142 HN38 FBN 54 FBN H47 H47 H 0 1 N N N 22.621 -11.553 -14.866 8.897 2.060 -0.808 H47 FBN 55 FBN H49 H49 H 0 1 N N N 26.847 -10.963 -15.092 4.801 0.895 -0.624 H49 FBN 56 FBN HO52 HO52 H 0 0 N N N 23.559 -8.461 -11.726 8.019 -2.195 1.557 HO52 FBN 57 FBN HO53 HO53 H 0 0 N N N 21.530 -10.358 -13.360 10.260 -0.328 0.371 HO53 FBN 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 FBN C1 N2 DOUB Y N 1 FBN C1 C6 SING Y N 2 FBN C1 N10 SING Y N 3 FBN N2 C3 SING Y N 4 FBN C3 N4 DOUB Y N 5 FBN N4 C5 SING Y N 6 FBN C5 C6 DOUB Y N 7 FBN C5 N11 SING N N 8 FBN C6 N8 SING Y N 9 FBN N8 C9 DOUB Y N 10 FBN C9 N10 SING Y N 11 FBN N10 C15 SING N N 12 FBN C15 O16 SING N N 13 FBN C15 C19 SING N N 14 FBN O16 C17 SING N N 15 FBN C17 C18 SING N N 16 FBN C17 C27 SING N N 17 FBN C18 C19 SING N N 18 FBN C18 O21 SING N N 19 FBN C19 O23 SING N N 20 FBN C27 N29 SING N N 21 FBN N29 C32 SING Y N 22 FBN N29 N35 SING Y N 23 FBN C32 C33 DOUB Y N 24 FBN C33 N34 SING Y N 25 FBN C33 C37 SING N N 26 FBN N34 N35 DOUB Y N 27 FBN C37 N38 SING N N 28 FBN N38 C41 SING N N 29 FBN C41 C42 SING N N 30 FBN C41 O43 DOUB N N 31 FBN C42 C45 DOUB Y N 32 FBN C42 C49 SING Y N 33 FBN C45 C46 SING Y N 34 FBN C45 O52 SING N N 35 FBN C46 C47 DOUB Y N 36 FBN C46 O53 SING N N 37 FBN C47 C48 SING Y N 38 FBN C48 C49 DOUB Y N 39 FBN C48 N54 SING N N 40 FBN N54 O55 SING N N 41 FBN N54 O56 DOUB N N 42 FBN C3 H3 SING N N 43 FBN C9 H9 SING N N 44 FBN N11 HN11 SING N N 45 FBN N11 HN1A SING N N 46 FBN C15 H15 SING N N 47 FBN C17 H17 SING N N 48 FBN C18 H18 SING N N 49 FBN C19 H19 SING N N 50 FBN O21 HO21 SING N N 51 FBN O23 HO23 SING N N 52 FBN C27 H27 SING N N 53 FBN C27 H27A SING N N 54 FBN C32 H32 SING N N 55 FBN C37 H37 SING N N 56 FBN C37 H37A SING N N 57 FBN N38 HN38 SING N N 58 FBN C47 H47 SING N N 59 FBN C49 H49 SING N N 60 FBN O52 HO52 SING N N 61 FBN O53 HO53 SING N N 62 # # 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 FBN SMILES ACDLabs 11.02 "[O-][N+](=O)c1cc(c(O)c(O)c1)C(=O)NCc2nnn(c2)CC5OC(n4cnc3c(ncnc34)N)C(O)C5O" FBN SMILES_CANONICAL CACTVS 3.352 "Nc1ncnc2n(cnc12)[C@@H]3O[C@H](Cn4cc(CNC(=O)c5cc(cc(O)c5O)[N+]([O-])=O)nn4)[C@@H](O)[C@H]3O" FBN SMILES CACTVS 3.352 "Nc1ncnc2n(cnc12)[CH]3O[CH](Cn4cc(CNC(=O)c5cc(cc(O)c5O)[N+]([O-])=O)nn4)[CH](O)[CH]3O" FBN SMILES_CANONICAL "OpenEye OEToolkits" 1.7.0 "c1c(cc(c(c1C(=O)NCc2cn(nn2)C[C@@H]3[C@H]([C@H]([C@@H](O3)n4cnc5c4ncnc5N)O)O)O)O)[N+](=O)[O-]" FBN SMILES "OpenEye OEToolkits" 1.7.0 "c1c(cc(c(c1C(=O)NCc2cn(nn2)CC3C(C(C(O3)n4cnc5c4ncnc5N)O)O)O)O)[N+](=O)[O-]" FBN InChI InChI 1.03 "InChI=1S/C20H20N10O8/c21-17-13-18(24-6-23-17)29(7-25-13)20-16(34)15(33)12(38-20)5-28-4-8(26-27-28)3-22-19(35)10-1-9(30(36)37)2-11(31)14(10)32/h1-2,4,6-7,12,15-16,20,31-34H,3,5H2,(H,22,35)(H2,21,23,24)/t12-,15-,16-,20-/m1/s1" FBN InChIKey InChI 1.03 KWTYQIOJSHGBKG-VXHCAWKWSA-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 FBN "SYSTEMATIC NAME" ACDLabs 11.02 "5'-deoxy-5'-[4-({[(2,3-dihydroxy-5-nitrophenyl)carbonyl]amino}methyl)-1H-1,2,3-triazol-1-yl]adenosine" FBN "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.6.1 "N-[[1-[[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxy-oxolan-2-yl]methyl]-1,2,3-triazol-4-yl]methyl]-2,3-dihydroxy-5-nitro-benzamide" # # loop_ _pdbx_chem_comp_audit.comp_id _pdbx_chem_comp_audit.action_type _pdbx_chem_comp_audit.date _pdbx_chem_comp_audit.processing_site FBN "Create component" 2009-09-30 PDBJ FBN "Modify aromatic_flag" 2011-06-04 RCSB FBN "Modify descriptor" 2011-06-04 RCSB FBN "Modify synonyms" 2020-06-05 PDBE # _pdbx_chem_comp_synonyms.ordinal 1 _pdbx_chem_comp_synonyms.comp_id FBN _pdbx_chem_comp_synonyms.name "N-[(1-{[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl}-1H-1,2,3-triazol-4-yl)methyl]-2,3-dihydroxy-5-nitrobenzamide" _pdbx_chem_comp_synonyms.provenance ? _pdbx_chem_comp_synonyms.type ? ##