data_5I5 # _chem_comp.id 5I5 _chem_comp.name "7-(5-DEOXY-BETA-D-RIBOFURANOSYL)-5-IODO-7H-PYRROLO[2,3-D]PYRIMIDIN-4-AMINE" _chem_comp.type NON-POLYMER _chem_comp.pdbx_type HETAIN _chem_comp.formula "C11 H13 I N4 O3" _chem_comp.mon_nstd_parent_comp_id ? _chem_comp.pdbx_synonyms ;5'-DEOXY-5-IODOTUBERCIDIN; (2R,3R,4S,5R)-2-(4-AMINO-5-IODO-7H-PYRROLO[2,3-D]PYRIMIDIN-7-YL)-5-(METHYL)TETRAHYDROFURAN-3,4-DIOL ; _chem_comp.pdbx_formal_charge 0 _chem_comp.pdbx_initial_date 2006-10-20 _chem_comp.pdbx_modified_date 2020-06-17 _chem_comp.pdbx_ambiguous_flag ? _chem_comp.pdbx_release_status REL _chem_comp.pdbx_replaced_by ? _chem_comp.pdbx_replaces ? _chem_comp.formula_weight 376.150 _chem_comp.one_letter_code ? _chem_comp.three_letter_code 5I5 _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 2I6A _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 5I5 N1 N1 N 0 1 Y N N 9.204 -23.294 19.115 -2.846 1.155 -4.496 N1 5I5 1 5I5 C1 C1 C 0 1 Y N N 8.719 -23.421 20.371 -1.634 0.721 -4.911 C1 5I5 2 5I5 C2 C2 C 0 1 Y N N 8.567 -22.324 21.216 -0.533 0.842 -4.064 C2 5I5 3 5I5 C3 C3 C 0 1 Y N N 8.959 -21.067 20.670 -0.766 1.416 -2.820 C3 5I5 4 5I5 N2 N2 N 0 1 Y N N 9.436 -20.948 19.408 -1.943 1.866 -2.350 N2 5I5 5 5I5 C4 C4 C 0 1 Y N N 9.556 -22.068 18.669 -2.924 1.693 -3.258 C4 5I5 6 5I5 C5 C5 C 0 1 Y N N 8.113 -22.069 22.568 0.847 0.523 -4.120 C5 5I5 7 5I5 C6 C6 C 0 1 Y N N 8.259 -20.679 22.774 1.411 0.906 -2.922 C6 5I5 8 5I5 N3 N3 N 0 1 Y N N 8.752 -20.079 21.646 0.424 1.450 -2.136 N3 5I5 9 5I5 I I I 0 1 N N N 7.400 -23.390 23.953 1.912 -0.347 -5.645 I 5I5 10 5I5 N4 N4 N 0 1 N N N 8.441 -24.681 20.705 -1.524 0.157 -6.195 N4 5I5 11 5I5 C7 C7 C 0 1 N N S 8.015 -16.455 21.747 1.969 0.663 0.677 C7 5I5 12 5I5 C8 C8 C 0 1 N N R 7.610 -17.929 21.538 0.518 0.913 0.310 C8 5I5 13 5I5 C9 C9 C 0 1 N N R 8.967 -18.627 21.466 0.622 1.976 -0.784 C9 5I5 14 5I5 O3 O3 O 0 1 N N N 9.650 -17.992 22.508 1.933 2.574 -0.689 O3 5I5 15 5I5 C10 C10 C 0 1 N N R 9.402 -16.602 22.411 2.595 2.031 0.465 C10 5I5 16 5I5 O2 O2 O 0 1 N N N 8.103 -15.842 20.474 2.143 0.197 1.998 O2 5I5 17 5I5 O1 O1 O 0 1 N N N 6.762 -18.093 20.365 -0.210 1.445 1.415 O1 5I5 18 5I5 C11 C11 C 0 1 N N N 9.453 -15.954 23.796 4.092 1.980 0.223 C11 5I5 19 5I5 H4 H4 H 0 1 N N N 9.954 -21.982 17.669 -3.910 2.031 -2.956 H4 5I5 20 5I5 H6 H6 H 0 1 N N N 8.016 -20.163 23.691 2.429 0.845 -2.557 H6 5I5 21 5I5 HN41 1HN4 H 0 0 N N N 8.371 -25.238 19.877 -1.842 -0.781 -6.349 HN41 5I5 22 5I5 HN42 2HN4 H 0 0 N N N 9.170 -25.040 21.288 -1.045 0.663 -6.915 HN42 5I5 23 5I5 H7 H7 H 0 1 N N N 7.324 -15.843 22.346 2.403 -0.065 -0.019 H7 5I5 24 5I5 H8 H8 H 0 1 N N N 6.980 -18.356 22.332 -0.000 0.001 -0.003 H8 5I5 25 5I5 H9 H9 H 0 1 N N N 9.529 -18.554 20.523 -0.125 2.769 -0.673 H9 5I5 26 5I5 H10 H10 H 0 1 N N N 10.166 -16.089 21.808 2.399 2.693 1.317 H10 5I5 27 5I5 HO2 HO2 H 0 1 N N N 8.123 -14.898 20.577 3.003 0.531 2.294 HO2 5I5 28 5I5 HO1 HO1 H 0 1 N N N 5.852 -18.129 20.634 -1.062 1.768 1.071 HO1 5I5 29 5I5 H111 1H11 H 0 0 N N N 9.465 -16.738 24.568 4.561 2.925 0.512 H111 5I5 30 5I5 H112 2H11 H 0 0 N N N 10.363 -15.342 23.881 4.549 1.176 0.807 H112 5I5 31 5I5 H113 3H11 H 0 0 N N N 8.567 -15.317 23.935 4.304 1.800 -0.835 H113 5I5 32 # # 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 5I5 N1 C4 DOUB Y N 1 5I5 N1 C1 SING Y N 2 5I5 C1 N4 SING N N 3 5I5 C1 C2 DOUB Y N 4 5I5 C2 C3 SING Y N 5 5I5 C2 C5 SING Y N 6 5I5 C3 N2 DOUB Y N 7 5I5 C3 N3 SING Y N 8 5I5 N2 C4 SING Y N 9 5I5 C4 H4 SING N N 10 5I5 C5 C6 DOUB Y N 11 5I5 C5 I SING N N 12 5I5 C6 N3 SING Y N 13 5I5 C6 H6 SING N N 14 5I5 N3 C9 SING N N 15 5I5 N4 HN41 SING N N 16 5I5 N4 HN42 SING N N 17 5I5 C7 O2 SING N N 18 5I5 C7 C8 SING N N 19 5I5 C7 C10 SING N N 20 5I5 C7 H7 SING N N 21 5I5 C8 O1 SING N N 22 5I5 C8 C9 SING N N 23 5I5 C8 H8 SING N N 24 5I5 C9 O3 SING N N 25 5I5 C9 H9 SING N N 26 5I5 O3 C10 SING N N 27 5I5 C10 C11 SING N N 28 5I5 C10 H10 SING N N 29 5I5 O2 HO2 SING N N 30 5I5 O1 HO1 SING N N 31 5I5 C11 H111 SING N N 32 5I5 C11 H112 SING N N 33 5I5 C11 H113 SING N N 34 # # 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 5I5 SMILES ACDLabs 10.04 "Ic2c1c(ncnc1n(c2)C3OC(C(O)C3O)C)N" 5I5 SMILES_CANONICAL CACTVS 3.341 "C[C@H]1O[C@H]([C@H](O)[C@@H]1O)n2cc(I)c3c(N)ncnc23" 5I5 SMILES CACTVS 3.341 "C[CH]1O[CH]([CH](O)[CH]1O)n2cc(I)c3c(N)ncnc23" 5I5 SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 "C[C@@H]1[C@H]([C@H]([C@@H](O1)n2cc(c3c2ncnc3N)I)O)O" 5I5 SMILES "OpenEye OEToolkits" 1.5.0 "CC1C(C(C(O1)n2cc(c3c2ncnc3N)I)O)O" 5I5 InChI InChI 1.03 "InChI=1S/C11H13IN4O3/c1-4-7(17)8(18)11(19-4)16-2-5(12)6-9(13)14-3-15-10(6)16/h2-4,7-8,11,17-18H,1H3,(H2,13,14,15)/t4-,7-,8-,11-/m1/s1" 5I5 InChIKey InChI 1.03 NTXUAWGNGBSCRS-TZQXKBMNSA-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 5I5 "SYSTEMATIC NAME" ACDLabs 10.04 "7-(5-deoxy-beta-D-ribofuranosyl)-5-iodo-7H-pyrrolo[2,3-d]pyrimidin-4-amine" 5I5 "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "(2R,3R,4S,5R)-2-(4-amino-5-iodo-pyrrolo[2,3-d]pyrimidin-7-yl)-5-methyl-oxolane-3,4-diol" # # loop_ _pdbx_chem_comp_audit.comp_id _pdbx_chem_comp_audit.action_type _pdbx_chem_comp_audit.date _pdbx_chem_comp_audit.processing_site 5I5 "Create component" 2006-10-20 RCSB 5I5 "Modify descriptor" 2011-06-04 RCSB 5I5 "Modify synonyms" 2020-06-05 PDBE # # loop_ _pdbx_chem_comp_synonyms.ordinal _pdbx_chem_comp_synonyms.comp_id _pdbx_chem_comp_synonyms.name _pdbx_chem_comp_synonyms.provenance _pdbx_chem_comp_synonyms.type 1 5I5 "5'-DEOXY-5-IODOTUBERCIDIN" ? ? 2 5I5 "(2R,3R,4S,5R)-2-(4-AMINO-5-IODO-7H-PYRROLO[2,3-D]PYRIMIDIN-7-YL)-5-(METHYL)TETRAHYDROFURAN-3,4-DIOL" ? ? ##