data_3XN # _chem_comp.id 3XN _chem_comp.name "4-(5-nitro-1H-indol-1-yl)phenyl alpha-D-mannopyranoside" _chem_comp.type NON-POLYMER _chem_comp.pdbx_type HETAIN _chem_comp.formula "C20 H20 N2 O8" _chem_comp.mon_nstd_parent_comp_id ? _chem_comp.pdbx_synonyms ? _chem_comp.pdbx_formal_charge 0 _chem_comp.pdbx_initial_date 2014-12-06 _chem_comp.pdbx_modified_date 2015-05-15 _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 416.381 _chem_comp.one_letter_code ? _chem_comp.three_letter_code 3XN _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 4X5Q _chem_comp.pdbx_subcomponent_list ? _chem_comp.pdbx_processing_site EBI # 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 3XN O3 O1 O 0 1 N N N -24.111 -9.768 -7.680 -6.675 -2.149 -0.538 O3 3XN 1 3XN C4 C1 C 0 1 N N R -27.162 -7.591 -7.918 -4.498 0.908 -0.396 C4 3XN 2 3XN C5 C2 C 0 1 N N N -27.721 -6.440 -7.124 -4.822 2.403 -0.419 C5 3XN 3 3XN O4 O2 O 0 1 N N N -24.103 -7.684 -9.578 -5.643 -1.373 1.945 O4 3XN 4 3XN C6 C3 C 0 1 Y N N -28.577 -8.916 -10.681 -1.353 -0.611 -0.025 C6 3XN 5 3XN N1 N1 N 1 1 N N N -37.473 -10.640 -10.013 7.692 -0.988 -0.201 N1 3XN 6 3XN C7 C4 C 0 1 Y N N -29.003 -7.721 -11.187 -1.009 0.226 1.026 C7 3XN 7 3XN C8 C5 C 0 1 Y N N -30.334 -7.636 -11.629 0.258 0.772 1.088 C8 3XN 8 3XN C9 C6 C 0 1 Y N N -31.186 -8.747 -11.539 1.188 0.482 0.099 C9 3XN 9 3XN O5 O3 O 0 1 N N N -27.278 -9.117 -10.263 -2.603 -1.143 -0.089 O5 3XN 10 3XN C10 C7 C 0 1 Y N N -30.713 -9.939 -11.027 0.843 -0.357 -0.953 C10 3XN 11 3XN O6 O4 O 0 1 N N N -37.535 -11.073 -8.864 7.931 -2.168 -0.381 O6 3XN 12 3XN C11 C8 C 0 1 Y N N -29.420 -10.019 -10.604 -0.425 -0.901 -1.014 C11 3XN 13 3XN C12 C9 C 0 1 Y N N -32.989 -7.902 -13.061 2.752 2.363 0.356 C12 3XN 14 3XN C13 C10 C 0 1 Y N N -34.374 -8.077 -13.187 4.080 2.556 0.369 C13 3XN 15 3XN O7 O5 O -1 1 N N N -38.439 -10.579 -10.758 8.607 -0.191 -0.091 O7 3XN 16 3XN C14 C11 C 0 1 Y N N -34.803 -8.954 -12.099 4.706 1.247 0.167 C14 3XN 17 3XN C15 C12 C 0 1 Y N N -33.635 -9.300 -11.349 3.650 0.325 0.042 C15 3XN 18 3XN C18 C13 C 0 1 Y N N -36.139 -10.171 -10.505 6.290 -0.521 -0.114 C18 3XN 19 3XN C19 C14 C 0 1 Y N N -36.072 -9.399 -11.673 6.028 0.805 0.086 C19 3XN 20 3XN C17 C15 C 0 1 Y N N -34.987 -10.521 -9.755 5.252 -1.433 -0.240 C17 3XN 21 3XN C16 C16 C 0 1 Y N N -33.738 -10.095 -10.170 3.939 -1.020 -0.163 C16 3XN 22 3XN N N2 N 0 1 Y N N -32.549 -8.658 -11.949 2.475 1.036 0.161 N 3XN 23 3XN C C17 C 0 1 N N R -26.402 -8.076 -10.078 -3.508 -0.802 0.963 C 3XN 24 3XN O O6 O 0 1 N N N -26.851 -7.074 -9.220 -3.877 0.573 0.847 O 3XN 25 3XN O1 O7 O 0 1 N N N -26.760 -5.391 -6.970 -3.607 3.154 -0.391 O1 3XN 26 3XN C3 C18 C 0 1 N N S -25.910 -8.213 -7.293 -5.791 0.102 -0.552 C3 3XN 27 3XN O2 O8 O 0 1 N N N -26.239 -8.827 -6.063 -6.384 0.392 -1.819 O2 3XN 28 3XN C2 C19 C 0 1 N N S -25.332 -9.273 -8.223 -5.466 -1.392 -0.468 C2 3XN 29 3XN C1 C20 C 0 1 N N S -25.111 -8.694 -9.617 -4.760 -1.676 0.862 C1 3XN 30 3XN HO3 H1 H 0 1 N N N -24.270 -10.123 -6.813 -6.544 -3.106 -0.491 HO3 3XN 31 3XN H4 H2 H 0 1 N N N -27.933 -8.371 -8.002 -3.821 0.670 -1.217 H4 3XN 32 3XN H52 H3 H 0 1 N N N -28.604 -6.042 -7.646 -5.376 2.641 -1.327 H52 3XN 33 3XN H51 H4 H 0 1 N N N -28.016 -6.803 -6.128 -5.427 2.657 0.452 H51 3XN 34 3XN HO4 H5 H 0 1 N N N -23.283 -8.066 -9.288 -5.259 -1.525 2.819 HO4 3XN 35 3XN H7 H6 H 0 1 N N N -28.340 -6.871 -11.245 -1.732 0.452 1.796 H7 3XN 36 3XN H8 H7 H 0 1 N N N -30.704 -6.709 -12.041 0.526 1.424 1.906 H8 3XN 37 3XN H10 H8 H 0 1 N N N -31.362 -10.800 -10.962 1.566 -0.583 -1.723 H10 3XN 38 3XN H11 H9 H 0 1 N N N -29.046 -10.950 -10.204 -0.694 -1.550 -1.834 H11 3XN 39 3XN H12 H10 H 0 1 N N N -32.366 -7.295 -13.702 2.011 3.139 0.484 H12 3XN 40 3XN H13 H11 H 0 1 N N N -35.007 -7.644 -13.947 4.591 3.498 0.503 H13 3XN 41 3XN H19 H12 H 0 1 N N N -36.964 -9.153 -12.229 6.841 1.510 0.181 H19 3XN 42 3XN H17 H13 H 0 1 N N N -35.085 -11.119 -8.861 5.474 -2.478 -0.400 H17 3XN 43 3XN H16 H14 H 0 1 N N N -32.854 -10.361 -9.609 3.138 -1.737 -0.260 H16 3XN 44 3XN H H15 H 0 1 N N N -26.199 -7.618 -11.058 -3.025 -0.969 1.926 H 3XN 45 3XN HO1 H16 H 0 1 N N N -27.142 -4.682 -6.466 -3.737 4.112 -0.403 HO1 3XN 46 3XN H3 H17 H 0 1 N N N -25.159 -7.424 -7.141 -6.485 0.370 0.245 H3 3XN 47 3XN HO2 H18 H 0 1 N N N -26.601 -8.178 -5.471 -7.209 -0.085 -1.986 HO2 3XN 48 3XN H2 H19 H 0 1 N N N -26.059 -10.094 -8.303 -4.813 -1.670 -1.295 H2 3XN 49 3XN H1 H20 H 0 1 N N N -24.823 -9.503 -10.305 -4.476 -2.727 0.908 H1 3XN 50 # 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 3XN C13 C12 DOUB Y N 1 3XN C13 C14 SING Y N 2 3XN C12 N SING Y N 3 3XN C14 C19 DOUB Y N 4 3XN C14 C15 SING Y N 5 3XN N C9 SING N N 6 3XN N C15 SING Y N 7 3XN C19 C18 SING Y N 8 3XN C8 C9 DOUB Y N 9 3XN C8 C7 SING Y N 10 3XN C9 C10 SING Y N 11 3XN C15 C16 DOUB Y N 12 3XN C7 C6 DOUB Y N 13 3XN C10 C11 DOUB Y N 14 3XN O7 N1 SING N N 15 3XN C6 C11 SING Y N 16 3XN C6 O5 SING N N 17 3XN C18 N1 SING N N 18 3XN C18 C17 DOUB Y N 19 3XN O5 C SING N N 20 3XN C16 C17 SING Y N 21 3XN C C1 SING N N 22 3XN C O SING N N 23 3XN N1 O6 DOUB N N 24 3XN C1 O4 SING N N 25 3XN C1 C2 SING N N 26 3XN O C4 SING N N 27 3XN C2 O3 SING N N 28 3XN C2 C3 SING N N 29 3XN C4 C3 SING N N 30 3XN C4 C5 SING N N 31 3XN C3 O2 SING N N 32 3XN C5 O1 SING N N 33 3XN O3 HO3 SING N N 34 3XN C4 H4 SING N N 35 3XN C5 H52 SING N N 36 3XN C5 H51 SING N N 37 3XN O4 HO4 SING N N 38 3XN C7 H7 SING N N 39 3XN C8 H8 SING N N 40 3XN C10 H10 SING N N 41 3XN C11 H11 SING N N 42 3XN C12 H12 SING N N 43 3XN C13 H13 SING N N 44 3XN C19 H19 SING N N 45 3XN C17 H17 SING N N 46 3XN C16 H16 SING N N 47 3XN C H SING N N 48 3XN O1 HO1 SING N N 49 3XN C3 H3 SING N N 50 3XN O2 HO2 SING N N 51 3XN C2 H2 SING N N 52 3XN C1 H1 SING N N 53 # 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 3XN SMILES ACDLabs 12.01 "[O-][N+](=O)c1cc2c(cc1)n(cc2)c4ccc(OC3OC(C(O)C(O)C3O)CO)cc4" 3XN InChI InChI 1.03 "InChI=1S/C20H20N2O8/c23-10-16-17(24)18(25)19(26)20(30-16)29-14-4-1-12(2-5-14)21-8-7-11-9-13(22(27)28)3-6-15(11)21/h1-9,16-20,23-26H,10H2/t16-,17-,18+,19+,20+/m1/s1" 3XN InChIKey InChI 1.03 CPRVANUZGRDTIH-SLHNCBLASA-N 3XN SMILES_CANONICAL CACTVS 3.385 "OC[C@H]1O[C@H](Oc2ccc(cc2)n3ccc4cc(ccc34)[N+]([O-])=O)[C@@H](O)[C@@H](O)[C@@H]1O" 3XN SMILES CACTVS 3.385 "OC[CH]1O[CH](Oc2ccc(cc2)n3ccc4cc(ccc34)[N+]([O-])=O)[CH](O)[CH](O)[CH]1O" 3XN SMILES_CANONICAL "OpenEye OEToolkits" 1.9.2 "c1cc(ccc1n2ccc3c2ccc(c3)[N+](=O)[O-])O[C@@H]4[C@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O" 3XN SMILES "OpenEye OEToolkits" 1.9.2 "c1cc(ccc1n2ccc3c2ccc(c3)[N+](=O)[O-])OC4C(C(C(C(O4)CO)O)O)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 3XN "SYSTEMATIC NAME" ACDLabs 12.01 "4-(5-nitro-1H-indol-1-yl)phenyl alpha-D-mannopyranoside" 3XN "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.9.2 "(2R,3S,4S,5S,6R)-2-(hydroxymethyl)-6-[4-(5-nitroindol-1-yl)phenoxy]oxane-3,4,5-triol" # loop_ _pdbx_chem_comp_audit.comp_id _pdbx_chem_comp_audit.action_type _pdbx_chem_comp_audit.date _pdbx_chem_comp_audit.processing_site 3XN "Create component" 2014-12-06 EBI 3XN "Initial release" 2015-05-20 RCSB #