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 
# 
