data_3XJ # _chem_comp.id 3XJ _chem_comp.name "4-{[3-chloro-4-(alpha-D-mannopyranosyloxy)phenyl]carbamoyl}benzoic acid" _chem_comp.type NON-POLYMER _chem_comp.pdbx_type HETAIN _chem_comp.formula "C20 H20 Cl N O9" _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 453.827 _chem_comp.one_letter_code ? _chem_comp.three_letter_code 3XJ _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 4X5P _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 3XJ O3 O1 O 0 1 N N N -15.087 50.545 -13.368 -9.494 -0.330 -1.045 O3 3XJ 1 3XJ C4 C1 C 0 1 Y N N -6.708 46.712 -11.104 -0.402 1.398 0.108 C4 3XJ 2 3XJ C5 C2 C 0 1 Y N N -5.423 46.482 -10.645 0.966 1.572 0.033 C5 3XJ 3 3XJ O4 O2 O 0 1 N N N -2.729 49.083 -9.067 3.906 -1.361 0.622 O4 3XJ 4 3XJ C6 C3 C 0 1 N N N -9.477 47.491 -12.157 -3.093 0.464 -0.152 C6 3XJ 5 3XJ C7 C4 C 0 1 Y N N -10.739 48.114 -12.599 -4.545 0.181 -0.110 C7 3XJ 6 3XJ C8 C5 C 0 1 Y N N -11.467 47.417 -13.578 -5.109 -0.402 1.026 C8 3XJ 7 3XJ C9 C6 C 0 1 Y N N -12.719 47.861 -13.974 -6.461 -0.665 1.066 C9 3XJ 8 3XJ O5 O3 O 0 1 N N N -2.182 47.259 -5.955 6.204 -0.795 -2.175 O5 3XJ 9 3XJ C10 C7 C 0 1 Y N N -13.256 48.999 -13.409 -7.266 -0.350 -0.030 C10 3XJ 10 3XJ O6 O4 O 0 1 N N N -0.090 46.265 -7.581 7.319 0.864 -0.128 O6 3XJ 11 3XJ C11 C8 C 0 1 Y N N -12.527 49.705 -12.437 -6.701 0.232 -1.166 C11 3XJ 12 3XJ C12 C9 C 0 1 Y N N -11.266 49.274 -12.040 -5.351 0.501 -1.203 C12 3XJ 13 3XJ C13 C10 C 0 1 N N N -14.638 49.493 -13.880 -8.717 -0.634 0.013 C13 3XJ 14 3XJ O7 O5 O 0 1 N N N -0.003 48.396 -9.423 6.234 -0.535 2.040 O7 3XJ 15 3XJ C14 C11 C 0 1 N N R -2.283 48.109 -9.956 3.977 -0.099 1.288 C14 3XJ 16 3XJ O8 O6 O 0 1 N N N -2.655 50.709 -6.818 2.802 -3.078 -1.402 O8 3XJ 17 3XJ C15 C12 C 0 1 N N R -3.061 48.535 -7.787 4.330 -1.325 -0.742 C15 3XJ 18 3XJ O2 O7 O 0 1 N N N -15.206 48.807 -14.762 -9.208 -1.141 1.001 O2 3XJ 19 3XJ O1 O8 O 0 1 N N N -9.388 46.350 -11.976 -2.602 0.975 -1.140 O1 3XJ 20 3XJ N N1 N 0 1 N N N -8.351 48.300 -12.027 -2.314 0.155 0.904 N 3XJ 21 3XJ C3 C13 C 0 1 Y N N -7.041 47.979 -11.616 -0.928 0.332 0.827 C3 3XJ 22 3XJ C2 C14 C 0 1 Y N N -6.073 48.956 -11.646 -0.077 -0.557 1.470 C2 3XJ 23 3XJ C1 C15 C 0 1 Y N N -4.813 48.712 -11.186 1.291 -0.382 1.395 C1 3XJ 24 3XJ CL CL1 CL 0 0 N N N -5.010 44.923 -10.083 1.623 2.908 -0.860 CL 3XJ 25 3XJ C C16 C 0 1 Y N N -4.470 47.471 -10.672 1.816 0.679 0.672 C 3XJ 26 3XJ O O9 O 0 1 N N N -3.214 47.127 -10.218 3.163 0.851 0.598 O 3XJ 27 3XJ C18 C17 C 0 1 N N S -1.043 47.449 -9.452 5.428 0.387 1.304 C18 3XJ 28 3XJ C17 C18 C 0 1 N N S -1.240 46.846 -8.114 5.942 0.481 -0.136 C17 3XJ 29 3XJ C16 C19 C 0 1 N N S -1.869 47.833 -7.181 5.795 -0.888 -0.809 C16 3XJ 30 3XJ C19 C20 C 0 1 N N N -3.619 49.671 -6.964 4.185 -2.718 -1.359 C19 3XJ 31 3XJ H19 H1 H 0 1 N N N -15.932 50.749 -13.751 -10.436 -0.534 -0.970 H19 3XJ 32 3XJ H6 H2 H 0 1 N N N -7.448 45.926 -11.069 -1.064 2.093 -0.389 H6 3XJ 33 3XJ H8 H3 H 0 1 N N N -11.048 46.528 -14.026 -4.486 -0.646 1.874 H8 3XJ 34 3XJ H9 H4 H 0 1 N N N -13.273 47.317 -14.724 -6.897 -1.116 1.945 H9 3XJ 35 3XJ H13 H5 H 0 1 N N N -2.578 47.913 -5.391 7.125 -0.522 -2.292 H13 3XJ 36 3XJ H14 H6 H 0 1 N N N -0.286 45.899 -6.726 7.487 1.719 0.290 H14 3XJ 37 3XJ H10 H7 H 0 1 N N N -12.951 50.593 -11.993 -7.324 0.476 -2.014 H10 3XJ 38 3XJ H11 H8 H 0 1 N N N -10.703 49.833 -11.307 -4.914 0.956 -2.080 H11 3XJ 39 3XJ H15 H9 H 0 1 N N N 0.791 47.985 -9.103 5.961 -0.648 2.961 H15 3XJ 40 3XJ H H10 H 0 1 N N N -2.022 48.602 -10.904 3.619 -0.208 2.312 H 3XJ 41 3XJ H18 H11 H 0 1 N N N -3.024 51.413 -6.298 2.635 -3.952 -1.782 H18 3XJ 42 3XJ H12 H12 H 0 1 N N N -3.860 47.790 -7.917 3.713 -0.617 -1.296 H12 3XJ 43 3XJ H7 H13 H 0 1 N N N -8.494 49.261 -12.263 -2.715 -0.191 1.717 H7 3XJ 44 3XJ H5 H14 H 0 1 N N N -6.315 49.932 -12.040 -0.485 -1.386 2.030 H5 3XJ 45 3XJ H4 H15 H 0 1 N N N -4.072 49.497 -11.223 1.952 -1.074 1.895 H4 3XJ 46 3XJ H3 H16 H 0 1 N N N -0.778 46.645 -10.154 5.478 1.370 1.773 H3 3XJ 47 3XJ H2 H17 H 0 1 N N N -1.979 46.042 -8.247 5.361 1.222 -0.684 H2 3XJ 48 3XJ H1 H18 H 0 1 N N N -1.114 48.612 -7.001 6.417 -1.617 -0.290 H1 3XJ 49 3XJ H16 H19 H 0 1 N N N -4.511 50.075 -7.465 4.730 -3.442 -0.753 H16 3XJ 50 3XJ H17 H20 H 0 1 N N N -3.896 49.293 -5.969 4.590 -2.712 -2.371 H17 3XJ 51 # 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 3XJ O2 C13 DOUB N N 1 3XJ C9 C8 DOUB Y N 2 3XJ C9 C10 SING Y N 3 3XJ C13 C10 SING N N 4 3XJ C13 O3 SING N N 5 3XJ C8 C7 SING Y N 6 3XJ C10 C11 DOUB Y N 7 3XJ C7 C6 SING N N 8 3XJ C7 C12 DOUB Y N 9 3XJ C11 C12 SING Y N 10 3XJ C6 N SING N N 11 3XJ C6 O1 DOUB N N 12 3XJ N C3 SING N N 13 3XJ C2 C3 DOUB Y N 14 3XJ C2 C1 SING Y N 15 3XJ C3 C4 SING Y N 16 3XJ C1 C DOUB Y N 17 3XJ C4 C5 DOUB Y N 18 3XJ C C5 SING Y N 19 3XJ C O SING N N 20 3XJ C5 CL SING N N 21 3XJ O C14 SING N N 22 3XJ C14 C18 SING N N 23 3XJ C14 O4 SING N N 24 3XJ C18 O7 SING N N 25 3XJ C18 C17 SING N N 26 3XJ O4 C15 SING N N 27 3XJ C17 O6 SING N N 28 3XJ C17 C16 SING N N 29 3XJ C15 C16 SING N N 30 3XJ C15 C19 SING N N 31 3XJ C16 O5 SING N N 32 3XJ C19 O8 SING N N 33 3XJ O3 H19 SING N N 34 3XJ C4 H6 SING N N 35 3XJ C8 H8 SING N N 36 3XJ C9 H9 SING N N 37 3XJ O5 H13 SING N N 38 3XJ O6 H14 SING N N 39 3XJ C11 H10 SING N N 40 3XJ C12 H11 SING N N 41 3XJ O7 H15 SING N N 42 3XJ C14 H SING N N 43 3XJ O8 H18 SING N N 44 3XJ C15 H12 SING N N 45 3XJ N H7 SING N N 46 3XJ C2 H5 SING N N 47 3XJ C1 H4 SING N N 48 3XJ C18 H3 SING N N 49 3XJ C17 H2 SING N N 50 3XJ C16 H1 SING N N 51 3XJ C19 H16 SING N N 52 3XJ C19 H17 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 3XJ SMILES ACDLabs 12.01 "O=C(O)c1ccc(cc1)C(=O)Nc3ccc(OC2OC(C(O)C(O)C2O)CO)c(Cl)c3" 3XJ InChI InChI 1.03 "InChI=1S/C20H20ClNO9/c21-12-7-11(22-18(27)9-1-3-10(4-2-9)19(28)29)5-6-13(12)30-20-17(26)16(25)15(24)14(8-23)31-20/h1-7,14-17,20,23-26H,8H2,(H,22,27)(H,28,29)/t14-,15-,16+,17+,20+/m1/s1" 3XJ InChIKey InChI 1.03 HIKPKPMJGGGESU-BAPGRXHISA-N 3XJ SMILES_CANONICAL CACTVS 3.385 "OC[C@H]1O[C@H](Oc2ccc(NC(=O)c3ccc(cc3)C(O)=O)cc2Cl)[C@@H](O)[C@@H](O)[C@@H]1O" 3XJ SMILES CACTVS 3.385 "OC[CH]1O[CH](Oc2ccc(NC(=O)c3ccc(cc3)C(O)=O)cc2Cl)[CH](O)[CH](O)[CH]1O" 3XJ SMILES_CANONICAL "OpenEye OEToolkits" 1.9.2 "c1cc(ccc1C(=O)Nc2ccc(c(c2)Cl)O[C@@H]3[C@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O)C(=O)O" 3XJ SMILES "OpenEye OEToolkits" 1.9.2 "c1cc(ccc1C(=O)Nc2ccc(c(c2)Cl)OC3C(C(C(C(O3)CO)O)O)O)C(=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 3XJ "SYSTEMATIC NAME" ACDLabs 12.01 "4-{[3-chloro-4-(alpha-D-mannopyranosyloxy)phenyl]carbamoyl}benzoic acid" 3XJ "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.9.2 "4-[[3-chloranyl-4-[(2R,3S,4S,5S,6R)-6-(hydroxymethyl)-3,4,5-tris(oxidanyl)oxan-2-yl]oxy-phenyl]carbamoyl]benzoic acid" # loop_ _pdbx_chem_comp_audit.comp_id _pdbx_chem_comp_audit.action_type _pdbx_chem_comp_audit.date _pdbx_chem_comp_audit.processing_site 3XJ "Create component" 2014-12-06 EBI 3XJ "Initial release" 2015-05-20 RCSB #