data_XMM # _chem_comp.id XMM _chem_comp.name "5-bromo-4-chloro-1H-indol-3-yl alpha-D-mannopyranoside" _chem_comp.type D-saccharide _chem_comp.pdbx_type ATOMS _chem_comp.formula "C14 H15 Br Cl N O6" _chem_comp.mon_nstd_parent_comp_id MAN _chem_comp.pdbx_synonyms ;(2R,3S,4S,5S,6R)-2-(5-BROMO-4-CHLORO-1H-INDOL-3-YLOXY)-TETRAHYDRO-6-(HYDROXYMETHYL)-2H-PYRAN-3,4,5-TRIOL; (5-BROMO-4-CHLORO-3-INDOLYL)-Alpha-D-MANNOSE; 5-bromo-4-chloro-1H-indol-3-yl alpha-D-mannoside; 5-bromo-4-chloro-1H-indol-3-yl D-mannoside; 5-bromo-4-chloro-1H-indol-3-yl mannoside ; _chem_comp.pdbx_formal_charge 0 _chem_comp.pdbx_initial_date 2005-04-26 _chem_comp.pdbx_modified_date 2020-07-17 _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 408.629 _chem_comp.one_letter_code ? _chem_comp.three_letter_code XMM _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 1ZGS _chem_comp.pdbx_subcomponent_list ? _chem_comp.pdbx_processing_site RCSB # # 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 XMM "(2R,3S,4S,5S,6R)-2-(5-BROMO-4-CHLORO-1H-INDOL-3-YLOXY)-TETRAHYDRO-6-(HYDROXYMETHYL)-2H-PYRAN-3,4,5-TRIOL" PDB ? 2 XMM "(5-BROMO-4-CHLORO-3-INDOLYL)-Alpha-D-MANNOSE" PDB ? 3 XMM "5-bromo-4-chloro-1H-indol-3-yl alpha-D-mannoside" PDB ? 4 XMM "5-bromo-4-chloro-1H-indol-3-yl D-mannoside" PDB ? 5 XMM "5-bromo-4-chloro-1H-indol-3-yl mannoside" PDB ? # # 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 XMM O2 O2 O 0 1 N N N 5.353 -2.919 17.109 -4.751 0.091 -1.827 O2 XMM 1 XMM C2 C2 C 0 1 N N S 3.937 -3.010 17.237 -3.445 0.613 -1.572 C2 XMM 2 XMM C3 C3 C 0 1 N N S 3.706 -3.955 18.402 -3.510 1.628 -0.426 C3 XMM 3 XMM O3 O3 O 0 1 N N N 4.298 -5.239 18.146 -4.494 2.621 -0.720 O3 XMM 4 XMM C4 C4 C 0 1 N N S 4.395 -3.339 19.604 -3.891 0.887 0.862 C4 XMM 5 XMM O4 O4 O 0 1 N N N 4.160 -4.074 20.790 -3.814 1.786 1.970 O4 XMM 6 XMM C5 C5 C 0 1 N N R 3.951 -1.921 19.891 -2.918 -0.274 1.076 C5 XMM 7 XMM O5 O5 O 0 1 N N N 3.849 -1.086 18.736 -3.011 -1.188 -0.015 O5 XMM 8 XMM C6 C6 C 0 1 N N N 5.158 -1.447 20.655 -3.268 -0.998 2.377 C6 XMM 9 XMM O6 O6 O 0 1 N N N 5.007 -0.087 20.946 -2.289 -2.006 2.640 O6 XMM 10 XMM C1 C1 C 0 1 N N R 3.309 -1.634 17.519 -2.506 -0.529 -1.175 C1 XMM 11 XMM O1 O1 O 0 1 N N N 1.921 -1.930 17.652 -1.209 0.001 -0.894 O1 XMM 12 XMM C7 C7 C 0 1 Y N N 0.752 -1.207 17.693 -0.367 -1.063 -0.776 C7 XMM 13 XMM C8 C8 C 0 1 Y N N -0.522 -1.556 18.467 1.072 -1.010 -0.494 C8 XMM 14 XMM C9 C9 C 0 1 Y N N -1.452 -0.452 18.101 1.514 -2.345 -0.462 C9 XMM 15 XMM N1 N1 N 0 1 Y N N -0.859 0.475 17.193 0.421 -3.143 -0.716 N1 XMM 16 XMM C11 C11 C 0 1 Y N N 0.270 -0.143 17.133 -0.695 -2.361 -0.901 C11 XMM 17 XMM C10 C10 C 0 1 Y N N -0.881 -2.642 19.352 1.976 0.030 -0.262 C10 XMM 18 XMM CL CL CL 0 1 N N N 0.128 -3.697 19.640 1.436 1.679 -0.294 CL XMM 19 XMM C13 C13 C 0 1 Y N N -2.313 -2.634 19.931 3.300 -0.261 -0.013 C13 XMM 20 XMM BR BR BR 0 1 N N N -3.006 -3.511 20.858 4.529 1.142 0.295 BR XMM 21 XMM C14 C14 C 0 1 Y N N -2.801 -1.575 19.425 3.736 -1.580 0.013 C14 XMM 22 XMM C12 C12 C 0 1 Y N N -2.753 -0.506 18.683 2.855 -2.615 -0.209 C12 XMM 23 XMM HO2 HO2 H 0 1 N Y N 5.497 -2.327 16.379 -4.662 -0.546 -2.549 HO2 XMM 24 XMM H2 H2 H 0 1 N N N 3.463 -3.376 16.296 -3.066 1.101 -2.470 H2 XMM 25 XMM H3 H3 H 0 1 N N N 2.612 -4.100 18.566 -2.537 2.102 -0.302 H3 XMM 26 XMM HO3 HO3 H 0 1 N Y N 4.153 -5.830 18.875 -4.221 3.051 -1.542 HO3 XMM 27 XMM H4 H4 H 0 1 N N N 5.474 -3.352 19.326 -4.907 0.502 0.774 H4 XMM 28 XMM HO4 HO4 H 0 1 N Y N 4.591 -3.688 21.543 -4.436 2.504 1.791 HO4 XMM 29 XMM H5 H5 H 0 1 N N N 2.945 -1.884 20.372 -1.900 0.113 1.138 H5 XMM 30 XMM H61 H61 H 0 1 N N N 5.349 -2.057 21.567 -4.250 -1.461 2.283 H61 XMM 31 XMM H62 H62 H 0 1 N N N 6.111 -1.663 20.119 -3.281 -0.282 3.199 H62 XMM 32 XMM HO6 HO6 H 0 1 N Y N 5.768 0.212 21.428 -2.547 -2.437 3.466 HO6 XMM 33 XMM H1 H1 H 0 1 N N N 3.509 -0.876 16.725 -2.436 -1.243 -1.996 H1 XMM 34 XMM HN1 HN1 H 0 1 N N N -1.155 1.330 16.723 0.436 -4.112 -0.758 HN1 XMM 35 XMM H11 H11 H 0 1 N N N 0.983 0.348 16.449 -1.686 -2.733 -1.114 H11 XMM 36 XMM H14 H14 H 0 1 N N N -3.810 -1.593 19.869 4.776 -1.795 0.209 H14 XMM 37 XMM H12 H12 H 0 1 N N N -3.605 0.184 18.574 3.206 -3.637 -0.186 H12 XMM 38 # # 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 XMM O2 C2 SING N N 1 XMM O2 HO2 SING N N 2 XMM C2 C3 SING N N 3 XMM C2 C1 SING N N 4 XMM C2 H2 SING N N 5 XMM C3 O3 SING N N 6 XMM C3 C4 SING N N 7 XMM C3 H3 SING N N 8 XMM O3 HO3 SING N N 9 XMM C4 O4 SING N N 10 XMM C4 C5 SING N N 11 XMM C4 H4 SING N N 12 XMM O4 HO4 SING N N 13 XMM C5 O5 SING N N 14 XMM C5 C6 SING N N 15 XMM C5 H5 SING N N 16 XMM O5 C1 SING N N 17 XMM C6 O6 SING N N 18 XMM C6 H61 SING N N 19 XMM C6 H62 SING N N 20 XMM O6 HO6 SING N N 21 XMM C1 O1 SING N N 22 XMM C1 H1 SING N N 23 XMM O1 C7 SING N N 24 XMM C7 C8 SING Y N 25 XMM C7 C11 DOUB Y N 26 XMM C8 C9 DOUB Y N 27 XMM C8 C10 SING Y N 28 XMM C9 N1 SING Y N 29 XMM C9 C12 SING Y N 30 XMM N1 C11 SING Y N 31 XMM N1 HN1 SING N N 32 XMM C11 H11 SING N N 33 XMM C10 CL SING N N 34 XMM C10 C13 DOUB Y N 35 XMM C13 BR SING N N 36 XMM C13 C14 SING Y N 37 XMM C14 C12 DOUB Y N 38 XMM C14 H14 SING N N 39 XMM C12 H12 SING N N 40 # # 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 XMM SMILES ACDLabs 10.04 "Brc3ccc2c(c(OC1OC(C(O)C(O)C1O)CO)cn2)c3Cl" XMM SMILES_CANONICAL CACTVS 3.341 "OC[C@H]1O[C@H](Oc2c[nH]c3ccc(Br)c(Cl)c23)[C@@H](O)[C@@H](O)[C@@H]1O" XMM SMILES CACTVS 3.341 "OC[CH]1O[CH](Oc2c[nH]c3ccc(Br)c(Cl)c23)[CH](O)[CH](O)[CH]1O" XMM SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 "c1cc(c(c2c1[nH]cc2O[C@@H]3[C@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O)Cl)Br" XMM SMILES "OpenEye OEToolkits" 1.5.0 "c1cc(c(c2c1[nH]cc2OC3C(C(C(C(O3)CO)O)O)O)Cl)Br" XMM InChI InChI 1.03 "InChI=1S/C14H15BrClNO6/c15-5-1-2-6-9(10(5)16)7(3-17-6)22-14-13(21)12(20)11(19)8(4-18)23-14/h1-3,8,11-14,17-21H,4H2/t8-,11-,12+,13+,14+/m1/s1" XMM InChIKey InChI 1.03 OPIFSICVWOWJMJ-HAAGFXOZSA-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 XMM "SYSTEMATIC NAME" ACDLabs 10.04 "5-bromo-4-chloro-1H-indol-3-yl alpha-D-mannopyranoside" XMM "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "(2R,3S,4S,5S,6R)-2-[(5-bromo-4-chloro-1H-indol-3-yl)oxy]-6-(hydroxymethyl)oxane-3,4,5-triol" # _pdbx_chem_comp_related.comp_id XMM _pdbx_chem_comp_related.related_comp_id MAN _pdbx_chem_comp_related.relationship_type "Carbohydrate core" _pdbx_chem_comp_related.details ? # # loop_ _pdbx_chem_comp_atom_related.ordinal _pdbx_chem_comp_atom_related.comp_id _pdbx_chem_comp_atom_related.atom_id _pdbx_chem_comp_atom_related.related_comp_id _pdbx_chem_comp_atom_related.related_atom_id _pdbx_chem_comp_atom_related.related_type 1 XMM C1 MAN C1 "Carbohydrate core" 2 XMM C2 MAN C2 "Carbohydrate core" 3 XMM C3 MAN C3 "Carbohydrate core" 4 XMM C4 MAN C4 "Carbohydrate core" 5 XMM C5 MAN C5 "Carbohydrate core" 6 XMM C6 MAN C6 "Carbohydrate core" 7 XMM O1 MAN O1 "Carbohydrate core" 8 XMM O2 MAN O2 "Carbohydrate core" 9 XMM O3 MAN O3 "Carbohydrate core" 10 XMM O4 MAN O4 "Carbohydrate core" 11 XMM O5 MAN O5 "Carbohydrate core" 12 XMM O6 MAN O6 "Carbohydrate core" 13 XMM H1 MAN H1 "Carbohydrate core" 14 XMM H2 MAN H2 "Carbohydrate core" 15 XMM H3 MAN H3 "Carbohydrate core" 16 XMM H4 MAN H4 "Carbohydrate core" 17 XMM H5 MAN H5 "Carbohydrate core" 18 XMM H61 MAN H61 "Carbohydrate core" 19 XMM H62 MAN H62 "Carbohydrate core" 20 XMM HO2 MAN HO2 "Carbohydrate core" 21 XMM HO3 MAN HO3 "Carbohydrate core" 22 XMM HO4 MAN HO4 "Carbohydrate core" 23 XMM HO6 MAN HO6 "Carbohydrate core" # # loop_ _pdbx_chem_comp_feature.comp_id _pdbx_chem_comp_feature.type _pdbx_chem_comp_feature.value _pdbx_chem_comp_feature.source _pdbx_chem_comp_feature.support XMM "CARBOHYDRATE ISOMER" D PDB ? XMM "CARBOHYDRATE RING" pyranose PDB ? XMM "CARBOHYDRATE ANOMER" alpha PDB ? XMM "CARBOHYDRATE PRIMARY CARBONYL GROUP" aldose PDB ? # # loop_ _pdbx_chem_comp_audit.comp_id _pdbx_chem_comp_audit.action_type _pdbx_chem_comp_audit.date _pdbx_chem_comp_audit.processing_site XMM "Create component" 2005-04-26 RCSB XMM "Modify descriptor" 2011-06-04 RCSB XMM "Other modification" 2020-07-03 RCSB XMM "Modify parent residue" 2020-07-17 RCSB XMM "Modify name" 2020-07-17 RCSB XMM "Modify synonyms" 2020-07-17 RCSB XMM "Modify linking type" 2020-07-17 RCSB XMM "Modify leaving atom flag" 2020-07-17 RCSB ##