data_9WN # _chem_comp.id 9WN _chem_comp.name "(2R)-2-(alpha-D-glucopyranosyloxy)-3-hydroxypropanoic acid" _chem_comp.type D-saccharide _chem_comp.pdbx_type ATOMS _chem_comp.formula "C9 H16 O9" _chem_comp.mon_nstd_parent_comp_id GLC _chem_comp.pdbx_synonyms ;(2~{R})-2-[(2~{R},3~{R},4~{S},5~{S},6~{R})-6-(hydroxymethyl)-3,4,5-tris(oxidanyl)oxan-2-yl]oxy-3-oxidanyl-propanoic acid; (2R)-2-(alpha-D-glucosyloxy)-3-hydroxypropanoic acid; (2R)-2-(D-glucosyloxy)-3-hydroxypropanoic acid; (2R)-2-(glucosyloxy)-3-hydroxypropanoic acid ; _chem_comp.pdbx_formal_charge 0 _chem_comp.pdbx_initial_date 2017-07-20 _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 268.218 _chem_comp.one_letter_code ? _chem_comp.three_letter_code 9WN _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 5OIW _chem_comp.pdbx_subcomponent_list ? _chem_comp.pdbx_processing_site EBI # # 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 9WN ;(2~{R})-2-[(2~{R},3~{R},4~{S},5~{S},6~{R})-6-(hydroxymethyl)-3,4,5-tris(oxidanyl)oxan-2-yl]oxy-3-oxidanyl-propanoic acid ; PDB ? 2 9WN "(2R)-2-(alpha-D-glucosyloxy)-3-hydroxypropanoic acid" PDB ? 3 9WN "(2R)-2-(D-glucosyloxy)-3-hydroxypropanoic acid" PDB ? 4 9WN "(2R)-2-(glucosyloxy)-3-hydroxypropanoic acid" 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 9WN C10 C10 C 0 1 N N N 33.501 22.913 32.686 -2.194 -1.271 -1.370 C10 9WN 1 9WN C6 C01 C 0 1 N N N 35.732 18.464 35.416 2.331 -2.383 0.500 C6 9WN 2 9WN C5 C02 C 0 1 N N R 35.148 19.900 35.566 1.608 -1.083 0.143 C5 9WN 3 9WN C4 C03 C 0 1 N N S 35.627 20.515 36.877 2.637 0.025 -0.096 C4 9WN 4 9WN C3 C04 C 0 1 N N S 34.807 21.719 37.203 1.903 1.336 -0.394 C3 9WN 5 9WN C2 C05 C 0 1 N N R 33.360 21.408 37.219 0.962 1.658 0.771 C2 9WN 6 9WN C1 C06 C 0 1 N N R 32.915 20.929 35.832 -0.002 0.487 0.976 C1 9WN 7 9WN C09 C09 C 0 1 N N R 32.932 21.711 33.471 -1.888 -0.597 -0.031 C09 9WN 8 9WN C12 C12 C 0 1 N N N 31.480 21.479 32.997 -3.107 0.148 0.447 C12 9WN 9 9WN O5 O07 O 0 1 N N N 33.700 19.761 35.463 0.745 -0.707 1.218 O5 9WN 10 9WN O1 O08 O 0 1 N N N 33.078 21.958 34.852 -0.803 0.319 -0.195 O1 9WN 11 9WN O11 O11 O 0 1 N N N 34.889 22.992 32.848 -2.664 -0.292 -2.299 O11 9WN 12 9WN O13 O13 O 0 1 N N N 30.488 21.626 33.757 -4.223 -0.525 0.768 O13 9WN 13 9WN O14 O14 O 0 1 N N N 31.280 21.161 31.790 -3.080 1.353 0.542 O14 9WN 14 9WN O2 O15 O 0 1 N N N 32.567 22.526 37.557 0.219 2.842 0.471 O2 9WN 15 9WN O3 O16 O 0 1 N N N 35.226 22.285 38.419 2.855 2.392 -0.546 O3 9WN 16 9WN O4 O17 O 0 1 N N N 36.975 20.883 36.660 3.464 -0.323 -1.208 O4 9WN 17 9WN O6 O18 O 0 1 N N N 35.355 17.703 36.524 1.380 -3.444 0.609 O6 9WN 18 9WN H1A H1 H 0 1 N N N 33.040 23.840 33.059 -1.288 -1.735 -1.758 H1A 9WN 19 9WN H2A H2 H 0 1 N N N 33.268 22.791 31.618 -2.961 -2.033 -1.226 H2A 9WN 20 9WN H61 H3 H 0 1 N N N 35.340 18.000 34.499 3.055 -2.622 -0.279 H61 9WN 21 9WN H62 H4 H 0 1 N N N 36.829 18.516 35.360 2.849 -2.261 1.451 H62 9WN 22 9WN H5 H5 H 0 1 N N N 35.520 20.513 34.732 1.018 -1.232 -0.762 H5 9WN 23 9WN H4 H6 H 0 1 N N N 35.543 19.773 37.684 3.254 0.147 0.794 H4 9WN 24 9WN H3 H7 H 0 1 N N N 34.976 22.454 36.403 1.325 1.230 -1.312 H3 9WN 25 9WN H2 H8 H 0 1 N N N 33.180 20.594 37.936 1.546 1.814 1.678 H2 9WN 26 9WN H1 H9 H 0 1 N N N 31.854 20.645 35.893 -0.646 0.692 1.831 H1 9WN 27 9WN H10 H10 H 0 1 N N N 33.519 20.823 33.194 -1.615 -1.355 0.703 H10 9WN 28 9WN H11 H11 H 0 1 N N N 35.223 23.735 32.360 -2.878 -0.649 -3.171 H11 9WN 29 9WN H12 H12 H 0 1 N N N 29.689 21.463 33.270 -4.979 -0.004 1.069 H12 9WN 30 9WN HO2 H13 H 0 1 N Y N 32.820 22.847 38.415 -0.398 3.105 1.167 HO2 9WN 31 9WN HO3 H14 H 0 1 N Y N 34.696 23.049 38.613 2.459 3.253 -0.737 HO3 9WN 32 9WN HO4 H15 H 0 1 N Y N 37.328 21.275 37.450 4.140 0.336 -1.417 HO4 9WN 33 9WN HO6 H16 H 0 1 N Y N 35.707 16.825 36.440 1.769 -4.300 0.834 HO6 9WN 34 # # 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 9WN O14 C12 DOUB N N 1 9WN C10 O11 SING N N 2 9WN C10 C09 SING N N 3 9WN C12 C09 SING N N 4 9WN C12 O13 SING N N 5 9WN C09 O1 SING N N 6 9WN O1 C1 SING N N 7 9WN C6 C5 SING N N 8 9WN C6 O6 SING N N 9 9WN O5 C5 SING N N 10 9WN O5 C1 SING N N 11 9WN C5 C4 SING N N 12 9WN C1 C2 SING N N 13 9WN O4 C4 SING N N 14 9WN C4 C3 SING N N 15 9WN C3 C2 SING N N 16 9WN C3 O3 SING N N 17 9WN C2 O2 SING N N 18 9WN C10 H1A SING N N 19 9WN C10 H2A SING N N 20 9WN C6 H61 SING N N 21 9WN C6 H62 SING N N 22 9WN C5 H5 SING N N 23 9WN C4 H4 SING N N 24 9WN C3 H3 SING N N 25 9WN C2 H2 SING N N 26 9WN C1 H1 SING N N 27 9WN C09 H10 SING N N 28 9WN O11 H11 SING N N 29 9WN O13 H12 SING N N 30 9WN O2 HO2 SING N N 31 9WN O3 HO3 SING N N 32 9WN O4 HO4 SING N N 33 9WN O6 HO6 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 9WN InChI InChI 1.03 "InChI=1S/C9H16O9/c10-1-3-5(12)6(13)7(14)9(17-3)18-4(2-11)8(15)16/h3-7,9-14H,1-2H2,(H,15,16)/t3-,4-,5-,6+,7-,9-/m1/s1" 9WN InChIKey InChI 1.03 DDXCFDOPXBPUJC-CECBSOHTSA-N 9WN SMILES_CANONICAL CACTVS 3.385 "OC[C@H]1O[C@H](O[C@H](CO)C(O)=O)[C@H](O)[C@@H](O)[C@@H]1O" 9WN SMILES CACTVS 3.385 "OC[CH]1O[CH](O[CH](CO)C(O)=O)[CH](O)[CH](O)[CH]1O" 9WN SMILES_CANONICAL "OpenEye OEToolkits" 2.0.6 "C([C@@H]1[C@H]([C@@H]([C@H]([C@H](O1)O[C@H](CO)C(=O)O)O)O)O)O" 9WN SMILES "OpenEye OEToolkits" 2.0.6 "C(C1C(C(C(C(O1)OC(CO)C(=O)O)O)O)O)O" # _pdbx_chem_comp_identifier.comp_id 9WN _pdbx_chem_comp_identifier.type "SYSTEMATIC NAME" _pdbx_chem_comp_identifier.program "OpenEye OEToolkits" _pdbx_chem_comp_identifier.program_version 2.0.6 _pdbx_chem_comp_identifier.identifier ;(2~{R})-2-[(2~{R},3~{R},4~{S},5~{S},6~{R})-6-(hydroxymethyl)-3,4,5-tris(oxidanyl)oxan-2-yl]oxy-3-oxidanyl-propanoic acid ; # _pdbx_chem_comp_related.comp_id 9WN _pdbx_chem_comp_related.related_comp_id GLC _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 9WN C6 GLC C6 "Carbohydrate core" 2 9WN C5 GLC C5 "Carbohydrate core" 3 9WN C4 GLC C4 "Carbohydrate core" 4 9WN C3 GLC C3 "Carbohydrate core" 5 9WN C2 GLC C2 "Carbohydrate core" 6 9WN C1 GLC C1 "Carbohydrate core" 7 9WN O5 GLC O5 "Carbohydrate core" 8 9WN O1 GLC O1 "Carbohydrate core" 9 9WN O2 GLC O2 "Carbohydrate core" 10 9WN O3 GLC O3 "Carbohydrate core" 11 9WN O4 GLC O4 "Carbohydrate core" 12 9WN O6 GLC O6 "Carbohydrate core" 13 9WN HO2 GLC HO2 "Carbohydrate core" 14 9WN HO3 GLC HO3 "Carbohydrate core" 15 9WN HO4 GLC HO4 "Carbohydrate core" 16 9WN HO6 GLC HO6 "Carbohydrate core" 17 9WN H61 GLC H61 "Carbohydrate core" 18 9WN H62 GLC H62 "Carbohydrate core" 19 9WN H5 GLC H5 "Carbohydrate core" 20 9WN H4 GLC H4 "Carbohydrate core" 21 9WN H3 GLC H3 "Carbohydrate core" 22 9WN H2 GLC H2 "Carbohydrate core" 23 9WN H1 GLC H1 "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 9WN "CARBOHYDRATE ISOMER" D PDB ? 9WN "CARBOHYDRATE RING" pyranose PDB ? 9WN "CARBOHYDRATE ANOMER" alpha PDB ? 9WN "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 9WN "Create component" 2017-07-20 EBI 9WN "Initial release" 2018-08-08 RCSB 9WN "Other modification" 2020-07-03 RCSB 9WN "Modify parent residue" 2020-07-17 RCSB 9WN "Modify name" 2020-07-17 RCSB 9WN "Modify synonyms" 2020-07-17 RCSB 9WN "Modify internal type" 2020-07-17 RCSB 9WN "Modify linking type" 2020-07-17 RCSB 9WN "Modify atom id" 2020-07-17 RCSB 9WN "Modify component atom id" 2020-07-17 RCSB 9WN "Modify leaving atom flag" 2020-07-17 RCSB ##