data_AFE # _chem_comp.id AFE _chem_comp.name "5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-3-yl 6-deoxy-alpha-L-mannopyranoside" _chem_comp.type NON-POLYMER _chem_comp.pdbx_type HETAIN _chem_comp.formula "C21 H20 O10" _chem_comp.mon_nstd_parent_comp_id ? _chem_comp.pdbx_synonyms "afzelin; kaempherol 3-O-alpha-rhamnoside" _chem_comp.pdbx_formal_charge 0 _chem_comp.pdbx_initial_date 2012-04-19 _chem_comp.pdbx_modified_date 2020-05-26 _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 432.378 _chem_comp.one_letter_code ? _chem_comp.three_letter_code AFE _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 4EL9 _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 AFE O9 O9 O 0 1 N N N 31.236 5.195 5.138 4.410 2.490 1.129 O9 AFE 1 AFE C23 C23 C 0 1 N N R 32.064 5.063 6.241 3.283 1.752 0.650 C23 AFE 2 AFE C22 C22 C 0 1 N N R 33.403 4.539 5.829 2.130 2.714 0.352 C22 AFE 3 AFE O22 O22 O 0 1 N N N 33.893 5.296 4.791 2.560 3.700 -0.589 O22 AFE 4 AFE C24 C24 C 0 1 N N R 32.230 6.395 6.869 3.664 1.014 -0.638 C24 AFE 5 AFE O61 O61 O 0 1 N N N 31.017 6.850 7.340 4.691 0.061 -0.356 O61 AFE 6 AFE C25 C25 C 0 1 N N S 33.191 6.272 8.009 2.431 0.291 -1.186 C25 AFE 7 AFE C51 C51 C 0 1 N N N 33.343 7.608 8.655 2.788 -0.399 -2.504 C51 AFE 8 AFE O7 O7 O 0 1 N N N 34.418 5.812 7.564 1.386 1.239 -1.412 O7 AFE 9 AFE C21 C21 C 0 1 N N S 34.364 4.558 6.987 0.956 1.926 -0.234 C21 AFE 10 AFE O8 O8 O 0 1 N N N 33.963 3.548 7.856 0.492 0.976 0.728 O8 AFE 11 AFE C3 C3 C 0 1 N N N 34.650 3.486 9.065 -0.719 0.400 0.493 C3 AFE 12 AFE C4 C4 C 0 1 N N N 36.125 3.352 9.096 -1.891 1.196 0.435 C4 AFE 13 AFE O2 O2 O 0 1 N N N 36.865 3.324 7.955 -1.845 2.406 0.592 O2 AFE 14 AFE C2 C2 C 0 1 N N N 33.986 3.518 10.260 -0.813 -0.947 0.306 C2 AFE 15 AFE C11 C11 C 0 1 Y N N 32.513 3.571 10.450 0.416 -1.759 0.364 C11 AFE 16 AFE C12 C12 C 0 1 Y N N 31.642 2.972 9.409 1.315 -1.597 1.422 C12 AFE 17 AFE C13 C13 C 0 1 Y N N 30.290 2.957 9.604 2.462 -2.359 1.472 C13 AFE 18 AFE C14 C14 C 0 1 Y N N 29.719 3.495 10.872 2.726 -3.286 0.472 C14 AFE 19 AFE O5 O5 O 0 1 N N N 28.360 3.467 11.073 3.858 -4.035 0.525 O5 AFE 20 AFE C15 C15 C 0 1 Y N N 30.531 4.001 11.857 1.836 -3.451 -0.582 C15 AFE 21 AFE C16 C16 C 0 1 Y N N 32.005 4.016 11.632 0.684 -2.698 -0.637 C16 AFE 22 AFE O1 O1 O 0 1 N N N 34.661 3.420 11.458 -1.985 -1.561 0.071 O1 AFE 23 AFE C9 C9 C 0 1 Y N N 36.022 3.296 11.542 -3.152 -0.888 0.004 C9 AFE 24 AFE C8 C8 C 0 1 Y N N 36.618 3.214 12.889 -4.342 -1.556 -0.241 C8 AFE 25 AFE C7 C7 C 0 1 Y N N 37.971 3.086 13.001 -5.533 -0.849 -0.307 C7 AFE 26 AFE O4 O4 O 0 1 N N N 38.477 3.023 14.263 -6.694 -1.511 -0.547 O4 AFE 27 AFE C6 C6 C 0 1 Y N N 38.841 3.046 11.781 -5.551 0.530 -0.130 C6 AFE 28 AFE C5 C5 C 0 1 Y N N 38.260 3.133 10.541 -4.374 1.214 0.114 C5 AFE 29 AFE C10 C10 C 0 1 Y N N 36.783 3.260 10.419 -3.166 0.507 0.177 C10 AFE 30 AFE O3 O3 O 0 1 N N N 39.012 3.089 9.410 -4.389 2.560 0.287 O3 AFE 31 AFE HO9 HO9 H 0 1 N N N 30.390 5.528 5.414 4.240 2.982 1.943 HO9 AFE 32 AFE H23 H23 H 0 1 N N N 31.621 4.372 6.974 2.972 1.030 1.405 H23 AFE 33 AFE H22 H22 H 0 1 N N N 33.279 3.495 5.505 1.816 3.203 1.274 H22 AFE 34 AFE HO22 HO22 H 0 0 N N N 34.743 4.963 4.530 1.906 4.390 -0.764 HO22 AFE 35 AFE H24 H24 H 0 1 N N N 32.644 7.094 6.127 4.024 1.731 -1.375 H24 AFE 36 AFE HO61 HO61 H 0 0 N N N 31.132 7.704 7.741 4.981 -0.444 -1.128 HO61 AFE 37 AFE H25 H25 H 0 1 N N N 32.770 5.572 8.746 2.096 -0.454 -0.464 H25 AFE 38 AFE H512 H512 H 0 0 N N N 34.048 7.531 9.496 3.586 -1.121 -2.332 H512 AFE 39 AFE H513 H513 H 0 0 N N N 33.728 8.329 7.919 1.910 -0.914 -2.894 H513 AFE 40 AFE H511 H511 H 0 0 N N N 32.365 7.949 9.026 3.122 0.347 -3.225 H511 AFE 41 AFE H21 H21 H 0 1 N N N 35.358 4.307 6.589 0.148 2.611 -0.488 H21 AFE 42 AFE H12 H12 H 0 1 N N N 32.071 2.554 8.510 1.110 -0.876 2.200 H12 AFE 43 AFE H13 H13 H 0 1 N N N 29.637 2.557 8.842 3.156 -2.234 2.289 H13 AFE 44 AFE HO5 HO5 H 0 1 N N N 28.157 3.843 11.921 3.755 -4.870 1.001 HO5 AFE 45 AFE H15 H15 H 0 1 N N N 30.110 4.381 12.776 2.045 -4.174 -1.357 H15 AFE 46 AFE H16 H16 H 0 1 N N N 32.667 4.379 12.404 -0.010 -2.830 -1.454 H16 AFE 47 AFE H8 H8 H 0 1 N N N 35.994 3.255 13.770 -4.341 -2.626 -0.380 H8 AFE 48 AFE HO4 HO4 H 0 1 N N N 37.766 3.063 14.892 -7.146 -1.815 0.252 HO4 AFE 49 AFE H6 H6 H 0 1 N N N 39.912 2.950 11.877 -6.485 1.068 -0.183 H6 AFE 50 AFE HO3 HO3 H 0 1 N N N 38.446 3.160 8.650 -4.508 2.837 1.206 HO3 AFE 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 AFE O22 C22 SING N N 1 AFE O9 C23 SING N N 2 AFE C22 C23 SING N N 3 AFE C22 C21 SING N N 4 AFE C23 C24 SING N N 5 AFE C24 O61 SING N N 6 AFE C24 C25 SING N N 7 AFE C21 O7 SING N N 8 AFE C21 O8 SING N N 9 AFE O7 C25 SING N N 10 AFE O8 C3 SING N N 11 AFE O2 C4 DOUB N N 12 AFE C25 C51 SING N N 13 AFE C3 C4 SING N N 14 AFE C3 C2 DOUB N N 15 AFE C4 C10 SING N N 16 AFE C12 C13 DOUB Y N 17 AFE C12 C11 SING Y N 18 AFE O3 C5 SING N N 19 AFE C13 C14 SING Y N 20 AFE C2 C11 SING N N 21 AFE C2 O1 SING N N 22 AFE C10 C5 DOUB Y N 23 AFE C10 C9 SING Y N 24 AFE C11 C16 DOUB Y N 25 AFE C5 C6 SING Y N 26 AFE C14 O5 SING N N 27 AFE C14 C15 DOUB Y N 28 AFE O1 C9 SING N N 29 AFE C9 C8 DOUB Y N 30 AFE C16 C15 SING Y N 31 AFE C6 C7 DOUB Y N 32 AFE C8 C7 SING Y N 33 AFE C7 O4 SING N N 34 AFE O9 HO9 SING N N 35 AFE C23 H23 SING N N 36 AFE C22 H22 SING N N 37 AFE O22 HO22 SING N N 38 AFE C24 H24 SING N N 39 AFE O61 HO61 SING N N 40 AFE C25 H25 SING N N 41 AFE C51 H512 SING N N 42 AFE C51 H513 SING N N 43 AFE C51 H511 SING N N 44 AFE C21 H21 SING N N 45 AFE C12 H12 SING N N 46 AFE C13 H13 SING N N 47 AFE O5 HO5 SING N N 48 AFE C15 H15 SING N N 49 AFE C16 H16 SING N N 50 AFE C8 H8 SING N N 51 AFE O4 HO4 SING N N 52 AFE C6 H6 SING N N 53 AFE O3 HO3 SING N N 54 # 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 AFE SMILES ACDLabs 12.01 "O=C2C(OC1OC(C(O)C(O)C1O)C)=C(Oc3cc(O)cc(O)c23)c4ccc(O)cc4" AFE InChI InChI 1.03 "InChI=1S/C21H20O10/c1-8-15(25)17(27)18(28)21(29-8)31-20-16(26)14-12(24)6-11(23)7-13(14)30-19(20)9-2-4-10(22)5-3-9/h2-8,15,17-18,21-25,27-28H,1H3/t8-,15-,17+,18+,21-/m0/s1" AFE InChIKey InChI 1.03 SOSLMHZOJATCCP-AEIZVZFYSA-N AFE SMILES_CANONICAL CACTVS 3.370 "C[C@@H]1O[C@@H](OC2=C(Oc3cc(O)cc(O)c3C2=O)c4ccc(O)cc4)[C@H](O)[C@H](O)[C@H]1O" AFE SMILES CACTVS 3.370 "C[CH]1O[CH](OC2=C(Oc3cc(O)cc(O)c3C2=O)c4ccc(O)cc4)[CH](O)[CH](O)[CH]1O" AFE SMILES_CANONICAL "OpenEye OEToolkits" 1.7.6 "C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)OC2=C(Oc3cc(cc(c3C2=O)O)O)c4ccc(cc4)O)O)O)O" AFE SMILES "OpenEye OEToolkits" 1.7.6 "CC1C(C(C(C(O1)OC2=C(Oc3cc(cc(c3C2=O)O)O)c4ccc(cc4)O)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 AFE "SYSTEMATIC NAME" ACDLabs 12.01 "5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-3-yl 6-deoxy-alpha-L-mannopyranoside" AFE "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.7.6 "2-(4-hydroxyphenyl)-3-[(2S,3R,4R,5R,6S)-6-methyl-3,4,5-tris(oxidanyl)oxan-2-yl]oxy-5,7-bis(oxidanyl)chromen-4-one" # loop_ _pdbx_chem_comp_audit.comp_id _pdbx_chem_comp_audit.action_type _pdbx_chem_comp_audit.date _pdbx_chem_comp_audit.processing_site AFE "Create component" 2012-04-19 RCSB AFE "Initial release" 2012-08-31 RCSB AFE "Modify synonyms" 2020-05-26 PDBE # 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 AFE afzelin ? ? 2 AFE "kaempherol 3-O-alpha-rhamnoside" ? ? #