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CHEBI:145829 - trilobatin

ChEBI IDCHEBI:145829
ChEBI Nametrilobatin
Stars
DefinitionAn aryl β-D-glucoside that is phloretin attached to a β-D-glucopyranosyl residue at position 4' via a glycosidic linkage. It is isolated from the leaves of the Chinese sweet tea Lithocarpus polystachyus and exhibits significant anti-hyperglycemic, anti-oxidative and anti-inflammatory properties.
Last Modified19 August 2020
Submittermwilliams
DownloadsMolfile
FormulaC21H24O10
Net Charge0
Average Mass436.413
Monoisotopic Mass436.13695
SMILESO=C(CCc1ccc(O)cc1)c1c(O)cc(O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)cc1O
InChIInChI=1S/C21H24O10/c22-9-16-18(27)19(28)20(29)21(31-16)30-12-7-14(25)17(15(26)8-12)13(24)6-3-10-1-4-11(23)5-2-10/h1-2,4-5,7-8,16,18-23,25-29H,3,6,9H2/t16-,18-,19+,20-,21-/m1/s1
InChIKeyGSTCPEBQYSOEHV-QNDFHXLGSA-N
Species of MetaboliteComponentSourceComments
Lithocarpus polystachyus (IPNI:358942-1) leaf (BTO:0000713) PubMed (25053100)
Malus trilobata (ncbitaxon:106570) leaf (BTO:0000713) DOI (10.1039/JR9610004133)
Lithocarpus litseifolius (ncbitaxon:425828) leaf (BTO:0000713) DOI (10.1080/00021369.1982.10865357)
Roles Classification
Chemical Role:
antioxidant  A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides.
Biological Roles:
sweetening agent  Substance that sweeten food, beverages, medications, etc.
plant metabolite  Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
Applications:
sweetening agent  Substance that sweeten food, beverages, medications, etc.
anti-inflammatory agent  Any compound that has anti-inflammatory effects.
ChEBI Ontology
Outgoing Relation(s)
trilobatin (CHEBI:145829) has functional parent phloretin (CHEBI:17276)
trilobatin (CHEBI:145829) has role anti-inflammatory agent (CHEBI:67079)
trilobatin (CHEBI:145829) has role antioxidant (CHEBI:22586)
trilobatin (CHEBI:145829) has role plant metabolite (CHEBI:76924)
trilobatin (CHEBI:145829) has role sweetening agent (CHEBI:50505)
trilobatin (CHEBI:145829) is a aryl β-D-glucoside (CHEBI:28749)
trilobatin (CHEBI:145829) is a dihydrochalcones (CHEBI:71230)
trilobatin (CHEBI:145829) is a monosaccharide derivative (CHEBI:63367)
IUPAC Name 
3,5-dihydroxy-4-[3-(4-hydroxyphenyl)propanoyl]phenyl β-D-glucopyranoside
Synonyms  Source
p-phlorizinChemIDplus
p-phloridzinChemIDplus
1-(4-(β-D-glucopyranosyloxy)-2,6-dihydroxyphenyl)-3-(4-hydroxyphenyl)-1-propanoneChemIDplus
phloretin-4'-β-D-glucosideChEBI
phloretin-4'-β-D-glucopyranosideChEBI
UniProt Name  Source
trilobatinUniProt
Manual XrefsDatabases
FDB016580FooDB
LMPK12120518LIPID MAPS
C00007991KNApSAcK
HMDB0037505HMDB
Registry NumbersSources
CAS:4192-90-9ChemIDplus
Citations