CHEBI:145829 - trilobatin

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ChEBI Name trilobatin
ChEBI ID CHEBI:145829
Definition An 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.
Stars This entity has been manually annotated by the ChEBI Team.
Submitter Mark Williams
Supplier Information No supplier information found for this compound.
Download Molfile XML SDF
Formula C21H24O10
Net Charge 0
Average Mass 436.413
Monoisotopic Mass 436.13695
InChI InChI=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
InChIKey GSTCPEBQYSOEHV-QNDFHXLGSA-N
SMILES O1[C@@H]([C@@H](O)[C@H](O)[C@@H](O)[C@@H]1OC2=CC(O)=C(C(O)=C2)C(=O)CCC3=CC=C(O)C=C3)CO
Metabolite of Species Details
Lithocarpus polystachyus (IPNI:358942-1) Found in leaf (BTO:0000713). See: PubMed
Malus trilobata (NCBI:txid106570) Found in leaf (BTO:0000713). See: DOI
Lithocarpus litseifolius (NCBI:txid425828) Found in leaf (BTO:0000713). See: DOI
Roles Classification
Chemical Role(s): antioxidant
A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides.
Biological Role(s): 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.
Application(s): anti-inflammatory agent
Any compound that has anti-inflammatory effects.
sweetening agent
Substance that sweeten food, beverages, medications, etc.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing 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 Sources
1-(4-(β-D-glucopyranosyloxy)-2,6-dihydroxyphenyl)-3-(4-hydroxyphenyl)-1-propanone ChemIDplus
p-phloridzin ChemIDplus
p-phlorizin ChemIDplus
phloretin-4'-β-D-glucopyranoside ChEBI
phloretin-4'-β-D-glucoside ChEBI
trilobatin UniProt
Manual Xrefs Databases
C00007991 KNApSAcK
FDB016580 FooDB
HMDB0037505 HMDB
LMPK12120518 LIPID MAPS
View more database links
Registry Number Type Source
4192-90-9 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
22792798 PubMed citation Europe PMC
23562371 PubMed citation Europe PMC
25053100 PubMed citation Europe PMC
26363372 PubMed citation Europe PMC
27893760 PubMed citation Europe PMC
28450013 PubMed citation Europe PMC
29757201 PubMed citation Europe PMC
29802645 PubMed citation Europe PMC
29865928 PubMed citation Europe PMC
31540429 PubMed citation Europe PMC
IND601124268 Agricola citation Europe PMC
IND605946551 Agricola citation Europe PMC
IND606090210 Agricola citation Europe PMC
Last Modified
19 August 2020