CHEBI:79078 - aspalathin

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ChEBI Name aspalathin
ChEBI ID CHEBI:79078
Definition A member of the class of dihydrochalcones that is the 2-C-β-D-glucopyranide of phloroglucinol and which is substituted at position 4 by a 3-(3,4-dihydroxyphenyl)propanoyl group. A metabolite of red bush, Aspalathus linearis (and present in the herbal tea made from the leaves), aspalathin exhibits significant hypoglycemic activity.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information ChemicalBook:CB61553321, ZINC000095910950
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Formula C21H24O11
Net Charge 0
Average Mass 452.40870
Monoisotopic Mass 452.13186
InChI InChI=1S/C21H24O11/c22-7-14-17(28)19(30)20(31)21(32-14)16-13(27)6-12(26)15(18(16)29)10(24)4-2-8-1-3-9(23)11(25)5-8/h1,3,5-6,14,17,19-23,25-31H,2,4,7H2/t14-,17-,19+,20-,21+/m1/s1
InChIKey VCPUQYKWJRESOC-VJXVFPJBSA-N
SMILES OC[C@H]1O[C@H]([C@H](O)[C@@H](O)[C@@H]1O)c1c(O)cc(O)c(C(=O)CCc2ccc(O)c(O)c2)c1O
Roles Classification
Chemical Role(s): antioxidant
A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides.
Biological Role(s): EC 1.17.3.2 (xanthine oxidase) inhibitor
An EC 1.17.3.* (oxidoreductase acting on CH or CH2 with oxygen as acceptor) inhibitor that interferes with the action of xanthine oxidase (EC 1.17.3.2).
plant metabolite
Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
Application(s): hypoglycemic agent
A drug which lowers the blood glucose level.
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ChEBI Ontology
Outgoing aspalathin (CHEBI:79078) has role antioxidant (CHEBI:22586)
aspalathin (CHEBI:79078) has role EC 1.17.3.2 (xanthine oxidase) inhibitor (CHEBI:35634)
aspalathin (CHEBI:79078) has role hypoglycemic agent (CHEBI:35526)
aspalathin (CHEBI:79078) has role plant metabolite (CHEBI:76924)
aspalathin (CHEBI:79078) is a C-glycosyl compound (CHEBI:20857)
aspalathin (CHEBI:79078) is a catechols (CHEBI:33566)
aspalathin (CHEBI:79078) is a dihydrochalcones (CHEBI:71230)
aspalathin (CHEBI:79078) is a polyketide (CHEBI:26188)
aspalathin (CHEBI:79078) is a polyphenol (CHEBI:26195)
IUPAC Name
(1S)-1,5-anhydro-1-{3-[3-(3,4-dihydroxyphenyl)propanoyl]-2,4,6-trihydroxyphenyl}-D-glucitol
Synonyms Sources
1-(3-C-β-D-glucopyranosyl-2,4,6-trihydroxyphenyl)-3-(3,4-dihydroxyphenyl)-1-propanone HMDB
3-(3,4-dihydroxyphenyl)-1-(3-β-D-glucopyranosyl-2,4,6-trihydroxyphenyl)-1-propanone LIPID MAPS
3-(3,4-dihydroxyphenyl)-3'-β-D-glucopyranosyl-2',4',6'-trihydroxypropiophenone ChEBI
Manual Xrefs Databases
Aspalathin Wikipedia
HMDB0030851 HMDB
LMPK12120529 LIPID MAPS
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Registry Number Type Source
1412711 Reaxys Registry Number Reaxys
Citations Waiting for Citations
Last Modified
26 January 2023