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.
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Formula C21H24O11
Net Charge 0
Average Mass 452.40870
Monoisotopic Mass 452.132
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.
(via catechol )
genotoxin
A role played by a chemical compound to induce direct or indirect DNA damage. Such damage can potentially lead to the formation of a malignant tumour, but DNA damage does not lead inevitably to the creation of cancerous cells.
(via catechol )
allelochemical
A class of secondary metabolites developed by many plants to influence the behaviour, growth or survival of herbivores, and thus acting as a defence against herbivory.
(via catechol )
Application(s): hypoglycemic agent
A drug which lowers the blood glucose level.
View more via ChEBI Ontology
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 catechol (CHEBI:18135)
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
Database Links Databases
Aspalathin Wikipedia
HMDB30851 HMDB
LMPK12120529 LIPID MAPS
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Registry Number Type Source
1412711 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
19083477 PubMed citation Europe PMC
19188054 PubMed citation Europe PMC
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20039677 PubMed citation Europe PMC
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22571468 PubMed citation Europe PMC
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23238530 PubMed citation Europe PMC
24261664 PubMed citation Europe PMC
24268738 PubMed citation Europe PMC
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4290475 PubMed citation Europe PMC
IND44576840 Agricola citation Europe PMC
Last Modified
04 July 2014