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CHEBI:79078 - aspalathin

ChEBI IDCHEBI:79078
ChEBI Nameaspalathin
Stars
DefinitionA 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.
Last Modified26 January 2023
SubmitterGareth Owen
DownloadsMolfile
FormulaC21H24O11
Net Charge0
Average Mass452.412
Monoisotopic Mass452.13186
SMILESO=C(CCc1ccc(O)c(O)c1)c1c(O)cc(O)c([C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)c1O
InChIInChI=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
InChIKeyVCPUQYKWJRESOC-VJXVFPJBSA-N
Wikipedia
Roles Classification
Chemical Role:
antioxidant  A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides.
Biological Roles:
plant metabolite  Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
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).
Application:
hypoglycemic agent  A drug which lowers the blood glucose level.
ChEBI Ontology
Outgoing Relation(s)
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  Source
1-(3-C-β-D-glucopyranosyl-2,4,6-trihydroxyphenyl)-3-(3,4-dihydroxyphenyl)-1-propanoneHMDB
3-(3,4-dihydroxyphenyl)-1-(3-β-D-glucopyranosyl-2,4,6-trihydroxyphenyl)-1-propanoneLIPID MAPS
3-(3,4-dihydroxyphenyl)-3'-β-D-glucopyranosyl-2',4',6'-trihydroxypropiophenoneChEBI
Manual XrefsDatabases
AspalathinWikipedia
HMDB0030851HMDB
LMPK12120529LIPID MAPS
Registry NumbersSources
Reaxys:1412711Reaxys
Citations