CHEBI:68327 - robinetinidol

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ChEBI Name robinetinidol
ChEBI ID CHEBI:68327
Definition A pentahydroxyflavan that is (2S)-flavan substituted by hydroxy groups at positions 3, 7, 3', 4' and 5'. Isolated from Acacia mearnsii, it exhibits inhibitory activity against α-amylase and lipase.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C15H14O6
Net Charge 0
Average Mass 290.26810
InChI InChI=1S/C15H14O6/c16-9-2-1-7-3-12(19)15(21-13(7)6-9)8-4-10(17)14(20)11(18)5-8/h1-2,4-6,12,15-20H,3H2/t12-,15+/m0/s1
InChIKey GMPPKSLKMRADRM-SWLSCSKDSA-N
SMILES O[C@H]1Cc2ccc(O)cc2O[C@@H]1c1cc(O)c(O)c(O)c1
Metabolite of Species Details
Acacia mearnsii (NCBI:139012) Found in bark (BTO:0001301). Spray-dried aqueous extract of bark See: PubMed
Roles Classification
Biological Role(s): plant metabolite
Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
EC 3.2.1.1 (alpha-amylase) inhibitor
An EC 3.2.1.* (glycosidase) inhibitor that interferes with the action of alpha-amylase (EC 3.2.1.1).
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ChEBI Ontology
Outgoing robinetinidol (CHEBI:68327) has parent hydride (2S)-flavan (CHEBI:36103)
robinetinidol (CHEBI:68327) has role EC 3.2.1.1 (α-amylase) inhibitor (CHEBI:50627)
robinetinidol (CHEBI:68327) has role plant metabolite (CHEBI:76924)
robinetinidol (CHEBI:68327) is a pentahydroxyflavan (CHEBI:72584)
Incoming 4'-O-methylrobinetinidol 3'-O-β-D-glucopyranoside (CHEBI:68328) has functional parent robinetinidol (CHEBI:68327)
robinetinidol-(4α,8)-catechin (CHEBI:68333) has functional parent robinetinidol (CHEBI:68327)
robinetinidol-(4α,8)-gallocatechin (CHEBI:68332) has functional parent robinetinidol (CHEBI:68327)
IUPAC Name
5-[(2R,3S)-3,7-dihydroxy-3,4-dihydro-2-chromen-2-yl]benzene-1,2,3-triol
Database Links Databases
LMPK12020017 LIPID MAPS
Robinetinidol Wikipedia
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Registry Number Type Source
39544 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
21192716 PubMed citation CiteXplore
21660093 PubMed citation CiteXplore
21799697 PubMed citation CiteXplore
22063672 PubMed citation CiteXplore
22917955 PubMed citation CiteXplore
Last Modified
02 June 2015