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CHEBI:205528 - isosilybin A

ChEBI IDCHEBI:205528
ChEBI Nameisosilybin A
Stars
Last Modified10 November 2023
SubmitterMetaboLights
DownloadsMolfile
FormulaC25H22O10
Net Charge0
Average Mass482.441
Monoisotopic Mass482.12130
SMILES[H][C@]1(c2ccc(O)c(OC)c2)Oc2ccc([C@@]3([H])Oc4cc(O)cc(O)c4C(=O)[C@@H]3O)cc2O[C@@H]1CO
InChIInChI=1S/C25H22O10/c1-32-17-6-11(2-4-14(17)28)24-20(10-26)33-18-7-12(3-5-16(18)34-24)25-23(31)22(30)21-15(29)8-13(27)9-19(21)35-25/h2-9,20,23-29,31H,10H2,1H3/t20-,23+,24-,25-/m1/s1
InChIKeyFDQAOULAVFHKBX-HKTJVKLFSA-N
Species of MetaboliteComponentSourceComments
Aspergillus iizukae (ncbitaxon:41901) - PubMed (24456525)
Silybum marianum (ncbitaxon:92921) - PubMed (17764149)
Roles Classification
Biological Roles:
PPARgamma agonist  A PPAR modulator which activates the peroxisome proliferator-activated receptor-γ.
apoptosis inducer  Any substance that induces the process of apoptosis (programmed cell death) in multi-celled organisms.
plant metabolite  Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
Aspergillus metabolite  Any fungal metabolite produced during a metabolic reaction in the mould, Aspergillus .
ChEBI Ontology
Outgoing Relation(s)
isosilybin A (CHEBI:205528) has role Aspergillus metabolite (CHEBI:76956)
isosilybin A (CHEBI:205528) has role apoptosis inducer (CHEBI:68495)
isosilybin A (CHEBI:205528) has role plant metabolite (CHEBI:76924)
isosilybin A (CHEBI:205528) has role PPARγ agonist (CHEBI:71554)
isosilybin A (CHEBI:205528) is a flavonolignan (CHEBI:72709)
IUPAC Name 
(2R,3R)-3,5,7-trihydroxy-2-[(2R,3R)-2-(4-hydroxy-3-methoxyphenyl)-3-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl]-2,3-dihydro-4H-chromen-4-one
Synonyms  Source
(2R,3R)-3,5,7-trihydroxy-2-[(2R,3R)-2-(4-hydroxy-3-methoxyphenyl)-3-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl]-2,3-dihydrochromen-4-oneSUBMITTER
(2R,3R)-3,5,7-trihydroxy-2-[(2R,3R)-2-(4-hydroxy-3-methoxyphenyl)-3-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl]-2,3-dihydro-4H-1-benzopyran-4-oneIUPAC
(+)-isosilybin AKNApSAcK
Manual XrefsDatabases
9235077ChemSpider
LMPK12140713LIPID MAPS
C00039453KNApSAcK
Citations