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CHEBI:9144 - silibinin

ChEBI IDCHEBI:9144
ChEBI Namesilibinin
Stars
DefinitionA flavonolignan isolated from milk thistle, Silybum marianum, that has been shown to exhibit antioxidant and antineoplastic activities.
Last Modified6 February 2018
DownloadsMolfile
FormulaC25H22O10
Net Charge0
Average Mass482.441
Monoisotopic Mass482.12130
SMILES[H][C@]1(c2ccc(O)c(OC)c2)Oc2cc([C@@]3([H])Oc4cc(O)cc(O)c4C(=O)[C@@H]3O)ccc2O[C@@H]1CO
InChIInChI=1S/C25H22O10/c1-32-17-6-11(2-4-14(17)28)24-20(10-26)33-16-5-3-12(7-18(16)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
InChIKeySEBFKMXJBCUCAI-HKTJVKLFSA-N
Wikipedia
Roles Classification
Chemical Role:
antioxidant  A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides.
Biological Role:
plant metabolite  Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
Applications:
antineoplastic agent  A substance that inhibits or prevents the proliferation of neoplasms.
hepatoprotective agent  Any compound that is able to prevent damage to the liver.
ChEBI Ontology
Outgoing Relation(s)
silibinin (CHEBI:9144) has role antineoplastic agent (CHEBI:35610)
silibinin (CHEBI:9144) has role antioxidant (CHEBI:22586)
silibinin (CHEBI:9144) has role hepatoprotective agent (CHEBI:62868)
silibinin (CHEBI:9144) has role plant metabolite (CHEBI:76924)
silibinin (CHEBI:9144) is a aromatic ether (CHEBI:35618)
silibinin (CHEBI:9144) is a benzodioxine (CHEBI:64096)
silibinin (CHEBI:9144) is a flavonolignan (CHEBI:72709)
silibinin (CHEBI:9144) is a polyphenol (CHEBI:26195)
silibinin (CHEBI:9144) is a secondary α-hydroxy ketone (CHEBI:2468)
IUPAC Name 
(2R,3R)-3,5,7-trihydroxy-2-[(2R,3R)-3-(4-hydroxy-3-methoxyphenyl)-2-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl]-2,3-dihydro-4H-chromen-4-one
INNs  Source
silibininKEGG DRUG
silibininaWHO MedNet
silibinineWHO MedNet
silibininumWHO MedNet
Synonyms  Source
SilymarinKEGG COMPOUND
SilibininKEGG COMPOUND
SilibinineHMDB
KarsilHMDB
FlavobinHMDB
SilybinKEGG COMPOUND
Manual XrefsDatabases
C07610KEGG COMPOUND
SilibininWikipedia
D08515KEGG DRUG
HMDB0030583HMDB
CN102727484Patent
C00001003KNApSAcK
Registry NumbersSources
Reaxys:1632852Reaxys
CAS:22888-70-6KEGG COMPOUND
CAS:22888-70-6ChemIDplus
Citations