CHEBI:9144 - silibinin

Main ChEBI Ontology Automatic Xrefs Reactions Pathways Models
ChEBI Name silibinin
ChEBI ID CHEBI:9144
Definition A flavonolignan isolated from milk thistle, Silybum marianum, that has been shown to exhibit antioxidant and antineoplastic activities.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information ChemicalBook:CB5505863, eMolecules:1936005, eMolecules:29917755, Selleckchem:Silibinin(Silybin), ZINC000002033589
Download Molfile XML SDF
Wikipedia License
Silibinin (INN), also known as silybin (both from Silybum, the generic name of the plant from which it is extracted), is the major active constituent of silymarin, a standardized extract of the milk thistle, containing a mixture of flavonolignans consisting of silibinin, isosilibinin, silychristin, silidianin, and others. Silibinin itself is a mixture of two diastereomers, silybin A and silybin B, in approximately equimolar ratio. Silibinin is used in pure forms as a medication, and more frequently as an active ingredient in milk thistle–derived herbal supplements.
Read full article at Wikipedia
Formula C25H22O10
Net Charge 0
Average Mass 482.43620
Monoisotopic Mass 482.12130
InChI InChI=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
InChIKey SEBFKMXJBCUCAI-HKTJVKLFSA-N
SMILES [H][C@@]1(Oc2cc(ccc2O[C@@H]1CO)[C@@]1([H])Oc2cc(O)cc(O)c2C(=O)[C@@H]1O)c1ccc(O)c(OC)c1
Roles Classification
Chemical Role(s): antioxidant
A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides.
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.
Application(s): 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.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing 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 Sources
silibinin KEGG DRUG
silibinina WHO MedNet
silibinine WHO MedNet
silibininum WHO MedNet
Synonyms Sources
Flavobin HMDB
Karsil HMDB
Silibinin KEGG COMPOUND
Silibinine HMDB
Silybin KEGG COMPOUND
Silymarin KEGG COMPOUND
Manual Xrefs Databases
C00001003 KNApSAcK
C07610 KEGG COMPOUND
CN102727484 Patent
D08515 KEGG DRUG
HMDB0030583 HMDB
Silibinin Wikipedia
View more database links
Registry Numbers Types Sources
1632852 Reaxys Registry Number Reaxys
22888-70-6 CAS Registry Number ChemIDplus
Citations Waiting for Citations
Last Modified
06 February 2018