Molecular Identity
Silibinin
(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-dihydrochromen-4-one
PubChem CID: 31553
Silibinin is a flavonolignan isolated from milk thistle, Silybum marianum, that has been shown to exhibit antioxidant and antineoplastic activities. It has a role as an antioxidant, an antineoplastic agent, a hepatoprotective agent and a plant metabolite. It is a secondary alpha-hydroxy ketone, a polyphenol, an aromatic ether, a benzodioxine and a flavonolignan.
2D Structure
Properties
C25H22O10
Molecular Formula
482.40
Molecular Weight
g/mol
482.1213
Exact Mass
Da
2.4
XLogP
Drug-like (Lipinski: < 5)
155
TPSA
May have limited oral absorption
5
H-Bond Donors
10
H-Bond Acceptors
750
Complexity
SMILES
Canonical SMILES
SMILES: COC1=C(C=CC(=C1)C2C(OC3=C(O2)C=C(C=C3)C4C(C(=O)C5=C(C=C(C=C5O4)O)O)O)CO)OIsomeric SMILES
SMILES: COC1=C(C=CC(=C1)[C@@H]2[C@H](OC3=C(O2)C=C(C=C3)[C@@H]4[C@H](C(=O)C5=C(C=C(C=C5O4)O)O)O)CO)OSynonyms(20)
silibininSilymarin IFlavobinSilybineSilibininaSilibinineSilliverSilymarine ISilibininumLegalon(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-dihydrochromen-4-oneCHEBI:9144(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-oneSilibinin a-silibinin b mixt.(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
Data from PubChem (NCBI)
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Drug Network
Trials and conditions connected to Silibinin
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