Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C25H22O10 |
Molecular Weight | 482.4362 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 4 / 4 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
COC1=CC(=CC=C1O)[C@@H]2OC3=C(O)C=C(C=C3[C@H]2CO)[C@H]4OC5=CC(O)=CC(O)=C5C(=O)[C@@H]4O
InChI
InChIKey=BMLIIPOXVWESJG-LMBCONBSSA-N
InChI=1S/C25H22O10/c1-33-18-6-10(2-3-15(18)28)23-14(9-26)13-4-11(5-17(30)25(13)35-23)24-22(32)21(31)20-16(29)7-12(27)8-19(20)34-24/h2-8,14,22-24,26-30,32H,9H2,1H3/t14-,22+,23+,24-/m1/s1
Silicristin is a flavonolignan isolated from Silybum marianum and has been shown to exhibit inhibitory activities against lipoxygenase and prostaglandin synthetase. It has a role as a radical scavenger, a lipoxygenase inhibitor, a prostaglandin antagonist and a metabolite. It is a flavonolignan, a member of 1-benzofurans, a polyphenol, an aromatic ether and a secondary alpha-hydroxy ketone. Silicristin is a potent inhibitor of the thyroid hormone transporter MCT8. Silicristin is a sodium pump inhibitor, it inhibited Na(+)/K(+)-ATPase (NKA) with IC50 of 110 uM. Silicristin exhibits relatively good antioxidant effectiveness against phenylglyoxylic ketyl radicals and DPPH. Silicristin protects cardiomyocytes against doxorubicin-induced oxidative stress is due mainly to their cell membrane stabilization effect, radical scavenging and iron chelating potency.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: P09917 Gene ID: 240.0 Gene Symbol: ALOX5 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/10782486 |
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Target ID: GO:0001516 Sources: https://www.ncbi.nlm.nih.gov/pubmed/118049 |
PubMed
Title | Date | PubMed |
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Effect of the flavanolignans of Silybum marianum L. on lipid peroxidation in rat liver microsomes and freshly isolated hepatocytes. | 1992 Feb-Mar |
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Stimulatory effects of silibinin and silicristin from the milk thistle Silybum marianum on kidney cells. | 1999 Sep |
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Silychristin, a Flavonolignan Derived From the Milk Thistle, Is a Potent Inhibitor of the Thyroid Hormone Transporter MCT8. | 2016 Apr |
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Silychristin derivatives conjugated with coniferylalcohols from silymarin and their pancreatic α-amylase inhibitory activity. | 2020 Mar |
Sample Use Guides
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/26910310
Silicristin is a potent inhibitor of the thyroid hormone transporter MCT8 with IC50 value of approximately 100 nM.
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NCI_THESAURUS |
C1745
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C2081
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251-720-9
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441764
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CHEMBL2107543
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4105
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LK279ER14X
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C74268
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SUB10519MIG
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C015504
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33889-69-9
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100000083511
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ACTIVE MOIETY