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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
Structure of SILICRISTIN

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

HIDE SMILES / InChI

Molecular Formula C25H22O10
Molecular Weight 482.4362
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 4 / 4
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

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 TargetPharmacologyConditionPotency

PubMed

Sample Use Guides

In Vitro Use Guide
Silicristin is a potent inhibitor of the thyroid hormone transporter MCT8 with IC50 value of approximately 100 nM.
Substance Class Chemical
Record UNII
LK279ER14X
Record Status Validated (UNII)
Record Version