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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
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

Targets

Primary TargetPharmacologyConditionPotency
Target ID: P09917
Gene ID: 240.0
Gene Symbol: ALOX5
Target Organism: Homo sapiens (Human)
PubMed

PubMed

TitleDatePubMed
Effect of the flavanolignans of Silybum marianum L. on lipid peroxidation in rat liver microsomes and freshly isolated hepatocytes.
1992 Feb-Mar
Stimulatory effects of silibinin and silicristin from the milk thistle Silybum marianum on kidney cells.
1999 Sep
Silychristin, a Flavonolignan Derived From the Milk Thistle, Is a Potent Inhibitor of the Thyroid Hormone Transporter MCT8.
2016 Apr
Silychristin derivatives conjugated with coniferylalcohols from silymarin and their pancreatic α-amylase inhibitory activity.
2020 Mar

Sample Use Guides

Silicristin is a potent inhibitor of the thyroid hormone transporter MCT8 with IC50 value of approximately 100 nM.
Name Type Language
SILICRISTIN
INN   MART.  
INN  
Official Name English
silicristin [INN]
Common Name English
SILICRISTIN [MART.]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C1745
Created by admin on Sat Dec 16 16:27:22 GMT 2023 , Edited by admin on Sat Dec 16 16:27:22 GMT 2023
NCI_THESAURUS C2081
Created by admin on Sat Dec 16 16:27:22 GMT 2023 , Edited by admin on Sat Dec 16 16:27:22 GMT 2023
Code System Code Type Description
ECHA (EC/EINECS)
251-720-9
Created by admin on Sat Dec 16 16:27:22 GMT 2023 , Edited by admin on Sat Dec 16 16:27:22 GMT 2023
PRIMARY
PUBCHEM
441764
Created by admin on Sat Dec 16 16:27:22 GMT 2023 , Edited by admin on Sat Dec 16 16:27:22 GMT 2023
PRIMARY
ChEMBL
CHEMBL2107543
Created by admin on Sat Dec 16 16:27:22 GMT 2023 , Edited by admin on Sat Dec 16 16:27:22 GMT 2023
PRIMARY
INN
4105
Created by admin on Sat Dec 16 16:27:22 GMT 2023 , Edited by admin on Sat Dec 16 16:27:22 GMT 2023
PRIMARY
FDA UNII
LK279ER14X
Created by admin on Sat Dec 16 16:27:22 GMT 2023 , Edited by admin on Sat Dec 16 16:27:22 GMT 2023
PRIMARY
NCI_THESAURUS
C74268
Created by admin on Sat Dec 16 16:27:22 GMT 2023 , Edited by admin on Sat Dec 16 16:27:22 GMT 2023
PRIMARY
EVMPD
SUB10519MIG
Created by admin on Sat Dec 16 16:27:22 GMT 2023 , Edited by admin on Sat Dec 16 16:27:22 GMT 2023
PRIMARY
MESH
C015504
Created by admin on Sat Dec 16 16:27:22 GMT 2023 , Edited by admin on Sat Dec 16 16:27:22 GMT 2023
PRIMARY
CAS
33889-69-9
Created by admin on Sat Dec 16 16:27:22 GMT 2023 , Edited by admin on Sat Dec 16 16:27:22 GMT 2023
PRIMARY
SMS_ID
100000083511
Created by admin on Sat Dec 16 16:27:22 GMT 2023 , Edited by admin on Sat Dec 16 16:27:22 GMT 2023
PRIMARY