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Details

Stereochemistry ABSOLUTE
Molecular Formula C19H22O6
Molecular Weight 346.3744
Optical Activity UNSPECIFIED
Defined Stereocenters 6 / 6
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CYNAROPICRIN

SMILES

OCC(=C)C(=O)O[C@H]1CC(=C)[C@@H]2C[C@H](O)C(=C)[C@@H]2[C@H]3OC(=O)C(=C)[C@H]13

InChI

InChIKey=KHSCYOFDKADJDJ-NQLMQOPMSA-N
InChI=1S/C19H22O6/c1-8-5-14(24-18(22)9(2)7-20)16-11(4)19(23)25-17(16)15-10(3)13(21)6-12(8)15/h12-17,20-21H,1-7H2/t12-,13-,14-,15-,16+,17+/m0/s1

HIDE SMILES / InChI

Description

Cynaropicrin is a sesquiterpene lactone, which has been shown to possess various biological activities and has demonstrated extraordinary pharmacologic properties. Cynaropicrin has multi-medicinal potential therapeutics evidenced not just by the scientific literature describing it, but also by the plenty number of patent applications. Cynaropicrin was found to suppress hyperlipidemia, so as it is a potent antioxidant and hence; it can play a supportive role for liver in different hepatic diseases. The mode of action in case of HCV infection occurred during the early steps of the HCV life cycle, including cell-free and cell-cell infection inhibition. Cynaropicrin may serve as a potential drug lead for treatment or prevention of human cancers. Cynaropicrin is a potent, irreversible inhibitor of the bacterial enzyme MurA (covalently binds to the thiol group of Cys115 through Michael addition reaction). MurA is important for bacterial cells since this enzyme is responsible for the first step in the cytoplasmic biosynthesis of peptidoglycan precursor molecules. Cynaropicrin possesses a marked effect on mucosal injuries, preventing acute gastritis.

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency

Conditions

ConditionModalityTargetsHighest PhaseProduct
Preventing
Unknown
Preventing
Unknown
Preventing
Unknown

PubMed

Patents

Sample Use Guides

In Vivo Use Guide
for rats (gastric mucosal injury): (artichoke leaf extract, dextrin, chlorogenic acid, cynaropicrin and sofalcone) was given orally in a volume of 1ml per 100g of body weight.
Route of Administration: Oral
In Vitro Use Guide
Unknown