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
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
| Molecular Formula | C19H22O6 |
| Molecular Weight | 346.3744 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 6 / 6 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
DescriptionSources: http://dx.doi.org/10.3389/fphar.2016.00472
Sources: http://dx.doi.org/10.3389/fphar.2016.00472
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
Sources: https://doi.org/10.1135/cccc19602777
Curator's Comment: first isolated from artichoke (Cynara scolymus L.)
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: CHEMBL4541 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16945528 |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Preventing | Unknown Approved UseUnknown |
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| Preventing | Unknown Approved UseUnknown |
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| Preventing | Unknown Approved UseUnknown |
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/20118544
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/10862830
Curator's Comment: Cynaropicrin strongly inhibited TNF-alpha release from lipopolysaccharide-stimulated murine macrophage, RAW264.7 cells, and differentiated human macrophage, U937 cells, proved to produce notable amount of TNF-alpha. It also potently attenuated the accumulation of NO released from lipopolysaccharide- and interferon-gamma-stimulated RAW264.7 cells in a dose-dependent manner. In addition, the immunosuppressive effects of the compound on lymphocyte proliferation in response to mitogenic stimuli were examined. Cynaropicrin also dose-dependently suppressed the proliferation of lymphocytes from splenocytes and interleukin-2-sensitive cytotoxic T lymphocyte, CTLL-2 cells, stimulated by lipopolysaccharide, concanavalin A, phytohemagglutinin and interleukin-2.
Unknown
| Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 20:12:46 GMT 2025
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on
Mon Mar 31 20:12:46 GMT 2025
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| Record UNII |
M9233789I9
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| Record Status |
Validated (UNII)
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| Record Version |
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Cynaropicrin
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DTXSID20957143
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M9233789I9
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