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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

[H][C@@]12C[C@H](O)C(=C)[C@]1([H])[C@@]3([H])OC(=O)C(=C)[C@]3([H])[C@H](CC2=C)OC(=O)C(=C)CO

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

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

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

Curator's Comment: first isolated from artichoke (Cynara scolymus L.)

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Preventing
Unknown

Approved Use

Unknown
Preventing
Unknown

Approved Use

Unknown
Preventing
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Cynaropicrin attenuates UVB-induced oxidative stress via the AhR-Nrf2-Nqo1 pathway.
2015 Apr 16
Patents

Patents

Sample Use Guides

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
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 Fri Dec 15 20:38:54 GMT 2023
Edited
by admin
on Fri Dec 15 20:38:54 GMT 2023
Record UNII
M9233789I9
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CYNAROPICRIN
Common Name English
2-PROPENOIC ACID, 2-(HYDROXYMETHYL)-, (3AR,4S,6AR,8S,9AR,9BR)-DODECAHYDRO-8-HYDROXY-3,6,9-TRIS(METHYLENE)-2-OXOAZULENO(4,5-B)FURAN-4-YL ESTER
Common Name English
CYNAROPIKRIN
Common Name English
2-PROPENOIC ACID, 2-(HYDROXYMETHYL)-, DODECAHYDRO-8-HYDROXY-3,6,9-TRIS(METHYLENE)-2-OXOAZULENO(4,5-B)FURAN-4-YL ESTER, (3AR-(3A.ALPHA.,4.ALPHA.,6A.ALPHA.,8.BETA.,9A.ALPHA.,9B.BETA.))-
Common Name English
Code System Code Type Description
WIKIPEDIA
Cynaropicrin
Created by admin on Fri Dec 15 20:38:54 GMT 2023 , Edited by admin on Fri Dec 15 20:38:54 GMT 2023
PRIMARY
EPA CompTox
DTXSID20957143
Created by admin on Fri Dec 15 20:38:54 GMT 2023 , Edited by admin on Fri Dec 15 20:38:54 GMT 2023
PRIMARY
FDA UNII
M9233789I9
Created by admin on Fri Dec 15 20:38:54 GMT 2023 , Edited by admin on Fri Dec 15 20:38:54 GMT 2023
PRIMARY
CAS
35730-78-0
Created by admin on Fri Dec 15 20:38:54 GMT 2023 , Edited by admin on Fri Dec 15 20:38:54 GMT 2023
PRIMARY
PUBCHEM
119093
Created by admin on Fri Dec 15 20:38:54 GMT 2023 , Edited by admin on Fri Dec 15 20:38:54 GMT 2023
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Related Record Type Details
PARENT -> CONSTITUENT ALWAYS PRESENT