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Cynaropicrin

CAT: 0804-HY-N2350-03Size: 10 mgDry Ice: NoHazardous: No
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CAT#:0804-HY-N2350-03Size:10 mg
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Description
Cynaropicrin is a sesquiterpene lactone which can inhibit tumor necrosis factor (TNF-α) release with IC50s of 8.24 and 3.18 μM for murine and human macrophage cells, respectively. Cynaropicrin also inhibits the increase of cartilage degradation factor (MMP13) and suppresses NF-κB signaling.
CAS Number
35730-78-0
UNSPSC
12352005
Hazard Statement
H317
Target
MMP; NF-κB; TNF Receptor
Type
Natural Products
Related Pathways
Apoptosis; Metabolic Enzyme/Protease; NF-κB
Applications
Cancer-Kinase/protease
Field of Research
Cancer
Assay Protocol
https://www.medchemexpress.com/Cynaropicrin.html
Concentration
10mM
Purity
99.79
Solubility
DMSO : 100 mg/mL (ultrasonic)
Smiles
C=C([C@H]1O)[C@]([C@@]2([H])C1)([H])[C@](OC3=O)([H])[C@@](C3=C)([H])[C@@H](OC(C(CO)=C)=O)CC2=C
Molecular Formula
C19H22O6
Molecular Weight
346.37
Precautions
H317
References & Citations
[1]Cho JY, et al. In vitro anti-inflammatory effects of cynaropicrin, a sesquiterpene lactone, from Saussurea lappa. Eur J Pharmacol. 2000 Jun 23;398 (3) :399-407.|[2]Masutani T, et al. Cynaropicrin is dual regulator for both degradation factors and synthesis factors in the cartilage metabolism. Life Sci. 2016 Aug 1;158:70-7.|[3]da Silva CF, et al. Activities of psilostachyin A and cynaropicrin against Trypanosoma cruzi in vitro and in vivo. Antimicrob Agents Chemother. 2013 Nov;57 (11) :5307-14.
Shipping Conditions
Blue Ice
Storage Conditions
-20°C (Powder, protect from light)
Scientific Category
Natural Products
Clinical Information
No Development Reported
Isoform
MMP-13; NF-κB; TNFRSF5/CD40

Chemical Information

Cynaropicrin

Cynaropicrin is a sesquiterpene lactone.

CAS Number35730-78-0
PubChem CID119093
IUPAC Name[(3aR,4S,6aR,8S,9aR,9bR)-8-hydroxy-3,6,9-trimethylidene-2-oxo-3a,4,5,6a,7,8,9a,9b-octahydroazuleno[4,5-b]furan-4-yl] 2-(hydroxymethyl)prop-2-enoate
Molecular FormulaC19H22O6
Molecular Weight346.4
XLogP0.6
Topological Polar Surface Area93.1
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count6
Rotatable Bond Count4
Heavy Atom Count25
Formal Charge0
Complexity690
SMILES
C=C1C[C@@H]([C@@H]2[C@@H]([C@@H]3[C@H]1C[C@@H](C3=C)O)OC(=O)C2=C)OC(=O)C(=C)CO
InChI
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
InChIKey
KHSCYOFDKADJDJ-NQLMQOPMSA-N
Chemical Structure
2D Structure
2D structure of Cynaropicrin
CAS: 35730-78-0
CID: 119093
Formula: C19H22O6
MW: 346.4
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight346.4
XLogP30.6
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count6
Rotatable Bond Count4
Exact Mass346.14163842
Monoisotopic Mass346.14163842
Topological Polar Surface Area93.1 Ų
Heavy Atom Count25
Formal Charge0
Complexity690
Isotope Atom Count0
Defined Atom Stereocenter Count6
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

Alternative Products

CatalogName
BA3538-5.1Cynaropicrin
A16915-25Cynaropicrin 25mg
A16915-10Cynaropicrin 10mg
A16915-2Cynaropicrin 2mg
A16915-50Cynaropicrin 50mg
A16915-5Cynaropicrin 5mg
A16915-1Cynaropicrin 1mg
XC160151-01Cynaropicrin - Cynara cardunculus (artichoke)
A16915-10mM-DCynaropicrin 10mM * 1mL in DMSO

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