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3-Epiursolic acid

CAS# 989-30-0

3-Epiursolic acid

2D Structure

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3D structure

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3-Epiursolic acid

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Chemical Properties of 3-Epiursolic acid

Cas No. 989-30-0 SDF Download SDF
PubChem ID 7163177 Appearance Powder
Formula C30H48O3 M.Wt 456.7
Type of Compound Triterpenoids Storage Desiccate at -20°C
Solubility Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
Chemical Name (1S,2R,4aS,6aR,6aS,6bR,8aR,10R,12aR,14bS)-10-hydroxy-1,2,6a,6b,9,9,12a-heptamethyl-2,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydro-1H-picene-4a-carboxylic acid
SMILES CC1CCC2(CCC3(C(=CCC4C3(CCC5C4(CCC(C5(C)C)O)C)C)C2C1C)C)C(=O)O
Standard InChIKey WCGUUGGRBIKTOS-XHINXETDSA-N
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Source of 3-Epiursolic acid

The leaves of Eriobotrya japonica Thunb.

Biological Activity of 3-Epiursolic acid

Description1. 3-Epiursolic acid shows inhibition on Cathepsins L (catL), the IC50 value of 6.5 uM, cathepsins L (catL) and B play an important role in tumor progression and have been considered promising therapeutic targets in the development of novel anticancer agents. 2. 3-Epiursolic acid may have antiinflammatory activity.
TargetsImmunology & Inflammation related

3-Epiursolic acid Dilution Calculator

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3-Epiursolic acid Molarity Calculator

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Preparing Stock Solutions of 3-Epiursolic acid

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 2.1896 mL 10.9481 mL 21.8962 mL 43.7924 mL 54.7405 mL
5 mM 0.4379 mL 2.1896 mL 4.3792 mL 8.7585 mL 10.9481 mL
10 mM 0.219 mL 1.0948 mL 2.1896 mL 4.3792 mL 5.4741 mL
50 mM 0.0438 mL 0.219 mL 0.4379 mL 0.8758 mL 1.0948 mL
100 mM 0.0219 mL 0.1095 mL 0.219 mL 0.4379 mL 0.5474 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

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References on 3-Epiursolic acid

Triterpenoids as novel natural inhibitors of human cathepsin L.[Pubmed:25238076]

Chem Biodivers. 2014 Sep;11(9):1354-63.

Cathepsins L (catL) and B play an important role in tumor progression and have been considered promising therapeutic targets in the development of novel anticancer agents. Using a bioactivity-guided fractionation, a series of triterpenoids was identified as a new class of competitive inhibitors towards cathepsin L with affinity values in micromolar range. Among the 14 compounds evaluated, the most promising were 3-Epiursolic acid (3), 3-(hydroxyimino)oleanolic acid (9), and 3-(hydroxyimino)masticadienoic acid (13) with IC50 values of 6.5, 2.4, and 2.6 muM on catL, respectively. Most of the evaluated triterpenoids do not inhibit cathepsin B. Thus, the evaluated compounds exhibit a great potential to help in the design of new inhibitors with enhanced potency and affinity towards catL. Docking studies were performed in order to gain insight on the binding mode and SAR of these compounds.

Antiinflammatory activity and chemical composition of extracts of Verbena officinalis.[Pubmed:10960904]

Phytother Res. 2000 Sep;14(6):463-5.

In an attempt to locate the biologically active fraction(s) of the plant Verbena officinalis Linn. (Verbenaceae), a preliminary screening of successive petroleum ether, chloroform and methanol extracts of aerial parts for antiinflammatory activity using carrageenan paw oedema model was carried out. All three extracts were found to exhibit antiinflammatory activity with the chloroform extract being the most active. Chemical investigations of petroleum ether and chloroform extracts led to the isolation of beta-sitosterol, ursolic acid, oleanolic acid, 3-Epiursolic acid, 3-epioleanolic acid, and minor triterpenoids of derivatives of ursolic acid and oleanolic acids. Chromatographic purification of the methanol extract yielded two iridoid glucosides, verbenalin and hastatoside, a phenylpropanoid glycoside, verbascoside and beta-sitosterol-D-glucoside.

Description

3-Epiursolic Acid is a triterpenoid isolated from Myrtaceae, acts as a competitive inhibitor of cathepsin L (ICIC50, 6.5 μM; Ki, 19.5 μM), with no obvious effect on cathepsin B.

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