| Size | Price | |
|---|---|---|
| 500mg | ||
| 1g | ||
| Other Sizes |
| Targets |
The precise molecular target of 2-epi-cucurbitacin B has not been definitively identified in the available literature. As a stereoisomer of cucurbitacin B, which is known to target the JAK/STAT3 signaling pathway and the actin cytoskeleton, 2-epi-cucurbitacin B may share similar mechanisms. Cucurbitacin B is well-characterized as an inhibitor of JAK2 and STAT3 phosphorylation, as well as a disruptor of actin polymerization via the RhoA/ROCK pathway. However, the stereochemical variation at the C-2 position may alter target binding affinity and selectivity compared to cucurbitacin B. Further target identification studies are needed for this specific compound.
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|---|---|
| ln Vitro |
The compound has been isolated and identified from Ecballium elaterium, but detailed bioactivity assays have not been reported in the accessible literature. Related cucurbitacin compounds, including cucurbitacin B and its stereoisomers, generally exhibit potent cytotoxicity against various human cancer cell lines. Given that 2-epi-cucurbitacin B is a stereoisomer of cucurbitacin B, it may retain significant antiproliferative activity, but direct experimental confirmation is required. Further studies are needed to establish the specific potency and selectivity of this compound against cancer cell lines.
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| ln Vivo |
Related cucurbitacin compounds have demonstrated in vivo antitumor activity in animal models, suggesting that 2-epi-cucurbitacin B may have potential for in vivo efficacy, but direct studies are required to confirm this.
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| Enzyme Assay |
For related cucurbitacin compounds, standard assays typically involve evaluating inhibition of the JAK/STAT3 signaling pathway using techniques such as Western blot analysis to assess phosphorylation levels of JAK2 and STAT3 proteins. For target engagement studies, methods such as cellular thermal shift assay (CETSA) can be employed to confirm direct binding to putative protein targets. Additionally, molecular docking simulations using bioinformatics tools can predict binding affinities to target proteins before proceeding to experimental validation.
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| Cell Assay |
General cytotoxicity testing for cucurbitacin compounds has been performed using standard methods. A typical protocol for related compounds: (1) Culture human cancer cell lines (e.g., A-549 lung carcinoma, HCT-15 colon adenocarcinoma, or SK-OV-3 ovarian cancer cells) in appropriate media such as RPMI-1640 or DMEM supplemented with 10% fetal bovine serum; (2) Seed cells in 96-well plates at a density of 5,000-10,000 cells per well; (3) Allow cells to adhere overnight; (4) Treat with 2-epi-cucurbitacin B at various concentrations (typically 0.1-100 µM) for 48-72 hours; (5) Assess cell viability using MTT or SRB colorimetric assays; (6) Measure absorbance using a microplate reader and calculate IC50 values by regression analysis.
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| Animal Protocol |
For related cucurbitacin compounds, standard in vivo protocols typically involve administration via intraperitoneal injection or oral gavage in rodent models (e.g., mice or rats). For low water solubility compounds like 2-epi-cucurbitacin B (logP ~2.6, moderate solubility), recommended formulation strategies may include DMSO:PEG300:Tween 80:Saline (10:40:5:45) for injection or suspension in 0.5% CMC-Na for oral administration. Doses are typically determined based on preliminary toxicity studies and pharmacokinetic profiles of related compounds.
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| ADME/Pharmacokinetics |
Based on its physicochemical properties, the compound has a molecular weight of 558.7, a predicted logP of 2.6 (moderately lipophilic), a topological polar surface area (TPSA) of 138.0 Ų, with 3 hydrogen bond donors and 8 hydrogen bond acceptors. The molecular complexity is high (1210), which may present challenges for oral absorption. The Lipinski Rule of 5 is satisfied (True), indicating the compound has drug-like properties, but the Ghose Rule is violated (False), suggesting potential absorption or permeability limitations. According to ESOL prediction, the compound is classified as "moderately soluble." GI absorption is predicted to be False, indicating potentially low oral bioavailability. For in vivo formulation, solubility enhancers such as DMSO, PEG300, Tween 80, or cyclodextrins are recommended.
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| Toxicity/Toxicokinetics |
According to computational predictions, the compound violates the Brenk rule (True), which may indicate potential toxicity concerns related to structural alerts or reactive functional groups. The Pfizer 3/75 rule and GSK 4/400 rule are both violated (False), suggesting potential developability issues. Cucurbitacins as a class are known to exhibit significant cytotoxicity at low concentrations, which underlies their antitumor activity but also raises concerns for potential off-target toxicity. It should be emphasized that this compound is strictly for research use only and is not approved for human therapeutic use. According to TargetMol's product information, all products are for scientific research or drug approval purposes only and cannot be used in humans.
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| References |
| Molecular Formula |
C32H46O8
|
|---|---|
| Molecular Weight |
558.702850818634
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| Exact Mass |
558.319268
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| CAS # |
59015-72-4
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| PubChem CID |
101596930
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| Appearance |
Typically exists as solid at room temperature
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| Density |
1.23±0.1 g/cm3(Predicted)
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| Boiling Point |
229-231 °C
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| Hydrogen Bond Donor Count |
3
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| Hydrogen Bond Acceptor Count |
8
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| Rotatable Bond Count |
6
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| Heavy Atom Count |
40
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| Complexity |
1210
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| Defined Atom Stereocenter Count |
9
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| SMILES |
CC(OC(C=CC(C(C1C2(C(C3C(C(C2)=O)(C)C2CC(C(C(C2=CC3)(C)C)=O)O)(C)CC1O)C)(O)C)=O)(C)C)=O
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| InChi Key |
IXQKXEUSCPEQRD-PBMNGLKCSA-N
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| InChi Code |
InChI=1S/C32H46O8/c1-17(33)40-27(2,3)13-12-23(36)32(9,39)25-21(35)15-29(6)22-11-10-18-19(14-20(34)26(38)28(18,4)5)31(22,8)24(37)16-30(25,29)7/h10,12-13,19-22,25,34-35,39H,11,14-16H2,1-9H3/b13-12+/t19-,20-,21-,22+,25+,29+,30-,31+,32+/m1/s1
|
| Chemical Name |
[(E,6R)-6-[(2R,8S,9R,10R,13R,14S,16R,17R)-2,16-dihydroxy-4,4,9,13,14-pentamethyl-3,11-dioxo-2,7,8,10,12,15,16,17-octahydro-1H-cyclopenta[a]phenanthren-17-yl]-6-hydroxy-2-methyl-5-oxohept-3-en-2-yl] acetate
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| Synonyms |
2-Epicucurbitacin B; 2-epi-Cucurbitacin B; 59015-72-4; orb2564227;
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
Typically soluble in DMSO (e.g. 10 mM)
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|---|---|
| Solubility (In Vivo) |
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples.
Injection Formulations
Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline)(e.g. IP/IV/IM/SC) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). View More
Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] Oral Formulations
Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). View More
Oral Formulation 3: Dissolved in PEG400 (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 1.7899 mL | 8.9493 mL | 17.8987 mL | |
| 5 mM | 0.3580 mL | 1.7899 mL | 3.5797 mL | |
| 10 mM | 0.1790 mL | 0.8949 mL | 1.7899 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
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