Cucurbitacin E

Base Information

• Chemical Name: Cucurbitacin E
• CAS No.: 18444-66-1
• Molecular Formula: C32H44O8
• Molecular Weight: 556.697
• Hs Code.: 29153900
• European Community (EC) Number: 242-325-2
• UNII: V8A45XYI21
• ChEMBL ID: CHEMBL455056
• DSSTox Substance ID: DTXSID601030496
• Metabolomics Workbench ID: 34412
• Nikkaji Number: J14.209C
• NSC Number: 521775,106399
• Pharos Ligand ID: QXP38ND5MR26
• Wikidata: Q5192451
• Wikipedia: Cucurbitacin_E
• Mol file: 18444-66-1.mol

Synonyms:cucurbitacin E;NSC 106399;NSC-106399

Chemical Property of Cucurbitacin E

Chemical Property:

• Vapor Pressure: 1.84E-23mmHg at 25°C
• Melting Point: 228-234 °C
• Refractive Index: 1.578
• Boiling Point: 712.615 °C at 760 mmHg
• PKA: 8.51±0.70(Predicted)
• Flash Point: 224.446 °C
• PSA: 138.20000
• Density: 1.249 g/cm³
• LogP: 4.19020
• Storage Temp.: ?20°C
• Solubility.: DMSO: soluble15mg/mL, clear
• XLogP3: 3.2
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 6
• Exact Mass: 556.30361836
• Heavy Atom Count: 40
• Complexity: 1270

Purity/Quality:

99% ^*data from raw suppliers

Cucurbitacin E ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 25-22
• Safety Statements: 1-22-45-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)OC(C)(C)C=CC(=O)C(C)(C1C(CC2(C1(CC(=O)C3(C2CC=C4C3C=C(C(=O)C4(C)C)O)C)C)C)O)O
• Isomeric SMILES: CC(=O)OC(C)(C)/C=C/C(=O)[C@@](C)([C@H]1[C@@H](C[C@@]2([C@@]1(CC(=O)[C@@]3([C@H]2CC=C4[C@H]3C=C(C(=O)C4(C)C)O)C)C)C)O)O
• Description: Cucurbitacin E is a plant-derived triterpene that has diverse biological activities. At a concentration of 10 pM, it reduces MPP+-induced death of neuronal PC12 cells through inhibition of autophagy in vitro. Cucurbitacin E inhibits growth of T24 bladder, MDA-MB-468 and MCF-7 breast, PC3 prostate, and colorectal cancer cell lines (IC50s = 50-1,000 nM) through induction of G2/M arrest and apoptosis. It increases bilirubin binding to human serum albumin (HSA) in human plasma in a dose-dependent manner. Cucurbitacin E also inhibits depolymerization of actin filaments isolated from rabbit skeletal muscle actin and in HeLa cells.
• Uses: Cucurbitacin E is a biochemical compound from the family of Cucurbitacins. Cucurbitacin E is a highly oxidated steroid consisting of a tetracyclic triterpene. Cucurbitacin E is known to possess broad spectrum of potential anti-inflammatory, antitumor andantioxidant effects. Cucurbitacin E has been used as a cofilin inhibitor. It is also used as a F-actin stabilizer to prevent membrane-associated periodic skeleton (MPS) loss and protect from axonal fragmentation.

Technology Process of Cucurbitacin E

There total 6 articles about Cucurbitacin E which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

cucurbitacin E, 2-O-β-D-glucopyranoside → cucurbitacin E (18444-66-1)

Guidance literature:

With β-glucosidase enzyme; water; at 37 ℃; for 72h; pH=5; Enzymatic reaction; acetate buffer;

Reference yield:

cucurbitacin B (6199-67-3,59015-72-4) → cucurbitacin E (18444-66-1)

Guidance literature:

With bromobenzene; N,N-dimethyl acetamide; sodium acetate; palladium diacetate; at 80 ℃; for 24h; Sealed tube;

DOI:10.1021/acs.jnatprod.5b00054

Reference yield:

→ cucurbitacin E (18444-66-1)

Guidance literature:

With bismuth(III) oxide;

upstream raw materials:

cucurbitacin B

Downstream raw materials:

23,24-dihydrocucurbitacin E

cucurbitacin I

Refernces

• 1、 Nakashima, Souichi,Matsuda, Hisashi,Kurume, Ai,Oda, Yoshimi,Nakamura, Seikou,Yamashita, Masayuki,Yoshikawa, Masayuki. "Cucurbitacin E as a new inhibitor of cofilin phosphorylation in human leukemia U937 cells". . p. 2994 - 2997. Retrieved 2010.
• 2、 -. "CUCURBITACIN COMPOUNDS". Page/Page column 7-8. . Retrieved 2008/06/13.