Chemical Property of Gedunin
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Chemical Property:
- Vapor Pressure:4.31E-14mmHg at 25°C
- Melting Point:218 °C(Solv: methanol (67-56-1))
- Boiling Point:594.3°Cat760mmHg
- Flash Point:313.2°C
- PSA：95.34000
- Density:1.28g/cm3
- LogP:4.56070
- Storage Temp.:Store at +4°C
- Solubility.:Chloroform (Slightly)
- XLogP3:4.2
- Hydrogen Bond Donor Count:0
- Hydrogen Bond Acceptor Count:7
- Rotatable Bond Count:3
- Exact Mass:482.23045342
- Heavy Atom Count:35
- Complexity:1030
- Purity/Quality:
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99% *data from raw suppliers
Gedunin *data from reagent suppliers
Safty Information:
- Pictogram(s):
- Hazard Codes:
- MSDS Files:
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SDS file from LookChem
Useful:
- Canonical SMILES:CC(=O)OC1CC2C(C(=O)C=CC2(C3C1(C45C(O4)C(=O)OC(C5(CC3)C)C6=COC=C6)C)C)(C)C
- Isomeric SMILES:CC(=O)O[C@@H]1C[C@@H]2[C@](C=CC(=O)C2(C)C)([C@@H]3[C@@]1([C@]45[C@H](O4)C(=O)O[C@H]([C@@]5(CC3)C)C6=COC=C6)C)C
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Description
Gedunin is a natural inhibitor of the heat shock protein (Hsp90; Item Nos. 22734 | 22735) co-chaperone p23 that also inhibits Hsp90 expression in human teratocarcinomal NTERA-2 cells in vitro at 5 μg/ml. This tetranortriterpenoid, which is isolated from A. indica, binds to and blocks the chaperone activity of p23 to induce apoptosis in HeLa-PRB cells in vitro at a concentration of 20 μM. Gedunin inhibits breast cancer cell proliferation in vitro, with IC50 values of 8.84 and 3.22 μM in MCF-7 and SKBr-3 cells, respectively, and inhibits the growth of PANC-1 pancreatic cancer cells (IC50 = 25 μM) by targeting the sonic hedgehog pathway to induce apoptosis. It also exerts anti-inflammatory effects in vivo. In a mouse model of articular inflammation induced by zymosan , gedunin (0.05-0.5 mg/kg, i.p.) reduces edema formation and the production of inflammatory cytokines. Gedunin (0.5 mg/kg) also inhibits the pleural accumulation of eosinophils and activated T lymphocytes in an ovalbumin-sensitized mouse model of allergic inflammation when administered prior to ovalbumin rechallenge. It also targets the lipopolysaccharide binding site and thus blocks Toll-like receptor 4 (TLR4) signaling in macrophages in vitro at a concentration of 10 μM.
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Uses
Gedunin is a naturally occurring Hsp90 inhibitor. In vitro, Gedunin induces Hsp90-dependent client protein degradation and displays antiproliferative activity (IC50 values are 3.22, 8.84 and 16.8 μM in SKBr3, MCF-7 and CaCo-2 cancer cell lines respectively). Gedunin exhibits antimalarial activity against P. falciparum (IC50 values are 0.14 and 3.1 μM in parasite development and [3H]-hypoxanthine uptake assays respectively).
