Basic information
- CAS
41059-80-7- Standard SMILES
C=C1C(=O)OC2C1C(OC(C)=O)C/C(C)=C/CCC1(C)OC21- InChIKey
ODYJJNFWFYUXSS-RMKNXTFCSA-N- Molecular formula
- C17H22O5
- Average molar mass
- 306.4 g/mol
- Monoisotopic mass
- 306.1467238
Names & identifiers
- Preferred name
- Acetoxyparthenolide
- IUPAC
- [(7E)-4,8-dimethyl-12-methylidene-13-oxo-3,14-dioxatricyclo[9.3.0.02,4]tetradec-7-en-10-yl] acetate
- English name
- (1aR,4E,7R,7aR,10aS,10bR)-7-Acetoxy-2,3,6,7,7a,8,10a,10b-octahydro-1a,5-dimethyl-8-methyleneoxireno[9,10]cyclodeca[1,2-b]furan-9(1aH)-one
- Molecular formula
- C17H22O5
- Molecular weight
- 306.35
Names & synonyms
ACETOXYPARTHENOLIDE41059-80-7[(7E)-4,8-dimethyl-12-methylidene-13-oxo-3,14-dioxatricyclo[9.3.0.02,4]tetradec-7-en-10-yl] acetate8.beta.-Acetoxy-parthenolideNSC251676NSC-251676AKOS032948483Lipiferolide8.β.-Acetoxy-parthenolide(1aR,4E,7R,7aR,10aS,10bR)-7-Acetoxy-2,3,6,7,7a,8,10a,10b-octahydro-1a,5-dimethyl-8-methyleneoxireno[9,10]cyclodeca[1,2-b]furan-9(1aH)-oneOxireno[9,10]cyclodeca[1,2-b]furan-9(1aH)-one, 7-(acetyloxy)-2,3,6,7,7a,8,10a,10b-octahydro-1a,5-dimethyl-8-methylene-, (1aR,4E,7R,7aR,10aS,10bS)-Oxireno[9,10]cyclodeca[1,2-b]furan-9(1aH)-one,7-(acetyloxy)-2,3,6,7,7a,8,10a,10b-octahydro- 1a,5-diMethyl-8-Methylene-,[1aR-(1aR*,4E,- 7R*,7aR*,10aS*,10bS*)]-
Database identifiers
- CAS
41059-80-7- PubChem CID
- 54598331
Properties
Computed structural properties
- XLogP
- 1.9
- Topological polar surface area
- 65.1 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 5
- Rotatable bonds
- 2
- Heavy atoms
- 22
- Formal charge
- 0
- Complexity
- 563
Physicochemical properties
- Boiling point
- 444.8 · 444.8±45.0 °C(Predicted)
- Density
- 1.19 · 1.19±0.1 g/cm3(Predicted)
- solubility
- Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
- form
- Powder
Chemistry & industry
Applications
DescriptionLipiferolide is an inhibitor of farnesyl protein transferase(FPTase), it inhibits the FPTase activity in a dose-dependent manner, and shows cell growth inhibitory activity against several tumor cells. Liriodenine has antiplasmodial activity. 3. Lipiferolide and epitulipinolide diepoxide possess cytotoxic activity against KB cells.
UsesLipiferolide is an antiplasmodial agent (IC50: 1.8 μg/mL) that can be isolated from Liriodendron tulipifera. Lipiferolide also inhibits FPTase, and has antitumor activity[1][2].
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Related reactions
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Compound notes
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