(1S,6S,12R,14S)-9,14-Dimethyl-5-methylidene-3,13-dioxatetracyclo[8.4.0.02,6.012,14]tetradec-9-en-4-one
Basic information
- CAS
36149-87-8- Standard SMILES
C=C1C(=O)OC2[C@H]1CCC(C)=C1C[C@H]3O[C@@]3(C)[C@@H]12- InChIKey
QXJYIGSXUBOSID-RFQJILJESA-N- Molecular formula
- C15H18O3
- Average molar mass
- 246.3 g/mol
- Monoisotopic mass
- 246.12559443
Overview
(1S,6S,12R,14S)-9,14-Dimethyl-5-methylidene-3,13-dioxatetracyclo[8.4.0.02,6.012,14]tetradec-9-en-4-one has been reported in Hippolytia dolichophylla with data available.
Names & identifiers
- Preferred name
- (1S,6S,12R,14S)-9,14-Dimethyl-5-methylidene-3,13-dioxatetracyclo[8.4.0.02,6.012,14]tetradec-9-en-4-one
- IUPAC
- (1S,6S,12R,14S)-9,14-dimethyl-5-methylidene-3,13-dioxatetracyclo[8.4.0.02,6.012,14]tetradec-9-en-4-one
- English name
- Oxireno[2,3]azuleno[4,5-b]furan-2(3H)-one, 3a,4,5,7,7a,8a,8b,8c-octahydro-6,8a-dimethyl-3-methylene-, (3aS,7aR,8aS,8bS,8cS)-
- Molecular formula
- C15H18O3
- Molecular weight
- 246.3
Names & synonyms
(1S,6S,12R,14S)-9,14-Dimethyl-5-methylidene-3,13-dioxatetracyclo[8.4.0.02,6.012,14]tetradec-9-en-4-oneOxireno(2,3)azuleno(4,5-b)furan-2(3H)-one, 3a,4,5,7,7a,8a,8b,8c-octahydro-6,8a-dimethyl-3-methylene-, (3aS,7aR,8aS,8bS,8cS)-Oxireno(2,3)azuleno(4,5-b)furan-2(3H)-one, 3a,4,5,7,7a,8a,8b,8c-octahydro-6,8a-dimethyl-3-methylene-, (3aS-(3aalpha,7abeta,8abeta,8balpha,8cbeta))-DTXSID20957562(3aS,7aR,8aS,8bS)-6,8a-Dimethyl-3-methylidene-3a,4,5,7,7a,8a,8b,8c-octahydrooxireno[2,3]azuleno[4,5-b]furan-2(3H)-one6,8a-Dimethyl-3-methylidene-3a,4,5,7,7a,8a,8b,8c-octahydrooxireno[2,3]azuleno[4,5-b]furan-2(3H)-oneLudartinOxireno[2,3]azuleno[4,5-b]furan-2(3H)-one, 3a,4,5,7,7a,8a,8b,8c-octahydro-6,8a-dimethyl-3-methylene-, (3aS,7aR,8aS,8bS,8cS)-
Database identifiers
- CAS
36149-87-8- PubChem CID
- 182276
- DTXSID
DTXSID20957562
Properties
Computed structural properties
- XLogP
- 1.4
- Topological polar surface area
- 38.8 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 0
- Heavy atoms
- 18
- Formal charge
- 0
- Complexity
- 504
Physicochemical properties
- Boiling point
- 406.5 · 406.5±45.0 °C(Predicted)
- Density
- 1.22 · 1.22±0.1 g/cm3(Predicted)
Chemistry & industry
Applications
UsesLudartin a sesquiterpene lactone, which can be isolated from the plant Artemisia carruthii Wood. Ludartin reduces the expression of myeloperoxidase and malondialdehyde, enhances the expression of glutathione and superoxide dismutase in spinal cord tissue. Ludartin inhibits neuronal apoptosis. Ludartin inhibits the upregulation of tumor necrosis factor-α, interleukin-1β, and interleukin-6. Ludartin improves the motor function of rats with spinal cord injury[1].
Related reactions
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Compound notes
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