Micheliolide
Basic information
- CAS
68370-47-8- Standard SMILES
C=C1C(=O)O[C@H]2[C@H]1CCC(C)=C1CC[C@@](C)(O)[C@@H]12- InChIKey
RDJAFOWISVMOJY-PWNZVWSESA-N- Molecular formula
- C15H20O3
- Average molar mass
- 248.32 g/mol
- Monoisotopic mass
- 248.1412445
Overview
Micheliolide is a sesquiterpene lactone.
Names & identifiers
- Preferred name
- Micheliolide
- IUPAC
- (3aS,9R,9aS,9bS)-9-hydroxy-6,9-dimethyl-3-methylidene-4,5,7,8,9a,9b-hexahydro-3aH-azuleno[4,5-b]furan-2-one
- English name
- Micheliolide
- Molecular formula
- C15H20O3
- Molecular weight
- 248.32
Names & synonyms
MICHELIOLIDE68370-47-8(3aS,9R,9aS,9bS)-9-hydroxy-6,9-dimethyl-3-methylidene-4,5,7,8,9a,9b-hexahydro-3aH-azuleno[4,5-b]furan-2-oneDTXSID20331787(3aS,9R,9aS,9bS)-9-hydroxy-6,9-dimethyl-3-methylene-4,5,7,8,9a,9b-hexahydro-3aH-azuleno[4,5-b]furan-2-one(3aS,9R,9aS,9bS)-9-hydroxy-6,9-dimethyl-3-methylene-4,5,7,8,9a,9b-hexahydro-3aH-azuleno(4,5-b)furan-2-one(3aS,9R,9aS,9bS)-9-hydroxy-6,9-dimethyl-3-methylidene-4,5,7,8,9a,9b-hexahydro-3aH-azuleno(4,5-b)furan-2-oneRefChem:158509DTXCID20282881MecheliolideCHEBI:6922MFCD27953044
Show more names
CS-1321Micheliolide, BRMicheliolide 68370-47-8Micheliolide, 10 mM in DMSONuclear factor-κB,NF-κB,inhibit,Micheliolide,Nuclear factor-kappaB,Inhibitor(3aS)-3aβ,4,5,7,8,9,9aβ,9bα-Octahydro-9β-hydroxy-6,9-dimethyl-3-methyleneazuleno[4,5-b]furan-2(3H)-one(3aS,9R,9aS,9bS)-9-Hydroxy-6,9-dimethyl-3-methylidene-3a,4,5,7,8,9,9a,9b-octahydroazuleno[4,5-b]furan-2(3H)-one
C15H20O3(3aS,9R,9aS,9bS)-9-hydroxy-6,9-dimethyl-3-methylene-3a,4,5,7,8,9,9a,9b-octahydroazuleno[4,5-b]furan-2(3H)-one(3aS,9R,9aS,9bS)-9-hydroxy-6,9-dimethyl-3-methylidene-2H,3H,3aH,4H,5H,7H,8H,9H,9aH,9bH-azuleno[4,5-b]furan-2-one(3aS,9R,9aS,9bS,Z)-9-hydroxy-6,9-dimethyl-3-methylene-3,3a,4,5,7,8,9,9a-octahydroazuleno[4,5-b]furan-2(9bH)-oneC09507CHEMBL449579(3aS)-3abeta,4,5,7,8,9,9abeta,9balpha-Octahydro-9beta-hydroxy-6,9-dimethyl-3-methyleneazuleno[4,5-b]furan-2(3H)-oneorb1220688
Database identifiers
- CAS
68370-47-8- PubChem CID
- 442279
- DTXSID
DTXSID20331787- ChEMBL
CHEMBL449579- ChEBI
CHEBI:6922- Nikkaji
- J19.496D
Properties
Computed structural properties
- XLogP
- 1.3
- Topological polar surface area
- 46.5 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 0
- Heavy atoms
- 18
- Formal charge
- 0
- Complexity
- 462
Physicochemical properties
- Melting point
- 131 · 131-133 °C
- Boiling point
- 426.1 · 426.1±45.0 °C(Predicted)
- Density
- 1.17 · 1.17±0.1 g/cm3(Predicted)
- storage temp.
- 2 · 2-8°C
- solubility
- Chloroform (Slightly), Methanol (Slightly)
- form
- Solid
- pka
- 14.65 · 14.65±0.40(Predicted)
- color
- Off-White
- InChI
- InChI=1S/C15H20O3/c1-8-4-5-11-9(2)14(16)18-13(11)12-10(8)6-7-15(12,3)17/h11-13,17H,2,4-7H2,1,3H3/t11-,12-,13-,15+/m0/s1
- InChIKey
- RDJAFOWISVMOJY-PWNZVWSESA-N
- SMILES
- O1C(=O)C(=C)[C@]2([H])CCC(C)=C3[C@@]([H])([C@@]12[H])[C@@](O)(C)CC3
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 302 · H302-H312-H315-H319
- Precautionary statements
- 280 · P280-P305+P351+P338
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety data
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- Hazard statements
- H302-H312-H315-H319
- Precautionary statements
- P280-P305+P351+P338
Chemistry & industry
Applications
UsesMicheliolide, a sesquiterpene lactone is used in the inhibition of resistant acute leukemic cells. Selectively targets cancer stem and progenitor cells.
Additional notes
DefinitionChEBI: Micheliolide is a sesquiterpene lactone.
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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