Aspyrone
Basic information
- CAS
17398-00-4- Standard SMILES
C[C@@H]1O[C@H]1C1=C[C@H](O)[C@@H](C)OC1=O- InChIKey
RCAULRNMJFUWRP-HETMPLHPSA-N- Molecular formula
- C9H12O4
- Average molar mass
- 184.19 g/mol
- Monoisotopic mass
- 184.07355886
Overview
Aspyrone is a member of the class of 2-pyranones that is 5,6-dihydro-2H-pyran-2-one in which the hydrogens at positions 3, 5S and 6R are replaced by (2S,3S)-3-methyloxiran-2-yl, hydroxy and methyl groups, respectively. It is a fungal metabolite isolated from Aspergillus melleus and exhibits nematicidal, antibacterial and antifungal properties. It has a role as a mycotoxin, a nematicide, an antibacterial agent and an Aspergillus metabolite. It is a polyketide, an epoxide, a secondary alcohol, a member of 2-pyranones and an antibiotic antifungal agent.
Names & identifiers
- Preferred name
- Aspyrone
- IUPAC
- (2R,3S)-3-hydroxy-2-methyl-5-[(2S,3S)-3-methyloxiran-2-yl]-2,3-dihydropyran-6-one
- English name
- aspyrone
- Molecular formula
- C9H12O4
- Molecular weight
- 184.19
Names & synonyms
Aspyrone17398-00-4CHEBI:156387DTXSID50169737RefChem:916404DTXCID7092228(2R,3S)-3-hydroxy-2-methyl-5-((2S,3S)-3-methyloxiran-2-yl)-2,3-dihydropyran-6-one(2R,3S)-3-hydroxy-2-methyl-5-[(2S,3S)-3-methyloxiran-2-yl]-2,3-dihydropyran-6-one(5s,6r)-5-hydroxy-6-methyl-3-[(2s,3s)-3-methyloxiran-2-yl]-5,6-dihydro-2h-pyran-2-one2H-Pyran-2-one, 5,6-dihydro-5-hydroxy-6-methyl-3-[(2S,3S)-3-methyl-2-oxiranyl]-, (5S,6R)-(5S,6R)-5-Hydroxy-6-methyl-3-((2S,3S)-3-methyloxiran-2-yl)-5,6-dihydro-2H-pyran-2-oneaspiron
Show more names
(5S,6R)-5,6-Dihydro-5-hydroxy-6-methyl-3-[(2S,3S)-3-methyloxiranyl]-2H-pyran-2-one(5S)-5,6-Dihydro-5α-hydroxy-6β-methyl-3-[(2S,3S)-3-methyloxiran-2-yl]-2H-pyran-2-one
3-(1,2-epoxypropyl)-5,6-dihydro-5-hydroxy-6-methylpyran-2-oneorb1692684SCHEMBL1008312RCAULRNMJFUWRP-HETMPLHPSA-MFCD14635403AKOS040755982HY-121003CS-0078921
Properties
Computed structural properties
- XLogP
- -0.1
- Topological polar surface area
- 59.1 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 4
- Rotatable bonds
- 1
- Heavy atoms
- 13
- Formal charge
- 0
- Complexity
- 271
Physicochemical properties
- Boiling point
- 383.5 · 383.5±42.0 °C(Predicted)
- Density
- 1.313 · 1.313±0.06 g/cm3(Predicted)
- storage temp.
- -20 °C · Store at -20°C
- solubility
- Acetone: soluble,DMSO: soluble,Methanol: soluble
- form
- A solid
- pka
- 11.93 · 11.93±0.60(Predicted)
Chemistry & industry
Applications
UsesAspyrone is anAspergillusmold natural product antibiotic with nematicidial properties.
Additional notes
DefinitionChEBI: Aspyrone is a member of the class of 2-pyranones that is 5,6-dihydro-2H-pyran-2-one in which the hydrogens at positions 3, 5S and 6R are replaced by (2S,3S)-3-methyloxiran-2-yl, hydroxy and methyl groups, respectively. It is a fungal metabolite isolated from Aspergillus melleus and exhibits nematicidal, antibacterial and antifungal properties. It has a role as a mycotoxin, an antibacterial agent, an Aspergillus metabolite and a nematicide. It is a secondary alcohol, an epoxide, a polyketide, an antibiotic antifungal agent and a member of 2-pyranones.
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