8-benzoyl-2-[(E)-1,2-dihydroxyhex-3-enyl]-9-hydroxy-8-methoxy-3-methyl-1-oxa-7-azaspiro[4.4]non-2-ene-4,6-dione
Basic information
- CAS
58523-30-1- Standard SMILES
CC/C=C/C(O)C(O)C1=C(C)C(=O)C2(O1)C(=O)NC(OC)(C(=O)c1ccccc1)C2O- InChIKey
SLYDIPAXCVVRNY-VZUCSPMQSA-N- Molecular formula
- C22H25NO8
- Average molar mass
- 431.4 g/mol
- Monoisotopic mass
- 431.15801676
Overview
pseurotin A has been reported in Aspergillus insulicola, Cordyceps tenuipes, and other organisms with data available.
Names & identifiers
- Preferred name
- 8-benzoyl-2-[(E)-1,2-dihydroxyhex-3-enyl]-9-hydroxy-8-methoxy-3-methyl-1-oxa-7-azaspiro[4.4]non-2-ene-4,6-dione
- IUPAC
- 8-benzoyl-2-[(E)-1,2-dihydroxyhex-3-enyl]-9-hydroxy-8-methoxy-3-methyl-1-oxa-7-azaspiro[4.4]non-2-ene-4,6-dione
- English name
- pseurotin
- Molecular formula
- C22H25NO8
- Molecular weight
- 431.44
Names & synonyms
Pseurotin A58523-30-1Compound NP-006189(8S,9R)-8-Benzoyl-2-[(E,1S,2S)-1,2-dihydroxyhex-3-enyl]-9-hydroxy-8-methoxy-3-methyl-1-oxa-7-azaspiro[4.4]non-2-ene-4,6-dioneHB4038NSC348694AKOS040739641NCGC00380982-01(5S,8S,9R)-8-Benzoyl-2-((1S,2S,Z)-1,2-dihydroxyhex-3-en-1-yl)-9-hydroxy-8-methoxy-3-methyl-1-oxa-7-azaspironon-2-ene-4,6-dioneNCGC00380982-01_C22H25NO8_8-Benzoyl-2-[(3E)-1,2-dihydroxy-3-hexen-1-yl]-9-hydroxy-8-methoxy-3-methyl-1-oxa-7-azaspiro[4.4]non-2-ene-4,6-dionePB-1pseurotin
Show more names
NSC 348694Pseurotin A, chitin synthase inhibitor(5S,8S,9R)-8-benzoyl-2-[(Z,1S,2S)-1,2-dihydroxyhex-3-enyl]-9-hydroxy-8-methoxy-3-methyl-1-oxa-7-azaspiro[4.4]non-2-ene-4,6-dione(5S,8S,9R)-8-Benzoyl-2-[(1S,2S,3Z)-1,2-dihydroxy-3-hexenyl]-9-hydroxy-8-methoxy-3-methyl-1-oxa-7-azaspiro[4.4]non-2-ene-4,6-dione1-Oxa-7-azaspiro[4.4]non-2-ene-4,6-dione, 8-benzoyl-2-[(1S,2S,3Z)-1,2-dihydroxy-3-hexen-1-yl]-9-hydroxy-8-methoxy-3-methyl-, (5S,8S,9R)-
Properties
Computed structural properties
- XLogP
- 0.5
- Topological polar surface area
- 142 Ų
- Hydrogen bond donors
- 4
- Hydrogen bond acceptors
- 8
- Rotatable bonds
- 7
- Heavy atoms
- 31
- Formal charge
- 0
- Complexity
- 814
Physicochemical properties
- Melting point
- 126 · 126.0-126.9℃
- Boiling point
- 751.5 · 751.5±60.0 °C(Predicted)
- Density
- 1.41 · 1.41±0.1 g/cm3(Predicted)
- storage temp.
- -20 °C · -20°C
- solubility
- Soluble in DMSO (10 mg/ml)
- pka
- 14.76 · 14.76±0.20(Predicted)
- form
- White to off-white powder.
- color
- White
- Stability
- 2 years · Stable for 2 years from date of purchase as supplied. Solutions in DMSO may be stored at -20°C for up to 3 months.
- FDA UNII
- 73 C5W8FNE · H73C5W8FNE
Chemistry & industry
Applications
DescriptionPseurotin A (58523-30-1) is a fungal metabolite with novel structure. Displays potent neuritogenic activity in PC12 cells. Induces multipolar and branching neurites comparable to that produced by β-NGF.1 Displays immunosuppressive activity via inhibition of immunoglobulin E production in vitro.2 Displays antiproliferative effects on four glioma cell lines by regulating tumor metabolic enzymes.3 Inhibits osteoclastogenesis and prevents ovariectomized-induced bone loss by suppression of ROS.4
UsesPseurotin A is a fungal metabolite with an unusual hetero-spirocyclic ring system. It has potent neuritogenic activity in PC12 phaechromocytoma cells, a useful model for adrenergic neuronal differentiation. Pseurotin A induces multipolar and branching neurites comparable to β-NGF, an endogenous neurotrophic factor. Pseurotin A also exhibits chitinase inhibition and acts synergistically with azole antifungal agents.
UsesPseurotin A shows antiparasitic and anticancer activity. It exhibits inhibition towards IgE (immunoglobin E) production.
Additional notes
DefinitionChEBI: A spirocyclic that is 1-oxa-7-azaspiro[4.4]non-2-ene-4,6-dione bearing 1,2-dihydroxyhex-3-en-1-yl, methyl, methoxy, benzoyl and hydroxy substituents at positions 2, 3, 8, 8 and 9 respectively.
Suppliers
Loading…
Open inquiries
Loading…
Related reactions
0 records
No reaction records under the current filter.
Compound notes
Loading…