Pseurotin A
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Pseurotin A
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CAS No:
58523-30-1
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Formula:
C22H25NO8
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Chemical Name:
Pseurotin A
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Synonyms:
1-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)-;1-Oxa-7-azaspiro[4.4]non-2-ene-4,6-dione,8-benzoyl-2-(1,2-dihydroxy-3-hexenyl)-9-hydroxy-8-methoxy-3-methyl-,[5S-[2(1R*,2R*,3Z),5α,8β,9β]]-;1-Oxa-7-azaspiro[4.4]non-2-ene-4,6-dione,8-benzoyl-2-[(1S,2S,3Z)-1,2-dihydroxy-3-hexenyl]-9-hydroxy-8-methoxy-3-methyl-,(5S,8S,9R)-;(5S,8S,9R)-8-Benzoyl-2-[(1S,2S,3Z)-1,2-dihydroxy-3-hexen-1-yl]-9-hydroxy-8-methoxy-3-methyl-1-oxa-7-azaspiro[4.4]non-2-ene-4,6-dione;Pseurotin A;Pseurotin;NSC 348694
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CAS No:
Description
ChEBI: 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.
Characteristics
142.39000
0.33160
1.41±0.1 g/cm3(Predicted)
126.0-126.9 °C @ Solvent: Dichloromethane, Hexane
751.5ºC at 760 mmHg
408.3ºC
1.626
Pseurotin A Use and Manufacturing
Pseurotin 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.
Computed Properties
Molecular Weight:431.4
XLogP3:0.5
Hydrogen Bond Donor Count:4
Hydrogen Bond Acceptor Count:8
Rotatable Bond Count:7
Exact Mass:431.15801676
Monoisotopic Mass:431.15801676
Topological Polar Surface Area:142
Heavy Atom Count:31
Complexity:814
Undefined Atom Stereocenter Count:5
Undefined Bond Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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