aspyrone (CHEBI:156387)

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ChEBI Name	aspyrone

ChEBI ID	CHEBI:156387

Definition	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.

Stars	This entity has been manually annotated by the ChEBI Team.

Submitter	Martin Larralde

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Formula

C9H12O4

Net Charge

Average Mass

184.191

Monoisotopic Mass

184.07356

InChI

InChI=1S/C9H12O4/c1-4-7(10)3-6(9(11)13-4)8-5(2)12-8/h3-5,7-8,10H,1-2H3/t4-,5+,7+,8-/m1/s1

InChIKey

RCAULRNMJFUWRP-HETMPLHPSA-N

SMILES

[H][C@@]1(C)O[C@@]1([H])C1=C[C@H](O)[C@@H](C)OC1=O

Metabolite of Species	Details
Aspergillus melleus (NCBI:txid138277)	See: DOI
Exophiala sp. (NCBI:txid1718875)	See: PubMed
Aspergillus westerdijkiae (NCBI:txid357447)	See: PubMed
Aspergillus ochraceus (NCBI:txid40380)	See: DOI
Aspergillus ochraceus (NCBI:txid40380)	of strain LCJ11-102 See: PubMed

Roles Classification
Biological Role(s):	mycotoxin Poisonous substance produced by fungi. antibacterial agent A substance (or active part thereof) that kills or slows the growth of bacteria. Aspergillus metabolite Any fungal metabolite produced during a metabolic reaction in the mould, Aspergillus . antifungal agent An antimicrobial agent that destroys fungi by suppressing their ability to grow or reproduce. (via antibiotic antifungal agent )

Application(s):	nematicide A substance used to destroy pests of the phylum Nematoda (roundworms).

ChEBI Ontology
Outgoing	aspyrone (CHEBI:156387) has role Aspergillus metabolite (CHEBI:76956) aspyrone (CHEBI:156387) has role antibacterial agent (CHEBI:33282) aspyrone (CHEBI:156387) has role mycotoxin (CHEBI:25442) aspyrone (CHEBI:156387) has role nematicide (CHEBI:25491) aspyrone (CHEBI:156387) is a 2-pyranones (CHEBI:75885) aspyrone (CHEBI:156387) is a antibiotic antifungal agent (CHEBI:86478) aspyrone (CHEBI:156387) is a epoxide (CHEBI:32955) aspyrone (CHEBI:156387) is a polyketide (CHEBI:26188) aspyrone (CHEBI:156387) is a secondary alcohol (CHEBI:35681)

IUPAC Name

(5S,6R)-5-hydroxy-6-methyl-3-[(2S,3S)-3-methyloxiran-2-yl]-5,6-dihydro-2H-pyran-2-one

Registry Number	Type	Source
17398-00-4	CAS Registry Number	ChemIDplus

Last Modified

27 August 2020