asperlactone (CHEBI:156386)

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ChEBI Name	asperlactone

ChEBI ID	CHEBI:156386

Definition	A member of the class of butenolides that is furan-2(5H)-one substituted by (2S,3S)-3-methyloxiran-2-yl and (1S)-1-hydroxyethyl group at positions 3 and 5R, respectively. It is a secondary metabolite isolated from Aspergillus ochraceus that exhibits antifungal and antibacterial properties.

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

Submitter	Martin Larralde

Supplier Information

Download	Molfile XML SDF

Formula

C9H12O4

Net Charge

Average Mass

184.191

Monoisotopic Mass

184.07356

InChI

InChI=1S/C9H12O4/c1-4(10)7-3-6(9(11)13-7)8-5(2)12-8/h3-5,7-8,10H,1-2H3/t4-,5-,7+,8+/m0/s1

InChIKey

VMLNPJDEXLLCQG-DGCAKLBHSA-N

SMILES

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

Metabolite of Species	Details
Aspergillus creber (NCBI:txid1220201)	See: PubMed
Exophiala sp. (NCBI:txid1718875)	See: PubMed
Aspergillus ochraceopetaliformis (NCBI:txid176175)	See: PubMed
Aspergillus westerdijkiae (NCBI:txid357447)	See: PubMed
Aspergillus ochraceus (NCBI:txid40380)	See: DOI

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

Application(s):	insect growth regulator A growth regulator that inhibits the life cycle of an insect.

ChEBI Ontology
Outgoing	asperlactone (CHEBI:156386) has role Aspergillus metabolite (CHEBI:76956) asperlactone (CHEBI:156386) has role antibacterial agent (CHEBI:33282) asperlactone (CHEBI:156386) has role insect growth regulator (CHEBI:24851) asperlactone (CHEBI:156386) has role mycotoxin (CHEBI:25442) asperlactone (CHEBI:156386) is a antibiotic antifungal agent (CHEBI:86478) asperlactone (CHEBI:156386) is a butenolide (CHEBI:50523) asperlactone (CHEBI:156386) is a epoxide (CHEBI:32955) asperlactone (CHEBI:156386) is a polyketide (CHEBI:26188) asperlactone (CHEBI:156386) is a secondary alcohol (CHEBI:35681)

IUPAC Name

(5R)-5-[(1S)-1-hydroxyethyl]-3-[(2S,3S)-3-methyloxiran-2-yl]furan-2(5H)-one

Synonym	Source
5R-[(1S)-1-hydroxyethyl]-3-[(2S,3S)-3-methyl-2-oxiranyl]-2(5H)-furanone	ChEBI

Registry Number	Type	Source
76375-62-7	CAS Registry Number	ChemIDplus

Last Modified

17 May 2021