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CHEBI:156386 - asperlactone

ChEBI IDCHEBI:156386
ChEBI Nameasperlactone
Stars
DefinitionA 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.
Last Modified17 May 2021
SubmitterMartin Larralde
DownloadsMolfile
FormulaC9H12O4
Net Charge0
Average Mass184.191
Monoisotopic Mass184.07356
SMILES[H][C@]1([C@H](C)O)C=C([C@@H]2O[C@H]2C)C(=O)O1
InChIInChI=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
InChIKeyVMLNPJDEXLLCQG-DGCAKLBHSA-N
Species of MetaboliteComponentSourceComments
Aspergillus creber (ncbitaxon:1220201) - PubMed (31880876 )
Aspergillus westerdijkiae (ncbitaxon:357447) - PubMed (19589392)
Exophiala sp. (ncbitaxon:1718875) - PubMed (18661951)
Aspergillus ochraceus (ncbitaxon:40380) - DOI (10.1002/(SICI)1096-9063(199805)53:1<9::AID-PS745>3.0.CO;2-P)
Aspergillus ochraceopetaliformis (ncbitaxon:176175) - PubMed (32875235)
Roles Classification
Biological Roles:
insect growth regulator  A growth regulator that inhibits the life cycle of an insect.
antibacterial agent  A substance (or active part thereof) that kills or slows the growth of bacteria.
mycotoxin  Poisonous substance produced by fungi.
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.
Application:
insect growth regulator  A growth regulator that inhibits the life cycle of an insect.
ChEBI Ontology
Outgoing Relation(s)
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)-furanoneChEBI
Registry NumbersSources
CAS:76375-62-7ChemIDplus
Citations