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CHEBI:156387 - aspyrone

ChEBI IDCHEBI:156387
ChEBI Nameaspyrone
Stars
DefinitionA 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.
Last Modified27 August 2020
SubmitterMartin Larralde
DownloadsMolfile
FormulaC9H12O4
Net Charge0
Average Mass184.191
Monoisotopic Mass184.07356
SMILES[H][C@@]1(C2=C[C@H](O)[C@@H](C)OC2=O)O[C@@]1([H])C
InChIInChI=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
InChIKeyRCAULRNMJFUWRP-HETMPLHPSA-N
Species of MetaboliteComponentSourceComments
Aspergillus melleus (ncbitaxon:138277) - DOI (10.1271/bbb.60.1375)
Aspergillus ochraceus (ncbitaxon:40380)
- DOI (10.1002/(SICI)1096-9063(199805)53:1<9::AID-PS745>3.0.CO;2-P)
- PubMed (31284571) Strain: LCJ11-102
Exophiala sp. (ncbitaxon:1718875) - PubMed (18661951)
Aspergillus westerdijkiae (ncbitaxon:357447) - PubMed (19589392 )
Roles Classification
Biological Roles:
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 .
mycotoxin  Poisonous substance produced by fungi.
antifungal agent  An antimicrobial agent that destroys fungi by suppressing their ability to grow or reproduce.
Application:
nematicide  A substance used to destroy pests of the phylum Nematoda (roundworms).
ChEBI Ontology
Outgoing Relation(s)
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 NumbersSources
CAS:17398-00-4ChemIDplus
Citations