CHEBI:156298 - aurafuron A

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ChEBI Name aurafuron A
ChEBI ID CHEBI:156298
Definition A polyketide that is 2,3-dihydrofuran substituted by hydroxy, methyl, oxo, methyl and (2S,3Z,5E,7R,8R,9E)-2,8-dihydroxy-7,9,12-trimethyltrideca-3,5,9-trien-1-yl groups at positions 2, 2, 3, 4, and 5, respectively. It is a cytotoxic natural product found in several myxobacteria species and inhibits the growth of some filamentous fungi.
Stars This entity has been manually annotated by the ChEBI Team.
Submitter Martin Larralde
Supplier Information
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Formula C22H34O5
Net Charge 0
Average Mass 378.509
Monoisotopic Mass 378.24062
InChI InChI=1S/C22H34O5/c1-14(2)11-12-16(4)20(24)15(3)9-7-8-10-18(23)13-19-17(5)21(25)22(6,26)27-19/h7-10,12,14-15,18,20,23-24,26H,11,13H2,1-6H3/b9-7+,10-8-,16-12+/t15-,18-,20-,22?/m1/s1
InChIKey AQQYZHDRTDSOER-LYKBUVKOSA-N
SMILES CC(C)C\C=C(/C)[C@H](O)[C@H](C)\C=C\C=C/[C@@H](O)CC1=C(C)C(=O)C(C)(O)O1
Metabolite of Species Details
Stigmatella aurantiaca DW4/3-1 (NCBI:txid378806) See: PubMed
Archangium gephyra (NCBI:txid48) Found in cell suspension culture (BTO:0000221). of strain Ar 10844 See: PubMed
Roles Classification
Biological Role(s): bacterial metabolite
Any prokaryotic metabolite produced during a metabolic reaction in bacteria.
antifungal agent
An antimicrobial agent that destroys fungi by suppressing their ability to grow or reproduce.
toxin
Poisonous substance produced by a biological organism such as a microbe, animal or plant.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing aurafuron A (CHEBI:156298) has role antifungal agent (CHEBI:35718)
aurafuron A (CHEBI:156298) has role bacterial metabolite (CHEBI:76969)
aurafuron A (CHEBI:156298) has role toxin (CHEBI:27026)
aurafuron A (CHEBI:156298) is a lactol (CHEBI:38131)
aurafuron A (CHEBI:156298) is a oxolanes (CHEBI:26912)
aurafuron A (CHEBI:156298) is a polyketide (CHEBI:26188)
aurafuron A (CHEBI:156298) is a secondary alcohol (CHEBI:35681)
aurafuron A (CHEBI:156298) is a secondary allylic alcohol (CHEBI:134396)
aurafuron A (CHEBI:156298) is a tertiary α-hydroxy ketone (CHEBI:139592)
aurafuron A (CHEBI:156298) is a triol (CHEBI:27136)
IUPAC Name
5-[(2S,3Z,5E,7R,8R,9E)-2,8-dihydroxy-7,9,12-trimethyltrideca-3,5,9-trien-1-yl]-2-hydroxy-2,4-dimethylfuran-3(2H)-one
Synonym Source
(−)-aurafuron A SUBMITTER
Manual Xref Database
9948038 ChemSpider
View more database links
Citations Waiting for Citations Types Sources
15981410 PubMed citation SUBMITTER
17919655 PubMed citation SUBMITTER
22632656 PubMed citation Europe PMC
Last Modified
14 April 2021