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CHEBI:156298 - aurafuron A

ChEBI IDCHEBI:156298
ChEBI Nameaurafuron A
Stars
DefinitionA 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.
Last Modified14 April 2021
SubmitterMartin Larralde
DownloadsMolfile
FormulaC22H34O5
Net Charge0
Average Mass378.509
Monoisotopic Mass378.24062
SMILESCC1=C(C[C@H](O)/C=C\C=C\[C@@H](C)[C@@H](O)/C(C)=C/CC(C)C)OC(C)(O)C1=O
InChIInChI=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
InChIKeyAQQYZHDRTDSOER-LYKBUVKOSA-N
Species of MetaboliteComponentSourceComments
Stigmatella aurantiaca DW4/3-1 (ncbitaxon:378806) - PubMed (17919655)
Archangium gephyra (ncbitaxon:48) cell suspension culture (BTO:0000221) PubMed (15981410) Strain: Ar 10844
Roles Classification
Biological Roles:
bacterial metabolite  Any prokaryotic metabolite produced during a metabolic reaction in bacteria.
toxin  Poisonous substance produced by a biological organism such as a microbe, animal or plant.
antifungal agent  An antimicrobial agent that destroys fungi by suppressing their ability to grow or reproduce.
ChEBI Ontology
Outgoing Relation(s)
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 ASUBMITTER
Manual XrefsDatabases
9948038ChemSpider
Citations