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CHEBI:133035 - yanuthone K

ChEBI IDCHEBI:133035
ChEBI Nameyanuthone K
Stars
DefinitionA class I yanuthone that is 5,6-epoxy-cyclohex-2-en-1-one which is substituted at positions 3, 4, and 6 by methyl, acetoxy, and trans,trans-farnesyl groups, respectively (the R,R,R stereoisomer). Isolated from the filamentous fungus Aspergillus niger, it shows antifungal activity towards the pathogenic yeast Candida albicans (IC50 = 17.5 ±3.9 μM).
Last Modified21 November 2016
SubmitterJubra
DownloadsMolfile
FormulaC24H34O4
Net Charge0
Average Mass386.532
Monoisotopic Mass386.24571
SMILESCC(=O)O[C@@H]1C(C)=CC(=O)[C@]2(C/C=C(\C)CC/C=C(\C)CCC=C(C)C)O[C@H]12
InChIInChI=1S/C24H34O4/c1-16(2)9-7-10-17(3)11-8-12-18(4)13-14-24-21(26)15-19(5)22(23(24)28-24)27-20(6)25/h9,11,13,15,22-23H,7-8,10,12,14H2,1-6H3/b17-11+,18-13+/t22-,23-,24+/m1/s1
InChIKeyDOKAHTTXUSOTHL-YVCJEVKHSA-N
Species of MetaboliteComponentSourceComments
Aspergillus niger ATCC 1015 (ncbitaxon:380704) - PubMed (25293978) Strain: KB1001
Roles Classification
Biological Roles:
antifungal agent  An antimicrobial agent that destroys fungi by suppressing their ability to grow or reproduce.
Aspergillus metabolite  Any fungal metabolite produced during a metabolic reaction in the mould, Aspergillus .
metabolite  Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
ChEBI Ontology
Outgoing Relation(s)
yanuthone K (CHEBI:133035) has functional parent (2-trans,6-trans)-farnesol (CHEBI:16619)
yanuthone K (CHEBI:133035) has functional parent 7-deacetoxyyanuthone A (CHEBI:133843)
yanuthone K (CHEBI:133035) has role Aspergillus metabolite (CHEBI:76956)
yanuthone K (CHEBI:133035) has role antifungal agent (CHEBI:35718)
yanuthone K (CHEBI:133035) is a acetate ester (CHEBI:47622)
yanuthone K (CHEBI:133035) is a class I yanuthone (CHEBI:133075)
Incoming Relation(s)
yanuthone L (CHEBI:133034) has functional parent yanuthone K (CHEBI:133035)
yanuthone M (CHEBI:133036) has functional parent yanuthone K (CHEBI:133035)
IUPAC Name 
(1R,2R,6R)-3-methyl-5-oxo-6-[(2E,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-yl]-7-oxabicyclo[4.1.0]hept-3-en-2-yl acetate
Synonym  Source
yanuthone-KChEBI
Registry NumbersSources
Reaxys:27991879Reaxys
Citations