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CHEBI:133035 - yanuthone K

Default Structure
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:
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.
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