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CHEBI:133036 - yanuthone M

ChEBI IDCHEBI:133036
ChEBI Nameyanuthone M
Stars
DefinitionA class I yanuthone that is yanuthone K in which the double bond at the terminal end of the farnesyl substituent has undergone hydration to afford the corresponding tertiary alcohol. Isolated from the filamentous fungus Aspergillus niger, it shows antifungal activity towards the pathogenic yeast Candida albicans (IC50 = 77.5 ±3.7 μM).
Last Modified19 August 2016
SubmitterJubra
DownloadsMolfile
FormulaC24H36O5
Net Charge0
Average Mass404.547
Monoisotopic Mass404.25627
SMILESCC(=O)OC1C(C)=CC(=O)[C@]2(C/C=C(\C)CC/C=C(\C)CCCC(C)(C)O)O[C@H]12
InChIInChI=1S/C24H36O5/c1-16(11-8-13-23(5,6)27)9-7-10-17(2)12-14-24-20(26)15-18(3)21(22(24)29-24)28-19(4)25/h9,12,15,21-22,27H,7-8,10-11,13-14H2,1-6H3/b16-9+,17-12+/t21?,22-,24+/m1/s1
InChIKeyUDCFQVYVEMPFKM-CTPBMWBYSA-N
Species of MetaboliteComponentSourceComments
Aspergillus niger ATCC 1015 (ncbitaxon:380704) - PubMed (25293978) Strain: KB1001
Roles Classification
Chemical Role:
Bronsted base  A molecular entity capable of accepting a hydron from a donor (Brønsted acid).
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 M (CHEBI:133036) has functional parent yanuthone K (CHEBI:133035)
yanuthone M (CHEBI:133036) has role Aspergillus metabolite (CHEBI:76956)
yanuthone M (CHEBI:133036) has role antifungal agent (CHEBI:35718)
yanuthone M (CHEBI:133036) is a acetate ester (CHEBI:47622)
yanuthone M (CHEBI:133036) is a class I yanuthone (CHEBI:133075)
yanuthone M (CHEBI:133036) is a tertiary amine (CHEBI:32876)
IUPAC Name 
(1R,6R)-6-[(2E,6E)-11-hydroxy-3,7,11-trimethyldodeca-2,6-dien-1-yl]-3-methyl-5-oxo-7-oxabicyclo[4.1.0]hept-3-en-2-yl acetate
Synonym  Source
yanuthone-MChEBI
Registry NumbersSources
Reaxys:27991881Reaxys
Citations