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CHEBI:133034 - yanuthone L

Default Structure
ChEBI IDCHEBI:133034
ChEBI Nameyanuthone L
Stars
DefinitionA class I yanuthone that is yanuthone K in which a hydrogen of the pro-E methyl group at the terminus of the farnesyl substituent has been replaced by a hydroxy group. Isolated from the filamentous fungus Aspergillus niger, it shows antifungal activity towards the pathogenic yeast Candida albicans (IC50 = 17.0 ±1.9 μM).
Last Modified19 August 2016
SubmitterJubra
DownloadsMolfile
FormulaC24H34O5
Net Charge0
Average Mass402.531
Monoisotopic Mass402.24062
SMILESCC(=O)O[C@@H]1C(C)=CC(=O)[C@]2(C/C=C(\C)CC/C=C(\C)CC/C=C(\C)CO)O[C@H]12
InChIInChI=1S/C24H34O5/c1-16(9-7-11-18(3)15-25)8-6-10-17(2)12-13-24-21(27)14-19(4)22(23(24)29-24)28-20(5)26/h8,11-12,14,22-23,25H,6-7,9-10,13,15H2,1-5H3/b16-8+,17-12+,18-11+/t22-,23-,24+/m1/s1
InChIKeyULUIYCOUZXIMPX-XXMQOAAMSA-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 L (CHEBI:133034) has functional parent yanuthone K (CHEBI:133035)
yanuthone L (CHEBI:133034) has role Aspergillus metabolite (CHEBI:76956)
yanuthone L (CHEBI:133034) has role antifungal agent (CHEBI:35718)
yanuthone L (CHEBI:133034) is a acetate ester (CHEBI:47622)
yanuthone L (CHEBI:133034) is a class I yanuthone (CHEBI:133075)
yanuthone L (CHEBI:133034) is a primary alcohol (CHEBI:15734)
IUPAC Name 
(1R,2R,6R)-6-[(2E,6E,10E)-12-hydroxy-3,7,11-trimethyldodeca-2,6,10-trien-1-yl]-3-methyl-5-oxo-7-oxabicyclo[4.1.0]hept-3-en-2-yl acetate
Synonym  Source
yanuthone-LChEBI
Registry NumbersSources
Reaxys:27991880Reaxys
Citations