EMBL-EBI | Chemical Biology | ChEBI

Example searches: iron*, InChI=1S/CH4O/c1-2/h2H,1H3, caffeine | Advanced Search

CHEBI:133034 - yanuthone L

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that is yanuthone K in which a hydrogen of the pro-E methyl group at the terminus of the farnesyl substituent has been replaced by a hydroxy group.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:
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 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