CHEBI:133034 - yanuthone L

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ChEBI Name yanuthone L
ChEBI ID CHEBI:133034
Definition A 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that is yanuthone K in which a hydrogen of the pro-E methyl group at the terminus of the farnesyl substituent has been replaced by a hydroxy group.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).
Stars This entity has been manually annotated by the ChEBI Team.
Submitter Julian Brandl
Supplier Information
Download Molfile XML SDF
Formula C24H34O5
Net Charge 0
Average Mass 402.525
Monoisotopic Mass 402.24062
InChI InChI=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
InChIKey ULUIYCOUZXIMPX-XXMQOAAMSA-N
SMILES C1(C=C([C@H]([C@@H]2[C@@]1(C/C=C(/CC/C=C(/CC/C=C(/CO)\C)\C)\C)O2)OC(C)=O)C)=O
Metabolite of Species Details
Aspergillus niger ATCC 1015 (NCBI:txid380704) of strain KB1001 See: PubMed
Roles Classification
Biological Role(s): 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.
(via meroterpenoid )
View more via ChEBI Ontology
ChEBI Ontology
Outgoing 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-L ChEBI
Registry Number Type Source
27991880 Reaxys Registry Number Reaxys
Citation Waiting for Citations Type Source
25293978 PubMed citation SUBMITTER
Last Modified
19 August 2016