CHEBI:133036 - yanuthone M

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ChEBI Name yanuthone M
ChEBI ID CHEBI:133036
Definition A 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).
Stars This entity has been manually annotated by the ChEBI Team.
Submitter Julian Brandl
Supplier Information No supplier information found for this compound.
Download Molfile XML SDF
Formula C24H36O5
Net Charge 0
Average Mass 404.541
Monoisotopic Mass 404.25627
InChI InChI=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
InChIKey UDCFQVYVEMPFKM-CTPBMWBYSA-N
SMILES C/C(=C\CC\C(\C)=C\C[C@]12C(C=C(C([C@H]1O2)OC(C)=O)C)=O)/CCCC(C)(C)O
Metabolite of Species Details
Aspergillus niger ATCC 1015 (NCBI:txid380704) of strain KB1001 See: PubMed
Roles Classification
Chemical Role(s): Bronsted base
A molecular entity capable of accepting a hydron from a donor (Bronsted acid).
(via organic amino compound )
Biological Role(s): 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.
(via meroterpenoid )
View more via ChEBI Ontology
ChEBI Ontology
Outgoing 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-M ChEBI
Registry Number Type Source
27991881 Reaxys Registry Number Reaxys
Citation Waiting for Citations
Last Modified
19 August 2016