CHEBI:133035 - yanuthone K

Main ChEBI Ontology Automatic Xrefs Reactions Pathways Models
ChEBI Name yanuthone K
ChEBI ID CHEBI:133035
Definition A class I yanuthone that is 5,6-epoxy-cyclohex-2-en-1-one which is substituted at positions 3, 4, and 6 by methyl, acetoxy, and trans,trans-farnesyl groups, respectively (the R,R,R stereoisomer). Isolated from the filamentous fungus Aspergillus niger, it shows antifungal activity towards the pathogenic yeast Candida albicans (IC50 = 17.5 ±3.9 μM).
Stars This entity has been manually annotated by the ChEBI Team.
Submitter Julian Brandl
Supplier Information
Download Molfile XML SDF
Formula C24H34O4
Net Charge 0
Average Mass 386.525
Monoisotopic Mass 386.24571
InChI InChI=1S/C24H34O4/c1-16(2)9-7-10-17(3)11-8-12-18(4)13-14-24-21(26)15-19(5)22(23(24)28-24)27-20(6)25/h9,11,13,15,22-23H,7-8,10,12,14H2,1-6H3/b17-11+,18-13+/t22-,23-,24+/m1/s1
InChIKey DOKAHTTXUSOTHL-YVCJEVKHSA-N
SMILES C/C(=C\CC\C(\C)=C\C[C@]12C(C=C([C@H]([C@H]1O2)OC(C)=O)C)=O)/CCC=C(C)C
Metabolite of Species Details
Aspergillus niger ATCC 1015 (NCBI:txid380704) of strain KB1001 See: PubMed
Roles Classification
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 K (CHEBI:133035) has functional parent (2-trans,6-trans)-farnesol (CHEBI:16619)
yanuthone K (CHEBI:133035) has functional parent 7-deacetoxyyanuthone A (CHEBI:133843)
yanuthone K (CHEBI:133035) has role Aspergillus metabolite (CHEBI:76956)
yanuthone K (CHEBI:133035) has role antifungal agent (CHEBI:35718)
yanuthone K (CHEBI:133035) is a acetate ester (CHEBI:47622)
yanuthone K (CHEBI:133035) is a class I yanuthone (CHEBI:133075)
Incoming yanuthone L (CHEBI:133034) has functional parent yanuthone K (CHEBI:133035)
yanuthone M (CHEBI:133036) has functional parent yanuthone K (CHEBI:133035)
IUPAC Name
(1R,2R,6R)-3-methyl-5-oxo-6-[(2E,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-yl]-7-oxabicyclo[4.1.0]hept-3-en-2-yl acetate
Synonym Source
yanuthone-K ChEBI
Registry Number Type Source
27991879 Reaxys Registry Number Reaxys
Citation Waiting for Citations Type Source
25293978 PubMed citation SUBMITTER
Last Modified
21 November 2016