CHEBI:133095 - yanuthone X1

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ChEBI Name yanuthone X1
ChEBI ID CHEBI:133095
ChEBI ASCII Name yanuthone X1
Definition A class II yanuthone that is yanuthone X2 in which the hydroxy group at position 4 of the 5,6-epoxycyclohex-2-en-1-one core has been converted to the corresponding acetate ester. Like yanuthone X2, yanuthone X1 has been isolated from the filamentous fungus Aspergillus niger, but shows much lower antifungal activity towards the pathogenic yeast Candida albicans than yanuthone X2 (IC50 >100 μM for yanuthone X1, compared with = 51.7 ±4.7 μM for yanuthone X2).
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C24H34O5
Net Charge 0
Average Mass 402.525
Monoisotopic Mass 402.24062
InChI InChI=1S/C24H34O5/c1-16(2)9-7-10-17(3)11-8-12-18(4)13-14-24-21(26)15-20(27-6)22(23(24)29-24)28-19(5)25/h9,11,13,15,22-23H,7-8,10,12,14H2,1-6H3/b17-11+,18-13+/t22-,23-,24+/m1/s1
InChIKey NHRZKPRMGXJSET-YVCJEVKHSA-N
SMILES C/C(=C\CC\C(\C)=C\C[C@]12C(C=C([C@H]([C@H]1O2)OC(=O)C)OC)=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 .
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 X1 (CHEBI:133095) has functional parent yanuthone X2 (CHEBI:133037)
yanuthone X1 (CHEBI:133095) has role Aspergillus metabolite (CHEBI:76956)
yanuthone X1 (CHEBI:133095) is a acetate ester (CHEBI:47622)
yanuthone X1 (CHEBI:133095) is a class II yanuthone (CHEBI:133081)
yanuthone X1 (CHEBI:133095) is a enol ether (CHEBI:47985)
IUPAC Name
(1R,2S,6R)-3-methoxy-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
Citation Waiting for Citations Type Source
24684908 PubMed citation Europe PMC
Last Modified
20 August 2016