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CHEBI:133095 - yanuthone X1

ChEBI IDCHEBI:133095
ChEBI Nameyanuthone X1
Stars
ASCII Nameyanuthone X1
DefinitionA 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).
Last Modified20 August 2016
SubmitterGareth Owen
DownloadsMolfile
FormulaC24H34O5
Net Charge0
Average Mass402.531
Monoisotopic Mass402.24062
SMILESCOC1=CC(=O)[C@]2(C/C=C(\C)CC/C=C(\C)CCC=C(C)C)O[C@@H]2[C@@H]1OC(C)=O
InChIInChI=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
InChIKeyNHRZKPRMGXJSET-YVCJEVKHSA-N
Species of MetaboliteComponentSourceComments
Aspergillus niger ATCC 1015 (ncbitaxon:380704) - PubMed (24684908) Strain: KB1001
Roles Classification
Biological Roles:
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 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
Citations