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CHEBI:133037 - yanuthone X2

Default Structure
ChEBI IDCHEBI:133037
ChEBI Nameyanuthone X2
Stars
ASCII Nameyanuthone X2
DefinitionA class II yanuthone that is 5,6-epoxy-cyclohex-2-en-1-one which is substituted at positions 3, 4, and 6 by methoxy, hydroxy, and trans,trans-farnesyl groups, respectively (the 4S,5R,6R stereoisomer). Isolated from the filamentous fungus Aspergillus niger, it shows antifungal activity towards the pathogenic yeast Candida albicans (IC50 = 51.7 ±4.7 μM).
Last Modified23 August 2016
SubmitterJubra
DownloadsMolfile
FormulaC22H32O4
Net Charge0
Average Mass360.494
Monoisotopic Mass360.23006
SMILESCOC1=CC(=O)[C@]2(C/C=C(\C)CC/C=C(\C)CCC=C(C)C)O[C@@H]2[C@@H]1O
InChIInChI=1S/C22H32O4/c1-15(2)8-6-9-16(3)10-7-11-17(4)12-13-22-19(23)14-18(25-5)20(24)21(22)26-22/h8,10,12,14,20-21,24H,6-7,9,11,13H2,1-5H3/b16-10+,17-12+/t20-,21-,22+/m1/s1
InChIKeyURXBIEAAUGXNIJ-ITGDQCKOSA-N
Species of MetaboliteComponentSourceComments
Aspergillus niger ATCC 1015 (ncbitaxon:380704) - PubMed (25293978) Strain: KB1001
Roles Classification
Biological Roles:
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.
ChEBI Ontology
Outgoing Relation(s)
yanuthone X2 (CHEBI:133037) has functional parent (2-trans,6-trans)-farnesol (CHEBI:16619)
yanuthone X2 (CHEBI:133037) has role Aspergillus metabolite (CHEBI:76956)
yanuthone X2 (CHEBI:133037) has role antifungal agent (CHEBI:35718)
yanuthone X2 (CHEBI:133037) is a class II yanuthone (CHEBI:133081)
yanuthone X2 (CHEBI:133037) is a enol ether (CHEBI:47985)
yanuthone X2 (CHEBI:133037) is a secondary alcohol (CHEBI:35681)
Incoming Relation(s)
yanuthone X1 (CHEBI:133095) has functional parent yanuthone X2 (CHEBI:133037)
IUPAC Name 
(1R,5S,6R)-5-hydroxy-4-methoxy-1-[(2E,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-yl]-7-oxabicyclo[4.1.0]hept-3-en-2-one
Synonyms  Source
yanuthone X2ChEBI
yanuthone-X2ChEBI
yanuthone-X2ChEBI
Citations