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CHEBI:133037 - yanuthone X2

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:
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.
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