CHEBI:133037 - yanuthone X2

Main ChEBI Ontology Automatic Xrefs Reactions Pathways Models
ChEBI Name yanuthone X2
ChEBI ID CHEBI:133037
ChEBI ASCII Name yanuthone X2
Definition A 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).
Stars This entity has been manually annotated by the ChEBI Team.
Submitter Julian Brandl
Supplier Information
Download Molfile XML SDF
Formula C22H32O4
Net Charge 0
Average Mass 360.488
Monoisotopic Mass 360.23006
InChI InChI=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
InChIKey URXBIEAAUGXNIJ-ITGDQCKOSA-N
SMILES C/C(=C\CC\C(\C)=C\C[C@]12C(C=C([C@H]([C@H]1O2)O)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 .
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 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 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 Sources
yanuthone X2 ChEBI
yanuthone-X2 ChEBI
yanuthone-X2 ChEBI
Citation Waiting for Citations Type Source
25293978 PubMed citation SUBMITTER
Last Modified
23 August 2016