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CHEBI:68787 - rubrorotiorin

ChEBI IDCHEBI:68787
ChEBI Namerubrorotiorin
Stars
DefinitionAn azaphilone that is 6,6a-dihydro-8H-furo[2,3-h]isochromen-6,8(6aH)-dione substituted by an acetyl group at position 9, a chloro group a position 5, a 3,5-dimethylhepta-1,3-dien-1-yl group at position 3 and a methyl group at position 6a. Isolated from Chaetomium cupreum, it exhibits antifungal activity.
Last Modified15 October 2013
DownloadsMolfile
FormulaC23H23ClO5
Net Charge0
Average Mass414.885
Monoisotopic Mass414.12340
SMILESCC[C@H](C)/C=C(C)/C=C/C1=CC2=C(Cl)C(=O)[C@@]3(C)OC(=O)C(C(C)=O)=C3C2=CO1
InChIInChI=1S/C23H23ClO5/c1-6-12(2)9-13(3)7-8-15-10-16-17(11-28-15)19-18(14(4)25)22(27)29-23(19,5)21(26)20(16)24/h7-12H,6H2,1-5H3/b8-7+,13-9+/t12-,23-/m0/s1
InChIKeyQJSWSNAZIVGTFZ-NPQXMUAYSA-N
Species of MetaboliteComponentSourceComments
Chaetomium cupreum (ncbitaxon:155874) - PubMed (16792406)
Roles Classification
Biological Roles:
Chaetomium metabolite  Any fungal metabolite produced during a metabolic reaction in the mould, Chaetomium.
antifungal agent  An antimicrobial agent that destroys fungi by suppressing their ability to grow or reproduce.
fungal metabolite  Any eukaryotic metabolite produced during a metabolic reaction in fungi, the kingdom that includes microorganisms such as the yeasts and moulds.
ChEBI Ontology
Outgoing Relation(s)
rubrorotiorin (CHEBI:68787) has role Chaetomium metabolite (CHEBI:76960)
rubrorotiorin (CHEBI:68787) has role antifungal agent (CHEBI:35718)
rubrorotiorin (CHEBI:68787) is a azaphilone (CHEBI:50941)
rubrorotiorin (CHEBI:68787) is a enone (CHEBI:51689)
rubrorotiorin (CHEBI:68787) is a methyl ketone (CHEBI:51867)
rubrorotiorin (CHEBI:68787) is a organic heterotricyclic compound (CHEBI:26979)
rubrorotiorin (CHEBI:68787) is a organochlorine compound (CHEBI:36683)
rubrorotiorin (CHEBI:68787) is a γ-lactone (CHEBI:37581)
IUPAC Name 
(6aS)-9-acetyl-5-chloro-3-[(1E,3E,5S)-3,5-dimethylhepta-1,3-dien-1-yl]-6a-methyl-6H-furo[2,3-h]isochromene-6,8(6aH)-dione
Manual XrefsDatabases
10176672ChemSpider
Registry NumbersSources
Reaxys:15840539Reaxys
CAS:28763-04-4ChemIDplus
Citations