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CHEBI:68786 - rotiorinol C

ChEBI IDCHEBI:68786
ChEBI Namerotiorinol C
Stars
DefinitionAn azaphilone that is 9,9a-dihydro-2H-furo[3,2-g]isochromen-2-one substituted by an acetyl group at position 3, a hydroxy group at position 9, a 7-hydroxy-3,5-dimethylhepta-1,3-dien-1-yl group at position 6 and a methyl group at position 9a. It has been isolated from Chaetomium cupreum and exhibits antifungal activity.
Last Modified14 October 2013
DownloadsMolfile
FormulaC23H26O6
Net Charge0
Average Mass398.455
Monoisotopic Mass398.17294
SMILESCC(=O)C1=C2C=C3C=C(/C=C/C(C)=C/[C@@H](C)CCO)OC=C3[C@@H](O)[C@]2(C)OC1=O
InChIInChI=1S/C23H26O6/c1-13(9-14(2)7-8-24)5-6-17-10-16-11-19-20(15(3)25)22(27)29-23(19,4)21(26)18(16)12-28-17/h5-6,9-12,14,21,24,26H,7-8H2,1-4H3/b6-5+,13-9+/t14-,21+,23+/m0/s1
InChIKeyKRCVYHUEUHHWKT-XOEIKTSYSA-N
Species of MetaboliteComponentSourceComments
Chaetomium cupreum (ncbitaxon:155874) - PubMed (16792406)
Roles Classification
Biological Roles:
antifungal agent  An antimicrobial agent that destroys fungi by suppressing their ability to grow or reproduce.
Chaetomium metabolite  Any fungal metabolite produced during a metabolic reaction in the mould, Chaetomium.
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)
rotiorinol C (CHEBI:68786) has role Chaetomium metabolite (CHEBI:76960)
rotiorinol C (CHEBI:68786) has role antifungal agent (CHEBI:35718)
rotiorinol C (CHEBI:68786) is a azaphilone (CHEBI:50941)
rotiorinol C (CHEBI:68786) is a methyl ketone (CHEBI:51867)
rotiorinol C (CHEBI:68786) is a organic heterotricyclic compound (CHEBI:26979)
rotiorinol C (CHEBI:68786) is a primary alcohol (CHEBI:15734)
rotiorinol C (CHEBI:68786) is a γ-lactone (CHEBI:37581)
IUPAC Name 
(9R,9aR)-3-acetyl-9-hydroxy-6-[(1E,3E,5S)-7-hydroxy-3,5-dimethylhepta-1,3-dien-1-yl]-9a-methyl-9,9a-dihydro-2H-furo[3,2-g]isochromen-2-one
Synonym  Source
6-acetyl-3-(3,5-dimethyl-1E,3E-heptadien-7-ol)-9R-hydroxy-8a(R)-methyl-7H-furo[2,3-g]-2-benzopyran-7-oneChEBI
Registry NumbersSources
Reaxys:15840538Reaxys
Citations