CHEBI:68699 - (−)-rotiorin

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ChEBI Name (−)-rotiorin
ChEBI ID CHEBI:68699
ChEBI ASCII Name (-)-rotiorin
Definition An azaphilone that is 9,9a-dihydro-2H-furo[3,2-g]isochromen-2-one substituted by an acetyl group at position 3, an oxo group at position 9, a 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.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C23H24O5
Net Charge 0
Average Mass 380.43370
Monoisotopic Mass 380.16237
InChI InChI=1S/C23H24O5/c1-6-13(2)9-14(3)7-8-17-10-16-11-19-20(15(4)24)22(26)28-23(19,5)21(25)18(16)12-27-17/h7-13H,6H2,1-5H3/b8-7+,14-9+/t13-,23+/m0/s1
InChIKey CJMOMVNHRUTOJX-SEAFAFSMSA-N
SMILES CC[C@H](C)\C=C(C)\C=C\C1=CC2=CC3=C(C(C)=O)C(=O)O[C@@]3(C)C(=O)C2=CO1
Metabolite of Species Details
Chaetomium cupreum (NCBI:txidtxid155874) See: PubMed
Roles Classification
Biological Role(s): 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.
(via azaphilone )
View more via ChEBI Ontology
ChEBI Ontology
Outgoing (−)-rotiorin (CHEBI:68699) has role Chaetomium metabolite (CHEBI:76960)
(−)-rotiorin (CHEBI:68699) has role antifungal agent (CHEBI:35718)
(−)-rotiorin (CHEBI:68699) is a γ-lactone (CHEBI:37581)
(−)-rotiorin (CHEBI:68699) is a azaphilone (CHEBI:50941)
(−)-rotiorin (CHEBI:68699) is a enone (CHEBI:51689)
(−)-rotiorin (CHEBI:68699) is a methyl ketone (CHEBI:51867)
(−)-rotiorin (CHEBI:68699) is a organic heterotricyclic compound (CHEBI:26979)
IUPAC Name
(9aR)-3-acetyl-6-[(1E,3E,5S)-3,5-dimethylhepta-1,3-dien-1-yl]-9a-methyl-2H-furo[3,2-g]isochromene-2,9(9aH)-dione
Manual Xref Database
255838 ChemSpider
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Registry Number Type Source
15840534 Reaxys Registry Number Reaxys
Citation Waiting for Citations Type Source
16792406 PubMed citation Europe PMC
Last Modified
14 October 2013