(-)-rotiorin (CHEBI:68699)

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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

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:txid155874)	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 )

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

Registry Number	Type	Source
15840534	Reaxys Registry Number	Reaxys

Citation	Type	Source
16792406	PubMed citation	Europe PMC

Last Modified

14 October 2013