(-)-rotiorin (CHEBI:68699)

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CHEBI:68699 - (−)-rotiorin

ChEBI ID	CHEBI:68699
ChEBI Name	(−)-rotiorin
Stars
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.
Last Modified	14 October 2013
Downloads	Molfile

Formula	C23H24O5
Net Charge	0
Average Mass	380.440
Monoisotopic Mass	380.16237
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
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

Species of Metabolite	Component	Source	Comments
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)
	(−)-rotiorin (CHEBI:68699) has role Chaetomium metabolite (CHEBI:76960)
	(−)-rotiorin (CHEBI:68699) has role antifungal agent (CHEBI:35718)
	(−)-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)
	(−)-rotiorin (CHEBI:68699) is a γ-lactone (CHEBI:37581)

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 Xrefs	Databases
255838	ChemSpider

Registry Numbers	Sources
Reaxys:15840534	Reaxys

Citations