chermesinone B (CHEBI:67397)

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ChEBI Name	chermesinone B

ChEBI ID	CHEBI:67397

Definition	An azaphilone that is 9,9a-dihydro-6H-furo[2,3-h]isochromene-6,8(6aH)-dione substituted by methyl groups at positions 3 and 6a and a 2-methylbutanoyl group at position 9. It has been isolated from the culture of the mangrove endophytic fungus Penicillium chermesinum.

Stars	This entity has been manually annotated by the ChEBI Team.

Supplier Information

Download	Molfile XML SDF

Formula

C18H20O5

Net Charge

Average Mass

316.34840

Monoisotopic Mass

316.13107

InChI

InChI=1S/C18H20O5/c1-5-9(2)16(20)14-15-12-8-22-10(3)6-11(12)7-13(19)18(15,4)23-17(14)21/h6-9,14-15H,5H2,1-4H3/t9-,14-,15+,18-/m0/s1

InChIKey

MZMGICPQNSXAGE-SRSSHDMCSA-N

SMILES

CC[C@H](C)C(=O)[C@@H]1[C@H]2C3=COC(C)=CC3=CC(=O)[C@]2(C)OC1=O

Metabolite of Species	Details
Penicillium chermesinum (NCBI:txid63820)	Ethylacetate extract of endophytic fungus isolated from stem of the mangrove plant Kandelia candel of strain ZH4 E2 See: PubMed

Roles Classification
Biological Role(s):	Penicillium metabolite Any fungal metabolite produced during a metabolic reaction in Penicillium. 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	chermesinone B (CHEBI:67397) has role Penicillium metabolite (CHEBI:76964) chermesinone B (CHEBI:67397) is a γ-lactone (CHEBI:37581) chermesinone B (CHEBI:67397) is a azaphilone (CHEBI:50941) chermesinone B (CHEBI:67397) is a enone (CHEBI:51689) chermesinone B (CHEBI:67397) is a organic heterotricyclic compound (CHEBI:26979)

IUPAC Name

rel-(6aR,9S,9aS)-3,6a-dimethyl-9-[(2S)-2-methylbutanoyl]-9,9a-dihydro-6H-furo[2,3-h]isochromene-6,8(6aH)-dione

Registry Number	Type	Source
21548619	Reaxys Registry Number	Reaxys

Citation	Type	Source
21510637	PubMed citation	Europe PMC

Last Modified

06 November 2013