chermesinone C (CHEBI:67398)

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ChEBI Name	chermesinone C

ChEBI ID	CHEBI:67398

Definition	An azaphilone that is 9a,9b-dihydro-1H-furo[2,3-h]isochromene-6,8(6aH,9H)-dione substituted by a hydroxy group at position 1, 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

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Formula

C18H22O6

Net Charge

Average Mass

334.36370

Monoisotopic Mass

334.14164

InChI

InChI=1S/C18H22O6/c1-5-8(2)15(20)13-14-12-10(6-9(3)23-16(12)21)7-11(19)18(14,4)24-17(13)22/h6-8,12-14,16,21H,5H2,1-4H3/t8-,12+,13-,14+,16-,18-/m0/s1

InChIKey

POKFFFWIOJPOJZ-OADPAQMCSA-N

SMILES

CC[C@H](C)C(=O)[C@@H]1[C@H]2[C@@H]3[C@@H](O)OC(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 C (CHEBI:67398) has role Penicillium metabolite (CHEBI:76964) chermesinone C (CHEBI:67398) is a γ-lactone (CHEBI:37581) chermesinone C (CHEBI:67398) is a azaphilone (CHEBI:50941) chermesinone C (CHEBI:67398) is a enone (CHEBI:51689) chermesinone C (CHEBI:67398) is a organic heterotricyclic compound (CHEBI:26979) chermesinone C (CHEBI:67398) is a secondary alcohol (CHEBI:35681)

IUPAC Name

rel-(1S,6aR,9S,9aR,9bS)-1-hydroxy-3,6a-dimethyl-9-[(2S)-2-methylbutanoyl]-9a,9b-dihydro-1H-furo[2,3-h]isochromene-6,8(6aH,9H)-dione

Registry Number	Type	Source
21548621	Reaxys Registry Number	Reaxys

Citation	Type	Source
21510637	PubMed citation	Europe PMC

Last Modified

06 November 2013