F390C (CHEBI:65894)

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ChEBI Name	F390C

ChEBI ID	CHEBI:65894

Definition	A member of the class xanthones which consists of a dihydroxanthone skeleton substituted by hydroxy groups at positions 4 and 8, a hydroxymethyl group at position 6 and a methoxycarbonyl group at position 4a (the 4R,4aS stereoisomer). It is isolated from Penicillium and exhibits potent antitumour activity against both human and murine tumour cell lines.

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

Supplier Information

Download	Molfile XML SDF

Formula

C16H14O7

Net Charge

Average Mass

318.27820

Monoisotopic Mass

318.07395

InChI

InChI=1S/C16H14O7/c1-22-15(21)16-9(3-2-4-12(16)19)14(20)13-10(18)5-8(7-17)6-11(13)23-16/h2-6,12,17-19H,7H2,1H3/t12-,16+/m1/s1

InChIKey

PMHCAQUSIVAZPO-WBMJQRKESA-N

SMILES

COC(=O)[C@]12Oc3cc(CO)cc(O)c3C(=O)C1=CC=C[C@H]2O

Metabolite of Species	Details
Penicillium (NCBI:txid5073)	of strain AJ117291 See: PubMed

Roles Classification
Biological Role(s):	Penicillium metabolite Any fungal metabolite produced during a metabolic reaction in Penicillium. antimicrobial agent A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.

Application(s):	antineoplastic agent A substance that inhibits or prevents the proliferation of neoplasms.

ChEBI Ontology
Outgoing	F390C (CHEBI:65894) has role Penicillium metabolite (CHEBI:76964) F390C (CHEBI:65894) has role antimicrobial agent (CHEBI:33281) F390C (CHEBI:65894) has role antineoplastic agent (CHEBI:35610) F390C (CHEBI:65894) is a benzyl alcohols (CHEBI:22743) F390C (CHEBI:65894) is a methyl ester (CHEBI:25248) F390C (CHEBI:65894) is a phenols (CHEBI:33853) F390C (CHEBI:65894) is a xanthones (CHEBI:51149)

IUPAC Name

methyl (4R,4aS)-4,8-dihydroxy-6-(hydroxymethyl)-9-oxo-4,9-dihydro-4aH-xanthene-4a-carboxylate

Registry Number	Type	Source
8161679	Reaxys Registry Number	Reaxys

Last Modified

06 March 2015