F390B (CHEBI:65893)

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ChEBI Name	F390B

ChEBI ID	CHEBI:65893

Definition	A member of the class xanthones which consists of a dihydroxanthone skeleton substituted by a acetyloxy group at position 4, a hydroxy group at position 8, a methyl 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

C18H16O7

Net Charge

Average Mass

344.31540

Monoisotopic Mass

344.08960

InChI

InChI=1S/C18H16O7/c1-9-7-12(20)15-13(8-9)25-18(17(22)23-3)11(16(15)21)5-4-6-14(18)24-10(2)19/h4-8,14,20H,1-3H3/t14-,18+/m1/s1

InChIKey

OOXFQLGEGVNXBG-KDOFPFPSSA-N

SMILES

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

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

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

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

ChEBI Ontology
Outgoing	F390B (CHEBI:65893) has role Penicillium metabolite (CHEBI:76964) F390B (CHEBI:65893) has role antimicrobial agent (CHEBI:33281) F390B (CHEBI:65893) has role antineoplastic agent (CHEBI:35610) F390B (CHEBI:65893) is a acetate ester (CHEBI:47622) F390B (CHEBI:65893) is a diester (CHEBI:51307) F390B (CHEBI:65893) is a methyl ester (CHEBI:25248) F390B (CHEBI:65893) is a phenols (CHEBI:33853) F390B (CHEBI:65893) is a xanthones (CHEBI:51149)

IUPAC Name

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

Registry Number	Type	Source
8160407	Reaxys Registry Number	Reaxys

Last Modified

03 March 2015