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CHEBI:65893 - F390B

ChEBI IDCHEBI:65893
ChEBI NameF390B
Stars
DefinitionA 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.
Last Modified3 March 2015
DownloadsMolfile
FormulaC18H16O7
Net Charge0
Average Mass344.319
Monoisotopic Mass344.08960
SMILESCOC(=O)[C@]12Oc3cc(C)cc(O)c3C(=O)C1=CC=C[C@H]2OC(C)=O
InChIInChI=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
InChIKeyOOXFQLGEGVNXBG-KDOFPFPSSA-N
Species of MetaboliteComponentSourceComments
Penicillium (ncbitaxon:5073) - PubMed (9711252) Strain: AJ117291
Roles Classification
Biological Roles:
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:
antineoplastic agent  A substance that inhibits or prevents the proliferation of neoplasms.
ChEBI Ontology
Outgoing Relation(s)
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 NumbersSources
Reaxys:8160407Reaxys
Citations