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CHEBI:66625 - nidulalin A

ChEBI IDCHEBI:66625
ChEBI Namenidulalin A
Stars
DefinitionA member of the class xanthones which consists of a dihydroxanthone skeleton substituted by hydroxy groups at positions 4 and 8, a methyl group at position 6 and a methoxycarbonyl group at position 4a (the 4R,4aS stereoisomer). It is isolated from Emericella nidulans var lata and Penicillium and exhibits potent antitumour activity against both human and murine tumour cell lines.
Last Modified9 March 2018
DownloadsMolfile
FormulaC16H14O6
Net Charge0
Average Mass302.282
Monoisotopic Mass302.07904
SMILESCOC(=O)[C@]12Oc3cc(C)cc(O)c3C(=O)C1=CC=C[C@H]2O
InChIInChI=1S/C16H14O6/c1-8-6-10(17)13-11(7-8)22-16(15(20)21-2)9(14(13)19)4-3-5-12(16)18/h3-7,12,17-18H,1-2H3/t12-,16+/m1/s1
InChIKeyBVPTZDRKEDPTOX-WBMJQRKESA-N
Species of MetaboliteComponentSourceComments
Emericella nidulans var. lata (ncbitaxon:41734) - Article (CHEM PHARM BULL,1994,42,1720)
Penicillium (ncbitaxon:5073) - PubMed (9711252) Strain: AJ117291
Roles Classification
Biological Roles:
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:
antineoplastic agent  A substance that inhibits or prevents the proliferation of neoplasms.
ChEBI Ontology
Outgoing Relation(s)
nidulalin A (CHEBI:66625) has role Penicillium metabolite (CHEBI:76964)
nidulalin A (CHEBI:66625) has role antimicrobial agent (CHEBI:33281)
nidulalin A (CHEBI:66625) has role antineoplastic agent (CHEBI:35610)
nidulalin A (CHEBI:66625) is a methyl ester (CHEBI:25248)
nidulalin A (CHEBI:66625) is a phenols (CHEBI:33853)
nidulalin A (CHEBI:66625) is a xanthones (CHEBI:51149)
IUPAC Name 
methyl (4R,4aS)-4,8-dihydroxy-6-methyl-9-oxo-4,9-dihydro-4aH-xanthene-4a-carboxylate
Registry NumbersSources
Reaxys:7043293Reaxys
Citations