CHEBI:66625 - nidulalin A

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ChEBI Name nidulalin A
ChEBI ID CHEBI:66625
Definition A 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.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C16H14O6
Net Charge 0
Average Mass 302.27880
Monoisotopic Mass 302.07904
InChI InChI=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
InChIKey BVPTZDRKEDPTOX-WBMJQRKESA-N
SMILES COC(=O)[C@]12Oc3cc(C)cc(O)c3C(=O)C1=CC=C[C@H]2O
Metabolite of Species Details
Emericella nidulans var. lata (NCBI:txid41734) See: CHEM PHARM BULL,1994,42,1720
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.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing 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 Number Type Source
7043293 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
10509910 PubMed citation Europe PMC
10784438 PubMed citation Europe PMC
16595963 PubMed citation Europe PMC
19575043 PubMed citation Europe PMC
9711252 PubMed citation Europe PMC
Last Modified
09 March 2018
General Comment
2012-07-27 CHEM PHARM BULL,1994,42,1720