CHEBI:66254 - topopyrone C

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ChEBI Name topopyrone C
ChEBI ID CHEBI:66254
Definition A naphthochromene that is 4H-naphtho[2,3-h]chromene-4,7,12-trione substituted by hydroxy groups at positions 5, 9 and 11 and a methyl group at position 2. It is isolated from fungal strains Phoma and Penicillium and acts as an inhibitor of the enzyme topoisomerase I.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C18H10O7
Net Charge 0
Average Mass 338.26780
Monoisotopic Mass 338.04265
InChI InChI=1S/C18H10O7/c1-6-2-10(20)15-12(22)5-9-14(18(15)25-6)17(24)13-8(16(9)23)3-7(19)4-11(13)21/h2-5,19,21-22H,1H3
InChIKey AWDAPFGGFWZKGB-UHFFFAOYSA-N
SMILES Cc1cc(=O)c2c(O)cc3C(=O)c4cc(O)cc(O)c4C(=O)c3c2o1
Metabolite of Species Details
Phoma (NCBI:txid37463) of strain BAUA 2861 See: PubMed
Penicillium (NCBI:txid5073) of strain BAUA 4206 See: PubMed
Roles Classification
Biological Role(s): antiviral agent
A substance that destroys or inhibits replication of viruses.
EC 5.99.1.2 (DNA topoisomerase) inhibitor
A topoisomerase inhibitor that inhibits the bacterial enzymes of the DNA topoisomerases, Type I class (EC 5.99.1.2) that catalyze ATP-independent breakage of one of the two strands of DNA, passage of the unbroken strand through the break, and rejoining of the broken strand. These bacterial enzymes reduce the topological stress in the DNA structure by relaxing negatively, but not positively, supercoiled DNA.
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.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing topopyrone C (CHEBI:66254) has role Penicillium metabolite (CHEBI:76964)
topopyrone C (CHEBI:66254) has role antimicrobial agent (CHEBI:33281)
topopyrone C (CHEBI:66254) has role antineoplastic agent (CHEBI:35610)
topopyrone C (CHEBI:66254) has role antiviral agent (CHEBI:22587)
topopyrone C (CHEBI:66254) has role EC 5.99.1.2 (DNA topoisomerase) inhibitor (CHEBI:50276)
topopyrone C (CHEBI:66254) is a p-quinones (CHEBI:25830)
topopyrone C (CHEBI:66254) is a naphthochromene (CHEBI:68504)
topopyrone C (CHEBI:66254) is a phenols (CHEBI:33853)
IUPAC Name
5,9,11-trihydroxy-2-methyl-4H-naphtho[2,3-h]chromene-4,7,12-trione
Registry Number Type Source
8728026 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
11099218 PubMed citation Europe PMC
11099219 PubMed citation Europe PMC
18248813 PubMed citation Europe PMC
Last Modified
06 June 2016