topopyrone D (CHEBI:66255)

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ChEBI Name	topopyrone D

ChEBI ID	CHEBI:66255

Definition	A naphthochromene that is 4H-naphtho[2,3-g]chromene-4,6,11-trione substituted by hydroxy groups at positions 5, 7 and 9 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

Download	Molfile XML SDF

Formula

C18H10O7

Net Charge

Average Mass

338.26780

Monoisotopic Mass

338.04265

InChI

InChI=1S/C18H10O7/c1-6-2-10(20)15-12(25-6)5-9-14(18(15)24)17(23)13-8(16(9)22)3-7(19)4-11(13)21/h2-5,19,21,24H,1H3

InChIKey

WKOUXLOBNJWENY-UHFFFAOYSA-N

SMILES

Cc1cc(=O)c2c(O)c3C(=O)c4c(O)cc(O)cc4C(=O)c3cc2o1

Roles Classification
Biological Role(s):	antimicrobial agent A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans. 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.

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

ChEBI Ontology
Outgoing	topopyrone D (CHEBI:66255) has role Penicillium metabolite (CHEBI:76964) topopyrone D (CHEBI:66255) has role antimicrobial agent (CHEBI:33281) topopyrone D (CHEBI:66255) has role antineoplastic agent (CHEBI:35610) topopyrone D (CHEBI:66255) has role antiviral agent (CHEBI:22587) topopyrone D (CHEBI:66255) has role EC 5.99.1.2 (DNA topoisomerase) inhibitor (CHEBI:50276) topopyrone D (CHEBI:66255) is a p-quinones (CHEBI:25830) topopyrone D (CHEBI:66255) is a naphthochromene (CHEBI:68504) topopyrone D (CHEBI:66255) is a phenols (CHEBI:33853)

IUPAC Name

5,7,9-trihydroxy-2-methyl-4H-naphtho[2,3-g]chromene-4,6,11-trione

Registry Number	Type	Source
8728809	Reaxys Registry Number	Reaxys

Last Modified

06 June 2016