topopyrone A (CHEBI:66252)

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ChEBI Name	topopyrone A

ChEBI ID	CHEBI:66252

Definition	A naphthochromene that is 4H-naphtho[2,3-h]chromene-4,7,12-trione substituted by a chloro group at position 10, hydroxy groups at positions 5, 9 and 11 and a methyl group at position 2. It is isolated from a fungal strain Phoma sp.BAUA2861 and acts as an inhibitor of the enzyme topoisomerase I.

Stars	This entity has been manually annotated by the ChEBI Team.

Supplier Information	ChemicalBook:CB9463336, eMolecules:30512482, eMolecules:2726153, ZINC000003881958

Download	Molfile XML SDF

Formula

C18H9ClO7

Net Charge

Average Mass

372.71300

Monoisotopic Mass

372.00368

InChI

InChI=1S/C18H9ClO7/c1-5-2-8(20)13-9(21)3-7-12(18(13)26-5)16(24)11-6(15(7)23)4-10(22)14(19)17(11)25/h2-4,21-22,25H,1H3

InChIKey

KUCMIJRMIDNZCP-UHFFFAOYSA-N

SMILES

Cc1cc(=O)c2c(O)cc3C(=O)c4cc(O)c(Cl)c(O)c4C(=O)c3c2o1

Metabolite of Species	Details
Phoma (NCBI:txid37463)	of strain BAUA 2861 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. 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. antiviral agent A substance that destroys or inhibits replication of viruses. metabolite Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.

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

ChEBI Ontology
Outgoing	topopyrone A (CHEBI:66252) has role antimicrobial agent (CHEBI:33281) topopyrone A (CHEBI:66252) has role antineoplastic agent (CHEBI:35610) topopyrone A (CHEBI:66252) has role antiviral agent (CHEBI:22587) topopyrone A (CHEBI:66252) has role EC 5.99.1.2 (DNA topoisomerase) inhibitor (CHEBI:50276) topopyrone A (CHEBI:66252) has role metabolite (CHEBI:25212) topopyrone A (CHEBI:66252) is a p-quinones (CHEBI:25830) topopyrone A (CHEBI:66252) is a naphthochromene (CHEBI:68504) topopyrone A (CHEBI:66252) is a organochlorine compound (CHEBI:36683) topopyrone A (CHEBI:66252) is a phenols (CHEBI:33853)

IUPAC Name

10-chloro-5,9,11-trihydroxy-2-methyl-4H-naphtho[2,3-h]chromene-4,7,12-trione

Registry Number	Type	Source
8730620	Reaxys Registry Number	Reaxys

Last Modified

06 June 2016