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CHEBI:66253 - topopyrone B

ChEBI IDCHEBI:66253
ChEBI Nametopopyrone B
Stars
DefinitionA naphthochromene that is 4H-naphtho[2,3-g]chromene-4,6,11-trione substituted by a chloro group at position 8, hydroxy groups at positions 5, 7 and 9 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.
Last Modified6 June 2016
DownloadsMolfile
FormulaC18H9ClO7
Net Charge0
Average Mass372.716
Monoisotopic Mass372.00368
SMILESCc1cc(=O)c2c(O)c3c(cc2o1)C(=O)c1cc(O)c(Cl)c(O)c1C3=O
InChIInChI=1S/C18H9ClO7/c1-5-2-8(20)13-10(26-5)4-7-11(17(13)24)16(23)12-6(15(7)22)3-9(21)14(19)18(12)25/h2-4,21,24-25H,1H3
InChIKeyXQMOGUIQWMFPBF-UHFFFAOYSA-N
Species of MetaboliteComponentSourceComments
Phoma (ncbitaxon:37463) - PubMed (11099218) Strain: BAUA 2861
Roles Classification
Biological Roles:
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:
antineoplastic agent  A substance that inhibits or prevents the proliferation of neoplasms.
ChEBI Ontology
Outgoing Relation(s)
topopyrone B (CHEBI:66253) has role antimicrobial agent (CHEBI:33281)
topopyrone B (CHEBI:66253) has role antineoplastic agent (CHEBI:35610)
topopyrone B (CHEBI:66253) has role antiviral agent (CHEBI:22587)
topopyrone B (CHEBI:66253) has role EC 5.99.1.2 (DNA topoisomerase) inhibitor (CHEBI:50276)
topopyrone B (CHEBI:66253) has role metabolite (CHEBI:25212)
topopyrone B (CHEBI:66253) is a p-quinones (CHEBI:25830)
topopyrone B (CHEBI:66253) is a naphthochromene (CHEBI:68504)
topopyrone B (CHEBI:66253) is a organochlorine compound (CHEBI:36683)
topopyrone B (CHEBI:66253) is a phenols (CHEBI:33853)
IUPAC Name 
8-chloro-5,7,9-trihydroxy-2-methyl-4H-naphtho[2,3-g]chromene-4,6,11-trione
Registry NumbersSources
Reaxys:8732205Reaxys
Citations