EMBL-EBI | Chemical Biology | ChEBI

Example searches: iron*, InChI=1S/CH4O/c1-2/h2H,1H3, caffeine | Advanced Search

CHEBI:66254 - topopyrone C

ChEBI IDCHEBI:66254
ChEBI Nametopopyrone C
Stars
DefinitionA 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.
Last Modified6 June 2016
DownloadsMolfile
FormulaC18H10O7
Net Charge0
Average Mass338.271
Monoisotopic Mass338.04265
SMILESCc1cc(=O)c2c(O)cc3c(c2o1)C(=O)c1c(O)cc(O)cc1C3=O
InChIInChI=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
InChIKeyAWDAPFGGFWZKGB-UHFFFAOYSA-N
Species of MetaboliteComponentSourceComments
Penicillium (ncbitaxon:5073) - PubMed (11099218) Strain: BAUA 4206
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.
Penicillium metabolite  Any fungal metabolite produced during a metabolic reaction in Penicillium.
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.
Application:
antineoplastic agent  A substance that inhibits or prevents the proliferation of neoplasms.
ChEBI Ontology
Outgoing Relation(s)
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 NumbersSources
Reaxys:8728026Reaxys
Citations