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CHEBI:66711 - methyl brevifolincarboxylate

ChEBI IDCHEBI:66711
ChEBI Namemethyl brevifolincarboxylate
Stars
DefinitionAn organic heterotricyclic compound that is 1,2,3,5-tetrahydrocyclopenta[c]isochromene substituted by hydroxy groups at positions 7, 8 and 9, oxo groups at positions 3 and 5 and a methoxycarbonyl group at position 1. Isolated from Phyllanthus urinaria and Phyllanthus niruri, it exhibits vasorelaxant activity.
Last Modified9 April 2013
DownloadsMolfile
FormulaC14H10O8
Net Charge0
Average Mass306.226
Monoisotopic Mass306.03757
SMILESCOC(=O)C1CC(=O)c2oc(=O)c3cc(O)c(O)c(O)c3c21
InChIInChI=1S/C14H10O8/c1-21-13(19)5-3-7(16)12-9(5)8-4(14(20)22-12)2-6(15)10(17)11(8)18/h2,5,15,17-18H,3H2,1H3
InChIKeyJNWDNAASYHRXMG-UHFFFAOYSA-N
Species of MetaboliteComponentSourceComments
Phyllanthus urinaria (ncbitaxon:296035) - Article (ACTA PHARM SIN,1993,28,11,829)
Phyllanthus niruri (ncbitaxon:296034) leaf (BTO:0000713) PubMed (16394535)
Roles Classification
Chemical Role:
radical scavenger  A role played by a substance that can react readily with, and thereby eliminate, radicals.
Biological Roles:
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.
EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor  A topoisomerase inhibitor that inhibits DNA topoisomerase (ATP-hydrolysing), EC 5.99.1.3 (also known as topoisomerase II and as DNA gyrase), which catalyses ATP-dependent breakage of both strands of DNA, passage of the unbroken strands through the breaks, and rejoining of the broken strands.
metabolite  Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
Applications:
vasodilator agent  A drug used to cause dilation of the blood vessels.
platelet aggregation inhibitor  A drug or agent which antagonizes or impairs any mechanism leading to blood platelet aggregation, whether during the phases of activation and shape change or following the dense-granule release reaction and stimulation of the prostaglandin-thromboxane system.
ChEBI Ontology
Outgoing Relation(s)
methyl brevifolincarboxylate (CHEBI:66711) has role EC 5.99.1.2 (DNA topoisomerase) inhibitor (CHEBI:50276)
methyl brevifolincarboxylate (CHEBI:66711) has role EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor (CHEBI:50750)
methyl brevifolincarboxylate (CHEBI:66711) has role metabolite (CHEBI:25212)
methyl brevifolincarboxylate (CHEBI:66711) has role platelet aggregation inhibitor (CHEBI:50427)
methyl brevifolincarboxylate (CHEBI:66711) has role radical scavenger (CHEBI:48578)
methyl brevifolincarboxylate (CHEBI:66711) has role vasodilator agent (CHEBI:35620)
methyl brevifolincarboxylate (CHEBI:66711) is a cyclic ketone (CHEBI:3992)
methyl brevifolincarboxylate (CHEBI:66711) is a organic heterotricyclic compound (CHEBI:26979)
methyl brevifolincarboxylate (CHEBI:66711) is a phenols (CHEBI:33853)
methyl brevifolincarboxylate (CHEBI:66711) is a δ-lactone (CHEBI:18946)
IUPAC Name 
methyl 7,8,9-trihydroxy-3,5-dioxo-1,2,3,5-tetrahydrocyclopenta[c]isochromene-1-carboxylate
Registry NumbersSources
Reaxys:10289547Reaxys
CAS:154702-76-8ChemIDplus
Citations