CHEBI:66711 - methyl brevifolincarboxylate

Main ChEBI Ontology Automatic Xrefs Reactions Pathways Models
ChEBI Name methyl brevifolincarboxylate
ChEBI ID CHEBI:66711
Definition An 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.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
Download Molfile XML SDF
Formula C14H10O8
Net Charge 0
Average Mass 306.22440
Monoisotopic Mass 306.038
InChI InChI=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
InChIKey JNWDNAASYHRXMG-UHFFFAOYSA-N
SMILES COC(=O)C1CC(=O)c2oc(=O)c3cc(O)c(O)c(O)c3c12
Metabolite of Species Details
Phyllanthus niruri (NCBI:296034) Found in leaf (BTO:0000713). See: PubMed
Phyllanthus urinaria (NCBI:296035) See: ACTA PHARM SIN,1993,28,11,829
Roles Classification
Chemical Role(s): radical scavenger
A role played by a substance that can react readily with, and thereby eliminate, radicals.
Biological Role(s): metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
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.
Application(s): 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.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing 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 δ-lactone (CHEBI:18946)
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)
IUPAC Name
methyl 7,8,9-trihydroxy-3,5-dioxo-1,2,3,5-tetrahydrocyclopenta[c]isochromene-1-carboxylate
Registry Numbers Types Sources
10289547 Reaxys Registry Number Reaxys
154702-76-8 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
16394535 PubMed citation Europe PMC
17268086 PubMed citation Europe PMC
18187278 PubMed citation Europe PMC
18557426 PubMed citation Europe PMC
20433066 PubMed citation Europe PMC
Last Modified
09 April 2013
General Comment
2012-07-27 ACTA PHARM SIN,1993,28,11,829