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CHEBI:66427 - myrsinoic acid B

ChEBI IDCHEBI:66427
ChEBI Namemyrsinoic acid B
Stars
DefinitionA member of the class of 1-benzofurans that is 2,3-dihydro-1-benzofuran substituted by a carboxy group at position 5, a 1',5'-dimethyl-1'-hydroxy-4'-hexenyl group at position 2 and a prenyl group at position 7. Isolated from Myrsine seguinii, it exhibits anti-inflammatory activity.
Last Modified15 April 2013
DownloadsMolfile
FormulaC22H30O4
Net Charge0
Average Mass358.478
Monoisotopic Mass358.21441
SMILESCC(C)=CCCC(C)(O)C1Cc2cc(C(=O)O)cc(CC=C(C)C)c2O1
InChIInChI=1S/C22H30O4/c1-14(2)7-6-10-22(5,25)19-13-17-12-18(21(23)24)11-16(20(17)26-19)9-8-15(3)4/h7-8,11-12,19,25H,6,9-10,13H2,1-5H3,(H,23,24)
InChIKeyGZLIPAFSJXROEC-UHFFFAOYSA-N
Species of MetaboliteComponentSourceComments
Myrsine seguinii (ncbitaxon:276780)
leaf (BTO:0000713) PubMed (12005065) fresh leaves and twigs
twig (BTO:0001411) PubMed (12005065) fresh leaves and twigs
Roles Classification
Chemical Role:
Bronsted acid  A molecular entity capable of donating a hydron to an acceptor (Brønsted base).
Biological Roles:
EC 4.4.1.11 (methionine gamma-lyase) inhibitor  An EC 4.4.1.* (C‒S lyase) inhibitor that interferes with the action of the enzyme methionine γ-lyase (EC 4.4.1.11).
metabolite  Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
Application:
anti-inflammatory agent  Any compound that has anti-inflammatory effects.
ChEBI Ontology
Outgoing Relation(s)
myrsinoic acid B (CHEBI:66427) has role anti-inflammatory agent (CHEBI:67079)
myrsinoic acid B (CHEBI:66427) has role EC 4.4.1.11 (methionine γ-lyase) inhibitor (CHEBI:73196)
myrsinoic acid B (CHEBI:66427) has role metabolite (CHEBI:25212)
myrsinoic acid B (CHEBI:66427) is a 1-benzofurans (CHEBI:38830)
myrsinoic acid B (CHEBI:66427) is a monocarboxylic acid (CHEBI:25384)
IUPAC Name 
2-(2-hydroxy-6-methylhept-5-en-2-yl)-7-(3-methylbut-2-en-1-yl)-2,3-dihydro-1-benzofuran-5-carboxylic acid
Synonym  Source
5-carboxy-2,3-dihydro-2-(1',5'-dimethyl-1'-hydroxy-4'-hexenyl)-7-(3''-methyl-2''-butenyl)benzofuranChEBI
Manual XrefsDatabases
US2010069477Patent
KR20090035605Patent
CN101495127Patent
WO2008013062Patent
Registry NumbersSources
Reaxys:4758095Reaxys
Citations