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CHEBI:66426 - myrsinoic acid A

ChEBI IDCHEBI:66426
ChEBI Namemyrsinoic acid A
Stars
DefinitionA monohydroxybenzoic acid that is 4-hydroxybenzoic acid substituted by a geranyl group at position 3 and a prenyl group at position 5. Isolated from Myrsine seguinii, it exhibits anti-inflammatory activity.
Last Modified15 April 2013
DownloadsMolfile
FormulaC22H30O3
Net Charge0
Average Mass342.479
Monoisotopic Mass342.21949
SMILESCC(C)=CCC/C(C)=C/Cc1cc(C(=O)O)cc(CC=C(C)C)c1O
InChIInChI=1S/C22H30O3/c1-15(2)7-6-8-17(5)10-12-19-14-20(22(24)25)13-18(21(19)23)11-9-16(3)4/h7,9-10,13-14,23H,6,8,11-12H2,1-5H3,(H,24,25)/b17-10+
InChIKeySUXGLLRPXXXJER-LICLKQGHSA-N
Species of MetaboliteComponentSourceComments
Myrsine seguinii (ncbitaxon:276780)
twig (BTO:0001411) PubMed (12005065) fresh leaves and twigs
leaf (BTO:0000713) 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.
Applications:
anti-inflammatory agent  Any compound that has anti-inflammatory effects.
antineoplastic agent  A substance that inhibits or prevents the proliferation of neoplasms.
ChEBI Ontology
Outgoing Relation(s)
myrsinoic acid A (CHEBI:66426) has role anti-inflammatory agent (CHEBI:67079)
myrsinoic acid A (CHEBI:66426) has role antineoplastic agent (CHEBI:35610)
myrsinoic acid A (CHEBI:66426) has role EC 4.4.1.11 (methionine γ-lyase) inhibitor (CHEBI:73196)
myrsinoic acid A (CHEBI:66426) has role metabolite (CHEBI:25212)
myrsinoic acid A (CHEBI:66426) is a monohydroxybenzoic acid (CHEBI:25389)
IUPAC Name 
3-[(2E)-3,7-dimethylocta-2,6-dien-1-yl]-4-hydroxy-5-(3-methylbut-2-en-1-yl)benzoic acid
Synonym  Source
3-geranyl-4-hydroxy-5-(3'-methyl-2'-butenyl)benzoic acidChEBI
Manual XrefsDatabases
US2011060047Patent
WO2011014257Patent
US2010069477Patent
KR20090035605Patent
CN101495127Patent
WO2008013062Patent
Registry NumbersSources
Reaxys:20135097Reaxys
Citations