CHEBI:66426 - myrsinoic acid A

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ChEBI Name myrsinoic acid A
ChEBI ID CHEBI:66426
Definition A 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.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
Download Molfile XML SDF
Formula C22H30O3
Net Charge 0
Average Mass 342.47180
Monoisotopic Mass 342.21949
InChI InChI=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+
InChIKey SUXGLLRPXXXJER-LICLKQGHSA-N
SMILES CC(C)=CCC\C(C)=C\Cc1cc(cc(CC=C(C)C)c1O)C(O)=O
Metabolite of Species Details
Myrsine seguinii (NCBI:txid276780) Found in twig (BTO:0001411). fresh leaves and twigs See: PubMed
Myrsine seguinii (NCBI:txid276780) Found in leaf (BTO:0000713). fresh leaves and twigs See: PubMed
Roles Classification
Chemical Role(s): Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
(via oxoacid )
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 4.4.1.11 (methionine gamma-lyase) inhibitor
An EC 4.4.1.* (C1S lyase) inhibitor that interferes with the action of the enzyme methionine gamma-lyase (EC 4.4.1.11).
Application(s): anti-inflammatory agent
Any compound that has anti-inflammatory effects.
antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing 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 acid ChEBI
Manual Xrefs Databases
CN101495127 Patent
KR20090035605 Patent
US2010069477 Patent
US2011060047 Patent
WO2008013062 Patent
WO2011014257 Patent
View more database links
Registry Number Type Source
20135097 Reaxys Registry Number Reaxys
Citation Waiting for Citations Type Source
12005065 PubMed citation Europe PMC
Last Modified
15 April 2013