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CHEBI:66428 - myrsinoic acid C

ChEBI IDCHEBI:66428
ChEBI Namemyrsinoic acid C
Stars
DefinitionA member of the class of chromanes that is 3,4-dihydro-2H-chromene substituted by a carboxy group at position 6, a hydroxy group at position 3, a methyl and a 4-methylpent-3-en-1-yl group at position 2 and a prenyl group at position 8 (the 2S,3S stereoisomer). Isolated from in Myrsine seguinii, it exhibits anti-inflammatory activity.
Last Modified15 April 2013
DownloadsMolfile
FormulaC22H30O4
Net Charge0
Average Mass358.478
Monoisotopic Mass358.21441
SMILESCC(C)=CCC[C@]1(C)Oc2c(CC=C(C)C)cc(C(=O)O)cc2C[C@@H]1O
InChIInChI=1S/C22H30O4/c1-14(2)7-6-10-22(5)19(23)13-17-12-18(21(24)25)11-16(20(17)26-22)9-8-15(3)4/h7-8,11-12,19,23H,6,9-10,13H2,1-5H3,(H,24,25)/t19-,22-/m0/s1
InChIKeyBZURYTKOXWYRAG-UGKGYDQZSA-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.
Application:
anti-inflammatory agent  Any compound that has anti-inflammatory effects.
ChEBI Ontology
Outgoing Relation(s)
myrsinoic acid C (CHEBI:66428) has role anti-inflammatory agent (CHEBI:67079)
myrsinoic acid C (CHEBI:66428) has role EC 4.4.1.11 (methionine γ-lyase) inhibitor (CHEBI:73196)
myrsinoic acid C (CHEBI:66428) has role metabolite (CHEBI:25212)
myrsinoic acid C (CHEBI:66428) is a chromanes (CHEBI:23230)
myrsinoic acid C (CHEBI:66428) is a monocarboxylic acid (CHEBI:25384)
myrsinoic acid C (CHEBI:66428) is a secondary alcohol (CHEBI:35681)
IUPAC Name 
(2S,3S)-3-hydroxy-2-methyl-8-(3-methylbut-2-en-1-yl)-2-(4-methylpent-3-en-1-yl)-3,4-dihydro-2H-chromene-6-carboxylic acid
Synonym  Source
(2S),(3S)-6-carboxy-2,3-dihydro-3-hydroxy-2-methyl-2-(4'-methylpenta-3'-enyl)-8-(3''-methyl-2''-butenyl)chromanChEBI
Manual XrefsDatabases
US2010069477Patent
KR20090035605Patent
CN101495127Patent
WO2008013062Patent
Registry NumbersSources
Reaxys:9291057Reaxys
Citations