myrsinoic acid B (CHEBI:66427)

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ChEBI Name	myrsinoic acid B

ChEBI ID	CHEBI:66427

Definition	A 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.

Stars	This entity has been manually annotated by the ChEBI Team.

Supplier Information

Download	Molfile XML SDF

Formula

C22H30O4

Net Charge

Average Mass

358.47120

Monoisotopic Mass

358.21441

InChI

InChI=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)

InChIKey

GZLIPAFSJXROEC-UHFFFAOYSA-N

SMILES

CC(C)=CCCC(C)(O)C1Cc2cc(cc(CC=C(C)C)c2O1)C(O)=O

Metabolite of Species	Details
Myrsine seguinii (NCBI:txid276780)	Found in leaf (BTO:0000713). fresh leaves and twigs See: PubMed
Myrsine seguinii (NCBI:txid276780)	Found in twig (BTO:0001411). 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.

ChEBI Ontology
Outgoing	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)benzofuran	ChEBI

Registry Number	Type	Source
4758095	Reaxys Registry Number	Reaxys

Last Modified

15 April 2013