EMBL-EBI | Chemical Biology | ChEBI

Example searches: iron*, InChI=1S/CH4O/c1-2/h2H,1H3, caffeine | Advanced Search

CHEBI:156511 - poacic acid

ChEBI IDCHEBI:156511
ChEBI Namepoacic acid
Stars
DefinitionA hydroxycinnamic acid that is (2E)-3-phenylprop-2-enoic acid in which the hydrogens at positions 3, 4 and 5 are replaced by 2-(4-hydroxy-3-methoxyphenyl)ethenyl, hydroxy and methoxy groups, respectively. It is a natural product found in maize bran which exhibits antifungal activities against several fungal and oomycete pathogens including Sclerotinia sclerotiorum, Alternaria solani, and Phytophthora sojae. It inhibits β-1,3-glucan synthesis in cells walls resulting in rapid cell lysis.
Last Modified17 September 2020
SubmitterMicheal Alexander
DownloadsMolfile
FormulaC19H18O6
Net Charge0
Average Mass342.347
Monoisotopic Mass342.11034
SMILESCOc1cc(/C=C/c2cc(/C=C/C(=O)O)cc(OC)c2O)ccc1O
InChIInChI=1S/C19H18O6/c1-24-16-10-12(4-7-15(16)20)3-6-14-9-13(5-8-18(21)22)11-17(25-2)19(14)23/h3-11,20,23H,1-2H3,(H,21,22)/b6-3+,8-5+
InChIKeySLIMCXCSQXYCGL-JENUQAQBSA-N
Wikipedia
Species of MetaboliteComponentSourceComments
Zea mays (ncbitaxon:4577) - PubMed (15495409)
Zea mays subsp. mays (ncbitaxon:381124) - PubMed (25775513)
Roles Classification
Chemical Role:
Bronsted acid  A molecular entity capable of donating a hydron to an acceptor (Brønsted base).
Biological Roles:
plant metabolite  Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
antifungal agent  An antimicrobial agent that destroys fungi by suppressing their ability to grow or reproduce.
ChEBI Ontology
Outgoing Relation(s)
poacic acid (CHEBI:156511) has role antifungal agent (CHEBI:35718)
poacic acid (CHEBI:156511) has role plant metabolite (CHEBI:76924)
poacic acid (CHEBI:156511) is a hydroxycinnamic acid (CHEBI:24689)
poacic acid (CHEBI:156511) is a methoxycinnamic acid (CHEBI:61407)
poacic acid (CHEBI:156511) is a monomethoxybenzene (CHEBI:25235)
poacic acid (CHEBI:156511) is a polyphenol (CHEBI:26195)
poacic acid (CHEBI:156511) is a stilbenoid (CHEBI:26776)
IUPAC Name 
(2E)-3-{4-hydroxy-3-[(E)-2-(4-hydroxy-3-methoxyphenyl)ethenyl]-5-methoxyphenyl}prop-2-enoic acid
Synonyms  Source
decarboxylated 8,5'-diferulic acidSUBMITTER
3-(3-methoxy-4-hydroxystyryl)-4-hydroxy-5-methoxycinnamic acidChEBI
8,5'-diferulic acid (decarboxylated form)ChEBI
Manual XrefsDatabases
Decarboxylated_8,5'-diferulic_acidWikipedia
Citations