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CHEBI:156511 - poacic acid

Default Structure
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:
antifungal agent  An antimicrobial agent that destroys fungi by suppressing their ability to grow or reproduce.
plant metabolite  Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
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
3-(3-methoxy-4-hydroxystyryl)-4-hydroxy-5-methoxycinnamic acidChEBI
8,5'-diferulic acid (decarboxylated form)ChEBI
decarboxylated 8,5'-diferulic acidSUBMITTER
Manual XrefsDatabases
Decarboxylated_8,5'-diferulic_acidWikipedia
Citations