CHEBI:156511 - poacic acid

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ChEBI Name poacic acid
ChEBI ID CHEBI:156511
Definition A 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.
Stars This entity has been manually annotated by the ChEBI Team.
Submitter Micheal Alexander
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Formula C19H18O6
Net Charge 0
Average Mass 342.347
Monoisotopic Mass 342.11034
InChI InChI=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+
InChIKey SLIMCXCSQXYCGL-JENUQAQBSA-N
SMILES COC1=C(O)C=CC(\C=C\C2=CC(\C=C\C(O)=O)=CC(OC)=C2O)=C1
Metabolite of Species Details
Zea mays subsp. mays (NCBI:txid381124) See: PubMed
Zea mays (NCBI:txid4577) 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): 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.
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ChEBI Ontology
Outgoing 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 Sources
3-(3-methoxy-4-hydroxystyryl)-4-hydroxy-5-methoxycinnamic acid ChEBI
8,5'-diferulic acid (decarboxylated form) ChEBI
decarboxylated 8,5'-diferulic acid SUBMITTER
Manual Xref Database
Decarboxylated_8,5'-diferulic_acid Wikipedia
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Citations Waiting for Citations Types Sources
15495409 PubMed citation Europe PMC
25775513 PubMed citation SUBMITTER
28787158 PubMed citation Europe PMC
30370375 PubMed citation Europe PMC
IND605665043 Agricola citation Europe PMC
IND606777426 Agricola citation Europe PMC
Last Modified
17 September 2020