poacic acid

CHEBI:156511 ·resolve ·ANTIFUNGAL ·EXACT SEEDED

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. — ChEBI

Machine-generated and unreviewed. Identity, structure and cross-references come straight from ChEBI's and CARD's own data; no curator has signed off on this record yet.

Classification

Strictly broader compounds or drug classes this molecule belongs to.

CHEBI:24689 CHEBI:24689
CHEBI:25235 CHEBI:25235
CHEBI:26195 CHEBI:26195
CHEBI:26776 CHEBI:26776
CHEBI:61407 CHEBI:61407

Chemical structure

Computed structure properties
Molecular formula	C19H18O6
Charge	0
Average mass	342.347 Da
Monoisotopic mass	342.11034 Da
Source	ChEBI
InChIKey	SLIMCXCSQXYCGL-JENUQAQBSA-N

SMILES

COc1cc(/C=C/c2cc(/C=C/C(=O)O)cc(OC)c2O)ccc1O

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+

Also called

(2E)-3-{4-hydroxy-3-[(E)-2-(4-hydroxy-3-methoxyphenyl)ethenyl]-5-methoxyphenyl}prop-2-enoic acid (EXACT_SYNONYM)— chebi
3-(3-methoxy-4-hydroxystyryl)-4-hydroxy-5-methoxycinnamic acid (EXACT_SYNONYM)— chebi
8,5'-diferulic acid (decarboxylated form) (EXACT_SYNONYM)— chebi
decarboxylated 8,5'-diferulic acid (EXACT_SYNONYM)— chebi

Activity roles

Every antimicrobial role a source asserts for this compound — the unreduced evidence behind its antimicrobial_class.

CHEBI:35718 CHEBI:35718

Source concepts

Every upstream concept that resolved to this record. The merge is the product: this is what shows ChEBI and CARD are describing the same structure.

Upstream concepts merged into this record
Source	Native ID	Label	Minted CURIE	Version
CHEBI	`CHEBI:156511`	poacic acid	`antibioticmech:chebi-2637266039`	2026-08-30

Curation history

SEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources
Seeded from data/raw/ inventories (CHEBI)
RESEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources
Re-seeded from updated data/raw/ inventories
RESEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources
Re-seeded from updated data/raw/ inventories

Provenance

Seeded by scripts/seed_from_sources.py from the committed inventories in data/raw/. View the record.