piperonylic acid

CHEBI:107644 ·resolve ·ANTIFUNGAL ·EXACT SEEDED

A member of the class of benzodioxoles that is 1,3-benzodioxole substituted by a carboxy group at position 5. It is a natural product isolated from several plant species. It is a selective mechanism-based inactivator of the trans-cinnamate 4-hydroxylase enzyme and exhibits antifungal and skin wound healing properties. — 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.

Label unavailable CHEBI:25384
Label unavailable CHEBI:33859
Label unavailable CHEBI:38298

Chemical structure

Computed structure properties
Molecular formula	C8H6O4
Charge	0
Average mass	166.132 Da
Monoisotopic mass	166.02661 Da
Source	ChEBI
InChIKey	VDVJGIYXDVPQLP-UHFFFAOYSA-N

SMILES

O=C(O)c1ccc2c(c1)OCO2

InChI

InChI=1S/C8H6O4/c9-8(10)5-1-2-6-7(3-5)12-4-11-6/h1-3H,4H2,(H,9,10)

Also called

1,3-benzodioxole-5-carboxylic acid (EXACT_SYNONYM)— chebi
1,3-dioxaindane-5-carboxylic acid (EXACT_SYNONYM)— chebi
2H-1,3-benzodioxole-5-carboxylic acid (EXACT_SYNONYM)— chebi
3,4-(methylenedioxy)benzoic acid (EXACT_SYNONYM)— chebi
3,4-dioxymethylenebenzoic acid (EXACT_SYNONYM)— chebi
3,4-methylenedioxybenzoic acid (EXACT_SYNONYM)— chebi
5-benzodioxolecarboxylic acid (EXACT_SYNONYM)— chebi
benzo[d][1,3]dioxole-5-carboxylic acid (EXACT_SYNONYM)— chebi
heliotropic acid (EXACT_SYNONYM)— chebi
protocatechuic acid methylene ether (EXACT_SYNONYM)— chebi

Cross-references

Identifiers for this same structure in other resources. An accession that lands on two different structures in this corpus is withheld from both rather than shown here, since it names at most one of them.

Activity roles

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

antifungal agent 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:107644`	piperonylic acid	`antibioticmech:chebi-9c7c4760a7`	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 (YAML).

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