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.
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
Equivalent identifiers for this same structure in other resources.
- cas:94-53-1
- chemspider:6928
- hmdb:HMDB0032613
- knapsack:C00031034
- lincs.smallmolecule:LSM-19007
- pdb-ccd:0HN
- reaxys:150206
Activity roles
Every antimicrobial role a source asserts for this compound — the
unreduced evidence behind its antimicrobial_class.
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.