piperonylic acid (CHEBI:107644)

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ChEBI Name	piperonylic acid

ChEBI ID	CHEBI:107644

Definition	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.

Stars	This entity has been manually annotated by the ChEBI Team.

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Formula

C8H6O4

Net Charge

Average Mass

166.132

Monoisotopic Mass

166.02661

InChI

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

InChIKey

VDVJGIYXDVPQLP-UHFFFAOYSA-N

SMILES

OC(=O)C1=CC2=C(OCO2)C=C1

Metabolite of Species	Details
Piper philippinum (IPNI:682741-1)	Found in stem (BTO:0001300). See: PubMed
Pseudolarix amabilis (NCBI:txid3355)	Found in bark (BTO:0001301). Isolated from root bark. See: PubMed
Begonia nantoensis (NCBI:txid78253)	Found in rhizome (BTO:0001181). See: DOI

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):	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. EC 1.14.14.91 ( trans-cinnamate 4-monooxygenase) inhibitor Any EC 1.14.14.* (oxidoreductase acting on paired donors, incorporating of 1 atom of oxygen, with reduced flavin or flavoprotein as one donor) inhibitor that interferes with the action of trans-cinnamate 4-monooxygenase (EC 1.14.14.91).

Application(s):	vulnerary A drug used in treating and healing of wounds.

ChEBI Ontology
Outgoing	piperonylic acid (CHEBI:107644) has role antifungal agent (CHEBI:35718) piperonylic acid (CHEBI:107644) has role EC 1.14.14.91 ( trans-cinnamate 4-monooxygenase) inhibitor (CHEBI:184380) piperonylic acid (CHEBI:107644) has role plant metabolite (CHEBI:76924) piperonylic acid (CHEBI:107644) has role vulnerary (CHEBI:73336) piperonylic acid (CHEBI:107644) is a aromatic carboxylic acid (CHEBI:33859) piperonylic acid (CHEBI:107644) is a benzodioxoles (CHEBI:38298) piperonylic acid (CHEBI:107644) is a monocarboxylic acid (CHEBI:25384) piperonylic acid (CHEBI:107644) is conjugate acid of piperonylate (CHEBI:180537)

Incoming	piperonylate (CHEBI:180537) is conjugate base of piperonylic acid (CHEBI:107644)

IUPAC Name

1,3-benzodioxole-5-carboxylic acid

Synonyms	Sources
1,3-dioxaindane-5-carboxylic acid	ChEBI
2H-1,3-benzodioxole-5-carboxylic acid	ChEBI
3,4-(methylenedioxy)benzoic acid	ChEBI
3,4-dioxymethylenebenzoic acid	ChemIDplus
3,4-methylenedioxybenzoic acid	HMDB
5-benzodioxolecarboxylic acid	ChemIDplus
benzo[d][1,3]dioxole-5-carboxylic acid	ChEBI
heliotropic acid	ChemIDplus
protocatechuic acid methylene ether	ChemIDplus

Last Modified

24 November 2021