phenguignardic acid (CHEBI:155895)

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ChEBI Name	phenguignardic acid

ChEBI ID	CHEBI:155895

Definition	A member of the class of dioxolanes that is 1,3-dioxolane substituted by a carboxy, benzyl and benzylidene groups at positions 2, 2 and 4, respectively. It is a phytotoxic metabolite of the grape black rot fungus Guignardia bidwellii.

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

Supplier Information

Download	Molfile XML SDF

Formula

C18H14O5

Net Charge

Average Mass

310.305

Monoisotopic Mass

310.08412

InChI

InChI=1S/C18H14O5/c19-16-15(11-13-7-3-1-4-8-13)22-18(23-16,17(20)21)12-14-9-5-2-6-10-14/h1-11H,12H2,(H,20,21)/b15-11-/t18-/m0/s1

InChIKey

OLOMGTHWMBYIQH-RXBGNRNISA-N

SMILES

C/1(=C\C2=CC=CC=C2)\O[C@@](CC3=CC=CC=C3)(OC1=O)C(=O)O

Metabolite of Species	Details
Guignardia bidwellii (NCBI:txid115983)	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):	fungal metabolite Any eukaryotic metabolite produced during a metabolic reaction in fungi, the kingdom that includes microorganisms such as the yeasts and moulds.

ChEBI Ontology
Outgoing	phenguignardic acid (CHEBI:155895) has role fungal metabolite (CHEBI:76946) phenguignardic acid (CHEBI:155895) is a benzenes (CHEBI:22712) phenguignardic acid (CHEBI:155895) is a dioxolane (CHEBI:39430) phenguignardic acid (CHEBI:155895) is a monocarboxylic acid (CHEBI:25384) phenguignardic acid (CHEBI:155895) is conjugate acid of phenguignardate (CHEBI:149629)

Incoming	phenguignardate (CHEBI:149629) is conjugate base of phenguignardic acid (CHEBI:155895)

IUPAC Name

(2S,4Z)-2-benzyl-4-benzylidene-5-oxo-1,3-dioxolane-2-carboxylic acid

Synonym	Source
(+)-phenguignardic acid	ChEBI

Last Modified

19 June 2020

General Comment
2020-06-19	Relevant article: Stoye, A., Kowalczyk, D. and Opatz, T. (2013) Total synthesis of (+)-phenguignardic acid, a phytotoxic metabolite of Guignardia bidwellii. Eur. J. Org. Chem., 5952-5960.