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CHEBI:155895 - phenguignardic acid

ChEBI IDCHEBI:155895
ChEBI Namephenguignardic acid
Stars
DefinitionA 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.
Last Modified19 June 2020
SubmitterAdnan
DownloadsMolfile
FormulaC18H14O5
Net Charge0
Average Mass310.305
Monoisotopic Mass310.08412
SMILESO=C1O[C@@](Cc2ccccc2)(C(=O)O)O/C1=C\c1ccccc1
InChIInChI=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
InChIKeyOLOMGTHWMBYIQH-RXBGNRNISA-N
Species of MetaboliteComponentSourceComments
Guignardia bidwellii (ncbitaxon:115983) - PubMed (22779915)
Roles Classification
Chemical Role:
Bronsted acid  A molecular entity capable of donating a hydron to an acceptor (Brønsted base).
Biological Role:
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 Relation(s)
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 Relation(s)
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 acidChEBI
Citations