CHEBI:16666 - prephenic acid

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ChEBI Name prephenic acid
ChEBI ID CHEBI:16666
Definition An oxo dicarboxylic acid that consists of 4-hydroxycyclohexa-2,5-diene-1-carboxylic acid substituted by a 2-carboxy-2-oxoethyl group at position 1.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:45028, CHEBI:8399, CHEBI:26257
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Formula C10H10O6
Net Charge 0
Average Mass 226.18280
InChI InChI=1S/C10H10O6/c11-6-1-3-10(4-2-6,9(15)16)5-7(12)8(13)14/h1-4,6,11H,5H2,(H,13,14)(H,15,16)
InChIKey FPWMCUPFBRFMLH-UHFFFAOYSA-N
SMILES OC1C=CC(CC(=O)C(O)=O)(C=C1)C(O)=O
Metabolite of Species Details
Escherichia coli (NCBI:562) 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): plant metabolite
Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
Escherichia coli metabolite
Any bacterial metabolite produced during a metabolic reaction in Escherichia coli.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing prephenic acid (CHEBI:16666) has role Escherichia coli metabolite (CHEBI:76971)
prephenic acid (CHEBI:16666) has role plant metabolite (CHEBI:76924)
prephenic acid (CHEBI:16666) is a oxo dicarboxylic acid (CHEBI:36145)
prephenic acid (CHEBI:16666) is conjugate acid of (1s,4s)-prephenate(2−) (CHEBI:29934)
prephenic acid (CHEBI:16666) is conjugate acid of prephenate(2−) (CHEBI:57852)
Incoming (1s,4s)-prephenic acid (CHEBI:84387) is a prephenic acid (CHEBI:16666)
(1s,4s)-prephenate(2−) (CHEBI:29934) is conjugate base of prephenic acid (CHEBI:16666)
prephenate(2−) (CHEBI:57852) is conjugate base of prephenic acid (CHEBI:16666)
Synonyms Sources
1-Carboxy-4-hydroxy-2,5-cyclohexadiene-1-pyruvic acid ChemIDplus
1-carboxy-4-hydroxy-α-oxo-2,5-cyclohexadiene-1-propanoic acid ChemIDplus
Prephenic acid KEGG COMPOUND
PREPHENIC ACID PDBeChem
Database Links Databases
C00019632 KNApSAcK
DB08427 DrugBank
HMDB12283 HMDB
PRE PDBeChem
Prephenic_acid Wikipedia
View more database links
Registry Numbers Types Sources
126-49-8 CAS Registry Number ChemIDplus
2698270 Reaxys Registry Number Reaxys
2698270 Beilstein Registry Number Beilstein
Citations Waiting for Citations Types Sources
1156090 PubMed citation CiteXplore
13363412 PubMed citation CiteXplore
14185725 PubMed citation CiteXplore
155813 PubMed citation CiteXplore
IND44654981 Agricola citation CiteXplore
Last Modified
16 July 2015