Record Information
Version1.0
StatusDetected and Quantified
Creation Date2021-11-17 23:49:20 UTC
Update Date2022-08-31 17:38:19 UTC
Metabolite IDMMDBc0029982
Metabolite Identification
Common Name2-Succinylbenzoate
Description2-succinylbenzoate is a member of the chemical class known as Benzoic Acid and Derivatives. These are organic compounds containing a carboxylic acid substituent attached to a benzene ring. 2-Succinylbenzoate is invovled in the biosynthesis of menaquinone. o-Succinylbenzoate synthase (OSBS) from Escherichia coli, a member of the enolase superfamily, catalyzes an exergonic dehydration reaction in the menaquinone biosynthetic pathway in which 2-succinyl-6-hydroxy-2,4-cyclohexadiene-1-carboxylate (SHCHC) is converted to 4-(2'-carboxyphenyl)-4-oxobutyrate (o-succinylbenzoate or OSB). The first aromatic intermediate in the menaquinone biosynthetic pathway is o-succinylbenzoate (OSB); it is formed from chorismate/isochorismate and 2-ketoglutarate. (PMID 3902015 ) The first aromatic intermediate in the menaquinone biosynthetic pathway is o-succinylbenzoate (OSB); it is formed from chorismate/isochorismate and 2-ketoglutarate. The first aromatic intermediate in the menaquinone biosynthetic pathway is o-succinylbenzoate (OSB); it is formed from chorismate/isochorismate and 2-ketoglutarate. The first aromatic intermediate in the menaquinone biosynthetic pathway is o-succinylbenzoate (OSB); it is formed from chorismate/isochorismate and 2-ketoglutarate. coli strains synthesize an intermediate, "X", which is converted to OSB by extracts of menC+ cells. It was demonstrated that chorismate is the branch point compound leading to menaquinone, and that 2-succinylbenzoic acid and 1,4-dihydroxy-2-naphthoic acid can serve as menaquinoone precursors in E. coli. (PMID 1091286 ) The committed step in menaquinone biosynthesis is the formation of o-succinylbenzoate (OSB). (PMID 3516220 ) The suggestion is made that the spirodilactone is the product of an aberrant reaction involving a compound that is normally an intermediate in the conversion of 2-succinylbenzoate to 1,4-dihydroxy-2-naphthoate. (PMID 99177 ) The presence of shikimic acid in the growth medium restores the ability of an aroD mutant to synthesize cmo5U, while O-succinylbenzoate, which is an early intermediate in the synthesis of menaquinone, does not. (PMID 2104604 )
Structure
Synonyms
ValueSource
O-SuccinatobenzoateChEBI
O-SuccinylbenzoateChEBI
SuccinylbenzoateChEBI
O-Succinatobenzoic acidGenerator
O-Succinylbenzoic acidGenerator
Succinylbenzoic acidGenerator
2-Succinylbenzoic acidGenerator
2-SuccinylbenzoateChEBI
2-Succinatobenzoic acidGenerator
Molecular FormulaC11H8O5
Average Mass220.181
Monoisotopic Mass220.038270517
IUPAC Name2-(3-carboxylatopropanoyl)benzoate
Traditional Name2-succinylbenzoate
CAS Registry Number27415-09-4
SMILES
[O-]C(=O)CCC(=O)C1=CC=CC=C1C([O-])=O
InChI Identifier
InChI=1S/C11H10O5/c12-9(5-6-10(13)14)7-3-1-2-4-8(7)11(15)16/h1-4H,5-6H2,(H,13,14)(H,15,16)/p-2
InChI KeyYIVWQNVQRXFZJB-UHFFFAOYSA-L