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2-Succinylbenzoate (M2MDB000900)

Record Information
Version2.0
Creation Date2012-05-31 14:24:53 -0600
Update Date2015-09-17 15:41:52 -0600
Secondary Accession Numbers
  • ECMDB20051
Identification
Name:2-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
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms:
  • 2-(3-Carboxypropanoyl)benzoate
  • 2-(3-Carboxypropanoyl)benzoic acid
  • 2-(3-Carboxypropionyl)benzoate
  • 2-(3-Carboxypropionyl)benzoic acid
  • 2-Carboxy-.gamma.-oxo-Benzenebutanoate
  • 2-Carboxy-.gamma.-oxo-Benzenebutanoic acid
  • 2-Carboxy-g-oxo-benzenebutanoate
  • 2-Carboxy-g-oxo-benzenebutanoic acid
  • 2-Carboxy-gamma-oxo-Benzenebutanoate
  • 2-Carboxy-gamma-oxo-Benzenebutanoic acid
  • 2-Carboxy-γ-oxo-benzenebutanoate
  • 2-Carboxy-γ-oxo-benzenebutanoic acid
  • 2-Succinyl-benzoate
  • 2-Succinyl-benzoic acid
  • 2-Succinylbenzoate
  • 2-Succinylbenzoic acid
  • 4-(2'-Carboxyphenyl)-4-oxobutyrate
  • 4-(2'-Carboxyphenyl)-4-oxobutyric acid
  • 4-(2-Carboxyphenyl)-4-oxobutanoate
  • 4-(2-Carboxyphenyl)-4-oxobutanoic acid
  • o-succinyl-benzoate
  • o-succinylbenzoate
  • NChemBio.2007.11-comp4
  • O-(3-Carboxypropionyl)-Benzoate
  • O-(3-Carboxypropionyl)-Benzoic acid
  • O-Succinyl-benzoate
  • O-Succinyl-benzoic acid
  • O-Succinylbenzoate
  • O-Succinylbenzoic acid
  • OSB
  • OSucBA
  • Succinylbenzoate
  • Succinylbenzoic acid
Chemical Formula:C11H8O5
Weight:Average: 220.181
Monoisotopic: 220.038270517
InChI Key:YIVWQNVQRXFZJB-UHFFFAOYSA-L
InChI: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
CAS number:27415-09-4
IUPAC Name:2-(3-carboxypropanoyl)benzoic acid
Traditional IUPAC Name:O-succinylbenzoate
SMILES:[O-]C(=O)CCC(=O)C1=CC=CC=C1C([O-])=O
Chemical Taxonomy
Description belongs to the class of organic compounds known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbonyl compounds
Direct ParentAlkyl-phenylketones
Alternative Parents
Substituents
  • Alkyl-phenylketone
  • Butyrophenone
  • Benzoic acid or derivatives
  • Benzoic acid
  • Benzoyl
  • Aryl alkyl ketone
  • Gamma-keto acid
  • Dicarboxylic acid or derivatives
  • Monocyclic benzene moiety
  • Keto acid
  • Benzenoid
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organic oxide
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Physical Properties
State:Not Available
Charge:-2
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility0.56 g/LALOGPS
logP0.87ALOGPS
logP1.01ChemAxon
logS-2.6ALOGPS
pKa (Strongest Acidic)3.42ChemAxon
pKa (Strongest Basic)-7.6ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area91.67 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity54.61 m³·mol⁻¹ChemAxon
Polarizability21.23 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
Adenosine triphosphate + Coenzyme A + 2-Succinylbenzoate <> Adenosine monophosphate + Pyrophosphate + 2-Succinylbenzoyl-CoA
(1R,6R)-6-Hydroxy-2-succinylcyclohexa-2,4-diene-1-carboxylate <> Water + 2-Succinylbenzoate
2-Succinylbenzoate + Water <> (1R,6R)-6-Hydroxy-2-succinylcyclohexa-2,4-diene-1-carboxylate
Adenosine triphosphate + 2-Succinylbenzoate + Coenzyme A > Adenosine monophosphate + Pyrophosphate + 2-Succinylbenzoyl-CoA
(1R,6R)-6-Hydroxy-2-succinylcyclohexa-2,4-diene-1-carboxylate > 2-Succinylbenzoate + Water
Adenosine triphosphate + 2-Succinylbenzoate + CoA > Adenosine monophosphate + Pyrophosphate + 2-Succinylbenzoyl-CoA
(1R,6R)-6-hydroxy-2-succinylcyclohexa-2,4-diene-1-carboxylate + (1R,6R)-6-Hydroxy-2-succinylcyclohexa-2,4-diene-1-carboxylate > 2-succinylbenzoate + Water + 2-Succinylbenzoate
2-succinylbenzoate + Coenzyme A + Adenosine triphosphate + 2-Succinylbenzoate > 2-Succinylbenzoyl-CoA + Pyrophosphate + Adenosine monophosphate
SMPDB Pathways:
Menaquinol biosythesisPW001897 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:
  • Metabolic pathways eco01100
  • Ubiquinone and other terpenoid-quinone biosynthesis ec00130
EcoCyc Pathways:
  • 1,4-dihydroxy-2-naphthoate biosynthesis I PWY-5837
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0590000000-852b41c075a2f3673677View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-1930000000-74242e299c1efe8e7cdeView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-053r-3900000000-8a860f760912ebe7688dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0590000000-2029d0b8fdb139223f02View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0kk9-0940000000-25652eda070ac9fee146View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a7i-3910000000-7e5a38de6b3824bb2a46View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0970000000-c01c8dd3daf408904029View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a5i-1910000000-952ab73fd1c5b9cd4d9eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-2900000000-ec509913282ae0721a9aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0920000000-180b7cab9d19657ef54fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0560-2900000000-2823bb6b38cd51325b24View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0059-9700000000-879529211d2d7bab79a5View in MoNA
References
References:
  • Emmons, G. T., Campbell, I. M., Bentley, R. (1985). "Vitamin K (menaquinone) biosynthesis in bacteria: purification and probable structure of an intermediate prior to o-succinylbenzoate." Biochem Biophys Res Commun 131:956-960. Pubmed: 3902015
  • Hagervall, T. G., Jonsson, Y. H., Edmonds, C. G., McCloskey, J. A., Bjork, G. R. (1990). "Chorismic acid, a key metabolite in modification of tRNA." J Bacteriol 172:252-259. Pubmed: 2104604
  • Hutson, K. G., Threlfall, D. R. (1978). "Formation of spirodilactone of 4-(2'-carboxyphenyl)-4,4-dihydroxybutyrate from 2-succinylbenzoate in cell-free extracts of Micrococcus luteus." Biochim Biophys Acta 530:1-8. Pubmed: 99177
  • Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
  • Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
  • Marley, M. G., Meganathan, R., Bentley, R. (1986). "Menaquinone (vitamin K2) biosynthesis in Escherichia coli: synthesis of o-succinylbenzoate does not require the decarboxylase activity of the ketoglutarate dehydrogenase complex." Biochemistry 25:1304-1307. Pubmed: 3516220
  • van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195
  • Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. Pubmed: 18331064
  • Young, I. G. (1975). "Biosynthesis of bacterial menaquinones. Menaquinone mutants of Escherichia coli." Biochemistry 14:399-406. Pubmed: 1091286
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI ID18325
HMDB IDHMDB0304087
Pubchem Compound ID955
Kegg IDC02730
ChemSpider ID930
Wikipedia IDNot Available
BioCyc IDO-SUCCINYLBENZOATE
EcoCyc IDO-SUCCINYLBENZOATE
Ligand ExpoOSB

Enzymes

Protein Details
1. o-succinylbenzoate synthase
General function:
Involved in catalytic activity
Specific function:
Converts SHCHC to OSB
Gene Name:
menC
Uniprot ID:
P29208
Molecular weight:
35476
Reactions
(1R,6R)-6-hydroxy-2-succinylcyclohexa-2,4-diene-1-carboxylate = 2-succinylbenzoate + H(2)O.
Protein Details
2. 2-succinylbenzoate--CoA ligase
General function:
Involved in catalytic activity
Specific function:
Converts 2-succinylbenzoate (OSB) to 2-succinylbenzoyl- CoA (OSB-CoA)
Gene Name:
menE
Uniprot ID:
P37353
Molecular weight:
50184
Reactions
ATP + 2-succinylbenzoate + CoA = AMP + diphosphate + 2-succinylbenzoyl-CoA.