2-Succinylbenzoyl-CoA (ECMDB20052) (M2MDB000901)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes (2)XML
Proteins (115)
Record Information
Version2.0
Creation Date2012-05-31 14:24:56 -0600
Update Date2015-06-03 17:19:12 -0600
Secondary Accession Numbers
  • ECMDB20052
Identification
Name:2-Succinylbenzoyl-CoA
Description2-succinylbenzoyl-CoA is a member of the chemical class known as Coenzyme A and Derivatives. These are derivative of vitamin B5 containing a 4'-phosphopantetheine moiety attached to a diphospho-adenosine.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms:
  • 2-(3'-Carboxypropionyl)benzoyl-CoA
  • 2-succinylbenzoyl-CoA
  • 4-(2'-Carboxyphenyl)-4-oxobutyrate-Coenzyme A
  • 4-(2'-Carboxyphenyl)-4-oxobutyric acid-coenzyme A
  • 4-(2'-Carboxyphenyl)-4-oxobutyryl-CoA
  • 4-(2'-Carboxyphenyl)-4-oxobutyryl-coa ester
  • 4-(2'-Carboxyphenyl)-4-oxobutyryl-coenzyme A ester
  • o-succinylbenzoyl-CoA
  • Cpo-coa ester
  • O-Succinylbenzoyl-coa
  • OSucB-CoA
  • Succinylbenzoyl-coa
Chemical Formula:C32H44N7O20P3S
Weight:Average: 971.713
Monoisotopic: 971.157467109
InChI Key:AVOVYFCDODUXLY-HSJNEKGZSA-N
InChI:InChI=1S/C32H44N7O20P3S/c1-32(2,26(45)29(46)35-10-9-21(41)34-11-12-63-31(47)18-6-4-3-5-17(18)19(40)7-8-22(42)43)14-56-62(53,54)59-61(51,52)55-13-20-25(58-60(48,49)50)24(44)30(57-20)39-16-38-23-27(33)36-15-37-28(23)39/h3-6,15-16,20,24-26,30,44-45H,7-14H2,1-2H3,(H,34,41)(H,35,46)(H,42,43)(H,51,52)(H,53,54)(H2,33,36,37)(H2,48,49,50)/t20-,24-,25-,26+,30-/m1/s1
CAS number:72471-59-1
IUPAC Name:4-(2-{[(2-{3-[(2R)-3-[({[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)methyl]-2-hydroxy-3-methylbutanamido]propanamido}ethyl)sulfanyl]carbonyl}phenyl)-4-oxobutanoic acid
Traditional IUPAC Name:o-succinylbenzoyl-coa
SMILES:[H][C@](O)(C(O)=NCCC(O)=NCCSC(=O)C1=CC=CC=C1C(=O)CCC(O)=O)C(C)(C)COP(O)(=O)OP(O)(=O)OC[C@@]1([H])O[C@@]([H])(N2C=NC3=C(N)N=CN=C23)[C@]([H])(O)[C@]1([H])OP(O)(O)=O
Chemical Taxonomy
Description belongs to the class of organic compounds known as acyl coas. These are organic compounds containing a coenzyme A substructure linked to an acyl chain.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acyl thioesters
Direct ParentAcyl CoAs
Alternative Parents
Substituents
  • Coenzyme a or derivatives
  • Purine ribonucleoside diphosphate
  • Purine ribonucleoside bisphosphate
  • Purine ribonucleoside 3',5'-bisphosphate
  • Ribonucleoside 3'-phosphate
  • Pentose-5-phosphate
  • Pentose phosphate
  • Alkyl-phenylketone
  • Beta amino acid or derivatives
  • Butyrophenone
  • Glycosyl compound
  • N-glycosyl compound
  • 6-aminopurine
  • Pentose monosaccharide
  • Monosaccharide phosphate
  • Organic pyrophosphate
  • Phenylketone
  • Purine
  • Imidazopyrimidine
  • Thiobenzoic acid or derivatives
  • Benzoic acid or derivatives
  • Benzoyl
  • Gamma-keto acid
  • Aryl alkyl ketone
  • Aryl ketone
  • Aminopyrimidine
  • Monoalkyl phosphate
  • Fatty amide
  • Monocyclic benzene moiety
  • Keto acid
  • Monosaccharide
  • N-acyl-amine
  • N-substituted imidazole
  • Organic phosphoric acid derivative
  • Imidolactam
  • Phosphoric acid ester
  • Benzenoid
  • Alkyl phosphate
  • Pyrimidine
  • Azole
  • Imidazole
  • Tetrahydrofuran
  • Heteroaromatic compound
  • Secondary carboxylic acid amide
  • Ketone
  • Secondary alcohol
  • Carboxamide group
  • Amino acid
  • Amino acid or derivatives
  • Thiocarboxylic acid ester
  • Carbothioic s-ester
  • Thiocarboxylic acid or derivatives
  • Monocarboxylic acid or derivatives
  • Sulfenyl compound
  • Azacycle
  • Oxacycle
  • Carboxylic acid derivative
  • Carboxylic acid
  • Organoheterocyclic compound
  • Primary amine
  • Carbonyl group
  • Organic oxide
  • Organopnictogen compound
  • Organic nitrogen compound
  • Organic oxygen compound
  • Alcohol
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Organooxygen compound
  • Organosulfur compound
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Physical Properties
State:Not Available
Charge:-5
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility2.66 g/LALOGPS
logP0.11ALOGPS
logP-4.4ChemAxon
logS-2.6ALOGPS
pKa (Strongest Acidic)0.82ChemAxon
pKa (Strongest Basic)4.14ChemAxon
Physiological Charge-5ChemAxon
Hydrogen Acceptor Count20ChemAxon
Hydrogen Donor Count10ChemAxon
Polar Surface Area418 ŲChemAxon
Rotatable Bond Count25ChemAxon
Refractivity214.17 m³·mol⁻¹ChemAxon
Polarizability88.03 ųChemAxon
Number of Rings4ChemAxon
Bioavailability0ChemAxon
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
Hydrogen ion + 2-Succinylbenzoyl-CoA > 1,4-Dihydroxy-2-naphthoyl-CoA + Water
2-Succinylbenzoyl-CoA <> 1,4-Dihydroxy-2-naphthoyl-CoA + Water
Adenosine triphosphate + 2-Succinylbenzoate + Coenzyme A > Adenosine monophosphate + Pyrophosphate + 2-Succinylbenzoyl-CoA
Adenosine triphosphate + 2-Succinylbenzoate + CoA > Adenosine monophosphate + Pyrophosphate + 2-Succinylbenzoyl-CoA
2-succinylbenzoate + Coenzyme A + Adenosine triphosphate + 2-Succinylbenzoate > 2-Succinylbenzoyl-CoA + Pyrophosphate + Adenosine monophosphate
2-Succinylbenzoyl-CoA + Hydrogen ion > Water + 1,4-dihydroxy-2-naphthoyl-CoA + 1,4-Dihydroxy-2-naphthoyl-CoA
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, Positivesplash10-0f80-1955100105-c17079f02635ae8699c1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0962200000-22d528673c0203f6dc73View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0019-2932000000-c5a2fc977f0ae220f612View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-1030-3950232707-107bc76f4cf9a088f447View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-003r-3901201001-d0578f5526758915d7d8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-057i-6900100000-a7e8ae773d5d9f7c5bd5View in MoNA
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
References
References:
  • 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
  • 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
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI ID15509
HMDB IDNot Available
Pubchem Compound ID126279
Kegg IDC03160
ChemSpider ID10128120
Wikipedia IDNot Available
BioCyc IDCPD-6972
EcoCyc IDCPD-6972

Enzymes

Protein Details
1. Naphthoate synthase
General function:
Involved in catalytic activity
Specific function:
Converts o-succinylbenzoyl-CoA (OSB-CoA) to 1,4- dihydroxy-2-naphthoyl-CoA (DHNA-CoA)
Gene Name:
menB
Uniprot ID:
P0ABU0
Molecular weight:
31633
Reactions
4-(2-carboxyphenyl)-4-oxobutanoyl-CoA = 1,4-dihydroxy-2-naphthoyl-CoA + 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.