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Record Information
Version	2.0
Creation Date	2012-05-31 14:24:56 -0600
Update Date	2015-06-03 17:19:12 -0600
Secondary Accession Numbers	ECMDB20052
Identification
Name:	2-Succinylbenzoyl-CoA
Description	2-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	MOLSDFPDBSMILESInChI × Structure for #<Compound:0x9fd6d748> Close
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.
Kingdom	Organic compounds
Super Class	Lipids and lipid-like molecules
Class	Fatty Acyls
Sub Class	Fatty acyl thioesters
Direct Parent	Acyl CoAs
Alternative Parents	Coenzyme A and derivatives Purine ribonucleoside diphosphates Pentose phosphates Ribonucleoside 3'-phosphates Alkyl-phenylketones Beta amino acids and derivatives Butyrophenones Glycosylamines Organic pyrophosphates 6-aminopurines Monosaccharide phosphates Benzoic acids and derivatives Thiobenzoic acids and derivatives Aryl alkyl ketones Benzoyl derivatives Gamma-keto acids and derivatives Aminopyrimidines and derivatives Monoalkyl phosphates N-substituted imidazoles N-acyl amines Imidolactams Heteroaromatic compounds Tetrahydrofurans Amino acids Secondary carboxylic acid amides Secondary alcohols Carbothioic S-esters Thioesters Carboxylic acids Oxacyclic compounds Azacyclic compounds Sulfenyl compounds Monocarboxylic acids and derivatives Organic oxides Organopnictogen compounds Primary amines Hydrocarbon derivatives
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 Framework	Aromatic heteropolycyclic compounds
External Descriptors	benzoyl-CoAs (CHEBI:15509 )
Physical Properties
State:	Not Available
Charge:	-5
Melting point:	Not Available
Experimental Properties:	Property Value Source
Predicted Properties	Property Value Source Water Solubility 2.66 g/L ALOGPS logP 0.11 ALOGPS logP -4.4 ChemAxon logS -2.6 ALOGPS pKa (Strongest Acidic) 0.82 ChemAxon pKa (Strongest Basic) 4.14 ChemAxon Physiological Charge -5 ChemAxon Hydrogen Acceptor Count 20 ChemAxon Hydrogen Donor Count 10 ChemAxon Polar Surface Area 418 Ų ChemAxon Rotatable Bond Count 25 ChemAxon Refractivity 214.17 m³·mol⁻¹ ChemAxon Polarizability 88.03 ų ChemAxon Number of Rings 4 ChemAxon Bioavailability 0 ChemAxon Rule of Five Yes ChemAxon Ghose Filter Yes ChemAxon Veber's Rule Yes ChemAxon MDDR-like Rule Yes ChemAxon
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 biosythesis PW001897
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 Type Description Splash Key Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Positive splash10-0f80-1955100105-c17079f02635ae8699c1 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-000i-0962200000-22d528673c0203f6dc73 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-0019-2932000000-c5a2fc977f0ae220f612 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-1030-3950232707-107bc76f4cf9a088f447 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-003r-3901201001-d0578f5526758915d7d8 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-057i-6900100000-a7e8ae773d5d9f7c5bd5 View in MoNA 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View 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
Links
External Links:	Resource Link CHEBI ID 15509 HMDB ID Not Available Pubchem Compound ID 126279 Kegg ID C03160 ChemSpider ID 10128120 Wikipedia ID Not Available BioCyc ID CPD-6972 EcoCyc ID CPD-6972

Enzymes