2.0 2012-05-31 14:24:56 -0600 2015-06-03 17:19:12 -0600 ECMDB20052 M2MDB000901 2-Succinylbenzoyl-CoA 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. 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 <i>o</i>-succinylbenzoyl-CoA Cpo-coa ester O-Succinylbenzoyl-coa OSucB-CoA Succinylbenzoyl-coa C32H44N7O20P3S 971.713 971.157467109 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 o-succinylbenzoyl-coa 72471-59-1 [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 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 AVOVYFCDODUXLY-HSJNEKGZSA-N Cytosol logp 0.11 ALOGPS logs -2.56 ALOGPS solubility 2.66e+00 g/l ALOGPS logp -4.4 ChemAxon pka_strongest_acidic 0.82 ChemAxon pka_strongest_basic 4.14 ChemAxon iupac 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 ChemAxon average_mass 971.713 ChemAxon mono_mass 971.157467109 ChemAxon 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 ChemAxon formula C32H44N7O20P3S ChemAxon 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 ChemAxon inchikey AVOVYFCDODUXLY-HSJNEKGZSA-N ChemAxon polar_surface_area 418 ChemAxon refractivity 214.17 ChemAxon polarizability 88.03 ChemAxon rotatable_bond_count 25 ChemAxon acceptor_count 20 ChemAxon donor_count 10 ChemAxon physiological_charge -5 ChemAxon formal_charge 0 ChemAxon Ubiquinone and other terpenoid-quinone biosynthesis ec00130 Metabolic pathways eco01100 Menaquinol biosythesis Menaquinol biosynthesis starts with chorismate being metabolized into isochorismate through a isochorismate synthase. Isochorismate then interacts with 2-oxoglutare and a hydrogen ion through a 2-succinyl-5-enolpyruvyl-6-hydroxy-3-cyclohexene-1-carboxylate synthase resulting in the release of a carbon dioxide and a 2-succinyl-5-enolpyruvyl-6-hydroxy-3-cyclohexene-1-carboxylate. The latter compound then interacts with (1R,6R)-2-succinyl-6-hydroxy-2,4-cyclohexadiene-1-carboxylate synthase resulting in the release of a pyruvate and a (1R,6R)-6-hydroxy-2-succinylcyclohexa-2,4-diene-1-carboxylate. This compound is the dehydrated through a o-succinylbenzoate synthase resulting in the release of a water molecule and a 2-succinylbenzoate. This compound then interacts with a coenzyme A and an ATP through a o-succinylbenzoate CoA ligase resulting in the release of a diphosphate, a AMP and a succinylbenzoyl-CoA. The latter compound interacts with a hydrogen ion through a 1,4-dihydroxy-2-naphthoyl-CoA synthase resulting in the release of a water molecule or a 1,4-dihydroxy-2-naphthoyl-CoA. This compound then interacts with water through a 1,4-dihydroxy-2-naphthoyl-CoA thioesterase resulting in the release of a coenzyme A, a hydrogen ion and a 1,4-dihydroxy-2-naphthoate. The 1,4-dihydroxy-2-naphthoate can interact with either farnesylfarnesylgeranyl-PP or octaprenyl diphosphate and a hydrogen ion through a 1,4-dihydroxy-2-naphthoate octaprenyltransferase resulting in a release of a carbon dioxide, a pyrophosphate and a demethylmenaquinol-8. This compound then interacts with SAM through a bifunctional 2-octaprenyl-6-methoxy-1,4-benzoquinone methylase and S-adenosylmethionine:2-DMK methyltransferase resulting in a hydrogen ion, a s-adenosyl-L-homocysteine and a menaquinol. PW001897 Metabolic 1,4-dihydroxy-2-naphthoate biosynthesis I PWY-5837 Specdb::NmrOneD 323312 Specdb::NmrOneD 323313 Specdb::NmrOneD 323314 Specdb::NmrOneD 323315 Specdb::NmrOneD 323316 Specdb::NmrOneD 323317 Specdb::NmrOneD 323318 Specdb::NmrOneD 323319 Specdb::NmrOneD 323320 Specdb::NmrOneD 323321 Specdb::NmrOneD 323322 Specdb::NmrOneD 323323 Specdb::NmrOneD 323324 Specdb::NmrOneD 323325 Specdb::NmrOneD 323326 Specdb::NmrOneD 323327 Specdb::NmrOneD 323328 Specdb::NmrOneD 323329 Specdb::NmrOneD 323330 Specdb::NmrOneD 323331 Specdb::MsMs 28751 Specdb::MsMs 28752 Specdb::MsMs 28753 Specdb::MsMs 35309 Specdb::MsMs 35310 Specdb::MsMs 35311 126279 10128120 C03160 15509 CPD-6972 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. 21097882 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. 22080510 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. 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. 18331064 Naphthoate synthase P0ABU0 MENB_ECOLI menB http://ecmdb.ca/proteins/P0ABU0.xml 2-succinylbenzoate--CoA ligase P37353 MENE_ECOLI menE http://ecmdb.ca/proteins/P37353.xml Adenosine triphosphate + Coenzyme A + 2-Succinylbenzoate <> Adenosine monophosphate + Pyrophosphate + 2-Succinylbenzoyl-CoA R04030 O-SUCCINYLBENZOATE-COA-LIG-RXN Hydrogen ion + 2-Succinylbenzoyl-CoA > 1,4-Dihydroxy-2-naphthoyl-CoA + Water R07263 NAPHTHOATE-SYN-RXN 2-Succinylbenzoyl-CoA <> 1,4-Dihydroxy-2-naphthoyl-CoA + Water R07263 NAPHTHOATE-SYN-RXN Adenosine triphosphate + 2-Succinylbenzoate + Coenzyme A > Adenosine monophosphate + Pyrophosphate + 2-Succinylbenzoyl-CoA R04030 O-SUCCINYLBENZOATE-COA-LIG-RXN 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 PW_R005221 2-Succinylbenzoyl-CoA + Hydrogen ion > Water + 1,4-dihydroxy-2-naphthoyl-CoA + 1,4-Dihydroxy-2-naphthoyl-CoA PW_R005226