2.0 2012-05-31 14:31:51 -0600 2015-06-03 17:19:28 -0600 ECMDB20182 M2MDB001028 Oxalyl-CoA Oxalyl-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. Oxalyl CoA is invovled in the catabolism of toxic compound oxalate. Oxalyl coenzyme A (CoA) decarboxylase (Oxc) is a key enzyme in the catabolism of the highly toxic compound oxalate, catalyzing the decarboxylation of oxalyl-CoA to formyl-CoA. (PMID 15345383) Oxalyl-coenzyme A decarboxylase is a thiamin diphosphate dependent enzyme active in the catabolism of the highly toxic compound oxalate. (PMID 16198641) CoA-oxalate CoA-oxalic acid Oxalyl-coenzyme a C23H36N7O19P3S 839.554 839.099952231 2-({2-[(3-{[(2R)-4-({[({[(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)-1,2-dihydroxy-3,3-dimethylbutylidene]amino}-1-hydroxypropylidene)amino]ethyl}sulfanyl)-2-oxoacetic acid ({2-[(3-{[(2R)-4-[({[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxy]-1,2-dihydroxy-3,3-dimethylbutylidene]amino}-1-hydroxypropylidene)amino]ethyl}sulfanyl)(oxo)acetic acid [H][C@](O)(C(O)=NCCC(O)=NCCSC(=O)C(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/C23H36N7O19P3S/c1-23(2,16(33)19(34)26-4-3-12(31)25-5-6-53-22(37)21(35)36)8-46-52(43,44)49-51(41,42)45-7-11-15(48-50(38,39)40)14(32)20(47-11)30-10-29-13-17(24)27-9-28-18(13)30/h9-11,14-16,20,32-33H,3-8H2,1-2H3,(H,25,31)(H,26,34)(H,35,36)(H,41,42)(H,43,44)(H2,24,27,28)(H2,38,39,40)/t11-,14-,15-,16+,20-/m1/s1 QVXMZFTWJVBUHP-IBOSZNHHSA-N Cytosol logp -0.42 ALOGPS logs -2.18 ALOGPS solubility 5.54e+00 g/l ALOGPS logp -4.1 ChemAxon pka_strongest_acidic 0.81 ChemAxon pka_strongest_basic 4.8 ChemAxon iupac 2-({2-[(3-{[(2R)-4-({[({[(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)-1,2-dihydroxy-3,3-dimethylbutylidene]amino}-1-hydroxypropylidene)amino]ethyl}sulfanyl)-2-oxoacetic acid ChemAxon average_mass 839.554 ChemAxon mono_mass 839.099952231 ChemAxon smiles [H][C@](O)(C(O)=NCCC(O)=NCCSC(=O)C(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 C23H36N7O19P3S ChemAxon inchi InChI=1S/C23H36N7O19P3S/c1-23(2,16(33)19(34)26-4-3-12(31)25-5-6-53-22(37)21(35)36)8-46-52(43,44)49-51(41,42)45-7-11-15(48-50(38,39)40)14(32)20(47-11)30-10-29-13-17(24)27-9-28-18(13)30/h9-11,14-16,20,32-33H,3-8H2,1-2H3,(H,25,31)(H,26,34)(H,35,36)(H,41,42)(H,43,44)(H2,24,27,28)(H2,38,39,40)/t11-,14-,15-,16+,20-/m1/s1 ChemAxon inchikey QVXMZFTWJVBUHP-IBOSZNHHSA-N ChemAxon polar_surface_area 407.91 ChemAxon refractivity 175.05 ChemAxon polarizability 72.11 ChemAxon rotatable_bond_count 21 ChemAxon acceptor_count 21 ChemAxon donor_count 10 ChemAxon physiological_charge -4 ChemAxon formal_charge 0 ChemAxon Glyoxylate and dicarboxylate metabolism ec00630 Metabolic pathways eco01100 Specdb::EiMs 2854 Specdb::MsMs 26246 Specdb::MsMs 26247 Specdb::MsMs 26248 Specdb::MsMs 32804 Specdb::MsMs 32805 Specdb::MsMs 32806 439206 388346 C00313 15535 OXALYL-COA OXK 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 Federici, F., Vitali, B., Gotti, R., Pasca, M. R., Gobbi, S., Peck, A. B., Brigidi, P. (2004). "Characterization and heterologous expression of the oxalyl coenzyme A decarboxylase gene from Bifidobacterium lactis." Appl Environ Microbiol 70:5066-5073. 15345383 Berthold, C. L., Sidhu, H., Ricagno, S., Richards, N. G., Lindqvist, Y. (2006). "Detection and characterization of merohedral twinning in crystals of oxalyl-coenzyme A decarboxylase from Oxalobacter formigenes." Biochim Biophys Acta 1764:122-128. 16198641 Probable oxalyl-CoA decarboxylase P0AFI0 OXC_ECOLI oxc http://ecmdb.ca/proteins/P0AFI0.xml Formyl-coenzyme A transferase P69902 FCTA_ECOLI frc http://ecmdb.ca/proteins/P69902.xml Hydrogen ion + Oxalyl-CoA <> Carbon dioxide + Formyl-CoA R01908 OXALYL-COA-DECARBOXYLASE-RXN Formyl-CoA + Oxalic acid <> Formic acid + Oxalyl-CoA RXN0-1382 Oxalyl-CoA <> Formyl-CoA + Carbon dioxide R01908 Hydrogen ion + Oxalyl-CoA Carbon dioxide + Formyl-CoA R01908 OXALYL-COA-DECARBOXYLASE-RXN Formyl-CoA + Oxalic acid Formic acid + Oxalyl-CoA RXN0-1382 Formyl-CoA + Oxalic acid > Formic acid + Oxalyl-CoA Oxalyl-CoA > Formyl-CoA + Carbon dioxide Acetyl-CoA + Oxalic acid <> Acetic acid + Oxalyl-CoA R10614