2.0 2012-05-31 14:50:38 -0600 2015-06-03 17:20:18 -0600 ECMDB20559 M2MDB001364 gamma-Butyrobetainyl-CoA Gamma-butyrobetainyl-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. When gamma-butyrobetainyl-CoA was used as a cosubstrate (CoA donor), the first reaction is the CoA transfer. (PMID 11551212) E. coli protein CaiB, which is a member of the recently identified type-III coenzyme A (CoA) transferase family and catalyzes the transfer of the CoA moiety between gamma-butyrobetaine-CoA and carnitine forming carnityl-CoA and gamma-butyrobetaine. (PMID 15518548) γ-butyrobetaine-CoA g-Butyrobetaine-CoA g-Butyrobetainyl-CoA Gamma-Butyrobetaine-coa γ-Butyrobetaine-CoA γ-Butyrobetainyl-CoA C28H50N8O17P3S 895.726 895.22274744 [4-({2-[(3-{[4-({[({[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)-4-oxobutyl]trimethylazanium {4-[(2-{[3-({4-[({[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]-4-oxobutyl}trimethylazanium CC(C)(COP(O)(=O)OP(O)(=O)OCC1OC(C(O)C1OP(O)(O)=O)N1C=NC2=C(N)N=CN=C12)C(O)C(O)=NCCC(O)=NCCSC(=O)CCC[N+](C)(C)C InChI=1S/C28H49N8O17P3S/c1-28(2,23(40)26(41)31-9-8-18(37)30-10-12-57-19(38)7-6-11-36(3,4)5)14-50-56(47,48)53-55(45,46)49-13-17-22(52-54(42,43)44)21(39)27(51-17)35-16-34-20-24(29)32-15-33-25(20)35/h15-17,21-23,27,39-40H,6-14H2,1-5H3,(H7-,29,30,31,32,33,37,41,42,43,44,45,46,47,48)/p+1 QAMRRBGWSPTAEJ-UHFFFAOYSA-O Cytosol logp -1.35 ALOGPS logs -2.25 ALOGPS solubility 5.20e+00 g/l ALOGPS logp -7.9 ChemAxon pka_strongest_acidic 0.83 ChemAxon pka_strongest_basic 4.79 ChemAxon iupac [4-({2-[(3-{[4-({[({[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)-4-oxobutyl]trimethylazanium ChemAxon average_mass 895.726 ChemAxon mono_mass 895.22274744 ChemAxon smiles CC(C)(COP(O)(=O)OP(O)(=O)OCC1OC(C(O)C1OP(O)(O)=O)N1C=NC2=C(N)N=CN=C12)C(O)C(O)=NCCC(O)=NCCSC(=O)CCC[N+](C)(C)C ChemAxon formula C28H50N8O17P3S ChemAxon inchi InChI=1S/C28H49N8O17P3S/c1-28(2,23(40)26(41)31-9-8-18(37)30-10-12-57-19(38)7-6-11-36(3,4)5)14-50-56(47,48)53-55(45,46)49-13-17-22(52-54(42,43)44)21(39)27(51-17)35-16-34-20-24(29)32-15-33-25(20)35/h15-17,21-23,27,39-40H,6-14H2,1-5H3,(H7-,29,30,31,32,33,37,41,42,43,44,45,46,47,48)/p+1 ChemAxon inchikey QAMRRBGWSPTAEJ-UHFFFAOYSA-O ChemAxon polar_surface_area 370.61 ChemAxon refractivity 212.05 ChemAxon polarizability 84.92 ChemAxon rotatable_bond_count 24 ChemAxon acceptor_count 19 ChemAxon donor_count 9 ChemAxon physiological_charge -2 ChemAxon formal_charge 1 ChemAxon L-carnitine degradation I In the absence of exogenous electron acceptors like nitrate, nitrite, fumarate, dimethyl sulfoxide or trimethylamine-N-oxide, the addition of L-carnitine stimulates the anaerobic growth of E. coli. During anaerobic growth in the presence of carbon and nitrogen sources, E. coli is able to catalyze the dehydration and reduction of L-carnitine to γ-butyrobetaine via a cyclic pathway of CoA-linked intermediates. The carbon and nitrogen skeleton of carnitine is not assimilated. The carnitine pathway may play more than one role in the cell: generation of an osmoprotectant and generation of an external electron acceptor in anaerobic respiration. (EcoCyc) PW002037 Metabolic carnitine degradation I CARNMET-PWY Specdb::NmrOneD 254768 Specdb::NmrOneD 254769 Specdb::NmrOneD 254770 Specdb::NmrOneD 254771 Specdb::NmrOneD 254772 Specdb::NmrOneD 254773 Specdb::NmrOneD 254774 Specdb::NmrOneD 254775 Specdb::NmrOneD 254776 Specdb::NmrOneD 254777 Specdb::NmrOneD 254778 Specdb::NmrOneD 254779 Specdb::NmrOneD 254780 Specdb::NmrOneD 254781 Specdb::NmrOneD 254782 Specdb::NmrOneD 254783 Specdb::NmrOneD 254784 Specdb::NmrOneD 254785 Specdb::NmrOneD 254786 Specdb::NmrOneD 254787 Specdb::MsMs 1228186 Specdb::MsMs 1228187 Specdb::MsMs 1228188 726 706 GAMMA-BUTYROBETAINYL-COA 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 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 Crotonobetainyl-CoA:carnitine CoA-transferase P31572 CAIB_ECOLI caiB http://ecmdb.ca/proteins/P31572.xml Crotonobetainyl-CoA dehydrogenase P60584 CAIA_ECOLI caiA http://ecmdb.ca/proteins/P60584.xml gamma-Butyrobetainyl-CoA + Carnitine <> L-Carnitinyl-CoA + gamma-Butyrobetaine RXN0-3601 gamma-Butyrobetainyl-CoA + an oxidized electron acceptor <> Crotonobetainyl-CoA + a reduced electron acceptor CROBETREDUCT-RXN Carnitine + gamma-Butyrobetainyl-CoA > L-Carnitinyl-CoA + gamma-Butyrobetaine RXN0-3601 Crotonobetainyl-CoA + reduced electron acceptor > gamma-Butyrobetainyl-CoA + oxidized electron acceptor PW_R005952 gamma-Butyrobetainyl-CoA + L-Carnitine > D-Carnitinyl-CoA + gamma-Butyrobetaine PW_R005953