2.0 2012-07-30 14:55:21 -0600 2015-06-03 17:21:11 -0600 ECMDB21336 M2MDB001736 gamma-Butyrobetaine 4-Trimethylammoniobutanoic acid is an intermediate in carnitine biosynthesis. It is part of a reaction in which 4-trimethylammoniobutanal is oxidized by the 4-trimethylaminobutyraldehyde dehydrogenase protein to 4-trimethylammoniobutanoic acid. 4-trimethylammoniobutanoic acid is transformed into L-carnitine via the enzyme gamma-butyrobetaine dioxygenase.It is a substrate for Gamma-butyrobetaine dioxygenase, Aldehyde dehydrogenase and 4-trimethylaminobutyraldehyde dehydrogenase. 3-Carboxypropyl-trimethyl-ammonium 4-(N-Trimethylamino)butyrate 4-(N-Trimethylamino)butyric acid 4-(Trimethylammonio)butanoate 4-(Trimethylammonio)butanoic acid 4-Butyrobetaine 4-Trimethylammoniobutanoate 4-Trimethylammoniobutanoic acid Actinine Butyrobetaine Deoxycarnitine g-Butyrobetain g-Butyrobetaine Gamma-Butyrobetain Gamma-Butyrobetaine γ-Butyrobetain γ-Butyrobetaine C7H15NO2 145.1995 145.110278729 4-(trimethylazaniumyl)butanoate butyrobetaine 407-64-7 C[N+](C)(C)CCCC([O-])=O InChI=1S/C7H15NO2/c1-8(2,3)6-4-5-7(9)10/h4-6H2,1-3H3 JHPNVNIEXXLNTR-UHFFFAOYSA-N Solid Cytosol Extra-organism Periplasm logp -3.15 ALOGPS logs -2.95 ALOGPS solubility 2.25e-01 g/l ALOGPS logp -4 ChemAxon pka_strongest_acidic 4.46 ChemAxon iupac 4-(trimethylazaniumyl)butanoate ChemAxon average_mass 145.1995 ChemAxon mono_mass 145.110278729 ChemAxon smiles C[N+](C)(C)CCCC([O-])=O ChemAxon formula C7H15NO2 ChemAxon inchi InChI=1S/C7H15NO2/c1-8(2,3)6-4-5-7(9)10/h4-6H2,1-3H3 ChemAxon inchikey JHPNVNIEXXLNTR-UHFFFAOYSA-N ChemAxon polar_surface_area 40.13 ChemAxon refractivity 62.28 ChemAxon polarizability 16.2 ChemAxon rotatable_bond_count 4 ChemAxon acceptor_count 2 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 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::CMs 22503 Specdb::CMs 171549 Specdb::NmrOneD 8802 Specdb::NmrOneD 8803 Specdb::NmrOneD 8804 Specdb::NmrOneD 8805 Specdb::NmrOneD 8806 Specdb::NmrOneD 8807 Specdb::NmrOneD 8808 Specdb::NmrOneD 8809 Specdb::NmrOneD 8810 Specdb::NmrOneD 8811 Specdb::NmrOneD 8812 Specdb::NmrOneD 8813 Specdb::NmrOneD 8814 Specdb::NmrOneD 8815 Specdb::NmrOneD 8816 Specdb::NmrOneD 8817 Specdb::NmrOneD 8818 Specdb::NmrOneD 8819 Specdb::NmrOneD 8820 Specdb::NmrOneD 8821 Specdb::MsMs 316006 Specdb::MsMs 316007 Specdb::MsMs 316008 Specdb::MsMs 362143 Specdb::MsMs 362144 Specdb::MsMs 362145 Specdb::MsMs 445955 Specdb::MsMs 445956 Specdb::MsMs 445957 Specdb::MsMs 445958 Specdb::MsMs 445959 Specdb::MsMs 451916 Specdb::MsMs 2226282 Specdb::MsMs 2228408 Specdb::MsMs 2228638 Specdb::MsMs 2230831 Specdb::MsMs 2230911 Specdb::MsMs 2233273 Specdb::MsMs 2233346 Specdb::MsMs 2235597 Specdb::MsMs 2244552 Specdb::MsMs 2245579 Specdb::MsMs 2246672 Specdb::MsMs 2247604 Specdb::MsMs 2249605 HMDB01161 725 705 C01181 16244 GAMMA-BUTYROBETAINE 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 Canovas, M., Bernal, V., Sevilla, A., Iborra, J. L. (2007). "Salt stress effects on the central and carnitine metabolisms of Escherichia coli." Biotechnol Bioeng 96:722-737. 16894634 Pierre G, Macdonald A, Gray G, Hendriksz C, Preece MA, Chakrapani A: Prospective treatment in carnitine-acylcarnitine translocase deficiency. J Inherit Metab Dis. 2007 Oct;30(5):815. Epub 2007 May 12. 17508264 Crotonobetainyl-CoA:carnitine CoA-transferase P31572 CAIB_ECOLI caiB http://ecmdb.ca/proteins/P31572.xml Outer membrane protein N P77747 OMPN_ECOLI ompN http://ecmdb.ca/proteins/P77747.xml Outer membrane pore protein E P02932 PHOE_ECOLI phoE http://ecmdb.ca/proteins/P02932.xml L-carnitine/gamma-butyrobetaine antiporter P31553 CAIT_ECOLI caiT http://ecmdb.ca/proteins/P31553.xml Outer membrane protein F P02931 OMPF_ECOLI ompF http://ecmdb.ca/proteins/P02931.xml Outer membrane protein C P06996 OMPC_ECOLI ompC http://ecmdb.ca/proteins/P06996.xml gamma-Butyrobetainyl-CoA + Carnitine <> L-Carnitinyl-CoA + gamma-Butyrobetaine RXN0-3601 Carnitine + gamma-Butyrobetainyl-CoA > L-Carnitinyl-CoA + gamma-Butyrobetaine RXN0-3601 (E)-4-(Trimethylammonio)but-2-enoyl-CoA + L-Carnitine + 4-Trimethylammoniobutanoyl-CoA <> Crotonobetaine + L-Carnitinyl-CoA + gamma-Butyrobetaine R10643 gamma-Butyrobetainyl-CoA + L-Carnitine > D-Carnitinyl-CoA + gamma-Butyrobetaine PW_R005953