2.02012-07-30 14:55:21 -06002015-06-03 17:21:11 -0600ECMDB21336M2MDB001736gamma-Butyrobetaine4-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-ammonium4-(N-Trimethylamino)butyrate4-(N-Trimethylamino)butyric acid4-(Trimethylammonio)butanoate4-(Trimethylammonio)butanoic acid4-Butyrobetaine4-Trimethylammoniobutanoate4-Trimethylammoniobutanoic acidActinineButyrobetaineDeoxycarnitineg-Butyrobetaing-ButyrobetaineGamma-ButyrobetainGamma-Butyrobetaineγ-Butyrobetainγ-ButyrobetaineC7H15NO2145.1995145.1102787294-(trimethylazaniumyl)butanoatebutyrobetaine407-64-7C[N+](C)(C)CCCC([O-])=OInChI=1S/C7H15NO2/c1-8(2,3)6-4-5-7(9)10/h4-6H2,1-3H3JHPNVNIEXXLNTR-UHFFFAOYSA-NSolidCytosolExtra-organismPeriplasmlogp-3.15logs-2.95solubility2.25e-01 g/llogp-4pka_strongest_acidic4.46iupac4-(trimethylazaniumyl)butanoateaverage_mass145.1995mono_mass145.110278729smilesC[N+](C)(C)CCCC([O-])=OformulaC7H15NO2inchiInChI=1S/C7H15NO2/c1-8(2,3)6-4-5-7(9)10/h4-6H2,1-3H3inchikeyJHPNVNIEXXLNTR-UHFFFAOYSA-Npolar_surface_area40.13refractivity62.28polarizability16.2rotatable_bond_count4acceptor_count2donor_count0physiological_charge0formal_charge0L-carnitine degradation IIn 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)PW002037Metaboliccarnitine degradation ICARNMET-PWYSpecdb::CMs22503Specdb::CMs171549Specdb::NmrOneD8802Specdb::NmrOneD8803Specdb::NmrOneD8804Specdb::NmrOneD8805Specdb::NmrOneD8806Specdb::NmrOneD8807Specdb::NmrOneD8808Specdb::NmrOneD8809Specdb::NmrOneD8810Specdb::NmrOneD8811Specdb::NmrOneD8812Specdb::NmrOneD8813Specdb::NmrOneD8814Specdb::NmrOneD8815Specdb::NmrOneD8816Specdb::NmrOneD8817Specdb::NmrOneD8818Specdb::NmrOneD8819Specdb::NmrOneD8820Specdb::NmrOneD8821Specdb::MsMs316006Specdb::MsMs316007Specdb::MsMs316008Specdb::MsMs362143Specdb::MsMs362144Specdb::MsMs362145Specdb::MsMs445955Specdb::MsMs445956Specdb::MsMs445957Specdb::MsMs445958Specdb::MsMs445959Specdb::MsMs451916Specdb::MsMs2226282Specdb::MsMs2228408Specdb::MsMs2228638Specdb::MsMs2230831Specdb::MsMs2230911Specdb::MsMs2233273Specdb::MsMs2233346Specdb::MsMs2235597Specdb::MsMs2244552Specdb::MsMs2245579Specdb::MsMs2246672Specdb::MsMs2247604Specdb::MsMs2249605HMDB01161725705C0118116244GAMMA-BUTYROBETAINEKeseler, 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-D590.21097882van 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 370:17-25.17765195Winder, 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 80:2939-2948.18331064Canovas, M., Bernal, V., Sevilla, A., Iborra, J. L. (2007). "Salt stress effects on the central and carnitine metabolisms of Escherichia coli." Biotechnol Bioeng 96:722-737.16894634Pierre 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 12.17508264Crotonobetainyl-CoA:carnitine CoA-transferaseP31572CAIB_ECOLIcaiBhttp://ecmdb.ca/proteins/P31572.xmlOuter membrane protein NP77747OMPN_ECOLIompNhttp://ecmdb.ca/proteins/P77747.xmlOuter membrane pore protein EP02932PHOE_ECOLIphoEhttp://ecmdb.ca/proteins/P02932.xmlL-carnitine/gamma-butyrobetaine antiporterP31553CAIT_ECOLIcaiThttp://ecmdb.ca/proteins/P31553.xmlOuter membrane protein FP02931OMPF_ECOLIompFhttp://ecmdb.ca/proteins/P02931.xmlOuter membrane protein CP06996OMPC_ECOLIompChttp://ecmdb.ca/proteins/P06996.xmlgamma-Butyrobetainyl-CoA + Carnitine <> L-Carnitinyl-CoA + gamma-ButyrobetaineRXN0-3601Carnitine + gamma-Butyrobetainyl-CoA > L-Carnitinyl-CoA + gamma-ButyrobetaineRXN0-3601(E)-4-(Trimethylammonio)but-2-enoyl-CoA + L-Carnitine + 4-Trimethylammoniobutanoyl-CoA <> Crotonobetaine + L-Carnitinyl-CoA + gamma-ButyrobetaineR10643 gamma-Butyrobetainyl-CoA + L-Carnitine > D-Carnitinyl-CoA + gamma-ButyrobetainePW_R005953