2.0 2012-05-31 09:56:31 -0600 2015-09-13 12:56:05 -0600 ECMDB00062 M2MDB000023 Carnitine Carnitine is a quaternary ammonium compound biosynthesized from the amino acids lysine and methionine. In living cells, it is required for the transport of fatty acids during the breakdown of lipids (fats) for the generation of metabolic energy. Carnitine was originally found as a growth factor for mealworms and labeled vitamin Bt. Carnitine exists in two stereoisomers: Its biologically active form is L-carnitine, whereas its enantiomer, D-carnitine, is biologically inactive. E. coli converts carnitine, via crotonobetaine, to gamma-butyrobetaine in the presence of C and N sources and under anaerobic conditions. This two-step pathway requires L-(-)-carnitine dehydratase and crotonobetaine reductase. Anaerobic carnitine metabolism in Escherichia coli involves six genes organized in the cai operon and located at the first minute on the E. coli chromosome. γ-Trimethyl-hydroxybutyrobetaine (-)-(R)-3-Hydroxy-4-(trimethylammonio)butyrate (-)-(R)-3-Hydroxy-4-(trimethylammonio)butyric acid (-)-Carnitine (-)-L-Carnitine (3-carboxy-2-hydroxypropyl)trimethyl-Ammonium hydroxide inner salt (R)-(3-Carboxy-2-hydroxypropyl)trimethylammonium hydroxide (R)-Carnitine (S)-carnitine 1-carnitine 3-Carboxy-2-hydroxy-N,N,N-trimethyl-1-propanaminium 3-Carboxy-2-hydroxy-N,N,N-trimethyl-1-Propanaminium hydroxide inner salt 3-Hydroxy-4-trimethylammoniobutanoate 3-Hydroxy-4-trimethylammoniobutanoic acid Bicarnesine Carniking Carniking 50 Carnilean Carnipass Carnipass 20 Carnitene Carnitine (L-form) Carnitor Carnitor, Levocarnitine D-carnitine Delta-carnitine Dl-carnitine g-Trimethyl-ammonium-b-hydroxybutirate g-Trimethyl-ammonium-b-hydroxybutiric acid g-Trimethyl-b-hydroxybutyrobetaine g-Trimethyl-hydroxybutyrobetaine Gamma-trimethyl-ammonium-beta-hydroxybutirate gamma-Trimethyl-ammonium-beta-hydroxybutiric acid Gamma-trimethyl-beta-hydroxybutyrobetaine Gamma-Trimethyl-hydroxybutyrobetaine Karnitin L-γ-trimethyl-β-hydroxybutyrobetaine L-(-)-Carnitine L-Carnitine L-g-Trimethyl-b-hydroxybutyrobetaine L-gamma-Trimethyl-beta-hydroxybutyrobetaine L-γ-Trimethyl-β-hydroxybutyrobetaine Levocarnitina Levocarnitine Levocarnitine chloride Levocarnitinum R-(-)-3-Hydroxy-4-trimethylaminobutyrate R-(-)-3-Hydroxy-4-trimethylaminobutyric acid Vitamin B T Vitamin Bt γ-Trimethyl-ammonium-β-hydroxybutirate γ-Trimethyl-ammonium-β-hydroxybutiric acid γ-Trimethyl-hydroxybutyrobetaine γ-Trimethyl-β-hydroxybutyrobetaine δ-Carnitine C7H16NO3 162.2068 162.113018383 (3-carboxy-2-hydroxypropyl)trimethylazanium carnitina 541-15-1 C[N+](C)(C)CC(O)CC(O)=O InChI=1S/C7H15NO3/c1-8(2,3)5-6(9)4-7(10)11/h6,9H,4-5H2,1-3H3/p+1 PHIQHXFUZVPYII-UHFFFAOYSA-O Solid Cytosol Extra-organism Periplasm logp -2.75 ALOGPS logs -1.48 ALOGPS solubility 6.58e+00 g/l ALOGPS melting_point 210-212 oC logp -4.9 ChemAxon pka_strongest_acidic 4.2 ChemAxon pka_strongest_basic -3.6 ChemAxon iupac (3-carboxy-2-hydroxypropyl)trimethylazanium ChemAxon average_mass 162.2068 ChemAxon mono_mass 162.113018383 ChemAxon smiles C[N+](C)(C)CC(O)CC(O)=O ChemAxon formula C7H16NO3 ChemAxon inchi InChI=1S/C7H15NO3/c1-8(2,3)5-6(9)4-7(10)11/h6,9H,4-5H2,1-3H3/p+1 ChemAxon inchikey PHIQHXFUZVPYII-UHFFFAOYSA-O ChemAxon polar_surface_area 57.53 ChemAxon refractivity 52.65 ChemAxon polarizability 17.18 ChemAxon rotatable_bond_count 4 ChemAxon acceptor_count 3 ChemAxon donor_count 2 ChemAxon physiological_charge 0 ChemAxon formal_charge 1 ChemAxon Lysine degradation ec00310 ABC transporters ec02010 carnitine degradation I CARNMET-PWY Specdb::CMs 81530 Specdb::NmrOneD 290935 Specdb::NmrOneD 290936 Specdb::NmrOneD 290937 Specdb::NmrOneD 290938 Specdb::NmrOneD 290939 Specdb::NmrOneD 290940 Specdb::NmrOneD 290941 Specdb::NmrOneD 290942 Specdb::NmrOneD 290943 Specdb::NmrOneD 290944 Specdb::NmrOneD 290945 Specdb::NmrOneD 290946 Specdb::NmrOneD 290947 Specdb::NmrOneD 290948 Specdb::NmrOneD 290949 Specdb::NmrOneD 290950 Specdb::NmrOneD 290951 Specdb::NmrOneD 290952 Specdb::NmrOneD 290953 Specdb::NmrOneD 290954 Specdb::MsMs 1007744 Specdb::MsMs 1007745 Specdb::MsMs 1007746 HMDB00062 10917 83 C00487 17126 CARNITINE L-Carnitine 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 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 Ishii, N., Nakahigashi, K., Baba, T., Robert, M., Soga, T., Kanai, A., Hirasawa, T., Naba, M., Hirai, K., Hoque, A., Ho, P. Y., Kakazu, Y., Sugawara, K., Igarashi, S., Harada, S., Masuda, T., Sugiyama, N., Togashi, T., Hasegawa, M., Takai, Y., Yugi, K., Arakawa, K., Iwata, N., Toya, Y., Nakayama, Y., Nishioka, T., Shimizu, K., Mori, H., Tomita, M. (2007). "Multiple high-throughput analyses monitor the response of E. coli to perturbations." Science 316:593-597. 17379776 http://hmdb.ca/system/metabolites/msds/000/000/045/original/HMDB00062.pdf?1358894663 Glycine betaine/L-proline transport ATP-binding protein proV P14175 PROV_ECOLI proV http://ecmdb.ca/proteins/P14175.xml Crotonobetainyl-CoA:carnitine CoA-transferase P31572 CAIB_ECOLI caiB http://ecmdb.ca/proteins/P31572.xml Glycine betaine/L-proline transport system permease protein proW P14176 PROW_ECOLI proW http://ecmdb.ca/proteins/P14176.xml Probable crotonobetaine/carnitine-CoA ligase P31552 CAIC_ECOLI caiC http://ecmdb.ca/proteins/P31552.xml Glycine betaine-binding periplasmic protein P0AFM2 PROX_ECOLI proX http://ecmdb.ca/proteins/P0AFM2.xml Proline/betaine transporter P0C0L7 PROP_ECOLI proP http://ecmdb.ca/proteins/P0C0L7.xml Glycine betaine/L-proline transport system permease protein proW P14176 PROW_ECOLI proW http://ecmdb.ca/proteins/P14176.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 Adenosine triphosphate + Water + Carnitine > ADP + Carnitine + Hydrogen ion + Phosphate Adenosine triphosphate + Water + Carnitine > ADP + Carnitine + Hydrogen ion + Phosphate Adenosine triphosphate + Coenzyme A + Carnitine > ADP + L-Carnitinyl-CoA + Phosphate Adenosine triphosphate + Coenzyme A + Carnitine > ADP + D-Carnitinyl-CoA + Phosphate Carnitine + Crotonobetainyl-CoA <> L-Carnitinyl-CoA + Crotonobetaine gamma-Butyrobetainyl-CoA + Carnitine <> L-Carnitinyl-CoA + gamma-Butyrobetaine RXN0-3601 Coenzyme A + Carnitine + Adenosine triphosphate > L-Carnitinyl-CoA + Adenosine monophosphate + Pyrophosphate LCARNCOALIG-RXN Carnitine + gamma-Butyrobetainyl-CoA > L-Carnitinyl-CoA + gamma-Butyrobetaine RXN0-3601 48 mM Na2HPO4, 22 mM KH2PO4, 10 mM NaCl, 45 mM (NH4)2SO4, supplemented with 1 mM MgSO4, 1 mg/l thiamine·HCl, 5.6 mg/l CaCl2, 8 mg/l FeCl3, 1 mg/l MnCl2·4H2O, 1.7 mg/l ZnCl2, 0.43 mg/l CuCl2·2H2O, 0.6 mg/l CoCl2·2H2O and 0.6 mg/l Na2MoO4·2H2O. 4 g/L Gluco Bioreactor, pH controlled, O2 and CO2 controlled, dilution rate: 0.2/h 3.99 uM 0.0 37 oC BW25113 Stationary Phase, glucose limited 15960 0 Ishii, N., Nakahigashi, K., Baba, T., Robert, M., Soga, T., Kanai, A., Hirasawa, T., Naba, M., Hirai, K., Hoque, A., Ho, P. Y., Kakazu, Y., Sugawara, K., Igarashi, S., Harada, S., Masuda, T., Sugiyama, N., Togashi, T., Hasegawa, M., Takai, Y., Yugi, K., Arakawa, K., Iwata, N., Toya, Y., Nakayama, Y., Nishioka, T., Shimizu, K., Mori, H., Tomita, M. (2007). "Multiple high-throughput analyses monitor the response of E. coli to perturbations." Science 316:593-597. 17379776