2.0 2015-06-17 11:15:02 -0600 2015-10-02 02:25:53 -0600 ECMDB23900 M2MDB005774 L-Carnitine L-carnitine is a metabolite in E. coli., it can be metabolized under anaerobic conditions [PMID: 2266491]. In L-carnitine degradation I pathway, it is a substrate for enzyme Carnitine-CoA ligase which catalyzes the chemical reaction L-carnitine + ATP + coenzyme A -> L-carnitinyl-CoA + AMP + diphosphate. Another enzyme gamma-butyrobetainyl-CoA:carnitine CoA transferase catalyzes the reaction L-carnitine + γ-butyrobetainyl-CoA -> L-carnitinyl-CoA + γ-butyrobetaine (EcoCyc compound: CARNITINE). (R)-Carnitine 3-Carboxy-2-hydroxy-N,N,N-trimethyl-1-propanaminium hydroxide, inner salt L-g-Trimethyl-b-hydroxybutyrobetaine L-gamma-Trimethyl-beta-hydroxybutyrobetaine L-γ-Trimethyl-β-hydroxybutyrobetaine Levocarnitine Vitamin BT C7H15NO3 161.1989 161.105193351 (3R)-3-hydroxy-4-(trimethylazaniumyl)butanoate L-carnitine 541-15-1 C[N+](C)(C)C[C@H](O)CC([O-])=O InChI=1S/C7H15NO3/c1-8(2,3)5-6(9)4-7(10)11/h6,9H,4-5H2,1-3H3/t6-/m1/s1 PHIQHXFUZVPYII-ZCFIWIBFSA-N logp -2.90 ALOGPS logs -1.60 ALOGPS solubility 5.33e+00 g/l ALOGPS logp -4.9 ChemAxon pka_strongest_acidic 4.2 ChemAxon pka_strongest_basic -3.6 ChemAxon iupac (3R)-3-hydroxy-4-(trimethylazaniumyl)butanoate ChemAxon average_mass 161.1989 ChemAxon mono_mass 161.105193351 ChemAxon smiles C[N+](C)(C)C[C@H](O)CC([O-])=O ChemAxon formula C7H15NO3 ChemAxon inchi InChI=1S/C7H15NO3/c1-8(2,3)5-6(9)4-7(10)11/h6,9H,4-5H2,1-3H3/t6-/m1/s1 ChemAxon inchikey PHIQHXFUZVPYII-ZCFIWIBFSA-N ChemAxon polar_surface_area 60.36 ChemAxon refractivity 63.49 ChemAxon polarizability 16.93 ChemAxon rotatable_bond_count 4 ChemAxon acceptor_count 3 ChemAxon donor_count 1 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 Specdb::CMs 2967 Specdb::CMs 37274 Specdb::CMs 152885 Specdb::CMs 1049414 Specdb::CMs 1049415 Specdb::CMs 1049417 Specdb::CMs 1049419 Specdb::CMs 1049421 Specdb::CMs 1049423 Specdb::NmrOneD 4924 Specdb::MsMs 301675 Specdb::MsMs 301676 Specdb::MsMs 301677 Specdb::MsMs 344224 Specdb::MsMs 344225 Specdb::MsMs 344226 Specdb::MsMs 445885 Specdb::MsMs 445886 Specdb::MsMs 445887 Specdb::MsMs 445888 Specdb::MsMs 445889 Specdb::MsMs 447344 Specdb::MsMs 448029 Specdb::MsMs 448030 Specdb::MsMs 448139 Specdb::MsMs 2846036 Specdb::MsMs 2846037 Specdb::MsMs 2846038 C00318 Crotonobetainyl-CoA:carnitine CoA-transferase P31572 CAIB_ECOLI caiB http://ecmdb.ca/proteins/P31572.xml Probable crotonobetaine/carnitine-CoA ligase P31552 CAIC_ECOLI caiC http://ecmdb.ca/proteins/P31552.xml (E)-4-(Trimethylammonio)but-2-enoyl-CoA + L-Carnitine + 4-Trimethylammoniobutanoyl-CoA <> Crotonobetaine + L-Carnitinyl-CoA + gamma-Butyrobetaine R10643 Palmityl-CoA + L-Carnitine <> L-Palmitoylcarnitine + Coenzyme A PW_R002466 L-Carnitine + Coenzyme A + Adenosine triphosphate > D-Carnitinyl-CoA + Adenosine monophosphate + Pyrophosphate PW_R005950 gamma-Butyrobetainyl-CoA + L-Carnitine > D-Carnitinyl-CoA + gamma-Butyrobetaine PW_R005953