2.0 2012-07-30 14:55:18 -0600 2015-06-03 17:21:09 -0600 ECMDB21321 M2MDB001723 Crotonobetaine Crotonobetaine is a member of the chemical class known as Quaternary Ammonium Salts. These are compounds containing positively charged polyatomic ion of the structure NR4+, R being an alkyl group or an aryl groupCrotonobetaine is invovled in Carnitine metabolism, and ABC transporters. Crotonobetaine is involved in carnitine metabolism. Carnitine dehydratase from Escherichia coli O44 K74 is an inducible enzyme detectable in cells grown anaerobically in the presence of L-(-)-carnitine or crotonobetaine. (PMID 8188598). (2E)-4-(trimethylammonio)but-2-enoate (2E)-4-(trimethylammonio)but-2-enoic acid (3-carboxyallyl)trimethylammonium hydroxide, inner salt 4-(Trimethylammonio)but-2-enoate 4-(Trimethylammonio)but-2-enoic acid Croton betaine Crotonate betaine Crotonic acid betaine Crotono-betaine Crotonobetaine Crotonsaurebetain C7H13NO2 143.1836 143.094628665 (2E)-4-(trimethylazaniumyl)but-2-enoate crotonobetaine 927-89-9 [H]\C(=C(\[H])C([H])([H])[N+](C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H])C([O-])=O InChI=1S/C7H13NO2/c1-8(2,3)6-4-5-7(9)10/h4-5H,6H2,1-3H3/b5-4+ GUYHPGUANSLONG-SNAWJCMRSA-N Cytosol Periplasm logp -2.81 ALOGPS logs -3.35 ALOGPS solubility 8.69e-02 g/l ALOGPS logp -3.8 ChemAxon pka_strongest_acidic 4.49 ChemAxon iupac (2E)-4-(trimethylazaniumyl)but-2-enoate ChemAxon average_mass 143.1836 ChemAxon mono_mass 143.094628665 ChemAxon smiles [H]\C(=C(\[H])C([H])([H])[N+](C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H])C([O-])=O ChemAxon formula C7H13NO2 ChemAxon inchi InChI=1S/C7H13NO2/c1-8(2,3)6-4-5-7(9)10/h4-5H,6H2,1-3H3/b5-4+ ChemAxon inchikey GUYHPGUANSLONG-SNAWJCMRSA-N ChemAxon polar_surface_area 40.13 ChemAxon refractivity 63.22 ChemAxon polarizability 15.56 ChemAxon rotatable_bond_count 3 ChemAxon acceptor_count 2 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Specdb::NmrOneD 283349 Specdb::NmrOneD 283350 Specdb::NmrOneD 283351 Specdb::NmrOneD 283352 Specdb::NmrOneD 283353 Specdb::NmrOneD 283354 Specdb::NmrOneD 283355 Specdb::NmrOneD 283356 Specdb::NmrOneD 283357 Specdb::NmrOneD 283358 Specdb::NmrOneD 283359 Specdb::NmrOneD 283360 Specdb::NmrOneD 283361 Specdb::NmrOneD 283362 Specdb::NmrOneD 283363 Specdb::NmrOneD 283364 Specdb::NmrOneD 283365 Specdb::NmrOneD 283366 Specdb::NmrOneD 283367 Specdb::NmrOneD 283368 Specdb::MsMs 1226395 Specdb::MsMs 1226396 Specdb::MsMs 1226397 Specdb::MsMs 1341994 Specdb::MsMs 1341995 Specdb::MsMs 1341996 5462194 4575319 C04114 17237 CROTONO-BETAINE 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 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 Adenosine triphosphate + Water + Crotonobetaine > ADP + Crotonobetaine + Hydrogen ion + Phosphate Adenosine triphosphate + Water + Crotonobetaine > ADP + Crotonobetaine + Hydrogen ion + Phosphate Adenosine triphosphate + Coenzyme A + Crotonobetaine > ADP + Crotonobetainyl-CoA + Phosphate Carnitine + Crotonobetainyl-CoA <> L-Carnitinyl-CoA + Crotonobetaine (E)-4-(Trimethylammonio)but-2-enoyl-CoA + L-Carnitine + 4-Trimethylammoniobutanoyl-CoA <> Crotonobetaine + L-Carnitinyl-CoA + gamma-Butyrobetaine R10643