2.02012-07-30 14:55:18 -06002015-06-03 17:21:09 -0600ECMDB21321M2MDB001723CrotonobetaineCrotonobetaine 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 salt4-(Trimethylammonio)but-2-enoate4-(Trimethylammonio)but-2-enoic acidCroton betaineCrotonate betaineCrotonic acid betaineCrotono-betaineCrotonobetaineCrotonsaurebetainC7H13NO2143.1836143.094628665(2E)-4-(trimethylazaniumyl)but-2-enoatecrotonobetaine927-89-9[H]\C(=C(\[H])C([H])([H])[N+](C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H])C([O-])=OInChI=1S/C7H13NO2/c1-8(2,3)6-4-5-7(9)10/h4-5H,6H2,1-3H3/b5-4+GUYHPGUANSLONG-SNAWJCMRSA-NCytosolPeriplasmlogp-2.81logs-3.35solubility8.69e-02 g/llogp-3.8pka_strongest_acidic4.49iupac(2E)-4-(trimethylazaniumyl)but-2-enoateaverage_mass143.1836mono_mass143.094628665smiles[H]\C(=C(\[H])C([H])([H])[N+](C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H])C([O-])=OformulaC7H13NO2inchiInChI=1S/C7H13NO2/c1-8(2,3)6-4-5-7(9)10/h4-5H,6H2,1-3H3/b5-4+inchikeyGUYHPGUANSLONG-SNAWJCMRSA-Npolar_surface_area40.13refractivity63.22polarizability15.56rotatable_bond_count3acceptor_count2donor_count0physiological_charge0formal_charge0Specdb::NmrOneD283349Specdb::NmrOneD283350Specdb::NmrOneD283351Specdb::NmrOneD283352Specdb::NmrOneD283353Specdb::NmrOneD283354Specdb::NmrOneD283355Specdb::NmrOneD283356Specdb::NmrOneD283357Specdb::NmrOneD283358Specdb::NmrOneD283359Specdb::NmrOneD283360Specdb::NmrOneD283361Specdb::NmrOneD283362Specdb::NmrOneD283363Specdb::NmrOneD283364Specdb::NmrOneD283365Specdb::NmrOneD283366Specdb::NmrOneD283367Specdb::NmrOneD283368Specdb::MsMs1226395Specdb::MsMs1226396Specdb::MsMs1226397Specdb::MsMs1341994Specdb::MsMs1341995Specdb::MsMs134199654621944575319C0411417237CROTONO-BETAINEvan 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 96:722-737.16894634Glycine betaine/L-proline transport ATP-binding protein proVP14175PROV_ECOLIproVhttp://ecmdb.ca/proteins/P14175.xmlCrotonobetainyl-CoA:carnitine CoA-transferaseP31572CAIB_ECOLIcaiBhttp://ecmdb.ca/proteins/P31572.xmlGlycine betaine/L-proline transport system permease protein proWP14176PROW_ECOLIproWhttp://ecmdb.ca/proteins/P14176.xmlProbable crotonobetaine/carnitine-CoA ligaseP31552CAIC_ECOLIcaiChttp://ecmdb.ca/proteins/P31552.xmlGlycine betaine-binding periplasmic proteinP0AFM2PROX_ECOLIproXhttp://ecmdb.ca/proteins/P0AFM2.xmlProline/betaine transporterP0C0L7PROP_ECOLIproPhttp://ecmdb.ca/proteins/P0C0L7.xmlGlycine betaine/L-proline transport system permease protein proWP14176PROW_ECOLIproWhttp://ecmdb.ca/proteins/P14176.xmlAdenosine triphosphate + Water + Crotonobetaine > ADP + Crotonobetaine + Hydrogen ion + PhosphateAdenosine triphosphate + Water + Crotonobetaine > ADP + Crotonobetaine + Hydrogen ion + PhosphateAdenosine triphosphate + Coenzyme A + Crotonobetaine > ADP + Crotonobetainyl-CoA + PhosphateCarnitine + Crotonobetainyl-CoA <> L-Carnitinyl-CoA + Crotonobetaine(E)-4-(Trimethylammonio)but-2-enoyl-CoA + L-Carnitine + 4-Trimethylammoniobutanoyl-CoA <> Crotonobetaine + L-Carnitinyl-CoA + gamma-ButyrobetaineR10643