2.02012-07-30 14:55:33 -06002015-06-03 17:21:17 -0600ECMDB21384M2MDB001779StachydrineStachydrine, also known as proline betaine, is an osmoprotectant or osmoprotective compound, which help organisms to survive extreme osmotic stress. This helps bacteria like E. coli survive in harsh host environments such as urine in mammals. (PMID 3316273, Wikipedia) Uptake of osmoprotectants like proline betaine by E. coli is performed by transport systems such as ProP and ProU, which involve periplasmic substrate binding proteins such as ProX. (PMID 7898450)(2S)-1,1-dimethylpyrrolidinium-2-carboxylate(2S)-1,1-dimethylpyrrolidinium-2-carboxylic acid(2S)-2-carboxy-1,1-dimethylpyrrolidinium(S)-2-carboxy-1,1-dimethylpyrrolidinium(S)-2-carboxylato-1,1-dimethylpyrrolidinium<I>N,N</I>-dimethyl prolineHomostachydrineL-Proline betaineN,N-Dimethyl prolineN,N-Dimethyl-L-prolinePrestwick-08G03Proline betaineStachydrineC7H13NO2143.1836143.094628665(2S)-1,1-dimethylpyrrolidin-1-ium-2-carboxylatestachydrine471-87-4C[N+]1(C)CCC[C@H]1C([O-])=OInChI=1S/C7H13NO2/c1-8(2)5-3-4-6(8)7(9)10/h6H,3-5H2,1-2H3/t6-/m0/s1CMUNUTVVOOHQPW-LURJTMIESA-NSolidlogp-2.24logs-2.47solubility6.66e-01 g/llogp-3.9pka_strongest_acidic2.26iupac(2S)-1,1-dimethylpyrrolidin-1-ium-2-carboxylateaverage_mass143.1836mono_mass143.094628665smilesC[N+]1(C)CCC[C@H]1C([O-])=OformulaC7H13NO2inchiInChI=1S/C7H13NO2/c1-8(2)5-3-4-6(8)7(9)10/h6H,3-5H2,1-2H3/t6-/m0/s1inchikeyCMUNUTVVOOHQPW-LURJTMIESA-Npolar_surface_area40.13refractivity60.11polarizability15.05rotatable_bond_count1acceptor_count2donor_count0physiological_charge0formal_charge0Specdb::CMs5965Specdb::CMs148675Specdb::NmrOneD54682Specdb::NmrOneD54683Specdb::NmrOneD54684Specdb::NmrOneD54685Specdb::NmrOneD54686Specdb::NmrOneD54687Specdb::NmrOneD54688Specdb::NmrOneD54689Specdb::NmrOneD54690Specdb::NmrOneD54691Specdb::NmrOneD54692Specdb::NmrOneD54693Specdb::NmrOneD54694Specdb::NmrOneD54695Specdb::NmrOneD54696Specdb::NmrOneD54697Specdb::NmrOneD54698Specdb::NmrOneD54699Specdb::NmrOneD54700Specdb::NmrOneD54701Specdb::MsMs319468Specdb::MsMs319469Specdb::MsMs319470Specdb::MsMs366598Specdb::MsMs366599Specdb::MsMs366600Specdb::MsMs2244477Specdb::MsMs2691659Specdb::MsMs2691660Specdb::MsMs2691661Specdb::MsMs2991107Specdb::MsMs2991108Specdb::MsMs2991109HMDB04827115244103115C1017235280CPD-821Chambers, S. T., Kunin, C. M. (1987). "Osmoprotective activity for Escherichia coli in mammalian renal inner medulla and urine. Correlation of glycine and proline betaines and sorbitol with response to osmotic loads." J Clin Invest 80:1255-1260.3316273Haardt, M., Kempf, B., Faatz, E., Bremer, E. (1995). "The osmoprotectant proline betaine is a major substrate for the binding-protein-dependent transport system ProU of Escherichia coli K-12." Mol Gen Genet 246:783-786.7898450Chambers ST, Kunin CM: Isolation of glycine betaine and proline betaine from human urine. Assessment of their role as osmoprotective agents for bacteria and the kidney. J Clin Invest. 1987 Mar;79(3):731-7.3546377Lever M, Sizeland PC, Bason LM, Hayman CM, Chambers ST: Glycine betaine and proline betaine in human blood and urine. Biochim Biophys Acta. 1994 Aug 18;1200(3):259-64.8068711Le Rudulier D, Bernard T, Goas G, Hamelin J: Osmoregulation in Klebsiella pneumoniae: enhancement of anaerobic growth and nitrogen fixation under stress by proline betaine, gamma-butyrobetaine, and other related compounds. Can J Microbiol. 1984 Mar;30(3):299-305.6372974Atkinson W, Downer P, Lever M, Chambers ST, George PM: Effects of orange juice and proline betaine on glycine betaine and homocysteine in healthy male subjects. Eur J Nutr. 2007 Dec;46(8):446-52. Epub 2007 Dec 4.18060588Proline/betaine transporterP0C0L7PROP_ECOLIproPhttp://ecmdb.ca/proteins/P0C0L7.xml