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Record Information
Version	2.0
Creation Date	2012-07-30 14:55:33 -0600
Update Date	2015-06-03 17:21:17 -0600
Secondary Accession Numbers	ECMDB21384
Identification
Name:	Stachydrine
Description	Stachydrine, 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)
Structure	MOLSDFPDBSMILESInChI × Structure for #<Compound:0x87432da8> Close
Synonyms:	(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 N,N-dimethyl proline Homostachydrine L-Proline betaine N,N-Dimethyl proline N,N-Dimethyl-L-proline Prestwick-08G03 Proline betaine Stachydrine
Chemical Formula:	C7H13NO2
Weight:	Average: 143.1836 Monoisotopic: 143.094628665
InChI Key:	CMUNUTVVOOHQPW-LURJTMIESA-N
InChI:	InChI=1S/C7H13NO2/c1-8(2)5-3-4-6(8)7(9)10/h6H,3-5H2,1-2H3/t6-/m0/s1
CAS number:	471-87-4
IUPAC Name:	(2S)-1,1-dimethylpyrrolidin-1-ium-2-carboxylate
Traditional IUPAC Name:	stachydrine
SMILES:	C[N+]1(C)CCC[C@H]1C([O-])=O
Chemical Taxonomy
Description	belongs to the class of organic compounds known as proline and derivatives. Proline and derivatives are compounds containing proline or a derivative thereof resulting from reaction of proline at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.
Kingdom	Organic compounds
Super Class	Organic acids and derivatives
Class	Carboxylic acids and derivatives
Sub Class	Amino acids, peptides, and analogues
Direct Parent	Proline and derivatives
Alternative Parents	L-alpha-amino acids Pyrrolidine carboxylic acids N-alkylpyrrolidines Tetraalkylammonium salts Carboxylic acid salts Monocarboxylic acids and derivatives Carboxylic acids Azacyclic compounds Organopnictogen compounds Organic salts Organic oxides Hydrocarbon derivatives Carbonyl compounds Amines
Substituents	Proline or derivatives Alpha-amino acid L-alpha-amino acid Pyrrolidine carboxylic acid Pyrrolidine carboxylic acid or derivatives N-alkylpyrrolidine Tetraalkylammonium salt Pyrrolidine Quaternary ammonium salt Carboxylic acid salt Carboxylic acid Monocarboxylic acid or derivatives Azacycle Organoheterocyclic compound Organic oxide Organopnictogen compound Organooxygen compound Organonitrogen compound Organic nitrogen compound Organic oxygen compound Hydrocarbon derivative Amine Carbonyl group Organic salt Aliphatic heteromonocyclic compound
Molecular Framework	Aliphatic heteromonocyclic compounds
External Descriptors	amino-acid betaine (CHEBI:35280 ) alkaloid (CHEBI:35280 ) N-methyl-L-alpha-amino acid (CHEBI:35280 ) Pyrrolidine alkaloids (C10172 )
Physical Properties
State:	Solid
Charge:	0
Melting point:	Not Available
Experimental Properties:	Property Value Source
Predicted Properties	Property Value Source Water Solubility 0.67 g/L ALOGPS logP -2.2 ALOGPS logP -3.9 ChemAxon logS -2.5 ALOGPS pKa (Strongest Acidic) 2.26 ChemAxon Physiological Charge 0 ChemAxon Hydrogen Acceptor Count 2 ChemAxon Hydrogen Donor Count 0 ChemAxon Polar Surface Area 40.13 Ų ChemAxon Rotatable Bond Count 1 ChemAxon Refractivity 60.11 m³·mol⁻¹ ChemAxon Polarizability 15.05 ų ChemAxon Number of Rings 1 ChemAxon Bioavailability 1 ChemAxon Rule of Five Yes ChemAxon Ghose Filter Yes ChemAxon Veber's Rule Yes ChemAxon MDDR-like Rule Yes ChemAxon
Biological Properties
Cellular Locations:	Cytoplasm
Reactions:
SMPDB Pathways:	Not Available
KEGG Pathways:	Not Available
EcoCyc Pathways:	Not Available
Concentrations
	Not Available
Spectra
Spectra:	Spectrum Type Description Splash Key Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive splash10-002e-9000000000-36bbb91342358293711a View in MoNA Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive Not Available View in JSpectraViewer LC-MS/MS LC-MS/MS Spectrum - 10V, Negative splash10-0bt9-9200000000-395432f0cf8795dd4cf7 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Positive splash10-0006-0900000000-ea4782d2282bc28329c0 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-0007-4900000000-75a3b0df6adc0100b9fe View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-0aou-9000000000-5df24b6079668b584f79 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-0006-0900000000-34921bec4b2fad07f505 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-0006-3900000000-da3a14fcb5a4909b775e View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-000f-9000000000-7b04a861eee46ac86b66 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Positive splash10-0002-9500000000-135bbe696520934e172e View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-0002-9100000000-6d9ce7552b62c3e5d66c View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-059w-9100000000-1648e60acdd97fc80a9d View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-0006-0900000000-bf6e206b443f53ef90b5 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-0006-0900000000-bf6e206b443f53ef90b5 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-0006-9200000000-94164ee813c486cb0b96 View in MoNA 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer
References
References:	Atkinson 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. Pubmed: 18060588 Chambers 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. Pubmed: 3546377 Chambers, 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. Pubmed: 3316273 Haardt, 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. Pubmed: 7898450 Le 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. Pubmed: 6372974 Lever 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. Pubmed: 8068711
Synthesis Reference:	Not Available
Material Safety Data Sheet (MSDS)	Not Available
Links
External Links:	Resource Link CHEBI ID 35280 HMDB ID HMDB04827 Pubchem Compound ID 115244 Kegg ID C10172 ChemSpider ID 103115 Wikipedia ID Not Available BioCyc ID CPD-821 EcoCyc ID CPD-821

Transporters