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Record Information
Version3.6
Creation Date2006-08-24 14:41:17 UTC
Update Date2016-02-11 01:06:52 UTC
HMDB IDHMDB04827
Secondary Accession NumbersNone
Metabolite Identification
Common NameProline betaine
DescriptionProline betaine is an osmoprotective compound found in urine. It is thought to serve an osmoprotective role for the kidney. Proline betaine is a glycine betaine analogue found in many citrus foods. Elevated levels of proline betaine in human urine are found after the consumption of citrus fruits and juices (PMID: 18060588 ).
Structure
Thumb
Synonyms
ValueSource
(S)-2-carboxylato-1,1-DimethylpyrrolidiniumChEBI
N,N-Dimethyl-L-prolineChEBI
Proline betaineChEBI
StachydrineChEBI
(2S)-1,1-Dimethylpyrrolidin-1-ium-2-carboxylic acidGenerator
(2S)-2-Carboxy-1,1-dimethylpyrrolidiniumHMDB
(S)-2-Carboxy-1,1-dimethylpyrrolidiniumHMDB
HomostachydrineHMDB
L-Proline betaineHMDB
Prestwick-08g03HMDB
Chemical FormulaC7H13NO2
Average Molecular Weight143.1836
Monoisotopic Molecular Weight143.094628665
IUPAC Name(2S)-1,1-dimethylpyrrolidin-1-ium-2-carboxylate
Traditional Namestachydrine
CAS Registry Number471-87-4
SMILES
C[N+]1(C)CCC[C@H]1C([O-])=O
InChI Identifier
InChI=1S/C7H13NO2/c1-8(2)5-3-4-6(8)7(9)10/h6H,3-5H2,1-2H3/t6-/m0/s1
InChI KeyInChIKey=CMUNUTVVOOHQPW-LURJTMIESA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentL-alpha-amino acids
Alternative Parents
Substituents
  • L-alpha-amino acid
  • Pyrrolidine carboxylic acid or derivatives
  • Pyrrolidine carboxylic acid
  • N-alkylpyrrolidine
  • Quaternary ammonium salt
  • Pyrrolidine
  • Carboxylic acid salt
  • Azacycle
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Hydrocarbon derivative
  • Organic salt
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Amine
  • Organic zwitterion
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
Biofunction
  • Osmolyte
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.67 mg/mLALOGPS
logP-2.2ALOGPS
logP-3.9ChemAxon
logS-2.5ALOGPS
pKa (Strongest Acidic)2.26ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area40.13 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity60.11 m3·mol-1ChemAxon
Polarizability15.06 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular LocationsNot Available
Biofluid Locations
  • Blood
  • Saliva
  • Urine
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified10.0 (0.0-50.00) uMAdult (>18 years old)BothNormal details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Not SpecifiedNormal details
UrineDetected and Quantified2.3 (0.8-4.0) umol/mmol creatinineAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified12.7 (1.645-23.7) umol/mmol creatinineAdult (>18 years old)BothNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB000463
KNApSAcK IDC00002074
Chemspider ID103115
KEGG Compound IDC10172
BioCyc IDCPD-821
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB04827
Metagene LinkHMDB04827
METLIN ID7089
PubChem Compound115244
PDB IDNot Available
ChEBI ID35280
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. 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. [3546377 ]
  2. 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. [8068711 ]
  3. 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. [6372974 ]
  4. 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. [18060588 ]