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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2006-08-24 14:41:17 UTC
Update Date2019-07-23 05:46:19 UTC
HMDB IDHMDB0004827
Secondary Accession Numbers
  • HMDB04827
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 ). Proline betaine is a biomarker for the consumption of citrus fruits.
Structure
Data?1563860779
Synonyms
ValueSource
(S)-2-Carboxylato-1,1-dimethylpyrrolidiniumChEBI
N,N-Dimethyl-L-prolineChEBI
Proline betaineChEBI
StachydrineChEBI
DimethylprolineMeSH
Stachydrine chloride, (S)-isomerMeSH
Stachydrine chlorideMeSH
Stachydrine, (+-)-isomerMeSH
(2S)-2-Carboxy-1,1-dimethylpyrrolidiniumHMDB
(S)-2-Carboxy-1,1-dimethylpyrrolidiniumHMDB
HomostachydrineHMDB
L-Proline betaineHMDB, KEGG
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 KeyCMUNUTVVOOHQPW-LURJTMIESA-N
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.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentProline and derivatives
Alternative Parents
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 FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Role

Industrial application:

Biological role:

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 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity60.11 m³·mol⁻¹ChemAxon
Polarizability15.05 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-002e-9000000000-36bbb91342358293711aJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0900000000-ea4782d2282bc28329c0JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0007-4900000000-75a3b0df6adc0100b9feJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0aou-9000000000-5df24b6079668b584f79JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0900000000-34921bec4b2fad07f505JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-3900000000-da3a14fcb5a4909b775eJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000f-9000000000-7b04a861eee46ac86b66JSpectraViewer | MoNA
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Feces
  • Saliva
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified10.0 (0.0-50.00) uMAdult (>18 years old)BothNormal details
BloodDetected but not Quantified Adult (>18 years old)Both
Normal
details
BloodDetected but not Quantified Adult (>18 years old)Both
Normal
details
BloodDetected but not Quantified Adult (>18 years old)Female
Normal
details
BloodDetected but not Quantified Adult (>18 years old)Female
Normal
details
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Not SpecifiedNormal details
UrineDetected and Quantified2.3 (0.8-4.0) umol/mmol creatinineAdult (>18 years old)Both
Normal
details
UrineDetected but not Quantified Adult (>18 years old)Both
Normal
details
UrineDetected but not Quantified Adult (>18 years old)Both
Normal
details
UrineDetected but not Quantified Adult (>18 years old)Both
Normal
details
UrineDetected but not Quantified Adult (>18 years old)Both
Normal
details
UrineDetected but not Quantified Adult (>18 years old)Male
Normal
details
UrineDetected but not Quantified Adult (>18 years old)Both
Normal
details
UrineDetected but not Quantified Adult (>18 years old)Both
Normal
details
UrineDetected and Quantified12.7 (1.645-23.7) umol/mmol creatinineAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not Quantified Adult (>18 years old)Both
Colorectal adenoma
details
BloodDetected but not Quantified Adult (>18 years old)Both
Colorectal adenoma
details
FecesDetected but not Quantified Adult (>18 years old)BothColorectal Cancer details
FecesDetected but not Quantified Adult (>18 years old)Both
Colorectal cancer
details
FecesDetected but not Quantified Adult (>18 years old)Both
Colorectal cancer
details
UrineDetected but not Quantified Adult (>18 years old)Both
Colorectal adenoma
details
UrineDetected but not Quantified Adult (>18 years old)Both
Colorectal adenoma
details
Associated Disorders and Diseases
Disease References
Colorectal cancer
  1. Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ]
  2. Sinha R, Ahn J, Sampson JN, Shi J, Yu G, Xiong X, Hayes RB, Goedert JJ: Fecal Microbiota, Fecal Metabolome, and Colorectal Cancer Interrelations. PLoS One. 2016 Mar 25;11(3):e0152126. doi: 10.1371/journal.pone.0152126. eCollection 2016. [PubMed:27015276 ]
  3. Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
Associated OMIM IDs
DrugBank IDDB04284
Phenol Explorer Compound IDNot Available
FoodDB IDFDB000463
KNApSAcK IDC00002074
Chemspider ID103115
KEGG Compound IDC10172
BioCyc IDCPD-821
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID7089
PubChem Compound115244
PDB IDNot Available
ChEBI ID35280
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. 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 ]
  2. 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 ]
  3. 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 ]
  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. [PubMed:18060588 ]