Record Information
Version1.0
Creation date2010-04-08 22:04:34 UTC
Update date2019-11-26 02:54:51 UTC
Primary IDFDB000463
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameL-Stachydrine
DescriptionProline betaine, also known as stachydrine, 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. Proline betaine exists in all living organisms, ranging from bacteria to humans. Proline betaine is found, on average, in the highest concentration within capers (Capparis spinosa). Proline betaine has also been detected, but not quantified in, several different foods, such as flour, fruit juice, chickens (Gallus gallus), quinoas (Chenopodium quinoa), and common wheats (Triticum aestivum). This could make proline betaine a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on Proline betaine.
CAS Number471-87-4
Structure
Thumb
Synonyms
SynonymSource
(S)-2-Carboxylato-1,1-dimethylpyrrolidiniumChEBI
N,N-Dimethyl-L-prolineChEBI
StachydrineChEBI
L-Proline betaineKegg
(2S)-2-Carboxy-1,1-dimethylpyrrolidiniumHMDB
(S)-2-Carboxy-1,1-dimethylpyrrolidiniumHMDB
HomostachydrineHMDB
Prestwick-08g03HMDB
DimethylprolineMeSH, HMDB
Stachydrine chlorideMeSH, HMDB
Stachydrine chloride, (S)-isomerMeSH, HMDB
Stachydrine, (+-)-isomerMeSH, HMDB
Proline betaineChEBI
(2S)-1,1-Dimethylpyrrolidinium-2-carboxylatebiospider
L-Stachydrinemanual
Pyrrolidinium, 2-carboxy-1,1-dimethyl-, inner salt, (2S)-biospider
S-Stachydrinemanual
Stachydrine; L-formdb_source
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC7H13NO2
IUPAC name(2S)-1,1-dimethylpyrrolidin-1-ium-2-carboxylate
InChI IdentifierInChI=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
Isomeric SMILESC[N+]1(C)CCC[C@H]1C([O-])=O
Average Molecular Weight143.1836
Monoisotopic Molecular Weight143.094628665
Classification
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:

Foods

Fruits and vegetables:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionC 58.72%; H 9.15%; N 9.78%; O 22.35%DFC
Melting PointMp 235 dec. (anhyd.)DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]D -40.25 (c, 4 in H2O)DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSL-Stachydrine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-002e-9000000000-36bbb91342358293711aSpectrum
Predicted GC-MSL-Stachydrine, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-0bt9-9200000000-395432f0cf8795dd4cf7Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0900000000-ea4782d2282bc28329c0Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0007-4900000000-75a3b0df6adc0100b9feSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0aou-9000000000-5df24b6079668b584f79Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0900000000-34921bec4b2fad07f505Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-3900000000-da3a14fcb5a4909b775eSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000f-9000000000-7b04a861eee46ac86b66Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-9500000000-135bbe696520934e172eSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-9100000000-6d9ce7552b62c3e5d66cSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-059w-9100000000-1648e60acdd97fc80a9dSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0900000000-bf6e206b443f53ef90b5Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-0900000000-bf6e206b443f53ef90b5Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9200000000-94164ee813c486cb0b96Spectrum
NMRNot Available
ChemSpider ID103115
ChEMBL IDCHEMBL1456892
KEGG Compound IDC10172
Pubchem Compound ID115244
Pubchem Substance IDNot Available
ChEBI ID35280
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB04827
CRC / DFC (Dictionary of Food Compounds) IDBCP48-N:BCP49-O
EAFUS IDNot Available
Dr. Duke IDSTACHYDRINE|L-STACHYDRINE
BIGG IDNot Available
KNApSAcK IDC00002074
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
cardiotonic38070 A drug used for the treatment or prevention of cardiac arrhythmias. Anti-arrhythmia drugs may affect the polarisation-repolarisation phase of the action potential, its excitability or refractoriness, or impulse conduction or membrane responsiveness within cardiac fibres.DUKE
emmenagogueDUKE
insectifuge24852 Strictly, a substance intended to kill members of the class Insecta. In common usage, any substance used for preventing, destroying, repelling or controlling insects.DUKE
lactagogueDUKE
oxytocic36063 A drug that stimulates contraction of the myometrium. Oxytocics are used to induce labour, obstetric at term, to prevent or control postpartum or postabortion haemorrhage, and to assess foetal status in high risk pregnancies. They may also be used alone or with other drugs to induce abortions (abortifacients).DUKE
systolic depressantDUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.