Livestock Metabolome Database: Showing metabocard for Proline betaine (LMDB00458)

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-07-13 19:50:18 UTC

Update Date

2016-09-23 18:45:31 UTC

Lmdb

LMDB00458

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Proline betaine

Description

Proline 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 soy beans (Glycine max), crosnes (Stachys affinis), domestic pigs (Sus scrofa domestica), limes (Citrus aurantiifolia), and triticales (X Triticosecale rimpaui). This could make proline betaine a potential biomarker for the consumption of these foods. Proline betaine is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review a significant number of articles have been published on Proline betaine.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(S)-2-Carboxylato-1,1-dimethylpyrrolidinium	ChEBI
N,N-Dimethyl-L-proline	ChEBI
Stachydrine	ChEBI
L-Proline betaine	Kegg
(2S)-2-Carboxy-1,1-dimethylpyrrolidinium	HMDB
(S)-2-Carboxy-1,1-dimethylpyrrolidinium	HMDB
Homostachydrine	HMDB
Prestwick-08g03	HMDB
Dimethylproline	MeSH, HMDB
Stachydrine chloride	MeSH, HMDB
Stachydrine chloride, (S)-isomer	MeSH, HMDB
Stachydrine, (+-)-isomer	MeSH, HMDB
Proline betaine	ChEBI

Chemical Formula

C₇H₁₃NO₂

Average Molecular Weight

143.1836

Monoisotopic Molecular Weight

143.094628665

IUPAC Name

(2S)-1,1-dimethylpyrrolidin-1-ium-2-carboxylate

Traditional Name

stachydrine

CAS Registry Number

471-87-4

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 Key

CMUNUTVVOOHQPW-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.

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

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 )

Ontology

Status

Detected but not Quantified

Origin

Not Available

Biofunction

Not Available

Application

Not Available

Cellular locations

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
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 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	60.11 m³·mol⁻¹	ChemAxon
Polarizability	15.05 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-002e-9000000000-36bbb91342358293711a	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-0bt9-9200000000-395432f0cf8795dd4cf7	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0006-0900000000-ea4782d2282bc28329c0	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0007-4900000000-75a3b0df6adc0100b9fe	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0aou-9000000000-5df24b6079668b584f79	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-0900000000-34921bec4b2fad07f505	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0006-3900000000-da3a14fcb5a4909b775e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-000f-9000000000-7b04a861eee46ac86b66	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0002-9500000000-135bbe696520934e172e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0002-9100000000-6d9ce7552b62c3e5d66c	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-059w-9100000000-1648e60acdd97fc80a9d	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-0900000000-bf6e206b443f53ef90b5	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0006-0900000000-bf6e206b443f53ef90b5	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9200000000-94164ee813c486cb0b96	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum

Biological Properties

Cellular Locations

Not Available

Biofluid Locations and Tissue Locations

Urine

Concentrations

Biofluid	Status	Value	Condition	Species	Reference	Details
Urine	Detected but not Quantified	Not Applicable	Not Available	Equine	E. E. Escalona, J...	details

External Links

DrugBank ID

DB04284

HMDB ID

HMDB0004827

FooDB ID

FDB000463

Phenol Explorer ID

Not Available

KNApSAcK ID

C00002074

BiGG ID

Not Available

BioCyc ID

CPD-821

METLIN ID

7089

PDB ID

Not Available

Wikipedia Link

Not Available

Chemspider ID

ChEBI ID

PubChem Compound ID

Kegg Compound ID

YMDB ID

Not Available

ECMDB ID

ECMDB21384

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General 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. [18060588 ]

Showing metabocard for Proline betaine (LMDB00458)

Structure for LMDB00458 (Proline betaine)