Bovine Metabolome Database: Showing metabocard for Proline betaine (BMDB0004827)

Identification Taxonomy Physical properties Pathways Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-09-30 23:10:50 UTC

Update Date

2020-05-11 20:40:58 UTC

BMDB ID

BMDB0004827

Secondary Accession Numbers

BMDB04827

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. 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

Endogenous

Biofunction

Not Available

Application

Not Available

Cellular locations

Not Available

Physical Properties

State

Solid

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

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Liver
Placenta

Pathways

Not Available

Name	SMPDB/Pathwhiz	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Liver	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 31867104	details
Liver	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 31867104	details
Placenta	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details