L-proline betaine

Identification

Generic Name
L-proline betaine
DrugBank Accession Number
DB04284
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
Thumb
Weight
Average: 143.1836
Monoisotopic: 143.094628665
Chemical Formula
C7H13NO2
Synonyms
  • (S)-2-carboxylato-1,1-dimethylpyrrolidinium
  • L-stachydrine
  • Methyl hygrate betaine
  • Methyl hygrate βine
  • N,N-dimethyl-L-proline
  • Proline betaine
  • Stachydrine

Pharmacology

Indication

Not Available

Pharmacology
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Contraindications & Blackbox Warnings
Contraindications
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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UGlycine betaine-binding periplasmic proteinNot AvailableEscherichia coli (strain K12)
Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism
Not Available
Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
Medicalerrors
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Not Available
Food Interactions
Not Available

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as proline and derivatives. These 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
L-alpha-amino acids / Pyrrolidine carboxylic acids / N-alkylpyrrolidines / Tetraalkylammonium salts / Carboxylic acid salts / Monocarboxylic acids and derivatives / Carboxylic acids / Azacyclic compounds / Organopnictogen compounds / Organic salts
show 4 more
Substituents
Aliphatic heteromonocyclic compound / Alpha-amino acid / Amine / Azacycle / Carbonyl group / Carboxylic acid / Carboxylic acid salt / Hydrocarbon derivative / L-alpha-amino acid / Monocarboxylic acid or derivatives
show 15 more
Molecular Framework
Aliphatic heteromonocyclic compounds
External Descriptors
amino-acid betaine, alkaloid, N-methyl-L-alpha-amino acid (CHEBI:35280) / Pyrrolidine alkaloids (C10172)
Affected organisms
Not Available

Chemical Identifiers

UNII
S1L688345C
CAS number
471-87-4
InChI Key
CMUNUTVVOOHQPW-LURJTMIESA-N
InChI
InChI=1S/C7H13NO2/c1-8(2)5-3-4-6(8)7(9)10/h6H,3-5H2,1-2H3/t6-/m0/s1
IUPAC Name
(2S)-1,1-dimethylpyrrolidin-1-ium-2-carboxylate
SMILES
C[N+]1(C)CCC[C@H]1C([O-])=O

References

General References
Not Available
Human Metabolome Database
HMDB0004827
KEGG Compound
C10172
PubChem Compound
115244
PubChem Substance
46504751
ChemSpider
103115
ChEBI
35280
ChEMBL
CHEMBL1456892
PDBe Ligand
PBE

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.666 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
Polarizability15.05 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption-0.82
Blood Brain Barrier+0.9465
Caco-2 permeable+0.6036
P-glycoprotein substrateSubstrate0.5544
P-glycoprotein inhibitor INon-inhibitor0.977
P-glycoprotein inhibitor IINon-inhibitor0.9712
Renal organic cation transporterNon-inhibitor0.6707
CYP450 2C9 substrateNon-substrate0.7845
CYP450 2D6 substrateNon-substrate0.6877
CYP450 3A4 substrateSubstrate0.5967
CYP450 1A2 substrateNon-inhibitor0.9005
CYP450 2C9 inhibitorNon-inhibitor0.9374
CYP450 2D6 inhibitorNon-inhibitor0.9307
CYP450 2C19 inhibitorNon-inhibitor0.9349
CYP450 3A4 inhibitorNon-inhibitor0.966
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9912
Ames testNon AMES toxic0.8401
CarcinogenicityNon-carcinogens0.9472
BiodegradationReady biodegradable0.9658
Rat acute toxicity2.3948 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9718
hERG inhibition (predictor II)Non-inhibitor0.9513
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Targets

Drugtargets
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Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
Unknown
General Function
Transporter activity
Specific Function
Member of a multicomponent binding-protein-dependent transport system (the ProU transporter) which serves as the glycine betaine/L-proline transporter.
Gene Name
proX
Uniprot ID
P0AFM2
Uniprot Name
Glycine betaine-binding periplasmic protein
Molecular Weight
36022.345 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]

Drug created on June 13, 2005 13:24 / Updated on June 12, 2020 16:52