N,N,N-trimethylglycinium

Identification

Name
N,N,N-trimethylglycinium
Accession Number
DB04455  (EXPT00674)
Type
Small Molecule
Groups
Experimental, Investigational
Description

A naturally occurring compound that has been of interest for its role in osmoregulation. As a drug, betaine hydrochloride has been used as a source of hydrochloric acid in the treatment of hypochlorhydria. Betaine has also been used in the treatment of liver disorders, for hyperkalemia, for homocystinuria, and for gastrointestinal disturbances. (From Martindale, The Extra Pharmacopoeia, 30th ed, p1341)

Structure
Thumb
Synonyms
Not Available
Categories
Not Available
UNII
Not Available
CAS number
Not Available
Weight
Average: 118.1543
Monoisotopic: 118.086803633
Chemical Formula
C5H12NO2
InChI Key
KWIUHFFTVRNATP-UHFFFAOYSA-O
InChI
InChI=1S/C5H11NO2/c1-6(2,3)4-5(7)8/h4H2,1-3H3/p+1
IUPAC Name
(carboxymethyl)trimethylazanium
SMILES
C[N+](C)(C)CC(O)=O

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UGlycine betaine-binding periplasmic proteinNot AvailableEscherichia coli (strain K12)
UCircadian clock protein KaiBNot AvailableSynechocystis sp. (strain PCC 6803 / Kazusa)
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
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

General References
Not Available
External Links
Human Metabolome Database
HMDB0059606
PubChem Compound
248
PubChem Substance
46506049
ChemSpider
243
BindingDB
50357226
ChEBI
41139
ChEMBL
CHEMBL95889
HET
BET
PDB Entries
1r9l / 1rcc / 1rcd / 1rce / 1rcg / 1rci / 1sw2 / 1wwj / 2b4l / 2wit
show 15 more

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
2Active Not RecruitingOtherBMI >30 kg/m2 / Dysglycaemia1

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 Solubility1.75 mg/mLALOGPS
logP-2.1ALOGPS
logP-4.5ChemAxon
logS-1.9ALOGPS
pKa (Strongest Acidic)2.26ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity41.99 m3·mol-1ChemAxon
Polarizability12.52 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption-0.9526
Blood Brain Barrier+0.9018
Caco-2 permeable+0.6564
P-glycoprotein substrateNon-substrate0.7013
P-glycoprotein inhibitor INon-inhibitor0.991
P-glycoprotein inhibitor IINon-inhibitor0.9508
Renal organic cation transporterNon-inhibitor0.927
CYP450 2C9 substrateNon-substrate0.7998
CYP450 2D6 substrateNon-substrate0.844
CYP450 3A4 substrateNon-substrate0.5547
CYP450 1A2 substrateNon-inhibitor0.9401
CYP450 2C9 inhibitorNon-inhibitor0.9644
CYP450 2D6 inhibitorNon-inhibitor0.9381
CYP450 2C19 inhibitorNon-inhibitor0.9578
CYP450 3A4 inhibitorNon-inhibitor0.9854
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9928
Ames testNon AMES toxic0.9302
CarcinogenicityCarcinogens 0.6709
BiodegradationReady biodegradable0.8217
Rat acute toxicity2.2551 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9693
hERG inhibition (predictor II)Non-inhibitor0.9245
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

Taxonomy

Description
This compound belongs to the class of organic compounds known as alpha amino acids. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon).
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Carboxylic acids and derivatives
Sub Class
Amino acids, peptides, and analogues
Direct Parent
Alpha amino acids
Alternative Parents
Tetraalkylammonium salts / Monocarboxylic acids and derivatives / Carboxylic acids / Organopnictogen compounds / Organic salts / Organic oxides / Hydrocarbon derivatives / Carbonyl compounds / Amines / Organic cations
Substituents
Alpha-amino acid / Quaternary ammonium salt / Tetraalkylammonium salt / Monocarboxylic acid or derivatives / Carboxylic acid / Organic oxide / Organic nitrogen compound / Hydrocarbon derivative / Organic salt / Organooxygen compound
Molecular Framework
Aliphatic acyclic compounds
External Descriptors
quaternary ammonium ion (CHEBI:41139)

Targets

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. [PubMed:17139284]
  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. [PubMed:17016423]
Kind
Protein
Organism
Synechocystis sp. (strain PCC 6803 / Kazusa)
Pharmacological action
Unknown
General Function
Identical protein binding
Specific Function
Component of the KaiABC clock protein complex, which constitutes the main circadian regulator in cyanobacteria. The KaiABC complex may act as a promoter-non-specific transcription regulator that re...
Gene Name
kaiB
Uniprot ID
P74645
Uniprot Name
Circadian clock protein KaiB
Molecular Weight
11934.89 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. [PubMed:17139284]
  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. [PubMed:17016423]

Drug created on June 13, 2005 07:24 / Updated on November 02, 2018 05:57