N,N-dimethylglycine

Identification

Name
N,N-dimethylglycine
Accession Number
DB02083  (EXPT01225)
Type
Small Molecule
Groups
Experimental
Description
Not Available
Structure
Thumb
Synonyms
  • (dimethylamino)acetic acid
  • 2-(Dimethylamino)acetic acid
  • Dimethylglycine
  • N-Methylsarcosine
  • N,N-Dimethylaminoacetic acid
Categories
UNII
7797M4CPPA
CAS number
1118-68-9
Weight
Average: 103.1198
Monoisotopic: 103.063328537
Chemical Formula
C4H9NO2
InChI Key
FFDGPVCHZBVARC-UHFFFAOYSA-N
InChI
InChI=1S/C4H9NO2/c1-5(2)3-4(6)7/h3H2,1-2H3,(H,6,7)
IUPAC Name
2-(dimethylamino)acetic acid
SMILES
CN(C)CC(O)=O

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UMonomeric sarcosine oxidaseNot AvailableBacillus sp. (strain B-0618)
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
PathwayCategory
Hyperglycinemia, non-ketoticDisease
Homocystinuria-megaloblastic anemia due to defect in cobalamin metabolism, cblG complementation typeDisease
Betaine MetabolismMetabolic
Cystathionine Beta-Synthase DeficiencyDisease
3-Phosphoglycerate dehydrogenase deficiencyDisease
Methionine MetabolismMetabolic
Methionine Adenosyltransferase DeficiencyDisease
HypermethioninemiaDisease
S-Adenosylhomocysteine (SAH) Hydrolase DeficiencyDisease
Glycine N-methyltransferase DeficiencyDisease
Non Ketotic HyperglycinemiaDisease
Dimethylglycine Dehydrogenase DeficiencyDisease
Sarcosine Oncometabolite Pathway Disease
Glycine and Serine MetabolismMetabolic
Dihydropyrimidine Dehydrogenase Deficiency (DHPD)Disease
Dimethylglycine Dehydrogenase DeficiencyDisease
SarcosinemiaDisease
Methylenetetrahydrofolate Reductase Deficiency (MTHFRD)Disease
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

Synthesis Reference

Roger V. Kendall, John W. Lawson, "Dimethylglycine enhancement of antibody production." U.S. Patent US5118618, issued December, 1982.

US5118618
General References
Not Available
External Links
Human Metabolome Database
HMDB00092
KEGG Compound
C01026
PubChem Compound
673
PubChem Substance
46507083
ChemSpider
653
ChEBI
58251
HET
DMG
Wikipedia
Dimethylglycine
PDB Entries
1el5 / 1vrq / 1x31 / 1xkp / 3so5 / 4e6r / 5cvd / 5him

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)185.5 °CPhysProp
boiling point (°C)63.9 °CPhysProp
logP-2.91TSAI,RS ET AL. (1991)
pKa2.04TSAI,RS ET AL. (1991)
Predicted Properties
PropertyValueSource
Water Solubility939.0 mg/mLALOGPS
logP-1.7ALOGPS
logP-3.1ChemAxon
logS0.96ALOGPS
pKa (Strongest Acidic)1.88ChemAxon
pKa (Strongest Basic)9.69ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area40.54 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity26.07 m3·mol-1ChemAxon
Polarizability10.47 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9652
Blood Brain Barrier+0.9325
Caco-2 permeable+0.6471
P-glycoprotein substrateNon-substrate0.7086
P-glycoprotein inhibitor INon-inhibitor0.9753
P-glycoprotein inhibitor IINon-inhibitor0.9693
Renal organic cation transporterNon-inhibitor0.9009
CYP450 2C9 substrateNon-substrate0.8119
CYP450 2D6 substrateNon-substrate0.8624
CYP450 3A4 substrateNon-substrate0.6141
CYP450 1A2 substrateNon-inhibitor0.8959
CYP450 2C9 inhibitorNon-inhibitor0.9751
CYP450 2D6 inhibitorNon-inhibitor0.9411
CYP450 2C19 inhibitorNon-inhibitor0.9739
CYP450 3A4 inhibitorNon-inhibitor0.9808
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9919
Ames testNon AMES toxic0.9363
CarcinogenicityCarcinogens 0.5934
BiodegradationReady biodegradable0.6461
Rat acute toxicity2.1692 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9489
hERG inhibition (predictor II)Non-inhibitor0.9504
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
GC-MS Spectrum - GC-MS (1 TMS)GC-MSsplash10-03gi-3900000000-fe42012cdac3329e6581
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
GC-MS Spectrum - GC-MSGC-MSsplash10-03gi-3900000000-fe42012cdac3329e6581
MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)LC-MS/MSsplash10-0a4i-9200000000-c3fc59f00bbe1e009053
MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)LC-MS/MSsplash10-0a4i-9000000000-7f6039bf537452ff6c93
MS/MS Spectrum - Quattro_QQQ 40V, PositiveLC-MS/MSsplash10-00dj-9100000000-b9c7546951d9f51f58d0
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, PositiveLC-MS/MSsplash10-0udi-2900000000-39eb87f9d7bffb116792
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, PositiveLC-MS/MSsplash10-0a4r-9100000000-c67140c27d7ca787f694
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, PositiveLC-MS/MSsplash10-0a4i-9000000000-9c9075d302e11b82ee64
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, PositiveLC-MS/MSsplash10-0a4i-9000000000-5c3302b240b5bdfde85d
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, PositiveLC-MS/MSsplash10-052f-9000000000-4ec4602699db0863421f
LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , PositiveLC-MS/MSsplash10-0zfr-6900000000-61f31e5540076abc389d
LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, PositiveLC-MS/MSsplash10-0a4i-9100000000-635be273cdf7a4cdfe53
LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , PositiveLC-MS/MSsplash10-0zfr-5900000000-5ca66452e93663c4d82a
LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, PositiveLC-MS/MSsplash10-0a4i-9200000000-0e2fb3ac0a1721a846b1
LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , NegativeLC-MS/MSsplash10-0udi-0900000000-02624b93137883b214ad
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
LC-MS/MS Spectrum - LC-ESI-QTOF , negativeLC-MS/MSsplash10-0udi-0900000000-02624b93137883b214ad
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-0udi-2900000000-39eb87f9d7bffb116792
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-0a4r-9100000000-c67140c27d7ca787f694
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-0a4i-9000000000-9c9075d302e11b82ee64
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-0a4i-9000000000-5c3302b240b5bdfde85d
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-052f-9000000000-9950e0391541ef1aaf5e
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0zfr-6900000000-61f31e5540076abc389d
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0a4i-9100000000-635be273cdf7a4cdfe53
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0zfr-5900000000-5ca66452e93663c4d82a
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0a4i-9200000000-0e2fb3ac0a1721a846b1
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-0a4i-9000000000-9d0d17533e18c417ce81
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-0006-9100000000-543c3c0716e6f385d54c
1H NMR Spectrum1D NMRNot Applicable
13C NMR Spectrum1D NMRNot Applicable
1H NMR Spectrum1D NMRNot Applicable
13C NMR Spectrum1D NMRNot Applicable
[1H,1H] 2D NMR Spectrum2D NMRNot Applicable
[1H,13C] 2D NMR Spectrum2D NMRNot Applicable

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
Trialkylamines / Amino acids / Monocarboxylic acids and derivatives / Carboxylic acids / Organopnictogen compounds / Organic oxides / Hydrocarbon derivatives / Carbonyl compounds
Substituents
Alpha-amino acid / Tertiary amine / Tertiary aliphatic amine / Amino acid / Carboxylic acid / Monocarboxylic acid or derivatives / Organopnictogen compound / Organic oxygen compound / Organooxygen compound / Organonitrogen compound
Molecular Framework
Aliphatic acyclic compounds
External Descriptors
N-methyl-amino acid, N-methylglycines (CHEBI:17724)

Targets

Kind
Protein
Organism
Bacillus sp. (strain B-0618)
Pharmacological action
Unknown
General Function
Sarcosine oxidase activity
Specific Function
Catalyzes the oxidative demethylation of sarcosine. Can also oxidize other secondary amino acids such as N-methyl-L-alanine.
Gene Name
soxA
Uniprot ID
P40859
Uniprot Name
Monomeric sarcosine oxidase
Molecular Weight
43181.395 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 09, 2017 03:09