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Record Information
Version1.0
Creation Date2016-09-30 22:19:32 UTC
Update Date2020-05-21 16:28:59 UTC
BMDB IDBMDB0000092
Secondary Accession Numbers
  • BMDB00092
Metabolite Identification
Common NameDimethylglycine
DescriptionDimethylglycine, also known as N-methylsarcosine, 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). Dimethylglycine exists as a solid, possibly soluble (in water), and a very strong basic compound (based on its pKa) molecule. Dimethylglycine exists in all living organisms, ranging from bacteria to humans. Dimethylglycine is a potentially toxic compound.
Structure
Thumb
Synonyms
ValueSource
(Dimethylamino)acetic acidChEBI
2-(Dimethylamino)acetic acidChEBI
N,N-Dimethylaminoacetic acidChEBI
N-MethylsarcosineChEBI
(Dimethylamino)acetateGenerator
2-(Dimethylamino)acetateGenerator
N,N-DimethylaminoacetateGenerator
N,N-DimethylglycineHMDB
N-Methylsarcosine N,N-dimethyl-glycineHMDB
Dimethylglycine, monopotassium saltHMDB
Dimethylglycine, sodium saltHMDB
Dimethylglycine, calcium saltHMDB
Dimethylglycine monohydrochlorideHMDB
2-(N,N-Dimethylamino)acetic acidHMDB
DMGHMDB
DimethylglycineHMDB
Chemical FormulaC4H9NO2
Average Molecular Weight103.1198
Monoisotopic Molecular Weight103.063328537
IUPAC NameNot Available
Traditional NameNot Available
CAS Registry Number1118-68-9
SMILESNot Available
InChI Identifier
InChI=1S/C4H9NO2/c1-5(2)3-4(6)7/h3H2,1-2H3,(H,6,7)
InChI KeyFFDGPVCHZBVARC-UHFFFAOYSA-N
Chemical Taxonomy
Description 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).
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentAlpha amino acids
Alternative Parents
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
  • Organic nitrogen compound
  • Carbonyl group
  • Amine
  • Hydrocarbon derivative
  • Organic oxide
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
StatusDetected but not Quantified
Origin
  • Endogenous
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm
  • Mitochondria
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point185.5 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP-2.91TSAI,RS ET AL. (1991)
Predicted PropertiesNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Biological Properties
Cellular Locations
  • Cytoplasm
  • Mitochondria
Biospecimen Locations
  • Blood
  • Kidney
  • Liver
  • Milk
  • Placenta
  • Ruminal Fluid
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
KidneyExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
LiverExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
MilkDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
MilkDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
PlacentaExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
Ruminal FluidDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
All Mycobacterium avium subsp. paratuberculosis-infected
details
BloodDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
High dose Mycobacterium avium subsp. paratuberculosis-infected
details
BloodDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Low dose Mycobacterium avium subsp. paratuberculosis-infected
details
HMDB IDHMDB0000092
DrugBank IDDB02083
Phenol Explorer Compound IDNot Available
FooDB IDFDB021893
KNApSAcK IDNot Available
Chemspider ID653
KEGG Compound IDC01026
BioCyc IDDIMETHYL-GLYCINE
BiGG ID36652
Wikipedia LinkDimethylglycine
METLIN ID277
PubChem Compound673
PDB IDNot Available
ChEBI ID17724
References
Synthesis ReferenceLai, Mei-Chin; Wang, Chia-Chi; Chuang, Ming-Jen; Wu, Yen-Chi; Lee, Yu-Chien. Effects of substrate and potassium on the betaine-synthesizing enzyme glycine sarcosine dimethylglycine N-methyltransferase from a halophilic methanoarchaeon Methanohalophilus portucalensis. Res Microbiol. 2006 Dec;157(10):948-55. Epub 2006 Oct 26. Pubmed: 17098399
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Pan L, Yu J, Mi Z, Mo L, Jin H, Yao C, Ren D, Menghe B: A Metabolomics Approach Uncovers Differences between Traditional and Commercial Dairy Products in Buryatia (Russian Federation). Molecules. 2018 Mar 22;23(4). pii: molecules23040735. doi: 10.3390/molecules23040735. [PubMed:29565828 ]
  2. Xi X, Kwok LY, Wang Y, Ma C, Mi Z, Zhang H: Ultra-performance liquid chromatography-quadrupole-time of flight mass spectrometry MS(E)-based untargeted milk metabolomics in dairy cows with subclinical or clinical mastitis. J Dairy Sci. 2017 Jun;100(6):4884-4896. doi: 10.3168/jds.2016-11939. Epub 2017 Mar 23. [PubMed:28342601 ]

Enzymes

General function:
Amino acid transport and metabolism
Specific function:
Involved in the regulation of homocysteine metabolism. Converts betaine and homocysteine to dimethylglycine and methionine, respectively. This reaction is also required for the irreversible oxidation of choline (By similarity).
Gene Name:
BHMT
Uniprot ID:
Q5I597
Molecular weight:
44878.0
Reactions
Betaine + Homocysteine → Dimethylglycine + L-Methioninedetails
General function:
Not Available
Specific function:
Decreases the sensitivity of PDP1 to magnesium ions, and this inhibition is reversed by the polyamine spermine.
Gene Name:
PDPR
Uniprot ID:
O46504
Molecular weight:
98857.0
Reactions
Dimethylglycine + Water → Formaldehyde + Sarcosinedetails