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Human Metabolome Database Version 3.5

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Showing metabocard for Dimethylglycine (HMDB00092)

Record Information
Version 3.5
Creation Date 2005-11-16 08:48:42 -0700
Update Date 2013-02-08 17:07:53 -0700
HMDB ID HMDB00092
Secondary Accession Numbers None
Metabolite Identification
Common Name Dimethylglycine
Description Dimethylglycine (DMG) is an amino acid derivative found in the cells of all plants and animals and can be obtained in the diet in small amounts from grains and meat. The human body produces DMG when metabolizing choline into Glycine. Dimethylglycine that is not metabolized in the liver is transported by the circulatory system to body tissue. Dimethylglycine was popular with Russian athletes and cosmonauts owing to its reputed ability to increase endurance and reduce fatigue. DMG is also a byproduct of homocysteine metabolism. Homocysteine and betaine are converted to methionine and N, N-dimethylglycine by betaine-homocysteine methyltransferase.
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. (Dimethylamino)acetate
  2. (Dimethylamino)acetic acid
  3. 2-(Dimethylamino)acetate
  4. 2-(Dimethylamino)acetic acid
  5. Dimethylglycine
  6. N,N-Dimethylaminoacetate
  7. N,N-Dimethylaminoacetic acid
  8. N,N-Dimethylglycine
  9. N-Methylsarcosine N,N-dimethyl-Glycine
Chemical Formula C4H9NO2
Average Molecular Weight 103.1198
Monoisotopic Molecular Weight 103.063328537
IUPAC Name 2-(dimethylamino)acetic acid
Traditional IUPAC Name dimethylglycine
CAS Registry Number 1118-68-9
SMILES CN(C)CC(O)=O
InChI Identifier InChI=1S/C4H9NO2/c1-5(2)3-4(6)7/h3H2,1-2H3,(H,6,7)
InChI Key FFDGPVCHZBVARC-UHFFFAOYSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Amino Acids, Peptides, and Analogues
Class Amino Acids and Derivatives
Sub Class Alpha Amino Acids and Derivatives
Other Descriptors
  • Aliphatic Acyclic Compounds
  • amino acid zwitterion(ChEBI)
Substituents
  • Carboxylic Acid
  • Tertiary Aliphatic Amine (Trialkylamine)
Direct Parent Alpha Amino Acids and Derivatives
Ontology
Status Detected and Quantified
Origin
  • Endogenous
Biofunction
  • Component of Glycine, serine and threonine metabolism
  • Component of Methionine metabolism
Application Not Available
Cellular locations
  • Cytoplasm
  • Mitochondria
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point 185.5 °C Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP -2.91 TSAI,RS ET AL. (1991)
Predicted Properties
Property Value Source
Water Solubility 939 g/L ALOGPS
LogP -1.70 ALOGPS
LogP -3.1 ChemAxon
LogS 0.96 ALOGPS
pKa (strongest acidic) 1.88 ChemAxon
pKa (strongest basic) 9.69 ChemAxon
Hydrogen Acceptor Count 3 ChemAxon
Hydrogen Donor Count 1 ChemAxon
Polar Surface Area 40.54 A2 ChemAxon
Rotatable Bond Count 2 ChemAxon
Refractivity 26.07 ChemAxon
Polarizability 10.49 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 0 ChemAxon
Spectra
1H NMR Spectrum
13C NMR Spectrum
MS/MS Spectrum Quattro_QQQ 10
MS/MS Spectrum Quattro_QQQ 25
MS/MS Spectrum Quattro_QQQ 40
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 10
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 20
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 30
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 40
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 50
MS/MS Spectrum LC-ESI-QTOF (UPLC Q-Tof Premier, Waters)
MS/MS Spectrum LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30
MS/MS Spectrum LC-ESI-QTOF (UPLC Q-Tof Premier, Waters)
MS/MS Spectrum LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30
MS/MS Spectrum LC-ESI-QTOF (UPLC Q-Tof Premier, Waters)
MS/MS Spectrum GC-MS
[1H,1H] 2D NMR Spectrum
[1H,13C] 2D NMR Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Mitochondria
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Kidney
  • Liver
Pathways
Name SMPDB Link KEGG Link
Glycine and Serine Metabolism SMP00004 map00260 Link_out
Betaine Metabolism SMP00123 map00260 Link_out
Methionine Metabolism SMP00033 map00270 Link_out
Normal Concentrations
Biofluid Status Value Age Sex Condition Comments
Blood Detected and Quantified
Article_icon
2.6 (1.8-3.7) uM Adult (>18 years old) Both Normal Not Available
Blood Detected and Quantified
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1.9 (1.1-3.4) uM Adult (>18 years old) Both Normal Not Available
Urine Detected and not Quantified
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Not Applicable Adult (>18 years old) Both Normal Not Available
Urine Detected and Quantified
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4.4 (1.6-10.4) umol/mmol creatinine Adult (>18 years old) Both Normal urine by NMR
Urine Detected and Quantified
Article_icon
6.2 (0.8-11.2) umol/mmol creatinine Adult (>18 years old) Both Normal Not Available
Urine Detected and not Quantified
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Not Applicable Adult (>18 years old) Both Normal Urine compound detected by GC-MS
Urine Detected and Quantified
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3.4 (0.7-10.6) umol/mmol creatinine Adult (>18 years old) Both Normal Not Available
Abnormal Concentrations
Biofluid Status Value Age Sex Condition Comments
Blood Detected and Quantified
Article_icon
5.4 (3.1-7.2) uM Adult (>18 years old) Both Kidney disease Patient group: various renal conditions with...
Blood Detected and Quantified
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5.6 (4.8 - 10.1) uM Adult (>18 years old) Both Kidney disease Patients with various renal conditions on...
Blood Detected and Quantified
Article_icon
4.8 (3.6-6.2) uM Adult (>18 years old) Both Kidney disease Patients with chronic renal failure who were...
Associated Disorders and Diseases
Disease References
Kidney disease
  • McGregor DO, Dellow WJ, Lever M, George PM, Robson RA, Chambers ST: Dimethylglycine accumulates in uremia and predicts elevated plasma homocysteine concentrations. Kidney Int. 2001 Jun;59(6):2267-72. Pubmed: 11380830 Link_out
    Associated OMIM IDs None
    DrugBank ID Not Available
    Phenol Explorer Compound ID Not Available
    Phenol Explorer Metabolite ID Not Available
    FoodDB ID FDB021893
    KNApSAcK ID Not Available
    Chemspider ID 653 Link_out
    KEGG Compound ID C01026 Link_out
    BioCyc ID DIMETHYL-GLYCINE Link_out
    BiGG ID 36652 Link_out
    Wikipedia Link Dimethylglycine Link_out
    NuGOwiki Link HMDB00092 Link_out
    Metagene Link HMDB00092 Link_out
    METLIN ID 277 Link_out
    PubChem Compound 673 Link_out
    PDB ID DMG Link_out
    ChEBI ID 17724 Link_out
    References
    Synthesis Reference Lai, 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 po
    Material Safety Data Sheet (MSDS) Download (PDF)
    General References
    1. Binzak BA, Vockley JG, Jenkins RB, Vockley J: Structure and analysis of the human dimethylglycine dehydrogenase gene. Mol Genet Metab. 2000 Mar;69(3):181-7. Pubmed: 10767172 Link_out
    2. McGregor DO, Dellow WJ, Lever M, George PM, Robson RA, Chambers ST: Dimethylglycine accumulates in uremia and predicts elevated plasma homocysteine concentrations. Kidney Int. 2001 Jun;59(6):2267-72. Pubmed: 11380830 Link_out
    3. Moolenaar SH, Poggi-Bach J, Engelke UF, Corstiaensen JM, Heerschap A, de Jong JG, Binzak BA, Vockley J, Wevers RA: Defect in dimethylglycine dehydrogenase, a new inborn error of metabolism: NMR spectroscopy study. Clin Chem. 1999 Apr;45(4):459-64. Pubmed: 10102904 Link_out
    4. Look MP, Riezler R, Reichel C, Brensing KA, Rockstroh JK, Stabler SP, Spengler U, Berthold HK, Sauerbruch T: Is the increase in serum cystathionine levels in patients with liver cirrhosis a consequence of impaired homocysteine transsulfuration at the level of gamma-cystathionase? Scand J Gastroenterol. 2000 Aug;35(8):866-72. Pubmed: 10994627 Link_out
    5. Cicek G, Vuorinen T, Stahle I, Stepanek P, Freudenberg N, Brandsch R: Coxsackievirus B3 infection induces anti-flavoprotein antibodies in mice. Clin Exp Immunol. 2000 Dec;122(3):404-9. Pubmed: 11122247 Link_out
    6. Lever M, George PM, Dellow WJ, Scott RS, Chambers ST: Homocysteine, glycine betaine, and N,N-dimethylglycine in patients attending a lipid clinic. Metabolism. 2005 Jan;54(1):1-14. Pubmed: 15562374 Link_out
    7. Xia JH, Yu KP, Liu CY, Pan Q, Zheng D, Dai HP: [Molecular clonging of the human dimethyglycine dehydrogenase-like gene (DMGDHL1) from the sarcosinemia critical region at 9q34] Yi Chuan Xue Bao. 1999;26(6):591-7. Pubmed: 10876657 Link_out
    8. Laryea MD, Steinhagen F, Pawliczek S, Wendel U: Simple method for the routine determination of betaine and N,N-dimethylglycine in blood and urine. Clin Chem. 1998 Sep;44(9):1937-41. Pubmed: 9732980 Link_out
    9. Binzak BA, Wevers RA, Moolenaar SH, Lee YM, Hwu WL, Poggi-Bach J, Engelke UF, Hoard HM, Vockley JG, Vockley J: Cloning of dimethylglycine dehydrogenase and a new human inborn error of metabolism, dimethylglycine dehydrogenase deficiency. Am J Hum Genet. 2001 Apr;68(4):839-47. Epub 2001 Feb 28. Pubmed: 11231903 Link_out
    10. Jansen M, Hansen TA: Non-growth-associated demethylation of dimethylsulfoniopropionate by (homo)acetogenic bacteria. Appl Environ Microbiol. 2001 Jan;67(1):300-6. Pubmed: 11133459 Link_out
    Enzymes
    Name: Dimethylglycine dehydrogenase, mitochondrial
    Reactions:
    • N,N-dimethylglycine + acceptor + H2O = sarcosine + formaldehyde + reduced acceptor [RN:R01565]
    Gene Name: DMGDH
    Uniprot ID: Q9UI17 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: Betaine--homocysteine S-methyltransferase 1
    Reactions:
    • trimethylammonioacetate + L-homocysteine = dimethylglycine + L-methionine [RN:R02821]
    Gene Name: BHMT
    Uniprot ID: Q93088 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: Betaine--homocysteine S-methyltransferase 2
    Reactions:
    • trimethylammonioacetate + L-homocysteine = dimethylglycine + L-methionine [RN:R02821]
    Gene Name: BHMT2
    Uniprot ID: Q9H2M3 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA