Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2013-05-29 19:25:19 UTC
HMDB IDHMDB00271
Secondary Accession NumbersNone
Metabolite Identification
Common NameSarcosine
DescriptionSarcosine is the N-methyl derivative of glycine. Sarcosine is metabolized to glycine by the enzyme sarcosine dehydrogenase, while glycine-N-methyl transferase generates sarcosine from glycine. Sarcosine is a natural amino acid found in muscles and other body tissues. In the laboratory it may be synthesized from chloroacetic acid and methylamine. Sarcosine is naturally found in the metabolism of choline to glycine. Sarcosine is sweet to the taste and dissolves in water. It is used in manufacturing biodegradable surfactants and toothpastes as well as in other applications. Sarcosine is ubiquitous in biological materials and is present in such foods as egg yolks, turkey, ham, vegetables, legumes, etc. Sarcosine is formed from dietary intake of choline and from the metabolism of methionine, and is rapidly degraded to glycine. Sarcosine has no known toxicity, as evidenced by the lack of phenotypic manifestations of sarcosinemia, an inborn error of sarcosine metabolism. Sarcosinemia can result from severe folate deficiency because of the folate requirement for the conversion of sarcosine to glycine (Wikipedia). Sarcosine has recently been identified as a biomarker for invasive prostate cancer. It was found to be greatly increased during prostate cancer progression to metastasis and could be detected in urine. Sarcosine levels were also increased in invasive prostate cancer cell lines relative to benign prostate epithelial cells.(PMID: 19212411 ).
Structure
Thumb
Synonyms
  1. (methylamino)-Acetate
  2. (methylamino)-Acetic acid
  3. (Methylamino)acetate
  4. (Methylamino)acetic acid
  5. (Methylamino)ethanoate
  6. (Methylamino)ethanoic acid
  7. Methylglycine
  8. N-Methyl-Glycine
  9. N-Methylaminoacetate
  10. N-Methylaminoacetic acid
  11. N-Methylglycine
  12. Sarcosin
  13. Sarcosinate
  14. Sarcosine
  15. Sarcosinic acid
Chemical FormulaC3H7NO2
Average Molecular Weight89.0932
Monoisotopic Molecular Weight89.047678473
IUPAC Name2-(methylamino)acetic acid
Traditional IUPAC Namesarcosine
CAS Registry Number107-97-1
SMILES
CNCC(O)=O
InChI Identifier
InChI=1S/C3H7NO2/c1-4-2-3(5)6/h4H,2H2,1H3,(H,5,6)
InChI KeyFSYKKLYZXJSNPZ-UHFFFAOYSA-N
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassAmino Acids, Peptides, and Analogues
ClassAmino Acids and Derivatives
Sub ClassAlpha Amino Acids and Derivatives
Other Descriptors
  • Aliphatic Acyclic Compounds
  • amino acid zwitterion(ChEBI)
Substituents
  • Carboxylic Acid
  • Secondary Aliphatic Amine (Dialkylamine)
Direct ParentAlpha Amino Acids and Derivatives
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
Biofunction
  • Component of Glycine, serine and threonine metabolism
ApplicationNot Available
Cellular locations
  • Extracellular
  • Mitochondria
  • Peroxisome
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point208 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility300.0 mg/mLNot Available
LogP-2.78HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
water solubility308 g/LALOGPS
logP-3.1ALOGPS
logP-3.2ChemAxon
logS0.54ALOGPS
pKa (strongest acidic)2.06ChemAxon
pKa (strongest basic)10.35ChemAxon
physiological charge0ChemAxon
hydrogen acceptor count3ChemAxon
hydrogen donor count2ChemAxon
polar surface area49.33ChemAxon
rotatable bond count2ChemAxon
refractivity20.78ChemAxon
polarizability8.66ChemAxon
Spectra
Spectra
Biological Properties
Cellular Locations
  • Extracellular
  • Mitochondria
  • Peroxisome
Biofluid Locations
  • Blood
  • Saliva
  • Urine
Tissue Location
  • Muscle
  • Prostate
  • Skeletal Muscle
Pathways
NameSMPDB LinkKEGG Link
Glycine and Serine MetabolismSMP00004map00260
Normal Concentrations
BiofluidStatusValueAgeSexConditionReference
BloodDetected and Quantified312.5 (0.00-625.00) uMAdult (>18 years old)BothNormal
SalivaDetected and Quantified>10 uMAdult (>18 years old)BothNormal
UrineDetected and Quantified0.47 umol/mmol creatinineAdult (>18 years old)BothNormal
UrineDetected and Quantified2.8 (0.00-5.6) umol/mmol creatinineAdult (>18 years old)BothNormal
UrineDetected and Quantified2.9 (0.5-5.4) umol/mmol creatinineAdult (>18 years old)BothCommentNormal
UrineDetected and Quantified< 0.329 umol/mmol creatinineAdult (>18 years old)BothNormal
    UrineDetected and Quantified1.6 (0.2-9.4) umol/mmol creatinineAdult (>18 years old)BothCommentNormal
    UrineDetected and Quantified1.35 +/- 1.21 umol/mmol creatinineInfant (0-1 year old)BothNormal
    Abnormal Concentrations
    BiofluidStatusValueAgeSexConditionReference
    BloodDetected and Quantified300.0 (80.0-603.0) uMChildren (1-13 year old)BothSarcosinemia
    BloodDetected and Quantified405.00 (50.00-760.00) uMChildren (1-13 year old)BothSarcosinemia
    UrineDetected and Quantified2660.00 (240.00-5080.00) umol/mmol creatinineChildren (1-13 year old)BothSarcosinemia
    Associated Disorders and Diseases
    Disease References
    Sarcosinemia
    • Levy HL, Coulombe JT, Benjamin R: Massachusetts Metabolic Disorders Screening Program: III. Sarcosinemia. Pediatrics. 1984 Oct;74(4):509-13. Pubmed: 6207480
    Associated OMIM IDs
    DrugBank IDNot Available
    DrugBank Metabolite IDNot Available
    Phenol Explorer Compound IDNot Available
    Phenol Explorer Metabolite IDNot Available
    FoodDB IDFDB021925
    KNApSAcK IDNot Available
    Chemspider ID1057
    KEGG Compound IDC00213
    BioCyc IDSARCOSINE
    BiGG ID34275
    Wikipedia LinkSarcosine
    NuGOwiki LinkHMDB00271
    Metagene LinkHMDB00271
    METLIN ID51
    PubChem Compound1088
    PDB IDSAR
    ChEBI ID15611
    References
    Synthesis ReferenceCipens, G.; Slavinska, V.; Sile, D.; Kreile, D.; Strautina, A.; Krikis, A.; Gutmanis, A. Synthesis of sarcosine and its use. Latvijas PSR Zinatnu Akademijas Vestis, Kimijas Serija (1986), (5), 515-24.
    Material Safety Data Sheet (MSDS)Not Available
    General References
    1. Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. Pubmed: 19212411
    2. Shoemaker JD, Elliott WH: Automated screening of urine samples for carbohydrates, organic and amino acids after treatment with urease. J Chromatogr. 1991 Jan 2;562(1-2):125-38. Pubmed: 2026685
    3. Boulat O, Gradwohl M, Matos V, Guignard JP, Bachmann C: Organic acids in the second morning urine in a healthy Swiss paediatric population. Clin Chem Lab Med. 2003 Dec;41(12):1642-58. Pubmed: 14708889
    4. Silwood CJ, Lynch E, Claxson AW, Grootveld MC: 1H and (13)C NMR spectroscopic analysis of human saliva. J Dent Res. 2002 Jun;81(6):422-7. Pubmed: 12097436
    5. Akare S, Martinez JD: Bile acid induces hydrophobicity-dependent membrane alterations. Biochim Biophys Acta. 2005 Jun 15;1735(1):59-67. Pubmed: 15951237
    6. Lim DS, Roberts R, Marian AJ: Expression profiling of cardiac genes in human hypertrophic cardiomyopathy: insight into the pathogenesis of phenotypes. J Am Coll Cardiol. 2001 Oct;38(4):1175-80. Pubmed: 11583900
    7. Bales JR, Sadler PJ, Nicholson JK, Timbrell JA: Urinary excretion of acetaminophen and its metabolites as studied by proton NMR spectroscopy. Clin Chem. 1984 Oct;30(10):1631-6. Pubmed: 6206966
    8. Heil M, Podebrad F, Prado E, Beck T, Mosand A, Sewell AC, Bohles H, Lehnert W: Enantioselective analysis of ketone bodies in patients with beta-ketothiolase deficiency, medium-chain acyl coenzyme A dehydrogenase deficiency and ketonemic vomiting. J Chromatogr B Biomed Sci Appl. 2000 Mar 10;739(2):313-24. Pubmed: 10755375
    9. Kang ES, Seyer J, Todd TA, Herrera C: Variability in the phenotypic expression of abnormal sarcosine metabolism in a family. Hum Genet. 1983;64(1):80-5. Pubmed: 6192074
    10. Vallera DA, Todhunter DA, Kuroki DW, Shu Y, Sicheneder A, Chen H: A bispecific recombinant immunotoxin, DT2219, targeting human CD19 and CD22 receptors in a mouse xenograft model of B-cell leukemia/lymphoma. Clin Cancer Res. 2005 May 15;11(10):3879-88. Pubmed: 15897589
    11. Hitomi J, Yamaguchi K, Kikuchi Y, Kimura T, Maruyama K, Nagasaki K: A novel calcium-binding protein in amniotic fluid, CAAF1: its molecular cloning and tissue distribution. J Cell Sci. 1996 Apr;109 ( Pt 4):805-15. Pubmed: 8718672

    Enzymes

    Gene Name:
    PIPOX
    Uniprot ID:
    Q9P0Z9
    Reactions
    Sarcosine + Water + Oxygen unknown Glycine + Formaldehyde + Hydrogen peroxidedetails
    Gene Name:
    DMGDH
    Uniprot ID:
    Q9UI17
    Reactions
    Dimethylglycine + electron-transfer flavoprotein + Water unknown Sarcosine + Formaldehyde + reduced electron-transfer flavoproteindetails
    Dimethylglycine + Electron-transferring flavoprotein + Water unknown Sarcosine + Formaldehyde + Reduced electron-transferring flavoproteindetails
    Gene Name:
    GNMT
    Uniprot ID:
    Q14749
    Reactions
    S-Adenosylmethionine + Glycine unknown S-Adenosylhomocysteine + Sarcosinedetails
    Gene Name:
    SARDH
    Uniprot ID:
    Q9UL12
    Reactions
    Sarcosine + Water + electron-transfer flavoprotein unknown Glycine + Formaldehyde + reduced electron-transfer flavoproteindetails
    Sarcosine + Electron-transferring flavoprotein + Water unknown Glycine + Formaldehyde + Reduced electron-transferring flavoproteindetails
    Gene Name:
    SLC36A2
    Uniprot ID:
    Q495M3