Human Metabolome Database Version 3.5

Showing metabocard for Sarcosine (HMDB00271)

Record Information
Version 3.5
Creation Date 2005-11-16 08:48:42 -0700
Update Date 2013-05-29 13:25:19 -0600
HMDB ID HMDB00271
Secondary Accession Numbers None
Metabolite Identification
Common Name Sarcosine
Description Sarcosine 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 Link_out).
Structure Thumb
Download: MOL | SDF | PDB | SMILES | InChI
Display: 2D Structure | 3D Structure
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 Formula C3H7NO2
Average Molecular Weight 89.0932
Monoisotopic Molecular Weight 89.047678473
IUPAC Name 2-(methylamino)acetic acid
Traditional IUPAC Name sarcosine
CAS Registry Number 107-97-1
SMILES CNCC(O)=O
InChI Identifier InChI=1S/C3H7NO2/c1-4-2-3(5)6/h4H,2H2,1H3,(H,5,6)
InChI Key FSYKKLYZXJSNPZ-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
  • Secondary Aliphatic Amine (Dialkylamine)
Direct Parent Alpha Amino Acids and Derivatives
Ontology
Status Detected and Quantified
Origin
  • Endogenous
Biofunction
  • Component of Glycine, serine and threonine metabolism
Application Not Available
Cellular locations
  • Extracellular
  • Mitochondria
  • Peroxisome
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point 208 °C Not Available
Boiling Point Not Available Not Available
Water Solubility 300.0 mg/mL Not Available
LogP -2.78 HANSCH,C ET AL. (1995)
Predicted Properties
Property Value Source
Water Solubility 308 g/L ALOGPS
LogP -3.06 ALOGPS
LogP -3.2 ChemAxon
LogS 0.54 ALOGPS
pKa (strongest acidic) 2.06 ChemAxon
pKa (strongest basic) 10.35 ChemAxon
Hydrogen Acceptor Count 3 ChemAxon
Hydrogen Donor Count 2 ChemAxon
Polar Surface Area 49.33 A2 ChemAxon
Rotatable Bond Count 2 ChemAxon
Refractivity 20.78 ChemAxon
Polarizability 8.66 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 0 ChemAxon
Spectra
Gas-MS Spectrum
13C NMR Spectrum
1H 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) 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 GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies )
MS/MS Spectrum GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)
MS/MS Spectrum GC-MS
[1H,1H] 2D NMR Spectrum
[1H,13C] 2D NMR Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Mitochondria
  • Peroxisome
Biofluid Locations
  • Blood
  • Saliva
  • Urine
Tissue Location
  • Muscle
  • Skeletal Muscle
  • Prostate
Pathways
Name SMPDB Link KEGG Link
Glycine and Serine Metabolism SMP00004 map00260 Link_out
Normal Concentrations
Biofluid Status Value Age Sex Condition Reference
Blood Detected and Quantified
312.5 (0.00-625.00) uM Adult (>18 years old) Both Normal
Saliva Detected and Quantified
>10 uM Adult (>18 years old) Both Normal
Urine Detected and Quantified
0.47 umol/mmol creatinine Adult (>18 years old) Both Normal
Urine Detected and Quantified
2.8 (0.00-5.6) umol/mmol creatinine Adult (>18 years old) Both Normal
Urine Detected and Quantified
2.9 (0.5-5.4) umol/mmol creatinine Adult (>18 years old) Both Comment Normal
Urine Detected and Quantified
< 0.329 umol/mmol creatinine Adult (>18 years old) Both Normal
Urine Detected and Quantified
1.6 (0.2-9.4) umol/mmol creatinine Adult (>18 years old) Both Comment Normal
Urine Detected and Quantified
1.35 +/- 1.21 umol/mmol creatinine Infant (0-1 year old) Both Normal
Abnormal Concentrations
Biofluid Status Value Age Sex Condition Reference
Blood Detected and Quantified 300.0 (80.0-603.0) uM Children (1-13 year old) Both Sarcosinemia
Blood Detected and Quantified 405.00 (50.00-760.00) uM Children (1-13 year old) Both Sarcosinemia
Urine Detected and Quantified 2660.00 (240.00-5080.00) umol/mmol creatinine Children (1-13 year old) Both Sarcosinemia
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 Link_out
    Associated OMIM IDs
    DrugBank ID Not Available
    DrugBank Metabolite ID Not Available
    Phenol Explorer Compound ID Not Available
    Phenol Explorer Metabolite ID Not Available
    FoodDB ID FDB021925
    KNApSAcK ID Not Available
    Chemspider ID 1057 Link_out
    KEGG Compound ID C00213 Link_out
    BioCyc ID SARCOSINE Link_out
    BiGG ID 34275 Link_out
    Wikipedia Link Sarcosine Link_out
    NuGOwiki Link HMDB00271 Link_out
    Metagene Link HMDB00271 Link_out
    METLIN ID 51 Link_out
    PubChem Compound 1088 Link_out
    PDB ID SAR Link_out
    ChEBI ID 15611 Link_out
    References
    Synthesis Reference Cipens, 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) Download (PDF)
    General References
    1. 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 Link_out
    2. Akare S, Martinez JD: Bile acid induces hydrophobicity-dependent membrane alterations. Biochim Biophys Acta. 2005 Jun 15;1735(1):59-67. Pubmed: 15951237 Link_out
    3. 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 Link_out
    4. 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 Link_out
    5. 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 Link_out
    6. 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 Link_out
    7. 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 Link_out
    8. 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 Link_out
    9. 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 Link_out
    10. 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 Link_out
    11. 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 Link_out

    Enzymes
    Name: Peroxisomal sarcosine oxidase
    Reactions:
    Sarcosine + Water + Oxygen unknown Glycine + Formaldehyde + Hydrogen peroxide details
    Gene Name: PIPOX
    Uniprot ID: Q9P0Z9 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: Dimethylglycine dehydrogenase, mitochondrial
    Reactions:
    Dimethylglycine + electron-transfer flavoprotein + Water unknown Sarcosine + Formaldehyde + reduced electron-transfer flavoprotein details
    Dimethylglycine + Electron-transferring flavoprotein + Water unknown Sarcosine + Formaldehyde + Reduced electron-transferring flavoprotein details
    Gene Name: DMGDH
    Uniprot ID: Q9UI17 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: Glycine N-methyltransferase
    Reactions:
    S-Adenosylmethionine + Glycine unknown S-Adenosylhomocysteine + Sarcosine details
    Gene Name: GNMT
    Uniprot ID: Q14749 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: Sarcosine dehydrogenase, mitochondrial
    Reactions:
    Sarcosine + Water + electron-transfer flavoprotein unknown Glycine + Formaldehyde + reduced electron-transfer flavoprotein details
    Sarcosine + Electron-transferring flavoprotein + Water unknown Glycine + Formaldehyde + Reduced electron-transferring flavoprotein details
    Gene Name: SARDH
    Uniprot ID: Q9UL12 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: Proton-coupled amino acid transporter 2
    Reactions: Not Available
    Gene Name: SLC36A2
    Uniprot ID: Q495M3 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA