| Record Information |
|---|
| Version |
3.5 |
| Creation Date |
2005-11-16 08:48:42 -0700 |
| Update Date |
2013-02-08 17:08:13 -0700 |
| 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  ). |
| Structure |
Download:
MOL |
SDF |
SMILES |
InChI
Display:
2D Structure |
3D Structure
|
| Synonyms |
- (methylamino)-Acetate
- (methylamino)-Acetic acid
- (Methylamino)acetate
- (Methylamino)acetic acid
- (Methylamino)ethanoate
- (Methylamino)ethanoic acid
- Methylglycine
- N-Methyl-Glycine
- N-Methylaminoacetate
- N-Methylaminoacetic acid
- N-Methylglycine
- Sarcosin
- Sarcosinate
- Sarcosine
- 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 |
|
| Biofunction |
- Component of Glycine, serine and threonine metabolism
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| Application |
Not Available |
| Cellular locations |
- Extracellular
- Mitochondria
- Peroxisome
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| 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) |
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| Predicted Properties |
|
| Spectra |
|---|
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| 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
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| Biofluid Locations |
|
| Tissue Location |
- Muscle
- Skeletal Muscle
- Prostate
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| Pathways |
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| Normal Concentrations |
|---|
|
| Saliva |
Detected and Quantified |
|
>10 uM |
Adult (>18 years old) |
Both |
Normal |
Not Available |
| Urine |
Detected and Quantified |
|
0.47 umol/mmol creatinine |
Adult (>18 years old) |
Both |
Normal |
Not Available |
| Urine |
Detected and Quantified |
|
2.9 (0.5-5.4) umol/mmol creatinine |
Adult (>18 years old) |
Both |
Normal |
urine by NMR
|
| Urine |
Detected and Quantified |
|
< 0.329 umol/mmol creatinine |
Adult (>18 years old) |
Both |
Normal |
Not Available |
| Urine |
Detected and Quantified |
|
1.6 (0.2-9.4) umol/mmol creatinine |
Adult (>18 years old) |
Both |
Normal |
by LC-MS/MS (Biocrates kit)
|
| Urine |
Detected and Quantified |
|
1.35 +/- 1.21 umol/mmol creatinine |
Infant (0-1 year old) |
Both |
Normal |
Not Available |
|
| Abnormal Concentrations |
|---|
|
| Blood |
Detected and Quantified |
|
300.0 (80.0-603.0) uM |
Children (1-13 year old) |
Both |
Sarcosinemia |
Not Available |
| Blood |
Detected and Quantified |
|
312.5 (0.00-625.00) uM |
Adult (>18 years old) |
Both |
Sarcosinemia |
Not Available |
| Blood |
Detected and Quantified |
|
405.00 (50.00-760.00) uM |
Adult (>18 years old) |
Both |
Sarcosinemia |
Not Available |
| Urine |
Detected and Quantified |
|
1.8 (0.00-3.6) umol/mmol creatinine |
Adult (>18 years old) |
Both |
Sarcosinemia |
Not Available |
| Urine |
Detected and Quantified |
|
2660.00 (240.00-5080.00) umol/mmol creatinine |
Adult (>18 years old) |
Both |
Sarcosinemia |
Not Available |
|
| 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
- http://www.metagene.de/program/d.prg?mp=SARCOSINEMIA
|
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| Associated OMIM IDs |
|
| External Links |
|---|
| DrugBank 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 |
| KEGG Compound ID |
C00213 |
| BioCyc ID |
SARCOSINE |
| BiGG ID |
34275 |
| Wikipedia Link |
Sarcosine |
| NuGOwiki Link |
HMDB00271 |
| Metagene Link |
HMDB00271 |
| METLIN ID |
51 |
| PubChem Compound |
1088 |
| PDB ID |
SAR |
| ChEBI ID |
15611 |
| 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 |
- 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
- Akare S, Martinez JD: Bile acid induces hydrophobicity-dependent membrane alterations. Biochim Biophys Acta. 2005 Jun 15;1735(1):59-67.
Pubmed: 15951237
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
|
