Record Information |
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Version | 2.0 |
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Creation Date | 2014-08-29 06:51:28 UTC |
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Update Date | 2014-12-24 20:26:51 UTC |
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Accession Number | T3D4458 |
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Identification |
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Common Name | Sarcosine |
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Class | Small Molecule |
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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 (1). |
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Compound Type | - Amine
- Animal Toxin
- Food Toxin
- Industrial/Workplace Toxin
- Lachrymator
- Metabolite
- Natural Compound
- Organic Compound
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Chemical Structure | |
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Synonyms | Synonym | (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 | Sarcosinic acid |
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Chemical Formula | C3H7NO2 |
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Average Molecular Mass | 89.093 g/mol |
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Monoisotopic Mass | 89.048 g/mol |
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CAS Registry Number | 107-97-1 |
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IUPAC Name | 2-(methylamino)acetic acid |
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Traditional Name | sarcosine |
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SMILES | CNCC(O)=O |
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InChI Identifier | InChI=1S/C3H7NO2/c1-4-2-3(5)6/h4H,2H2,1H3,(H,5,6) |
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InChI Key | InChIKey=FSYKKLYZXJSNPZ-UHFFFAOYSA-N |
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Chemical Taxonomy |
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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). |
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Kingdom | Organic compounds |
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Super Class | Organic acids and derivatives |
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Class | Carboxylic acids and derivatives |
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Sub Class | Amino acids, peptides, and analogues |
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Direct Parent | Alpha amino acids |
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Alternative Parents | |
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Substituents | - Alpha-amino acid
- Amino acid
- Carboxylic acid
- Secondary aliphatic amine
- Monocarboxylic acid or derivatives
- Secondary amine
- Organic nitrogen compound
- Hydrocarbon derivative
- Organooxygen compound
- Organonitrogen compound
- Organic oxide
- Organopnictogen compound
- Organic oxygen compound
- Carbonyl group
- Amine
- Aliphatic acyclic compound
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Molecular Framework | Aliphatic acyclic compounds |
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External Descriptors | |
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Biological Properties |
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Status | Detected and Not Quantified |
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Origin | Endogenous |
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Cellular Locations | |
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Biofluid Locations | Not Available |
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Tissue Locations | |
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Pathways | |
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Applications | Not Available |
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Biological Roles | |
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Chemical Roles | |
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Physical Properties |
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State | Solid |
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Appearance | White crystalline powder |
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Experimental Properties | Property | Value |
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Melting Point | 210°C | Boiling Point | Not Available | Solubility | 89.1 g/L | LogP | -2.78 |
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Predicted Properties | |
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Spectra |
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Spectra | Spectrum Type | Description | Splash Key | View |
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GC-MS | GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized) | splash10-014i-0900000000-3703e9255c5a3d53576e | JSpectraViewer | MoNA | GC-MS | GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS) | splash10-00xr-9800000000-b066cf015be7d1b1ec05 | JSpectraViewer | MoNA | GC-MS | GC-MS Spectrum - GC-MS (2 TMS) | splash10-014i-0900000000-73acbf4b13dbcd53efe1 | JSpectraViewer | MoNA | GC-MS | GC-MS Spectrum - EI-B (Non-derivatized) | splash10-014i-0900000000-22864bae97055c3845b6 | JSpectraViewer | MoNA | GC-MS | GC-MS Spectrum - GC-EI-TOF (Non-derivatized) | splash10-014i-0900000000-3703e9255c5a3d53576e | JSpectraViewer | MoNA | GC-MS | GC-MS Spectrum - GC-EI-TOF (Non-derivatized) | splash10-00xr-9800000000-b066cf015be7d1b1ec05 | JSpectraViewer | MoNA | GC-MS | GC-MS Spectrum - GC-MS (Non-derivatized) | splash10-014i-0900000000-73acbf4b13dbcd53efe1 | JSpectraViewer | MoNA | GC-MS | GC-MS Spectrum - GC-EI-TOF (Non-derivatized) | splash10-014i-0900000000-9559630483fd184becb6 | JSpectraViewer | MoNA | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-0006-9000000000-7a4141479c88d11af74a | JSpectraViewer | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive | splash10-0006-9000000000-847886894070391d8fdd | JSpectraViewer | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | Not Available | JSpectraViewer | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive | Not Available | JSpectraViewer | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive | Not Available | JSpectraViewer | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive | Not Available | JSpectraViewer | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated) | splash10-0006-9000000000-da0fd904589ef164065a | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated) | splash10-0006-9000000000-6b30a9c471d171cacad9 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated) | splash10-0006-9000000000-851a04dbd34e75febf9d | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative | splash10-000i-9000000000-86301ee1b7f5d158901e | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative | splash10-000i-9000000000-32b1ca1874d0fcb3f9c7 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative | splash10-000i-9000000000-37db595fcf7364600bc9 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive | splash10-0006-9000000000-0b3e92ad374e013024ea | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive | splash10-0006-9000000000-ef853c67634f1a7da8f5 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive | splash10-0006-9000000000-63e1ee6f897ea7a61e52 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive | splash10-0006-9000000000-bab0ab3587973d3ad4aa | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive | splash10-0006-9000000000-d017a51a9abbbcf31dce | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-000i-9000000000-86301ee1b7f5d158901e | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-000i-9000000000-645df370acbb7cac5322 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-000i-9000000000-37db595fcf7364600bc9 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , positive | splash10-0006-9000000000-0b3e92ad374e013024ea | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , positive | splash10-0006-9000000000-ef853c67634f1a7da8f5 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , positive | splash10-0006-9000000000-5701e8afc0a34aa34653 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , positive | splash10-0006-9000000000-bab0ab3587973d3ad4aa | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , positive | splash10-0006-9000000000-d017a51a9abbbcf31dce | JSpectraViewer | MoNA | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0006-9000000000-5fd27462e0d106e4c5a6 | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0006-9000000000-4f822ba462b1fbffce17 | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0006-9000000000-4125b1890cbe03ae7283 | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-000i-9000000000-c7e62ee2909dfb0a067c | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-000i-9000000000-8d4f2d4c6d399cbf0c9f | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-052f-9000000000-c8a4e61d51664ed38b96 | JSpectraViewer | MS | Mass Spectrum (Electron Ionization) | splash10-0006-9000000000-335905bb8c6b7e52ff70 | JSpectraViewer | MoNA | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 2D NMR | [1H,1H] 2D NMR Spectrum | Not Available | JSpectraViewer | 2D NMR | [1H,13C] 2D NMR Spectrum | Not Available | JSpectraViewer |
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Toxicity Profile |
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Route of Exposure | Endogenous, Eye contact, Ingestion. |
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Mechanism of Toxicity | Sarcosine is an oncometabolite. Sarcosine appears to upregulate the expression of the potent oncoprotein called human epidermal growth factor receptor 2 (HER2/neu) in androgen-dependent prostate cancer cells upon exposure to exogenous sarcosine. Thus, sarcosine may induce prostate cancer progression by increased HER2/neu expression. |
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Metabolism | Sarcosine is metabolized to glycine by the enzyme sarcosine dehydrogenase, while glycine-N-methyl transferase generates sarcosine from glycine. |
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Toxicity Values | NA |
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Lethal Dose | Not Available |
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Carcinogenicity (IARC Classification) | Not listed by IARC. Has been implicated in oncogenesis (12). |
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Uses/Sources | Sarcosine can be used as a cognitive enhancer and to treat schizophrenia. |
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Minimum Risk Level | Not Available |
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Health Effects | Acute Exposure: Can lead to eye and skin irritation.
Chronic Exposure: High levels of sarcosine in prostate tissues are associated with aggressive prostate tumors. In this regard, sarcosine appears to function as an oncometabolite. High levels of sarcosine are also seen in patients with sarcosinemia. Sarcosinemia is a rare inborn error of metabolism that is characterized by an increased level of sarcosine (N-methylglycine) in the plasma and urine. The enzymatic block results from a deficiency of sarcosine dehydrogenase (SarDH), a liver mitochondrial matrix enzyme that converts sarcosine into glycine. The disease is mostly characterized by mental delay, cardiomyopathy, deafness and visual disturbance. |
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Symptoms | Acute Exposure: eye irritation and skin irritation
Chronic Exposure: sarcosinemia is associated with mental delay, cardiomyopathy, deafness and visual disturbance. In individuals with prostate cancer, high prostate tissue levels of sarcosine promote aggressive, rapidly growing prostate tumors. |
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Treatment | Acute Exposure: EYES: irrigate opened eyes for several minutes under running water. INGESTION: do not induce vomiting. Rinse mouth with water (never give anything by mouth to an unconscious person). Seek immediate medical advice. SKIN: should be treated immediately by rinsing the affected parts in cold running water for at least 15 minutes, followed by thorough washing with soap and water. If necessary, the person should shower and change contaminated clothing and shoes, and then must seek medical attention. INHALATION: supply fresh air. If required provide artificial respiration. |
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Normal Concentrations |
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| Not Available |
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Abnormal Concentrations |
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| Not Available |
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External Links |
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DrugBank ID | Not Available |
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HMDB ID | HMDB00271 |
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PubChem Compound ID | 1088 |
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ChEMBL ID | CHEMBL304383 |
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ChemSpider ID | 1057 |
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KEGG ID | C00213 |
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UniProt ID | Not Available |
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OMIM ID | |
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ChEBI ID | 15611 |
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BioCyc ID | SARCOSINE |
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CTD ID | Not Available |
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Stitch ID | Not Available |
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PDB ID | SAR |
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ACToR ID | Not Available |
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Wikipedia Link | Sarcosine |
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References |
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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. |
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MSDS | Link |
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General References | - 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. doi: 10.1038/nature07762. [19212411 ]
- 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. [14708889 ]
- Akare S, Martinez JD: Bile acid induces hydrophobicity-dependent membrane alterations. Biochim Biophys Acta. 2005 Jun 15;1735(1):59-67. [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. [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. [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. [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. [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. [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. [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. [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. [8718672 ]
- Dahl M, Bouchelouche P, Kramer-Marek G, Capala J, Nordling J, Bouchelouche K. Sarcosine induces increase in HER2/neu expression in androgen-dependent prostate cancer cells. Mol Biol Rep. 2011 Oct;38(7):4237-43. doi: 10.1007/s11033-010-0442-2. Epub 2011 Jul 14. [21755295 ]
- International Agency for Research on Cancer (2014). IARC Monographs on the Evaluation of Carcinogenic Risks to Humans. [Link]
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Gene Regulation |
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Up-Regulated Genes | Not Available |
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Down-Regulated Genes | Not Available |
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