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Record Information
Version2.0
Creation Date2014-08-29 06:51:28 UTC
Update Date2014-12-24 20:26:51 UTC
Accession NumberT3D4458
Identification
Common NameSarcosine
ClassSmall Molecule
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 (1).
Compound Type
  • Amine
  • Animal Toxin
  • Food Toxin
  • Industrial/Workplace Toxin
  • Lachrymator
  • Metabolite
  • Natural Compound
  • Organic Compound
Chemical Structure
Thumb
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
Chemical FormulaC3H7NO2
Average Molecular Mass89.093 g/mol
Monoisotopic Mass89.048 g/mol
CAS Registry Number107-97-1
IUPAC Name2-(methylamino)acetic acid
Traditional Namesarcosine
SMILESCNCC(O)=O
InChI IdentifierInChI=1S/C3H7NO2/c1-4-2-3(5)6/h4H,2H2,1H3,(H,5,6)
InChI KeyInChIKey=FSYKKLYZXJSNPZ-UHFFFAOYSA-N
Chemical Taxonomy
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).
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentAlpha amino acids
Alternative Parents
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
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginEndogenous
Cellular Locations
  • Cytoplasm
  • Extracellular
Biofluid LocationsNot Available
Tissue Locations
  • All Tissues
Pathways
NameSMPDB LinkKEGG Link
Glycine and Serine MetabolismSMP00004 map00260
SarcosinemiaSMP00244 Not Available
ApplicationsNot Available
Biological Roles
Chemical Roles
Physical Properties
StateSolid
AppearanceWhite crystalline powder
Experimental Properties
PropertyValue
Melting Point210°C
Boiling PointNot Available
Solubility89.1 g/L
LogP-2.78
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 Area49.33 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity20.78 m³·mol⁻¹ChemAxon
Polarizability8.66 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-014i-0900000000-3703e9255c5a3d53576eJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)splash10-00xr-9800000000-b066cf015be7d1b1ec05JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-014i-0900000000-73acbf4b13dbcd53efe1JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-014i-0900000000-22864bae97055c3845b6JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-014i-0900000000-3703e9255c5a3d53576eJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00xr-9800000000-b066cf015be7d1b1ec05JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-014i-0900000000-73acbf4b13dbcd53efe1JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-014i-0900000000-9559630483fd184becb6JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9000000000-7a4141479c88d11af74aJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0006-9000000000-847886894070391d8fddJSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0006-9000000000-da0fd904589ef164065aJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0006-9000000000-6b30a9c471d171cacad9JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0006-9000000000-851a04dbd34e75febf9dJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-000i-9000000000-86301ee1b7f5d158901eJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-000i-9000000000-32b1ca1874d0fcb3f9c7JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-000i-9000000000-37db595fcf7364600bc9JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-0006-9000000000-0b3e92ad374e013024eaJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-0006-9000000000-ef853c67634f1a7da8f5JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-0006-9000000000-63e1ee6f897ea7a61e52JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-0006-9000000000-bab0ab3587973d3ad4aaJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-0006-9000000000-d017a51a9abbbcf31dceJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-000i-9000000000-86301ee1b7f5d158901eJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-000i-9000000000-645df370acbb7cac5322JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-000i-9000000000-37db595fcf7364600bc9JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0006-9000000000-0b3e92ad374e013024eaJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0006-9000000000-ef853c67634f1a7da8f5JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0006-9000000000-5701e8afc0a34aa34653JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0006-9000000000-bab0ab3587973d3ad4aaJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0006-9000000000-d017a51a9abbbcf31dceJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-9000000000-5fd27462e0d106e4c5a6JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-9000000000-4f822ba462b1fbffce17JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-4125b1890cbe03ae7283JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-9000000000-c7e62ee2909dfb0a067cJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-9000000000-8d4f2d4c6d399cbf0c9fJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-9000000000-c8a4e61d51664ed38b96JSpectraViewer
MSMass Spectrum (Electron Ionization)splash10-0006-9000000000-335905bb8c6b7e52ff70JSpectraViewer | MoNA
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,1H] 2D NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableJSpectraViewer
Toxicity Profile
Route of ExposureEndogenous, Eye contact, Ingestion.
Mechanism of ToxicitySarcosine 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.
MetabolismSarcosine is metabolized to glycine by the enzyme sarcosine dehydrogenase, while glycine-N-methyl transferase generates sarcosine from glycine.
Toxicity ValuesNA
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not listed by IARC. Has been implicated in oncogenesis (12).
Uses/SourcesSarcosine can be used as a cognitive enhancer and to treat schizophrenia.
Minimum Risk LevelNot Available
Health EffectsAcute 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.
SymptomsAcute 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.
TreatmentAcute 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.
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB00271
PubChem Compound ID1088
ChEMBL IDCHEMBL304383
ChemSpider ID1057
KEGG IDC00213
UniProt IDNot Available
OMIM ID
ChEBI ID15611
BioCyc IDSARCOSINE
CTD IDNot Available
Stitch IDNot Available
PDB IDSAR
ACToR IDNot Available
Wikipedia LinkSarcosine
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.
MSDSLink
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. doi: 10.1038/nature07762. [19212411 ]
  2. 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 ]
  3. Akare S, Martinez JD: Bile acid induces hydrophobicity-dependent membrane alterations. Biochim Biophys Acta. 2005 Jun 15;1735(1):59-67. [15951237 ]
  4. 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 ]
  5. 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 ]
  6. 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 ]
  7. 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 ]
  8. 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 ]
  9. 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 ]
  10. 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 ]
  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. [8718672 ]
  12. 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 ]
  13. International Agency for Research on Cancer (2014). IARC Monographs on the Evaluation of Carcinogenic Risks to Humans. [Link]
Gene Regulation
Up-Regulated GenesNot Available
Down-Regulated GenesNot Available

Targets

General Function:
L-proline transmembrane transporter activity
Specific Function:
Neutral amino acid/proton symporter. Has a pH-dependent electrogenic transport activity for small amino acids such as glycine, alanine and proline. Besides small apolar L-amino acids, it also recognize their D-enantiomers and selected amino acid derivatives such as gamma-aminobutyric acid (By similarity).
Gene Name:
SLC36A1
Uniprot ID:
Q7Z2H8
Molecular Weight:
53075.045 Da
Binding/Activity Constants
TypeValueAssay TypeAssay Source
Inhibitory1900 uMNot AvailableBindingDB 50017225
References
  1. Thondorf I, Voigt V, Schafer S, Gebauer S, Zebisch K, Laug L, Brandsch M: Three-dimensional quantitative structure-activity relationship analyses of substrates of the human proton-coupled amino acid transporter 1 (hPAT1). Bioorg Med Chem. 2011 Nov 1;19(21):6409-18. doi: 10.1016/j.bmc.2011.08.058. Epub 2011 Sep 5. [21955456 ]
General Function:
Temperature-gated cation channel activity
Specific Function:
Receptor-activated non-selective cation channel involved in detection of pain and possibly also in cold perception and inner ear function (PubMed:25389312, PubMed:25855297). Has a central role in the pain response to endogenous inflammatory mediators and to a diverse array of volatile irritants, such as mustard oil, cinnamaldehyde, garlic and acrolein, an irritant from tears gas and vehicule exhaust fumes (PubMed:25389312, PubMed:20547126). Is also activated by menthol (in vitro)(PubMed:25389312). Acts also as a ionotropic cannabinoid receptor by being activated by delta(9)-tetrahydrocannabinol (THC), the psychoactive component of marijuana (PubMed:25389312). May be a component for the mechanosensitive transduction channel of hair cells in inner ear, thereby participating in the perception of sounds. Probably operated by a phosphatidylinositol second messenger system (By similarity).
Gene Name:
TRPA1
Uniprot ID:
O75762
Molecular Weight:
127499.88 Da
References
  1. Nilius B, Prenen J, Owsianik G: Irritating channels: the case of TRPA1. J Physiol. 2011 Apr 1;589(Pt 7):1543-9. doi: 10.1113/jphysiol.2010.200717. Epub 2010 Nov 15. [21078588 ]