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Record Information
Version1.0
Creation Date2016-07-13 19:42:53 UTC
Update Date2021-04-30 20:57:59 UTC
LmdbLMDB00124
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
ValueSource
(Methylamino)acetic acidChEBI
(Methylamino)ethanoic acidChEBI
L-SarcosineChEBI
MeGlyChEBI
Methylaminoacetic acidChEBI
N-Methylaminoacetic acidChEBI
N-MethylglycineChEBI
SarChEBI
Sarcosinic acidChEBI
(Methylamino)acetateGenerator
(Methylamino)ethanoateGenerator
MethylaminoacetateGenerator
N-MethylaminoacetateGenerator
SarcosinateGenerator
(Methylamino)-acetateHMDB
(Methylamino)-acetic acidHMDB
MethylglycineHMDB
N-Methyl-glycineHMDB
SarcosinHMDB
Sodium sarcosinateHMDB
Magnesium sarcosylateHMDB
Sarcosinate, sodiumHMDB
Sarcosine hydrochlorideHMDB
Sarcosylate, magnesiumHMDB
N MethylglycineHMDB
Sarcosine monosodium saltHMDB
Chemical FormulaC3H7NO2
Average Molecular Weight89.0932
Monoisotopic Molecular Weight89.047678473
IUPAC Name2-(methylamino)acetic acid
Traditional 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
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
Ontology
StatusDetected and Quantified
OriginNot Available
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
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-0900000000-3703e9255c5a3d53576eSpectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)splash10-00xr-9800000000-b066cf015be7d1b1ec05Spectrum
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-014i-0900000000-73acbf4b13dbcd53efe1Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-014i-0900000000-22864bae97055c3845b6Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-014i-0900000000-3703e9255c5a3d53576eSpectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00xr-9800000000-b066cf015be7d1b1ec05Spectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-014i-0900000000-73acbf4b13dbcd53efe1Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-014i-0900000000-9559630483fd184becb6Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9000000000-7a4141479c88d11af74aSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0006-9000000000-847886894070391d8fddSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0006-9000000000-da0fd904589ef164065aSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0006-9000000000-6b30a9c471d171cacad9Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0006-9000000000-851a04dbd34e75febf9dSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-000i-9000000000-86301ee1b7f5d158901eSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-000i-9000000000-32b1ca1874d0fcb3f9c7Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-000i-9000000000-37db595fcf7364600bc9Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-0006-9000000000-0b3e92ad374e013024eaSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-0006-9000000000-ef853c67634f1a7da8f5Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-0006-9000000000-63e1ee6f897ea7a61e52Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-0006-9000000000-bab0ab3587973d3ad4aaSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-0006-9000000000-d017a51a9abbbcf31dceSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-000i-9000000000-86301ee1b7f5d158901eSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-000i-9000000000-645df370acbb7cac5322Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-000i-9000000000-37db595fcf7364600bc9Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0006-9000000000-0b3e92ad374e013024eaSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0006-9000000000-ef853c67634f1a7da8f5Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0006-9000000000-5701e8afc0a34aa34653Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0006-9000000000-bab0ab3587973d3ad4aaSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0006-9000000000-d017a51a9abbbcf31dceSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-9000000000-5fd27462e0d106e4c5a6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-9000000000-4f822ba462b1fbffce17Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-4125b1890cbe03ae7283Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-9000000000-c7e62ee2909dfb0a067cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-9000000000-8d4f2d4c6d399cbf0c9fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-9000000000-c8a4e61d51664ed38b96Spectrum
MSMass Spectrum (Electron Ionization)splash10-0006-9000000000-335905bb8c6b7e52ff70Spectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
2D NMR[1H,1H] 2D NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
Biological Properties
Cellular LocationsNot Available
Biofluid Locations and Tissue Locations
  • Follicular Fluid
  • Milk
  • Ruminal Fluid
  • Serum
  • Urine
Concentrations
BiofluidStatusValueConditionSpeciesReferenceDetails
Follicular FluidDetected and Quantified100 +/- 0-130+/-0 uMNot AvailablePorcine details
MilkDetected but not QuantifiedNot ApplicableNot AvailableBovine details
Ruminal FluidDetected and Quantified36.9 +/- 30.5 uMNot AvailableBovine
    • Saleem F, Bouatra...
details
SerumDetected and Quantified27.5449 +/- 38.1339 uM
Normal
Ovine
    • Goldansaz et al.,...
details
SerumDetected and Quantified10.3281 +/- 17.0127 uM
Normal
Ovine
    • Goldansaz et al.,...
details
SerumDetected and Quantified12 uMNot AvailablePorcine
    • Barbara U. Metzle...
details
SerumDetected and Quantified13.6 uMNot AvailablePorcine
    • Barbara U. Metzle...
details
SerumDetected and Quantified13.6 uMNot AvailablePorcine
    • Barbara U. Metzle...
details
SerumDetected and Quantified8.462 +/- 17.1398 uM
Normal
Ovine
    • Goldansaz et al.,...
details
SerumDetected and Quantified13.8 uMNot AvailablePorcine
    • Barbara U. Metzle...
details
SerumDetected and Quantified3.8945 +/- 1.3838 uM
Normal
Ovine
    • Goldansaz et al.,...
details
SerumDetected and Quantified14.1882 +/- 30.4181 uM
Normal
Ovine
    • Goldansaz et al.,...
details
SerumDetected and Quantified27.6409 +/- 29.0704 uM
Normal
Ovine
    • Goldansaz et al.,...
details
SerumDetected and Quantified10.2772 +/- 27.4473 uM
Normal
Ovine
    • Goldansaz et al.,...
details
SerumDetected and Quantified14.3391 +/- 16.7532 uM
Normal
Ovine
    • Goldansaz et al.,...
details
SerumDetected and Quantified3.16 +/- 1.52 uMNot AvailableOvine
    • Candidate serum m...
details
SerumDetected and Quantified12.1725 +/- 9.7728 uM
Normal
Ovine
    • Goldansaz et al.,...
details
SerumDetected and Quantified8.4948 +/- 7.0769 uM
Normal
Ovine
    • Goldansaz et al.,...
details
SerumDetected and Quantified18.5974 +/- 22.5073 uM
Normal
Ovine
    • Goldansaz et al.,...
details
SerumDetected and Quantified4.9287 +/- 1.7168 uM
Normal
Ovine
    • Goldansaz et al.,...
details
SerumDetected and Quantified9.3096 +/- 6.5614 uM
Normal
Ovine
    • Goldansaz et al.,...
details
SerumDetected and Quantified120 +/- 10 uMNot AvailablePorcine details
SerumDetected and Quantified8.7481 +/- 7.5332 uM
Normal
Ovine
    • Goldansaz et al.,...
details
SerumDetected and Quantified4.2001 +/- 1.6053 uM
Normal
Ovine
    • Goldansaz et al.,...
details
SerumDetected and Quantified5.255 +/- 1.8114 uM
Normal
Ovine
    • Goldansaz et al.,...
details
SerumDetected and Quantified16.9582 +/- 18.4988 uM
Normal
Ovine
    • Goldansaz et al.,...
details
SerumDetected and Quantified13.7363 +/- 30.7367 uM
Normal
Ovine
    • Goldansaz et al.,...
details
SerumDetected and Quantified4.6804 +/- 2.139 uM
Normal
Ovine
    • Goldansaz et al.,...
details
SerumDetected and Quantified25.5791 +/- 18.5153 uM
Normal
Ovine
    • Goldansaz et al.,...
details
UrineDetected but not QuantifiedNot ApplicableNot AvailablePorcine
    • Federica Murgia, ...
details
UrineDetected but not QuantifiedNot ApplicableNot AvailablePorcine details
UrineDetected but not QuantifiedNot ApplicableNot AvailablePorcine details
UrineDetected but not QuantifiedNot ApplicableNot AvailablePorcine details
DrugBank IDDB12519
HMDB IDHMDB0000271
FooDB IDFDB004048
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG ID34275
BioCyc IDSARCOSINE
METLIN ID51
PDB IDNot Available
Wikipedia LinkSarcosine
Chemspider ID1057
ChEBI ID15611
PubChem Compound ID1088
Kegg Compound IDC00213
YMDB IDNot Available
ECMDB IDECMDB00271
References
Synthesis ReferenceNot Available
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. doi: 10.1038/nature07762. [19212411 ]