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Showing Compound Sarkosin (FDB004048)

Record Information
Version1.0
Creation date2010-04-08 22:06:04 UTC
Update date2019-11-26 02:59:45 UTC
Primary IDFDB004048
Secondary Accession Numbers
  • FDB021925
Chemical Information
FooDB NameSarkosin
DescriptionSarcosine, also known as N-methylglycine or (methylamino)acetic acid, is a member of the class of compounds known as alpha amino acids. Alpha amino acids are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon). Sarcosine is soluble (in water) and a moderately acidic compound (based on its pKa). Sarcosine can be found in peanut, which makes sarcosine a potential biomarker for the consumption of this food product. Sarcosine can be found primarily in most biofluids, including blood, saliva, cerebrospinal fluid (CSF), and feces, as well as in human muscle, prostate and skeletal muscle tissues. Sarcosine exists in all living organisms, ranging from bacteria to humans. In humans, sarcosine is involved in few metabolic pathways, which include glycine and serine metabolism, methionine metabolism, and sarcosine oncometabolite pathway. Sarcosine is also involved in several metabolic disorders, some of which include homocystinuria-megaloblastic anemia due to defect in cobalamin metabolism, cblg complementation type, hyperglycinemia, non-ketotic, hypermethioninemia, and dimethylglycine dehydrogenase deficiency. Moreover, sarcosine is found to be associated with sarcosinemia. Sarcosine is a non-carcinogenic (not listed by IARC) potentially toxic compound.
CAS NumberNot Available
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
(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
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC3H7NO2
IUPAC name2-(methylamino)acetic acid
InChI IdentifierInChI=1S/C3H7NO2/c1-4-2-3(5)6/h4H,2H2,1H3,(H,5,6)
InChI KeyFSYKKLYZXJSNPZ-UHFFFAOYSA-N
Isomeric SMILESCNCC(O)=O
Average Molecular Weight89.0932
Monoisotopic Molecular Weight89.047678473
Classification
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
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-0006-9000000000-335905bb8c6b7e52ff702014-09-20View Spectrum
GC-MSSarkosin, non-derivatized, GC-MS Spectrumsplash10-014i-0900000000-3703e9255c5a3d53576eSpectrum
GC-MSSarkosin, 2 TMS, GC-MS Spectrumsplash10-00xr-9800000000-b066cf015be7d1b1ec05Spectrum
GC-MSSarkosin, 2 TMS, GC-MS Spectrumsplash10-014i-0900000000-73acbf4b13dbcd53efe1Spectrum
GC-MSSarkosin, non-derivatized, GC-MS Spectrumsplash10-014i-0900000000-22864bae97055c3845b6Spectrum
GC-MSSarkosin, non-derivatized, GC-MS Spectrumsplash10-014i-0900000000-3703e9255c5a3d53576eSpectrum
GC-MSSarkosin, non-derivatized, GC-MS Spectrumsplash10-00xr-9800000000-b066cf015be7d1b1ec05Spectrum
GC-MSSarkosin, non-derivatized, GC-MS Spectrumsplash10-014i-0900000000-73acbf4b13dbcd53efe1Spectrum
GC-MSSarkosin, non-derivatized, GC-MS Spectrumsplash10-014i-0900000000-9559630483fd184becb6Spectrum
Predicted GC-MSSarkosin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0006-9000000000-7a4141479c88d11af74aSpectrum
Predicted GC-MSSarkosin, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0006-9000000000-847886894070391d8fddSpectrum
Predicted GC-MSSarkosin, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSSarkosin, TMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSSarkosin, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSSarkosin, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0006-9000000000-da0fd904589ef164065a2012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0006-9000000000-6b30a9c471d171cacad92012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0006-9000000000-851a04dbd34e75febf9d2012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-000i-9000000000-86301ee1b7f5d158901e2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-000i-9000000000-32b1ca1874d0fcb3f9c72012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-000i-9000000000-37db595fcf7364600bc92012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-0006-9000000000-0b3e92ad374e013024ea2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-0006-9000000000-ef853c67634f1a7da8f52012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-0006-9000000000-63e1ee6f897ea7a61e522012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-0006-9000000000-bab0ab3587973d3ad4aa2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-0006-9000000000-d017a51a9abbbcf31dce2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-000i-9000000000-86301ee1b7f5d158901e2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-000i-9000000000-645df370acbb7cac53222017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-000i-9000000000-37db595fcf7364600bc92017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0006-9000000000-0b3e92ad374e013024ea2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0006-9000000000-ef853c67634f1a7da8f52017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0006-9000000000-5701e8afc0a34aa346532017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0006-9000000000-bab0ab3587973d3ad4aa2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0006-9000000000-d017a51a9abbbcf31dce2017-09-14View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-9000000000-5fd27462e0d106e4c5a62015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-9000000000-4f822ba462b1fbffce172015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-4125b1890cbe03ae72832015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-9000000000-c7e62ee2909dfb0a067c2015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-9000000000-8d4f2d4c6d399cbf0c9f2015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-9000000000-c8a4e61d51664ed38b962015-04-25View Spectrum
NMR
TypeDescriptionView
1D NMR13C NMR Spectrum (1D, 125 MHz, H2O, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, DMSO-d6, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 100.54 MHz, D2O, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, experimental)Spectrum
2D NMR[1H, 1H]-TOCSY. Unexported temporarily by An Chi on Oct 15, 2021 until json or nmrML file is generated. 2D NMR Spectrum (experimental)Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Spectrum
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound IDNot Available
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDHCM00-S:HCM00-S
EAFUS IDNot Available
Dr. Duke IDSARKOSIN
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).