Livestock Metabolome Database: Showing metabocard for Sarcosine (LMDB00124)

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-07-13 19:42:53 UTC

Update Date

2021-04-30 20:57:59 UTC

Lmdb

LMDB00124

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

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(Methylamino)acetic acid	ChEBI
(Methylamino)ethanoic acid	ChEBI
L-Sarcosine	ChEBI
MeGly	ChEBI
Methylaminoacetic acid	ChEBI
N-Methylaminoacetic acid	ChEBI
N-Methylglycine	ChEBI
Sar	ChEBI
Sarcosinic acid	ChEBI
(Methylamino)acetate	Generator
(Methylamino)ethanoate	Generator
Methylaminoacetate	Generator
N-Methylaminoacetate	Generator
Sarcosinate	Generator
(Methylamino)-acetate	HMDB
(Methylamino)-acetic acid	HMDB
Methylglycine	HMDB
N-Methyl-glycine	HMDB
Sarcosin	HMDB
Sodium sarcosinate	HMDB
Magnesium sarcosylate	HMDB
Sarcosinate, sodium	HMDB
Sarcosine hydrochloride	HMDB
Sarcosylate, magnesium	HMDB
N Methylglycine	HMDB
Sarcosine monosodium salt	HMDB

Chemical Formula

C₃H₇NO₂

Average Molecular Weight

89.0932

Monoisotopic Molecular Weight

89.047678473

IUPAC Name

2-(methylamino)acetic acid

Traditional 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

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).

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Alpha 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 Framework

Aliphatic acyclic compounds

External Descriptors

N-alkylglycine (CHEBI:15611 )
N-methyl-amino acid (CHEBI:15611 )
N-methylglycines (CHEBI:15611 )

Ontology

Status

Detected and Quantified

Origin

Not Available

Biofunction

Not Available

Application

Not Available

Cellular locations

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	-3.1	ALOGPS
logP	-3.2	ChemAxon
logS	0.54	ALOGPS
pKa (Strongest Acidic)	2.06	ChemAxon
pKa (Strongest Basic)	10.35	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	49.33 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	20.78 m³·mol⁻¹	ChemAxon
Polarizability	8.66 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-014i-0900000000-3703e9255c5a3d53576e	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)	splash10-00xr-9800000000-b066cf015be7d1b1ec05	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (2 TMS)	splash10-014i-0900000000-73acbf4b13dbcd53efe1	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-014i-0900000000-22864bae97055c3845b6	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-014i-0900000000-3703e9255c5a3d53576e	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00xr-9800000000-b066cf015be7d1b1ec05	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-014i-0900000000-73acbf4b13dbcd53efe1	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-014i-0900000000-9559630483fd184becb6	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9000000000-7a4141479c88d11af74a	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-0006-9000000000-847886894070391d8fdd	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-0006-9000000000-da0fd904589ef164065a	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-0006-9000000000-6b30a9c471d171cacad9	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-0006-9000000000-851a04dbd34e75febf9d	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-000i-9000000000-86301ee1b7f5d158901e	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-000i-9000000000-32b1ca1874d0fcb3f9c7	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-000i-9000000000-37db595fcf7364600bc9	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive	splash10-0006-9000000000-0b3e92ad374e013024ea	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive	splash10-0006-9000000000-ef853c67634f1a7da8f5	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive	splash10-0006-9000000000-63e1ee6f897ea7a61e52	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive	splash10-0006-9000000000-bab0ab3587973d3ad4aa	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive	splash10-0006-9000000000-d017a51a9abbbcf31dce	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-000i-9000000000-86301ee1b7f5d158901e	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-000i-9000000000-645df370acbb7cac5322	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-000i-9000000000-37db595fcf7364600bc9	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-0006-9000000000-0b3e92ad374e013024ea	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-0006-9000000000-ef853c67634f1a7da8f5	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-0006-9000000000-5701e8afc0a34aa34653	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-0006-9000000000-bab0ab3587973d3ad4aa	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-0006-9000000000-d017a51a9abbbcf31dce	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0006-9000000000-5fd27462e0d106e4c5a6	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0006-9000000000-4f822ba462b1fbffce17	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9000000000-4125b1890cbe03ae7283	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-9000000000-c7e62ee2909dfb0a067c	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-9000000000-8d4f2d4c6d399cbf0c9f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-052f-9000000000-c8a4e61d51664ed38b96	Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0006-9000000000-335905bb8c6b7e52ff70	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
2D NMR	[1H,1H] 2D NMR Spectrum	Not Available	Spectrum
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	Spectrum

Biological Properties

Cellular Locations

Not Available

Biofluid Locations and Tissue Locations

Follicular Fluid
Milk
Ruminal Fluid
Serum
Urine

Concentrations

Biofluid	Status	Value	Condition	Species	Reference	Details
Follicular Fluid	Detected and Quantified	100 +/- 0-130+/-0 uM	Not Available	Porcine	183842	details
Milk	Detected but not Quantified	Not Applicable	Not Available	Bovine	23438684	details
Ruminal Fluid	Detected and Quantified	36.9 +/- 30.5 uM	Not Available	Bovine	Saleem F, Bouatra...	details
Serum	Detected and Quantified	27.5449 +/- 38.1339 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	10.3281 +/- 17.0127 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	12 uM	Not Available	Porcine	Barbara U. Metzle...	details
Serum	Detected and Quantified	13.6 uM	Not Available	Porcine	Barbara U. Metzle...	details
Serum	Detected and Quantified	13.6 uM	Not Available	Porcine	Barbara U. Metzle...	details
Serum	Detected and Quantified	8.462 +/- 17.1398 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	13.8 uM	Not Available	Porcine	Barbara U. Metzle...	details
Serum	Detected and Quantified	3.8945 +/- 1.3838 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	14.1882 +/- 30.4181 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	27.6409 +/- 29.0704 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	10.2772 +/- 27.4473 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	14.3391 +/- 16.7532 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	3.16 +/- 1.52 uM	Not Available	Ovine	Candidate serum m...	details
Serum	Detected and Quantified	12.1725 +/- 9.7728 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	8.4948 +/- 7.0769 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	18.5974 +/- 22.5073 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	4.9287 +/- 1.7168 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	9.3096 +/- 6.5614 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	120 +/- 10 uM	Not Available	Porcine	183842	details
Serum	Detected and Quantified	8.7481 +/- 7.5332 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	4.2001 +/- 1.6053 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	5.255 +/- 1.8114 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	16.9582 +/- 18.4988 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	13.7363 +/- 30.7367 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	4.6804 +/- 2.139 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	25.5791 +/- 18.5153 uM	Normal	Ovine	Goldansaz et al.,...	details
Urine	Detected but not Quantified	Not Applicable	Not Available	Porcine	Federica Murgia, ...	details
Urine	Detected but not Quantified	Not Applicable	Not Available	Porcine	22661492	details
Urine	Detected but not Quantified	Not Applicable	Not Available	Porcine	22661492	details
Urine	Detected but not Quantified	Not Applicable	Not Available	Porcine	24696864	details

External Links

DrugBank ID

DB12519

HMDB ID

HMDB0000271

FooDB ID

FDB004048

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

34275

BioCyc ID

SARCOSINE

METLIN ID

PDB ID

Not Available

Wikipedia Link

Chemspider ID

ChEBI ID

PubChem Compound ID

Kegg Compound ID

YMDB ID

Not Available

ECMDB ID

ECMDB00271

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

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 ]

Showing metabocard for Sarcosine (LMDB00124)

Structure for LMDB00124 (Sarcosine)