Bovine Metabolome Database: Showing metabocard for Sarcosine (BMDB0000271)

Identification Taxonomy Physical properties Pathways Spectra Concentrations Links References enzymes (3) Show 3 proteins XML

Record Information

Version

1.0

Creation Date

2016-09-30 22:27:41 UTC

Update Date

2020-06-04 20:03:28 UTC

BMDB ID

BMDB0000271

Secondary Accession Numbers

BMDB00271

Metabolite Identification

Common Name

Sarcosine

Description

Sarcosine, also known as N-methylglycine or megly, 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). Sarcosine exists as a solid, possibly soluble (in water), and a very strong basic compound (based on its pKa) molecule. Sarcosine exists in all living organisms, ranging from bacteria to humans. Sarcosine is a potentially toxic compound.

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

Endogenous

Biofunction

Not Available

Application

Not Available

Cellular locations

Cytoplasm
Mitochondria
Peroxisome

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	208 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	300.0 mg/mL	Not Available
LogP	-2.78	HANSCH,C ET AL. (1995)

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

Biological Properties

Cellular Locations

Cytoplasm
Mitochondria
Peroxisome

Biospecimen Locations

Blood
Liver
Longissimus Thoracis Muscle
Mammary Gland
Milk
Prostate Tissue
Ruminal Fluid
Semimembranosus Muscle
Testis

Pathways

Name	SMPDB/Pathwhiz	KEGG
Glycine and Serine Metabolism		Not Available
Methionine Metabolism		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	3 +/- 1 uM	Not Specified	Not Specified	Normal	Aidin Foroutan, C...	details
Blood	Detected and Quantified	10-12 uM	Not Specified	Not Specified	Normal	PMID: 28036059	details
Liver	Detected and Quantified	23 +/- 10 nmol/g of tissue	Not Specified	Not Specified	Normal	Aidin Foroutan, C...	details
Liver	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 31873721	details
Liver	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 31873721	details
Longissimus Thoracis Muscle	Detected and Quantified	12 +/- 5 nmol/g of tissue	Not Specified	Not Specified	Normal	Aidin Foroutan, C...	details
Mammary Gland	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 31873721	details
Mammary Gland	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 31873721	details
Milk	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 23438684	details
Milk	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 29291809	details
Prostate Tissue	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Ruminal Fluid	Detected and Quantified	2 +/- 1 uM	Not Specified	Not Specified	Normal	Aidin Foroutan, C...	details
Ruminal Fluid	Detected and Quantified	36.9 +/- 30.5 uM	Not Specified	Not Specified	Normal	Fozia Saleem, Sou...	details
Ruminal Fluid	Detected and Quantified	6.9 +/- 30.53 uM	Not Specified	Not Specified	Normal	Fozia Saleem, Sou...	details
Semimembranosus Muscle	Detected and Quantified	10 +/- 4 nmol/g of tissue	Not Specified	Not Specified	Normal	Aidin Foroutan, C...	details
Testis	Detected and Quantified	5 +/- 2 nmol/g of tissue	Not Specified	Not Specified	Normal	Aidin Foroutan, C...	details

Abnormal Concentrations

Not Available

External Links

HMDB ID

HMDB0000271

DrugBank ID

DB12519

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB004048

KNApSAcK ID

Not Available

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Wikipedia Link

METLIN ID

PubChem Compound

1088

PDB ID

Not Available

ChEBI ID

15611

References

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.

Material Safety Data Sheet (MSDS)

Not Available

General References

Melzer N, Wittenburg D, Hartwig S, Jakubowski S, Kesting U, Willmitzer L, Lisec J, Reinsch N, Repsilber D: Investigating associations between milk metabolite profiles and milk traits of Holstein cows. J Dairy Sci. 2013 Mar;96(3):1521-34. doi: 10.3168/jds.2012-5743. [PubMed:23438684 ]
Mung D, Li L: Applying quantitative metabolomics based on chemical isotope labeling LC-MS for detecting potential milk adulterant in human milk. Anal Chim Acta. 2018 Feb 25;1001:78-85. doi: 10.1016/j.aca.2017.11.019. Epub 2017 Nov 14. [PubMed:29291809 ]

Enzymes

Enzyme Details

1. DNA (cytosine-5)-methyltransferase 1

General function:: Replication, recombination and repair
Specific function:: Methylates CpG residues. Preferentially methylates hemimethylated DNA. Associates with DNA replication sites in S phase maintaining the methylation pattern in the newly synthesized strand, that is essential for epigenetic inheritance. Associates with chromatin during G2 and M phases to maintain DNA methylation independently of replication. It is responsible for maintaining methylation patterns established in development. DNA methylation is coordinated with methylation of histones. Mediates transcriptional repression by direct binding to HDAC2. In association with DNMT3B and via the recruitment of CTCFL/BORIS, involved in activation of BAG1 gene expression by modulating dimethylation of promoter histone H3 at H3K4 and H3K9. Probably forms a corepressor complex required for activated KRAS-mediated promoter hypermethylation and transcriptional silencing of tumor suppressor genes (TSGs) or other tumor-related genes in colorectal cancer (CRC) cells. Also required to maintain a transcriptionally repressive state of genes in undifferentiated embryonic stem cells (ESCs). Associates at promoter regions of tumor suppressor genes (TSGs) leading to their gene silencing. Promotes tumor growth.
Gene Name:: DNMT1
Uniprot ID:: Q24K09
Molecular weight:: 182842.0

Reactions

S-Adenosylmethionine + Glycine → S-Adenosylhomocysteine + Sarcosine	details

Enzyme Details

2. Peroxisomal sarcosine oxidase

General function:: Amino acid transport and metabolism
Specific function:: Metabolizes sarcosine, L-pipecolic acid and L-proline.
Gene Name:: PIPOX
Uniprot ID:: Q29RU9
Molecular weight:: 43820.0

Enzyme Details

3. Pyruvate dehydrogenase phosphatase regulatory subunit, mitochondrial

General function:: Not Available
Specific function:: Decreases the sensitivity of PDP1 to magnesium ions, and this inhibition is reversed by the polyamine spermine.
Gene Name:: PDPR
Uniprot ID:: O46504
Molecular weight:: 98857.0

Reactions

Dimethylglycine + Water → Formaldehyde + Sarcosine	details
Sarcosine + Water → Formaldehyde + Glycine	details

Showing metabocard for Sarcosine (BMDB0000271)

Structure for BMDB0000271 (Sarcosine)

Enzymes

Reactions

Reactions