Sarcosine
(right click,save link as to download,it is a temp file,please download as soon as possible, you can also use CTRL+S to save the whole html page)
Basic Info
| Common Name | Sarcosine(F05384) |
| 2D Structure | |
| 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 (A3519). |
| FRCD ID | F05384 |
| CAS Number | 107-97-1 |
| PubChem CID | 1088 |
| Formula | C3H7NO2 |
| IUPAC Name | 2-(methylamino)acetic acid |
| InChI Key | FSYKKLYZXJSNPZ-UHFFFAOYSA-N |
| InChI | InChI=1S/C3H7NO2/c1-4-2-3(5)6/h4H,2H2,1H3,(H,5,6) |
| Canonical SMILES | CNCC(=O)O |
| Isomeric SMILES | CNCC(=O)O |
| Wikipedia | Sarcosine |
| Synonyms |
Sarcosinic acid
sarcosine
N-methylglycine
107-97-1
Methylglycine
Glycine, N-methyl-
N-Methylaminoacetic acid
Sarcosin
2-(methylamino)acetic acid
Methylaminoacetic acid
|
| Classifies |
Animal Toxin
|
| Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
| Kingdom | Organic compounds |
| Superclass | Organic acids and derivatives |
| Class | Carboxylic acids and derivatives |
| Subclass | Amino acids, peptides, and analogues |
| Intermediate Tree Nodes | Amino acids and derivatives - Alpha amino acids and derivatives |
| Direct Parent | Alpha amino acids |
| Alternative Parents | |
| Molecular Framework | Aliphatic acyclic compounds |
| 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 |
| Description | This compound 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). |
Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 89.094 |
| Hydrogen Bond Donor Count | 2 |
| Hydrogen Bond Acceptor Count | 3 |
| Rotatable Bond Count | 2 |
| Complexity | 52.8 |
| Monoisotopic Mass | 89.048 |
| Exact Mass | 89.048 |
| XLogP | -2.8 |
| Formal Charge | 0 |
| Heavy Atom Count | 6 |
| Defined Atom Stereocenter Count | 0 |
| Undefined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| Isotope Atom Count | 0 |
| Covalently-Bonded Unit Count | 1 |
ADMET
| Model | Result | Probability |
|---|---|---|
| Absorption | ||
| Blood-Brain Barrier | BBB+ | 0.6472 |
| Human Intestinal Absorption | HIA+ | 0.9639 |
| Caco-2 Permeability | Caco2- | 0.6885 |
| P-glycoprotein Substrate | Non-substrate | 0.6168 |
| P-glycoprotein Inhibitor | Non-inhibitor | 0.9641 |
| Non-inhibitor | 0.9601 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.9368 |
| Distribution | ||
| Subcellular localization | Lysosome | 0.6161 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.8096 |
| CYP450 2D6 Substrate | Non-substrate | 0.8493 |
| CYP450 3A4 Substrate | Non-substrate | 0.7701 |
| CYP450 1A2 Inhibitor | Non-inhibitor | 0.9394 |
| CYP450 2C9 Inhibitor | Non-inhibitor | 0.9667 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.9675 |
| CYP450 2C19 Inhibitor | Non-inhibitor | 0.9650 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.9724 |
| CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.9937 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.8920 |
| Non-inhibitor | 0.9554 | |
| AMES Toxicity | Non AMES toxic | 0.9577 |
| Carcinogens | Non-carcinogens | 0.7395 |
| Fish Toxicity | Low FHMT | 0.7890 |
| Tetrahymena Pyriformis Toxicity | Low TPT | 0.9875 |
| Honey Bee Toxicity | Low HBT | 0.5847 |
| Biodegradation | Ready biodegradable | 0.9503 |
| Acute Oral Toxicity | III | 0.7123 |
| Carcinogenicity (Three-class) | Non-required | 0.6840 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | 0.9316 | LogS |
| Caco-2 Permeability | 0.5510 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 1.5219 | LD50, mol/kg |
| Fish Toxicity | 3.1744 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | -1.7202 | pIGC50, ug/L |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| Food safety using NMR-based metabolomics: Assessment of the Atlantic bluefintuna, Thunnus thynnus, from the Mediterranean Sea. | Food Chem Toxicol | 2018 May | 29601848 |
| Cadmium toxicity induced contrasting patterns of concentrations of freesarcosine, specific amino acids and selected microelements in two Noccaeaspecies. | PLoS One | 2017 May 19 | 28542385 |
| Most blood biomarkers related to vitamin status, one-carbon metabolism, and thekynurenine pathway show adequate preanalytical stability and within-personreproducibility to allow assessment of exposure or nutritional status in healthy women and cardiovascular patients. | J Nutr | 2014 May | 24647388 |
| Permeabilization of Kluyveromyces marxianus with mild detergent for whey lactose hydrolysis and augmentation of mixed culture. | Appl Biochem Biotechnol | 2014 Mar | 24500798 |
| Comparative study of the use of sarcosine, proline and glycine as acrylamideinhibitors in ripe olive processing. | Food Addit Contam Part A Chem Anal Control Expo Risk Assess | 2014 | 24294998 |
| Effects of carbohydrates on the oNPG converting activity of β-galactosidases. | J Agric Food Chem | 2013 Jul 3 | 23725091 |
| Permeabilization of baker's yeast with N-lauroyl sarcosine. | J Ind Microbiol Biotechnol | 2008 Aug | 18415131 |
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
References
- 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
- 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 ]