You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information |
---|
Version | 4.0 |
---|
Status | Detected and Quantified |
---|
Creation Date | 2006-05-22 14:17:36 UTC |
---|
Update Date | 2020-02-26 21:23:49 UTC |
---|
HMDB ID | HMDB0002108 |
---|
Secondary Accession Numbers | |
---|
Metabolite Identification |
---|
Common Name | Methylcysteine |
---|
Description | Methylcysteine is one of the identified number of bioactive substances in garlic that are water soluble. (PMID 16484549 ). It has been suggested that the use of these organosulfur agents derived from garlic could protect partially oxidized and glycated LDL or plasma against further oxidative and glycative deterioration, which might benefit patients with diabetic-related vascular diseases. (PMID 15161248 ). It may also exert some chemopreventive effects on chemical carcinogenesis. However, it should be borne in mind that may also demonstrate promotion potential, depending on the organ examined. (PMID 9591199 ). Methylcystein is a biomarker for the consumption of dried and cooked beans |
---|
Structure | |
---|
Synonyms | Value | Source |
---|
(2R)-2-Amino-3-(methylsulfanyl)propanoic acid | HMDB | (R)-2-Amino-3-(methylthio)propanoic acid | HMDB | 3-(Methylthio)-L-alanine | HMDB | L-Methylcysteine | HMDB | S-Methyl-L-cysteine | HMDB | (2R)-2-Amino-3-(methylsulfanyl)propanoate | HMDB | (2R)-2-Amino-3-(methylsulphanyl)propanoate | HMDB | (2R)-2-Amino-3-(methylsulphanyl)propanoic acid | HMDB | (R)-2-Amino-3-(methylthio)propanoate | HMDB | 3-(Methylthio)-L-(8ci)alanine | HMDB | Acm-thiopropionate | HMDB | Acm-thiopropionic acid | HMDB | L-Aspartic acid dimethyl ester | HMDB | S-Acetamidomethyl-deamino-cysteine | HMDB | S-Methyl-(9ci)-L-cysteine | HMDB | S-Methyl-cysteine | HMDB | S-Methyl-DL-cysteine | HMDB | S-Methylcysteine | HMDB | S-11C-Methyl-L-cysteine | HMDB | S-Methylcysteine, (DL-cys)-isomer | HMDB | S-Methylcysteine, hydrochloride, (L-cys)-isomer | HMDB | S-Methylcysteine, (L-cys)-isomer | HMDB |
|
---|
Chemical Formula | C4H9NO2S |
---|
Average Molecular Weight | 135.18 |
---|
Monoisotopic Molecular Weight | 135.035399708 |
---|
IUPAC Name | (2S)-2-amino-3-(methylsulfanyl)propanoic acid |
---|
Traditional Name | (2S)-2-amino-3-(methylsulfanyl)propanoic acid |
---|
CAS Registry Number | 1187-84-4 |
---|
SMILES | CSC[C@@H](N)C(O)=O |
---|
InChI Identifier | InChI=1S/C4H9NO2S/c1-8-2-3(5)4(6)7/h3H,2,5H2,1H3,(H,6,7)/t3-/m1/s1 |
---|
InChI Key | IDIDJDIHTAOVLG-GSVOUGTGSA-N |
---|
Chemical Taxonomy |
---|
Description | belongs to the class of organic compounds known as cysteine and derivatives. Cysteine and derivatives are compounds containing cysteine or a derivative thereof resulting from reaction of cysteine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. |
---|
Kingdom | Organic compounds |
---|
Super Class | Organic acids and derivatives |
---|
Class | Carboxylic acids and derivatives |
---|
Sub Class | Amino acids, peptides, and analogues |
---|
Direct Parent | Cysteine and derivatives |
---|
Alternative Parents | |
---|
Substituents | - Cysteine or derivatives
- S-alkyl-l-cysteine
- Alpha-amino acid
- D-alpha-amino acid
- Amino acid
- Carboxylic acid
- Monocarboxylic acid or derivatives
- Thioether
- Sulfenyl compound
- Dialkylthioether
- Organic nitrogen compound
- Hydrocarbon derivative
- Organic oxide
- Primary amine
- Organosulfur compound
- Organooxygen compound
- Organonitrogen compound
- Organopnictogen compound
- Primary aliphatic amine
- Organic oxygen compound
- Carbonyl group
- Amine
- Aliphatic acyclic compound
|
---|
Molecular Framework | Aliphatic acyclic compounds |
---|
External Descriptors | Not Available |
---|
Ontology |
---|
|
Disposition | Route of exposure: Biological location: Source: |
---|
Role | Industrial application: |
---|
Physical Properties |
---|
State | Solid |
---|
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 | |
---|
Spectra |
---|
| Not Available |
---|
Biological Properties |
---|
Cellular Locations | Not Available |
---|
Biospecimen Locations | |
---|
Tissue Locations | |
---|
Pathways | |
---|
Normal Concentrations |
---|
| |
Blood | Detected and Quantified | 3.9 +/- 1.9 uM | Adult (>18 years old) | Both | Normal | | details | Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Normal | | details | Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Normal | | details | Urine | Detected and Quantified | 0.34-0.82 umol/mmol creatinine | Adult (>18 years old) | Female | Normal | | details | Urine | Detected and Quantified | 0.35-0.63 umol/mmol creatinine | Adult (>18 years old) | Male | Normal | | details | Urine | Detected and Quantified | 0.0796-0.717 umol/mmol creatinine | Adult (>18 years old) | Male | Normal | | details | Urine | Detected and Quantified | 0.0177-0.619 umol/mmol creatinine | Adult (>18 years old) | Female | Normal | | details | Urine | Detected and Quantified | 0.34-0.82 umol/mmol creatinine | Adult (>18 years old) | Female | Normal | | details | Urine | Detected and Quantified | 0.35-0.63 umol/mmol creatinine | Adult (>18 years old) | Male | Normal | | details |
|
---|
Abnormal Concentrations |
---|
| Not Available |
---|
Associated Disorders and Diseases |
---|
Disease References | None |
---|
Associated OMIM IDs | None |
---|
External Links |
---|
DrugBank ID | Not Available |
---|
Phenol Explorer Compound ID | Not Available |
---|
FooDB ID | FDB003689 |
---|
KNApSAcK ID | Not Available |
---|
Chemspider ID | 22826 |
---|
KEGG Compound ID | Not Available |
---|
BioCyc ID | S-METHYL-L-CYSTEINE |
---|
BiGG ID | Not Available |
---|
Wikipedia Link | Not Available |
---|
METLIN ID | 6490 |
---|
PubChem Compound | 24417 |
---|
PDB ID | Not Available |
---|
ChEBI ID | 45658 |
---|
Food Biomarker Ontology | Not Available |
---|
VMH ID | Not Available |
---|
MarkerDB ID | |
---|
References |
---|
Synthesis Reference | Ma, Chengjun; Yao, Fei; Zhang, Guanyong. Synthesis of S-methyl-L-cysteine. Huaxue Shijie (2003), 44(7), 370-372. |
---|
Material Safety Data Sheet (MSDS) | Download (PDF) |
---|
General References | - Rivlin RS: Is garlic alternative medicine? J Nutr. 2006 Mar;136(3 Suppl):713S-715S. [PubMed:16484549 ]
- Huang CN, Horng JS, Yin MC: Antioxidative and antiglycative effects of six organosulfur compounds in low-density lipoprotein and plasma. J Agric Food Chem. 2004 Jun 2;52(11):3674-8. [PubMed:15161248 ]
- Fukushima S, Takada N, Hori T, Wanibuchi H: Cancer prevention by organosulfur compounds from garlic and onion. J Cell Biochem Suppl. 1997;27:100-5. [PubMed:9591199 ]
- Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]
|
---|