| Record Information |
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| Version | 1.0 |
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| Creation Date | 2016-09-30 22:33:02 UTC |
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| Update Date | 2020-05-21 16:29:27 UTC |
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| BMDB ID | BMDB0000574 |
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| Secondary Accession Numbers | |
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| Metabolite Identification |
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| Common Name | L-Cysteine |
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| Description | L-Cysteine, also known as C or e 920, 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. L-Cysteine is a drug which is used for the prevention of liver damage and kidney damage associated with overdoses of acetaminophen. L-Cysteine exists as a solid, possibly soluble (in water), and a very strong basic compound (based on its pKa) molecule. L-Cysteine exists in all living species, ranging from bacteria to humans. L-Cysteine participates in a number of enzymatic reactions, within cattle. In particular, L-Cysteine can be converted into 3-sulfinoalanine through its interaction with the enzyme cysteine dioxygenase type 1. In addition, L-Cysteine can be converted into hydrogen sulfide and pyruvic acid through its interaction with the enzyme cystathionine gamma-lyase. In cattle, L-cysteine is involved in the metabolic pathway called the cysteine metabolism pathway. L-Cysteine is a potentially toxic compound. |
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| Structure | |
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| Synonyms | | Value | Source |
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| (2R)-2-Amino-3-mercaptopropanoic acid | ChEBI | | (2R)-2-Amino-3-sulfanylpropanoic acid | ChEBI | | (R)-2-Amino-3-mercaptopropanoic acid | ChEBI | | C | ChEBI | | Cys | ChEBI | | CYSTEINE | ChEBI | | e 920 | ChEBI | | e-920 | ChEBI | | e920 | ChEBI | | FREE cysteine | ChEBI | | L-2-Amino-3-mercaptopropionic acid | ChEBI | | L-Cystein | ChEBI | | L-Zystein | ChEBI | | Ecolan | Kegg | | (2R)-2-Amino-3-mercaptopropanoate | Generator | | (2R)-2-Amino-3-sulfanylpropanoate | Generator | | (2R)-2-Amino-3-sulphanylpropanoate | Generator | | (2R)-2-Amino-3-sulphanylpropanoic acid | Generator | | (R)-2-Amino-3-mercaptopropanoate | Generator | | L-2-Amino-3-mercaptopropionate | Generator | | (+)-2-Amino-3-mercaptopropionic acid | HMDB | | (R)-(+)-Cysteine | HMDB | | (R)-2-Amino-3-mercapto-propanoate | HMDB | | (R)-2-Amino-3-mercapto-propanoic acid | HMDB | | (R)-Cysteine | HMDB | | 2-Amino-3-mercaptopropanoate | HMDB | | 2-Amino-3-mercaptopropanoic acid | HMDB | | 2-Amino-3-mercaptopropionate | HMDB | | 2-Amino-3-mercaptopropionic acid | HMDB | | 3-Mercapto-L-alanine | HMDB | | Acetylcysteine | HMDB | | alpha-Amino-beta-thiolpropionic acid | HMDB | | b-Mercaptoalanine | HMDB | | beta-Mercaptoalanine | HMDB | | Carbocysteine | HMDB | | Cisteina | HMDB | | Cisteinum | HMDB | | Cystein | HMDB | | Cysteinum | HMDB | | Half-cystine | HMDB | | L Cysteine | HMDB | | L-(+)-Cysteine | HMDB | | L-2-Amino-3-mercaptopropanoate | HMDB | | L-2-Amino-3-mercaptopropanoic acid | HMDB | | Polycysteine | HMDB | | Thioserine | HMDB | | Cysteine hydrochloride | HMDB | | Zinc cysteinate | HMDB | | Half cystine | HMDB |
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| Chemical Formula | C3H7NO2S |
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| Average Molecular Weight | 121.158 |
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| Monoisotopic Molecular Weight | 121.019749163 |
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| IUPAC Name | (2R)-2-amino-3-sulfanylpropanoic acid |
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| Traditional Name | L-cysteine |
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| CAS Registry Number | 52-90-4 |
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| SMILES | N[C@@H](CS)C(O)=O |
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| InChI Identifier | InChI=1S/C3H7NO2S/c4-2(1-7)3(5)6/h2,7H,1,4H2,(H,5,6)/t2-/m0/s1 |
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| InChI Key | XUJNEKJLAYXESH-REOHCLBHSA-N |
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| Chemical Taxonomy |
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| 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. |
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| Kingdom | Organic compounds |
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| Super Class | Organic acids and derivatives |
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| Class | Carboxylic acids and derivatives |
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| Sub Class | Amino acids, peptides, and analogues |
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| Direct Parent | Cysteine and derivatives |
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| Alternative Parents | |
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| Substituents | - Cysteine or derivatives
- Alpha-amino acid
- L-alpha-amino acid
- Amino acid
- Alkylthiol
- Carboxylic acid
- Monocarboxylic acid or derivatives
- Organic oxygen compound
- Primary amine
- Organosulfur compound
- Organooxygen compound
- Organonitrogen compound
- Organic nitrogen compound
- Primary aliphatic amine
- Carbonyl group
- Amine
- Hydrocarbon derivative
- Organopnictogen compound
- Organic oxide
- Aliphatic acyclic compound
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| Molecular Framework | Aliphatic acyclic compounds |
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| External Descriptors | |
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| Ontology |
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| Status | Detected but not Quantified |
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| Origin | |
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| Biofunction | Not Available |
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| Application | Not Available |
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| Cellular locations | - Cytoplasm
- Mitochondria
- Myelin sheath
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| Physical Properties |
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| State | Solid |
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| Experimental Properties | | Property | Value | Reference |
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| Melting Point | 220 °C | Not Available | | Boiling Point | Not Available | Not Available | | Water Solubility | 277 mg/mL at 25 °C | BEILSTEIN | | LogP | -2.49 | HANSCH,C ET AL. (1995) |
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| Predicted Properties | |
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| Spectra |
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| Spectra | |
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| Biological Properties |
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| Cellular Locations | - Cytoplasm
- Mitochondria
- Myelin sheath
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| Biospecimen Locations | - Adrenal Cortex
- Epidermis
- Fibroblasts
- Intestine
- Kidney
- Liver
- Mammary Gland
- Milk
- Neuron
- Placenta
- Platelet
- Prostate Tissue
- Skeletal Muscle
- Spleen
- Testis
- Thyroid Gland
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| Pathways | |
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| Normal Concentrations |
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| Adrenal Cortex | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Epidermis | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Fibroblasts | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Intestine | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Kidney | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Liver | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Liver | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Liver | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Mammary Gland | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Mammary Gland | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Milk | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Neuron | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Placenta | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Platelet | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Prostate Tissue | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Skeletal Muscle | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Spleen | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Testis | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Thyroid Gland | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details |
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| Abnormal Concentrations |
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| Not Available |
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| External Links |
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| HMDB ID | HMDB0000574 |
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| DrugBank ID | DB00151 |
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| Phenol Explorer Compound ID | Not Available |
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| FooDB ID | FDB012678 |
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| KNApSAcK ID | C00001351 |
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| Chemspider ID | 5653 |
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| KEGG Compound ID | C00097 |
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| BioCyc ID | CYS |
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| BiGG ID | 33843 |
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| Wikipedia Link | Cysteine |
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| METLIN ID | 5556 |
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| PubChem Compound | 5862 |
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| PDB ID | Not Available |
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| ChEBI ID | 17561 |
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| References |
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| Synthesis Reference | Kumagai, Hidehiko; Tanaka, Hideyuki; Sejima, Shunsuke; Yamada, Hideaki. Elimination and replacement reactions of b-chloro-L-alanine by cysteine desulfhydrase from Aerobacter aerogenes. Agricultural and Biological Chemistry (1977), 41(10), 2071-5. |
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| Material Safety Data Sheet (MSDS) | Not Available |
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| General References | - Pan L, Yu J, Mi Z, Mo L, Jin H, Yao C, Ren D, Menghe B: A Metabolomics Approach Uncovers Differences between Traditional and Commercial Dairy Products in Buryatia (Russian Federation). Molecules. 2018 Mar 22;23(4). pii: molecules23040735. doi: 10.3390/molecules23040735. [PubMed:29565828 ]
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