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Record Information
Created at2005-11-16 15:48:42 UTC
Updated at2021-08-09 22:32:43 UTC
NP-MRD IDNP0000120
Secondary Accession NumbersNone
Natural Product Identification
Common NameL-Cysteine
DescriptionCysteine (Cys), also known as L-cysteine is an alpha-amino acid. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon). Amino acids are organic compounds that contain amino (–NH2) and carboxyl (–COOH) functional groups, along with a side chain (R group) specific to each amino acid. L-alanine is one of 20 proteinogenic amino acids, i.E., The amino acids used in the biosynthesis of proteins. Cysteine is found in all organisms ranging from bacteria to plants to animals. It is classified as an aliphatic, non-polar, sulfur-containing amino acid. Cysteine is an important source of sulfur in human metabolism, and although it is classified as a non-essential amino acid, cysteine may be essential for infants, the elderly, and individuals with certain metabolic disease or who suffer from malabsorption syndromes. Cysteine can occasionally be considered as an essential or conditionally essential amino acid. Cysteine is unique amongst the twenty natural amino acids as it contains a thiol group. Thiol groups can undergo oxidation/reduction (redox) reactions; when cysteine is oxidized it can form cystine, which is two cysteine residues joined by a disulfide bond. This reaction is reversible since the reduction of this disulphide bond regenerates two cysteine molecules. The disulphide bonds of cystine are crucial to defining the structures of many proteins. Cysteine is often involved in electron-transfer reactions, and help the enzyme catalyze its reaction. Cysteine is also part of the antioxidant glutathione. N-Acetyl-L-cysteine (NAC) is a form of cysteine where an acetyl group is attached to cysteine's nitrogen atom and is sold as a dietary supplement. Cysteine is named after cystine, which comes from the Greek word kustis meaning bladder (cystine was first isolated from kidney stones). Oxidation of cysteine can produce a disulfide bond with another thiol and further oxidation can produce sulphfinic or sulfonic acids. The cysteine thiol group is also a nucleophile and can undergo addition and substitution reactions. Thiol groups become much more reactive when they are ionized, and cysteine residues in proteins have pKa values close to neutrality, so they are often in their reactive thiolate form in the cell. The thiol group also has a high affinity for heavy metals and proteins containing cysteine will bind metals such as mercury, lead, and cadmium tightly. Due to this ability to undergo redox reactions, cysteine has antioxidant properties. Cysteine is important in energy metabolism. As cystine, it is a structural component of many tissues and hormones. Cysteine has clinical uses ranging from treating baldness to psoriasis to preventing smoker's hack. In some cases, oral cysteine therapy has proved excellent for treatment of asthmatics, enabling them to stop theophylline and other medications. Cysteine also enhances the effect of topically applied silver, tin, and zinc salts in preventing dental cavities. In the future, cysteine may play a role in the treatment of cobalt toxicity, diabetes, psychosis, cancer, and seizures (http://Www.Dcnutrition.Com/AminoAcids/). Cysteine has been identified as a uremic toxin according to the European Uremic Toxin Working Group (PMID: 22626821 ).
(2R)-2-Amino-3-mercaptopropanoic acidChEBI
(2R)-2-Amino-3-sulfanylpropanoic acidChEBI
(R)-2-Amino-3-mercaptopropanoic acidChEBI
e 920ChEBI
FREE cysteineChEBI
L-2-Amino-3-mercaptopropionic acidChEBI
(2R)-2-Amino-3-sulphanylpropanoic acidGenerator
(+)-2-Amino-3-mercaptopropionic acidHMDB
(R)-2-Amino-3-mercapto-propanoic acidHMDB
2-Amino-3-mercaptopropanoic acidHMDB
2-Amino-3-mercaptopropionic acidHMDB
alpha-Amino-beta-thiolpropionic acidHMDB
L CysteineHMDB
L-2-Amino-3-mercaptopropanoic acidHMDB
Cysteine hydrochlorideHMDB
Zinc cysteinateHMDB
Half cystineHMDB
Chemical FormulaC3H7NO2S
Average Mass121.1580 Da
Monoisotopic Mass121.01975 Da
IUPAC Name(2R)-2-amino-3-sulfanylpropanoic acid
Traditional NameL-cysteine
CAS Registry Number52-90-4
InChI Identifier
Spectrum TypeDescriptionDepositor IDDeposition DateView
1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, experimental)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, D2O, experimental)Wishart Lab2021-06-20View Spectrum
2D NMR[1H, 1H] 2D NMR Spectrum (experimental)Wishart Lab2021-06-20View Spectrum
2D NMR[1H, 13C] NMR Spectrum (2D, 600 MHz, H2O, experimental)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, simulated)V.dorna832021-07-25View Spectrum
Species of Origin
  • All
  • 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.
    KingdomOrganic compounds
    Super ClassOrganic acids and derivatives
    ClassCarboxylic acids and derivatives
    Sub ClassAmino acids, peptides, and analogues
    Direct ParentCysteine and derivatives
    Alternative Parents
    • 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
    Molecular FrameworkAliphatic acyclic compounds
    External Descriptors
    Physical Properties
    Experimental Properties
    Melting Point220 °CNot Available
    Boiling PointNot AvailableNot Available
    Water Solubility277 mg/mL at 25 °CBEILSTEIN
    LogP-2.49HANSCH,C ET AL. (1995)
    Predicted Properties
    Water Solubility23.1 g/LALOGPS
    pKa (Strongest Acidic)2.35ChemAxon
    pKa (Strongest Basic)9.05ChemAxon
    Physiological Charge0ChemAxon
    Hydrogen Acceptor Count3ChemAxon
    Hydrogen Donor Count3ChemAxon
    Polar Surface Area63.32 ŲChemAxon
    Rotatable Bond Count2ChemAxon
    Refractivity28.22 m³·mol⁻¹ChemAxon
    Polarizability11.41 ųChemAxon
    Number of Rings0ChemAxon
    Rule of FiveYesChemAxon
    Ghose FilterNoChemAxon
    Veber's RuleNoChemAxon
    MDDR-like RuleNoChemAxon
    External Links
    HMDB IDHMDB0000574
    DrugBank IDDB00151
    Phenol Explorer Compound IDNot Available
    FoodDB IDFDB012678
    KNApSAcK IDC00001351
    Chemspider ID5653
    KEGG Compound IDC00097
    BioCyc IDCYS
    BiGG ID33843
    Wikipedia LinkCysteine
    METLIN ID5556
    PubChem Compound5862
    PDB IDNot Available
    ChEBI ID17561
    Good Scents IDNot Available
    General References
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