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| Name | L-Cysteine | ||||||||||||||||||||||||||||||||||||||||||
| Accession Number | DB00151 (DB04443, NUTR00018) | ||||||||||||||||||||||||||||||||||||||||||
| Type | small molecule | ||||||||||||||||||||||||||||||||||||||||||
| Groups | approved, nutraceutical | ||||||||||||||||||||||||||||||||||||||||||
| Description | A thiol-containing non-essential amino acid that is oxidized to form cystine. [PubChem] |
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| Structure |
Download: MOL | SDF | SMILES | InChI Display: 2D Structure | 3D Structure |
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| Synonyms |
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| Salts | Not Available | ||||||||||||||||||||||||||||||||||||||||||
| Brand names | Not Available | ||||||||||||||||||||||||||||||||||||||||||
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| Categories |
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| CAS number | 52-90-4 | ||||||||||||||||||||||||||||||||||||||||||
| Weight |
Average: 121.158 Monoisotopic: 121.019749163 |
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| Chemical Formula | C3H7NO2S | ||||||||||||||||||||||||||||||||||||||||||
| InChI Key | InChIKey=XUJNEKJLAYXESH-REOHCLBHSA-N | ||||||||||||||||||||||||||||||||||||||||||
| InChI |
InChI=1S/C3H7NO2S/c4-2(1-7)3(5)6/h2,7H,1,4H2,(H,5,6)/t2-/m0/s1
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| IUPAC Name |
(2R)-2-amino-3-sulfanylpropanoic acid
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| SMILES |
N[C@@H](CS)C(O)=O
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| Mass Spec | show (8.4 KB) | ||||||||||||||||||||||||||||||||||||||||||
| Taxonomy | |||||||||||||||||||||||||||||||||||||||||||
| Kingdom | Organic | ||||||||||||||||||||||||||||||||||||||||||
| Classes |
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| Substructures |
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| Pharmacology | |||||||||||||||||||||||||||||||||||||||||||
| Indication | For the prevention of liver damage and kidney damage associated with overdoses of acetaminophen | ||||||||||||||||||||||||||||||||||||||||||
| Pharmacodynamics | Due to this ability to undergo redox reactions, cysteine has antioxidant properties. 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 may at some point be recognized as an essential or conditionally essential amino acid. | ||||||||||||||||||||||||||||||||||||||||||
| Mechanism of action | Although 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 usually be synthesized by the human body under normal physiological conditions if a sufficient quantity of methionine is available. Due to the ability of thiols to undergo redox reactions, cysteine has antioxidant properties. Cysteine's antioxidant properties are typically expressed in the tripeptide glutathione, which occurs in humans as well as other organisms. The systemic availability of oral glutathione (GSH) is negligible; so it must be biosynthesized from its constituent amino acids, cysteine, glycine, and glutamic acid. Glutamic acid and glycine are readily available in the diets of most industrialized countries, but the availability of cysteine can be the limiting substrate. Cysteine is also an important source of sulfide in human metabolism. The sulfide in iron-sulfur clusters and in nitrogenase is extracted from cysteine, which is converted to alanine in the process. In a 1994 report released by five top cigarette companies, cysteine is one of the 599 additives to cigarettes. Its use or purpose, however, is unknown, like most cigarette additives. Its inclusion in cigarettes could offer two benefits: Acting as an expectorant, since smoking increases mucus production in the lungs; and increasing the beneficial antioxidant glutathione (which is diminished in smokers). | ||||||||||||||||||||||||||||||||||||||||||
| Absorption | Not Available | ||||||||||||||||||||||||||||||||||||||||||
| Volume of distribution | Not Available | ||||||||||||||||||||||||||||||||||||||||||
| Protein binding | Not Available | ||||||||||||||||||||||||||||||||||||||||||
| Metabolism | Not Available | ||||||||||||||||||||||||||||||||||||||||||
| Route of elimination | Not Available | ||||||||||||||||||||||||||||||||||||||||||
| Half life | Not Available | ||||||||||||||||||||||||||||||||||||||||||
| Clearance | Not Available | ||||||||||||||||||||||||||||||||||||||||||
| Toxicity | Not Available | ||||||||||||||||||||||||||||||||||||||||||
| Affected organisms |
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| Pathways | Not Available | ||||||||||||||||||||||||||||||||||||||||||
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| Dosage forms | Not Available | ||||||||||||||||||||||||||||||||||||||||||
| Prices |
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational
purposes only.
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| Patents | Not Available | ||||||||||||||||||||||||||||||||||||||||||
| Properties | |||||||||||||||||||||||||||||||||||||||||||
| State | solid | ||||||||||||||||||||||||||||||||||||||||||
| Experimental Properties |
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| Predicted Properties |
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| Synthesis Reference | Not Available | ||||||||||||||||||||||||||||||||||||||||||
| General Reference |
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| External Links |
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| ATC Codes |
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| AHFS Codes | Not Available | ||||||||||||||||||||||||||||||||||||||||||
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| FDA label | Not Available | ||||||||||||||||||||||||||||||||||||||||||
| MSDS | show (73.2 KB) | ||||||||||||||||||||||||||||||||||||||||||
| Interactions | |||||||||||||||||||||||||||||||||||||||||||
| Drug Interactions | Not Available | ||||||||||||||||||||||||||||||||||||||||||
| Food Interactions | Not Available | ||||||||||||||||||||||||||||||||||||||||||
| Targets |
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1. Glutamate--cysteine ligase regulatory subunit Pharmacological action: unknownOrganism class: human UniProt ID: P48507 ![]() Gene: GCLM ![]() Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report ![]() References:
2. Glutamate--cysteine ligase catalytic subunit Pharmacological action: unknownOrganism class: human UniProt ID: P48506 ![]() Gene: GCLC ![]() Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report ![]() References:
Pharmacological action: unknown
Organism class: human UniProt ID: Q16857 ![]() Gene: CDO-1 Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report ![]() References:
4. Aspartate aminotransferase, cytoplasmic Pharmacological action: unknownOrganism class: human UniProt ID: P17174 ![]() Gene: GOT1 ![]() Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report ![]() References:
Pharmacological action: unknown
Organism class: human UniProt ID: P32929 ![]() Gene: CTH ![]() Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report ![]() References:
6. Cystathionine beta-synthase Pharmacological action: unknownOrganism class: human UniProt ID: P35520 ![]() Gene: CBS ![]() Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report ![]() References:
7. Cysteinyl-tRNA synthetase, cytoplasmic Pharmacological action: unknownOrganism class: human UniProt ID: P49589 ![]() Gene: CARS ![]() Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report ![]() References: 8. Methylated-DNA--protein-cysteine methyltransferase Pharmacological action: unknownInvolved in the cellular defense against the biological effects of O6-methylguanine (O6-MeG) in DNA. Repairs alkylated guanine in DNA by stoichiometrically transferring the alkyl group at the O-6 position to a cysteine residue in the enzyme. This is a suicide reaction:the enzyme is irreversibly inactivated Organism class: humanUniProt ID: P16455 ![]() Gene: MGMT ![]() Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report ![]() References:
Pharmacological action: unknown
Organism class: human UniProt ID: P48637 ![]() Gene: GSS ![]() Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report ![]() References:
Pharmacological action: unknown
Mediates high affinity thiamine uptake, propably via a proton anti-port mechanism. Has no folate transport activity Organism class: humanUniProt ID: Q9BZV2 ![]() Gene: SLC19A3 ![]() Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report ![]() References: 11. Probable cysteinyl-tRNA synthetase, mitochondrial Pharmacological action: unknownATP + L-cysteine + tRNA(Cys) = AMP + diphosphate + L-cysteinyl-tRNA(Cys) Organism class: humanUniProt ID: Q9HA77 ![]() Gene: CARS2 ![]() Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report ![]() References: 12. Cysteine sulfinic acid decarboxylase Pharmacological action: unknownOrganism class: human UniProt ID: Q9Y600 ![]() Gene: CSAD ![]() Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report ![]() References:
13. Cysteine desulfurase, mitochondrial Pharmacological action: unknownCatalyzes the removal of elemental sulfur from cysteine to produce alanine. It supplies the inorganic sulfur for iron- sulfur (Fe-S) clusters Organism class: humanUniProt ID: Q9Y697 ![]() Gene: NFS1 ![]() Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report ![]() References:
14. Cysteine dioxygenase type 1 Pharmacological action: unknownOrganism class: human UniProt ID: Q16878 ![]() Gene: CDO1 ![]() Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report ![]() References:
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| Transporters |
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1. Monocarboxylate transporter 10 Actions: inhibitorSodium-independent transporter that mediates the update of aromatic acid. Can function as a net efflux pathway for aromatic amino acids in the basosolateral epithelial cells (By similarity) UniProt ID: Q8TF71![]() Gene: SLC16A10 ![]() Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report ![]() References:
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