S-(2-Aminoethyl)-L-cysteine
Basic information
- CAS
2936-69-8- Standard SMILES
NCCSC[C@H](N)C(=O)O- InChIKey
GHSJKUNUIHUPDF-BYPYZUCNSA-N- Molecular formula
- C5H12N2O2S
- Average molar mass
- 164.23 g/mol
- Monoisotopic mass
- 164.0619488
Overview
L-thialysine is a cysteine derivative that is the S-(2-aminoethyl) analogue of L-cysteine; reported to have cytotoxic effects. It has a role as a metabolite, a protein synthesis inhibitor and an EC 5.4.3.2 (lysine 2,3-aminomutase) inhibitor. It is a L-cysteine thioether and a non-proteinogenic L-alpha-amino acid. It is a conjugate base of a L-thialysinium.
Names & identifiers
- Preferred name
- S-(2-Aminoethyl)-L-cysteine
- IUPAC
- (2R)-2-amino-3-(2-aminoethylsulfanyl)propanoic acid
- English name
- L-Cysteine, S-(2-aminoethyl)- (9CI)
- Molecular formula
- C5H12N2O2S
- Molecular weight
- 164.23
Names & synonyms
S-(2-Aminoethyl)-L-cysteineThiosine2936-69-8gamma-Thialysinegamma-Thia-lysAminoethylcysteineS-2-Aminoethyl cysteineS-beta-Aminoethyl cysteineOS2H9OH0GTDTXSID40183588RefChem:884174DTXCID80106079
Show more names
Nsc241277L-4-Thialysine3-[(2-Aminoethyl)thio]-L-alanineL-Cysteine, S-(2-aminoethyl)- (9CI)
L-Thialysine4-thialysine4-thia-L-lysineL-Cysteine, S-(2-aminoethyl)-(2R)-2-amino-3-(2-aminoethylsulfanyl)propanoic acid(2R)-2-amino-3-[(2-aminoethyl)sulfanyl]propanoic acidCHEMBL397565(R)-2-amino-3-(2-aminoethylthio)propanoic acid
Database identifiers
- CAS
2936-69-8- PubChem CID
- 99558
- DTXSID
DTXSID40183588- ChEMBL
CHEMBL397565- ChEBI
CHEBI:497734- UNII
- OS2H9OH0GT
Properties
Computed structural properties
- XLogP
- -3.7
- Topological polar surface area
- 115 Ų
- Hydrogen bond donors
- 3
- Hydrogen bond acceptors
- 5
- Rotatable bonds
- 5
- Heavy atoms
- 10
- Formal charge
- 0
- Complexity
- 110
Experimental & physicochemical properties
Chemical ClassesBiological Agents -> Amino Acids and Derivatives
Physical DescriptionSolid
Physicochemical properties
- Boiling point
- 341.1 · 341.1±42.0 °C(Predicted)
- Density
- 1.289 · 1.289±0.06 g/cm3(Predicted)
- pka
- 2.02 · 2.02±0.10(Predicted)
- FDA UNII
- 2 H9OH0GT · OS2H9OH0GT
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Hazard information
Hazards SummaryInhibits protein synthesis in mammalian cells. [ChemIDplus] See Cysteine.
Chemistry & industry
Pharmacology
MeSH Pharmacological Classification
Compounds which inhibit the synthesis of proteins. They are usually ANTI-BACTERIAL AGENTS or toxins. Mechanism of the action of inhibition includes the interruption of peptide-chain elongation, the blocking the A site of ribosomes, the misreading of the genetic code or the prevention of the attachment of oligosaccharide side chains to glycoproteins.
Additional notes
DefinitionChEBI: A cysteine derivative that is the S-(2-aminoethyl) analogue of L-cysteine; reported to have cytotoxic effects.
Related reactions
6 records
Compound notes
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