Ethionine

Ethionine

IUPAC name 2-Amino-4-ethylsulfanylbutyric acid
Other names S-Ethyl-L-homocysteine
Identifiers
CAS number	13073-35-3^Y
PubChem	6205
ChemSpider	5970^Y
ChEMBL	CHEMBL203187^N
Jmol-3D images	Image 1
SMILES O=C(O)C(N)CCSCC
InChI InChI=1S/C6H13NO2S/c1-2-10-4-3-5(7)6(8)9/h5H,2-4,7H2,1H3,(H,8,9)^Y Key: GGLZPLKKBSSKCX-UHFFFAOYSA-N^Y InChI=1/C6H13NO2S/c1-2-10-4-3-5(7)6(8)9/h5H,2-4,7H2,1H3,(H,8,9) Key: GGLZPLKKBSSKCX-UHFFFAOYAB
Properties
Molecular formula	C₆H₁₃NO₂S
Molar mass	163.239 g/mol
N (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Ethionine is a non-proteinogenic amino acid structurally related to methionine, with an ethyl group in place of the methyl group.

Ethionine is an antimetabolite and methionine antagonist. It prevents amino acid incorporation into proteins and interferes with cellular use of adenosine triphosphate (ATP). Because of these pharmacological effects, ethionine is highly toxic and is a potent carcinogen.^[1]

References

^ Narayan Shivapurkar, Mary J. Wilson and Lionel A. Poirier (1984). "Hypomethylation of DNA in ethionine-fed rats". Carcinogensis 5 (8): 989–992. doi:10.1093/carcin/5.8.989. PMID 6744518.