Ethionine: Difference between revisions
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{{expert-subject|chemistry|date=January 2007}} |
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{{importance|date=July 2006}} |
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[[Image:Ethionic acid.png|thumb|right|The chemical structure of ethionic acid.]] |
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| ImageFile = ethionine.png |
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'''Ethionic acid''' is an [[amino acid]] structurally related to [[methionine]]. Its [[IUPAC]] name is 2-amino-4-ethylsulfanylbutyric acid. |
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| ImageSize = |
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| IUPACName = 2-Amino-4-ethylsulfanylbutyric acid |
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| OtherNames = S-Ethyl-L-homocysteine |
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|Section1={{Chembox Identifiers |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 5970 |
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| InChI = 1/C6H13NO2S/c1-2-10-4-3-5(7)6(8)9/h5H,2-4,7H2,1H3,(H,8,9) |
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| InChIKey = GGLZPLKKBSSKCX-UHFFFAOYAB |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI = 1S/C6H13NO2S/c1-2-10-4-3-5(7)6(8)9/h5H,2-4,7H2,1H3,(H,8,9) |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = GGLZPLKKBSSKCX-UHFFFAOYSA-N |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo = 13073-35-3 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = WX1BN24WZT |
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| PubChem = 6205 |
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| ChEBI_Ref = {{ebicite|changed|EBI}} |
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| ChEBI = 4886 |
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| ChEMBL_Ref = {{ebicite|changed|EBI}} |
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| ChEMBL = 203187 |
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| SMILES = O=C(O)C(N)CCSCC |
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}} |
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|Section2={{Chembox Properties |
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| Formula = C<sub>6</sub>H<sub>13</sub>NO<sub>2</sub>S |
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| MolarMass = 163.239 g/mol |
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| Appearance = |
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| Density = |
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| BoilingPt = |
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| Solubility = |
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|Section3={{Chembox Hazards |
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| MainHazards = |
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| FlashPt = |
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| AutoignitionPt = |
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'''Ethionine''' is a [[Proteinogenic amino acid|non-proteinogenic]] [[amino acid]] structurally related to [[methionine]], with an [[ethyl group]] in place of the [[methyl group]]. |
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Ethionine is an [[antimetabolite]] and methionine [[Receptor antagonist|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.<ref>{{cite journal|title=Hypomethylation of DNA in ethionine-fed rats|author=Narayan Shivapurkar, Mary J. Wilson and Lionel A. Poirier |journal=Carcinogenesis|volume =5|issue=8|pages=989–992|year=1984|doi=10.1093/carcin/5.8.989|pmid=6744518}}</ref> |
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==External links== |
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Ethionine has been found to naturally occur in the edible pulp of the [[durian fruit]], and postulated to be a [[biosynthetic]] precursor for [[ethanethiol]] and other strong [[odorants]] found in the fruit.<ref>{{cite journal|title=Identification of an Important Odorant Precursor in Durian: First Evidence of Ethionine in Plants|author=Nadine S. Fischer and Martin Steinhaus |journal=Journal of Agricultural and Food Chemistry|year=2020 |volume=68 |issue=38 |pages=10397–10402 |doi=10.1021/acs.jafc.9b07065|pmid=31825619 |s2cid=209329891 }}</ref> |
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{{ChemicalSources}} |
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==References== |
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{{Reflist}} |
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[[Category:Alpha-Amino acids]] |
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[[Category:Carcinogens]] |
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[[Category:Sulfur amino acids]] |
[[Category:Sulfur amino acids]] |
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[[Category:Thioethers]] |
[[Category:Thioethers]] |
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[[Category:Toxic amino acids]] |
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[[Category:Antimetabolites]] |
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{{amine-stub}} |
{{amine-stub}} |
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Latest revision as of 21:32, 17 September 2023
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| Names | |
|---|---|
| IUPAC name
2-Amino-4-ethylsulfanylbutyric acid
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| Other names
S-Ethyl-L-homocysteine
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| Identifiers | |
3D model (JSmol)
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| ChEBI | |
| ChEMBL | |
| ChemSpider | |
| ECHA InfoCard | 100.000.588 |
PubChem CID
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| UNII | |
CompTox Dashboard (EPA)
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| Properties | |
| C6H13NO2S | |
| Molar mass | 163.239 g/mol |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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]
Ethionine has been found to naturally occur in the edible pulp of the durian fruit, and postulated to be a biosynthetic precursor for ethanethiol and other strong odorants found in the fruit.[2]
References
[edit]- ^ Narayan Shivapurkar, Mary J. Wilson and Lionel A. Poirier (1984). "Hypomethylation of DNA in ethionine-fed rats". Carcinogenesis. 5 (8): 989–992. doi:10.1093/carcin/5.8.989. PMID 6744518.
- ^ Nadine S. Fischer and Martin Steinhaus (2020). "Identification of an Important Odorant Precursor in Durian: First Evidence of Ethionine in Plants". Journal of Agricultural and Food Chemistry. 68 (38): 10397–10402. doi:10.1021/acs.jafc.9b07065. PMID 31825619. S2CID 209329891.
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