Selenocystine (BioDeep_00000005927)
human metabolite Endogenous blood metabolite Toxin
代谢物信息卡片
化学式: C6H12N2O4Se2 (335.9127452)
中文名称: L-硒代胱胺基乙酸, 硒代-DL-胱氨酸
谱图信息:
最多检出来源 Homo sapiens(blood) 2.78%
分子结构信息
SMILES: C(C(C(=O)O)N)[Se][Se]CC(C(=O)O)N
InChI: InChI=1S/C6H12N2O4Se2/c7-3(5(9)10)1-13-14-2-4(8)6(11)12/h3-4H,1-2,7-8H2,(H,9,10)(H,11,12)
描述信息
Selenocystine, also known as 3,3-diselenodialanine, belongs to the class of organic compounds known as alpha-amino acids. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxyl group (alpha carbon). More specifically, selenocystine is a diselenide consisting of two selenoamino acids that are attached together at their selenium atoms. This particular selenoamino acid is selenocysteine, the selenium analogue to cysteine (selenium being the element directly beneath sulphur in the periodic table); likewise, selenocystine is the selenium analogue to cystine. Since each constituent amino acid has a stereocentre, there are three different stereoisomers of selenocystine: D-selenocystine, L-selenocystine, and meso-selenocystine, the first two of which are optically active. Like other amino acids, L-selenocystine is the most common form within organisms; however, the D- and meso- forms have also been found (PMID: 30920149). Selenocystine is a solid that is moderately soluble in water. Due to the reactivity of selenocysteine, it is rarely encountered; rather, cells store selenium in the less reactive oxidized form of selenocystine or in a methylated form, such as selenomethionine (DOI: 10.1007/978-3-319-92405-2_3). When cells are grown in the absence of selenium, translation of selenoproteins terminates at the UGA codon, resulting in a truncated, non-functional enzyme. Unlike other amino acids present in biological proteins, selenocysteine is not coded for directly in the genetic code. Rather, the tRNA-bound seryl residue is converted to a selenocysteine residue by the pyridoxal phosphate-containing enzyme selenocysteine synthase (PMID: 17194211). Kurt Franke et al. indicated that there was evidence that selenium was in a form similar to that of cysteine, predating Thressa Stadtman’s discovery of the 21st amino acid by four decades (PMID: 26949981; J. Biol. Chem. 111:643). Selenocysteine may be denoted by the short forms Sec, U, or SeCys (Cys is used for cysteine), whereas selenocystine may be denoted by SeCys2. However, the literature sometimes uses SeCys for selenocystine and may cause confusion. Selenocystine has been found in animals, plants, and bacteria. It is being researched as treatment for cancer and for its antioxidant properties (PMID: 24763048, 24030774). Selenium, in its various forms such as selenocystine, is essential for many species, including humans, yet it is also toxic to all organisms; hence, it has come to be referred to as the “essential poison” (PMID: 26949981; 6679541).
Selenocystine is a substrate for glutathione peroxidase 1. [HMDB]
D000890 - Anti-Infective Agents > D000998 - Antiviral Agents
L-Selenocystine is a diselenide-bridged amino acid. L-Selenocystine is a redox-active selenium compound that has both anti- and pro-oxidant actions. L-Selenocystine induces an unfolded protein response, ER stress, and large cytoplasmic vacuolization in HeLa cells and has cytostatic effects in a range of cancer cell types[1].
同义名列表
13 个代谢物同义名
2-amino-3-[(2-amino-2-carboxyethyl)diselanyl]propanoic acid; (R,R)-3,3-diselenobis-(2-aminopropionic acid); Selenocystine, (DL)-isomer; Selenocystine, (L)-isomer; Selenocystine, (D)-isomer; 3,3-Diselenobisalanine; 3,3-Diselenodialanine; D,L-Selenocystine; seleno-DL-Cystine; DL-Selenocystine; Selenium cystine; L-Selenocystine; Selenocystine
数据库引用编号
18 个数据库交叉引用编号
- ChEBI: CHEBI:28553
- KEGG: C05704
- PubChem: 207306
- PubChem: 15104
- HMDB: HMDB0004122
- Wikipedia: Selenocysteine
- MetaCyc: CPD0-1562
- foodb: FDB023316
- chemspider: 14376
- CAS: 13900-89-5
- CAS: 29621-88-3
- CAS: 1464-43-3
- CAS: 2897-21-4
- PMhub: MS000018840
- PubChem: 8011
- 3DMET: B05102
- NIKKAJI: J14.789C
- medchemexpress: HY-129960
分类词条
相关代谢途径
Reactome(0)
BioCyc(0)
PlantCyc(0)
代谢反应
6 个相关的代谢反应过程信息。
Reactome(0)
BioCyc(0)
WikiPathways(0)
Plant Reactome(0)
INOH(0)
PlantCyc(0)
COVID-19 Disease Map(0)
PathBank(6)
- Selenoamino Acid Metabolism:
Selenocystathionine + Water ⟶ 2-Ketobutyric acid + Ammonia + Selenocysteine
- Selenoamino Acid Metabolism:
Selenocystathionine + Water ⟶ 2-Ketobutyric acid + Ammonia + Selenocysteine
- Selenoamino Acid Metabolism:
Selenocystathionine + Water ⟶ 2-Ketobutyric acid + Ammonia + Selenocysteine
- Selenoamino Acid Metabolism:
Selenocystathionine + Water ⟶ 2-Ketobutyric acid + Ammonia + Selenocysteine
- Selenoamino Acid Metabolism:
Selenocystathionine + Water ⟶ 2-Ketobutyric acid + Ammonia + Selenocysteine
- Selenoamino Acid Metabolism:
Selenocystathionine + Water ⟶ 2-Ketobutyric acid + Ammonia + Selenocysteine
PharmGKB(0)
1 个相关的物种来源信息
在这里通过桑基图来展示出与当前的这个代谢物在我们的BioDeep知识库中具有相关联信息的其他代谢物。在这里进行关联的信息来源主要有:
- PubMed: 来源于PubMed文献库中的文献信息,我们通过自然语言数据挖掘得到的在同一篇文献中被同时提及的相关代谢物列表,这个列表按照代谢物同时出现的文献数量降序排序,取前10个代谢物作为相关研究中关联性很高的代谢物集合展示在桑基图中。
- NCBI Taxonomy: 通过文献数据挖掘,得到的代谢物物种来源信息关联。这个关联信息同样按照出现的次数降序排序,取前10个代谢物作为高关联度的代谢物集合展示在桑吉图上。
- Chemical Taxonomy: 在物质分类上处于同一个分类集合中的其他代谢物
- Chemical Reaction: 在化学反应过程中,存在为当前代谢物相关联的生化反应过程中的反应底物或者反应产物的关联代谢物信息。
点击图上的相关代谢物的名称,可以跳转到相关代谢物的信息页面。
文献列表
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