Showing metabocard for Selenocysteine (BMDB0003288)
| Record Information | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Version | 1.0 | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Creation Date | 2016-09-30 23:03:28 UTC | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Update Date | 2020-05-21 16:26:51 UTC | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| BMDB ID | BMDB0003288 | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Secondary Accession Numbers |
| |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Metabolite Identification | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Common Name | Selenocysteine | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Description | Selenocysteine, also known as Selenocysteine, belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom. Selenocysteine is possibly soluble (in water) and a very strong basic compound (based on its pKa). Selenocysteine exists in all living species, ranging from bacteria to humans. Selenocysteine participates in a number of enzymatic reactions, within cattle. In particular, Selenocysteine can be converted into L-alanine and hydrogen selenide; which is mediated by the enzyme selenocysteine lyase. In addition, Selenocysteine and 2-ketobutyric acid can be biosynthesized from selenocystathionine; which is mediated by the enzyme cystathionine gamma-lyase. In cattle, selenocysteine is involved in the metabolic pathway called the selenoamino acid metabolism pathway. | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Structure | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Synonyms |
| |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Chemical Formula | C3H7NO2Se | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Average Molecular Weight | 168.05 | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Monoisotopic Molecular Weight | 168.964200301 | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| IUPAC Name | (2R)-2-amino-3-selanylpropanoic acid | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Traditional Name | L-selenocysteine | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| CAS Registry Number | 3614-08-2 | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| SMILES | N[C@@H](C[SeH])C(O)=O | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| InChI Identifier | InChI=1S/C3H7NO2Se/c4-2(1-7)3(5)6/h2,7H,1,4H2,(H,5,6)/t2-/m0/s1 | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| InChI Key | ZKZBPNGNEQAJSX-REOHCLBHSA-N | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Chemical Taxonomy | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Description | belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom. | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Kingdom | Organic compounds | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Super Class | Organic acids and derivatives | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Class | Carboxylic acids and derivatives | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Sub Class | Amino acids, peptides, and analogues | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Direct Parent | L-alpha-amino acids | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Alternative Parents | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Substituents |
| |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Molecular Framework | Aliphatic acyclic compounds | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| External Descriptors |
| |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Ontology | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Status | Expected but not Quantified | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Origin |
| |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Biofunction | Not Available | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Application | Not Available | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Cellular locations |
| |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Physical Properties | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| State | Solid | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Experimental Properties |
| |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Predicted Properties |
| |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Spectra | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Spectra | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Biological Properties | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Cellular Locations |
| |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Biospecimen Locations |
| |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Pathways | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Normal Concentrations | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Abnormal Concentrations | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Not Available | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| External Links | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| HMDB ID | HMDB0003288 | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| DrugBank ID | DB02345 | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Phenol Explorer Compound ID | Not Available | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| FooDB ID | FDB002262 | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| KNApSAcK ID | C00034230 | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Chemspider ID | 23436 | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| KEGG Compound ID | C05688 | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| BioCyc ID | L-SELENOCYSTEINE | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| BiGG ID | 46290 | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Wikipedia Link | Selenocysteine | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| METLIN ID | 3292 | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| PubChem Compound | 25076 | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| PDB ID | Not Available | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| ChEBI ID | 16633 | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| References | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Synthesis Reference | Not Available | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Material Safety Data Sheet (MSDS) | Not Available | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| General References | Not Available | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Enzymes
- General function:
- Involved in ethanolaminephosphotransferase activity
- Specific function:
- Catalyzes phosphatidylethanolamine biosynthesis from CDP-ethanolamine. It thereby plays a central role in the formation and maintenance of vesicular membranes. Involved in the foramtion of phosphatidylethanolamine via 'Kennedy' pathway (By similarity).
- Gene Name:
- SELENOI
- Uniprot ID:
- Q17QM4
- Molecular weight:
- 45214.0
- General function:
- Energy production and conversion
- Specific function:
- Involved in the control of reactive oxygen species levels and the regulation of mitochondrial redox homeostasis (By similarity). Maintains thioredoxin in a reduced state. May play a role in redox-regulated cell signaling.
- Gene Name:
- TXNRD2
- Uniprot ID:
- Q9N2I8
- Molecular weight:
- 54670.0
- General function:
- Energy production and conversion
- Specific function:
- Not Available
- Gene Name:
- TXNRD1
- Uniprot ID:
- O62768
- Molecular weight:
- 54770.0
- General function:
- Posttranslational modification, protein turnover, chaperones
- Specific function:
- Essential antioxidant peroxidase that directly reduces phospholipid hydroperoxide even if they are incorporated in membranes and lipoproteins (By similarity). Can also reduce fatty acid hydroperoxide, cholesterol hydroperoxide and thymine hydroperoxide (By similarity). Plays a key role in protecting cells from oxidative damage by preventing membrane lipid peroxidation. Required to prevent cells from ferroptosis, a non-apoptotic cell death resulting from an iron-dependent accumulation of lipid reactive oxygen species. The presence of selenocysteine (Sec) versus Cys at the active site is essential for life: it provides resistance to overoxidation and prevents cells against ferroptosis. The presence of Sec at the active site is also essential for the survival of a specific type of parvalbumin-positive interneurons, thereby preventing against fatal epileptic seizures. May be required to protect cells from the toxicity of ingested lipid hydroperoxides. Required for normal sperm development and male fertility. Essential for maturation and survival of photoreceptor cells. Plays a role in a primary T-cell response to viral and parasitic infection by protecting T-cells from ferroptosis and by supporting T-cell expansion (By similarity).
- Gene Name:
- GPX4
- Uniprot ID:
- Q9N2J2
- Molecular weight:
- 22240.0
- General function:
- Posttranslational modification, protein turnover, chaperones
- Specific function:
- Protects cells and enzymes from oxidative damage, by catalyzing the reduction of hydrogen peroxide, lipid peroxides and organic hydroperoxide, by glutathione.
- Gene Name:
- GPX3
- Uniprot ID:
- P37141
- Molecular weight:
- 25663.0
- General function:
- Involved in selenium binding
- Specific function:
- Responsible for the deiodination of T4 (3,5,3',5'-tetraiodothyronine).
- Gene Name:
- DIO2
- Uniprot ID:
- Q5I3B0
- Molecular weight:
- 3734.0
- General function:
- Posttranslational modification, protein turnover, chaperones
- Specific function:
- Protects the hemoglobin in erythrocytes from oxidative breakdown.
- Gene Name:
- GPX1
- Uniprot ID:
- P00435
- Molecular weight:
- 22659.0
- General function:
- Involved in selenium binding
- Specific function:
- Responsible for the deiodination of T4 (3,5,3',5'-tetraiodothyronine).
- Gene Name:
- Not Available
- Uniprot ID:
- Q9BDR5
- Molecular weight:
- 11173.0
- General function:
- Involved in selenium binding
- Specific function:
- Responsible for the deiodination of T4 (3,5,3',5'-tetraiodothyronine) into T3 (3,5,3'-triiodothyronine). Essential for providing the brain with appropriate levels of T3 during the critical period of development.
- Gene Name:
- DIO2
- Uniprot ID:
- Q5I3B2
- Molecular weight:
- 30303.0
- General function:
- Posttranslational modification, protein turnover, chaperones
- Specific function:
- Methionine-sulfoxide reductase that specifically reduces methionine (R)-sulfoxide back to methionine. While in many cases, methionine oxidation is the result of random oxidation following oxidative stress, methionine oxidation is also a post-translational modification that takes place on specific residue. Acts as a regulator of actin assembly by reducing methionine (R)-sulfoxide mediated by MICALs (MICAL1, MICAL2 or MICAL3) on actin, thereby promoting filament repolymerization. Plays a role in innate immunity by reducing oxidized actin, leading to actin repolymerization in macrophages.
- Gene Name:
- MSRB1
- Uniprot ID:
- Q3MHL9
- Molecular weight:
- 12833.0
- General function:
- Involved in selenium binding
- Specific function:
- Responsible for the deiodination of T4 (3,5,3',5'-tetraiodothyronine) into RT3 (3,3',5'-triiodothyronine) and of T3 (3,5,3'-triiodothyronine) into T2 (3,3'-diiodothyronine). RT3 and T2 are inactive metabolites. May play a role in preventing premature exposure of developing fetal tissues to adult levels of thyroid hormones. Can regulate circulating fetal thyroid hormone concentrations throughout gestation. Essential role for regulation of thyroid hormone inactivation during embryological development.
- Gene Name:
- DIO3
- Uniprot ID:
- Q5I3B1
- Molecular weight:
- 33888.0
- General function:
- Amino acid transport and metabolism
- Specific function:
- Catalyzes the last step in the trans-sulfuration pathway from methionine to cysteine. Has broad substrate specificity. Converts cystathionine to cysteine, ammonia and 2-oxobutanoate. Converts two cysteine molecules to lanthionine and hydrogen sulfide. Can also accept homocysteine as substrate. Specificity depends on the levels of the endogenous substrates. Generates the endogenous signaling molecule hydrogen sulfide (H2S), and so contributes to the regulation of blood pressure. Acts as a cysteine-protein sulfhydrase by mediating sulfhydration of target proteins: sulfhydration consists of converting -SH groups into -SSH on specific cysteine residues of target proteins such as GAPDH, PTPN1 and NF-kappa-B subunit RELA, thereby regulating their function (By similarity).
- Gene Name:
- CTH
- Uniprot ID:
- Q58DW2
- Molecular weight:
- 44406.0
Reactions
| Selenocystathionine + Water → Selenocysteine + Ammonia + 2-Ketobutyric acid | details |
- General function:
- Involved in selenium binding
- Specific function:
- Selenoprotein with thioredoxin reductase-like oxidoreductase activity (By similarity). Protects dopaminergic neurons against oxidative stress ans cell death (By similarity). Involved in ADCYAP1/PACAP-induced calcium mobilization and neuroendocrine secretion (By similarity). Plays a role in fibroblast anchorage and redox regulation (By similarity). In gastric smooth muscle, modulates the contraction processes through the regulation of calcium release and MYLK activation (By similarity). In pancreatic islets, involved in the control of glucose homeostasis, contributes to prolonged ADCYAP1/PACAP-induced insulin secretion (By similarity).
- Gene Name:
- SELENOT
- Uniprot ID:
- A6QP01
- Molecular weight:
- 22248.0
- General function:
- Involved in selenium binding
- Specific function:
- Involved in the degradation process of misfolded endoplasmic reticulum (ER) luminal proteins. Participates in the transfer of misfolded proteins from the ER to the cytosol, where they are destroyed by the proteasome in a ubiquitin-dependent manner. Probably acts by serving as a linker between DERL1, which mediates the retrotranslocation of misfolded proteins into the cytosol, and the ATPase complex VCP, which mediates the translocation and ubiquitination (By similarity).
- Gene Name:
- SELENOS
- Uniprot ID:
- Q2KI76
- Molecular weight:
- 21385.0
- General function:
- Inorganic ion transport and metabolism
- Specific function:
- Constitutes a major selenium pool in the brain and may play an important role in developing and/or modulating the morphology of neurons and/or glial cells.
- Gene Name:
- SELENOP
- Uniprot ID:
- P49907
- Molecular weight:
- 45488.0
- General function:
- Involved in selenium binding
- Specific function:
- Required for Ca(2+) flux in immune cells and plays a role in T-cell proliferation and in T-cell and neutrophil migration (By similarity). Involved in endoplasmic reticulum-associated degradation (ERAD) of soluble glycosylated proteins (By similarity). Required for palmitoylation and cell surface expression of CD36 and involved in macrophage uptake of low-density lipoprotein and in foam cell formation (By similarity). Together with ZDHHC6, required for palmitoylation of ITPR1 in immune cells, leading to regulate ITPR1 stability and function. Plays a role in protection of cells from ER stress-induced apoptosis. Protects cells from oxidative stress when overexpressed in cardiomyocytes (By similarity).
- Gene Name:
- SELENOK
- Uniprot ID:
- Q32PE3
- Molecular weight:
- 10805.0
- General function:
- Involved in selenium binding
- Specific function:
- May be involved in redox reactions associated with the formation of disulfide bonds (By similarity). May contribute to the quality control of protein folding in the endoplasmic reticulum. May regulate protein folding by enhancing the catalytic activity of UGGT1/UGCGL1 and UGGT2/UGCGL2 (By similarity).
- Gene Name:
- SELENOF
- Uniprot ID:
- A8YXY3
- Molecular weight:
- 17975.0