| Record Information |
|---|
| Version |
3.5 |
| Creation Date |
2006-05-22 09:12:47 -0600 |
| Update Date |
2013-05-13 14:33:20 -0600 |
| HMDB ID |
HMDB03288 |
| Secondary Accession Numbers |
None |
| Metabolite Identification |
|---|
| Common Name |
Selenocysteine |
| Description |
Selenocysteine is an amino acid that is present in several enzymes (for example glutathione peroxidases, tetraiodothyronine 5' deiodinases, thioredoxin reductases, formate dehydrogenases, glycine reductases and some hydrogenases). Selenocysteine has a structure similar to cysteine, but with an atom of selenium taking the place of the usual sulfur. Proteins that include a selenocysteine residue are called selenoproteins (Wikipedia). Selenocysteine is a naturally occurring amino acid in both eukaryotic and prokaryotic organisms. It is found in tRNAs and in the catalytic site of some enzymes. The genes for glutathione peroxidase and formate dehydrogenase contain the TGA codon, which codes for this amino acid (Pubchem). |
| Structure |
Download:
MOL |
SDF |
SMILES |
InChI
Display:
2D Structure |
3D Structure
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| Synonyms |
- (2R)-2-amino-3-selanylpropanoate
- (2R)-2-amino-3-selanylpropanoic acid
- 3-Seleno-alanine
- 3-Selenoalanine
- 3-Selenyl-L-Alanine
- L-Selenocystein
- L-Selenocysteine
- L-Selenozystein
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| Chemical Formula |
C3H7NO2Se |
| Average Molecular Weight |
168.05 |
| Monoisotopic Molecular Weight |
168.964200301 |
| IUPAC Name |
(2R)-2-amino-3-selanylpropanoic acid |
| Traditional IUPAC Name |
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 |
|---|
| Kingdom |
Organic Compounds |
| Super Class |
Amino Acids, Peptides, and Analogues |
| Class |
Amino Acids and Derivatives |
| Sub Class |
Alpha Amino Acids and Derivatives |
| Other Descriptors |
- Aliphatic Acyclic Compounds
- alpha-amino acid(ChEBI)
- selenocysteines(ChEBI)
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| Substituents |
- Carboxylic Acid
- Primary Aliphatic Amine (Alkylamine)
- Selenol
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| Direct Parent |
Alpha Amino Acids and Derivatives |
| Ontology |
|---|
| Status |
Expected and Not Quantified |
| Origin |
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| Biofunction |
- Protein synthesis, amino acid biosynthesis
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| Application |
Not Available
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| Cellular locations |
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| Physical Properties |
|---|
| State |
Solid |
| Experimental Properties |
| Property |
Value |
Reference |
| Melting Point |
Not Available |
Not Available |
| Boiling Point |
Not Available |
Not Available |
| Water Solubility |
Not Available |
Not Available |
| LogP |
Not Available |
Not Available |
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| Predicted Properties |
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| Spectra |
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Not Available
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| Biological Properties |
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| Cellular Locations |
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| Biofluid Locations |
Not Available
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| Tissue Location |
- Fibroblasts
- Testes
- Kidney
- Thyroid Gland
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| Pathways |
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| Normal Concentrations |
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Not Available |
| Abnormal Concentrations |
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Not Available |
| Associated Disorders and Diseases |
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| Disease References |
None |
| Associated OMIM IDs |
None |
| External Links |
|---|
| DrugBank ID |
DB02345  |
| DrugBank Metabolite ID |
Not Available |
| Phenol Explorer Compound ID |
Not Available |
| Phenol Explorer Metabolite ID |
Not Available |
| FoodDB ID |
FDB002262 |
| KNApSAcK ID |
C00034230 |
| Chemspider ID |
23436 |
| KEGG Compound ID |
C05688 |
| BioCyc ID |
L-SELENOCYSTEINE |
| BiGG ID |
46290 |
| Wikipedia Link |
Selenocysteine |
| NuGOwiki Link |
HMDB03288 |
| Metagene Link |
HMDB03288 |
| METLIN ID |
3292 |
| PubChem Compound |
25076 |
| PDB ID |
CSE |
| ChEBI ID |
16633 |
| References |
|---|
| Synthesis Reference |
Not Available |
| Material Safety Data Sheet (MSDS) |
Not Available
|
| General References |
- Mostert V, Wolff S, Dreher I, Kohrle J, Abel J: Identification of an element within the promoter of human selenoprotein P responsive to transforming growth factor-beta. Eur J Biochem. 2001 Dec;268(23):6176-81.
Pubmed: 11733012
- Zimmermann MB, Kohrle J: The impact of iron and selenium deficiencies on iodine and thyroid metabolism: biochemistry and relevance to public health. Thyroid. 2002 Oct;12(10):867-78.
Pubmed: 12487769
- Sun QA, Su D, Novoselov SV, Carlson BA, Hatfield DL, Gladyshev VN: Reaction mechanism and regulation of mammalian thioredoxin/glutathione reductase. Biochemistry. 2005 Nov 8;44(44):14528-37.
Pubmed: 16262253
- Chu FF, Esworthy RS, Doroshow JH, Doan K, Liu XF: Expression of plasma glutathione peroxidase in human liver in addition to kidney, heart, lung, and breast in humans and rodents. Blood. 1992 Jun 15;79(12):3233-8.
Pubmed: 1339300
- Blotcky AJ, Ebrahim A, Rack EP: Determination of selenium metabolites in biological fluids using instrumental and molecular neutron activation analysis. Anal Chem. 1988 Dec 15;60(24):2734-7.
Pubmed: 3245598
- Utomo A, Jiang X, Furuta S, Yun J, Levin DS, Wang YC, Desai KV, Green JE, Chen PL, Lee WH: Identification of a novel putative non-selenocysteine containing phospholipid hydroperoxide glutathione peroxidase (NPGPx) essential for alleviating oxidative stress generated from polyunsaturated fatty acids in breast cancer cells. J Biol Chem. 2004 Oct 15;279(42):43522-9. Epub 2004 Aug 4.
Pubmed: 15294905
- Rooseboom M, Vermeulen NP, Andreadou I, Commandeur JN: Evaluation of the kinetics of beta-elimination reactions of selenocysteine Se-conjugates in human renal cytosol: possible implications for the use as kidney selective prodrugs. J Pharmacol Exp Ther. 2000 Aug;294(2):762-9.
Pubmed: 10900258
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| Enzymes |
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| Name: |
Selenocysteine lyase
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| Reactions: |
| Selenocysteine + reduced acceptor unknown Hydrogen selenide + L-Alanine + acceptor |
details |
| Selenocysteine + Reduced acceptor unknown Hydrogen selenide + L-Alanine + Acceptor |
details |
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| Gene Name: |
SCLY |
| Uniprot ID: |
Q96I15 |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
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