| Record Information |
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| Version | 1.0 |
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| Creation Date | 2016-05-25 21:41:33 UTC |
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| Update Date | 2016-11-09 01:17:53 UTC |
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| Accession Number | CHEM024427 |
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| Identification |
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| Common Name | Selenocysteine |
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| Class | Small Molecule |
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| Description | 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] |
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| Contaminant Sources | - FooDB Chemicals
- STOFF IDENT Compounds
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| Contaminant Type | Not Available |
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| Chemical Structure | |
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| Synonyms | | Value | Source |
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| 3-Selenyl-L-alanine | ChEBI | | L-Selenocystein | ChEBI | | L-Selenozystein | ChEBI | | (2R)-2-Amino-3-selanylpropanoate | HMDB | | (2R)-2-Amino-3-selanylpropanoic acid | HMDB | | 3-Seleno-alanine | HMDB | | 3-Selenoalanine | HMDB | | L-Selenocysteine | HMDB |
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| Chemical Formula | C3H7NO2Se |
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| Average Molecular Mass | 168.050 g/mol |
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| Monoisotopic Mass | 168.964 g/mol |
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| CAS Registry Number | 10236-58-5 |
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| IUPAC Name | (2R)-2-amino-3-selanylpropanoic acid |
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| Traditional Name | L-selenocysteine |
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| SMILES | NC(C[SeH])C(O)=O |
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| InChI Identifier | InChI=1S/C3H7NO2Se/c4-2(1-7)3(5)6/h2,7H,1,4H2,(H,5,6) |
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| InChI Key | ZKZBPNGNEQAJSX-UHFFFAOYSA-N |
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| Chemical Taxonomy |
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| 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. |
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| Kingdom | Organic compounds |
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| Super Class | Organic acids and derivatives |
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| Class | Carboxylic acids and derivatives |
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| Sub Class | Amino acids, peptides, and analogues |
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| Direct Parent | L-alpha-amino acids |
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| Alternative Parents | |
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| Substituents | - L-alpha-amino acid
- Amino acid
- Carboxylic acid
- Monocarboxylic acid or derivatives
- Amine
- Organic oxide
- Hydrocarbon derivative
- Organopnictogen compound
- Selenol
- Primary amine
- Organoselenium compound
- Organooxygen compound
- Organonitrogen compound
- Organic oxygen compound
- Primary aliphatic amine
- Organic nitrogen compound
- Carbonyl group
- Aliphatic acyclic compound
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| Molecular Framework | Aliphatic acyclic compounds |
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| External Descriptors | |
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| Biological Properties |
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| Status | Detected and Not Quantified |
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| Origin | Not Available |
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| Cellular Locations | Not Available |
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| Biofluid Locations | Not Available |
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| Tissue Locations | Not Available |
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| Pathways | Not Available |
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| Applications | Not Available |
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| Biological Roles | Not Available |
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| Chemical Roles | Not Available |
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| Physical Properties |
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| State | Not Available |
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| Appearance | Not Available |
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| Experimental Properties | | Property | Value |
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| Melting Point | Not Available | | Boiling Point | Not Available | | Solubility | Not Available |
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| Predicted Properties | |
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| Spectra |
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| Spectra | | Spectrum Type | Description | Splash Key | View |
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| Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-00di-5900000000-827b47dc191649f521ac | Spectrum | | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive | splash10-00di-5900000000-32e999fe6e3d67e322cb | Spectrum | | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | Not Available | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-01b9-0900000000-fadd5a69b2b225d034ac | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-01b9-0900000000-8fe6412cebc1ca99fe59 | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-00dl-5900000000-2408222e037ff9db752a | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-014i-0900000000-91ba91d891f89ff1fc23 | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-00kk-6900000000-67c579b8ba30e155bcb3 | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-00di-9200000000-0b58b77f13cec3df121d | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-014i-0900000000-59cfe0ab1984ab09d7af | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-01b9-7900000000-6f634fdb5ee7a8437ca7 | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-014i-1900000000-0f58b4784272be073705 | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-01b9-0900000000-3a288e1fc4c42cfb333c | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-05fr-0900000000-c29c42f6924485632ad3 | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0a4i-2900000000-8f03b287aede9d710058 | Spectrum | | 1D NMR | 13C NMR Spectrum | Not Available | Spectrum | | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | | 1D NMR | 13C NMR Spectrum | Not Available | Spectrum | | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | | 1D NMR | 13C NMR Spectrum | Not Available | Spectrum | | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | | 1D NMR | 13C NMR Spectrum | Not Available | Spectrum | | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | | 1D NMR | 13C NMR Spectrum | Not Available | Spectrum | | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | | 1D NMR | 13C NMR Spectrum | Not Available | Spectrum | | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | | 1D NMR | 13C NMR Spectrum | Not Available | Spectrum | | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | | 1D NMR | 13C NMR Spectrum | Not Available | Spectrum | | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | | 1D NMR | 13C NMR Spectrum | Not Available | Spectrum | | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | | 1D NMR | 13C NMR Spectrum | Not Available | Spectrum | | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum |
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| Toxicity Profile |
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| Route of Exposure | Not Available |
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| Mechanism of Toxicity | Not Available |
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| Metabolism | Not Available |
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| Toxicity Values | Not Available |
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| Lethal Dose | Not Available |
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| Carcinogenicity (IARC Classification) | Not Available |
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| Uses/Sources | Not Available |
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| Minimum Risk Level | Not Available |
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| Health Effects | Not Available |
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| Symptoms | Not Available |
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| Treatment | Not Available |
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| Concentrations |
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| Not Available |
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| External Links |
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| DrugBank ID | DB02345 |
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| HMDB ID | HMDB0003288 |
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| FooDB ID | FDB002262 |
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| Phenol Explorer ID | Not Available |
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| KNApSAcK ID | C00034230 |
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| BiGG ID | 46290 |
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| BioCyc ID | L-SELENOCYSTEINE |
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| METLIN ID | 3292 |
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| PDB ID | Not Available |
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| Wikipedia Link | Selenocysteine |
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| Chemspider ID | 23436 |
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| ChEBI ID | 16633 |
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| PubChem Compound ID | 25076 |
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| Kegg Compound ID | C05688 |
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| YMDB ID | YMDB16154 |
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| ECMDB ID | ECMDB03288 |
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| References |
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| Synthesis Reference | Not Available |
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| MSDS | Not Available |
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| General References | | 1. 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. | | 2. 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. | | 3. 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. | | 4. 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. | | 5. 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. | | 6. 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. | | 7. 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. | | 8. Zinoni F, Birkmann A, Stadtman TC, Bock A: Nucleotide sequence and expression of the selenocysteine-containing polypeptide of formate dehydrogenase (formate-hydrogen-lyase-linked) from Escherichia coli. Proc Natl Acad Sci U S A. 1986 Jul;83(13):4650-4. | | 9. https://www.ncbi.nlm.nih.gov/pubmed/?term=11733012 | | 10. https://www.ncbi.nlm.nih.gov/pubmed/?term=18429173 |
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