Record Information
Version3.6
Creation Date2006-05-22 15:12:47 UTC
Update Date2013-05-13 20:33:20 UTC
HMDB IDHMDB03288
Secondary Accession NumbersNone
Metabolite Identification
Common NameSelenocysteine
DescriptionSelenocysteine 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
Thumb
Synonyms
  1. (2R)-2-amino-3-selanylpropanoate
  2. (2R)-2-amino-3-selanylpropanoic acid
  3. 3-Seleno-alanine
  4. 3-Selenoalanine
  5. 3-Selenyl-L-Alanine
  6. L-Selenocystein
  7. L-Selenocysteine
  8. L-Selenozystein
Chemical FormulaC3H7NO2Se
Average Molecular Weight168.05
Monoisotopic Molecular Weight168.964200301
IUPAC Name(2R)-2-amino-3-selanylpropanoic acid
Traditional IUPAC Nameselenocysteine
CAS Registry Number3614-08-2
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 KeyZKZBPNGNEQAJSX-REOHCLBHSA-N
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassAmino Acids, Peptides, and Analogues
ClassAmino Acids and Derivatives
Sub ClassAlpha Amino Acids and Derivatives
Other Descriptors
  • Aliphatic Acyclic Compounds
  • alpha-amino acid(ChEBI)
  • selenocysteines(ChEBI)
Substituents
  • Carboxylic Acid
  • Primary Aliphatic Amine (Alkylamine)
  • Selenol
Direct ParentAlpha Amino Acids and Derivatives
Ontology
StatusExpected and Not Quantified
Origin
  • Endogenous
Biofunction
  • Protein synthesis, amino acid biosynthesis
ApplicationNot Available
Cellular locations
  • Cytoplasm
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
water solubility325 g/LALOGPS
logP-3.2ALOGPS
logP-4.1ChemAxon
logS0.29ALOGPS
pKa (strongest acidic)1.27ChemAxon
pKa (strongest basic)8.42ChemAxon
physiological charge0ChemAxon
hydrogen acceptor count3ChemAxon
hydrogen donor count2ChemAxon
polar surface area63.32ChemAxon
rotatable bond count2ChemAxon
refractivity33.45ChemAxon
polarizability10.7ChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
Biofluid LocationsNot Available
Tissue Location
  • Fibroblasts
  • Kidney
  • Testes
  • Thyroid Gland
Pathways
NameSMPDB LinkKEGG Link
Selenoamino Acid MetabolismSMP00029map00450
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB02345
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB002262
KNApSAcK IDC00034230
Chemspider ID23436
KEGG Compound IDC05688
BioCyc IDL-SELENOCYSTEINE
BiGG ID46290
Wikipedia LinkSelenocysteine
NuGOwiki LinkHMDB03288
Metagene LinkHMDB03288
METLIN ID3292
PubChem Compound25076
PDB IDCSE
ChEBI ID16633
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. 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
  2. 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
  3. 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
  4. 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
  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. Pubmed: 3245598
  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. Pubmed: 15294905
  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. Pubmed: 10900258
  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. Pubmed: 2941757

Enzymes

Gene Name:
NME1
Uniprot ID:
P15531
Gene Name:
TXNRD1
Uniprot ID:
Q16881
Gene Name:
TXNRD2
Uniprot ID:
Q9NNW7
Gene Name:
CTH
Uniprot ID:
P32929
Reactions
Selenocystathionine + Water unknown Selenocysteine + Ammonia + 2-Ketobutyric aciddetails
Gene Name:
SEPHS2
Uniprot ID:
Q99611
Gene Name:
GPX1
Uniprot ID:
P07203
Gene Name:
GPX3
Uniprot ID:
P22352
Gene Name:
GPX2
Uniprot ID:
P18283
Gene Name:
DIO1
Uniprot ID:
P49895
Gene Name:
DIO2
Uniprot ID:
Q92813
Gene Name:
SCLY
Uniprot ID:
Q96I15
Reactions
Selenocysteine + reduced acceptor unknown Hydrogen selenide + L-Alanine + acceptordetails
Selenocysteine + Reduced acceptor unknown Hydrogen selenide + L-Alanine + Acceptordetails
Gene Name:
TXNRD3
Uniprot ID:
Q86VQ6
Gene Name:
EPT1
Uniprot ID:
Q9C0D9
Gene Name:
MSRB1
Uniprot ID:
Q9NZV6
Gene Name:
SEPP1
Uniprot ID:
P49908
Gene Name:
SEP15
Uniprot ID:
O60613
Gene Name:
SEPN1
Uniprot ID:
Q9NZV5
Gene Name:
SEPW1
Uniprot ID:
P63302
Gene Name:
SELS
Uniprot ID:
Q9BQE4
Gene Name:
SELK
Uniprot ID:
Q9Y6D0
Gene Name:
SELM
Uniprot ID:
Q8WWX9
Gene Name:
SELT
Uniprot ID:
P62341