CHEBI:16633 - L-selenocysteine

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ChEBI Name L-selenocysteine
ChEBI ID CHEBI:16633
ChEBI ASCII Name L-selenocysteine
Definition The L-enantiomer of selenocysteine.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:21385, CHEBI:49562, CHEBI:6298, CHEBI:13165
Supplier Information No supplier information found for this compound.
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Selenocysteine (symbol Sec or U, in older publications also as Se-Cys) is the 21st proteinogenic amino acid. Selenoproteins contain selenocysteine residues. Selenocysteine is an analogue of the more common cysteine with selenium in place of the sulfur. Selenocysteine is present in several enzymes (for example glutathione peroxidases, tetraiodothyronine 5′ deiodinases, thioredoxin reductases, formate dehydrogenases, glycine reductases, selenophosphate synthetase 2, methionine-R-sulfoxide reductase B1 (SEPX1), and some hydrogenases). It occurs in all three domains of life, including important enzymes (listed above) present in humans. Selenocysteine was discovered in 1974 by biochemist Thressa Stadtman at the National Institutes of Health.
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Formula C3H7NO2Se
Net Charge 0
Average Mass 168.065
Monoisotopic Mass 168.96420
InChI InChI=1S/C3H7NO2Se/c4-2(1-7)3(5)6/h2,7H,1,4H2,(H,5,6)/t2-/m0/s1
InChIKey ZKZBPNGNEQAJSX-REOHCLBHSA-N
SMILES C([C@@H](C(O)=O)N)[SeH]
Metabolite of Species Details
Homo sapiens (NCBI:txid9606) See: PubMed
Roles Classification
Chemical Role(s): Bronsted base
A molecular entity capable of accepting a hydron from a donor (Bronsted acid).
(via organic amino compound )
Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
(via oxoacid )
Biological Role(s): human metabolite
Any mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens).
(via selenocysteine )
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ChEBI Ontology
Outgoing L-selenocysteine (CHEBI:16633) has role human metabolite (CHEBI:77746)
L-selenocysteine (CHEBI:16633) is a L-α-amino acid (CHEBI:15705)
L-selenocysteine (CHEBI:16633) is a L-alanine derivative (CHEBI:83943)
L-selenocysteine (CHEBI:16633) is a proteinogenic amino acid (CHEBI:83813)
L-selenocysteine (CHEBI:16633) is a selenocysteine (CHEBI:9093)
L-selenocysteine (CHEBI:16633) is conjugate acid of L-selenocysteinate(1−) (CHEBI:32742)
L-selenocysteine (CHEBI:16633) is conjugate base of L-selenocysteinium (CHEBI:32744)
L-selenocysteine (CHEBI:16633) is enantiomer of D-selenocysteine (CHEBI:30001)
L-selenocysteine (CHEBI:16633) is tautomer of L-selenocysteine zwitterion (CHEBI:57843)
Incoming L-selenocysteine derivative (CHEBI:84209) has functional parent L-selenocysteine (CHEBI:16633)
L-selenocysteinium (CHEBI:32744) is conjugate acid of L-selenocysteine (CHEBI:16633)
L-selenocysteinate(1−) (CHEBI:32742) is conjugate base of L-selenocysteine (CHEBI:16633)
D-selenocysteine (CHEBI:30001) is enantiomer of L-selenocysteine (CHEBI:16633)
L-selenocysteine residue (CHEBI:30000) is substituent group from L-selenocysteine (CHEBI:16633)
L-selenocysteino group (CHEBI:32746) is substituent group from L-selenocysteine (CHEBI:16633)
L-selenocysteinyl group (CHEBI:32745) is substituent group from L-selenocysteine (CHEBI:16633)
L-selenocysteine zwitterion (CHEBI:57843) is tautomer of L-selenocysteine (CHEBI:16633)
IUPAC Name
(2R)-2-amino-3-selanylpropanoic acid
Synonyms Sources
3-selenyl-L-alanine ChemIDplus
L-Selenocystein ChEBI
L-Selenocysteine KEGG COMPOUND
L-Selenozystein ChEBI
SELENOCYSTEINE PDBeChem
Selenocysteine ChemIDplus
Manual Xrefs Databases
C05688 KEGG COMPOUND
ECMDB03288 ECMDB
HMDB0003288 HMDB
L-SELENOCYSTEINE MetaCyc
SEC PDBeChem
Selenocysteine Wikipedia
View more database links
Registry Numbers Types Sources
10236-58-5 CAS Registry Number ChemIDplus
2498378 Reaxys Registry Number Reaxys
Citations
Gladyshev VN, Hatfield DL (2001)
Analysis of selenocysteine-containing proteins.
Current protocols in protein science Chapter 3, Unit 3.8 [PubMed:18429173]
[show Abstract]
Mostert V, Wolff S, Dreher I, Köhrle J, Abel J (2001)
Identification of an element within the promoter of human selenoprotein P responsive to transforming growth factor-beta.
European journal of biochemistry 268, 6176-6181 [PubMed:11733012]
[show Abstract]
Last Modified
21 November 2019