(2R)-2-amino-3-selanylpropanoic acid

• ChemBase ID: 2086
• Molecular Formular: C3H7NO2Se
• Molecular Mass: 168.05318
• Monoisotopic Mass: 168.96419947
• SMILES: N[C@@H](C[SeH])C(=O)O
• Canonical SMILES: N[C@H](C(=O)O)C[SeH]
• 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

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R)-2-amino-3-selanylpropanoic acid
• IUPAC Traditional name: L-selenocysteine
• Synonyms: L-Selenocysteine; 3-Selanyl-L-alanine; Selenium cysteine; Selenocysteine

Database IDs

• CAS Number: 4408-78-0; 10236-58-5
• PubChem SID: 160965540; 46508133
• PubChem CID: 25076; 6326983
• CHEBI ID: 16633
• CHEMBL: 109962
• Chemspider ID: 23436
• DrugBank ID: DB02345
• KEGG ID: C05688
• Wikipedia Title: Selenocysteine

CALCULATED PROPERTIES

JChem

• Acid pKa: 1.2678685
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): -4.066753
• LogD (pH = 7.4): -4.100274
• Log P: -4.066487
• Molar Refractivity: 33.4469 cm^3
• Polarizability: 8.9092865 Å^3
• Polar Surface Area: 63.32 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: -3.2
• LOG S: 0.29
• Solubility (Water): 3.25e+02 g/l

PROPERTIES

Physical Property

• Solubility: 392 mg/mL at 0 oC [STEPHEN,H & STEPHEN,T (1963)]

DETAILS

DrugBank - DB02345

• Drug Groups: experimental
• 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]
• References: 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]
• External Links: Wikipedia

REFERENCES

• 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