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Identification
NameSelenocysteine
Accession NumberDB02345  (EXPT01033)
Typesmall molecule
Groupsexperimental
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]

Structure
Thumb
SynonymsNot Available
SaltsNot Available
Brand namesNot Available
Brand mixturesNot Available
CategoriesNot Available
CAS number4408-78-0
WeightAverage: 168.05
Monoisotopic: 168.964200301
Chemical FormulaC3H7NO2Se
InChI KeyInChIKey=ZKZBPNGNEQAJSX-REOHCLBHSA-N
InChI
InChI=1S/C3H7NO2Se/c4-2(1-7)3(5)6/h2,7H,1,4H2,(H,5,6)/t2-/m0/s1
IUPAC Name
(2R)-2-amino-3-selanylpropanoic acid
SMILES
N[C@@H](C[SeH])C(O)=O
Mass SpecNot Available
Taxonomy
KingdomOrganic Compounds
SuperclassOrganic Acids and Derivatives
ClassCarboxylic Acids and Derivatives
SubclassAmino Acids, Peptides, and Analogues
Direct parentAlpha Amino Acids and Derivatives
Alternative parentsPolyamines; Enolates; Enols; Carboxylic Acids; Organoselenium Compounds; Monoalkylamines
Substituentscarboxylic acid; enol; enolate; polyamine; primary amine; amine; primary aliphatic amine; organoselenium compound; organonitrogen compound
Classification descriptionThis compound belongs to the alpha amino acids and derivatives. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon), or a derivative thereof.
Pharmacology
IndicationNot Available
PharmacodynamicsNot Available
Mechanism of actionNot Available
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
Metabolism
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organismsNot Available
Pathways
PathwayCategorySMPDB ID
Selenoamino Acid MetabolismMetabolicSMP00029
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
Property Value Probability
Human Intestinal Absorption + 0.9454
Blood Brain Barrier + 0.5652
Caco-2 permeable - 0.7223
P-glycoprotein substrate Non-substrate 0.7899
P-glycoprotein inhibitor I Non-inhibitor 0.9841
P-glycoprotein inhibitor II Non-inhibitor 0.9834
Renal organic cation transporter Non-inhibitor 0.9391
CYP450 2C9 substrate Non-substrate 0.8503
CYP450 2D6 substrate Non-substrate 0.815
CYP450 3A4 substrate Non-substrate 0.817
CYP450 1A2 substrate Non-inhibitor 0.938
CYP450 2C9 substrate Non-inhibitor 0.9535
CYP450 2D6 substrate Non-inhibitor 0.9623
CYP450 2C19 substrate Non-inhibitor 0.959
CYP450 3A4 substrate Non-inhibitor 0.9549
CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9919
Ames test AMES toxic 0.6345
Carcinogenicity Non-carcinogens 0.7841
Biodegradation Ready biodegradable 0.941
Rat acute toxicity 1.5769 LD50, mol/kg Not applicable
hERG inhibition (predictor I) Weak inhibitor 0.9863
hERG inhibition (predictor II) Non-inhibitor 0.9697
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
Statesolid
Experimental Properties
PropertyValueSource
melting point143-146 °CPhysProp
water solubility3.92E+005 mg/L (at 0 °C)STEPHEN,H & STEPHEN,T (1963)
Predicted Properties
PropertyValueSource
water solubility3.25e+02 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
polarizability10.67ChemAxon
number of rings0ChemAxon
bioavailability1ChemAxon
rule of fiveYesChemAxon
Ghose filterNoChemAxon
Veber's ruleNoChemAxon
MDDR-like ruleNoChemAxon
Spectra
SpectraNot Available
References
Synthesis ReferenceNot Available
General Reference
  1. 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
ResourceLink
KEGG CompoundC05688
PubChem Compound25076
PubChem Substance46508133
ChemSpider828
ChEBI9093
ChEMBL
HETCSE
WikipediaSelenocysteine
ATC CodesNot Available
AHFS CodesNot Available
PDB Entries
FDA labelNot Available
MSDSNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

1. Cathelicidin antimicrobial peptide

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Cathelicidin antimicrobial peptide P49913 Details

References:

  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed
  3. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. Pubmed

2. Nucleoside diphosphate kinase A

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Nucleoside diphosphate kinase A P15531 Details

References:

  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed
  3. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. Pubmed

3. Formate dehydrogenase H

Kind: protein

Organism: Escherichia coli (strain K12)

Pharmacological action: unknown

Components

Name UniProt ID Details
Formate dehydrogenase H P07658 Details

References:

  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed

4. Cysteine desulfurase

Kind: protein

Organism: Escherichia coli (strain K12)

Pharmacological action: unknown

Components

Name UniProt ID Details
Cysteine desulfurase P77444 Details

References:

  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed

Comments
Drug created on June 13, 2005 07:24 / Updated on September 16, 2013 17:17