Selenocysteine

Identification

Name
Selenocysteine
Accession Number
DB02345  (EXPT01033)
Type
Small Molecule
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]

Structure
Thumb
Synonyms
  • 3-selenyl-L-alanine
  • L-selenocysteine
  • Selenium cysteine
Categories
UNII
0CH9049VIS
CAS number
10236-58-5
Weight
Average: 168.05
Monoisotopic: 168.964200301
Chemical Formula
C3H7NO2Se
InChI Key
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[[email protected]@H](C[SeH])C(O)=O

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UCathelicidin antimicrobial peptideNot AvailableHuman
UNucleoside diphosphate kinase ANot AvailableHuman
UFormate dehydrogenase HNot AvailableEscherichia coli (strain K12)
UCysteine desulfuraseNot AvailableEscherichia coli (strain K12)
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
Not Available
Pathways
PathwayCategory
Selenoamino Acid MetabolismMetabolic
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

General References
  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:2941757]
External Links
Human Metabolome Database
HMDB03288
KEGG Compound
C05688
PubChem Compound
6326983
PubChem Substance
46508133
ChemSpider
23436
ChEBI
16633
ChEMBL
CHEMBL109962
HET
SEC
Wikipedia
Selenocysteine
PDB Entries
1aa6 / 1cc1 / 1fdi / 1fdo / 1h0h / 1kmk / 1kqf / 1kqg / 1pae / 1pfp
show 28 more

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)143-146 °CPhysProp
water solubility3.92E+005 mg/L (at 0 °C)STEPHEN,H & STEPHEN,T (1963)
Predicted Properties
PropertyValueSource
Water Solubility325.0 mg/mLALOGPS
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 Area63.32 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity33.45 m3·mol-1ChemAxon
Polarizability10.67 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9454
Blood Brain Barrier+0.5652
Caco-2 permeable-0.7223
P-glycoprotein substrateNon-substrate0.7899
P-glycoprotein inhibitor INon-inhibitor0.9841
P-glycoprotein inhibitor IINon-inhibitor0.9834
Renal organic cation transporterNon-inhibitor0.9391
CYP450 2C9 substrateNon-substrate0.8503
CYP450 2D6 substrateNon-substrate0.815
CYP450 3A4 substrateNon-substrate0.817
CYP450 1A2 substrateNon-inhibitor0.938
CYP450 2C9 inhibitorNon-inhibitor0.9535
CYP450 2D6 inhibitorNon-inhibitor0.9623
CYP450 2C19 inhibitorNon-inhibitor0.959
CYP450 3A4 inhibitorNon-inhibitor0.9549
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9919
Ames testAMES toxic0.6345
CarcinogenicityNon-carcinogens0.7841
BiodegradationReady biodegradable0.941
Rat acute toxicity1.5769 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9863
hERG inhibition (predictor II)Non-inhibitor0.9697
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-01b9-0900000000-fadd5a69b2b225d034ac
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-01b9-0900000000-8fe6412cebc1ca99fe59
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-00dl-5900000000-2408222e037ff9db752a
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-014i-0900000000-91ba91d891f89ff1fc23
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-00kk-6900000000-67c579b8ba30e155bcb3
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-00di-9200000000-0b58b77f13cec3df121d

Taxonomy

Description
This compound 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.
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Carboxylic acids and derivatives
Sub Class
Amino acids, peptides, and analogues
Direct Parent
L-alpha-amino acids
Alternative Parents
Amino acids / Monocarboxylic acids and derivatives / Carboxylic acids / Selenols / Organopnictogen compounds / Organic oxides / Monoalkylamines / Hydrocarbon derivatives / Carbonyl compounds
Substituents
L-alpha-amino acid / Amino acid / Carboxylic acid / Monocarboxylic acid or derivatives / Amine / Organic oxide / Hydrocarbon derivative / Organopnictogen compound / Selenol / Primary amine
Molecular Framework
Aliphatic acyclic compounds
External Descriptors
proteinogenic amino acid, L-alpha-amino acid, L-alanine derivative, selenocysteine (CHEBI:16633) / Other amino acids (C05688)

Targets

Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Not Available
Specific Function
Binds to bacterial lipopolysaccharides (LPS), has antibacterial activity.
Gene Name
CAMP
Uniprot ID
P49913
Uniprot Name
Cathelicidin antimicrobial peptide
Molecular Weight
19301.175 Da
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:17139284]
  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:17016423]
  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:10592235]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Ribosomal small subunit binding
Specific Function
Major role in the synthesis of nucleoside triphosphates other than ATP. The ATP gamma phosphate is transferred to the NDP beta phosphate via a ping-pong mechanism, using a phosphorylated active-sit...
Gene Name
NME1
Uniprot ID
P15531
Uniprot Name
Nucleoside diphosphate kinase A
Molecular Weight
17148.635 Da
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:17139284]
  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:17016423]
  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:10592235]
Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
Unknown
General Function
Nadh dehydrogenase activity
Specific Function
Decomposes formic acid to hydrogen and carbon dioxide under anaerobic conditions in the absence of exogenous electron acceptors.
Gene Name
fdhF
Uniprot ID
P07658
Uniprot Name
Formate dehydrogenase H
Molecular Weight
79373.25 Da
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:17139284]
  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:17016423]
Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
Unknown
General Function
Selenocysteine lyase activity
Specific Function
Cysteine desulfurases mobilize the sulfur from L-cysteine to yield L-alanine, an essential step in sulfur metabolism for biosynthesis of a variety of sulfur-containing biomolecules. Component of th...
Gene Name
sufS
Uniprot ID
P77444
Uniprot Name
Cysteine desulfurase
Molecular Weight
44433.435 Da
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:17139284]
  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:17016423]

Drug created on June 13, 2005 07:24 / Updated on November 09, 2017 03:12