Selenocysteine

Identification

Generic Name
Selenocysteine
DrugBank Accession Number
DB02345
Background

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]

Type
Small Molecule
Groups
Experimental
Structure
Thumb
Weight
Average: 168.05
Monoisotopic: 168.964200301
Chemical Formula
C3H7NO2Se
Synonyms
  • 3-selenyl-L-alanine
  • L-selenocysteine
  • Selenium cysteine

Pharmacology

Indication

Not Available

Pharmacology
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Contraindications & Blackbox Warnings
Contraindications
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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UCathelicidin antimicrobial peptideNot AvailableHumans
UNucleoside diphosphate kinase ANot AvailableHumans
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

Adverse Effects
Medicalerrors
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Toxicity

Not Available

Pathways
PathwayCategory
Selenoamino Acid MetabolismMetabolic
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
EltrombopagThe bioavailability of Selenocysteine can be decreased when combined with Eltrombopag.
Interactions
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Food Interactions
Not Available

Products

Products
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Active Moieties
NameKindUNIICASInChI Key
SeleniumunknownH6241UJ22B7782-49-2BUGBHKTXTAQXES-UHFFFAOYSA-N
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
Dialyvite 3000Selenocysteine (70 ug/1) + Ascorbic acid (100 mg/1) + Biotin (300 ug/1) + Cobalamin (1 mg/1) + Folic acid (3 mg/1) + Nicotinamide (20 mg/1) + Calcium pantothenate (10 mg/1) + Pyridoxine hydrochloride (25 mg/1) + Riboflavin (1.7 mg/1) + Thiamine mononitrate (1.5 mg/1) + Zinc citrate (15 mg/1) + alpha-Tocopherol succinate (30 [iU]/1)Tablet, coatedOralHillestad Pharmaceuticals Usa2004-02-01Not applicableUS flag
Dialyvite 5000Selenocysteine (70 ug/1) + Ascorbic acid (100 mg/1) + Biotin (300 ug/1) + Cobalamin (2 mg/1) + Folic acid (5 mg/1) + Nicotinamide (20 mg/1) + Calcium pantothenate (10 mg/1) + Pyridoxine hydrochloride (50 mg/1) + Riboflavin (1.7 mg/1) + Thiamine mononitrate (1.5 mg/1) + Zinc citrate (25 mg/1) + alpha-Tocopherol succinate (30 [iU]/1)Tablet, coatedOralHillestad Pharmaceuticals Usa2008-05-01Not applicableUS flag
Dialyvite Supreme DSelenocysteine (70 ug/1) + Ascorbic acid (100 mg/1) + Biotin (300 ug/1) + Cholecalciferol (2000 [iU]/1) + Cobalamin (1 mg/1) + Folic acid (3 mg/1) + Nicotinamide (20 mg/1) + Calcium pantothenate (10 mg/1) + Pyridoxine hydrochloride (25 mg/1) + Riboflavin (1.7 mg/1) + Thiamine mononitrate (1.5 mg/1) + Zinc citrate (15 mg/1) + alpha-Tocopherol succinate (30 [iU]/1)Tablet, coatedOralHillestad Pharmaceuticals Usa2010-09-08Not applicableUS flag

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
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
Aliphatic acyclic compound / Amine / Amino acid / Carbonyl group / Carboxylic acid / Hydrocarbon derivative / L-alpha-amino acid / Monocarboxylic acid or derivatives / Organic nitrogen compound / Organic oxide
Molecular Framework
Aliphatic acyclic compounds
External Descriptors
proteinogenic amino acid, L-alpha-amino acid, L-alanine derivative, selenocysteine (CHEBI:16633) / Other amino acids (C05688)
Affected organisms
Not Available

Chemical Identifiers

UNII
0CH9049VIS
CAS number
10236-58-5
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[C@@H](C[SeH])C(O)=O

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. [Article]
Human Metabolome Database
HMDB0003288
KEGG Compound
C05688
PubChem Compound
6326983
PubChem Substance
46508133
ChemSpider
23436
RxNav
1549332
ChEBI
16633
ChEMBL
CHEMBL109962
PDBe Ligand
SEC
Wikipedia
Selenocysteine
PDB Entries
1aa6 / 1cc1 / 1fdi / 1fdo / 1h0h / 1kmk / 1kqf / 1kqg / 1pae / 1pfp
show 51 more

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
Tablet, coatedOral
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

Targets

Drugtargets
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Kind
Protein
Organism
Humans
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. [Article]
  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. [Article]
  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. [Article]
Kind
Protein
Organism
Humans
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. [Article]
  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. [Article]
  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. [Article]
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. [Article]
  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. [Article]
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. [Article]
  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. [Article]

Drug created on June 13, 2005 13:24 / Updated on July 02, 2020 13:15