Selenodiglutathione (ECMDB21283) (M2MDB001689)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes (1)XML
Proteins (1)
Record Information
Version2.0
Creation Date2012-07-30 14:55:12 -0600
Update Date2015-06-03 17:21:04 -0600
Secondary Accession Numbers
  • ECMDB21283
Identification
Name:Selenodiglutathione
DescriptionSelenodiglutathione is a member of the chemical class known as Peptides. These are compounds containing an amide derived from two or more amino carboxylic acid molecules (the same or different) by formation of a covalent bond from the carbonyl carbon of one to the nitrogen atom of another. Selenium compounds like selenite (SeO3(2-) may form a covalent adduct with glutathione (GSH) in the form of selenodiglutathione (GS-Se-SG), which is assumed to be important in the metabolism of selenium. GS-Se-SG to be a very efficient oxidant of reduced thioredoxin from E. coli [PMID:1569062]
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms:
  • GSSeSG
Chemical Formula:C20H32N6O12S2Se
Weight:Average: 691.59
Monoisotopic: 692.068483726
InChI Key:GJEZZQVPWMCGSB-BJDJZHNGSA-N
InChI:InChI=1S/C20H32N6O12S2Se/c21-9(19(35)36)1-3-13(27)25-11(17(33)23-5-15(29)30)7-39-41-40-8-12(18(34)24-6-16(31)32)26-14(28)4-2-10(22)20(37)38/h9-12H,1-8,21-22H2,(H,23,33)(H,24,34)(H,25,27)(H,26,28)(H,29,30)(H,31,32)(H,35,36)(H,37,38)/t9-,10-,11-,12-/m0/s1
CAS number:33944-90-0
IUPAC Name:(2S)-2-amino-4-{[(1R)-2-[({[(2R)-2-[(4S)-4-amino-4-carboxybutanamido]-2-[(carboxymethyl)carbamoyl]ethyl]sulfanyl}selanyl)sulfanyl]-1-[(carboxymethyl)carbamoyl]ethyl]carbamoyl}butanoic acid
Traditional IUPAC Name:(2S)-2-amino-4-{[(1R)-2-[({[(2R)-2-[(4S)-4-amino-4-carboxybutanamido]-2-(carboxymethylcarbamoyl)ethyl]sulfanyl}selanyl)sulfanyl]-1-(carboxymethylcarbamoyl)ethyl]carbamoyl}butanoic acid
SMILES:N[C@@H](CCC(=O)N[C@@H](CS[Se]SC[C@H](NC(=O)CC[C@H](N)C(O)=O)C(=O)NCC(O)=O)C(=O)NCC(O)=O)C(O)=O
Chemical Taxonomy
Description belongs to the class of organic compounds known as peptides. Peptides are compounds containing an amide derived from two or more amino carboxylic acid molecules (the same or different) by formation of a covalent bond from the carbonyl carbon of one to the nitrogen atom of another.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentPeptides
Alternative Parents
Substituents
  • Alpha peptide
  • N-acyl-alpha-amino acid
  • N-acyl-alpha amino acid or derivatives
  • Tetracarboxylic acid or derivatives
  • Alpha-amino acid
  • Alpha-amino acid or derivatives
  • L-alpha-amino acid
  • Amino acid or derivatives
  • Amino acid
  • Carboximidic acid
  • Carboximidic acid derivative
  • Carboxylic acid
  • Thioselenide
  • Organic 1,3-dipolar compound
  • Sulfenyl compound
  • Propargyl-type 1,3-dipolar organic compound
  • Organonitrogen compound
  • Amine
  • Organic oxide
  • Primary aliphatic amine
  • Organic oxygen compound
  • Organic nitrogen compound
  • Organooxygen compound
  • Organosulfur compound
  • Hydrocarbon derivative
  • Primary amine
  • Organopnictogen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
State:Not Available
Charge:-1
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility1.23 g/LALOGPS
logP-3.5ALOGPS
logP-11ChemAxon
logS-2.8ALOGPS
pKa (Strongest Acidic)0.94ChemAxon
pKa (Strongest Basic)9.61ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count14ChemAxon
Hydrogen Donor Count10ChemAxon
Polar Surface Area317.64 ŲChemAxon
Rotatable Bond Count22ChemAxon
Refractivity149.77 m³·mol⁻¹ChemAxon
Polarizability59.38 ųChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
Selenite + Glutathione + Hydrogen ion > Selenodiglutathione + Glutathione disulfide + Water
SMPDB Pathways:
Selenium metabolismPW001894 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:Not Available
EcoCyc Pathways:Not Available
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_8) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0007-0101019000-9857207f378f121fb280View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004l-2312397000-efd9097b56e99aef6aa4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9200372000-2d3b186ee1356ec79b1cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0112129000-152b32625eb60b0b830fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00fs-1123219000-bf46b86caf565603a9f5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00di-9020213000-e23d94231501a0008492View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0000009000-4b98da6640c686ea20abView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-2242019000-ed4b235f6c177fad9465View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0udj-2903013000-72586ad9d81689161ce4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0000009000-e2a2768af9acb19ae899View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-02di-0000389000-adadf678a410bf6fe817View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-053r-9300032000-02628f78f1b468460e32View in MoNA
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
References
References:
  • Bjornstedt, M., Kumar, S., Holmgren, A. (1992). "Selenodiglutathione is a highly efficient oxidant of reduced thioredoxin and a substrate for mammalian thioredoxin reductase." J Biol Chem 267:8030-8034. Pubmed: 1569062
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI ID26634
HMDB IDHMDB0304484
Pubchem Compound ID108069
Kegg IDC18870
ChemSpider ID97171
Wikipedia IDNot Available
BioCyc IDCPD-13908
EcoCyc IDCPD-13908

Enzymes

Protein Details
1. Thioredoxin-1
General function:
Involved in electron carrier activity
Specific function:
Participates in various redox reactions through the reversible oxidation of its active center dithiol to a disulfide and catalyzes dithiol-disulfide exchange reactions
Gene Name:
trxA
Uniprot ID:
P0AA25
Molecular weight:
11807