Record Information
Version 1.0
Update Date 1/22/2018 12:54:54 PM
Metabolite IDPAMDB001689
Identification
Name: Selenodiglutathione
Description:Selenodiglutathione 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 Pseudomonas aeruginosa [PMID:1569062]
Structure
Thumb
Synonyms:
  • GSSeSG
Chemical Formula: C20H32N6O12S2Se
Average Molecular Weight: 691.59
Monoisotopic Molecular Weight: 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
Taxonomy DescriptionThis compound belongs to the class of organic compounds 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.
Kingdom Organic compounds
Super ClassOrganic acids and derivatives
Class Carboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct Parent Peptides
Alternative Parents
Substituents
  • Alpha peptide
  • N-acyl-aliphatic-alpha amino acid
  • Tetracarboxylic acid or derivatives
  • N-acyl-alpha amino acid or derivatives
  • N-acyl-alpha-amino acid
  • L-alpha-amino acid
  • D-alpha-amino acid
  • Alpha-amino acid or derivatives
  • Alpha-amino acid
  • Amino fatty acid
  • Fatty acyl
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Sulfenyl compound
  • Carboxylic acid
  • Carboximidic acid derivative
  • Carboximidic acid
  • Hydrocarbon derivative
  • Primary amine
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Carbonyl group
  • Amine
  • Aliphatic acyclic compound
Molecular Framework Aliphatic acyclic compounds
External Descriptors
Physical Properties
State: Not Available
Charge:-1
Melting point: Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility1.23 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count22ChemAxon
Refractivity149.77 m3·mol-1ChemAxon
Polarizability59.38 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Cytoplasm
Reactions:
Pathways: Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
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
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 IDNot Available
Pubchem Compound ID108069
Kegg IDC18870
ChemSpider ID97171
Wikipedia IDNot Available
BioCyc IDCPD-13908
EcoCyc IDCPD-13908

Enzymes

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
Locus Tag:
PA5240
Molecular weight:
11.9 kDa