Glutathionylspermidine (ECMDB20155) (M2MDB001002)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes (1)XML
Proteins (30)
Record Information
Version2.0
Creation Date2012-05-31 14:30:22 -0600
Update Date2015-06-03 17:19:25 -0600
Secondary Accession Numbers
  • ECMDB20155
Identification
Name:Glutathionylspermidine
DescriptionGlutathionylspermidine is a member of the chemical class known as 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). Glutathionylspermidine (Gsp) is a metabolite common to Escherichia coli and protozoal parasites of the Trypanosoma family. (PMID 9398217) Glutathionylspermidine is an intermediate formed in the biosynthesis of trypanothione, an essential metabolite in defence against chemical and oxidative stress in the Kinetoplastida. (PMID 18959765) Glutathionylspermidine is formed as end product and the enzyme lacks TryS activity. (PMID 12049631)
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms:
  • GSH-spermidine
  • N1-(γ-L-glutamyl-L-cysteinyl-glycyl)-spermidine
  • N1-(g-L-Glutamyl-L-cysteinyl-glycyl)-spermidine
  • N1-(gamma-L-Glutamyl-L-cysteinyl-glycyl)-spermidine
  • N1-(γ-L-Glutamyl-L-cysteinyl-glycyl)-spermidine
Chemical Formula:C17H34N6O5S
Weight:Average: 434.554
Monoisotopic: 434.231138918
InChI Key:NEDQLXHBVHSKNV-STQMWFEESA-N
InChI:InChI=1S/C17H34N6O5S/c18-6-1-2-7-20-8-3-9-21-15(25)10-22-16(26)13(11-29)23-14(24)5-4-12(19)17(27)28/h12-13,20,29H,1-11,18-19H2,(H,21,25)(H,22,26)(H,23,24)(H,27,28)/t12-,13-/m0/s1
CAS number:33932-35-3
IUPAC Name:(2S)-2-amino-4-{[(1R)-1-{[({3-[(4-aminobutyl)amino]propyl}-C-hydroxycarbonimidoyl)methyl]-C-hydroxycarbonimidoyl}-2-sulfanylethyl]-C-hydroxycarbonimidoyl}butanoic acid
Traditional IUPAC Name:glutathionylspermidine
SMILES:[H][C@](N)(CCC(O)=N[C@@]([H])(CS)C(O)=NCC(O)=NCCCNCCCCN)C(O)=O
Chemical Taxonomy
Description belongs to the class of organic compounds known as oligopeptides. These are organic compounds containing a sequence of between three and ten alpha-amino acids joined by peptide bonds.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentOligopeptides
Alternative Parents
Substituents
  • Alpha-oligopeptide
  • Glutamine or derivatives
  • N-acyl-alpha amino acid or derivatives
  • Alpha-amino acid amide
  • Cysteine or derivatives
  • Alpha-amino acid
  • N-substituted-alpha-amino acid
  • L-alpha-amino acid
  • Alpha-amino acid or derivatives
  • Fatty amide
  • N-acyl-amine
  • Fatty acid
  • Fatty acyl
  • Amino acid or derivatives
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Amino acid
  • Secondary amine
  • Carboxylic acid
  • Secondary aliphatic amine
  • Monocarboxylic acid or derivatives
  • Alkylthiol
  • Organic nitrogen compound
  • Primary aliphatic amine
  • Organonitrogen compound
  • Organooxygen compound
  • Organosulfur compound
  • Carbonyl group
  • Primary amine
  • Amine
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
State:Not Available
Charge:3
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility0.1 g/LALOGPS
logP-1.6ALOGPS
logP-8.3ChemAxon
logS-3.6ALOGPS
pKa (Strongest Acidic)1.88ChemAxon
pKa (Strongest Basic)10.89ChemAxon
Physiological Charge3ChemAxon
Hydrogen Acceptor Count11ChemAxon
Hydrogen Donor Count8ChemAxon
Polar Surface Area199.14 ŲChemAxon
Rotatable Bond Count17ChemAxon
Refractivity112.45 m³·mol⁻¹ChemAxon
Polarizability47.62 ųChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
Adenosine triphosphate + Glutathione + Spermidine <> ADP + Glutathionylspermidine + Hydrogen ion + Phosphate
Glutathionylspermidine + Water <> Glutathione + Spermidine
Adenosine triphosphate + Glutathione + Spermidine <> ADP + Phosphate + Glutathionylspermidine
Glutathionylspermidine + Water > Glutathione + Spermidine
Spermidine + Glutathione + Adenosine triphosphate > Hydrogen ion + Glutathionylspermidine + ADP + Phosphate
Glutathione + Spermidine + Adenosine triphosphate > Glutathionylspermidine + ADP + Inorganic phosphate
SMPDB Pathways:
Glutathione metabolismPW000833 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:
EcoCyc Pathways:Not Available
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_5_101) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0uy0-2797700000-4f8f3cc7a27c488f8ef2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0kbf-4941000000-2007d3e54aec69deb376View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0pkc-6930000000-fe57ee018163812b5223View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-2446900000-09ea7b8829f2e9e03befView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0f7p-3794300000-4dd1911112b9673f5c44View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-006x-9610000000-fe321383486fb6cf6cb3View 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:
  • Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
  • Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
  • Lin, C. H., Kwon, D. S., Bollinger, J. M. Jr, Walsh, C. T. (1997). "Evidence for a glutathionyl-enzyme intermediate in the amidase activity of the bifunctional glutathionylspermidine synthetase/amidase from Escherichia coli." Biochemistry 36:14930-14938. Pubmed: 9398217
  • Oza, S. L., Ariyanayagam, M. R., Fairlamb, A. H. (2002). "Characterization of recombinant glutathionylspermidine synthetase/amidase from Crithidia fasciculata." Biochem J 364:679-686. Pubmed: 12049631
  • Oza, S. L., Chen, S., Wyllie, S., Coward, J. K., Fairlamb, A. H. (2008). "ATP-dependent ligases in trypanothione biosynthesis--kinetics of catalysis and inhibition by phosphinic acid pseudopeptides." FEBS J 275:5408-5421. Pubmed: 18959765
  • van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195
  • Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. Pubmed: 18331064
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI ID16613
HMDB IDNot Available
Pubchem Compound ID440772
Kegg IDC05730
ChemSpider ID142094
Wikipedia IDNot Available
BioCyc IDGLUTATHIONYLSPERMIDINE
EcoCyc IDGLUTATHIONYLSPERMIDINE
Ligand ExpoTS5

Enzymes

Protein Details
1. Bifunctional glutathionylspermidine synthetase/amidase
General function:
Amino acid transport and metabolism
Specific function:
Catalyzes the formation of an amide bond between glutathione and spermidine coupled with hydrolysis of ATP; also catalyzes the hydrolysis of glutathionylspermidine to glutathione and spermidine
Gene Name:
gsp
Uniprot ID:
P0AES0
Molecular weight:
70531
Reactions
Glutathione + spermidine + ATP = glutathionylspermidine + ADP + phosphate.
Glutathionylspermidine + H(2)O = glutathione + spermidine.