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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2013-05-17 01:26:51 UTC
Update Date2019-07-23 07:14:31 UTC
HMDB IDHMDB0060520
Secondary Accession Numbers
  • HMDB60520
Metabolite Identification
Common NameTrypanothione
DescriptionLeishmaniasis is a neglected disease caused by Leishmania, an intracellular protozoan parasite which possesses a unique thiol metabolism based on trypanothione. (PMID: 22928053 ) Trypanosomatids, the causative agents of several tropical diseases, rely on trypanothione as principal low molecular mass thiol, and their glutaredoxins readily react with the unique bis(glutathionyl) spermidine conjugate. (PMID: 22978520 ) Among the potential molecular target, Trypanothione reductase (TR) is considered an ideal enzyme since it is involved in the unique thiol-based metabolism observed in the Trypanosomatidae family and is a validated target for the search of antitrypanosomatidae drugs. (PMID: 23410156 )
Structure
Data?1563866071
Synonyms
ValueSource
(2S,7R,26R,31S)-2,31-Diamino-7,26-bis(mercaptomethyl)-5,8,11,22,25,28-hexaoxo-6,9,12,16,21,24,27-heptaazadotriacontane-1,32-dioic acidChEBI
BIS(GAMMA-glutamyl-cysteinyl-glycinyl)spermidineChEBI
N1,N8-Bis(gamma-L-glutamyl-L-cysteinyl-glycyl)spermidineChEBI
N1,N8-Bis(glutathionyl)spermidineChEBI
N1,N8-Bis-(gamma-L-glutamyl-L-cysteinyl-glycyl)-spermidineChEBI
N1,N8-Bis-(glutathionyl)spermidineChEBI
Reduced trypanothioneChEBI
TrypanothionChEBI
TSHChEBI
(2S,7R,26R,31S)-2,31-Diamino-7,26-bis(mercaptomethyl)-5,8,11,22,25,28-hexaoxo-6,9,12,16,21,24,27-heptaazadotriacontane-1,32-dioateGenerator
BIS(g-glutamyl-cysteinyl-glycinyl)spermidineGenerator
BIS(γ-glutamyl-cysteinyl-glycinyl)spermidineGenerator
N1,N8-Bis(g-L-glutamyl-L-cysteinyl-glycyl)spermidineGenerator
N1,N8-Bis(γ-L-glutamyl-L-cysteinyl-glycyl)spermidineGenerator
N1,N8-Bis-(g-L-glutamyl-L-cysteinyl-glycyl)-spermidineGenerator
N1,N8-Bis-(γ-L-glutamyl-L-cysteinyl-glycyl)-spermidineGenerator
Chemical FormulaC27H49N9O10S2
Average Molecular Weight723.862
Monoisotopic Molecular Weight723.304380213
IUPAC Name(2S)-2-amino-4-{[(1R)-1-{[({3-[(4-{2-[(2R)-2-[(4S)-4-amino-4-carboxybutanamido]-3-sulfanylpropanamido]acetamido}butyl)amino]propyl}carbamoyl)methyl]carbamoyl}-2-sulfanylethyl]carbamoyl}butanoic acid
Traditional Nametrypanothione
CAS Registry NumberNot Available
SMILES
N[C@@H](CCC(=O)N[C@@H](CS)C(=O)NCC(=O)NCCCCNCCCNC(=O)CNC(=O)[C@H](CS)NC(=O)CC[C@H](N)C(O)=O)C(O)=O
InChI Identifier
InChI=1S/C27H49N9O10S2/c28-16(26(43)44)4-6-20(37)35-18(14-47)24(41)33-12-22(39)31-10-2-1-8-30-9-3-11-32-23(40)13-34-25(42)19(15-48)36-21(38)7-5-17(29)27(45)46/h16-19,30,47-48H,1-15,28-29H2,(H,31,39)(H,32,40)(H,33,41)(H,34,42)(H,35,37)(H,36,38)(H,43,44)(H,45,46)/t16-,17-,18-,19-/m0/s1
InChI KeyPHDOXVGRXXAYEB-VJANTYMQSA-N
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
  • Dicarboxylic acid or derivatives
  • N-acyl-amine
  • Fatty acid
  • Fatty acyl
  • Amino acid or derivatives
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Amino acid
  • Carboxylic acid
  • Secondary amine
  • Alkylthiol
  • Secondary aliphatic amine
  • 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
Ontology
Role

Industrial application:

Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.061 g/LALOGPS
logP-2.7ALOGPS
logP-11ChemAxon
logS-4.8ALOGPS
pKa (Strongest Acidic)1.64ChemAxon
pKa (Strongest Basic)10.57ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count13ChemAxon
Hydrogen Donor Count13ChemAxon
Polar Surface Area313.27 ŲChemAxon
Rotatable Bond Count27ChemAxon
Refractivity176.8 m³·mol⁻¹ChemAxon
Polarizability75.33 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-004l-3155429000-d5231bbd946878919665Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-052f-0051947300-86c5cd19a4c81cf0b5abSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a5c-0474921000-8dbbcaa8dc36b7d968c2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-1794600000-e182697b3ee946d82ce4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0fnl-1010309600-94fcb779fb85d179bbfeSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0k97-1242958600-89da9e05080a52b5cc90Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0007-7924845000-81780b2616d57803a2eaSpectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB03470
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID396023
KEGG Compound IDC02090
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkTrypanothione
METLIN IDNot Available
PubChem Compound449517
PDB IDNot Available
ChEBI ID17842
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Magrane M: UniProt Knowledgebase: a hub of integrated protein data. Database (Oxford). 2011 Mar 29;2011:bar009. doi: 10.1093/database/bar009. Print 2011. [PubMed:21447597 ]
  2. Fiorillo A, Colotti G, Boffi A, Baiocco P, Ilari A: The crystal structures of the tryparedoxin-tryparedoxin peroxidase couple unveil the structural determinants of Leishmania detoxification pathway. PLoS Negl Trop Dis. 2012;6(8):e1781. doi: 10.1371/journal.pntd.0001781. Epub 2012 Aug 21. [PubMed:22928053 ]
  3. Comini MA, Krauth-Siegel RL, Bellanda M: Mono- and dithiol glutaredoxins in the trypanothione-based redox metabolism of pathogenic trypanosomes. Antioxid Redox Signal. 2013 Sep 1;19(7):708-22. doi: 10.1089/ars.2012.4932. Epub 2012 Oct 25. [PubMed:22978520 ]
  4. Bernardes LS, Zani CL, Carvalho I: Trypanosomatidae diseases: from the current therapy to the efficacious role of trypanothione reductase in drug discovery. Curr Med Chem. 2013;20(21):2673-96. [PubMed:23410156 ]

Enzymes

General function:
Involved in oxidation reduction
Specific function:
Provides the precursors necessary for DNA synthesis. Catalyzes the biosynthesis of deoxyribonucleotides from the corresponding ribonucleotides.
Gene Name:
RRM1
Uniprot ID:
P23921
Molecular weight:
90069.375
Reactions
2'-Deoxyribonucleoside diphosphate + Trypanothione disulfide + Water → Ribonucleoside diphosphate + Trypanothionedetails
General function:
Involved in oxidoreductase activity
Specific function:
Provides the precursors necessary for DNA synthesis. Catalyzes the biosynthesis of deoxyribonucleotides from the corresponding ribonucleotides. Inhibits Wnt signaling.
Gene Name:
RRM2
Uniprot ID:
P31350
Molecular weight:
44877.25
Reactions
2'-Deoxyribonucleoside diphosphate + Trypanothione disulfide + Water → Ribonucleoside diphosphate + Trypanothionedetails
General function:
Involved in oxidoreductase activity
Specific function:
Plays a pivotal role in cell survival by repairing damaged DNA in a p53/TP53-dependent manner. Supplies deoxyribonucleotides for DNA repair in cells arrested at G1 or G2. Contains an iron-tyrosyl free radical center required for catalysis. Forms an active ribonucleotide reductase (RNR) complex with RRM1 which is expressed both in resting and proliferating cells in response to DNA damage.
Gene Name:
RRM2B
Uniprot ID:
Q7LG56
Molecular weight:
48786.6
Reactions
2'-Deoxyribonucleoside diphosphate + Trypanothione disulfide + Water → Ribonucleoside diphosphate + Trypanothionedetails