Hmdb loader
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2013-05-17 01:26:59 UTC
Update Date2022-03-07 03:17:46 UTC
HMDB IDHMDB0060521
Secondary Accession Numbers
  • HMDB60521
Metabolite Identification
Common NameTrypanothione disulfide
DescriptionTrypanothione disulfide, also known as oxidized trypanothione or TSST, belongs to the class of organic compounds known as cyclic peptides. Cyclic peptides are compounds containing a cyclic moiety bearing a peptide backbone. Trypanothione disulfide is a very strong basic compound (based on its pKa). Trypanothione disulfide exists in all living organisms, ranging from bacteria to humans. These are compounds containing a cyclic moiety bearing a peptide backbone.
Structure
Data?1563866071
Synonyms
ValueSource
2-AMINO-4-[4-(4-amino-4-carboxy-butyrylamino)-5,8,19,22-tetraoxo-1,2-dithia-6,9,13,18,21-pentaaza-cyclotetracos-23-ylcarbamoyl]-butyrIC ACIDChEBI
Oxidized trypanothioneChEBI
TrypanothiondisulfidChEBI
TSSTChEBI
2-AMINO-4-[4-(4-amino-4-carboxy-butyrylamino)-5,8,19,22-tetraoxo-1,2-dithia-6,9,13,18,21-pentaaza-cyclotetracos-23-ylcarbamoyl]-butyrateGenerator
TrypanothiondisulphidGenerator
Trypanothione disulphideGenerator
N(1),N(8)-Bis(gamma-glu-hemi-cys-gly)sperimidineHMDB
N(1),N(8)-Bis(gamma-glutamyl-hemicystinyl-glycyl)spermidineHMDB
DethiotrypanothioneHMDB
TrypanothioneHMDB
Chemical FormulaC27H47N9O10S2
Average Molecular Weight721.846
Monoisotopic Molecular Weight721.288730149
IUPAC Name(2S)-2-amino-4-{[(4R,23R)-23-{[(4S)-4-amino-4-carboxy-1-hydroxybutylidene]amino}-5,8,19,22-tetrahydroxy-1,2-dithia-6,9,13,18,21-pentaazacyclotetracosa-5,8,18,21-tetraen-4-yl]-C-hydroxycarbonimidoyl}butanoic acid
Traditional Nametrypanothione
CAS Registry NumberNot Available
SMILES
[H][C@](N)(CCC(O)=N[C@@]1([H])CSSC[C@]([H])(N=C(O)CC[C@]([H])(N)C(O)=O)C(O)=NCC(O)=NCCCNCCCCN=C(O)CN=C1O)C(O)=O
InChI Identifier
InChI=1S/C27H47N9O10S2/c28-16(26(43)44)4-6-20(37)35-18-14-47-48-15-19(36-21(38)7-5-17(29)27(45)46)25(42)34-13-23(40)32-11-3-9-30-8-1-2-10-31-22(39)12-33-24(18)41/h16-19,30H,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 KeyLZMSXDHGHZKXJD-VJANTYMQSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as cyclic peptides. Cyclic peptides are compounds containing a cyclic moiety bearing a peptide backbone.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentCyclic peptides
Alternative Parents
Substituents
  • Cyclic alpha peptide
  • Alpha-amino acid
  • Alpha-amino acid or derivatives
  • L-alpha-amino acid
  • Heterocyclic fatty acid
  • Dicarboxylic acid or derivatives
  • Fatty acyl
  • Fatty acid
  • Cyclic carboximidic acid
  • Amino acid or derivatives
  • Amino acid
  • Organic disulfide
  • Carboximidic acid
  • Carboximidic acid derivative
  • Carboxylic acid
  • Secondary aliphatic amine
  • Azacycle
  • Organoheterocyclic compound
  • Polyol
  • Secondary amine
  • Propargyl-type 1,3-dipolar organic compound
  • Organic 1,3-dipolar compound
  • Hydrocarbon derivative
  • Amine
  • Organopnictogen compound
  • Primary aliphatic amine
  • Carbonyl group
  • Organonitrogen compound
  • Organooxygen compound
  • Primary amine
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organic oxide
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
DispositionNot Available
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.14 g/LALOGPS
logP-2.1ALOGPS
logP-4.4ChemAxon
logS-3.7ALOGPS
pKa (Strongest Acidic)3.34ChemAxon
pKa (Strongest Basic)10.65ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count19ChemAxon
Hydrogen Donor Count11ChemAxon
Polar Surface Area334.21 ŲChemAxon
Rotatable Bond Count10ChemAxon
Refractivity178.35 m³·mol⁻¹ChemAxon
Polarizability73.51 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+262.18631661259
DarkChem[M-H]-250.97331661259
DeepCCS[M+H]+259.25830932474
DeepCCS[M-H]-257.36330932474
DeepCCS[M-2H]-291.37530932474
DeepCCS[M+Na]+265.39130932474
AllCCS[M+H]+255.232859911
AllCCS[M+H-H2O]+254.932859911
AllCCS[M+NH4]+255.432859911
AllCCS[M+Na]+255.432859911
AllCCS[M-H]-232.332859911
AllCCS[M+Na-2H]-234.932859911
AllCCS[M+HCOO]-237.832859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Trypanothione disulfide[H][C@](N)(CCC(O)=N[C@@]1([H])CSSC[C@]([H])(N=C(O)CC[C@]([H])(N)C(O)=O)C(O)=NCC(O)=NCCCNCCCCN=C(O)CN=C1O)C(O)=O5715.6Standard polar33892256
Trypanothione disulfide[H][C@](N)(CCC(O)=N[C@@]1([H])CSSC[C@]([H])(N=C(O)CC[C@]([H])(N)C(O)=O)C(O)=NCC(O)=NCCCNCCCCN=C(O)CN=C1O)C(O)=O5431.9Standard non polar33892256
Trypanothione disulfide[H][C@](N)(CCC(O)=N[C@@]1([H])CSSC[C@]([H])(N=C(O)CC[C@]([H])(N)C(O)=O)C(O)=NCC(O)=NCCCNCCCCN=C(O)CN=C1O)C(O)=O6592.3Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Trypanothione disulfide GC-MS (Non-derivatized) - 70eV, Positivesplash10-053u-7100019100-67d14bf848030745235f2017-11-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Trypanothione disulfide GC-MS (TMS_1_1) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Trypanothione disulfide GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Trypanothione disulfide GC-MS (TMS_1_3) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Trypanothione disulfide GC-MS (TMS_1_4) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Trypanothione disulfide GC-MS (TMS_1_5) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Trypanothione disulfide GC-MS (TMS_1_6) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Trypanothione disulfide GC-MS (TMS_1_7) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Trypanothione disulfide GC-MS (TMS_1_8) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Trypanothione disulfide GC-MS (TMS_1_9) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Trypanothione disulfide GC-MS (TMS_1_10) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Trypanothione disulfide GC-MS (TMS_1_11) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Trypanothione disulfide GC-MS (TMS_2_1) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Trypanothione disulfide GC-MS (TMS_2_2) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Trypanothione disulfide GC-MS (TMS_2_3) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Trypanothione disulfide GC-MS (TMS_2_4) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Trypanothione disulfide GC-MS (TMS_2_5) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Trypanothione disulfide GC-MS (TMS_2_6) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Trypanothione disulfide GC-MS (TMS_2_7) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Trypanothione disulfide GC-MS (TMS_2_8) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Trypanothione disulfide GC-MS (TMS_2_9) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Trypanothione disulfide GC-MS (TMS_2_10) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Trypanothione disulfide GC-MS (TMS_2_11) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Trypanothione disulfide GC-MS (TMS_2_12) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Trypanothione disulfide GC-MS (TMS_2_13) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Trypanothione disulfide 10V, Positive-QTOFsplash10-0kbf-0000179500-5d20552d71c5cbd430502017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Trypanothione disulfide 20V, Positive-QTOFsplash10-06ry-1100196000-2b5e75bbd30591c5bbc62017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Trypanothione disulfide 40V, Positive-QTOFsplash10-0nmi-3300794000-382c04c396fcf73296572017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Trypanothione disulfide 10V, Negative-QTOFsplash10-0uk9-0100001900-197058ecbcb39be15dd22017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Trypanothione disulfide 20V, Negative-QTOFsplash10-0zmi-0400094600-c0b639c7f85e6cdccaea2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Trypanothione disulfide 40V, Negative-QTOFsplash10-0005-9800560000-a39d22ea2c5a872f8ed92017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Trypanothione disulfide 10V, Positive-QTOFsplash10-00di-0000011900-ce30db955e74999d77102021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Trypanothione disulfide 20V, Positive-QTOFsplash10-01r6-0000491100-35987143acca605130382021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Trypanothione disulfide 40V, Positive-QTOFsplash10-001r-9500141000-1319ae3cd7bc2c2de3752021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Trypanothione disulfide 10V, Negative-QTOFsplash10-0udi-0000000900-e01b2c446e994246b5642021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Trypanothione disulfide 20V, Negative-QTOFsplash10-0fka-2900036500-83520fad0f0254e68d4c2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Trypanothione disulfide 40V, Negative-QTOFsplash10-0007-7900000000-341c6c3d09aa94004b922021-10-12Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
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 IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID102998
KEGG Compound IDC03170
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound115098
PDB IDNot Available
ChEBI ID35490
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents 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 ]

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