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Showing metabocard for Trypanothione disulfide (HMDB0060521)

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IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesenzymes (3) Show 3 proteinsXML
enzymes (3) Show 3 proteins
Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2013-05-17 01:26:59 UTC
Update Date2019-07-23 07:14:31 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
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
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
Not Available
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 Solubility0.14 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
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-053u-7100019100-67d14bf848030745235fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0kbf-0000179500-5d20552d71c5cbd43050Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-06ry-1100196000-2b5e75bbd30591c5bbc6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0nmi-3300794000-382c04c396fcf7329657Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0uk9-0100001900-197058ecbcb39be15dd2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0zmi-0400094600-c0b639c7f85e6cdccaeaSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0005-9800560000-a39d22ea2c5a872f8ed9Spectrum
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
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

Enzyme Details
1. Ribonucleoside-diphosphate reductase large subunit
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
Enzyme Details
2. Ribonucleoside-diphosphate reductase subunit M2
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
Enzyme Details
3. Ribonucleoside-diphosphate reductase subunit M2 B
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