Trypanothione

Identification

Name
Trypanothione
Accession Number
DB03470  (EXPT01557)
Type
Small Molecule
Groups
Experimental
Description
Not Available
Structure
Thumb
Synonyms
Not Available
Categories
UNII
Not Available
CAS number
Not Available
Weight
Average: 723.862
Monoisotopic: 723.304380213
Chemical Formula
C27H49N9O10S2
InChI Key
PHDOXVGRXXAYEB-VJANTYMQSA-N
InChI
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
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
SMILES
N[[email protected]@H](CCC(=O)N[[email protected]@H](CS)C(=O)NCC(=O)NCCCCNCCCNC(=O)CNC(=O)[[email protected]](CS)NC(=O)CC[[email protected]](N)C(O)=O)C(O)=O

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UTrypanothione reductaseNot AvailableTrypanosoma cruzi
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

General References
Not Available
External Links
Human Metabolome Database
HMDB60520
KEGG Compound
C02090
PubChem Compound
449517
PubChem Substance
46505609
ChemSpider
396023
ChEBI
17842
HET
GCG
PDB Entries
1bzl / 2wow / 4adw / 4grt

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0121 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count27ChemAxon
Refractivity176.8 m3·mol-1ChemAxon
Polarizability75.33 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption-0.5736
Blood Brain Barrier-0.5543
Caco-2 permeable-0.7962
P-glycoprotein substrateSubstrate0.5538
P-glycoprotein inhibitor INon-inhibitor0.8604
P-glycoprotein inhibitor IINon-inhibitor0.9879
Renal organic cation transporterNon-inhibitor0.9413
CYP450 2C9 substrateNon-substrate0.875
CYP450 2D6 substrateNon-substrate0.7991
CYP450 3A4 substrateNon-substrate0.7351
CYP450 1A2 substrateNon-inhibitor0.8941
CYP450 2C9 inhibitorNon-inhibitor0.9192
CYP450 2D6 inhibitorNon-inhibitor0.9445
CYP450 2C19 inhibitorNon-inhibitor0.9094
CYP450 3A4 inhibitorNon-inhibitor0.9594
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9932
Ames testAMES toxic0.7349
CarcinogenicityNon-carcinogens0.9242
BiodegradationNot ready biodegradable0.5262
Rat acute toxicity1.9668 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9831
hERG inhibition (predictor II)Non-inhibitor0.9012
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This compound 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.
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Carboxylic acids and derivatives
Sub Class
Amino acids, peptides, and analogues
Direct Parent
Oligopeptides
Alternative Parents
Glutamine and derivatives / N-acyl-alpha amino acids and derivatives / Alpha amino acid amides / Cysteine and derivatives / L-alpha-amino acids / Dicarboxylic acids and derivatives / Fatty acids and conjugates / N-acyl amines / Secondary carboxylic acid amides / Amino acids
show 8 more
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
show 25 more
Molecular Framework
Aliphatic acyclic compounds
External Descriptors
glutathione derivative (CHEBI:17842)

Targets

Kind
Protein
Organism
Trypanosoma cruzi
Pharmacological action
Unknown
General Function
Trypanothione-disulfide reductase activity
Specific Function
Trypanothione is the parasite analog of glutathione; this enzyme is the equivalent of glutathione reductase.
Gene Name
TPR
Uniprot ID
P28593
Uniprot Name
Trypanothione reductase
Molecular Weight
53867.475 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]

Drug created on June 13, 2005 07:24 / Updated on November 09, 2017 03:28