Dithioerythritol

Identification

Name
Dithioerythritol
Accession Number
DB01692  (EXPT01292)
Type
Small Molecule
Groups
Experimental
Description

A compound that, along with its isomer, Cleland's reagent (dithiothreitol), is used for the protection of sulfhydryl groups against oxidation to disulfides and for the reduction of disulfides to sulfhydryl groups. [PubChem]

Structure
Thumb
Synonyms
  • (2R,3S)-1,4-dimercaptobutane-2,3-diol
  • (2R*,3S*)-1,4-dimercapto-2,3-butanediol
  • 1,4-dithioerythritol
  • DTE
  • erythro-1,4-Dimercapto-2,3-butanediol
Categories
UNII
Not Available
CAS number
6892-68-8
Weight
Average: 154.251
Monoisotopic: 154.012220944
Chemical Formula
C4H10O2S2
InChI Key
VHJLVAABSRFDPM-ZXZARUISSA-N
InChI
InChI=1S/C4H10O2S2/c5-3(1-7)4(6)2-8/h3-8H,1-2H2/t3-,4+
IUPAC Name
(2R,3S)-1,4-disulfanylbutane-2,3-diol
SMILES
[H][[email protected]](O)(CS)[[email protected]]([H])(O)CS

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UListeriolysin regulatory proteinNot AvailableListeria monocytogenes serovar 1/2a (strain ATCC BAA-679 / EGD-e)
U6,7-dimethyl-8-ribityllumazine synthaseNot AvailableMycobacterium tuberculosis
UThymidine kinase, cytosolicNot AvailableHuman
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
KEGG Compound
C00950
PubChem Compound
439352
PubChem Substance
46509091
ChemSpider
388475
ChEBI
17456
ChEMBL
CHEMBL1232391
HET
DTU
Wikipedia
Dithioerythritol
PDB Entries
1kzi / 1o9j / 1tv8 / 1w19 / 1w4r / 1ywm / 2bgc / 2c92 / 2h00 / 2hp0
show 29 more

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
PropertyValueSource
melting point (°C)83 °CPhysProp
Predicted Properties
PropertyValueSource
Water Solubility5.14 mg/mLALOGPS
logP0.18ALOGPS
logP-0.28ChemAxon
logS-1.5ALOGPS
pKa (Strongest Acidic)9.62ChemAxon
pKa (Strongest Basic)-3.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area40.46 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity38.84 m3·mol-1ChemAxon
Polarizability15.51 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.933
Blood Brain Barrier+0.5492
Caco-2 permeable-0.746
P-glycoprotein substrateNon-substrate0.6771
P-glycoprotein inhibitor INon-inhibitor0.94
P-glycoprotein inhibitor IINon-inhibitor0.9586
Renal organic cation transporterNon-inhibitor0.9272
CYP450 2C9 substrateNon-substrate0.8517
CYP450 2D6 substrateNon-substrate0.8524
CYP450 3A4 substrateNon-substrate0.7629
CYP450 1A2 substrateNon-inhibitor0.7392
CYP450 2C9 inhibitorNon-inhibitor0.8991
CYP450 2D6 inhibitorNon-inhibitor0.9279
CYP450 2C19 inhibitorNon-inhibitor0.8794
CYP450 3A4 inhibitorNon-inhibitor0.9652
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.905
Ames testNon AMES toxic0.7947
CarcinogenicityNon-carcinogens0.6855
BiodegradationNot ready biodegradable0.7184
Rat acute toxicity2.1543 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9429
hERG inhibition (predictor II)Non-inhibitor0.8275
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 1,2-diols. These are polyols containing an alcohol group at two adjacent positions.
Kingdom
Organic compounds
Super Class
Organic oxygen compounds
Class
Organooxygen compounds
Sub Class
Alcohols and polyols
Direct Parent
1,2-diols
Alternative Parents
Secondary alcohols / Alkylthiols / Hydrocarbon derivatives
Substituents
Secondary alcohol / 1,2-diol / Alkylthiol / Hydrocarbon derivative / Organosulfur compound / Aliphatic acyclic compound
Molecular Framework
Aliphatic acyclic compounds
External Descriptors
1,4-dimercaptobutane-2,3-diol (CHEBI:17456)

Targets

Kind
Protein
Organism
Listeria monocytogenes serovar 1/2a (strain ATCC BAA-679 / EGD-e)
Pharmacological action
Unknown
General Function
Transcription factor activity, sequence-specific dna binding
Specific Function
Positively regulates expression of listeriolysin, of 1-phosphadidylinositol phosphodiesterase (PI-PLC) and other virulence factors.
Gene Name
prfA
Uniprot ID
P22262
Uniprot Name
Listeriolysin regulatory protein
Molecular Weight
27301.24 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]
Kind
Protein
Organism
Mycobacterium tuberculosis
Pharmacological action
Unknown
General Function
Catalyzes the formation of 6,7-dimethyl-8-ribityllumazine by condensation of 5-amino-6-(D-ribitylamino)uracil with 3,4-dihydroxy-2-butanone 4-phosphate. This is the penultimate step in the biosynthesis of riboflavin.
Specific Function
6,7-dimethyl-8-ribityllumazine synthase activity
Gene Name
ribH
Uniprot ID
P9WHE9
Uniprot Name
6,7-dimethyl-8-ribityllumazine synthase
Molecular Weight
16370.415 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]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Zinc ion binding
Specific Function
Not Available
Gene Name
TK1
Uniprot ID
P04183
Uniprot Name
Thymidine kinase, cytosolic
Molecular Weight
25468.455 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 December 01, 2017 14:47