Glutathione Sulfonic Acid

Identification

Name
Glutathione Sulfonic Acid
Accession Number
DB03003  (EXPT01662)
Type
Small Molecule
Groups
Experimental
Description
Not Available
Structure
Thumb
Synonyms
Not Available
Categories
Not Available
UNII
Not Available
CAS number
Not Available
Weight
Average: 355.322
Monoisotopic: 355.068549847
Chemical Formula
C10H17N3O9S
InChI Key
QGWRMTHFAZVWAM-WDSKDSINSA-N
InChI
InChI=1S/C10H17N3O9S/c11-5(10(18)19)1-2-7(14)13-6(4-23(20,21)22)9(17)12-3-8(15)16/h5-6H,1-4,11H2,(H,12,17)(H,13,14)(H,15,16)(H,18,19)(H,20,21,22)/t5-,6-/m0/s1
IUPAC Name
(2S)-2-amino-4-{[(1R)-1-[(carboxymethyl)-C-hydroxycarbonimidoyl]-2-sulfoethyl]-C-hydroxycarbonimidoyl}butanoic acid
SMILES
[H][[email protected]](N)(CCC(O)=N[[email protected]@]([H])(CS(O)(=O)=O)C(O)=NCC(O)=O)C(O)=O

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UGlutathione S-transferase Mu 4Not AvailableHuman
UGlutathione S-transferase A1Not AvailableHuman
UGlutathione S-transferase PNot AvailableHuman
UGlutathione S-transferase GstANot AvailableEscherichia coli (strain K12)
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
PubChem Compound
444104
PubChem Substance
46504962
ChemSpider
392112
HET
GTS
PDB Entries
1a0f / 1ev4 / 1ev9 / 1glp / 1m99 / 1n2a / 1r5a / 1v2a / 2gsr / 3erg
show 3 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
Not Available
Predicted Properties
PropertyValueSource
Water Solubility2.16 mg/mLALOGPS
logP-1.8ALOGPS
logP-3.8ChemAxon
logS-2.2ALOGPS
pKa (Strongest Acidic)-1.7ChemAxon
pKa (Strongest Basic)9.54ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count12ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area220.17 Å2ChemAxon
Rotatable Bond Count10ChemAxon
Refractivity72.37 m3·mol-1ChemAxon
Polarizability31.56 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption-0.9268
Blood Brain Barrier+0.6322
Caco-2 permeable-0.6817
P-glycoprotein substrateNon-substrate0.7439
P-glycoprotein inhibitor INon-inhibitor0.8766
P-glycoprotein inhibitor IINon-inhibitor0.9925
Renal organic cation transporterNon-inhibitor0.9574
CYP450 2C9 substrateNon-substrate0.8643
CYP450 2D6 substrateNon-substrate0.8061
CYP450 3A4 substrateNon-substrate0.6723
CYP450 1A2 substrateNon-inhibitor0.8804
CYP450 2C9 inhibitorNon-inhibitor0.8728
CYP450 2D6 inhibitorNon-inhibitor0.9175
CYP450 2C19 inhibitorNon-inhibitor0.8597
CYP450 3A4 inhibitorNon-inhibitor0.9816
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9927
Ames testNon AMES toxic0.5922
CarcinogenicityNon-carcinogens0.6281
BiodegradationReady biodegradable0.7155
Rat acute toxicity2.1180 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9305
hERG inhibition (predictor II)Non-inhibitor0.8825
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
Gamma-glutamyl peptides / Glutamine and derivatives / N-acyl-alpha amino acids / Alpha amino acid amides / L-alpha-amino acids / N-acyl amines / Dicarboxylic acids and derivatives / Fatty acids and conjugates / Sulfonyls / Organosulfonic acids
show 9 more
Substituents
Alpha-oligopeptide / Gamma-glutamyl alpha peptide / Glutamine or derivatives / N-acyl-alpha-amino acid / N-acyl-alpha amino acid or derivatives / Alpha-amino acid amide / Alpha-amino acid / N-substituted-alpha-amino acid / Alpha-amino acid or derivatives / L-alpha-amino acid
show 28 more
Molecular Framework
Aliphatic acyclic compounds
External Descriptors
Not Available

Targets

Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Protein homodimerization activity
Specific Function
Conjugation of reduced glutathione to a wide number of exogenous and endogenous hydrophobic electrophiles. Active on 1-chloro-2,4-dinitrobenzene.
Gene Name
GSTM4
Uniprot ID
Q03013
Uniprot Name
Glutathione S-transferase Mu 4
Molecular Weight
25561.095 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]
  3. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Glutathione transferase activity
Specific Function
Conjugation of reduced glutathione to a wide number of exogenous and endogenous hydrophobic electrophiles.
Gene Name
GSTA1
Uniprot ID
P08263
Uniprot Name
Glutathione S-transferase A1
Molecular Weight
25630.785 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]
  3. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
S-nitrosoglutathione binding
Specific Function
Conjugation of reduced glutathione to a wide number of exogenous and endogenous hydrophobic electrophiles. Regulates negatively CDK5 activity via p25/p35 translocation to prevent neurodegeneration.
Gene Name
GSTP1
Uniprot ID
P09211
Uniprot Name
Glutathione S-transferase P
Molecular Weight
23355.625 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]
  3. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235]
Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
Unknown
General Function
Glutathione transferase activity
Specific Function
Catalyzes the conjugation of reduced glutathione (GSH) to a wide number of exogenous and endogenous hydrophobic electrophiles. Shows activity toward 1-chloro-2,4-dinitrobenzene (CDNB) and ethacryni...
Gene Name
gstA
Uniprot ID
P0A9D2
Uniprot Name
Glutathione S-transferase GstA
Molecular Weight
22868.14 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 15:06