Identification
NameGlutathione disulfide
Accession NumberDB03310  (EXPT01575, DB09544)
TypeSmall Molecule
GroupsExperimental
Description

A GLUTATHIONE dimer formed by a disulfide bond between the cysteine sulfhydryl side chains during the course of being oxidized.

Structure
Thumb
Synonyms
Glutathione disulphide
GSSG
Oxidized glutathione
Oxiglutatione
External IDs Not Available
Product Ingredients Not Available
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International BrandsNot Available
Brand mixtures
NameLabellerIngredients
Amo Endosol ExtraAmo Canada Company
Bss PlusAlcon, Inc.
NavstelAlcon, Inc.
CategoriesNot Available
UNIIULW86O013H
CAS number27025-41-8
WeightAverage: 612.631
Monoisotopic: 612.151961898
Chemical FormulaC20H32N6O12S2
InChI KeyYPZRWBKMTBYPTK-BJDJZHNGSA-N
InChI
InChI=1S/C20H32N6O12S2/c21-9(19(35)36)1-3-13(27)25-11(17(33)23-5-15(29)30)7-39-40-8-12(18(34)24-6-16(31)32)26-14(28)4-2-10(22)20(37)38/h9-12H,1-8,21-22H2,(H,23,33)(H,24,34)(H,25,27)(H,26,28)(H,29,30)(H,31,32)(H,35,36)(H,37,38)/t9-,10-,11-,12-/m0/s1
IUPAC Name
(2S)-2-amino-4-{[(1R)-2-{[(2R)-2-[(4S)-4-amino-4-carboxybutanamido]-2-[(carboxymethyl)carbamoyl]ethyl]disulfanyl}-1-[(carboxymethyl)carbamoyl]ethyl]carbamoyl}butanoic acid
SMILES
N[C@@H](CCC(=O)N[C@@H](CSSC[C@H](NC(=O)CC[C@H](N)C(O)=O)C(=O)NCC(O)=O)C(=O)NCC(O)=O)C(O)=O
Pharmacology
IndicationNot Available
Structured Indications Not Available
PharmacodynamicsNot Available
Mechanism of action
TargetKindPharmacological actionActionsOrganismUniProt ID
Glutathione S-transferase Mu 2ProteinunknownNot AvailableHumanP28161 details
Glutathione reductase, mitochondrialProteinunknownNot AvailableHumanP00390 details
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organismsNot Available
PathwaysNot Available
Pharmacogenomic Effects/ADRs Not Available
Interactions
Drug Interactions Not Available
Food InteractionsNot Available
References
Synthesis ReferenceNot Available
General ReferencesNot Available
External Links
ATC CodesNot Available
AHFS CodesNot Available
PDB Entries
FDA labelNot Available
MSDSNot Available
Clinical Trials
Clinical Trials Not Available
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage forms
FormRouteStrength
Powder, for solutionIntraocular
Kit; solutionIntraocular
Kit; solutionIntraocular; Irrigation
PricesNot Available
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
US7084130 No2001-11-292021-11-29Us
Properties
StateSolid
Experimental PropertiesNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.406 mg/mLALOGPS
logP-3.6ALOGPS
logP-10ChemAxon
logS-3.2ALOGPS
pKa (Strongest Acidic)1.44ChemAxon
pKa (Strongest Basic)9.61ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count14ChemAxon
Hydrogen Donor Count10ChemAxon
Polar Surface Area317.64 Å2ChemAxon
Rotatable Bond Count21ChemAxon
Refractivity136.65 m3·mol-1ChemAxon
Polarizability58.47 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption-0.5623
Blood Brain Barrier+0.7907
Caco-2 permeable-0.7824
P-glycoprotein substrateSubstrate0.5058
P-glycoprotein inhibitor INon-inhibitor0.9122
P-glycoprotein inhibitor IINon-inhibitor0.9969
Renal organic cation transporterNon-inhibitor0.9418
CYP450 2C9 substrateNon-substrate0.9095
CYP450 2D6 substrateNon-substrate0.8077
CYP450 3A4 substrateNon-substrate0.7521
CYP450 1A2 substrateNon-inhibitor0.9373
CYP450 2C9 inhibitorNon-inhibitor0.8857
CYP450 2D6 inhibitorNon-inhibitor0.9399
CYP450 2C19 inhibitorNon-inhibitor0.8615
CYP450 3A4 inhibitorNon-inhibitor0.8874
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9907
Ames testAMES toxic0.6369
CarcinogenicityNon-carcinogens0.8726
BiodegradationReady biodegradable0.5845
Rat acute toxicity2.0571 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9765
hERG inhibition (predictor II)Non-inhibitor0.9422
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0uki-0290000000-04456f914411a2ecbe4fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0a4i-0039210000-772eee67ad10a2d98fa7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-08fr-1957008000-f8812fd72d475ecd2693View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-03di-0000109000-65d563bcfc551b4a7abdView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-03di-0003309000-7555effd0b74737b9d2fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0a4i-0259201000-2cd328143ce713c285d9View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-05d0-0493000000-93bd088394049a484b9dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-001r-0190000000-88b871b5a3f668f4b3a1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT , positivesplash10-0a59-0019811000-b24651cf6fc55de750b8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-APPI-QQ , positivesplash10-053s-0495300000-69ab8e397b7a546ecd3fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-APPI-QQ , positivesplash10-053r-0007920000-39da34018ceb610daa32View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-03di-0000009000-9cde769e8905f413f7e3View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-03di-0000009000-4e3c9569882ab5507bf2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0292-1000291000-9683d81eec1eab3f9883View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01u0-8214980000-1738ea6e3b4537936eeeView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-057i-9534520000-7ef32e723a98599c32d7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0147096000-e516803ef5124daee1a7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4l-2497151000-ef5ab8f9bbe20555f37cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-006y-9411230000-cc41719d1e717d214643View in MoNA
1D NMR1H NMR SpectrumNot Available
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as gamma-glutamyl peptides. These are oligo- and polypeptides consisting of any C-terminal alpha peptide having a gamma-glutamyl residue attached at the N alpha-position.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentGamma-glutamyl peptides
Alternative ParentsTetracarboxylic acids and derivatives / N-acyl-aliphatic-alpha amino acids / Alpha amino acid amides / L-alpha-amino acids / Amino fatty acids / N-acyl amines / Secondary carboxylic acid amides / Dialkyldisulfides / Sulfenyl compounds / Carboxylic acids
SubstituentsGamma-glutamyl alpha peptide / N-acyl-aliphatic-alpha amino acid / Tetracarboxylic acid or derivatives / N-acyl-alpha amino acid or derivatives / N-acyl-alpha-amino acid / Alpha-amino acid amide / L-alpha-amino acid / Alpha-amino acid or derivatives / N-substituted-alpha-amino acid / Alpha-amino acid
Molecular FrameworkAliphatic acyclic compounds
External Descriptorsorganic disulfide, glutathione derivative (CHEBI:17858 )

Targets

Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
Receptor binding
Specific Function:
Conjugation of reduced glutathione to a wide number of exogenous and endogenous hydrophobic electrophiles.
Gene Name:
GSTM2
Uniprot ID:
P28161
Molecular Weight:
25744.395 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:
Nadp binding
Specific Function:
Maintains high levels of reduced glutathione in the cytosol.
Gene Name:
GSR
Uniprot ID:
P00390
Molecular Weight:
56256.565 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 July 22, 2017 12:04