2-(S-Glutathionyl)acetyl glutathione (PAMDB000884)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 12:54:54 PM
Metabolite IDPAMDB000884
Identification
Name: 2-(S-Glutathionyl)acetyl glutathione
Description:2-(s-glutathionyl)acetyl glutathione belongs to the class of Peptides. These are compounds containing an amide derived from two or more amino carboxylic acid molecules (the same or different) by formation of a covalent bond from the carbonyl carbon of one to the nitrogen atom of another. (inferred from compound structure)
Structure
Thumb
🔍MOLSDFPDBSMILESInChIView Structure
Synonyms:
  • (2S)-2-amino-5-(2R)-3-2-(2R)-2-(4S)-4-amino-4-carboxybutanoylamino-3-(carboxymethylamino)-3-Oxopropylsulfanyl-2-oxoethylsulfanyl-1-(carboxymethylamino)-1-oxopropan-2-ylamino-5-oxopentanoate
  • (2S)-2-amino-5-(2R)-3-2-(2R)-2-(4S)-4-amino-4-carboxybutanoylamino-3-(carboxymethylamino)-3-oxopropylsulfanyl-2-oxoethylsulfanyl-1-(carboxymethylamino)-1-oxopropan-2-ylamino-5-oxopentanoic acid
  • (2S)-2-amino-5-(2R)-3-2-(2R)-2-(4S)-4-amino-4-carboxybutanoylamino-3-(carboxymethylamino)-3-Oxopropylsulphanyl-2-oxoethylsulphanyl-1-(carboxymethylamino)-1-oxopropan-2-ylamino-5-oxopentanoate
  • (2S)-2-amino-5-(2R)-3-2-(2R)-2-(4S)-4-amino-4-carboxybutanoylamino-3-(carboxymethylamino)-3-Oxopropylsulphanyl-2-oxoethylsulphanyl-1-(carboxymethylamino)-1-oxopropan-2-ylamino-5-oxopentanoic acid
  • (2S,7R,14R,19S)-2,19-diamino-7,14-Bis(carboxymethyl)carbamoyl-5,10,16-trioxo-9,12-dithia-6,15-diazaicosane-1,20-dioate (non-preferred name)
  • (2S,7R,14R,19S)-2,19-Diamino-7,14-bis(carboxymethyl)carbamoyl-5,10,16-trioxo-9,12-dithia-6,15-diazaicosane-1,20-dioic acid (non-preferred name)
Chemical Formula: C22H34N6O13S2
Average Molecular Weight: 654.668
Monoisotopic Molecular Weight: 654.162526584
InChI Key: QEJUVDVAWJBQIG-CYDGBPFRSA-N
InChI:InChI=1S/C22H34N6O13S2/c23-10(21(38)39)1-3-14(29)27-12(19(36)25-5-16(31)32)7-42-9-18(35)43-8-13(20(37)26-6-17(33)34)28-15(30)4-2-11(24)22(40)41/h10-13H,1-9,23-24H2,(H,25,36)(H,26,37)(H,27,29)(H,28,30)(H,31,32)(H,33,34)(H,38,39)(H,40,41)/t10-,11-,12-,13-/m0/s1
CAS number: Not Available
IUPAC Name:(2S)-2-amino-4-{[(1R)-2-[(2-{[(2R)-2-{[(4S)-4-amino-4-carboxy-1-hydroxybutylidene]amino}-2-[(carboxymethyl)-C-hydroxycarbonimidoyl]ethyl]sulfanyl}acetyl)sulfanyl]-1-[(carboxymethyl)-C-hydroxycarbonimidoyl]ethyl]-C-hydroxycarbonimidoyl}butanoic acid
Traditional IUPAC Name: (2S)-2-amino-4-{[(1R)-2-[(2-{[(2R)-2-{[(4S)-4-amino-4-carboxy-1-hydroxybutylidene]amino}-2-(carboxymethyl-C-hydroxycarbonimidoyl)ethyl]sulfanyl}acetyl)sulfanyl]-1-(carboxymethyl-C-hydroxycarbonimidoyl)ethyl]-C-hydroxycarbonimidoyl}butanoic acid
SMILES:[H][C@](N)(CCC(O)=N[C@@]([H])(CSCC(=O)SC[C@]([H])(N=C(O)CC[C@]([H])(N)C(O)=O)C(O)=NCC(O)=O)C(O)=NCC(O)=O)C(O)=O
Chemical Taxonomy
Taxonomy DescriptionThis compound belongs to the class of organic compounds known as peptides. These are compounds containing an amide derived from two or more amino carboxylic acid molecules (the same or different) by formation of a covalent bond from the carbonyl carbon of one to the nitrogen atom of another.
Kingdom Organic compounds
Super ClassOrganic acids and derivatives
Class Carboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct Parent Peptides
Alternative Parents
Substituents
  • Alpha peptide
  • N-acyl-aliphatic-alpha amino acid
  • Tetracarboxylic acid or derivatives
  • N-acyl-alpha amino acid or derivatives
  • N-acyl-alpha-amino acid
  • L-alpha-amino acid
  • D-alpha-amino acid
  • Alpha-amino acid or derivatives
  • Alpha-amino acid
  • Amino fatty acid
  • Fatty acyl
  • Thiocarboxylic acid ester
  • Dialkylthioether
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Sulfenyl compound
  • Thioether
  • Thiocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboximidic acid derivative
  • Carboximidic acid
  • Hydrocarbon derivative
  • Primary amine
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Carbonyl group
  • Amine
  • Aliphatic acyclic compound
Molecular Framework Aliphatic acyclic compounds
External Descriptors Not Available
Physical Properties
State: Not Available
Charge:-1
Melting point: Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility0.0954 mg/mLALOGPS
logP-3.2ALOGPS
logP-2.2ChemAxon
logS-3.8ALOGPS
pKa (Strongest Acidic)2.99ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count19ChemAxon
Hydrogen Donor Count10ChemAxon
Polar Surface Area348.67 Å2ChemAxon
Rotatable Bond Count23ChemAxon
Refractivity148.02 m3·mol-1ChemAxon
Polarizability63.02 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Cytoplasm
Reactions:
2-(S-Glutathionyl)acetyl chloride + Glutathione <> 2-(S-Glutathionyl)acetyl glutathione + Hydrochloric acid
Pathways: Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-3021198000-2833c46038b4903dcaebView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-9001261000-4d633b582f60af37eb94View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00di-9120120000-1ac1bb8421c5210b9029View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4r-0029017000-f8fad5a86ade04ae6a38View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4r-0269002000-0a762d4000e13c7792d1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0005-3944010000-e5675376f58fb375ab75View in MoNA
References
References:
  • Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
Synthesis Reference: Not Available
Material Safety Data Sheet (MSDS) Not Available
External Links:
ResourceLink
CHEBI IDNot Available
HMDB IDHMDB60343
Pubchem Compound ID0
Kegg IDC14863
ChemSpider ID10128367
Wikipedia IDNot Available
BioCyc IDNot Available

Enzymes

Protein Details
• GSH-dependent disulfide bond oxidoreductase
General function:
Not Available
Specific function:
Not Available
Gene Name:
yfcG
Locus Tag:
PA1033
Molecular weight:
24.5 kDa