ECMDB: 2-(S-Glutathionyl)acetyl glutathione (ECMDB20035) (M2MDB000884)

Identification Taxonomy Physical Properties Biological Properties Spectra Concentrations Links References Enzymes (2)XML

Proteins (887)

Record Information

Version

2.0

Creation Date

2012-05-31 14:24:02 -0600

Update Date

2015-06-03 17:19:10 -0600

Secondary Accession Numbers

ECMDB20035

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

MOL SDF PDB SMILES InChI

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

Weight:

Average: 654.668
Monoisotopic: 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

Description

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

Substituents

Alpha-oligopeptide
Gamma-glutamyl alpha peptide
S-acylglutathione
Glutamine or derivatives
N-acyl-alpha-amino acid
N-acyl-alpha amino acid or derivatives
Tetracarboxylic acid or derivatives
Alpha-amino acid amide
Cysteine or derivatives
Alpha-amino acid
N-substituted-alpha-amino acid
Alpha-amino acid or derivatives
L-alpha-amino acid
Fatty amide
N-acyl-amine
Fatty acyl
Thiocarboxylic acid ester
Carbothioic s-ester
Secondary carboxylic acid amide
Amino acid or derivatives
Carboxamide group
Amino acid
Thiocarboxylic acid or derivatives
Sulfenyl compound
Dialkylthioether
Thioether
Carboxylic acid
Primary amine
Primary aliphatic amine
Organic nitrogen compound
Hydrocarbon derivative
Organic oxygen compound
Carbonyl group
Organonitrogen compound
Amine
Organic oxide
Organopnictogen compound
Organooxygen compound
Organosulfur compound
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

peptide (CHEBI:34254 )

Physical Properties

State:

Not Available

Charge:

-1

Melting point:

Not Available

Experimental Properties:

Property	Value	Source

Predicted Properties

Property	Value	Source
Water Solubility	0.095 g/L	ALOGPS
logP	-3.2	ALOGPS
logP	-2.2	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	2.99	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	19	ChemAxon
Hydrogen Donor Count	10	ChemAxon
Polar Surface Area	348.67 Å²	ChemAxon
Rotatable Bond Count	23	ChemAxon
Refractivity	148.02 m³·mol⁻¹	ChemAxon
Polarizability	63.02 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	0	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Biological Properties

Cellular Locations:

Cytoplasm

Reactions:

2-(S-Glutathionyl)acetyl chloride + Glutathione <> 2-(S-Glutathionyl)acetyl glutathione + Hydrochloric acid
Glutathione + 2-(S-Glutathionyl)acetyl chloride > 2-(S-Glutathionyl)acetyl glutathione + Hydrochloric acid

SMPDB Pathways:

glutathione metabolism III

PW002018

KEGG Pathways:

Not Available

EcoCyc Pathways:

Not Available

Concentrations

Not Available

Spectra

Spectra:

Spectrum Type	Description	Splash Key
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-1002079000-825c10f889bf9313d8c3	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_4) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_5) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_6) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_7) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_8) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_9) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_10) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_4) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_5) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_6) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_7) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_8) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_9) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_10) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_11) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_12) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_13) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_14) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-3021198000-2833c46038b4903dcaeb	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00di-9001261000-4d633b582f60af37eb94	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00di-9120120000-1ac1bb8421c5210b9029	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4r-0029017000-f8fad5a86ade04ae6a38	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4r-0269002000-0a762d4000e13c7792d1	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0005-3944010000-e5675376f58fb375ab75	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a6r-0001098000-5c1522aa05b12182db09	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-05fr-1102692000-d88e8eabef02fc150551	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0019-9410321000-c1eb47abde448518d437	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-2000039000-d84cba944edf44af3728	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00dl-4940053000-ed324e06bb37c494dfcc	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0007-8902020000-ad1acd025cb0e5e857d7	View in MoNA
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer

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

Links

External Links:

Resource	Link
CHEBI ID	34254
HMDB ID	HMDB0060343
Pubchem Compound ID	0
Kegg ID	C14863
ChemSpider ID	10128367
Wikipedia ID	Not Available
BioCyc ID	Not Available

Enzymes

Protein Details

1. Glutathione S-transferase

General function:: Involved in protein binding
Specific function:: Conjugation of reduced glutathione to a wide number of exogenous and endogenous hydrophobic electrophiles
Gene Name:: gst
Uniprot ID:: P0A9D2
Molecular weight:: 22868

Reactions

RX + glutathione = HX + R-S-glutathione.

Protein Details

2. GSH-dependent disulfide bond oxidoreductase

General function:: Not Available
Specific function:: Not Available
Gene Name:: yfcG
Uniprot ID:: P77526
Molecular weight:: Not Available

2-(S-Glutathionyl)acetyl glutathione (ECMDB20035) (M2MDB000884)

Structure for #<Compound:0xa5decfb0>

Enzymes

Reactions