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Record Information

Version

2.0

Creation Date

2012-05-31 14:32:07 -0600

Update Date

2015-06-03 17:19:29 -0600

Secondary Accession Numbers

ECMDB20187

Identification

Name:

S-(2-Chloroacetyl)glutathione

Description

S-(2-chloroacetyl)glutathione is a member of the chemical class 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.

Structure

MOL SDF PDB SMILES InChI

Synonyms:

2-Chloroacetylglutathione
Clch2COSG

Chemical Formula:

C₁₂H₁₈ClN₃O₇S

Weight:

Average: 383.805
Monoisotopic: 383.055398342

InChI Key:

QJDRMMRBPVHMAD-BQBZGAKWSA-N

InChI:

InChI=1S/C12H18ClN3O7S/c13-3-10(20)24-5-7(11(21)15-4-9(18)19)16-8(17)2-1-6(14)12(22)23/h6-7H,1-5,14H2,(H,15,21)(H,16,17)(H,18,19)(H,22,23)/t6-,7-/m0/s1

CAS number:

113668-38-5

IUPAC Name:

(2S)-2-amino-4-{[(1R)-1-[(carboxymethyl)-C-hydroxycarbonimidoyl]-2-[(2-chloroacetyl)sulfanyl]ethyl]-C-hydroxycarbonimidoyl}butanoic acid

Traditional IUPAC Name:

Clch2COSG

SMILES:

[H][C@](N)(CCC(O)=N[C@@]([H])(CSC(=O)CCl)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 or derivatives
N-acyl-alpha-amino acid
Alpha-amino acid amide
Cysteine or derivatives
Alpha-amino acid
N-substituted-alpha-amino acid
Alpha-amino acid or derivatives
L-alpha-amino acid
Halogenated fatty acid
N-acyl-amine
Fatty acyl
Fatty acid
Fatty amide
Dicarboxylic acid or derivatives
Amino acid or derivatives
Secondary carboxylic acid amide
Amino acid
Thiocarboxylic acid ester
Carbothioic s-ester
Carboxamide group
Sulfenyl compound
Carboxylic acid
Thiocarboxylic acid or derivatives
Organohalogen compound
Primary aliphatic amine
Organooxygen compound
Organosulfur compound
Primary amine
Alkyl halide
Alkyl chloride
Carbonyl group
Hydrocarbon derivative
Amine
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Organonitrogen compound
Organochloride
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

peptide (CHEBI:34959 )

Physical Properties

State:

Not Available

Charge:

-3

Melting point:

Not Available

Experimental Properties:

Property	Value	Source

Predicted Properties

Property	Value	Source
Water Solubility	0.26 g/L	ALOGPS
logP	-2.2	ALOGPS
logP	-2.9	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	1.78	ChemAxon
pKa (Strongest Basic)	9.54	ChemAxon
Physiological Charge	-3	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	182.87 Å²	ChemAxon
Rotatable Bond Count	12	ChemAxon
Refractivity	84.38 m³·mol⁻¹	ChemAxon
Polarizability	35.59 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	1	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:

2,2-Dichloroacetaldehyde + Glutathione <> S-(2-Chloroacetyl)glutathione + Hydrochloric acid

SMPDB Pathways:

Not Available

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	splash10-06to-9056000000-e7204464e6c6092cab3f	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positive	splash10-0a4i-6311579000-02bd052633dfabde0920	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0g5i-2169000000-11a0e36c5f0671ed6e93	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00di-9482000000-d1fb0f31b32225ad4b6a	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00di-9530000000-28a6a9bced4114274e03	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-06s9-1149000000-7e513b4ef6b3ce666573	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00di-6359000000-8ba33f3d1794e3f3eb19	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-05fv-9710000000-c13eb3d9c6fcef81715a	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001i-0029000000-395ec87de6a307bcc7eb	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-001r-2892000000-6d5a28aeda438fdf8506	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-000i-9510000000-e8d055a032d1133bd12e	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-1109000000-63195189b791d6697755	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-052s-2692000000-2b57f38867ec57131abe	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-052f-6900000000-2d78da7f72b51d5fe6a1	View in MoNA
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
1D NMR	13C 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	34959
HMDB ID	HMDB0060505
Pubchem Compound ID	163913
Kegg ID	C14864
ChemSpider ID	143757
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

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S-(2-Chloroacetyl)glutathione (M2MDB001033)

Structure for #<Compound:0xad2ee78c>

Enzymes

Reactions