ECMDB: 2-(S-Glutathionyl)acetyl chloride (ECMDB20034) (M2MDB000883)

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 14:23:59 -0600

Update Date

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

Secondary Accession Numbers

ECMDB20034

Identification

Name:

2-(S-Glutathionyl)acetyl chloride

Description

2-(s-glutathionyl)acetyl chloride 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)-1-(carboxymethylamino)-3-(2-chloro-2-Oxoethyl)sulfanyl-1-oxopropan-2-ylamino-5-oxopentanoate
(2S)-2-amino-5-(2R)-1-(carboxymethylamino)-3-(2-chloro-2-oxoethyl)sulfanyl-1-oxopropan-2-ylamino-5-oxopentanoic acid
(2S)-2-amino-5-(2R)-1-(carboxymethylamino)-3-(2-chloro-2-Oxoethyl)sulphanyl-1-oxopropan-2-ylamino-5-oxopentanoate
(2S)-2-amino-5-(2R)-1-(carboxymethylamino)-3-(2-chloro-2-Oxoethyl)sulphanyl-1-oxopropan-2-ylamino-5-oxopentanoic acid
L-g-Glutamyl-S-(2-chloro-2-oxoethyl)-L-cysteinylglycine
L-gamma-Glutamyl-S-(2-chloro-2-oxoethyl)-L-cysteinylglycine
L-γ-Glutamyl-S-(2-chloro-2-oxoethyl)-L-cysteinylglycine

Chemical Formula:

C₁₂H₁₈ClN₃O₇S

Weight:

Average: 383.805
Monoisotopic: 383.055398342

InChI Key:

QUWRSBQWJGCKIV-BQBZGAKWSA-N

InChI:

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

CAS number:

Not Available

IUPAC Name:

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

Traditional IUPAC Name:

C12H18clN3O7S

SMILES:

[H][C@](N)(CCC(O)=N[C@@]([H])(CSCC(Cl)=O)C(O)=NCC(O)=O)C(O)=O

Chemical Taxonomy

Description

belongs to the class of organic compounds known as butenolides. These are dihydrofurans with a carbonyl group at the C2 carbon atom.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Dihydrofurans

Sub Class

Furanones

Direct Parent

Butenolides

Alternative Parents

Substituents

2-furanone
Dicarboxylic acid or derivatives
Enol ester
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Carboxylic acid ester
Lactone
Carboxylic acid derivative
Carboxylic acid
Oxacycle
Chloroalkene
Vinyl chloride
Vinyl halide
Haloalkene
Carbonyl group
Organohalogen compound
Organochloride
Organooxygen compound
Organic oxide
Organic oxygen compound
Hydrocarbon derivative
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

butenolide (CHEBI:81655 )

Physical Properties

State:

Not Available

Charge:

-3

Melting point:

Not Available

Experimental Properties:

Property	Value	Source

Predicted Properties

Property	Value	Source
Water Solubility	0.2 g/L	ALOGPS
logP	-2	ALOGPS
logP	-3.2	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	1.82	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	84.9 m³·mol⁻¹	ChemAxon
Polarizability	35.87 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:

1,1-Dichloroethylene epoxide + Glutathione <> 2-(S-Glutathionyl)acetyl chloride + Hydrochloric acid
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	splash10-052u-8029000000-324c56f17994090f48eb	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positive	splash10-0a4i-4310279000-9c4fc8665e7da781e314	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_3) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_3_2) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_4_7) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS ("2-(S-Glutathionyl)acetyl chloride,2TBDMS,#3" TMS) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0g5i-2159000000-39febf94c6c5a174f114	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00di-9782000000-f948d78248213c9398f6	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00di-9530000000-8fe6fe1aea8b1b1e7c48	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-06si-1319000000-6f9b6df89090f7f53b9d	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-3923000000-90175f07c7cd3d67709e	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0596-5900000000-1475da48240fd5656f33	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001i-0039000000-d760339369cddc0464fa	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-001s-2933000000-56c257ec3a56dc94ada0	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-000i-9510000000-72c153ea79ce99841cda	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-05fr-0192000000-187c7a023576f60034e0	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0ac3-1890000000-9c8da758934152c4b3e1	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-5900000000-7731c5a92bff6f55f910	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	34253
HMDB ID	HMDB0060342
Pubchem Compound ID	0
Kegg ID	C14865
ChemSpider ID	10128368
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 chloride (ECMDB20034) (M2MDB000883)

Structure for #<Compound:0x917c112c>

Enzymes

Reactions