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Record Information

Version

2.0

Creation Date

2012-05-31 14:32:13 -0600

Update Date

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

Secondary Accession Numbers

ECMDB20189

Identification

Name:

S-(Formylmethyl)glutathione

Description

S-(formylmethyl)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)-1-(carboxymethylamino)-1-oxo-3-(2-Oxoethylsulfanyl)propan-2-ylamino-5-oxopentanoate
(2S)-2-amino-5-(2R)-1-(carboxymethylamino)-1-oxo-3-(2-oxoethylsulfanyl)propan-2-ylamino-5-oxopentanoic acid
(2S)-2-amino-5-(2R)-1-(carboxymethylamino)-1-oxo-3-(2-Oxoethylsulphanyl)propan-2-ylamino-5-oxopentanoate
(2S)-2-amino-5-(2R)-1-(carboxymethylamino)-1-oxo-3-(2-Oxoethylsulphanyl)propan-2-ylamino-5-oxopentanoic acid
L-g-Glutamyl-S-(2-oxoethyl)-L-cysteinylglycine
L-gamma-Glutamyl-S-(2-oxoethyl)-L-cysteinylglycine
L-γ-Glutamyl-S-(2-oxoethyl)-L-cysteinylglycine

Chemical Formula:

C₁₂H₁₉N₃O₇S

Weight:

Average: 349.36
Monoisotopic: 349.094370667

InChI Key:

VKLQBAQSSOPXGF-YUMQZZPRSA-N

InChI:

InChI=1S/C12H19N3O7S/c13-7(12(21)22)1-2-9(17)15-8(6-23-4-3-16)11(20)14-5-10(18)19/h3,7-8H,1-2,4-6,13H2,(H,14,20)(H,15,17)(H,18,19)(H,21,22)/t7-,8-/m0/s1

CAS number:

Not Available

IUPAC Name:

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

Traditional IUPAC Name:

S-(formylmethyl)glutathione

SMILES:

[H][C@](N)(CCC(O)=N[C@@]([H])(CSCC=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
Glutamine or derivatives
N-acyl-alpha-amino acid
N-acyl-alpha amino 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
Dicarboxylic acid or derivatives
Fatty amide
Fatty acyl
Fatty acid
N-acyl-amine
Amino acid or derivatives
Carboxamide group
Amino acid
Secondary carboxylic acid amide
Carboxylic acid
Thioether
Sulfenyl compound
Dialkylthioether
Primary amine
Primary aliphatic amine
Hydrocarbon derivative
Organic nitrogen compound
Organic oxygen compound
Carbonyl group
Aldehyde
Amine
Organic oxide
Organopnictogen compound
Organonitrogen compound
Organooxygen compound
Organosulfur compound
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

peptide (CHEBI:34962 )

Physical Properties

State:

Not Available

Charge:

-2

Melting point:

Not Available

Experimental Properties:

Property	Value	Source

Predicted Properties

Property	Value	Source
Water Solubility	0.29 g/L	ALOGPS
logP	-2.6	ALOGPS
logP	-3.9	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	1.91	ChemAxon
pKa (Strongest Basic)	9.54	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	182.87 Å²	ChemAxon
Rotatable Bond Count	12	ChemAxon
Refractivity	80.12 m³·mol⁻¹	ChemAxon
Polarizability	33.85 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-Bromoacetaldehyde + Glutathione <> S-(Formylmethyl)glutathione + Hydrobromic acid
Glutathione + 2,2-Dichloroacetaldehyde > S-(Formylmethyl)glutathione

SMPDB Pathways:

glutathione metabolism II

PW001927

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	splash10-0f6x-9065000000-86d1cba61a3dca3ccc6b	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positive	splash10-00di-5211297000-d93bf9d76a2d2fd8d369	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	splash10-0v59-4189000000-5d5c6497e41130a4bc98	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00di-9150000000-1a124010fc5e38195c38	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00di-9330000000-0d45185377c925296f38	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00ea-3149000000-2ead9ab4ff107e706425	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00di-9242000000-144fc7fc48f1fe4545b2	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9400000000-3beac58433b00fad5b88	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-0149000000-53de86e2588eb657c655	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-015i-2952000000-86890d48f98ecf0342c9	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-000i-9210000000-bd4daba3840bdfffead2	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0592-2189000000-984b1c7e888bfb65e46f	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-05fu-1690000000-ba60c0a835976ac6512d	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-006x-8900000000-1d7b2d35cf7231763801	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	34962
HMDB ID	HMDB0060507
Pubchem Compound ID	11954074
Kegg ID	C14871
ChemSpider ID	10128369
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-(Formylmethyl)glutathione (M2MDB001035)

Structure for #<Compound:0xa7dd10c4>

Enzymes

Reactions