L-cysteinylglycine (YMDB00690)

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Identification

YMDB ID

YMDB00690

Name

L-cysteinylglycine

Species

Saccharomyces cerevisiae

Strain

Baker's yeast

Description

Cysteinylglycine, also known as CG or cys-gly, belongs to the class of organic compounds known as dipeptides. These are organic compounds containing a sequence of exactly two alpha-amino acids joined by a peptide bond. Cysteinylglycine is a very strong basic compound (based on its pKa). Cysteinylglycine exists in all living species, ranging from bacteria to humans.

Structure

MOL SDF PDB SMILES InChI

Synonyms

5-l-glutamyl-l-cysteinylglycine
Agifutol S
Bakezyme RX
Copren
Cys-Gly
Cysteinylglycine
Deltathione
gamma-Glutamylcysteinylglycine
gamma-l-glutamyl-l-cysteinyl-glycine
gamma-L-Glutamyl-L-cysteinylglycine
Glutathion
Glutathione
Glutathione (reduced type)
Glutathione (reduced)
Glutathione red
Glutathione reduced
Glutathione-SH
Glutatiol
Glutatione
Gluthathione
Glutide
Glutinal
GSH
Isethion
L-Cysteinylglycine
L-g-glutamyl-L-cysteinyl-glycine
L-gamma-glutamyl-L-cysteinyl-glycine
L-gamma-glutamyl-L-cysteinylglycine
L-glutamyl-L-cysteinylglycine
L-Glutathione
L-Glutathione reduce
Ledac
n-(n-gamma-l-glutamyl-l-cysteinyl)glycine
N-L-cysteinylglycine
Neuthion
red. glutathione
Reduced glutathione
Tathion
Tathione
Triptide
CG
N-Cysteinyl glycine
N-Cysteinyl-glycine
N-L-Cysteinyl-glycine
Cysteinyl-glycine
C-g Dipeptide
CG Dipeptide
Cysteine glycine dipeptide
Cysteine-glycine dipeptide
L-Cys-gly
N-Cysteinylglycine

CAS number

70-18-8

Weight

Average: 178.21
Monoisotopic: 178.041212886

InChI Key

ZUKPVRWZDMRIEO-VKHMYHEASA-N

InChI

InChI=1S/C5H10N2O3S/c6-3(2-11)5(10)7-1-4(8)9/h3,11H,1-2,6H2,(H,7,10)(H,8,9)/t3-/m0/s1

IUPAC Name

2-[(2R)-2-amino-3-sulfanylpropanamido]acetic acid

Traditional IUPAC Name

Cys-Gly

Chemical Formula

C₅H₁₀N₂O₃S

SMILES

N[C@@H](CS)C(=O)NCC(O)=O

Chemical Taxonomy

Description

belongs to the class of organic compounds known as dipeptides. These are organic compounds containing a sequence of exactly two alpha-amino acids joined by a peptide bond.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Dipeptides

Alternative Parents

Substituents

Alpha-dipeptide
N-acyl-alpha-amino acid
N-acyl-alpha amino acid or derivatives
Alpha-amino acid amide
Cysteine or derivatives
Alpha-amino acid or derivatives
Amino acid or derivatives
Amino acid
Carboxamide group
Secondary carboxylic acid amide
Alkylthiol
Carboxylic acid
Monocarboxylic acid or derivatives
Organic nitrogen compound
Organonitrogen compound
Organooxygen compound
Organosulfur compound
Primary aliphatic amine
Primary amine
Hydrocarbon derivative
Carbonyl group
Organic oxide
Amine
Organopnictogen compound
Organic oxygen compound
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

dipeptide (CHEBI:4047 )

Physical Properties

State

Solid

Charge

Melting point

195 °C

Experimental Properties

Property	Value	Reference
Water Solubility	Not Available	PhysProp
LogP	Not Available	PhysProp

Predicted Properties

Property	Value	Source
Water Solubility	6.25 g/L	ALOGPS
logP	-2.6	ALOGPS
logP	-3.9	ChemAxon
logS	-1.5	ALOGPS
pKa (Strongest Acidic)	3.6	ChemAxon
pKa (Strongest Basic)	8.08	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	92.42 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	41.03 m³·mol⁻¹	ChemAxon
Polarizability	16.97 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

Organoleptic Properties

Not Available

SMPDB Pathways

Glutathione metabolism	PW002395
Pyruvate metabolism	PW002447

KEGG Pathways

Cysteine and methionine metabolism	ec00270
Glutathione metabolism	ec00480
Pyruvate metabolism	ec00620

SMPDB Reactions

Glutathione + L-Cysteine → L-cysteinylglycine + Gamma-Glutamylcysteine

L-cysteinylglycine + water → Glycine + L-Cysteine

KEGG Reactions

Glutathione + L-Alanine → L-cysteinylglycine + L-gamma-Glutamyl-L-alanine

Concentrations

Intracellular Concentrations

Not Available

Extracellular Concentrations

Not Available

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - GC-MS (3 TMS)	splash10-00di-2980000000-043097e8f1f3f47ff51f	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00di-9440000000-ff8b27f3afc92193d83a	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-00di-2980000000-043097e8f1f3f47ff51f	JSpectraViewer \| MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-004i-9200000000-bae23059b39c80a574a5	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-006t-8920000000-1b3a6e358d6996916b0e	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_4) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_4) - 70eV, Positive	Not Available	JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-004i-9700000000-6fba6043a24b724b037e	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-9000000000-50e069074067c9f120bd	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-004i-9100000000-ab3327c5b13829ea6d35	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-004i-9700000000-9021340a904a56f317cc	JSpectraViewer \| MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004i-5900000000-b9a1082799c427caf10b	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-004i-9200000000-2b99992e97c6ecb4567b	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a6u-9000000000-a8b591f7522fe16637fb	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-2900000000-0173b5cf52bb61095c3a	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00gl-7900000000-f8dc26c3e8b8ec327fc4	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0kh9-9100000000-410b0cc1b5e3f850b505	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0096-5900000000-55967cd7162376aa6fa2	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00di-9200000000-5aab410f2c44502defce	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00di-9000000000-e0ae26ebba3eeba905da	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-056r-9400000000-1878c834f39272d5af42	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-056r-9100000000-0899c0bce2addb667ccb	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-9000000000-05f619b00f6286d67d21	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer

References

References:

Scheer, M., Grote, A., Chang, A., Schomburg, I., Munaretto, C., Rother, M., Sohngen, C., Stelzer, M., Thiele, J., Schomburg, D. (2011). "BRENDA, the enzyme information system in 2011." Nucleic Acids Res 39:D670-D676.21062828
Herrgard, M. J., Swainston, N., Dobson, P., Dunn, W. B., Arga, K. Y., Arvas, M., Bluthgen, N., Borger, S., Costenoble, R., Heinemann, M., Hucka, M., Le Novere, N., Li, P., Liebermeister, W., Mo, M. L., Oliveira, A. P., Petranovic, D., Pettifer, S., Simeonidis, E., Smallbone, K., Spasic, I., Weichart, D., Brent, R., Broomhead, D. S., Westerhoff, H. V., Kirdar, B., Penttila, M., Klipp, E., Palsson, B. O., Sauer, U., Oliver, S. G., Mendes, P., Nielsen, J., Kell, D. B. (2008). "A consensus yeast metabolic network reconstruction obtained from a community approach to systems biology." Nat Biotechnol 26:1155-1160.18846089

Synthesis Reference:

Not Available

External Links:

Resource	Link
CHEBI ID	4047
HMDB ID	HMDB00125
Pubchem Compound ID	65270
Kegg ID	C00051
ChemSpider ID	388596
FOODB ID	FDB021891
Wikipedia	Glutathione
BioCyc ID	OXIDIZED-GLUTATHIONE

Enzymes

Protein Details

1. Gamma-glutamyltransferase

General function:: Involved in gamma-glutamyltransferase activity
Specific function:: Plays a role in the turnover of the vacuolar glutathione and in the supply of growth requirements during nitrogen starvation
Gene Name:: ECM38
Uniprot ID:: Q05902
Molecular weight:: 73179.79688

Reactions

(5-L-glutamyl)-peptide + an amino acid → peptide + 5-L-glutamyl amino acid.

Structure for #<Compound:0xa2f63b30>

Enzymes

Reactions