Bovine Metabolome Database: Showing metabocard for Gamma-Glutamylcysteine (BMDB0001049)

Identification Taxonomy Physical properties Pathways Spectra Concentrations Links References enzymes (4) Show 4 proteins XML

Record Information

Version

1.0

Creation Date

2016-09-30 22:40:22 UTC

Update Date

2020-05-21 16:28:25 UTC

BMDB ID

BMDB0001049

Secondary Accession Numbers

BMDB01049

Metabolite Identification

Common Name

Gamma-Glutamylcysteine

Description

gamma-Glutamylcysteine, also known as L-γ-glutamylcysteine or gamma-glu-cys, belongs to the class of organic compounds known as n-acyl-alpha amino acids. N-acyl-alpha amino acids are compounds containing an alpha amino acid which bears an acyl group at its terminal nitrogen atom. gamma-Glutamylcysteine is a very strong basic compound (based on its pKa). gamma-Glutamylcysteine exists in all living species, ranging from bacteria to humans. gamma-Glutamylcysteine is a potentially toxic compound.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
5-L-Glutamyl-L-cysteine	ChEBI
gamma-Glu-cys	ChEBI
gamma-L-Glutamyl-L-cysteine	ChEBI
L-gamma-Glutamylcysteine	ChEBI
g-Glu-cys	Generator
Γ-glu-cys	Generator
g-L-Glutamyl-L-cysteine	Generator
Γ-L-glutamyl-L-cysteine	Generator
L-g-Glutamylcysteine	Generator
L-Γ-glutamylcysteine	Generator
g-Glutamylcysteine	Generator
Γ-glutamylcysteine	Generator
Γ-L-glu-L-cys	HMDB
L-Γ-glutamyl-L-cysteine	HMDB
N-Γ-glutamylcysteine	HMDB
N-L-Γ-glutamylcysteine	HMDB
N-L-Γ-glutamyl-L-cysteine	HMDB
gamma-L-Glu-L-cys	HMDB
L-gamma-Glutamyl-L-cysteine	HMDB
N-gamma-Glutamylcysteine	HMDB
N-L-gamma-Glutamylcysteine	HMDB
N-L-gamma-Glutamyl-L-cysteine	HMDB
5-L-Glutamylcysteine	HMDB
H-gamma-Glu-cys-OH	HMDB
L-g-Glutamyl-L-cysteine	HMDB
N-Γ-L-glutamyl-L-cysteine	HMDB
gamma-Glutamylcysteine	HMDB

Chemical Formula

C₈H₁₄N₂O₅S

Average Molecular Weight

250.272

Monoisotopic Molecular Weight

250.062342258

IUPAC Name

(2S)-2-amino-4-{[(1R)-1-carboxy-2-sulfanylethyl]carbamoyl}butanoic acid

Traditional Name

gamma-glutamylcysteine

CAS Registry Number

636-58-8

SMILES

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

InChI Identifier

InChI=1S/C8H14N2O5S/c9-4(7(12)13)1-2-6(11)10-5(3-16)8(14)15/h4-5,16H,1-3,9H2,(H,10,11)(H,12,13)(H,14,15)/t4-,5-/m0/s1

InChI Key

RITKHVBHSGLULN-WHFBIAKZSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as n-acyl-alpha amino acids. N-acyl-alpha amino acids are compounds containing an alpha amino acid which bears an acyl group at its terminal nitrogen atom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

N-acyl-alpha amino acids

Alternative Parents

Substituents

N-acyl-alpha-amino acid
Cysteine or derivatives
Alpha-amino acid
L-alpha-amino acid
Fatty acid
Dicarboxylic acid or derivatives
Amino acid
Alkylthiol
Carboximidic acid
Carboximidic acid derivative
Carboxylic acid
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Organic nitrogen compound
Organooxygen compound
Organonitrogen compound
Organosulfur compound
Primary aliphatic amine
Primary amine
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Carbonyl group
Amine
Organic oxygen compound
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

gamma-glutamylcysteine (CHEBI:17515 )

Ontology

Status

Detected but not Quantified

Origin

Endogenous

Biofunction

Not Available

Application

Not Available

Cellular locations

Cytoplasm

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	-2.5	ALOGPS
logP	-3.8	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	1.91	ChemAxon
pKa (Strongest Basic)	9.24	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	129.72 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	56.31 m³·mol⁻¹	ChemAxon
Polarizability	23.36 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-054t-1920100000-5ce9a082971db6d9e2e9	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-054t-1920100000-5ce9a082971db6d9e2e9	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-053u-9630000000-344be03dbe2132b00c88	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-00b9-8494000000-88b1eea1e1badaee084b	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	View in JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-0udi-0090000000-50bd1555ededc1afde80	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-0udi-0290000000-385ca433f03af7530f47	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-0ue9-5490000000-95d45a9cd2bb6249d3a2	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive	splash10-001i-9510000000-5f29ca903abe05256c83	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-001i-9510000000-5f29ca903abe05256c83	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-0002-1490000000-bfce673369358b8079e9	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-0002-0690000000-c49357f0d28683125b6d	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 30V, Negative	splash10-002b-2490000000-41c54aabf6acd4d3b53e	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-014j-9050000000-1137fb3c62232376669c	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-05fr-1790000000-2aaa1344429a2297cc6b	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00di-4920000000-4ad42780853d5599c05b	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-05fr-9400000000-b67fd0eaf646aa8f47b3	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000t-1390000000-e723899e4ca71bda7600	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00sj-3960000000-9a2f96ad7d24e7546315	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00e9-9300000000-e14b428bbb5b63d3ae06	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00b9-0910000000-302a05e4e453b27bad64	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004j-3900000000-da869ba294aa1d1e7c49	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-000x-9100000000-4bc7ff3637ea175068f0	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0zmi-0960000000-675f718188f5caad73ab	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-001i-9600000000-13ddc5ab8de093dd11ab	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-001i-9100000000-8b8a5550fa1112649784	View in MoNA
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Not Available	View in JSpectraViewer

Biological Properties

Cellular Locations

Cytoplasm

Biospecimen Locations

Fibroblasts
Liver
Neuron
Placenta
Prostate Tissue

Pathways

Name	SMPDB/Pathwhiz	KEGG
Glutathione Metabolism		Not Available
Glutamate Metabolism		Not Available
Cysteine Metabolism		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Fibroblasts	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Liver	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 31867104	details
Neuron	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Placenta	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Prostate Tissue	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details

Abnormal Concentrations

Not Available

External Links

HMDB ID

HMDB0001049

DrugBank ID

DB03408

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

L-GAMMA-GLUTAMYLCYSTEINE

BiGG ID

35655

Wikipedia Link

Gamma-Glutamylcysteine

METLIN ID

5966

PubChem Compound

123938

PDB ID

Not Available

ChEBI ID

17515

References

Synthesis Reference

Bridge, Wallace John; Zarka, Martin Hani. Enzymic production of g-glutamylcysteine. PCT Int. Appl. (2006), 76pp.

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Enzymes

Enzyme Details

1. Glutathione synthetase

General function:: Involved in ATP binding
Specific function:: Not Available
Gene Name:: GSS
Uniprot ID:: Q5EAC2
Molecular weight:: 52066.0

Reactions

Adenosine triphosphate + Gamma-Glutamylcysteine + Glycine → ADP + Hydrogen phosphate + Glutathione	details
Gamma-Glutamylcysteine + Adenosine triphosphate + Glycine → Glutathione + ADP + Hydrogen phosphate	details

Enzyme Details

2. Glutamate-cysteine ligase catalytic subunit

General function:: Involved in ADP binding
Specific function:: Not Available
Gene Name:: GCLC
Uniprot ID:: Q32S38
Molecular weight:: 69023.0

Reactions

Adenosine triphosphate + L-Glutamic acid + L-Cysteine → ADP + Hydrogen phosphate + Gamma-Glutamylcysteine	details
L-Glutamic acid + Adenosine triphosphate + L-Cysteine → Gamma-Glutamylcysteine + Adenosine diphosphate ribose + Hydrogen phosphate	details

Enzyme Details

3. Gamma-glutamylcyclotransferase

General function:: Involved in acyltransferase activity
Specific function:: Catalyzes the formation of 5-oxoproline from gamma-glutamyl dipeptides and may play a significant role in glutathione homeostasis. Induces release of cytochrome c from mitochondria with resultant induction of apoptosis.
Gene Name:: GGCT
Uniprot ID:: Q32LE4
Molecular weight:: 21177.0

Reactions

Gamma-Glutamylcysteine → L-Cysteine + Pyroglutamic acid	details

Enzyme Details

4. Glutamate--cysteine ligase regulatory subunit

General function:: Not Available
Specific function:: Not Available
Gene Name:: GCLM
Uniprot ID:: Q2T9Y6
Molecular weight:: 30533.0

Reactions

Adenosine triphosphate + L-Glutamic acid + L-Cysteine → ADP + Hydrogen phosphate + Gamma-Glutamylcysteine	details
L-Glutamic acid + Adenosine triphosphate + L-Cysteine → Gamma-Glutamylcysteine + Adenosine diphosphate ribose + Hydrogen phosphate	details

Showing metabocard for Gamma-Glutamylcysteine (BMDB0001049)

Structure for BMDB0001049 (Gamma-Glutamylcysteine)

Enzymes

Reactions

Reactions

Reactions

Reactions