Cannabis Compound Database: Showing Compound Card for gamma-Glutamylcysteine (CDB004878)

Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Protein target Pathways Concentrations Links References enzymes (4) Show 6 proteins XML

Record Information

Version

1.0

Created at

2020-04-17 18:46:08 UTC

Updated at

2020-12-07 19:11:10 UTC

CannabisDB ID

CDB004878

Secondary Accession Numbers

Not Available

Cannabis Compound 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. Outside of the human body, gamma-Glutamylcysteine has been detected, but not quantified in, several different foods, such as hyssops, rapes, black mulberries, red raspberries, and wild carrots. This could make gamma-glutamylcysteine a potential biomarker for the consumption of these foods. gamma-Glutamylcysteine is a potentially toxic compound. A molecular entity formed when L-cysteine amino group binds to the gamma-carbonyl of L-glutamic acid. gamma-Glutamylcysteine is expected to be in Cannabis as all living plants are known to produce and metabolize it.

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

250.27

Monoisotopic Molecular Weight

250.0623

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

Physiological effect

Health effect:

Health condition:

Schizophrenia

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Biological:

Animal

Plant:

Biological location:

Tissue and substructures:

Placenta

Organ and components:

Prostate

Cell and elements:

Cell:

Biofluid and excreta:

Subcellular:

Cytoplasm

Role

Industrial application:

Pharmaceutical industry:

Pharmaceutical

Physical Properties

State

Not Available

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	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
GC-MS	gamma-Glutamylcysteine, non-derivatized, GC-MS Spectrum	splash10-054t-1920100000-5ce9a082971db6d9e2e9	Spectrum
GC-MS	gamma-Glutamylcysteine, non-derivatized, GC-MS Spectrum	splash10-054t-1920100000-5ce9a082971db6d9e2e9	Spectrum
Predicted GC-MS	gamma-Glutamylcysteine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-053u-9630000000-344be03dbe2132b00c88	Spectrum
Predicted GC-MS	gamma-Glutamylcysteine, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-00b9-8494000000-88b1eea1e1badaee084b	Spectrum
Predicted GC-MS	gamma-Glutamylcysteine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-0udi-0090000000-50bd1555ededc1afde80	Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-0udi-0290000000-385ca433f03af7530f47	Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-0ue9-5490000000-95d45a9cd2bb6249d3a2	Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive	splash10-001i-9510000000-5f29ca903abe05256c83	Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-001i-9510000000-5f29ca903abe05256c83	Spectrum
MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-0002-1490000000-bfce673369358b8079e9	Spectrum
MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-0002-0690000000-c49357f0d28683125b6d	Spectrum
MS/MS	LC-MS/MS Spectrum - 30V, Negative	splash10-002b-2490000000-41c54aabf6acd4d3b53e	Spectrum
MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-014j-9050000000-1137fb3c62232376669c	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-05fr-1790000000-2aaa1344429a2297cc6b	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00di-4920000000-4ad42780853d5599c05b	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-05fr-9400000000-b67fd0eaf646aa8f47b3	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000t-1390000000-e723899e4ca71bda7600	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00sj-3960000000-9a2f96ad7d24e7546315	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00e9-9300000000-e14b428bbb5b63d3ae06	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00b9-0910000000-302a05e4e453b27bad64	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004j-3900000000-da869ba294aa1d1e7c49	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-000x-9100000000-4bc7ff3637ea175068f0	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0zmi-0960000000-675f718188f5caad73ab	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-001i-9600000000-13ddc5ab8de093dd11ab	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-001i-9100000000-8b8a5550fa1112649784	Spectrum

NMR

Type	Description	View
1D NMR	1H NMR Spectrum	Spectrum
1D NMR	13C NMR Spectrum	Spectrum
1D NMR	1H NMR Spectrum	Spectrum
1D NMR	13C NMR Spectrum	Spectrum
1D NMR	1H NMR Spectrum	Spectrum
1D NMR	13C NMR Spectrum	Spectrum
1D NMR	1H NMR Spectrum	Spectrum
1D NMR	13C NMR Spectrum	Spectrum
1D NMR	1H NMR Spectrum	Spectrum
1D NMR	13C NMR Spectrum	Spectrum
1D NMR	1H NMR Spectrum	Spectrum
1D NMR	13C NMR Spectrum	Spectrum
1D NMR	1H NMR Spectrum	Spectrum
1D NMR	13C NMR Spectrum	Spectrum
1D NMR	1H NMR Spectrum	Spectrum
1D NMR	13C NMR Spectrum	Spectrum
1D NMR	1H NMR Spectrum	Spectrum
1D NMR	13C NMR Spectrum	Spectrum
1D NMR	1H NMR Spectrum	Spectrum
1D NMR	13C NMR Spectrum	Spectrum
1D NMR	1H NMR Spectrum	Spectrum
2D NMR	[1H,13C] 2D NMR Spectrum	Spectrum

Pathways

Name	SMPDB/Pathwhiz	KEGG
Cysteine Metabolism
Glutamate Metabolism
Glutathione Metabolism
Glutathione Synthetase Deficiency		Not Available
5-Oxoprolinuria		Not Available

Protein Targets

Enzymes

Protein Name	Gene Name	Locus	Uniprot ID	Details
Glutamate--cysteine ligase catalytic subunit	GCLC	6p12	P48506	details
Glutaminyl-peptide cyclotransferase	QPCT	2p22.2	Q16769	details
Glutathione synthetase	GSS	20q11.2	P48637	details
Gamma-glutamylcyclotransferase	GGCT	7p15-p14	O75223	details

Transporters

Not Available

Metal Bindings

Protein Name	Gene Name	Locus	Uniprot ID	Details
Glutaminyl-peptide cyclotransferase	QPCT	2p22.2	Q16769	details

Receptors

Not Available

Transcriptional Factors

Protein Name	Gene Name	Locus	Uniprot ID	Details
Glutamate--cysteine ligase catalytic subunit	GCLC	6p12	P48506	details

Concentrations Data

Not Available

External Links

HMDB ID

HMDB0001049

DrugBank ID

DB03408

Phenol Explorer Compound ID

Not Available

FoodDB 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

General References

Not Available

Enzymes

Enzyme Details

1. Glutamate--cysteine ligase catalytic subunit

General function:: Involved in glutamate-cysteine ligase activity
Specific function:: Not Available
Gene Name:: GCLC
Uniprot ID:: P48506
Molecular weight:: 68629.42

Enzyme Details

2. Glutaminyl-peptide cyclotransferase

General function:: Involved in peptidase activity
Specific function:: Responsible for the biosynthesis of pyroglutamyl peptides. Has a bias against acidic and tryptophan residues adjacent to the N-terminal glutaminyl residue and a lack of importance of chain length after the second residue. Also catalyzes N-terminal pyroglutamate formation. In vitro, catalyzes pyroglutamate formation of N-terminally truncated form of APP amyloid-beta peptides [Glu-3]-beta-amyloid. May be involved in the N-terminal pyroglutamate formation of several amyloid-related plaque-forming peptides.
Gene Name:: QPCT
Uniprot ID:: Q16769
Molecular weight:: 40876.14

Enzyme Details

3. Glutathione synthetase

General function:: Involved in catalytic activity
Specific function:: Not Available
Gene Name:: GSS
Uniprot ID:: P48637
Molecular weight:: 52384.325

Enzyme Details

4. 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:: O75223
Molecular weight:: 19091.635

Showing Compound Card for gamma-Glutamylcysteine (CDB004878)

Structure for CDB004878 (gamma-Glutamylcysteine)

Enzymes