gamma-Glutamylcysteine
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Identification
- Generic Name
- gamma-Glutamylcysteine
- DrugBank Accession Number
- DB03408
- Background
Not Available
- Type
- Small Molecule
- Groups
- Experimental
- Structure
- Weight
- Average: 250.272
Monoisotopic: 250.062342258 - Chemical Formula
- C8H14N2O5S
- Synonyms
- 5-L-Glutamyl-L-cysteine
- gamma-Glu-Cys
- gamma-L-Glutamyl-L-cysteine
- Glu(-Cys)
- L-gamma-glutamyl-L-cysteine
- L-gamma-Glutamylcysteine
- γGluCys
Pharmacology
- Indication
Not Available
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- Pharmacodynamics
Not Available
- Mechanism of action
Target Actions Organism UGlutathione synthetase Not Available Humans - Absorption
Not Available
- Volume of distribution
Not Available
- Protein binding
Not Available
- Metabolism
- Not Available
- Route of elimination
Not Available
- Half-life
Not Available
- Clearance
Not Available
- Adverse Effects
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- Toxicity
Not Available
- Pathways
Pathway Category Glutamate Metabolism Metabolic Hyperinsulinism-Hyperammonemia Syndrome Disease gamma-Glutamyltranspeptidase Deficiency Disease 2-Hydroxyglutric Aciduria (D and L Form) Disease gamma-Glutamyltransferase Deficiency Disease 4-Hydroxybutyric Aciduria/Succinic Semialdehyde Dehydrogenase Deficiency Disease beta-Mercaptolactate-Cysteine Disulfiduria Disease 5-Oxoprolinase Deficiency Disease Succinic Semialdehyde Dehydrogenase Deficiency Disease Cysteine Metabolism Metabolic Glutathione Metabolism Metabolic 5-Oxoprolinuria Disease Glutathione Synthetase Deficiency Disease Homocarnosinosis Disease Cystinosis, Ocular Nonnephropathic Disease - Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.Not Available
- Food Interactions
- Not Available
Categories
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as n-acyl-alpha amino acids. These 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
- Cysteine and derivatives / L-alpha-amino acids / Fatty acids and conjugates / Dicarboxylic acids and derivatives / Amino acids / Propargyl-type 1,3-dipolar organic compounds / Carboxylic acids / Carboximidic acids / Alkylthiols / Organopnictogen compounds show 4 more
- Substituents
- Aliphatic acyclic compound / Alkylthiol / Alpha-amino acid / Amine / Amino acid / Carbonyl group / Carboximidic acid / Carboximidic acid derivative / Carboxylic acid / Cysteine or derivatives show 16 more
- Molecular Framework
- Aliphatic acyclic compounds
- External Descriptors
- gamma-glutamylcysteine (CHEBI:17515)
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- M984VJS48P
- CAS number
- 636-58-8
- InChI Key
- RITKHVBHSGLULN-WHFBIAKZSA-N
- InChI
- 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
- IUPAC Name
- (2S)-2-amino-4-{[(1R)-1-carboxy-2-sulfanylethyl]carbamoyl}butanoic acid
- SMILES
- N[C@@H](CCC(=O)N[C@@H](CS)C(O)=O)C(O)=O
References
- Synthesis Reference
Hiroaki Nishiuchi, "Method for producing gamma-glutamylcysteine." U.S. Patent US20030124684, issued July 03, 2003.
US20030124684- General References
- Not Available
- External Links
- Human Metabolome Database
- HMDB0001049
- KEGG Compound
- C00669
- PubChem Compound
- 123938
- PubChem Substance
- 46506032
- ChemSpider
- 110467
- ChEBI
- 17515
- ChEMBL
- CHEMBL460831
- ZINC
- ZINC000003870040
- PDBe Ligand
- 3GC
- Wikipedia
- Gamma-Glutamylcysteine
- PDB Entries
- 1m0w / 2bu3 / 3kak / 4x8d / 5oes
Clinical Trials
- Clinical Trials
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Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
- Not Available
- Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 2.62 mg/mL ALOGPS 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 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption - 0.6298 Blood Brain Barrier + 0.8694 Caco-2 permeable - 0.8469 P-glycoprotein substrate Non-substrate 0.7613 P-glycoprotein inhibitor I Non-inhibitor 0.9517 P-glycoprotein inhibitor II Non-inhibitor 0.9886 Renal organic cation transporter Non-inhibitor 0.9576 CYP450 2C9 substrate Non-substrate 0.8399 CYP450 2D6 substrate Non-substrate 0.8295 CYP450 3A4 substrate Non-substrate 0.7275 CYP450 1A2 substrate Non-inhibitor 0.9496 CYP450 2C9 inhibitor Non-inhibitor 0.9364 CYP450 2D6 inhibitor Non-inhibitor 0.9342 CYP450 2C19 inhibitor Non-inhibitor 0.9427 CYP450 3A4 inhibitor Non-inhibitor 0.8919 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9905 Ames test AMES toxic 0.7948 Carcinogenicity Non-carcinogens 0.9386 Biodegradation Ready biodegradable 0.8085 Rat acute toxicity 1.5829 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9946 hERG inhibition (predictor II) Non-inhibitor 0.9654
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 161.4578058 predictedDarkChem Lite v0.1.0 [M-H]- 161.5295058 predictedDarkChem Lite v0.1.0 [M-H]- 161.3289058 predictedDarkChem Lite v0.1.0 [M-H]- 161.3575058 predictedDarkChem Lite v0.1.0 [M-H]- 155.29776 predictedDeepCCS 1.0 (2019) [M+H]+ 160.3565058 predictedDarkChem Lite v0.1.0 [M+H]+ 156.2805441 predictedDarkChem Standard v0.1.0 [M+H]+ 160.2429058 predictedDarkChem Lite v0.1.0 [M+H]+ 160.2652058 predictedDarkChem Lite v0.1.0 [M+H]+ 157.65579 predictedDeepCCS 1.0 (2019) [M+Na]+ 160.4274058 predictedDarkChem Lite v0.1.0 [M+Na]+ 160.4082058 predictedDarkChem Lite v0.1.0 [M+Na]+ 160.2889058 predictedDarkChem Lite v0.1.0 [M+Na]+ 160.3542058 predictedDarkChem Lite v0.1.0 [M+Na]+ 163.74893 predictedDeepCCS 1.0 (2019)
Targets
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1. DetailsGlutathione synthetase
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Catalyzes the production of glutathione from gamma-glutamylcysteine and glycine in an ATP-dependent manner (PubMed:7646467, PubMed:9215686). Glutathione (gamma-glutamylcysteinylglycine, GSH) is the most abundant intracellular thiol in living aerobic cells and is required for numerous processes including the protection of cells against oxidative damage, amino acid transport, the detoxification of foreign compounds, the maintenance of protein sulfhydryl groups in a reduced state and acts as a cofactor for a number of enzymes (PubMed:10369661). Participates in ophthalmate biosynthesis in hepatocytes (By similarity)
- Specific Function
- ATP binding
- Gene Name
- GSS
- Uniprot ID
- P48637
- Uniprot Name
- Glutathione synthetase
- Molecular Weight
- 52384.325 Da
References
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
- Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]
- Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]
Drug created at June 13, 2005 13:24 / Updated at June 12, 2020 16:52