gamma-Glutamylcysteine

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
TargetActionsOrganism
UGlutathione synthetaseNot AvailableHumans
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
PathwayCategory
Glutamate MetabolismMetabolic
Hyperinsulinism-Hyperammonemia SyndromeDisease
gamma-Glutamyltranspeptidase DeficiencyDisease
2-Hydroxyglutric Aciduria (D and L Form)Disease
gamma-Glutamyltransferase DeficiencyDisease
4-Hydroxybutyric Aciduria/Succinic Semialdehyde Dehydrogenase DeficiencyDisease
beta-Mercaptolactate-Cysteine DisulfiduriaDisease
5-Oxoprolinase DeficiencyDisease
Succinic Semialdehyde Dehydrogenase DeficiencyDisease
Cysteine MetabolismMetabolic
Glutathione MetabolismMetabolic
5-OxoprolinuriaDisease
Glutathione Synthetase DeficiencyDisease
HomocarnosinosisDisease
Cystinosis, Ocular NonnephropathicDisease
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
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
PhaseStatusPurposeConditionsCount

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
PropertyValueSource
Water Solubility2.62 mg/mLALOGPS
logP-2.5ALOGPS
logP-3.8Chemaxon
logS-2ALOGPS
pKa (Strongest Acidic)1.91Chemaxon
pKa (Strongest Basic)9.24Chemaxon
Physiological Charge-1Chemaxon
Hydrogen Acceptor Count6Chemaxon
Hydrogen Donor Count5Chemaxon
Polar Surface Area129.72 Å2Chemaxon
Rotatable Bond Count7Chemaxon
Refractivity56.31 m3·mol-1Chemaxon
Polarizability23.36 Å3Chemaxon
Number of Rings0Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption-0.6298
Blood Brain Barrier+0.8694
Caco-2 permeable-0.8469
P-glycoprotein substrateNon-substrate0.7613
P-glycoprotein inhibitor INon-inhibitor0.9517
P-glycoprotein inhibitor IINon-inhibitor0.9886
Renal organic cation transporterNon-inhibitor0.9576
CYP450 2C9 substrateNon-substrate0.8399
CYP450 2D6 substrateNon-substrate0.8295
CYP450 3A4 substrateNon-substrate0.7275
CYP450 1A2 substrateNon-inhibitor0.9496
CYP450 2C9 inhibitorNon-inhibitor0.9364
CYP450 2D6 inhibitorNon-inhibitor0.9342
CYP450 2C19 inhibitorNon-inhibitor0.9427
CYP450 3A4 inhibitorNon-inhibitor0.8919
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9905
Ames testAMES toxic0.7948
CarcinogenicityNon-carcinogens0.9386
BiodegradationReady biodegradable0.8085
Rat acute toxicity1.5829 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9946
hERG inhibition (predictor II)Non-inhibitor0.9654
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)GC-MSsplash10-054t-1920100000-5ce9a082971db6d9e2e9
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-053u-9630000000-344be03dbe2132b00c88
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-054t-1920100000-5ce9a082971db6d9e2e9
MS/MS Spectrum - Quattro_QQQ 10V, PositiveLC-MS/MSsplash10-0udi-0090000000-50bd1555ededc1afde80
MS/MS Spectrum - Quattro_QQQ 25V, PositiveLC-MS/MSsplash10-0udi-0290000000-385ca433f03af7530f47
MS/MS Spectrum - Quattro_QQQ 40V, PositiveLC-MS/MSsplash10-0ue9-5490000000-95d45a9cd2bb6249d3a2
LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , PositiveLC-MS/MSsplash10-001i-9510000000-5f29ca903abe05256c83
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-001i-9510000000-5f29ca903abe05256c83
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0fk9-0950000000-f3218bac2f0d154384e6
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0089-0900000000-3c835d6f558e11ea801e
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-000i-9600000000-d9e1c9a96b29945e0143
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-004i-3900000000-714436a2b41ad933a2c8
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-000i-9100000000-63632faa0431df81b6dc
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-001l-9100000000-ee5552c2760da230f833
1H NMR Spectrum1D NMRNot Applicable
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
[1H,13C] 2D NMR Spectrum2D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-161.4578058
predicted
DarkChem Lite v0.1.0
[M-H]-161.5295058
predicted
DarkChem Lite v0.1.0
[M-H]-161.3289058
predicted
DarkChem Lite v0.1.0
[M-H]-161.3575058
predicted
DarkChem Lite v0.1.0
[M-H]-155.29776
predicted
DeepCCS 1.0 (2019)
[M+H]+160.3565058
predicted
DarkChem Lite v0.1.0
[M+H]+156.2805441
predicted
DarkChem Standard v0.1.0
[M+H]+160.2429058
predicted
DarkChem Lite v0.1.0
[M+H]+160.2652058
predicted
DarkChem Lite v0.1.0
[M+H]+157.65579
predicted
DeepCCS 1.0 (2019)
[M+Na]+160.4274058
predicted
DarkChem Lite v0.1.0
[M+Na]+160.4082058
predicted
DarkChem Lite v0.1.0
[M+Na]+160.2889058
predicted
DarkChem Lite v0.1.0
[M+Na]+160.3542058
predicted
DarkChem Lite v0.1.0
[M+Na]+163.74893
predicted
DeepCCS 1.0 (2019)

Targets

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Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Protein homodimerization activity
Specific Function
Not Available
Gene Name
GSS
Uniprot ID
P48637
Uniprot Name
Glutathione synthetase
Molecular Weight
52384.325 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
  2. 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]
  3. 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