gamma-Glutamylcysteine

Identification

Name
gamma-Glutamylcysteine
Accession Number
DB03408  (EXPT00168)
Type
Small Molecule
Groups
Experimental
Description
Not Available
Structure
Thumb
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
Categories
UNII
M984VJS48P
CAS number
636-58-8
Weight
Average: 250.272
Monoisotopic: 250.062342258
Chemical Formula
C8H14N2O5S
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[[email protected]@H](CCC(=O)N[[email protected]@H](CS)C(O)=O)C(O)=O

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UGlutathione synthetaseNot AvailableHuman
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
Toxicity
Not Available
Affected organisms
Not Available
Pathways
PathwayCategory
Beta-mercaptolactate-cysteine disulfiduriaDisease
Glutamate MetabolismMetabolic
5-OxoprolinuriaDisease
HomocarnosinosisDisease
2-Hydroxyglutric Aciduria (D And L Form)Disease
4-Hydroxybutyric Aciduria/Succinic Semialdehyde Dehydrogenase DeficiencyDisease
Glutathione Synthetase DeficiencyDisease
Hyperinsulinism-Hyperammonemia SyndromeDisease
5-oxoprolinase deficiencyDisease
Cysteine MetabolismMetabolic
Glutathione MetabolismMetabolic
Gamma-Glutamyltransferase DeficiencyDisease
Gamma-glutamyl-transpeptidase deficiencyDisease
Succinic semialdehyde dehydrogenase deficiencyDisease
Cystinosis, ocular nonnephropathicDisease
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

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
HMDB01049
KEGG Compound
C00669
PubChem Compound
123938
PubChem Substance
46506032
ChemSpider
110467
ChEBI
17515
ChEMBL
CHEMBL460831
HET
3GC
Wikipedia
Gamma-Glutamylcysteine
PDB Entries
1m0w / 2bu3 / 3kak / 4x8d

Clinical Trials

Clinical Trials
Not Available

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-MSNot Available
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
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-001i-9510000000-5f29ca903abe05256c83
1H NMR Spectrum1D NMRNot Applicable
[1H,13C] 2D NMR Spectrum2D NMRNot Applicable

Taxonomy

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
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
show 16 more
Molecular Framework
Aliphatic acyclic compounds
External Descriptors
gamma-glutamylcysteine (CHEBI:17515)

Targets

Kind
Protein
Organism
Human
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. [PubMed:17139284]
  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. [PubMed:17016423]
  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. [PubMed:10592235]

Drug created on June 13, 2005 07:24 / Updated on November 09, 2017 03:27