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Identification
NameGamma-Glutamylcysteine
Accession NumberDB03408  (EXPT00168)
Typesmall molecule
Groupsexperimental
DescriptionNot Available
Structure
Thumb
SynonymsNot Available
SaltsNot Available
Brand namesNot Available
Brand mixturesNot Available
CategoriesNot Available
CAS number686-58-8
WeightAverage: 250.272
Monoisotopic: 250.062342258
Chemical FormulaC8H14N2O5S
InChI KeyRITKHVBHSGLULN-CRCLSJGQSA-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-{[(1S)-1-carboxy-2-sulfanylethyl]carbamoyl}butanoic acid
SMILES
N[C@@H](CCC(=O)N[C@H](CS)C(O)=O)C(O)=O
Mass SpecNot Available
Taxonomy
KingdomOrganic Compounds
SuperclassOrganic Acids and Derivatives
ClassCarboxylic Acids and Derivatives
SubclassAmino Acids, Peptides, and Analogues
Direct parentN-acyl-alpha Amino Acids
Alternative parentsAmino Fatty Acids; Dicarboxylic Acids and Derivatives; Polyols; Secondary Carboxylic Acid Amides; Enolates; Alkylthiols; Polyamines; Carboxylic Acids; Monoalkylamines
Substituentsdicarboxylic acid derivative; polyol; secondary carboxylic acid amide; carboxamide group; alkylthiol; polyamine; carboxylic acid; enolate; amine; primary aliphatic amine; primary amine; organonitrogen compound
Classification descriptionThis compound belongs to the n-acyl-alpha amino acids. These are compounds containing an alpha amino acid which bears an acyl group at his terminal nitrogen atom.
Pharmacology
IndicationNot Available
PharmacodynamicsNot Available
Mechanism of actionNot Available
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
Metabolism
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organismsNot Available
Pathways
PathwayCategorySMPDB ID
2-Hydroxyglutric Aciduria (D And L Form)DiseaseSMP00136
4-Hydroxybutyric Aciduria/Succinic Semialdehyde Dehydrogenase DeficiencyDiseaseSMP00243
5-oxoprolinase deficiencyDiseaseSMP00500
5-OxoprolinuriaDiseaseSMP00143
Beta-mercaptolactate-cysteine disulfiduriaDiseaseSMP00499
Cysteine MetabolismMetabolicSMP00013
Cystinosis, ocular nonnephropathicDiseaseSMP00722
Gamma-glutamyl-transpeptidase deficiencyDiseaseSMP00501
Succinic semialdehyde dehydrogenase deficiencyDiseaseSMP00567
Glutathione Synthetase DeficiencyDiseaseSMP00337
Gamma-Glutamyltransferase DeficiencyDiseaseSMP00183
Glutamate MetabolismMetabolicSMP00072
Glutathione MetabolismMetabolicSMP00015
HomocarnosinosisDiseaseSMP00385
Hyperinsulinism-Hyperammonemia SyndromeDiseaseSMP00339
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
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 substrate Non-inhibitor 0.9364
CYP450 2D6 substrate Non-inhibitor 0.9342
CYP450 2C19 substrate Non-inhibitor 0.9427
CYP450 3A4 substrate 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
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
Statesolid
Experimental PropertiesNot Available
Predicted Properties
PropertyValueSource
water solubility2.62e+00 g/lALOGPS
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 area129.72ChemAxon
rotatable bond count7ChemAxon
refractivity56.31ChemAxon
polarizability23.69ChemAxon
number of rings0ChemAxon
bioavailability1ChemAxon
rule of fiveYesChemAxon
Ghose filterNoChemAxon
Veber's ruleNoChemAxon
MDDR-like ruleNoChemAxon
Spectra
SpectraNot Available
References
Synthesis Reference

Hiroaki Nishiuchi, “Method for producing gamma-glutamylcysteine.” U.S. Patent US20030124684, issued July 03, 2003.

US20030124684
General ReferenceNot Available
External Links
ResourceLink
KEGG CompoundC00669
PubChem Compound13922647
PubChem Substance46506032
ChEBI17515
ChEMBL
HET3GC
ATC CodesNot Available
AHFS CodesNot Available
PDB Entries
FDA labelNot Available
MSDSNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

Targets

1. Glutathione synthetase

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Glutathione synthetase P48637 Details

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
  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
  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

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Drug created on June 13, 2005 07:24 / Updated on September 16, 2013 17:21