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Identification
Namegamma-Glutamylcysteine
Accession NumberDB03408  (EXPT00168)
TypeSmall Molecule
GroupsExperimental
DescriptionNot 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
External Identifiers Not Available
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International BrandsNot Available
Brand mixturesNot Available
SaltsNot Available
CategoriesNot Available
UNIIM984VJS48P
CAS number636-58-8
WeightAverage: 250.272
Monoisotopic: 250.062342258
Chemical FormulaC8H14N2O5S
InChI KeyRITKHVBHSGLULN-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
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as gamma-glutamyl amino acids. These are dipeptides consisting of any C-terminal amino acid having a gamma-glutamyl residue attached at the N alpha-position.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentGamma-glutamyl amino acids
Alternative Parents
Substituents
  • Gamma-glutamyl alpha-amino acid
  • N-acyl-aliphatic-alpha amino acid
  • N-acyl-alpha amino acid or derivatives
  • N-acyl-alpha-amino acid
  • L-alpha-amino acid
  • Alpha-amino acid or derivatives
  • N-substituted-alpha-amino acid
  • Alpha-amino acid
  • Amino fatty acid
  • Fatty acyl
  • Fatty acid
  • N-acyl-amine
  • Fatty amide
  • Dicarboxylic acid or derivatives
  • Secondary carboxylic acid amide
  • Carboxamide group
  • Carboxylic acid
  • Carboxylic acid amide
  • Alkylthiol
  • Hydrocarbon derivative
  • Primary amine
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Carbonyl group
  • Amine
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Pharmacology
IndicationNot Available
PharmacodynamicsNot Available
Mechanism of actionNot Available
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organismsNot Available
Pathways
PathwayCategorySMPDB ID
Beta-mercaptolactate-cysteine disulfiduriaDiseaseSMP00499
Glutamate MetabolismMetabolicSMP00072
5-OxoprolinuriaDiseaseSMP00143
HomocarnosinosisDiseaseSMP00385
Cysteine MetabolismMetabolicSMP00013
Glutathione MetabolismMetabolicSMP00015
Gamma-Glutamyltransferase DeficiencyDiseaseSMP00183
Gamma-glutamyl-transpeptidase deficiencyDiseaseSMP00501
Succinic semialdehyde dehydrogenase deficiencyDiseaseSMP00567
Cystinosis, ocular nonnephropathicDiseaseSMP00722
2-Hydroxyglutric Aciduria (D And L Form)DiseaseSMP00136
4-Hydroxybutyric Aciduria/Succinic Semialdehyde Dehydrogenase DeficiencyDiseaseSMP00243
Glutathione Synthetase DeficiencyDiseaseSMP00337
Hyperinsulinism-Hyperammonemia SyndromeDiseaseSMP00339
5-oxoprolinase deficiencyDiseaseSMP00500
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
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 )
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental PropertiesNot 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 FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)splash10-054t-1920100000-5ce9a082971db6d9e2e9View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0udi-0090000000-50bd1555ededc1afde80View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0udi-0290000000-385ca433f03af7530f47View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0ue9-5490000000-95d45a9cd2bb6249d3a2View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-001i-9510000000-5f29ca903abe05256c83View in MoNA
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
References
Synthesis Reference

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

US20030124684
General ReferencesNot Available
External Links
ATC CodesNot Available
AHFS CodesNot Available
PDB Entries
FDA labelNot Available
MSDSNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

Targets

Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
Protein homodimerization activity
Specific Function:
Not Available
Gene Name:
GSS
Uniprot ID:
P48637
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 ]
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Drug created on June 13, 2005 07:24 / Updated on May 03, 2016 13:47