Record Information
Version2.0
Creation Date2012-05-31 14:26:19 -0600
Update Date2015-06-03 17:19:16 -0600
Secondary Accession Numbers
  • ECMDB20078
Identification
Name:3,4-Dihydro-3-hydroxy-4-S-glutathionyl bromobenzene
Description3,4-dihydro-3-hydroxy-4-s-glutathionyl bromobenzene belongs to the class of Peptides. These are compounds containing an amide derived from two or more amino carboxylic acid molecules (the same or different) by formation of a covalent bond from the carbonyl carbon of one to the nitrogen atom of another. (inferred from compound structure)
Structure
Thumb
Synonyms:
  • (2S)-2-amino-5-(2R)-3-(4-bromo-6-Hydroxycyclohexa-2,4-dien-1-yl)sulfanyl-1-(carboxymethylamino)-1-oxopropan-2-ylamino-5-oxopentanoate
  • (2S)-2-amino-5-(2R)-3-(4-bromo-6-hydroxycyclohexa-2,4-dien-1-yl)sulfanyl-1-(carboxymethylamino)-1-oxopropan-2-ylamino-5-oxopentanoic acid
  • (2S)-2-amino-5-(2R)-3-(4-bromo-6-Hydroxycyclohexa-2,4-dien-1-yl)sulphanyl-1-(carboxymethylamino)-1-oxopropan-2-ylamino-5-oxopentanoate
  • (2S)-2-amino-5-(2R)-3-(4-bromo-6-Hydroxycyclohexa-2,4-dien-1-yl)sulphanyl-1-(carboxymethylamino)-1-oxopropan-2-ylamino-5-oxopentanoic acid
  • L-g-Glutamyl-S-(4-bromo-6-hydroxy-2,4-cyclohexadien-1-yl)-L-cysteinylglycine
  • L-gamma-Glutamyl-S-(4-bromo-6-hydroxy-2,4-cyclohexadien-1-yl)-L-cysteinylglycine
  • L-γ-Glutamyl-S-(4-bromo-6-hydroxy-2,4-cyclohexadien-1-yl)-L-cysteinylglycine
Chemical Formula:C16H22BrN3O7S
Weight:Average: 480.331
Monoisotopic: 479.03618341
InChI Key:WIPMNDWTVDZAHE-JYBOHDQNSA-N
InChI:InChI=1S/C16H22BrN3O7S/c17-8-1-3-12(11(21)5-8)28-7-10(15(25)19-6-14(23)24)20-13(22)4-2-9(18)16(26)27/h1,3,5,9-12,21H,2,4,6-7,18H2,(H,19,25)(H,20,22)(H,23,24)(H,26,27)/t9-,10-,11?,12?/m0/s1
CAS number:Not Available
IUPAC Name:(2S)-2-amino-4-{[(1R)-2-[(4-bromo-6-hydroxycyclohexa-2,4-dien-1-yl)sulfanyl]-1-[(carboxymethyl)-C-hydroxycarbonimidoyl]ethyl]-C-hydroxycarbonimidoyl}butanoic acid
Traditional IUPAC Name:C16H22brN3O7S
SMILES:[H][C@](N)(CCC(O)=N[C@@]([H])(CSC1([H])C=CC(Br)=CC1([H])O)C(O)=NCC(O)=O)C(O)=O
Chemical Taxonomy
Description belongs to the class of organic compounds known as oligopeptides. These are organic compounds containing a sequence of between three and ten alpha-amino acids joined by peptide bonds.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentOligopeptides
Alternative Parents
Substituents
  • Alpha-oligopeptide
  • Gamma-glutamyl alpha peptide
  • Glutamine or derivatives
  • N-acyl-alpha amino acid or derivatives
  • N-acyl-alpha-amino acid
  • Alpha-amino acid amide
  • Cysteine or derivatives
  • Alpha-amino acid
  • N-substituted-alpha-amino acid
  • Alpha-amino acid or derivatives
  • L-alpha-amino acid
  • Hydroxy fatty acid
  • Halogenated fatty acid
  • Fatty amide
  • Fatty acyl
  • N-acyl-amine
  • Dicarboxylic acid or derivatives
  • Amino acid or derivatives
  • Amino acid
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Carboxamide group
  • Bromoalkene
  • Carboxylic acid
  • Haloalkene
  • Dialkylthioether
  • Sulfenyl compound
  • Vinyl halide
  • Vinyl bromide
  • Thioether
  • Amine
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Alcohol
  • Carbonyl group
  • Primary aliphatic amine
  • Hydrocarbon derivative
  • Primary amine
  • Organosulfur compound
  • Organohalogen compound
  • Organobromide
  • Organonitrogen compound
  • Organooxygen compound
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External Descriptors
Physical Properties
State:Not Available
Charge:-2
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility0.089 g/LALOGPS
logP-1.8ALOGPS
logP-2.4ChemAxon
logS-3.7ALOGPS
pKa (Strongest Acidic)1.86ChemAxon
pKa (Strongest Basic)9.54ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area186.03 ŲChemAxon
Rotatable Bond Count11ChemAxon
Refractivity106.82 m³·mol⁻¹ChemAxon
Polarizability42.71 ųChemAxon
Number of Rings1ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
SMPDB Pathways:
glutathione metabolism IIIPW002018 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:Not Available
EcoCyc Pathways:
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00di-5922800000-c40ed874d9c5502a4d1aView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-000y-5190108000-4782944b55c20ef6d12aView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_2_4) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_3_2) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_3_3) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_3_6) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_3_8) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_3_9) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_3_10) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS ("3,4-Dihydro-3-hydroxy-4-S-glutathionyl bromobenzene,2TBDMS,#4" TMS) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-02ha-2023900000-a99b2d602d251ac08e3bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-9145100000-5e3af90d25319ad465d6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00di-9241000000-6ee8399683c139ed4a2cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0h00-0231900000-5c894a3884a1afaf36ffView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0f79-0971100000-009d5316a5746058cd36View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0udl-1920000000-d4ea4fbd0aa6eae7ab02View in MoNA
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
References
References:
  • Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
  • Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI ID34324
HMDB IDHMDB0060381
Pubchem Compound ID11954066
Kegg IDC14847
ChemSpider ID10128361
Wikipedia IDNot Available
BioCyc IDDIHYDRO-DIOH-BENZOATE
EcoCyc IDDIHYDRO-DIOH-BENZOATE

Enzymes

General function:
Involved in protein binding
Specific function:
Conjugation of reduced glutathione to a wide number of exogenous and endogenous hydrophobic electrophiles
Gene Name:
gst
Uniprot ID:
P0A9D2
Molecular weight:
22868
Reactions
RX + glutathione = HX + R-S-glutathione.
General function:
Not Available
Specific function:
Not Available
Gene Name:
yfcG
Uniprot ID:
P77526
Molecular weight:
Not Available