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(1R)-Glutathionyl-(2R)-hydroxy-1,2-dihydronaphthalene (M2MDB000852)

Record Information
Version2.0
Creation Date2012-05-31 14:22:19 -0600
Update Date2015-06-03 17:19:06 -0600
Secondary Accession Numbers
  • ECMDB20003
Identification
Name:(1R)-Glutathionyl-(2R)-hydroxy-1,2-dihydronaphthalene
Description(1r)-glutathionyl-(2r)-hydroxy-1,2-dihydronaphthalene 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
MOLSDFPDBSMILESInChI
Synonyms:
  • (1R, 2S)-1,2-dihydronaphthalene-1,2-diol
  • (1R,2S)-1,2-dihydro-1,2-dihyroxynaphthalene
  • (1R,2S)-1,2-dihydronaphthalene-1,2-diol
  • (1R,2S)-naphthalene-1,2-dihydrodiol
  • (2S)-2-amino-5-(2R)-1-(carboxymethylamino)-3-(1R,2R)-2-Hydroxy-1,2-dihydronaphthalen-1-ylsulfanyl-1-oxopropan-2-ylamino-5-oxopentanoate
  • (2S)-2-amino-5-(2R)-1-(carboxymethylamino)-3-(1R,2R)-2-hydroxy-1,2-dihydronaphthalen-1-ylsulfanyl-1-oxopropan-2-ylamino-5-oxopentanoic acid
  • (2S)-2-amino-5-(2R)-1-(carboxymethylamino)-3-(1R,2R)-2-Hydroxy-1,2-dihydronaphthalen-1-ylsulphanyl-1-oxopropan-2-ylamino-5-oxopentanoate
  • (2S)-2-amino-5-(2R)-1-(carboxymethylamino)-3-(1R,2R)-2-Hydroxy-1,2-dihydronaphthalen-1-ylsulphanyl-1-oxopropan-2-ylamino-5-oxopentanoic acid
  • 3,4-dihydronaphthalene-3,4-diol
  • cis-1,2-dihydronaphthalene-1,2-diol
  • cis-1,2-Dihydronaphthalene-1,2-diol
  • Cis-1,2-dihydroxy-1,2-dihydronaphthalene
  • L-g-Glutamyl-S-(1R,2R)-2-hydroxy-1,2-dihydro-1-naphthalenyl-L-cysteinylglycine
  • L-gamma-Glutamyl-S-(1R,2R)-2-hydroxy-1,2-dihydro-1-naphthalenyl-L-cysteinylglycine
  • L-γ-Glutamyl-S-(1R,2R)-2-hydroxy-1,2-dihydro-1-naphthalenyl-L-cysteinylglycine
Chemical Formula:C20H25N3O7S
Weight:Average: 451.493
Monoisotopic: 451.141320859
InChI Key:UWBZAZWPTVBBEL-OIPACUDHSA-N
InChI:InChI=1S/C20H25N3O7S/c21-13(20(29)30)6-8-16(25)23-14(19(28)22-9-17(26)27)10-31-18-12-4-2-1-3-11(12)5-7-15(18)24/h1-5,7,13-15,18,24H,6,8-10,21H2,(H,22,28)(H,23,25)(H,26,27)(H,29,30)/t13-,14-,15+,18+/m0/s1
CAS number:Not Available
IUPAC Name:(2S)-2-amino-4-{[(1R)-1-[(carboxymethyl)-C-hydroxycarbonimidoyl]-2-{[(1R,2R)-2-hydroxy-1,2-dihydronaphthalen-1-yl]sulfanyl}ethyl]-C-hydroxycarbonimidoyl}butanoic acid
Traditional IUPAC Name:(2S)-2-amino-4-{[(1R)-1-(carboxymethyl-C-hydroxycarbonimidoyl)-2-{[(1R,2R)-2-hydroxy-1,2-dihydronaphthalen-1-yl]sulfanyl}ethyl]-C-hydroxycarbonimidoyl}butanoic acid
SMILES:[H][C@](N)(CCC(O)=N[C@@]([H])(CS[C@]1([H])C2=CC=CC=C2C=C[C@@]1([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
  • Naphthalene
  • L-alpha-amino acid
  • Fatty acyl
  • N-acyl-amine
  • Fatty amide
  • Dicarboxylic acid or derivatives
  • Benzenoid
  • Secondary alcohol
  • Secondary carboxylic acid amide
  • Amino acid
  • Amino acid or derivatives
  • Carboxamide group
  • Dialkylthioether
  • Carboxylic acid
  • Sulfenyl compound
  • Thioether
  • Primary amine
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Alcohol
  • Carbonyl group
  • Hydrocarbon derivative
  • Amine
  • Organic oxide
  • Primary aliphatic amine
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Aromatic homopolycyclic compound
Molecular FrameworkAromatic homopolycyclic compounds
External Descriptors
Physical Properties
State:Not Available
Charge:-2
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility0.058 g/LALOGPS
logP-1.6ALOGPS
logP-1.7ChemAxon
logS-3.9ALOGPS
pKa (Strongest Acidic)1.96ChemAxon
pKa (Strongest Basic)9.54ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area186.03 ŲChemAxon
Rotatable Bond Count11ChemAxon
Refractivity114.1 m³·mol⁻¹ChemAxon
Polarizability45 ųChemAxon
Number of Rings2ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
(1S,2R)-Naphthalene 1,2-oxide + Glutathione <> (1R)-Glutathionyl-(2R)-hydroxy-1,2-dihydronaphthalene
Naphthalene epoxide + Glutathione + (1R,2S)-Naphthalene 1,2-oxide > (1R)-Glutathionyl-(2R)-hydroxy-1,2-dihydronaphthalene
SMPDB Pathways:
Glutathione metabolismPW000833 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:
EcoCyc Pathways:Not Available
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0002-3915700000-d663b106af5ff8f05ab5View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-0gb9-6491156000-387722deb85a575c8d1fView 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_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_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 ("(1R)-Glutathionyl-(2R)-hydroxy-1,2-dihydronaphthalene,2TBDMS,#4" TMS) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00e9-3126900000-e852fce9919b502e2de0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-9226100000-8ad87012ef3d3e1f9b0bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00di-9221000000-4da054dda6edae051eb7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0zir-0513900000-99965a9d9f77c397a0b8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a6r-0910000000-b0f870f10a0d4c614ccfView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-002f-1900000000-e7b810e5d1d7c3d02dd0View in MoNA
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
1D NMR13C 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
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI ID33993
HMDB IDHMDB0060299
Pubchem Compound ID11954046
Kegg IDC14793
ChemSpider ID10128341
Wikipedia IDNot Available
BioCyc IDCIS-12-DIHYDRONAPHTHALENE-12-DIOL
EcoCyc IDCIS-12-DIHYDRONAPHTHALENE-12-DIOL

Enzymes

Protein Details
1. Glutathione S-transferase
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.
Protein Details
2. GSH-dependent disulfide bond oxidoreductase
General function:
Not Available
Specific function:
Not Available
Gene Name:
yfcG
Uniprot ID:
P77526
Molecular weight:
Not Available