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1-Nitro-7-glutathionyl-8-hydroxy-7,8-dihydronaphthalene (M2MDB000875)

Record Information
Version2.0
Creation Date2012-05-31 14:23:35 -0600
Update Date2015-06-03 17:19:09 -0600
Secondary Accession Numbers
  • ECMDB20026
Identification
Name:1-Nitro-7-glutathionyl-8-hydroxy-7,8-dihydronaphthalene
Description1-nitro-7-glutathionyl-8-hydroxy-7,8-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:
  • (2S)-2-amino-5-(2R)-1-(carboxymethylamino)-3-(1-Hydroxy-8-nitro-1,2-dihydronaphthalen-2-yl)sulfanyl-1-oxopropan-2-ylamino-5-oxopentanoate
  • (2S)-2-amino-5-(2R)-1-(carboxymethylamino)-3-(1-hydroxy-8-nitro-1,2-dihydronaphthalen-2-yl)sulfanyl-1-oxopropan-2-ylamino-5-oxopentanoic acid
  • (2S)-2-amino-5-(2R)-1-(carboxymethylamino)-3-(1-Hydroxy-8-nitro-1,2-dihydronaphthalen-2-yl)sulphanyl-1-oxopropan-2-ylamino-5-oxopentanoate
  • (2S)-2-amino-5-(2R)-1-(carboxymethylamino)-3-(1-Hydroxy-8-nitro-1,2-dihydronaphthalen-2-yl)sulphanyl-1-oxopropan-2-ylamino-5-oxopentanoic acid
  • L-g-Glutamyl-S-(1-hydroxy-8-nitro-1,2-dihydro-2-naphthalenyl)-L-cysteinylglycine
  • L-gamma-Glutamyl-S-(1-hydroxy-8-nitro-1,2-dihydro-2-naphthalenyl)-L-cysteinylglycine
  • L-γ-Glutamyl-S-(1-hydroxy-8-nitro-1,2-dihydro-2-naphthalenyl)-L-cysteinylglycine
Chemical Formula:C20H24N4O9S
Weight:Average: 496.491
Monoisotopic: 496.126399076
InChI Key:FCTXJUPCCZHZHU-WXFCVCCESA-N
InChI:InChI=1S/C20H24N4O9S/c21-11(20(30)31)5-7-15(25)23-12(19(29)22-8-16(26)27)9-34-14-6-4-10-2-1-3-13(24(32)33)17(10)18(14)28/h1-4,6,11-12,14,18,28H,5,7-9,21H2,(H,22,29)(H,23,25)(H,26,27)(H,30,31)/t11-,12-,14?,18?/m0/s1
CAS number:Not Available
IUPAC Name:(2S)-2-amino-4-{[(1R)-1-[(carboxymethyl)-C-hydroxycarbonimidoyl]-2-[(1-hydroxy-8-nitro-1,2-dihydronaphthalen-2-yl)sulfanyl]ethyl]-C-hydroxycarbonimidoyl}butanoic acid
Traditional IUPAC Name:(2S)-2-amino-4-{[(1R)-1-(carboxymethyl-C-hydroxycarbonimidoyl)-2-[(1-hydroxy-8-nitro-1,2-dihydronaphthalen-2-yl)sulfanyl]ethyl]-C-hydroxycarbonimidoyl}butanoic acid
SMILES:[H][C@](N)(CCC(O)=N[C@@]([H])(CSC1([H])C=CC2=C(C(=CC=C2)N(=O)=O)C1([H])O)C(O)=NCC(O)=O)C(O)=O
Chemical Taxonomy
Description belongs to the class of organic compounds known as naphthalenes. Naphthalenes are compounds containing a naphthalene moiety, which consists of two fused benzene rings.
KingdomOrganic compounds
Super ClassBenzenoids
ClassNaphthalenes
Sub ClassNot Available
Direct ParentNaphthalenes
Alternative Parents
Substituents
  • Naphthalene
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Aromatic alcohol
  • Primary alcohol
  • Organooxygen compound
  • Alcohol
  • Aromatic homopolycyclic compound
Molecular FrameworkAromatic homopolycyclic compounds
External Descriptors
Physical Properties
State:Not Available
Charge:-3
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility0.04 g/LALOGPS
logP-1.5ALOGPS
logP-1.7ChemAxon
logS-4.1ALOGPS
pKa (Strongest Acidic)1.83ChemAxon
pKa (Strongest Basic)9.54ChemAxon
Physiological Charge-3ChemAxon
Hydrogen Acceptor Count12ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area231.85 ŲChemAxon
Rotatable Bond Count12ChemAxon
Refractivity121.43 m³·mol⁻¹ChemAxon
Polarizability47.08 ųChemAxon
Number of Rings2ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
1-Nitronaphthalene-7,8-oxide + Glutathione <> 1-Nitro-7-glutathionyl-8-hydroxy-7,8-dihydronaphthalene
Glutathione + 1-Nitronaphthalene-7,8-oxide > 1-Nitro-7-glutathionyl-8-hydroxy-7,8-dihydronaphthalene
SMPDB Pathways:
glutathione metabolism IIPW001927 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:Not Available
EcoCyc Pathways:Not Available
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-2501900000-33399c20b46700295800View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-006x-5901244000-a02271b0549de9b44fcfView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 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 (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_8) - 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 ("1-Nitro-7-glutathionyl-8-hydroxy-7,8-dihydronaphthalene,2TBDMS,#4" TMS) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0000900000-91cfdbb0997afec136d0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-006t-3000900000-02adc1de44bd9fc5ba98View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00di-9110000000-57cc41b896c948c09835View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0000900000-01e07ae0d7e7e473991fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-1110900000-9ca859a4f74cfa0533c5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-9830000000-0626d28f448ecdd5bb0eView 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 ID34102
HMDB IDHMDB0060329
Pubchem Compound ID11954055
Kegg IDC14804
ChemSpider ID10128350
Wikipedia IDNot Available
BioCyc IDNot Available

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