1-Nitro-5-hydroxy-6-glutathionyl-5,6-dihydronaphthalene (ECMDB20025) (M2MDB000874)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes (2)XML
Proteins (887)
Record Information
Version2.0
Creation Date2012-05-31 14:23:32 -0600
Update Date2015-06-03 17:19:09 -0600
Secondary Accession Numbers
  • ECMDB20025
Identification
Name:1-Nitro-5-hydroxy-6-glutathionyl-5,6-dihydronaphthalene
Description1-nitro-5-hydroxy-6-glutathionyl-5,6-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-5-nitro-1,2-dihydronaphthalen-2-yl)sulfanyl-1-oxopropan-2-ylamino-5-oxopentanoate
  • (2S)-2-amino-5-(2R)-1-(carboxymethylamino)-3-(1-hydroxy-5-nitro-1,2-dihydronaphthalen-2-yl)sulfanyl-1-oxopropan-2-ylamino-5-oxopentanoic acid
  • (2S)-2-amino-5-(2R)-1-(carboxymethylamino)-3-(1-Hydroxy-5-nitro-1,2-dihydronaphthalen-2-yl)sulphanyl-1-oxopropan-2-ylamino-5-oxopentanoate
  • (2S)-2-amino-5-(2R)-1-(carboxymethylamino)-3-(1-Hydroxy-5-nitro-1,2-dihydronaphthalen-2-yl)sulphanyl-1-oxopropan-2-ylamino-5-oxopentanoic acid
  • L-g-Glutamyl-S-(1-hydroxy-5-nitro-1,2-dihydro-2-naphthalenyl)-L-cysteinylglycine
  • L-gamma-Glutamyl-S-(1-hydroxy-5-nitro-1,2-dihydro-2-naphthalenyl)-L-cysteinylglycine
  • L-γ-Glutamyl-S-(1-hydroxy-5-nitro-1,2-dihydro-2-naphthalenyl)-L-cysteinylglycine
Chemical Formula:C20H24N4O9S
Weight:Average: 496.491
Monoisotopic: 496.126399076
InChI Key:SFJZEQDXMXSLGC-RJXQQRCHSA-N
InChI:InChI=1S/C20H24N4O9S/c21-12(20(30)31)5-7-16(25)23-13(19(29)22-8-17(26)27)9-34-15-6-4-10-11(18(15)28)2-1-3-14(10)24(32)33/h1-4,6,12-13,15,18,28H,5,7-9,21H2,(H,22,29)(H,23,25)(H,26,27)(H,30,31)/t12-,13-,15?,18?/m0/s1
CAS number:Not Available
IUPAC Name:(2S)-2-amino-4-{[(1R)-1-[(carboxymethyl)-C-hydroxycarbonimidoyl]-2-[(1-hydroxy-5-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-5-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=C2N(=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 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
  • N-acyl-alpha amino acid or derivatives
  • 1-nitronaphthalene
  • Alpha-amino acid amide
  • Cysteine or derivatives
  • Alpha-amino acid
  • N-substituted-alpha-amino acid
  • Alpha-amino acid or derivatives
  • L-alpha-amino acid
  • Naphthalene
  • Nitroaromatic compound
  • Dicarboxylic acid or derivatives
  • Fatty amide
  • N-acyl-amine
  • Fatty acyl
  • Benzenoid
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Amino acid or derivatives
  • C-nitro compound
  • Carboxamide group
  • Organic nitro compound
  • Amino acid
  • Sulfenyl compound
  • Thioether
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Allyl-type 1,3-dipolar organic compound
  • Organic oxoazanium
  • Dialkylthioether
  • Carboxylic acid
  • Primary amine
  • Primary aliphatic amine
  • Organic oxygen compound
  • Organic nitrogen compound
  • Alcohol
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Carbonyl group
  • Organonitrogen compound
  • Amine
  • Organic zwitterion
  • Organic oxide
  • Organooxygen compound
  • Organosulfur 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 Solubility0.045 g/LALOGPS
logP-1.4ALOGPS
logP-1.7ChemAxon
logS-4ALOGPS
pKa (Strongest Acidic)1.83ChemAxon
pKa (Strongest Basic)9.54ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count12ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area231.85 ŲChemAxon
Rotatable Bond Count12ChemAxon
Refractivity121.43 m³·mol⁻¹ChemAxon
Polarizability47.19 ųChemAxon
Number of Rings2ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
1-Nitronaphthalene-5,6-oxide + Glutathione <> 1-Nitro-5-hydroxy-6-glutathionyl-5,6-dihydronaphthalene
1-Nitronaphthalene-5,6-oxide + Glutathione > 1-Nitro-5-hydroxy-6-glutathionyl-5,6-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, Positivesplash10-0006-3602900000-08a1ea646555a202d38bView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-0096-6901144000-b14e266087a2f14e12a0View 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-5-hydroxy-6-glutathionyl-5,6-dihydronaphthalene,2TBDMS,#4" TMS) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0000900000-77a3b95f2be8c4054908View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-006t-3000900000-6ffc994cc20e79922b4aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00di-9120000000-da578bac9f9fcc40d092View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0000900000-15548fccf325d21f7dafView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-1110900000-0a53ffa1b9349606b2b9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-9840000000-f71aca527987b3e71d98View 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
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI ID34101
HMDB IDHMDB0060327
Pubchem Compound ID11954056
Kegg IDC14805
ChemSpider ID10128351
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