Structural search and advanced query search is temporarily unavailable. We are working to fix this issue. Thank you for your support and patience.


(1S)-Hydroxy-(2S)-glutathionyl-1,2-dihydronaphthalene (M2MDB000855)

Record Information
Version2.0
Creation Date2012-05-31 14:22:29 -0600
Update Date2015-06-03 17:19:06 -0600
Secondary Accession Numbers
  • ECMDB20006
Identification
Name:(1S)-Hydroxy-(2S)-glutathionyl-1,2-dihydronaphthalene
Description(1s)-hydroxy-(2s)-glutathionyl-1,2-dihydronaphthalene is a member of the chemical class known as 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.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms:
  • (1R)-Hydroxy-(2R)-glutathionyl-1,2-dihydronaphthalene
  • (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
  • 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
Chemical Formula:C20H25N3O7S
Weight:Average: 451.493
Monoisotopic: 451.141320859
InChI Key:HBBDHJOSZGOTBV-XSWJXKHESA-N
InChI:InChI=1S/C20H25N3O7S/c21-13(20(29)30)6-8-16(24)23-14(19(28)22-9-17(25)26)10-31-15-7-5-11-3-1-2-4-12(11)18(15)27/h1-5,7,13-15,18,27H,6,8-10,21H2,(H,22,28)(H,23,24)(H,25,26)(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-{[(1S,2S)-1-hydroxy-1,2-dihydronaphthalen-2-yl]sulfanyl}ethyl]-C-hydroxycarbonimidoyl}butanoic acid
Traditional IUPAC Name:(2S)-2-amino-4-{[(1R)-1-(carboxymethyl-C-hydroxycarbonimidoyl)-2-{[(1S,2S)-1-hydroxy-1,2-dihydronaphthalen-2-yl]sulfanyl}ethyl]-C-hydroxycarbonimidoyl}butanoic acid
SMILES:[H][C@](N)(CCC(O)=N[C@@]([H])(CS[C@@]1([H])C=CC2=CC=CC=C2[C@]1([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
  • Oxacycle
  • Organoheterocyclic compound
  • Ether
  • Oxirane
  • Dialkyl ether
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic 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
Polarizability45.87 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 <> (1S)-Hydroxy-(2S)-glutathionyl-1,2-dihydronaphthalene
Glutathione + Naphthalene epoxide + (1R,2S)-Naphthalene 1,2-oxide > (1S)-Hydroxy-(2S)-glutathionyl-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, Positivesplash10-0002-3914600000-b40c96c8e2523516a20eView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-0v4i-8692067000-e2127d05e92a6967a052View 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 (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 ("(1S)-Hydroxy-(2S)-glutathionyl-1,2-dihydronaphthalene,2TBDMS,#4" TMS) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00e9-2126900000-1b7006b87834305a79f7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-9226100000-d8fd93086d00e09aaedcView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00di-9321000000-9198956786ba979c68f9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0zir-0513900000-b60008cc9c9ba81f90a2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a6r-0910000000-16406d930e33b85c278cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-002f-1900000000-66a973bc3e3243bef84aView 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 ID34000
HMDB IDHMDB0060302
Pubchem Compound ID11954044
Kegg IDC14792
ChemSpider ID10128340
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