2,3-Dihydro-2-S-glutathionyl-3-hydroxy bromobenzene (ECMDB20055) (M2MDB000904)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes (2)XML
Proteins (887)
Record Information
Version2.0
Creation Date2012-05-31 14:25:06 -0600
Update Date2015-06-03 17:19:13 -0600
Secondary Accession Numbers
  • ECMDB20055
Identification
Name:2,3-Dihydro-2-S-glutathionyl-3-hydroxy bromobenzene
Description2,3-dihydro-2-s-glutathionyl-3-hydroxy 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
MOLSDFPDBSMILESInChI
Synonyms:
  • (2S)-2-amino-5-(2R)-3-(2-bromo-6-Hydroxycyclohexa-2,4-dien-1-yl)sulfanyl-1-(carboxymethylamino)-1-oxopropan-2-ylamino-5-oxopentanoate
  • (2S)-2-amino-5-(2R)-3-(2-bromo-6-hydroxycyclohexa-2,4-dien-1-yl)sulfanyl-1-(carboxymethylamino)-1-oxopropan-2-ylamino-5-oxopentanoic acid
  • (2S)-2-amino-5-(2R)-3-(2-bromo-6-Hydroxycyclohexa-2,4-dien-1-yl)sulphanyl-1-(carboxymethylamino)-1-oxopropan-2-ylamino-5-oxopentanoate
  • (2S)-2-amino-5-(2R)-3-(2-bromo-6-Hydroxycyclohexa-2,4-dien-1-yl)sulphanyl-1-(carboxymethylamino)-1-oxopropan-2-ylamino-5-oxopentanoic acid
  • L-g-Glutamyl-S-(2-bromo-6-hydroxy-2,4-cyclohexadien-1-yl)-L-cysteinylglycine
  • L-gamma-Glutamyl-S-(2-bromo-6-hydroxy-2,4-cyclohexadien-1-yl)-L-cysteinylglycine
  • L-γ-Glutamyl-S-(2-bromo-6-hydroxy-2,4-cyclohexadien-1-yl)-L-cysteinylglycine
Chemical Formula:C16H22BrN3O7S
Weight:Average: 480.331
Monoisotopic: 479.03618341
InChI Key:BYHFLDCNLZPMDY-PXAOEZFJSA-N
InChI:InChI=1S/C16H22BrN3O7S/c17-8-2-1-3-11(21)14(8)28-7-10(15(25)19-6-13(23)24)20-12(22)5-4-9(18)16(26)27/h1-3,9-11,14,21H,4-7,18H2,(H,19,25)(H,20,22)(H,23,24)(H,26,27)/t9-,10-,11?,14?/m0/s1
CAS number:Not Available
IUPAC Name:(2S)-2-amino-4-{[(1R)-2-[(2-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(Br)=CC=CC1([H])O)C(O)=NCC(O)=O)C(O)=O
Chemical Taxonomy
Description belongs to the class of organic compounds known as menaquinones. These are vitamin K2 compounds consisting of a naphtho-1,4-quinone ring system, which is substituted at the 2-position by an isoprenyl side-chain, and usually, at the 3-position by a methyl group.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassQuinone and hydroquinone lipids
Direct ParentMenaquinones
Alternative Parents
Substituents
  • Menaquinone
  • Naphthoquinone
  • Aromatic monoterpenoid
  • Monoterpenoid
  • Naphthalene
  • Tetralin
  • Quinone
  • Aryl alkyl ketone
  • Aryl ketone
  • Benzenoid
  • Ketone
  • Oxacycle
  • Ether
  • Oxirane
  • Dialkyl ether
  • Organoheterocyclic compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Physical Properties
State:Not Available
Charge:-2
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility0.093 g/LALOGPS
logP-1.6ALOGPS
logP-2.7ChemAxon
logS-3.7ALOGPS
pKa (Strongest Acidic)1.85ChemAxon
pKa (Strongest Basic)9.54ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area186.03 ŲChemAxon
Rotatable Bond Count11ChemAxon
Refractivity106.88 m³·mol⁻¹ChemAxon
Polarizability42.66 ųChemAxon
Number of Rings1ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
Bromobenzene-2,3-oxide + Glutathione <> 2,3-Dihydro-2-S-glutathionyl-3-hydroxy bromobenzene
Glutathione + Bromobenzene-2,3-oxide > 2,3-Dihydro-2-S-glutathionyl-3-hydroxy bromobenzene
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, Positivesplash10-0a6u-8223900000-d28e12c2023be0fbd107View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-001i-9520118000-e81e6ce8574f79868137View 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_10) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS ("2,3-Dihydro-2-S-glutathionyl-3-hydroxy bromobenzene,2TBDMS,#4" TMS) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03l1-2034900000-9e29c053a3102e782c94View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00dj-9147200000-79f78291fcb10f200d89View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05fr-9351000000-2a2fe7b7a1d505d34b59View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0h09-0242900000-1a5c1f15dc7cd74cf7fbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0f79-0891100000-36f60450b17e84105291View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0ufv-1930000000-47ff8d9d52ecd62eb9a5View 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 ID34228
HMDB IDHMDB0060358
Pubchem Compound ID11954067
Kegg IDC14848
ChemSpider ID10128362
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