3,4-Dihydro-3-hydroxy-4-S-glutathionyl bromobenzene (PAMDB000927)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 12:54:54 PM
Metabolite IDPAMDB000927
Identification
Name: 3,4-Dihydro-3-hydroxy-4-S-glutathionyl bromobenzene
Description:3,4-dihydro-3-hydroxy-4-s-glutathionyl 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
🔍MOLSDFPDBSMILESInChIView Structure
Synonyms:
  • (2S)-2-amino-5-(2R)-3-(4-bromo-6-Hydroxycyclohexa-2,4-dien-1-yl)sulfanyl-1-(carboxymethylamino)-1-oxopropan-2-ylamino-5-oxopentanoate
  • (2S)-2-amino-5-(2R)-3-(4-bromo-6-hydroxycyclohexa-2,4-dien-1-yl)sulfanyl-1-(carboxymethylamino)-1-oxopropan-2-ylamino-5-oxopentanoic acid
  • (2S)-2-amino-5-(2R)-3-(4-bromo-6-Hydroxycyclohexa-2,4-dien-1-yl)sulphanyl-1-(carboxymethylamino)-1-oxopropan-2-ylamino-5-oxopentanoate
  • (2S)-2-amino-5-(2R)-3-(4-bromo-6-Hydroxycyclohexa-2,4-dien-1-yl)sulphanyl-1-(carboxymethylamino)-1-oxopropan-2-ylamino-5-oxopentanoic acid
  • L-g-Glutamyl-S-(4-bromo-6-hydroxy-2,4-cyclohexadien-1-yl)-L-cysteinylglycine
  • L-gamma-Glutamyl-S-(4-bromo-6-hydroxy-2,4-cyclohexadien-1-yl)-L-cysteinylglycine
  • L-γ-Glutamyl-S-(4-bromo-6-hydroxy-2,4-cyclohexadien-1-yl)-L-cysteinylglycine
Chemical Formula: C16H22BrN3O7S
Average Molecular Weight: 480.331
Monoisotopic Molecular Weight: 479.03618341
InChI Key: WIPMNDWTVDZAHE-JYBOHDQNSA-N
InChI:InChI=1S/C16H22BrN3O7S/c17-8-1-3-12(11(21)5-8)28-7-10(15(25)19-6-14(23)24)20-13(22)4-2-9(18)16(26)27/h1,3,5,9-12,21H,2,4,6-7,18H2,(H,19,25)(H,20,22)(H,23,24)(H,26,27)/t9-,10-,11?,12?/m0/s1
CAS number: Not Available
IUPAC Name:(2S)-2-amino-4-{[(1R)-2-[(4-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=CC(Br)=CC1([H])O)C(O)=NCC(O)=O)C(O)=O
Chemical Taxonomy
Taxonomy DescriptionThis compound belongs to the class of organic compounds 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.
Kingdom Organic compounds
Super ClassOrganic acids and derivatives
Class Carboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct Parent Peptides
Alternative Parents
Substituents
  • Alpha peptide
  • N-acyl-aliphatic-alpha amino acid
  • N-acyl-alpha amino acid or derivatives
  • N-acyl-alpha-amino acid
  • D-alpha-amino acid
  • Alpha-amino acid or derivatives
  • Alpha-amino acid
  • Carbocyclic fatty acid
  • Halogenated fatty acid
  • Amino fatty acid
  • Fatty acyl
  • Dicarboxylic acid or derivatives
  • Cyclic alcohol
  • Secondary alcohol
  • Bromoalkene
  • Haloalkene
  • Dialkylthioether
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Sulfenyl compound
  • Vinyl halide
  • Vinyl bromide
  • Thioether
  • Carboxylic acid
  • Carboximidic acid derivative
  • Carboximidic acid
  • Hydrocarbon derivative
  • Primary amine
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organobromide
  • Organohalogen compound
  • Primary aliphatic amine
  • Carbonyl group
  • Amine
  • Alcohol
  • Aliphatic homomonocyclic compound
Molecular Framework Aliphatic homomonocyclic compounds
External Descriptors Not Available
Physical Properties
State: Not Available
Charge:-2
Melting point: Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility0.0888 mg/mLALOGPS
logP-1.8ALOGPS
logP-2.4ChemAxon
logS-3.7ALOGPS
pKa (Strongest Acidic)1.86ChemAxon
pKa (Strongest Basic)9.54ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area186.03 Å2ChemAxon
Rotatable Bond Count11ChemAxon
Refractivity106.82 m3·mol-1ChemAxon
Polarizability42.71 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Cytoplasm
Reactions:
Bromobenzene-3,4-oxide + Glutathione <> 3,4-Dihydro-3-hydroxy-4-S-glutathionyl bromobenzene
Pathways: Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-02ha-2023900000-a99b2d602d251ac08e3bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-9145100000-5e3af90d25319ad465d6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00di-9241000000-6ee8399683c139ed4a2cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0h00-0231900000-5c894a3884a1afaf36ffView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0f79-0971100000-009d5316a5746058cd36View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0udl-1920000000-d4ea4fbd0aa6eae7ab02View in MoNA
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
  • Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
Synthesis Reference: Not Available
Material Safety Data Sheet (MSDS) Not Available
External Links:
ResourceLink
CHEBI IDNot Available
HMDB IDHMDB60381
Pubchem Compound ID11954066
Kegg IDC14847
ChemSpider ID10128361
Wikipedia IDNot Available
BioCyc IDDIHYDRO-DIOH-BENZOATE
EcoCyc IDDIHYDRO-DIOH-BENZOATE

Enzymes

Protein Details
• GSH-dependent disulfide bond oxidoreductase
General function:
Not Available
Specific function:
Not Available
Gene Name:
yfcG
Locus Tag:
PA1033
Molecular weight:
24.5 kDa