1-Nitro-5-glutathionyl-6-hydroxy-5,6-dihydronaphthalene (PAMDB000873)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 11:54:54 AM
Metabolite IDPAMDB000873
Identification
Name: 1-Nitro-5-glutathionyl-6-hydroxy-5,6-dihydronaphthalene
Description:1-nitro-5-glutathionyl-6-hydroxy-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
🔍MOLSDFPDBSMILESInChIView Structure
Synonyms:
  • (2S)-2-amino-5-(2R)-1-(carboxymethylamino)-3-(2-Hydroxy-5-nitro-1,2-dihydronaphthalen-1-yl)sulfanyl-1-oxopropan-2-ylamino-5-oxopentanoate
  • (2S)-2-amino-5-(2R)-1-(carboxymethylamino)-3-(2-hydroxy-5-nitro-1,2-dihydronaphthalen-1-yl)sulfanyl-1-oxopropan-2-ylamino-5-oxopentanoic acid
  • (2S)-2-amino-5-(2R)-1-(carboxymethylamino)-3-(2-Hydroxy-5-nitro-1,2-dihydronaphthalen-1-yl)sulphanyl-1-oxopropan-2-ylamino-5-oxopentanoate
  • (2S)-2-amino-5-(2R)-1-(carboxymethylamino)-3-(2-Hydroxy-5-nitro-1,2-dihydronaphthalen-1-yl)sulphanyl-1-oxopropan-2-ylamino-5-oxopentanoic acid
  • L-g-Glutamyl-S-(2-hydroxy-5-nitro-1,2-dihydro-1-naphthalenyl)-L-cysteinylglycine
  • L-gamma-Glutamyl-S-(2-hydroxy-5-nitro-1,2-dihydro-1-naphthalenyl)-L-cysteinylglycine
  • L-γ-Glutamyl-S-(2-hydroxy-5-nitro-1,2-dihydro-1-naphthalenyl)-L-cysteinylglycine
Chemical Formula: C20H24N4O9S
Average Molecular Weight: 496.491
Monoisotopic Molecular Weight: 496.126399076
InChI Key: ASZHPHJDCUIIBF-RJXQQRCHSA-N
InChI:InChI=1S/C20H24N4O9S/c21-12(20(30)31)5-7-16(26)23-13(19(29)22-8-17(27)28)9-34-18-11-2-1-3-14(24(32)33)10(11)4-6-15(18)25/h1-4,6,12-13,15,18,25H,5,7-9,21H2,(H,22,29)(H,23,26)(H,27,28)(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-[(2-hydroxy-5-nitro-1,2-dihydronaphthalen-1-yl)sulfanyl]ethyl]-C-hydroxycarbonimidoyl}butanoic acid
Traditional IUPAC Name: (2S)-2-amino-4-{[(1R)-1-(carboxymethyl-C-hydroxycarbonimidoyl)-2-[(2-hydroxy-5-nitro-1,2-dihydronaphthalen-1-yl)sulfanyl]ethyl]-C-hydroxycarbonimidoyl}butanoic acid
SMILES:[H][C@](N)(CCC(O)=N[C@@]([H])(CSC1([H])C2=C(C=CC1([H])O)C(=CC=C2)N(=O)=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
  • 1-nitronaphthalene
  • N-acyl-alpha amino acid or derivatives
  • N-acyl-alpha-amino acid
  • D-alpha-amino acid
  • Naphthalene
  • Alpha-amino acid or derivatives
  • Alpha-amino acid
  • Amino fatty acid
  • Fatty acyl
  • Benzenoid
  • Dicarboxylic acid or derivatives
  • Organic nitro compound
  • Secondary alcohol
  • Organic nitrite
  • C-nitro compound
  • Dialkylthioether
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Allyl-type 1,3-dipolar organic compound
  • Sulfenyl compound
  • Thioether
  • Organic oxoazanium
  • Carboxylic acid
  • Carboximidic acid derivative
  • Carboximidic acid
  • Hydrocarbon derivative
  • Organic salt
  • Primary amine
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Carbonyl group
  • Amine
  • Alcohol
  • Organic cation
  • Aromatic homopolycyclic compound
Molecular Framework Aromatic homopolycyclic compounds
External Descriptors Not Available
Physical Properties
State: Not Available
Charge:-2
Melting point: Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility0.0485 mg/mLALOGPS
logP-1.5ALOGPS
logP-1.8ChemAxon
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 Å2ChemAxon
Rotatable Bond Count12ChemAxon
Refractivity121.43 m3·mol-1ChemAxon
Polarizability47.25 Å3ChemAxon
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-glutathionyl-6-hydroxy-5,6-dihydronaphthalene
Pathways: Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0000900000-ff4921fa4db2226179f3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-006t-3000900000-a5bdd09564bea0dcd157View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00di-9210000000-bc0198c4e44217ca1bddView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0000900000-6cac03836a1b55f7d257View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-2110900000-9b223f0ded26f56446d3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-9840000000-193d3a6346b816a51d2dView 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
Synthesis Reference: Not Available
Material Safety Data Sheet (MSDS) Not Available
External Links:
ResourceLink
CHEBI IDNot Available
HMDB IDHMDB60326
Pubchem Compound ID11954057
Kegg IDC14806
ChemSpider ID10128352
Wikipedia IDNot Available
BioCyc IDNot Available

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