(1R)-Glutathionyl-(2R)-hydroxy-1,2-dihydronaphthalene (PAMDB000852)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 12:54:54 PM
Metabolite IDPAMDB000852
Identification
Name: (1R)-Glutathionyl-(2R)-hydroxy-1,2-dihydronaphthalene
Description:(1r)-glutathionyl-(2r)-hydroxy-1,2-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
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🔍MOLSDFPDBSMILESInChIView Structure
Synonyms:
  • (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
  • (2S)-2-amino-5-(2R)-1-(carboxymethylamino)-3-(1R,2R)-2-Hydroxy-1,2-dihydronaphthalen-1-ylsulfanyl-1-oxopropan-2-ylamino-5-oxopentanoate
  • (2S)-2-amino-5-(2R)-1-(carboxymethylamino)-3-(1R,2R)-2-hydroxy-1,2-dihydronaphthalen-1-ylsulfanyl-1-oxopropan-2-ylamino-5-oxopentanoic acid
  • (2S)-2-amino-5-(2R)-1-(carboxymethylamino)-3-(1R,2R)-2-Hydroxy-1,2-dihydronaphthalen-1-ylsulphanyl-1-oxopropan-2-ylamino-5-oxopentanoate
  • (2S)-2-amino-5-(2R)-1-(carboxymethylamino)-3-(1R,2R)-2-Hydroxy-1,2-dihydronaphthalen-1-ylsulphanyl-1-oxopropan-2-ylamino-5-oxopentanoic acid
  • 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
  • L-g-Glutamyl-S-(1R,2R)-2-hydroxy-1,2-dihydro-1-naphthalenyl-L-cysteinylglycine
  • L-gamma-Glutamyl-S-(1R,2R)-2-hydroxy-1,2-dihydro-1-naphthalenyl-L-cysteinylglycine
  • L-γ-Glutamyl-S-(1R,2R)-2-hydroxy-1,2-dihydro-1-naphthalenyl-L-cysteinylglycine
Chemical Formula: C20H25N3O7S
Average Molecular Weight: 451.493
Monoisotopic Molecular Weight: 451.141320859
InChI Key: UWBZAZWPTVBBEL-OIPACUDHSA-N
InChI:InChI=1S/C20H25N3O7S/c21-13(20(29)30)6-8-16(25)23-14(19(28)22-9-17(26)27)10-31-18-12-4-2-1-3-11(12)5-7-15(18)24/h1-5,7,13-15,18,24H,6,8-10,21H2,(H,22,28)(H,23,25)(H,26,27)(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-{[(1R,2R)-2-hydroxy-1,2-dihydronaphthalen-1-yl]sulfanyl}ethyl]-C-hydroxycarbonimidoyl}butanoic acid
Traditional IUPAC Name: (2S)-2-amino-4-{[(1R)-1-(carboxymethyl-C-hydroxycarbonimidoyl)-2-{[(1R,2R)-2-hydroxy-1,2-dihydronaphthalen-1-yl]sulfanyl}ethyl]-C-hydroxycarbonimidoyl}butanoic acid
SMILES:[H][C@](N)(CCC(O)=N[C@@]([H])(CS[C@]1([H])C2=CC=CC=C2C=C[C@@]1([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
  • Naphthalene
  • Alpha-amino acid or derivatives
  • Alpha-amino acid
  • Amino fatty acid
  • Fatty acyl
  • Benzenoid
  • Dicarboxylic acid or derivatives
  • Secondary alcohol
  • Dialkylthioether
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Sulfenyl compound
  • Thioether
  • Carboxylic acid
  • Carboximidic acid derivative
  • Carboximidic acid
  • Hydrocarbon derivative
  • Primary amine
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Carbonyl group
  • Amine
  • Alcohol
  • 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 Solubility0.0581 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count11ChemAxon
Refractivity114.1 m3·mol-1ChemAxon
Polarizability45 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Cytoplasm
Reactions:
Naphthalene epoxide + Glutathione + (1R,2S)-Naphthalene 1,2-oxide > (1R)-Glutathionyl-(2R)-hydroxy-1,2-dihydronaphthalene
Pathways:
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00e9-3126900000-e852fce9919b502e2de0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-9226100000-8ad87012ef3d3e1f9b0bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00di-9221000000-4da054dda6edae051eb7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0zir-0513900000-99965a9d9f77c397a0b8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a6r-0910000000-b0f870f10a0d4c614ccfView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-002f-1900000000-e7b810e5d1d7c3d02dd0View 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 IDHMDB60299
Pubchem Compound ID11954046
Kegg IDC14793
ChemSpider ID10128341
Wikipedia IDNot Available
BioCyc IDCIS-12-DIHYDRONAPHTHALENE-12-DIOL
EcoCyc IDCIS-12-DIHYDRONAPHTHALENE-12-DIOL

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