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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2017-03-23 03:11:20 UTC
Update Date2021-09-14 15:41:40 UTC
HMDB IDHMDB0062528
Secondary Accession Numbers
  • HMDB62528
Metabolite Identification
Common Name1-(s-glutathionyl)-2,4-dinitrobenzene
Description1-(s-glutathionyl)-2,4-dinitrobenzene, also known as dinitrophenyl-S-glutathione or DNP-SG, belongs to the class of organic compounds known as oligopeptides. These are organic compounds containing a sequence of between three and ten alpha-amino acids joined by peptide bonds. 1-(s-glutathionyl)-2,4-dinitrobenzene is a very strong basic compound (based on its pKa). A glutathione conjugate in which the thiol hydrogen of glutathione has been replaced by a 2,4-dinitrophenyl group.
Structure
Data?1563866324
Synonyms
ValueSource
Dinitrophenyl-S-glutathioneChEBI
DNP-S-GlutathioneChEBI
DNP-SGChEBI
GS-DNPHMDB
GSH-S-DNPHMDB
Chemical FormulaC16H19N5O10S
Average Molecular Weight473.415
Monoisotopic Molecular Weight473.085262543
IUPAC Name(2S)-2-amino-4-{[(1R)-1-[(carboxymethyl)carbamoyl]-2-[(2,4-dinitrophenyl)sulfanyl]ethyl]carbamoyl}butanoic acid
Traditional Namedinitrophenyl-S-glutathione
CAS Registry Number26289-39-4
SMILES
[H][C@](N)(CCC(=O)N[C@@]([H])(CSC1=C(C=C(C=C1)N(=O)=O)N(=O)=O)C(=O)NCC(O)=O)C(O)=O
InChI Identifier
InChI=1S/C16H19N5O10S/c17-9(16(26)27)2-4-13(22)19-10(15(25)18-6-14(23)24)7-32-12-3-1-8(20(28)29)5-11(12)21(30)31/h1,3,5,9-10H,2,4,6-7,17H2,(H,18,25)(H,19,22)(H,23,24)(H,26,27)/t9-,10-/m0/s1
InChI KeyFXEUKVKGTKDDIQ-UWVGGRQHSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as oligopeptides. These are organic compounds containing a sequence of between three and ten alpha-amino acids joined by peptide bonds.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentOligopeptides
Alternative Parents
Substituents
  • Alpha-oligopeptide
  • Gamma-glutamyl alpha peptide
  • Glutamine or derivatives
  • N-acyl-alpha amino acid or derivatives
  • N-acyl-alpha-amino acid
  • Alpha-amino acid amide
  • Cysteine or derivatives
  • Alpha-amino acid
  • N-substituted-alpha-amino acid
  • Alpha-amino acid or derivatives
  • L-alpha-amino acid
  • Nitrobenzene
  • Aryl thioether
  • Nitroaromatic compound
  • Thiophenol ether
  • Alkylarylthioether
  • N-acyl-amine
  • Fatty acyl
  • Benzenoid
  • Fatty amide
  • Dicarboxylic acid or derivatives
  • Monocyclic benzene moiety
  • Amino acid or derivatives
  • Amino acid
  • Carboxamide group
  • Organic nitro compound
  • C-nitro compound
  • Secondary carboxylic acid amide
  • Thioether
  • Carboxylic acid
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Allyl-type 1,3-dipolar organic compound
  • Sulfenyl compound
  • Organic oxoazanium
  • Primary amine
  • Organic oxide
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Organopnictogen compound
  • Carbonyl group
  • Organic oxygen compound
  • Primary aliphatic amine
  • Organosulfur compound
  • Organooxygen compound
  • Organic zwitterion
  • Amine
  • Organonitrogen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Role

Industrial application:

Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.032 g/lALOGPS
LogP-1.33ALOGPS
Predicted Molecular Properties
PropertyValueSource
logP-1.3ALOGPS
logP-3.3ChemAxon
logS-4.2ALOGPS
pKa (Strongest Acidic)1.6ChemAxon
pKa (Strongest Basic)9.31ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count11ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area250.46 ŲChemAxon
Rotatable Bond Count13ChemAxon
Refractivity108.34 m³·mol⁻¹ChemAxon
Polarizability42.88 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Spectral Properties

Collision Cross Sections

NameAdductTypeData SourceValueReference
DarkChem[M+H]+PredictedNot Available207.20731661259
DarkChem[M-H]-PredictedNot Available197.15331661259

Retention Indices

Underivatized

Not Available

Derivatized

DerivativeValueReference
1-(s-glutathionyl)-2,4-dinitrobenzene,1TMS,#14040.0068https://arxiv.org/abs/1905.12712
1-(s-glutathionyl)-2,4-dinitrobenzene,1TMS,#24011.8555https://arxiv.org/abs/1905.12712
1-(s-glutathionyl)-2,4-dinitrobenzene,1TMS,#34135.4155https://arxiv.org/abs/1905.12712
1-(s-glutathionyl)-2,4-dinitrobenzene,1TMS,#44029.4229https://arxiv.org/abs/1905.12712
1-(s-glutathionyl)-2,4-dinitrobenzene,1TMS,#54069.3193https://arxiv.org/abs/1905.12712
1-(s-glutathionyl)-2,4-dinitrobenzene,2TMS,#13940.013https://arxiv.org/abs/1905.12712
1-(s-glutathionyl)-2,4-dinitrobenzene,2TMS,#24033.675https://arxiv.org/abs/1905.12712
1-(s-glutathionyl)-2,4-dinitrobenzene,2TMS,#33941.9126https://arxiv.org/abs/1905.12712
1-(s-glutathionyl)-2,4-dinitrobenzene,2TMS,#43908.238https://arxiv.org/abs/1905.12712
1-(s-glutathionyl)-2,4-dinitrobenzene,2TMS,#54006.833https://arxiv.org/abs/1905.12712
1-(s-glutathionyl)-2,4-dinitrobenzene,2TMS,#63908.5117https://arxiv.org/abs/1905.12712
1-(s-glutathionyl)-2,4-dinitrobenzene,2TMS,#73939.156https://arxiv.org/abs/1905.12712
1-(s-glutathionyl)-2,4-dinitrobenzene,2TMS,#84133.2656https://arxiv.org/abs/1905.12712
1-(s-glutathionyl)-2,4-dinitrobenzene,2TMS,#94032.3137https://arxiv.org/abs/1905.12712
1-(s-glutathionyl)-2,4-dinitrobenzene,2TMS,#104051.1604https://arxiv.org/abs/1905.12712
1-(s-glutathionyl)-2,4-dinitrobenzene,2TMS,#113918.223https://arxiv.org/abs/1905.12712
1-(s-glutathionyl)-2,4-dinitrobenzene,1TBDMS,#14332.493https://arxiv.org/abs/1905.12712
1-(s-glutathionyl)-2,4-dinitrobenzene,1TBDMS,#24317.5957https://arxiv.org/abs/1905.12712
1-(s-glutathionyl)-2,4-dinitrobenzene,1TBDMS,#34363.9746https://arxiv.org/abs/1905.12712
1-(s-glutathionyl)-2,4-dinitrobenzene,1TBDMS,#44314.715https://arxiv.org/abs/1905.12712
1-(s-glutathionyl)-2,4-dinitrobenzene,1TBDMS,#54366.7656https://arxiv.org/abs/1905.12712
1-(s-glutathionyl)-2,4-dinitrobenzene,2TBDMS,#14480.101https://arxiv.org/abs/1905.12712
1-(s-glutathionyl)-2,4-dinitrobenzene,2TBDMS,#24523.155https://arxiv.org/abs/1905.12712
1-(s-glutathionyl)-2,4-dinitrobenzene,2TBDMS,#34479.3657https://arxiv.org/abs/1905.12712
1-(s-glutathionyl)-2,4-dinitrobenzene,2TBDMS,#44463.952https://arxiv.org/abs/1905.12712
1-(s-glutathionyl)-2,4-dinitrobenzene,2TBDMS,#54483.2397https://arxiv.org/abs/1905.12712
1-(s-glutathionyl)-2,4-dinitrobenzene,2TBDMS,#64456.6855https://arxiv.org/abs/1905.12712
1-(s-glutathionyl)-2,4-dinitrobenzene,2TBDMS,#74476.5874https://arxiv.org/abs/1905.12712
1-(s-glutathionyl)-2,4-dinitrobenzene,2TBDMS,#84649.4473https://arxiv.org/abs/1905.12712
1-(s-glutathionyl)-2,4-dinitrobenzene,2TBDMS,#94525.6597https://arxiv.org/abs/1905.12712
1-(s-glutathionyl)-2,4-dinitrobenzene,2TBDMS,#104529.665https://arxiv.org/abs/1905.12712
1-(s-glutathionyl)-2,4-dinitrobenzene,2TBDMS,#114458.6436https://arxiv.org/abs/1905.12712
Spectra

GC-MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-054p-8107900000-0997ff1ef27c83468a352017-09-20View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-0ul0-9304755000-dc63aa4d7521bed152702017-10-06View Spectrum

LC-MS/MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0000900000-9798e0cce053514d13c02017-07-25View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05fr-1000900000-a0acf668b00c07143cd12017-07-25View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0kmi-9411100000-512900eb343275af3abc2017-07-25View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0000900000-888d442055351d4aa3f12017-07-26View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-1310900000-bed8152874bb4bc24f582017-07-26View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05dj-7920000000-9c06c595666075bdb9772017-07-26View Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB02458
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC11175
BioCyc IDS-24-DINITROPHENYLGLUTATHIONE
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound97535
PDB IDGDN
ChEBI ID8927
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available