P. aeruginosa Metabolome Database: 2,4-dinitrophenyl-S-glutathione (PAMDB120184)

Identification Taxonomy Physical Properties Biological Properties Spectra Concentrations Links References Enzymes Transporters

Proteins (3280)

Record Information

Version

1.0

Update Date

1/22/2018 11:54:54 AM

Metabolite ID

PAMDB120184

Identification

Name:

2,4-dinitrophenyl-S-glutathione

Description:

A Glu-Cys-Gly tripeptide glutathione conjugate containing a 2,4-dinitrophenyl substituent on the S of Cys.

Structure

🔍MOL SDF PDB SMILES InChI View Structure

Synonyms:

dinitrophenyl-S-glutathione
DNP-S-glutathione
S-(2,4-Dinitrophenyl)glutathione

Chemical Formula:

C₁₆H₁₈N₅O₁₀S

Average Molecular Weight:

472.406

Monoisotopic Molecular Weight:

476.10873

InChI Key:

FXEUKVKGTKDDIQ-UWVGGRQHSA-M

InChI:

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)/p-1/t9-,10-/m0/s1

CAS number:

Not Available

IUPAC Name:

L-γ-glutamyl-S-(2,4-dinitrophenyl)-L-cysteinylglycine

Traditional IUPAC Name:

Not Available

SMILES:

C(=O)([O-])CNC(=O)C(NC(=O)CCC([N+])C(=O)[O-])CSC1(C=CC([N+]([O-])=O)=CC([N+]([O-])=O)=1)

Chemical Taxonomy

Taxonomy Description

This compound 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.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Oligopeptides

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
N-substituted-alpha-amino acid
Alpha-amino acid or derivatives
Nitrobenzene
Aryl thioether
Nitroaromatic compound
Thiophenol ether
Alkylarylthioether
Benzenoid
N-acyl-amine
Fatty acyl
Fatty amide
Dicarboxylic acid or derivatives
Monocyclic benzene moiety
Carboxamide group
Carboxylic acid salt
Organic nitro compound
C-nitro compound
Secondary carboxylic acid amide
Thioether
Sulfenyl compound
Carboxylic acid
Organic oxoazanium
Organic salt
Organopnictogen compound
Hydrocarbon derivative
Organic oxygen compound
Organic nitrogen compound
Carbonyl group
Organic oxide
Organonitrogen compound
Organooxygen compound
Organosulfur compound
Organic anion
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Physical Properties

State:

Not Available

Charge:

Melting point:

Not Available

Experimental Properties:

Not Available

Predicted Properties

Property	Value	Source
Molecular Weight	472.405 g/mol	PubChem
XLogP3-AA	-1.6	PubChem
Hydrogen Bond Donor Count	3	PubChem
Hydrogen Bond Acceptor Count	11	PubChem
Rotatable Bond Count	9	PubChem
Exact Mass	472.077 g/mol	PubChem
Monoisotopic Mass	472.077 g/mol	PubChem
Topological Polar Surface Area	283 A^2	PubChem
Heavy Atom Count	32	PubChem
Formal Charge	-1	PubChem
Complexity	729	PubChem
Isotope Atom Count	0	PubChem
Defined Atom Stereocenter Count	2	PubChem
Undefined Atom Stereocenter Count	0	PubChem
Defined Bond Stereocenter Count	0	PubChem
Undefined Bond Stereocenter Count	0	PubChem
Covalently-Bonded Unit Count	1	PubChem

Biological Properties

Cellular Locations:

Not Available

Reactions:

1-chloro-2,4-dinitrobenzene + glutathione → Hydrogen ion + 2,4-dinitrophenyl-S-glutathione + Chloride

Pathways:

Spectra

Spectra:

Not Available

References

References:

Awasthi S, Ahmad F, Sharma R, Ahmad H (1992)Reversed-phase chromatographic method for specific determination of glutathione in cultured malignant cells. Journal of chromatography 584, Pubmed: 1484101
Arias A, Villanueva SS, Ruiz ML, Luquita MG, Veggi LM, Pellegrino JM, Vore M, Catania VA, Mottino AD (2009)Regulation of expression and activity of rat intestinal multidrug resistance-associated protein 2 by cholestatic estrogens. Drug metabolism and disposition: the biological fate of chemicals 37, Pubmed: 19299525
Diah SK, Smitherman PK, Townsend AJ, Morrow CS (1999)Detoxification of 1-chloro-2,4-dinitrobenzene in MCF7 breast cancer cells expressing glutathione S-transferase P1-1 and/or multidrug resistance protein 1. Toxicology and applied pharmacology 157, Pubmed: 10366541
Villanueva SS, Perdomo VG, Ruiz ML, Rigalli JP, Arias A, Luquita MG, Vore M, Catania VA, Mottino AD (2012)Effect of glucagon-like peptide 2 on hepatic, renal, and intestinal disposition of 1-chloro-2,4-dinitrobenzene. Drug metabolism and disposition: the biological fate of chemicals 40, Pubmed: 22453052
Wawrzycka D, Sobczak I, Bartosz G, Bocer T, Ulaszewski S, Goffeau A (2010)Vmr 1p is a novel vacuolar multidrug resistance ABC transporter in Saccharomyces cerevisiae. FEMS yeast research 10, Pubmed: 20846144
Villanueva SS, Arias A, Ruiz ML, Rigalli JP, Pellegrino JM, Vore M, Catania VA, Mottino AD (2010)Induction of intestinal multidrug resistance-associated protein 2 by glucagon-like Peptide 2 in the rat. The Journal of pharmacology and experimental therapeutics 335, Pubmed: 20719938
Rigalli JP, Perdomo VG, Luquita MG, Villanueva SS, Arias A, Theile D, Weiss J, Mottino AD, Ruiz ML, Catania VA (2012)Regulation of biotransformation systems and ABC transporters by benznidazole in HepG2 cells: involvement of pregnane X-receptor. PLoS neglected tropical diseases 6, Pubmed: 23272261
Jin S, Wang XT, Liu L, Yao D, Liu C, Zhang M, Guo HF, Liu XD (2013)P-glycoprotein and multidrug resistance-associated protein 2 are oppositely altered in brain of rats with thioacetamide-induced acute liver failure. Liver international : official journal of the International Association for the Study of the Liver 33, Pubmed: 22925079
Coleman JW, Yeung JH, Tingle MD, Park BK (1986)Enzyme-linked immunosorbent assay (ELISA) for detection of antibodies to protein-reactive drugs and metabolites: criteria for identification of antibody activity. Detection and hapten specificity of anti-DNP, anti-captopril and anti-sulphanilamidobenzoic acid. Journal of immunological methods 88, Pubmed: 2420897
Pulaski L, Bartosz G (1995)Effect of inhibitors on the transport of dinitrophenyl-S-glutathione in human erythrocytes. Biochemistry and molecular biology international 36, Pubmed: 7581009

Synthesis Reference:

Not Available

Material Safety Data Sheet (MSDS)

Not Available

Links

External Links:

Resource	Link
PUBCHEM	25322932
CHEBI	8927
LIGAND-CPD	C11175

2,4-dinitrophenyl-S-glutathione (PAMDB120184)

Structure for 2,4-dinitrophenyl-S-glutathione (PAMDB120184)