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89395-03-9 | (2R)-2-AMINO-3-[(Z)-1,2-DICHLOROVINYL]SULFANYL-PROPANOIC ACID
CAS No: 89395-03-9 Catalog No: AG003WJQ MDL No:
Product Description
Catalog Number:
AG003WJQ
Chemical Name:
(2R)-2-AMINO-3-[(Z)-1,2-DICHLOROVINYL]SULFANYL-PROPANOIC ACID
CAS Number:
89395-03-9
Molecular Formula:
C5H7Cl2NO2S
Molecular Weight:
216.0856
IUPAC Name:
(2R)-2-amino-3-(1,2-dichloroethenylsulfanyl)propanoic acid
InChI:
InChI=1S/C5H7Cl2NO2S/c6-1-4(7)11-2-3(8)5(9)10/h1,3H,2,8H2,(H,9,10)/t3-/m0/s1
InChI Key:
PJIHCWJOTSJIPQ-VKHMYHEASA-N
SMILES:
N[C@H](C(=O)O)CS/C(=C/Cl)/Cl
Properties
Complexity:
174
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1
Defined Atom Stereocenter Count:
1
Defined Bond Stereocenter Count:
0
Exact Mass:
214.957g/mol
Formal Charge:
0
Heavy Atom Count:
11
Hydrogen Bond Acceptor Count:
4
Hydrogen Bond Donor Count:
2
Isotope Atom Count:
0
Molecular Weight:
216.076g/mol
Monoisotopic Mass:
214.957g/mol
Rotatable Bond Count:
4
Topological Polar Surface Area:
88.6A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
1
XLogP3:
-1.1
Literature
| Title | Journal |
|---|---|
| Role of reactive metabolites in the circulation in extrahepatic toxicity. | Expert opinion on drug metabolism & toxicology 20120901 |
| Nephrotoxic effect of subchronic exposure to S-(1,2-dichlorovinyl)-L-cysteine in mice. | The Journal of toxicological sciences 20120101 |
| N-biotinyl-S-(1,2-dichlorovinyl)-L-cysteine sulfoxide as a potential model for S-(1,2-dichlorovinyl)-L-cysteine sulfoxide: characterization of stability and reactivity with glutathione and kidney proteins in vitro. | Chemical research in toxicology 20111121 |
| Putting bioactivation reactions to work: Targeting antioxidants to mitochondria. | Chemico-biological interactions 20110630 |
| Altered Hippo signalling in polycystic kidney disease. | The Journal of pathology 20110501 |
| Evaluating pharmacokinetic and pharmacodynamic interactions with computational models in supporting cumulative risk assessment. | International journal of environmental research and public health 20110501 |
| Transport of N-acetyl-S-(1,2-dichlorovinyl)-L-cysteine, a metabolite of trichloroethylene, by mouse multidrug resistance associated protein 2 (Mrp2). | Toxicology and applied pharmacology 20100415 |
| Bone marrow depletion with haemorrhagic diathesis in calves in Germany: characterization of the disease and preliminary investigations on its aetiology. | Berliner und Munchener tierarztliche Wochenschrift 20100101 |
| Globin monoadducts and cross-links provide evidence for the presence of S-(1,2-dichlorovinyl)-L-cysteine sulfoxide, chlorothioketene, and 2-chlorothionoacetyl chloride in the circulation in rats administered S-(1,2-dichlorovinyl)-L-cysteine. | Chemical research in toxicology 20090901 |
| Liquid chromatography electrospray ionization tandem mass spectrometry analysis method for simultaneous detection of trichloroacetic acid, dichloroacetic acid, S-(1,2-dichlorovinyl)glutathione and S-(1,2-dichlorovinyl)-L-cysteine. | Toxicology 20090821 |
| Pharmacokinetic analysis of trichloroethylene metabolism in male B6C3F1 mice: Formation and disposition of trichloroacetic acid, dichloroacetic acid, S-(1,2-dichlorovinyl)glutathione and S-(1,2-dichlorovinyl)-L-cysteine. | Toxicology and applied pharmacology 20090701 |
| Cysteine conjugate beta-lyase activity of rat erythrocytes and formation of beta-lyase-derived globin monoadducts and cross-links after in vitro exposure of erythrocytes to S-(1,2-dichlorovinyl)-L-cysteine. | Chemical research in toxicology 20090701 |
| Reduction in rat oocyte fertilizability mediated by S-(1, 2-dichlorovinyl)-L-cysteine: a trichloroethylene metabolite produced by the glutathione conjugation pathway. | Bulletin of environmental contamination and toxicology 20081101 |
| Detection of multiple globin monoadducts and cross-links after in vitro exposure of rat erythrocytes to S-(1,2-dichlorovinyl)-L-cysteine sulfoxide and after in vivo treatment of rats with S-(1,2-dichlorovinyl)-L-cysteine sulfoxide. | Chemical research in toxicology 20080901 |
| Role of mitochondrial dysfunction in cellular responses to S-(1,2-dichlorovinyl)-L-cysteine in primary cultures of human proximal tubular cells. | Biochemical pharmacology 20080815 |
| Akt activation improves oxidative phosphorylation in renal proximal tubular cells following nephrotoxicant injury. | American journal of physiology. Renal physiology 20080201 |
| Assessment of the genotoxicity of trichloroethylene and its metabolite, S-(1,2-dichlorovinyl)-L-cysteine (DCVC), in the comet assay in rat kidney. | Mutagenesis 20080101 |
| Piecewise multivariate modelling of sequential metabolic profiling data. | BMC bioinformatics 20080101 |
| N-acetyltransferase 8, a positional candidate for blood pressure and renal regulation: resequencing, association and in silico study. | BMC medical genetics 20080101 |
| Proteomics of S-(1, 2-dichlorovinyl)-L-cysteine-induced acute renal failure and autoprotection in mice. | American journal of physiology. Renal physiology 20071001 |
| Formation of three N-acetyl-L-cysteine monoadducts and one diadduct by the reaction of S-(1,2-dichlorovinyl)-L-cysteine sulfoxide with N-acetyl-L-cysteine at physiological conditions: chemical mechanisms and toxicological implications. | Chemical research in toxicology 20071001 |
| Proteomic analysis of alternative protein tyrosine phosphorylation in 1,2-dichlorovinyl-cysteine-induced cytotoxicity in primary cultured rat renal proximal tubular cells. | The Journal of pharmacology and experimental therapeutics 20070701 |
| Interactive toxicity of inorganic mercury and trichloroethylene in rat and human proximal tubules: effects on apoptosis, necrosis, and glutathione status. | Toxicology and applied pharmacology 20070615 |
| Cell adhesion molecules in chemically-induced renal injury. | Pharmacology & therapeutics 20070401 |
| Protein kinase B/Akt modulates nephrotoxicant-induced necrosis in renal cells. | American journal of physiology. Renal physiology 20070101 |
| Changes in gene expression in human renal proximal tubule cells exposed to low concentrations of S-(1,2-dichlorovinyl)-l-cysteine, a metabolite of trichloroethylene. | Toxicology and applied pharmacology 20061015 |
| Key issues in the modes of action and effects of trichloroethylene metabolites for liver and kidney tumorigenesis. | Environmental health perspectives 20060901 |
| Preplaced cell division: a critical mechanism of autoprotection against S-1,2-dichlorovinyl-L-cysteine-induced acute renal failure and death in mice. | American journal of physiology. Renal physiology 20060801 |
| Analysis of renal cell transformation following exposure to trichloroethene in vivo and its metabolite S-(dichlorovinyl)-L-cysteine in vitro. | Toxicology 20060705 |
| Metabolism and tissue distribution of orally administered trichloroethylene in male and female rats: identification of glutathione- and cytochrome P-450-derived metabolites in liver, kidney, blood, and urine. | Journal of toxicology and environmental health. Part A 20060701 |
| Colchicine antimitosis causes progression of S-(1,2-dichlorovinyl)-L-cysteine-induced injury leading to acute renal failure and death in mice. | Toxicology 20060315 |
| Diabetic mice are protected from normally lethal nephrotoxicity of S-1,2-dichlorovinyl-L-cysteine (DCVC): role of nephrogenic tissue repair. | Toxicology and applied pharmacology 20060301 |
| Modulation of expression of rat mitochondrial 2-oxoglutarate carrier in NRK-52E cells alters mitochondrial transport and accumulation of glutathione and susceptibility to chemically induced apoptosis. | The Journal of pharmacology and experimental therapeutics 20060301 |
| Heat shock protein 27 is the major differentially phosphorylated protein involved in renal epithelial cellular stress response and controls focal adhesion organization and apoptosis. | The Journal of biological chemistry 20050819 |
| Role of cell adhesion signal molecules in hepatocellular carcinoma cell apoptosis. | World journal of gastroenterology 20050814 |
| Molecular markers of trichloroethylene-induced toxicity in human kidney cells. | Toxicology and applied pharmacology 20050807 |
| Molecular mechanisms of enhanced renal cell division in protection against S-1,2-dichlorovinyl-L-cysteine-induced acute renal failure and death. | American journal of physiology. Renal physiology 20050701 |
| Protein kinase C-alpha inhibits the repair of oxidative phosphorylation after S-(1,2-dichlorovinyl)-L-cysteine injury in renal cells. | American journal of physiology. Renal physiology 20040701 |
| L-alanine-glyoxylate aminotransferase II of rat kidney and liver mitochondria possesses cysteine S-conjugate beta-lyase activity: a contributing factor to the nephrotoxicity/hepatotoxicity of halogenated alkenes? | The Biochemical journal 20031115 |
| Cytotoxicity of S-conjugates of the sevoflurane degradation product fluoromethyl-2,2-difluoro-1-(trifluoromethyl) vinyl ether (Compound A) in a human proximal tubular cell line. | Toxicology and applied pharmacology 20031115 |
| Evidence for trichloroethylene bioactivation and adduct formation in the rat epididymis and efferent ducts. | Biology of reproduction 20030901 |
| Protein kinase C mediates repair of mitochondrial and transport functions after toxicant-induced injury in renal cells. | The Journal of pharmacology and experimental therapeutics 20030701 |
| Renal cysteine conjugate C-S lyase mediated toxicity of halogenated alkenes in primary cultures of human and rat proximal tubular cells. | Archives of toxicology 20030701 |
| Role of tissue repair in survival from s-(1,2-dichlorovinyl)-L-cysteine-induced acute renal tubular necrosis in the mouse. | Toxicological sciences : an official journal of the Society of Toxicology 20030701 |
| Roles of necrosis, Apoptosis, and mitochondrial dysfunction in S-(1,2-dichlorovinyl)-L-cysteine sulfoxide-induced cytotoxicity in primary cultures of human renal proximal tubular cells. | The Journal of pharmacology and experimental therapeutics 20030601 |
| Renal injury and repair following S-1, 2 dichlorovinyl-L-cysteine administration to mice. | Toxicology and applied pharmacology 20030415 |
| Functional properties of multispecific amino acid transporters and their implications to transporter-mediated toxicity. | The Journal of toxicological sciences 20030201 |
| Human mitochondrial and cytosolic branched-chain aminotransferases are cysteine S-conjugate beta-lyases, but turnover leads to inactivation. | Biochemical pharmacology 20030115 |
| Human kidney flavin-containing monooxygenases and their potential roles in cysteine s-conjugate metabolism and nephrotoxicity. | The Journal of pharmacology and experimental therapeutics 20030101 |
| Molecular mechanisms of renal tissue repair in survival from acute renal tubule necrosis: role of ERK1/2 pathway. | Toxicologic pathology 20030101 |
| Mitochondrial aspartate aminotransferase catalyses cysteine S-conjugate beta-lyase reactions. | The Biochemical journal 20021115 |
| Cellular energetics and glutathione status in NRK-52E cells: toxicological implications. | Biochemical pharmacology 20021115 |
| Protection of NRK-52E cells, a rat renal proximal tubular cell line, from chemical-induced apoptosis by overexpression of a mitochondrial glutathione transporter. | The Journal of pharmacology and experimental therapeutics 20021101 |
| Toxic, halogenated cysteine S-conjugates and targeting of mitochondrial enzymes of energy metabolism. | Biochemical pharmacology 20020815 |
| The effects of haloalkene cysteine conjugates on cytosolic free calcium levels in LLC-PK(1) cells--studies utilising digital imaging fluorescence microscopy. | Toxicology 20020614 |
| Interactions between collagen IV and collagen-binding integrins in renal cell repair after sublethal injury. | Molecular pharmacology 20011201 |
| Apoptosis, necrosis, and cell proliferation induced by S-(1,2-dichlorovinyl)-L-cysteine in primary cultures of human proximal tubular cells. | Toxicology and applied pharmacology 20011115 |
| Collagen IV promotes repair of renal cell physiological functions after toxicant injury. | American journal of physiology. Renal physiology 20010901 |
| Renal and hepatic toxicity of trichloroethylene and its glutathione-derived metabolites in rats and mice: sex-, species-, and tissue-dependent differences. | The Journal of pharmacology and experimental therapeutics 20010401 |
| Role of mitochondrial dysfunction in S-(1,2-dichlorovinyl)-l-cysteine-induced apoptosis. | Toxicology and applied pharmacology 20010201 |
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