Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C2H7NO2S |
| Molecular Weight | 109.147 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
NCCS(O)=O
InChI
InChIKey=VVIUBCNYACGLLV-UHFFFAOYSA-N
InChI=1S/C2H7NO2S/c3-1-2-6(4)5/h1-3H2,(H,4,5)
Hypotaurine (2-aminoethane sulinic acid) is the immediate precursor of taurine (2-aminoethane sulfonic acid) which is one of the most abundant free amino acids in the central nervous system. Although hypotaurine and taurine are mainly supplied from blood plasma across the blood-brain barrier in the brain, they are also synthesized from cysteine and cysteamine by astrocytes and neurons. Hypotaurine acts as an endogenous neurotransmitter via action on the glycine receptors. It was shown, that hypotaurine might be used as an effective therapeutics for orofacial pain. Also in vitro studies were conducted to show that hypotaurine activates hypoxia signaling through the competitive inhibition of prolyl hydroxylase domain-2. Moreover, was made a suggestion, that the hypotaurine metabolic pathway may provide a potential new target for glioblastoma diagnosis and therapy.
CNS Activity
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Cystamine metabolism and brain transport properties: clinical implications for neurodegenerative diseases. | 2010-09 |
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| Enhancement of menadione stress tolerance in yeast by accumulation of hypotaurine and taurine: co-expression of cDNA clones, from Cyprinus carpio, for cysteine dioxygenase and cysteine sulfinate decarboxylase in Saccharomyces cerevisiae. | 2010-04 |
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| Linking toxicant physiological mode of action with induced gene expression changes in Caenorhabditis elegans. | 2010-03-23 |
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| Ex-vivo HRMAS of adult brain tumours: metabolite quantification and assignment of tumour biomarkers. | 2010-03-23 |
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| Hypotaurine is an Energy-Saving Hepatoprotective Compound against Ischemia-Reperfusion Injury of the Rat Liver. | 2010-03 |
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| Isolation of plasma membrane vesicles from mouse placenta at term and measurement of system A and system beta amino acid transporter activity. | 2010-01 |
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| NMR-based metabolic profiling identifies biomarkers of liver regeneration following partial hepatectomy in the rat. | 2010-01 |
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| Identification of functional modules that correlate with phenotypic difference: the influence of network topology. | 2010 |
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| Effects of hypotaurine, cysteamine and aminoacids solution on post-thaw microscopic and oxidative stress parameters of Angora goat semen. | 2009-12 |
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| An evaluation of minimal cellular functions to sustain a bacterial cell. | 2009-11-28 |
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| Ascorbic Acid in human seminal plasma: determination and its relationship to sperm quality. | 2009-09 |
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| Nucleologenesis and embryonic genome activation are defective in interspecies cloned embryos between bovine ooplasm and rhesus monkey somatic cells. | 2009-07-28 |
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| Thiotaurine and hypotaurine contents in hydrothermal-vent polychaetes without thiotrophic endosymbionts: correlation With sulfide exposure. | 2009-07-01 |
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| A practical novel method for ensuring stable capacitation of spermatozoa from cryopreserved C57BL/6J sperm suspension. | 2009-07 |
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| Taurine Chloramine Activates Nrf2, Increases HO-1 Expression and Protects Cells from Death Caused by Hydrogen Peroxide. | 2009-07 |
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| Women with endometriosis improved their peripheral antioxidant markers after the application of a high antioxidant diet. | 2009-05-28 |
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| Functional genomics of HMGN3a and SMARCAL1 in early mammalian embryogenesis. | 2009-04-24 |
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| Reconstruction of metabolic pathways for the cattle genome. | 2009-03-12 |
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| Taurine supplementation improves the utilization of sulfur-containing amino acids in rats continually administrated alcohol. | 2009-02 |
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| Effects of taurine and hypotaurine supplementation and ionophore concentrations on post-thaw acrosome reaction of dog spermatozoa. | 2009-01-15 |
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| Muscarinic receptor regulation of osmosensitive taurine transport in human SH-SY5Y neuroblastoma cells. | 2009-01 |
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| The effects of taurine, hypotaurine, and taurine homologs on erythrocyte morphology, membrane fluidity and cytoskeletal spectrin alterations due to diabetes, alcoholism and diabetes-alcoholism in the rat. | 2009 |
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| The effects of taurine, taurine homologs and hypotaurine on cell and membrane antioxidative system alterations caused by type 2 diabetes in rat erythrocytes. | 2009 |
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| Hypotaurine and sulfhydryl-containing antioxidants reduce H2S toxicity in erythrocytes from a marine invertebrate. | 2008-12 |
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| In vitro production of llama (Lama glama) embryos by IVF and ICSI with fresh semen. | 2008-12 |
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| Identifying differential correlation in gene/pathway combinations. | 2008-11-18 |
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| Evidence for conserved DNA and histone H3 methylation reprogramming in mouse, bovine and rabbit zygotes. | 2008-11-03 |
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| Effects of homocysteine on metabolic pathways in cultured astrocytes. | 2008-06 |
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| Production of hypotaurine from L-cysteinesulfinate by rat liver mitochondria. | 2008-06 |
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| Comparison of the effects of buthioninesulfoximine and phorone on the metabolism of sulfur-containing amino acids in rat liver. | 2008-04-18 |
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| Stimulated efflux of amino acids and glutathione from cultured hippocampal slices by omission of extracellular calcium: likely involvement of connexin hemichannels. | 2008-04-18 |
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| Alleviation of acute ethanol-induced liver injury and impaired metabolomics of S-containing substances by betaine supplementation. | 2008-04-18 |
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| The protective effect of hypotaurine and cysteine sulphinic acid on peroxynitrite-mediated oxidative reactions. | 2008-04 |
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| Parthenogenetic activation of bovine oocytes using bovine and murine phospholipase C zeta. | 2008-02-19 |
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| Systemic multicompartmental effects of the gut microbiome on mouse metabolic phenotypes. | 2008 |
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| Glutamine and hypotaurine improves intracellular oxidative status and in vitro development of porcine preimplantation embryos. | 2007-11 |
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| Incorporation of taurine and hypotaurine did not improve the efficiency of the Uppsala Equex II extender for dog semen freezing. | 2007-11 |
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| Metabolome based reaction graphs of M. tuberculosis and M. leprae: a comparative network analysis. | 2007-09-12 |
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| Discovery and characterization of a second mammalian thiol dioxygenase, cysteamine dioxygenase. | 2007-08-31 |
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| Overexpression of cysteine dioxygenase reduces intracellular cysteine and glutathione pools in HepG2/C3A cells. | 2007-07 |
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| Validation of reference genes for quantitative RT-PCR studies in porcine oocytes and preimplantation embryos. | 2007-05-31 |
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| Function and regulation of taurine transport at the inner blood-retinal barrier. | 2007-03 |
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| Control of human trophoblast function. | 2007-02-08 |
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| Effects of taurine on plasma and liver lipids, erythrocyte ouabain sensitive Na efflux and platelet aggregation in Sprague Dawley rats. | 2007 |
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| Taurine chloramine differentially inhibits matrix metalloproteinase 1 and 13 synthesis in interleukin-1beta stimulated fibroblast-like synoviocytes. | 2007 |
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| Observing metabolic functions at the genome scale. | 2007 |
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| Comparison of the effects of taurine with those of related sulfur-containing compounds on pyridoxal-induced adrenomedullary catecholamine release and glycogenolysis in the rat. | 2006 |
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| In vivo regulation of cysteine dioxygenase via the ubiquitin-26S proteasome system. | 2006 |
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| Cysteamine dioxygenase: evidence for the physiological conversion of cysteamine to hypotaurine in rat and mouse tissues. | 2006 |
|
| The reactivity of hypotaurine and cysteine sulfinic acid with peroxynitrite. | 2006 |
Patents
Sample Use Guides
The occupation of hypotaurine in prolyl hydroxylase domain-2 (PHD2)’s catalytic center suggests that it may serve as a competitive inhibitor to PHD2, with consequential abnormal activation of hypoxia signaling. Immunoprecipitation was used to evaluate the hydroxylated form of HIF-1α (HO-HIF1α) in the presence of hypotaurine. Hypotaurine reduced the levels of HO-HIF-1α in U251 cells, with hypotaurine concentrations of 0, 0.5 and 1mM showing qualitative stepwise decreases in HO-HIF-1α. It was also found that prolyl hydroxylation was attenuated by hypotaurine incubation, with a reduction in hydroxylation of 66.7% at 2.5mM hypotaurine and 82.0% at 5mM hypotaurine, respectively. Further, we found the protein ubiquitination of HIF-1/2α was reduced in U87 cells treated with 5mM hypotaurine, suggesting a decrease in HIF-1/2α degradation. Finally, a cyclohexamide (CHX) pulse chase assay demonstrated that hypotaurine extended the half-life of HIF-1α (20.67 min to 69.14 min) and HIF-2α (21.38 min to 59.71 min), indicating hypoxia signaling is activated due to the presence of hypotaurine
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57853
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DTXSID8075380
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5L08GE4332
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2597523
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HYPOTAURINE
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C003949
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5L08GE4332
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16668
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300-84-5
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107812
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SUBSTANCE RECORD
