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 |
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| The taurine and hypotaurine content of human semen. | 1992 May-Jun |
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| Treatment of YAC128 mice and their wild-type littermates with cystamine does not lead to its accumulation in plasma or brain: implications for the treatment of Huntington disease. | 2005 Aug |
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| Role of oxidative stress in female reproduction. | 2005 Jul 14 |
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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 |
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| Effect of UVA and UVB irradiation on the metabolic profile of rabbit cornea and lens analysed by HR-MAS 1H NMR spectroscopy. | 2006 |
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| Effects of consecutive high-dose alcohol administration on the utilization of sulfur-containing amino acids by rats. | 2006 Jan |
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| Effects of bovine spermatozoa preparation on embryonic development in vitro. | 2006 Nov 13 |
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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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| Discovery and characterization of a second mammalian thiol dioxygenase, cysteamine dioxygenase. | 2007 Aug 31 |
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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 Fall |
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| Control of human trophoblast function. | 2007 Feb 8 |
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| Overexpression of cysteine dioxygenase reduces intracellular cysteine and glutathione pools in HepG2/C3A cells. | 2007 Jul |
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| Validation of reference genes for quantitative RT-PCR studies in porcine oocytes and preimplantation embryos. | 2007 May 31 |
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| Glutamine and hypotaurine improves intracellular oxidative status and in vitro development of porcine preimplantation embryos. | 2007 Nov |
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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 Nov |
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| Metabolome based reaction graphs of M. tuberculosis and M. leprae: a comparative network analysis. | 2007 Sep 12 |
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| Systemic multicompartmental effects of the gut microbiome on mouse metabolic phenotypes. | 2008 |
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| The protective effect of hypotaurine and cysteine sulphinic acid on peroxynitrite-mediated oxidative reactions. | 2008 Apr |
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| Comparison of the effects of buthioninesulfoximine and phorone on the metabolism of sulfur-containing amino acids in rat liver. | 2008 Apr 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 Apr 18 |
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| Hypotaurine and sulfhydryl-containing antioxidants reduce H2S toxicity in erythrocytes from a marine invertebrate. | 2008 Dec |
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| Effects of homocysteine on metabolic pathways in cultured astrocytes. | 2008 Jun |
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| Identifying differential correlation in gene/pathway combinations. | 2008 Nov 18 |
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| Evidence for conserved DNA and histone H3 methylation reprogramming in mouse, bovine and rabbit zygotes. | 2008 Nov 3 |
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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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| Functional genomics of HMGN3a and SMARCAL1 in early mammalian embryogenesis. | 2009 Apr 24 |
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| Effects of hypotaurine, cysteamine and aminoacids solution on post-thaw microscopic and oxidative stress parameters of Angora goat semen. | 2009 Dec |
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| Taurine supplementation improves the utilization of sulfur-containing amino acids in rats continually administrated alcohol. | 2009 Feb |
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| Muscarinic receptor regulation of osmosensitive taurine transport in human SH-SY5Y neuroblastoma cells. | 2009 Jan |
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| Effects of taurine and hypotaurine supplementation and ionophore concentrations on post-thaw acrosome reaction of dog spermatozoa. | 2009 Jan 15 |
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| A practical novel method for ensuring stable capacitation of spermatozoa from cryopreserved C57BL/6J sperm suspension. | 2009 Jul |
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| Taurine Chloramine Activates Nrf2, Increases HO-1 Expression and Protects Cells from Death Caused by Hydrogen Peroxide. | 2009 Jul |
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| Thiotaurine and hypotaurine contents in hydrothermal-vent polychaetes without thiotrophic endosymbionts: correlation With sulfide exposure. | 2009 Jul 1 |
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| Nucleologenesis and embryonic genome activation are defective in interspecies cloned embryos between bovine ooplasm and rhesus monkey somatic cells. | 2009 Jul 28 |
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| Reconstruction of metabolic pathways for the cattle genome. | 2009 Mar 12 |
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| Women with endometriosis improved their peripheral antioxidant markers after the application of a high antioxidant diet. | 2009 May 28 |
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| An evaluation of minimal cellular functions to sustain a bacterial cell. | 2009 Nov 28 |
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| Ascorbic Acid in human seminal plasma: determination and its relationship to sperm quality. | 2009 Sep |
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| Identification of functional modules that correlate with phenotypic difference: the influence of network topology. | 2010 |
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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 Apr |
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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 Jan |
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| NMR-based metabolic profiling identifies biomarkers of liver regeneration following partial hepatectomy in the rat. | 2010 Jan |
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| Hypotaurine is an Energy-Saving Hepatoprotective Compound against Ischemia-Reperfusion Injury of the Rat Liver. | 2010 Mar |
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| Linking toxicant physiological mode of action with induced gene expression changes in Caenorhabditis elegans. | 2010 Mar 23 |
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| Ex-vivo HRMAS of adult brain tumours: metabolite quantification and assignment of tumour biomarkers. | 2010 Mar 23 |
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| Cystamine metabolism and brain transport properties: clinical implications for neurodegenerative diseases. | 2010 Sep |
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
