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Record Information
Version	2.0
Creation Date	2012-05-31 13:02:43 -0600
Update Date	2015-06-03 15:53:38 -0600
Secondary Accession Numbers	ECMDB00965
Identification
Name:	Hypotaurine
Description	Hypotaurine is a product of enzyme cysteamine dioxygenase [EC 1.13.11.19] in taurine and hypotaurine metabolism pathway (KEGG). It may function as an antioxidant and a protective agent under physiological conditions (PMID 14992269).
Structure	MOLSDFPDBSMILESInChI × Structure for #<Compound:0xb56fcfc4> Close
Synonyms:	2-Amino-Ethanesulfinate 2-Amino-Ethanesulfinic acid 2-Amino-Ethanesulphinate 2-Amino-Ethanesulphinic acid 2-Aminoethanesulfinate 2-Aminoethanesulfinic acid 2-Aminoethanesulphinate 2-Aminoethanesulphinic acid 2-Aminoethylsulfinate 2-Aminoethylsulfinic acid 2-Aminoethylsulphinate 2-Aminoethylsulphinic acid Cystaminesulfinate Cystaminesulfinic acid Cystaminesulphinate Cystaminesulphinic acid Hypotaurine
Chemical Formula:	C2H7NO2S
Weight:	Average: 109.147 Monoisotopic: 109.019749163
InChI Key:	VVIUBCNYACGLLV-UHFFFAOYSA-N
InChI:	InChI=1S/C2H7NO2S/c3-1-2-6(4)5/h1-3H2,(H,4,5)
CAS number:	300-84-5
IUPAC Name:	2-aminoethane-1-sulfinic acid
Traditional IUPAC Name:	hypotaurine
SMILES:	NCCS(O)=O
Chemical Taxonomy
Description	belongs to the class of organic compounds known as sulfinic acids. Sulfinic acids are compounds containing a sulfinic acid functional group, with the general structure RS(=O)OH (R = organyl, not H).
Kingdom	Organic compounds
Super Class	Organic acids and derivatives
Class	Sulfinic acids and derivatives
Sub Class	Sulfinic acids
Direct Parent	Sulfinic acids
Alternative Parents	Alkanesulfinic acids Organosulfur compounds Organopnictogen compounds Organic oxides Monoalkylamines Hydrocarbon derivatives
Substituents	Sulfinic acid Alkanesulfinic acid Alkanesulfinic acid or derivatives Organic nitrogen compound Organic oxygen compound Organopnictogen compound Organic oxide Hydrocarbon derivative Primary amine Organosulfur compound Organonitrogen compound Primary aliphatic amine Amine Aliphatic acyclic compound
Molecular Framework	Aliphatic acyclic compounds
External Descriptors	aminosulfinic acid (CHEBI:16668 )
Physical Properties
State:	Solid
Charge:	0
Melting point:	Not Available
Experimental Properties:	Property Value Source
Predicted Properties	Property Value Source Water Solubility 38.8 g/L ALOGPS logP -1.2 ALOGPS logP -2.7 ChemAxon logS -0.45 ALOGPS pKa (Strongest Acidic) 1.68 ChemAxon pKa (Strongest Basic) 9.64 ChemAxon Physiological Charge 0 ChemAxon Hydrogen Acceptor Count 3 ChemAxon Hydrogen Donor Count 2 ChemAxon Polar Surface Area 63.32 Ų ChemAxon Rotatable Bond Count 2 ChemAxon Refractivity 23.16 m³·mol⁻¹ ChemAxon Polarizability 10.16 ų ChemAxon Number of Rings 0 ChemAxon Bioavailability 1 ChemAxon Rule of Five Yes ChemAxon Ghose Filter Yes ChemAxon Veber's Rule Yes ChemAxon MDDR-like Rule Yes ChemAxon
Biological Properties
Cellular Locations:	Cytoplasm
Reactions:	3-Sulfinoalanine <> Hypotaurine + Carbon dioxide 3-Sulfinoalanine > Hypotaurine + Carbon dioxide + Hypotaurine
SMPDB Pathways:	Not Available
KEGG Pathways:	Taurine and hypotaurine metabolism ec00430
EcoCyc Pathways:	Not Available
Concentrations
	Not Available
Spectra
Spectra:	Spectrum Type Description Splash Key GC-MS GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS) splash10-0udr-0900000000-6d1ec3a7649c0e7a704b View in MoNA GC-MS GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized) splash10-0f79-0900000000-468e3da761e4d86223b1 View in MoNA GC-MS GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS) splash10-0fki-5900000000-0569fb6d8502d22d2b7e View in MoNA GC-MS GC-MS Spectrum - GC-MS (3 TMS) splash10-0f79-0900000000-457c0f4ff1563d09a208 View in MoNA GC-MS GC-MS Spectrum - EI-B (Non-derivatized) splash10-0f79-0900000000-31e0a7f3a4c3fd20ce3c View in MoNA GC-MS GC-MS Spectrum - GC-EI-TOF (Non-derivatized) splash10-0udr-0900000000-6d1ec3a7649c0e7a704b View in MoNA GC-MS GC-MS Spectrum - GC-EI-TOF (Non-derivatized) splash10-0f79-0900000000-468e3da761e4d86223b1 View in MoNA GC-MS GC-MS Spectrum - GC-EI-TOF (Non-derivatized) splash10-0fki-5900000000-0569fb6d8502d22d2b7e View in MoNA GC-MS GC-MS Spectrum - GC-MS (Non-derivatized) splash10-0f79-0900000000-457c0f4ff1563d09a208 View in MoNA Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive splash10-000x-9000000000-ebfa02ce7482006f53d1 View in MoNA Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive Not Available View in JSpectraViewer LC-MS/MS LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated) splash10-01ox-9800000000-f121cbb956b42fc5e20e View in MoNA LC-MS/MS LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated) splash10-014i-9300000000-eec8c8d22a33d4e8da3b View in MoNA LC-MS/MS LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated) splash10-014i-9200000000-f461253126e9b74c7d80 View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive splash10-03di-0940100000-886905799c16b4d25a5f View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive splash10-0006-9000000000-a34ee572b02492eaefef View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive splash10-0006-9000000000-ff53f17dcba5f9b8c507 View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive splash10-0a4i-0900000000-a3ccc18b5af8fddfdffa View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive splash10-004i-0920000000-9c1032a24816a6221477 View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive splash10-0006-9000000000-6354cd263d6d293f1d61 View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive splash10-0a4i-0900000000-45a36787ef1f00274735 View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive splash10-004i-0900000000-318c8a0e0325b2e98a06 View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative splash10-0a4i-2900000000-123846d2dc8e7cf97137 View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative splash10-03di-9000000000-6b0caea8d77740b01ec0 View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative splash10-03di-9000000000-a5ce3fbe0fd14222c3c8 View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative splash10-03di-9000000000-32fdc560d98f6fd6be25 View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative splash10-03di-9000000000-5d74861c832bbb4f97fc View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive splash10-03di-6900000000-26d55a4c69512ce8ae79 View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive splash10-014i-9100000000-8fec2539fc653f7bc4d7 View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive splash10-014i-9000000000-6efe1a9b61e6af3e4d54 View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive splash10-014i-9000000000-519623b6e74aa699cb3b View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive splash10-014i-9000000000-6f298f33310e539b113f View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive splash10-03di-0900000000-6f2416e3d3c5aa1f0fff View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative splash10-03di-9300000000-85302e310b341400f079 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Positive splash10-03dl-6900000000-b26fa2070e91be8f8792 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-0006-9200000000-2252807899b1b8ebfc8e View in MoNA 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 2D NMR [1H,13C] 2D NMR Spectrum Not Available View in JSpectraViewer
References
References:	Dominy J, Eller S, Dawson R Jr: Building biosynthetic schools: reviewing compartmentation of CNS taurine synthesis. Neurochem Res. 2004 Jan;29(1):97-103. Pubmed: 14992267 Fontana, M., Pecci, L., Dupre, S., Cavallini, D. (2004). "Antioxidant properties of sulfinates: protective effect of hypotaurine on peroxynitrite-dependent damage." Neurochem Res 29:111-116. Pubmed: 14992269 Grafe F, Wohlrab W, Neubert RH, Brandsch M: Functional characterization of sodium- and chloride-dependent taurine transport in human keratinocytes. Eur J Pharm Biopharm. 2004 Mar;57(2):337-41. Pubmed: 15018993 Guerin P, Guillaud J, Menezo Y: Hypotaurine in spermatozoa and genital secretions and its production by oviduct epithelial cells in vitro. Hum Reprod. 1995 Apr;10(4):866-72. Pubmed: 7650134 Guerin P, Menezo Y: Hypotaurine and taurine in gamete and embryo environments: de novo synthesis via the cysteine sulfinic acid pathway in oviduct cells. Zygote. 1995 Nov;3(4):333-43. Pubmed: 8730898 Holmes RP, Goodman HO, Shihabi ZK, Jarow JP: The taurine and hypotaurine content of human semen. J Androl. 1992 May-Jun;13(3):289-92. Pubmed: 1601750 Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510 Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882 Krieg RC, Uihlein D, Murthum T, Endlicher E, Hausmann F, Messmann H, Knuechel R: Improving the use of 5-aminolevulinic acid (ALA)-induced protoporphyrin IX (PPIX) for the gastrointestinal tract by esterification--an in vitro study. Cell Mol Biol (Noisy-le-grand). 2002 Dec;48(8):917-23. Pubmed: 12699251 Mahadevan MM, Trounson AO: Removal of the cumulus oophorus from the human oocyte for in vitro fertilization. Fertil Steril. 1985 Feb;43(2):263-7. Pubmed: 3967784 Masuoka N, Yao K, Kinuta M, Ohta J, Wakimoto M, Ubuka T: High-performance liquid chromatographic determination of taurine and hypotaurine using 3,5-dinitrobenzoyl chloride as derivatizing reagent. J Chromatogr B Biomed Appl. 1994 Oct 3;660(1):31-5. Pubmed: 7858721 Pitari G, Dupre S, Spirito A, Antonini G, Amicarelli F: Hypotaurine protection on cell damage by singlet oxygen. Adv Exp Med Biol. 2000;483:157-62. Pubmed: 11787593 Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. Pubmed: 19212411
Synthesis Reference:	Owen, Terence C.; Wilbraham, A. C. Convenient preparation and characterization of hypotaurine. Journal of the Chemical Society (1965), (Jan.), 826-7.
Material Safety Data Sheet (MSDS)	Not Available
Links
External Links:	Resource Link CHEBI ID 16668 HMDB ID HMDB00965 Pubchem Compound ID 107812 Kegg ID C00519 ChemSpider ID 96959 Wikipedia ID Hypotaurine BioCyc ID HYPOTAURINE EcoCyc ID HYPOTAURINE

Enzymes