Record Information
Version2.0
Creation Date2012-05-31 13:02:43 -0600
Update Date2015-06-03 15:53:38 -0600
Secondary Accession Numbers
  • ECMDB00965
Identification
Name:Hypotaurine
DescriptionHypotaurine 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
Thumb
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).
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassSulfinic acids and derivatives
Sub ClassSulfinic acids
Direct ParentSulfinic acids
Alternative Parents
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 FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
State:Solid
Charge:0
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility38.8 g/LALOGPS
logP-1.2ALOGPS
logP-2.7ChemAxon
logS-0.45ALOGPS
pKa (Strongest Acidic)1.68ChemAxon
pKa (Strongest Basic)9.64ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area63.32 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity23.16 m³·mol⁻¹ChemAxon
Polarizability10.16 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
SMPDB Pathways:Not Available
KEGG Pathways:
  • Taurine and hypotaurine metabolism ec00430
EcoCyc Pathways:Not Available
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)splash10-0udr-0900000000-6d1ec3a7649c0e7a704bView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-0f79-0900000000-468e3da761e4d86223b1View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)splash10-0fki-5900000000-0569fb6d8502d22d2b7eView in MoNA
GC-MSGC-MS Spectrum - GC-MS (3 TMS)splash10-0f79-0900000000-457c0f4ff1563d09a208View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0f79-0900000000-31e0a7f3a4c3fd20ce3cView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0udr-0900000000-6d1ec3a7649c0e7a704bView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0f79-0900000000-468e3da761e4d86223b1View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0fki-5900000000-0569fb6d8502d22d2b7eView in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0f79-0900000000-457c0f4ff1563d09a208View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-000x-9000000000-ebfa02ce7482006f53d1View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-0a4i-2900000000-123846d2dc8e7cf97137View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-03di-9000000000-6b0caea8d77740b01ec0View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-03di-9000000000-a5ce3fbe0fd14222c3c8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-03di-9000000000-32fdc560d98f6fd6be25View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-03di-9000000000-5d74861c832bbb4f97fcView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-03di-9300000000-85302e310b341400f079View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a4i-2900000000-123846d2dc8e7cf97137View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-03di-9000000000-6b0caea8d77740b01ec0View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-03di-9000000000-a5ce3fbe0fd14222c3c8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-03di-9000000000-32fdc560d98f6fd6be25View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-03di-9000000000-5d74861c832bbb4f97fcView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-03di-9300000000-85302e310b341400f079View in MoNA
LC-MS/MSLC-MS/MS Spectrum - , negativesplash10-03di-9200000000-dcffc1a76d64346e7107View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-01ox-9800000000-f121cbb956b42fc5e20eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-014i-9300000000-eec8c8d22a33d4e8da3bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-014i-9200000000-f461253126e9b74c7d80View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-03di-0940100000-886905799c16b4d25a5fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0006-9000000000-a34ee572b02492eaefefView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0006-9000000000-ff53f17dcba5f9b8c507View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0a4i-0900000000-a3ccc18b5af8fddfdffaView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-004i-0920000000-9c1032a24816a6221477View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0006-9000000000-6354cd263d6d293f1d61View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0a4i-0900000000-45a36787ef1f00274735View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-004i-0900000000-318c8a0e0325b2e98a06View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-03di-6900000000-26d55a4c69512ce8ae79View in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView 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
External Links:
ResourceLink
CHEBI ID16668
HMDB IDHMDB00965
Pubchem Compound ID107812
Kegg IDC00519
ChemSpider ID96959
Wikipedia IDHypotaurine
BioCyc IDHYPOTAURINE
EcoCyc IDHYPOTAURINE

Enzymes

General function:
Involved in glutamate decarboxylase activity
Specific function:
Converts glutamate to gamma-aminobutyrate (GABA), consuming one intracellular proton in the reaction. The gad system helps to maintain a near-neutral intracellular pH when cells are exposed to extremely acidic conditions. The ability to survive transit through the acidic conditions of the stomach is essential for successful colonization of the mammalian host by commensal and pathogenic bacteria
Gene Name:
gadA
Uniprot ID:
P69908
Molecular weight:
52685
Reactions
L-glutamate = 4-aminobutanoate + CO(2).
General function:
Involved in glutamate decarboxylase activity
Specific function:
Converts glutamate to gamma-aminobutyrate (GABA), consuming one intracellular proton in the reaction. The gad system helps to maintain a near-neutral intracellular pH when cells are exposed to extremely acidic conditions. The ability to survive transit through the acidic conditions of the stomach is essential for successful colonization of the mammalian host by commensal and pathogenic bacteria
Gene Name:
gadB
Uniprot ID:
P69910
Molecular weight:
52668
Reactions
L-glutamate = 4-aminobutanoate + CO(2).