Record Information
Version 1.0
Update Date 1/22/2018 12:54:54 PM
Metabolite IDPAMDB000106
Identification
Name: Taurine
Description:Taurine is a sulfur amino acid like methionine, cystine, cysteine and homocysteine. It is a lesser-known amino acid because it is not incorporated into the structural building blocks of protein. Taurine has many diverse biological functions serving as a stabilizer of cell membranes and a facilitator in the transport of ions such as sodium, potassium, calcium and magnesium.
Structure
Thumb
Synonyms:
  • 1-Aminoethane-2-sulfonate
  • 1-Aminoethane-2-sulfonic acid
  • 1-Aminoethane-2-sulphonate
  • 1-Aminoethane-2-sulphonic acid
  • 2-Aminoethanesulfonate
  • 2-Aminoethanesulfonic acid
  • 2-Aminoethanesulphonate
  • 2-Aminoethanesulphonic acid
  • 2-Aminoethylsulfonate
  • 2-Aminoethylsulfonic acid
  • 2-Aminoethylsulphonate
  • 2-Aminoethylsulphonic acid
  • 2-Sulfoethylamine
  • 2-Sulphoethylamine
  • Aminoethylsulfonate
  • Aminoethylsulfonic acid
  • Aminoethylsulphonate
  • Aminoethylsulphonic acid
  • Aminoetylsulfonate
  • Aminoetylsulfonic acid
  • Aminoetylsulphonate
  • Aminoetylsulphonic acid
  • B-Aminoethylsulfonate
  • B-Aminoethylsulfonic acid
  • B-Aminoethylsulphonate
  • B-Aminoethylsulphonic acid
  • Beta-Aminoethylsulfonate
  • Beta-Aminoethylsulfonic acid
  • Beta-Aminoethylsulphonate
  • Beta-Aminoethylsulphonic acid
  • Ethylaminesulfonate
  • Ethylaminesulfonic acid
  • Ethylaminesulphonate
  • Ethylaminesulphonic acid
  • Taufon
  • Tauphon
  • Taurine
  • β-Aminoethylsulfonate
  • β-Aminoethylsulfonic acid
  • β-Aminoethylsulphonate
  • β-Aminoethylsulphonic acid
Chemical Formula: C2H7NO3S
Average Molecular Weight: 125.147
Monoisotopic Molecular Weight: 125.014663785
InChI Key: XOAAWQZATWQOTB-UHFFFAOYSA-N
InChI:InChI=1S/C2H7NO3S/c3-1-2-7(4,5)6/h1-3H2,(H,4,5,6)
CAS number: 107-35-7
IUPAC Name:2-aminoethane-1-sulfonic acid
Traditional IUPAC Name: taurine
SMILES:NCCS(O)(=O)=O
Chemical Taxonomy
Taxonomy DescriptionThis compound belongs to the class of organic compounds known as sulfonic acids. These are compounds containing the sulfonic acid group, which has the general structure RS(=O)2OH (R is not a hydrogen atom).
Kingdom Organic compounds
Super ClassOrganic acids and derivatives
Class Sulfonic acids and derivatives
Sub ClassSulfonic acids
Direct Parent Sulfonic acids
Alternative Parents
Substituents
  • Alkanesulfonic acid
  • Sulfonyl
  • Sulfonic acid
  • Hydrocarbon derivative
  • Primary amine
  • Organosulfur compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Amine
  • Aliphatic acyclic compound
Molecular Framework Aliphatic acyclic compounds
External Descriptors
Physical Properties
State: Solid
Charge:0
Melting point: 300 °C
Experimental Properties:
PropertyValueSource
Water Solubility:80.7 mg/mL [YALKOWSKY,SH & DANNENFELSER,RM (1992)]PhysProp
Predicted Properties
PropertyValueSource
Water Solubility105.0 mg/mLALOGPS
logP-2.2ALOGPS
logP-2.6ChemAxon
logS-0.08ALOGPS
pKa (Strongest Acidic)-1.5ChemAxon
pKa (Strongest Basic)9.34ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area80.39 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity24.61 m3·mol-1ChemAxon
Polarizability10.82 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Cytoplasm
Reactions:
Pathways:
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)splash10-0032-1901000000-5373a9d32fa1f29b8012View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)splash10-0032-0901000000-f7cf5a7ef7741fe71454View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)splash10-00di-9802000000-c315203efd199b1871e7View in MoNA
GC-MSGC-MS Spectrum - GC-MSNot Available
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-004i-0900000000-57e6677f8d16d2985bfcView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0006-9100000000-6c843965de2368577a54View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0006-9200000000-bc9330a846bf43b4bd3fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-001i-0910000000-3db15ccd0e35f4d28cffView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0uk9-9800000000-2b8831b551e784a41008View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0a4i-0900000000-773b190e6818e815f3c9View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-000i-9000000000-a6f41eee062c4713d181View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-004i-0920000000-a558d03e31ae58106185View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0a4i-0900000000-9cd32466db0b0c9c5c55View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-004i-0900000000-06101a50ac12515e4fd0View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-004i-0900000000-10d63d9e046e843a5fcaView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-006t-0890202100-ef2de9b47cafa707f789View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-004i-9300000000-530438ccab9f22503af5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-00di-0900000000-ad642e440d924dfd8e20View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-006t-0097000000-24cfd722ea30b6a3b22dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-006t-0790202100-45d57f0101d4cefbc981View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-004i-9300000000-bd1f04d82f9e675f2303View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-00di-0900000000-d411fff703670832e445View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-006t-0098000000-c86b66ff71cff513520fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-00di-0900000000-31f44189a2671cf5d2e9View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-00e9-6900000000-cc7fe1badfe13959526dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-001i-9000000000-ae6465f92e91cfad7276View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-001i-9000000000-af0ea33a51fe79abee00View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-001i-9000000000-27d6c7ae55f73bb21b3cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-004i-2900000000-a48be30a953f106419c0View in MoNA
MSMass Spectrum (Electron Ionization)splash10-0036-9000000000-a96a1a8b53b1b556f6caView in MoNA
1D NMR13C NMR SpectrumNot Available
1D NMR1H NMR SpectrumNot Available
1D NMR1H NMR SpectrumNot Available
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,1H] 2D NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
References
References:
  • Axelson M, Ellis E, Mork B, Garmark K, Abrahamsson A, Bjorkhem I, Ericzon BG, Einarsson C: Bile acid synthesis in cultured human hepatocytes: support for an alternative biosynthetic pathway to cholic acid. Hepatology. 2000 Jun;31(6):1305-12. Pubmed: 10827156
  • Cynober LA: Plasma amino acid levels with a note on membrane transport: characteristics, regulation, and metabolic significance. Nutrition. 2002 Sep;18(9):761-6. Pubmed: 12297216
  • Engelborghs S, Marescau B, De Deyn PP: Amino acids and biogenic amines in cerebrospinal fluid of patients with Parkinson's disease. Neurochem Res. 2003 Aug;28(8):1145-50. Pubmed: 12834252
  • Gonzalez-Quevedo A, Obregon F, Fernandez R, Santiesteban R, Serrano C, Lima L: Amino acid levels and ratios in serum and cerebrospinal fluid of patients with optic neuropathy in Cuba. Nutr Neurosci. 2001;4(1):51-62. Pubmed: 11842876
  • Gonzalez-Quevedo A, Obregon F, Santiesteban Freixas R, Fernandez R, Lima L: [Amino acids as biochemical markers in epidemic and endemic optic neuropathies] Rev Cubana Med Trop. 1998;50 Suppl:241-4. Pubmed: 10349454
  • Goodman HO, Shihabi Z, Oles KS: Antiepileptic drugs and plasma and platelet taurine in epilepsy. Epilepsia. 1989 Mar-Apr;30(2):201-7. Pubmed: 2494044
  • Hagenfeldt L, Bjerkenstedt L, Edman G, Sedvall G, Wiesel FA: Amino acids in plasma and CSF and monoamine metabolites in CSF: interrelationship in healthy subjects. J Neurochem. 1984 Mar;42(3):833-7. Pubmed: 6198473
  • Hu S, Zhao X, Yin S, Meng J: [A study on the mechanism of taurine postponing the aging process of human fetal brain neural cells] Wei Sheng Yan Jiu. 1997 Mar;26(2):98-101. Pubmed: 10325611
  • 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
  • Khan SA, Cox IJ, Hamilton G, Thomas HC, Taylor-Robinson SD: In vivo and in vitro nuclear magnetic resonance spectroscopy as a tool for investigating hepatobiliary disease: a review of H and P MRS applications. Liver Int. 2005 Apr;25(2):273-81. Pubmed: 15780050
  • Kopple JD, Vinton NE, Laidlaw SA, Ament ME: Effect of intravenous taurine supplementation on plasma, blood cell, and urine taurine concentrations in adults undergoing long-term parenteral nutrition. Am J Clin Nutr. 1990 Nov;52(5):846-53. Pubmed: 2122710
  • Learn DB, Fried VA, Thomas EL: Taurine and hypotaurine content of human leukocytes. J Leukoc Biol. 1990 Aug;48(2):174-82. Pubmed: 2370482
  • McCarty MF: Complementary vascular-protective actions of magnesium and taurine: a rationale for magnesium taurate. Med Hypotheses. 1996 Feb;46(2):89-100. Pubmed: 8692051
  • McMahon GP, O'Kennedy R, Kelly MT: High-performance liquid chromatographic determination of taurine in human plasma using pre-column extraction and derivatization. J Pharm Biomed Anal. 1996 Jun;14(8-10):1287-94. Pubmed: 8818047
  • Miglis M, Wilder D, Reid T, Bakaltcheva I: Effect of taurine on platelets and the plasma coagulation system. Platelets. 2002 Feb;13(1):5-10. Pubmed: 11918831
  • Peng CT, Wu KH, Lan SJ, Tsai JJ, Tsai FJ, Tsai CH: Amino acid concentrations in cerebrospinal fluid in children with acute lymphoblastic leukemia undergoing chemotherapy. Eur J Cancer. 2005 May;41(8):1158-63. Epub 2005 Apr 14. Pubmed: 15911239
  • Rainesalo S, Keranen T, Palmio J, Peltola J, Oja SS, Saransaari P: Plasma and cerebrospinal fluid amino acids in epileptic patients. Neurochem Res. 2004 Jan;29(1):319-24. Pubmed: 14992292
  • Schneider SM, Joly F, Gehrardt MF, Badran AM, Myara A, Thuillier F, Coudray-Lucas C, Cynober L, Trivin F, Messing B: Taurine status and response to intravenous taurine supplementation in adults with short-bowel syndrome undergoing long-term parenteral nutrition: a pilot study. Br J Nutr. 2006 Aug;96(2):365-70. Pubmed: 16923232
  • 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
  • Stover JF, Morganti-Kosmann MC, Lenzlinger PM, Stocker R, Kempski OS, Kossmann T: Glutamate and taurine are increased in ventricular cerebrospinal fluid of severely brain-injured patients. J Neurotrauma. 1999 Feb;16(2):135-42. Pubmed: 10098958
  • Sturman JA, Messing JM, Rossi SS, Hofmann AF, Neuringer MD: Tissue taurine content and conjugated bile acid composition of rhesus monkey infants fed a human infant soy-protein formula with or without taurine supplementation for 3 months. Neurochem Res. 1988 Apr;13(4):311-6. Pubmed: 3393260
  • van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195
  • Vinton NE, Laidlaw SA, Ament ME, Kopple JD: Taurine concentrations in plasma, blood cells, and urine of children undergoing long-term total parenteral nutrition. Pediatr Res. 1987 Apr;21(4):399-403. Pubmed: 3106924
  • Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. Pubmed: 18331064
Synthesis Reference: Hu, Libo; Zhu, Hui; Du, Da-Ming; Xu, Jiaxi. Efficient synthesis of taurine and structurally diverse substituted taurines from aziridines. Journal of Organic Chemistry (2007), 72(12), 4543-4546.
Material Safety Data Sheet (MSDS) Download (PDF)
External Links:
ResourceLink
CHEBI ID15891
HMDB IDHMDB00251
Pubchem Compound ID1123
Kegg IDC00245
ChemSpider ID1091
WikipediaTaurine
BioCyc IDTAURINE
EcoCyc IDTAURINE
Ligand ExpoTAU

Enzymes

General function:
Involved in gamma-glutamyltransferase activity
Specific function:
(5-L-glutamyl)-peptide + an amino acid = peptide + 5-L-glutamyl amino acid
Gene Name:
ggt
Locus Tag:
PA1338
Molecular weight:
59.9 kDa
Reactions
A (5-L-glutamyl)-peptide + an amino acid = a peptide + a 5-L-glutamyl amino acid.
Glutathione + H(2)O = L-cysteinylglycine + L-glutamate.
General function:
Involved in oxidoreductase activity
Specific function:
Catalyzes the conversion of taurine and alpha ketoglutarate to sulfite, aminoacetaldehyde and succinate. Required for the utilization of taurine (2-aminoethanesulfonic acid) as an alternative sulfur source. Pentane-sulfonic acid, 3- (N-morpholino)propanesulfonic acid and 1,3-dioxo-2- isoindolineethanesulfonic acid are also substrates for this enzyme
Gene Name:
tauD
Locus Tag:
PA3935
Molecular weight:
31 kDa
Reactions
Taurine + 2-oxoglutarate + O(2) = sulfite + aminoacetaldehyde + succinate + CO(2).
General function:
Involved in transporter activity
Specific function:
Part of a binding-protein-dependent transport system for taurine. Probably responsible for the translocation of the substrate across the membrane
Gene Name:
tauC
Locus Tag:
PA3936
Molecular weight:
29.4 kDa
General function:
Involved in nucleotide binding
Specific function:
Part of the ABC transporter complex TauABC involved in taurine import. Responsible for energy coupling to the transport system
Gene Name:
tauB
Locus Tag:
PA3937
Molecular weight:
28.8 kDa
Reactions
ATP + H(2)O + taurine(Out) = ADP + phosphate + taurine(In).
General function:
Involved in transporter activity
Specific function:
Part of a binding-protein-dependent transport system for taurine
Gene Name:
tauA
Locus Tag:
PA3938
Molecular weight:
35.9 kDa

Transporters

General function:
Involved in transporter activity
Specific function:
Part of a binding-protein-dependent transport system for taurine. Probably responsible for the translocation of the substrate across the membrane
Gene Name:
tauC
Locus Tag:
PA3936
Molecular weight:
29.4 kDa
General function:
Involved in nucleotide binding
Specific function:
Part of the ABC transporter complex TauABC involved in taurine import. Responsible for energy coupling to the transport system
Gene Name:
tauB
Locus Tag:
PA3937
Molecular weight:
28.8 kDa
Reactions
ATP + H(2)O + taurine(Out) = ADP + phosphate + taurine(In).
General function:
Involved in transporter activity
Specific function:
Part of a binding-protein-dependent transport system for taurine
Gene Name:
tauA
Locus Tag:
PA3938
Molecular weight:
35.9 kDa