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Taurine (YMDB00772)

Identification
YMDB IDYMDB00772
NameTaurine
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
DescriptionTaurine, also known as 2-sulfoethylamine or taufon, belongs to the class of organic compounds known as organosulfonic acids. Organosulfonic acids are compounds containing the sulfonic acid group, which has the general structure RS(=O)2OH (R is not a hydrogen atom). Taurine is a very strong basic compound (based on its pKa). Taurine exists in all living species, ranging from bacteria to humans. Taurine is a potentially toxic compound.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
  • -Aminoethylsulfonic acid
  • 1-Aminoethane-2-sulfonate
  • 1-Aminoethane-2-sulfonic acid
  • 2-Aminoethanesulfonate
  • 2-aminoethanesulfonic acid
  • 2-aminoethyl sulfonate
  • 2-Aminoethylsulfonate
  • 2-Aminoethylsulfonic acid
  • 2-Sulfoethylamine
  • Aminoethanesulfonic acid
  • Aminoethylsulfonate
  • Aminoethylsulfonic acid
  • b-Aminoethylsulfonate
  • b-Aminoethylsulfonic acid
  • beta-Aminoethylsulfonate
  • beta-Aminoethylsulfonic acid
  • Ethanesulfonic acid, 2-amino-
  • O-Due
  • Taurine
  • 2-Aminoethanesulphonate
  • 2-Aminoethanesulphonic acid
  • 2-Aminoethyl sulfonic acid
  • 2-Aminoethyl sulphonate
  • 2-Aminoethyl sulphonic acid
  • Aminoethylsulphonate
  • Aminoethylsulphonic acid
  • b-Aminoethylsulphonate
  • b-Aminoethylsulphonic acid
  • beta-Aminoethylsulphonate
  • beta-Aminoethylsulphonic acid
  • Β-aminoethylsulfonate
  • Β-aminoethylsulfonic acid
  • Β-aminoethylsulphonate
  • Β-aminoethylsulphonic acid
  • Taurine hydrochloride
  • Taurine zinc salt (2:1)
  • Taurine, monopotassium salt
  • Taufon
  • Tauphon
CAS number107-35-7
WeightAverage: 125.147
Monoisotopic: 125.014663785
InChI KeyXOAAWQZATWQOTB-UHFFFAOYSA-N
InChIInChI=1S/C2H7NO3S/c3-1-2-7(4,5)6/h1-3H2,(H,4,5,6)
IUPAC Name2-aminoethane-1-sulfonic acid
Traditional IUPAC Nametaurine
Chemical FormulaC2H7NO3S
SMILESNCCS(O)(=O)=O
Chemical Taxonomy
Description belongs to the class of organic compounds known as organosulfonic acids. Organosulfonic acids are compounds containing the sulfonic acid group, which has the general structure RS(=O)2OH (R is not a hydrogen atom).
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassOrganic sulfonic acids and derivatives
Sub ClassOrganosulfonic acids and derivatives
Direct ParentOrganosulfonic acids
Alternative Parents
Substituents
  • Alkanesulfonic acid
  • Sulfonyl
  • Organosulfonic acid
  • 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
StateSolid
Charge0
Melting point300 °C
Experimental Properties
PropertyValueReference
Water Solubility80.7 mg/mL at 20 oC [YALKOWSKY,SH & DANNENFELSER,RM (1992)]PhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility105 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity24.61 m³·mol⁻¹ChemAxon
Polarizability10.82 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • extracellular
  • cytoplasm
Organoleptic Properties
Flavour/OdourSource
BitterFDB003191
BlandFDB003191
SMPDB Pathways
Sulfur metabolismPW002483 ThumbThumb?image type=greyscaleThumb?image type=simple
Taurine and hypotaurine biosynthesisPW002480 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
Sulfur metabolismec00920 Map00920
Taurine and hypotaurine metabolismec00430 Map00430
SMPDB Reactions
Cysteic acid → Taurine + Carbon dioxide
Taurine + Oxoglutaric acid + oxygen → Sulfite + Succinic acid + Carbon dioxide + hydron + aminoacetaldehyde
KEGG Reactions
Oxoglutaric acid + Taurine + oxygen → Sulfite + Carbon dioxide + hydron + aminoacetaldehyde + Succinic acid
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)splash10-0032-1901000000-5373a9d32fa1f29b8012JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-0032-0901000000-f7cf5a7ef7741fe71454JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)splash10-00di-9802000000-c315203efd199b1871e7JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0032-1901000000-5373a9d32fa1f29b8012JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0032-0901000000-f7cf5a7ef7741fe71454JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-9802000000-c315203efd199b1871e7JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0f9t-0902000000-41e2bea3bce85bb00386JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0f9t-0902000000-41e2bea3bce85bb00386JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-000x-9000000000-fc8f496bf8d00c37dd84JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableJSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-006t-0890202100-ef2de9b47cafa707f789JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-004i-9300000000-530438ccab9f22503af5JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-00di-0900000000-ad642e440d924dfd8e20JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-006t-0097000000-24cfd722ea30b6a3b22dJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-006t-0790202100-45d57f0101d4cefbc981JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-004i-9300000000-bd1f04d82f9e675f2303JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-00di-0900000000-d411fff703670832e445JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-006t-0098000000-c86b66ff71cff513520fJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-00di-0900000000-31f44189a2671cf5d2e9JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-00e9-6900000000-cc7fe1badfe13959526dJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-001i-9000000000-ae6465f92e91cfad7276JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-001i-9000000000-af0ea33a51fe79abee00JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-001i-9000000000-27d6c7ae55f73bb21b3cJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-00di-0900000000-31f44189a2671cf5d2e9JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-00e9-6900000000-cc7fe1badfe13959526dJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-001i-9000000000-ae6465f92e91cfad7276JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-001i-9000000000-af0ea33a51fe79abee00JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-001i-9000000000-27d6c7ae55f73bb21b3cJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-004i-9300000000-530438ccab9f22503af5JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-00di-0900000000-ad642e440d924dfd8e20JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-006t-0097000000-e6d9cd15ddc56b10a1c6JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-004i-9300000000-bd1f04d82f9e675f2303JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-00di-0900000000-d411fff703670832e445JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-006t-0098000000-c86b66ff71cff513520fJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - , negativesplash10-00di-4900000000-9793e5415fbc98c19205JSpectraViewer | MoNA
MSMass Spectrum (Electron Ionization)splash10-0036-9000000000-a96a1a8b53b1b556f6caJSpectraViewer | MoNA
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,1H] 2D NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableJSpectraViewer
References
References:
  • Herrgard, M. J., Swainston, N., Dobson, P., Dunn, W. B., Arga, K. Y., Arvas, M., Bluthgen, N., Borger, S., Costenoble, R., Heinemann, M., Hucka, M., Le Novere, N., Li, P., Liebermeister, W., Mo, M. L., Oliveira, A. P., Petranovic, D., Pettifer, S., Simeonidis, E., Smallbone, K., Spasic, I., Weichart, D., Brent, R., Broomhead, D. S., Westerhoff, H. V., Kirdar, B., Penttila, M., Klipp, E., Palsson, B. O., Sauer, U., Oliver, S. G., Mendes, P., Nielsen, J., Kell, D. B. (2008). "A consensus yeast metabolic network reconstruction obtained from a community approach to systems biology." Nat Biotechnol 26:1155-1160.18846089
  • Hogan, D. A., Auchtung, T. A., Hausinger, R. P. (1999). "Cloning and characterization of a sulfonate/alpha-ketoglutarate dioxygenase from Saccharomyces cerevisiae." J Bacteriol 181:5876-5879.10482536
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.
External Links:
ResourceLink
CHEBI ID15891
HMDB IDHMDB00251
Pubchem Compound ID1123
Kegg IDC00245
ChemSpider ID1091
FOODB IDFDB003191
WikipediaTaurine
BioCyc IDTAURINE

Enzymes

Protein Details
1. Alpha-ketoglutarate-dependent sulfonate dioxygenase
General function:
Involved in oxidoreductase activity
Specific function:
Acts as a alpha-ketoglutarate-dependent dioxygenase active on sulfonates. Although taurine is a poor substrate, a variety of other sulfonates are utilized, with the best natural substrates being isethionate and taurocholate
Gene Name:
JLP1
Uniprot ID:
Q12358
Molecular weight:
46982.30078
Reactions
Protein Details
2. Glutamate decarboxylase
General function:
Involved in glutamate decarboxylase activity
Specific function:
L-glutamate = 4-aminobutanoate + CO(2)
Gene Name:
GAD1
Uniprot ID:
Q04792
Molecular weight:
65989.5
Reactions
L-glutamate → 4-aminobutanoate + CO(2).