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Record Information
Version1.0
Creation Date2016-09-30 22:27:25 UTC
Update Date2020-06-04 20:32:44 UTC
BMDB IDBMDB0000251
Secondary Accession Numbers
  • BMDB00251
Metabolite Identification
Common NameTaurine
DescriptionTaurine, also known as taufon or 2-sulfoethylamine, 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 exists as a solid, possibly soluble (in water), and a very strong basic compound (based on its pKa) molecule. Taurine exists in all living species, ranging from bacteria to humans. Taurine is a potentially toxic compound. Taurine has been found to be associated with several diseases known as perillyl alcohol administration for cancer treatment, schizophrenia, irritable bowel syndrome, and sulfite oxidase deficiency, isolated; also taurine has been linked to the inborn metabolic disorders including maple syrup urine disease.
Structure
Thumb
Synonyms
ValueSource
2-Aminoethanesulfonic acidChEBI
2-Aminoethyl sulfonateChEBI
Aminoethylsulfonic acidChEBI
beta-Aminoethylsulfonic acidChEBI
2-AminoethanesulfonateGenerator
2-AminoethanesulphonateGenerator
2-Aminoethanesulphonic acidGenerator
2-Aminoethyl sulfonic acidGenerator
2-Aminoethyl sulphonateGenerator
2-Aminoethyl sulphonic acidGenerator
AminoethylsulfonateGenerator
AminoethylsulphonateGenerator
Aminoethylsulphonic acidGenerator
b-AminoethylsulfonateGenerator
b-Aminoethylsulfonic acidGenerator
b-AminoethylsulphonateGenerator
b-Aminoethylsulphonic acidGenerator
beta-AminoethylsulfonateGenerator
beta-AminoethylsulphonateGenerator
beta-Aminoethylsulphonic acidGenerator
Β-aminoethylsulfonateGenerator
Β-aminoethylsulfonic acidGenerator
Β-aminoethylsulphonateGenerator
Β-aminoethylsulphonic acidGenerator
1-Aminoethane-2-sulfonateHMDB
1-Aminoethane-2-sulfonic acidHMDB
2-AminoethylsulfonateHMDB
2-Aminoethylsulfonic acidHMDB
2-SulfoethylamineHMDB
Taurine hydrochlorideHMDB
Taurine zinc salt (2:1)HMDB
Taurine, monopotassium saltHMDB
TaufonHMDB
TauphonHMDB
Chemical FormulaC2H7NO3S
Average Molecular Weight125.147
Monoisotopic Molecular Weight125.014663785
IUPAC Name2-aminoethane-1-sulfonic acid
Traditional Nametaurine
CAS Registry Number107-35-7
SMILES
NCCS(O)(=O)=O
InChI Identifier
InChI=1S/C2H7NO3S/c3-1-2-7(4,5)6/h1-3H2,(H,4,5,6)
InChI KeyXOAAWQZATWQOTB-UHFFFAOYSA-N
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
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Peroxisome
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point300 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility80.7 mg/mLNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
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) (Non-derivatized)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-EI-TOF (Non-derivatized)splash10-0032-1901000000-5373a9d32fa1f29b8012View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0032-0901000000-f7cf5a7ef7741fe71454View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-9802000000-c315203efd199b1871e7View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0f9t-0902000000-41e2bea3bce85bb00386View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0f9t-0902000000-41e2bea3bce85bb00386View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-000x-9000000000-fc8f496bf8d00c37dd84View in MoNA
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 AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,1H] 2D NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Peroxisome
Biospecimen Locations
  • Blood
  • Brain
  • Epidermis
  • Erythrocyte
  • Fibroblasts
  • Intestine
  • Kidney
  • Leukocyte
  • Liver
  • Longissimus Thoracis Muscle
  • Mammary Gland
  • Milk
  • Neuron
  • Pancreas
  • Placenta
  • Platelet
  • Prostate Tissue
  • Retina
  • Ruminal Fluid
  • Semimembranosus Muscle
  • Testis
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified80 +/- 20 uMNot SpecifiedNot Specified
Normal
    • Aidin Foroutan, C...
details
BloodDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
BloodDetected and Quantified33-41 uMNot SpecifiedNot Specified
Normal
details
BloodDetected and Quantified33-47 uMNot SpecifiedNot Specified
Normal
details
BrainExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
EpidermisExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
ErythrocyteExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
FibroblastsExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
IntestineExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
KidneyExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
LeukocyteExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
LiverDetected and Quantified2243 +/- 1186 nmol/g of tissueNot SpecifiedNot Specified
Normal
    • Aidin Foroutan, C...
details
LiverDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
Longissimus Thoracis MuscleDetected and Quantified480 +/- 146 nmol/g of tissueNot SpecifiedNot Specified
Normal
    • Aidin Foroutan, C...
details
Mammary GlandDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
Mammary GlandDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified10 - 30 uMNot SpecifiedNot Specified
Normal
    • NRC. 1989. Recomm...
details
MilkDetected and Quantified327 - 621 uMNot SpecifiedNot SpecifiedNormal details
MilkDetected and Quantified37 +/- 2 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified41 +/- 2 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified38 +/- 2 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified37 +/- 2 uMNot SpecifiedNot Specified
Normal
details
NeuronExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
PancreasExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
PlacentaExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
PlateletExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
Prostate TissueExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
RetinaExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
Ruminal FluidDetected and Quantified8 +/- 7 uMNot SpecifiedNot Specified
Normal
    • Aidin Foroutan, C...
details
Ruminal FluidDetected and Quantified1.07 +/- 0.007 uMNot SpecifiedNot Specified
Normal
    • Fozia Saleem, Sou...
details
Ruminal FluidDetected and Quantified36.2 +/- 0.01 uMNot SpecifiedNot SpecifiedNormal
    • Fozia Saleem, Sou...
details
Semimembranosus MuscleDetected and Quantified844 +/- 301 nmol/g of tissueNot SpecifiedNot Specified
Normal
    • Aidin Foroutan, C...
details
TestisDetected and Quantified1510 +/- 296 nmol/g of tissueNot SpecifiedNot Specified
Normal
    • Aidin Foroutan, C...
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
All Mycobacterium avium subsp. paratuberculosis-infected
details
BloodDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
High dose Mycobacterium avium subsp. paratuberculosis-infected
details
BloodDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Low dose Mycobacterium avium subsp. paratuberculosis-infected
details
BloodDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Mycobacterium avium subsp. paratuberculosis infection
details
HMDB IDHMDB0000251
DrugBank IDDB01956
Phenol Explorer Compound IDNot Available
FooDB IDFDB003191
KNApSAcK IDC00048188
Chemspider ID1091
KEGG Compound IDC00245
BioCyc IDTAURINE
BiGG ID34373
Wikipedia LinkTaurine
METLIN ID31
PubChem Compound1123
PDB IDNot Available
ChEBI ID15891
References
Synthesis ReferenceHu, 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)Not Available
General References
  1. Klein MS, Almstetter MF, Schlamberger G, Nurnberger N, Dettmer K, Oefner PJ, Meyer HH, Wiedemann S, Gronwald W: Nuclear magnetic resonance and mass spectrometry-based milk metabolomics in dairy cows during early and late lactation. J Dairy Sci. 2010 Apr;93(4):1539-50. doi: 10.3168/jds.2009-2563. [PubMed:20338431 ]
  2. Mung D, Li L: Development of Chemical Isotope Labeling LC-MS for Milk Metabolomics: Comprehensive and Quantitative Profiling of the Amine/Phenol Submetabolome. Anal Chem. 2017 Apr 18;89(8):4435-4443. doi: 10.1021/acs.analchem.6b03737. Epub 2017 Mar 28. [PubMed:28306241 ]
  3. Mung D, Li L: Applying quantitative metabolomics based on chemical isotope labeling LC-MS for detecting potential milk adulterant in human milk. Anal Chim Acta. 2018 Feb 25;1001:78-85. doi: 10.1016/j.aca.2017.11.019. Epub 2017 Nov 14. [PubMed:29291809 ]
  4. NA (1989). NRC. 1989. Recommended Dietary Allowances. 10th ed. Natl. Acad. Press, Washington, DC.. The National Academies Press.
  5. A. Foroutan et al. (2019). A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation). Journal of Agricultural and Food Chemistry.

Enzymes

General function:
Amino acid transport and metabolism
Specific function:
Catalyzes the production of GABA.
Gene Name:
GAD1
Uniprot ID:
Q0VCA1
Molecular weight:
66784.0
Reactions
Cysteic acid → Taurine + Carbon dioxidedetails
General function:
Amino acid transport and metabolism
Specific function:
Catalyzes the decarboxylation of L-aspartate, 3-sulfino-L-alanine (cysteine sulfinic acid), and L-cysteate to beta-alanine, hypotaurine and taurine, respectively. The preferred substrate is L-aspartate. Does not exhibit any decarboxylation activity toward glutamate.
Gene Name:
GADL1
Uniprot ID:
A6QM00
Molecular weight:
59380.0
Reactions
Cysteic acid → Taurine + Carbon dioxidedetails
General function:
Involved in chloride ion binding
Specific function:
Glycine receptors are ligand-gated chloride channels. Channel opening is triggered by extracellular glycine. Channel opening is also triggered by taurine and beta-alanine. Channel characteristics depend on the subunit composition; heteropentameric channels are activated by lower glycine levels and display faster desensitization (By similarity). Plays an important role in the down-regulation of neuronal excitability (PubMed:11178872). Contributes to the generation of inhibitory postsynaptic currents. Channel activity is potentiated by ethanol (By similarity). Potentiation of channel activity by intoxicating levels of ethanol contribute to the sedative effects of ethanol (By similarity).
Gene Name:
GLRA1
Uniprot ID:
P57695
Molecular weight:
52614.0
General function:
Involved in taurine:sodium symporter activity
Specific function:
Sodium-dependent taurine and beta-alanine transporter.
Gene Name:
SLC6A6
Uniprot ID:
Q9MZ34
Molecular weight:
69751.0
General function:
Not Available
Specific function:
Cleaves glutathione conjugates.
Gene Name:
GGT6
Uniprot ID:
A7YWM1
Molecular weight:
49626.0
Reactions
Taurine + A (5-L-glutamyl)-peptide → 5-L-Glutamyl-taurine + Peptidedetails