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Bovine Rumen Metabolome Database



Showing metabocard for Taurine (RMDB00251)

Legend: metabolite field enzyme field

Version 1.0
Creation Date 2005-11-16 15:48:42
Update Date 2009-07-07 14:32:49
Accession Number RMDB00251
Common 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. Yet taurine is an essential amino acid in pre-term and newborn infants of humans and many other species. Adults can synthesize their own taurine, yet are probably dependent in part on dietary taurine. Taurine is abundant in the brain, heart, breast, gallbladder and kidney and has important roles in health and disease in these organs. Taurine has many diverse biological functions serving as a neurotransmitter in the brain, a stabilizer of cell membranes and a facilitator in the transport of ions such as sodium, potassium, calcium and magnesium. Taurine is highly concentrated in animal and fish protein, which are good sources of dietary taurine. It can be synthesized by the body from cysteine when vitamin B6 is present. Deficiency of taurine occurs in premature infants and neonates fed formula milk, and in various disease states. Inborn errors of taurine metabolism have been described. OMIM 168605, an unusual neuropsychiatric disorder inherited in an autosomal dominant fashion through 3 generations of a family. Symptoms began late in the fifth decade in 6 affected persons and death occurred after 4 to 6 years. The earliest and most prominent symptom was mental depression not responsive to antidepressant drugs or electroconvulsive therapy. Sleep disturbances, exhaustion and marked weight loss were features. Parkinsonism developed later, and respiratory failure occurred terminally. OMIM 145350 describes congestive cardiomyopathy and markedly elevated urinary taurine levels (about 5 times normal). Other family members had late or holosystolic mitral valve prolapse and elevated urinary taurine values (about 2.5 times normal). In 2 with mitral valve prolapse, congestive cardiomyopathy eventually developed while the amounts of urinary taurine doubled. Taurine, after GABA, is the second most important inhibitory neurotransmitter in the brain. Its inhibitory effect is one source of taurine's anticonvulsant and antianxiety properties. It also lowers glutamic acid in the brain, and preliminary clinical trials suggest taurine may be useful in some forms of epilepsy. Taurine in the brain is usually associated with zinc or manganese. The amino acids alanine and glutamic acid, as well as pantothenic acid, inhibit taurine metabolism while vitamins A and B6, zinc and manganese help build taurine. Cysteine and B6 are the nutrients most directly involved in taurine synthesis. Taurine levels have been found to decrease significantly in many depressed patients. One reason that the findings are not entirely clear is because taurine is often elevated in the blood of epileptics who need it. It is often difficult to distinguish compensatory changes in human biochemistry from true metabolic or deficiency disease. Low levels of taurine are found in retinitis pigmentosa. Taurine deficiency in experimental animals produces degeneration of light-sensitive cells. Therapeutic applications of taurine to eye disease are likely to be forthcoming. Taurine has many important metabolic roles. Supplements can stimulate prolactin and insulin release. The parathyroid gland makes a peptide hormone called glutataurine (glutamic acid-taurine), which further demonstrates taurine's role in endocrinology. Taurine increases bilirubin and cholesterol excretion in bile, critical to normal gallbladder function. It seems to inhibit the effect of morphine and potentiates the effects of opiate antagonists. Low plasma taurine levels have been found in a variety of conditions, i.e., depression, hypertension, hypothyroidism, gout, institutionalized patients, infertility, obesity, kidney failure and others. (http://www.dcnutrition.com/AminoAcids/)
Synonyms
  1. 1-Aminoethane-2-sulfonate
  2. 1-Aminoethane-2-sulfonic acid
  3. 2-Aminoethanesulfonate
  4. 2-Aminoethanesulfonic acid
  5. 2-Aminoethylsulfonate
  6. 2-Aminoethylsulfonic acid
  7. 2-Sulfoethylamine
  8. Aminoethylsulfonate
  9. Aminoethylsulfonic acid
  10. Taurine
  11. b-Aminoethylsulfonate
  12. b-Aminoethylsulfonic acid
  13. beta-Aminoethylsulfonate
  14. beta-Aminoethylsulfonic acid
Chemical IUPAC Name 2-amino-Ethanesulfonic acid
Chemical Formula C2H7NO3S
Chemical Structure Structure
Chemical Taxonomy
Kingdom
  • Organic
Super Class
  • Amino acids and Amino Acid conjugates
Class
  • Amino Acids
Sub Class
  • NA
Family
  • Mammalian_Metabolite
Species
  • primary amine; primary aliphatic amine (alkylamine); sulfonic acid
Biofunction
  • Osmolyte; Essential amino acid; Protein component; Component of Taurine and hypotaurine metabolism
Application
Source
  • Endogenous
Average Molecular Weight 125.147
Monoisotopic Molecular Weight 125.014664
Isomeric SMILES NCCS(O)(=O)=O
Canonical SMILES NCCS(O)(=O)=O
KEGG Compound ID C00245 Link Image
BioCyc ID Not Available
BiGG ID 34373 Link Image
Wikipedia Link Taurine Link Image
METLIN ID 31 Link Image
PubChem Compound 1123 Link Image
PubChem Substance 11113407 Link Image
ChEBI ID 15891 Link Image
CAS Registry Number 107-35-7
InChI Identifier InChI=1/C2H7NO3S/c3-1-2-7(4,5)6/h1-3H2,(H,4,5,6)
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.
Melting Point (Experimental) 300 oC
Experimental Water Solubility 80.7 mg/mL [YALKOWSKY,SH & DANNENFELSER,RM (1992)] Source: PhysProp
Predicted Water Solubility 104.99999 mg/mL [Predicted by ALOGPS] Calculated using ALOGPS
Physiological Charge 0
State Solid
Experimental LogP/Hydrophobicity Not Available Source: PhysProp
Predicted LogP/Hydrophobicity -2.19 [Predicted by ALOGPS]; -1.7 [Predicted by PubChem via XLOGP]; -3.36 [MEYLAN,WM & HOWARD,PH (1995)] Calculated using ALOGPS
Material Safety Data Sheet (MSDS)
MOL File Show Link Image
SDF File Show Link Image
PDB File Show Link Image
2D Structure
3D Structure
Experimental PDB ID 1GY9 Link Image
Experimental PDB File Show
Experimental PDB Structure
Experimental 1H NMR Spectrum Not Available
Experimental 13C NMR Spectrum Not Available
Experimental 13C HSQC Spectrum Not Available
Predicted 1H NMR Spectrum Show Image
Show Peaklist
Predicted 13C NMR Spectrum Show Image
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Mass Spectrum
Low Energy
Download File
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Medium Energy
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High Energy
Download File
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Simplified TOCSY Spectrum Not Available
BMRB Spectrum Not Available
Cellular Location
  • Cytoplasm (Predicted from LogP)
  • Extracellular
  • peroxisome
Biofluid Location
  • Cow_Milk
  • Rumen
Tissue Location
Concentrations (Normal)
Biofluid Rumen
Value 36.2 +/- 0.01 uM
Age N/A
Sex N/A
Condition Normal
Breed Not Available
Experimental Condition Not Available
Comments Not Available
References
  • The rumen metabolome (in preparation)
Concentrations (Abnormal) Not Available
Pathway Names Not Available
HMDB Pathways Not Available
KEGG Pathways Not Available
SimCell Pathways Not Available
General References
  1. Wikipedia Link Image