Taurine (ECMDB00251) (M2MDB000106)
| Record Information | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
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| Version | 2.0 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Creation Date | 2012-05-31 10:24:56 -0600 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Update Date | 2015-09-13 12:56:07 -0600 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Secondary Accession Numbers |
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| 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 |  | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Synonyms: |
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| Chemical Formula: | C2H7NO3S | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Weight: | Average: 125.147 Monoisotopic: 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 | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| 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). | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Kingdom | Organic compounds | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Super Class | Organic acids and derivatives | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Class | Organic sulfonic acids and derivatives | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Sub Class | Organosulfonic acids and derivatives | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Direct Parent | Organosulfonic acids | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Alternative Parents | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Substituents |
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| Molecular Framework | Aliphatic acyclic compounds | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| External Descriptors |
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| Physical Properties | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| State: | Solid | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Charge: | 0 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Melting point: | 300 °C | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Experimental Properties: |
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| Predicted Properties |
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| Biological Properties | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Cellular Locations: | Cytoplasm | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Reactions: | ADP + Phosphate + 4 Hydrogen ion + Heme + Nickel(2+) + Iron chelate + Taurine + Molybdate + Magnesium + Fe3+ + Potassium + Polyamine + vitamin B12 + Sulfate + glycerol-3-phosphate + Phosphonate + D-Maltose <> Adenosine triphosphate +3 Hydrogen ion + Water Adenosine triphosphate + Water + Taurine > ADP + Hydrogen ion + Phosphate + Taurine Adenosine triphosphate + Water + Taurine > ADP + Hydrogen ion + Phosphate + Taurine alpha-Ketoglutarate + Oxygen + Taurine <> Aminoacetaldehyde + Carbon dioxide + Hydrogen ion + Sulfite + Succinic acid Cysteic acid <> Taurine + Carbon dioxide (5-L-Glutamyl)-peptide + Taurine <> Peptide + 5-L-Glutamyl-taurine Taurine + alpha-Ketoglutarate + Oxygen <> Sulfite + Aminoacetaldehyde + Succinic acid + Carbon dioxide Taurine + Adenosine triphosphate + Water > Taurine + ADP + Phosphate + Hydrogen ion Taurine + Adenosine triphosphate + Water > Taurine + ADP + Phosphate + Hydrogen ion Taurine + Oxoglutaric acid + Oxygen > Hydrogen ion + Aminoacetaldehyde + Sulfite + Succinic acid + Carbon dioxide Adenosine triphosphate + Water + Taurine > ADP + Inorganic phosphate + Taurine Adenosine triphosphate + Water + Taurine > ADP + Inorganic phosphate + Taurine Taurine + Oxoglutaric acid + Oxygen > Sulfite + Aminoacetaldehyde + Succinic acid + Carbon dioxide Cysteic acid + Cysteic acid > Taurine + Carbon dioxide Taurine + (5-L-Glutamyl)-peptide > 5-L-Glutamyl-taurine + Peptide Taurine + Oxoglutaric acid + Oxygen > Sulfite + Succinic acid + Aminoacetaldehyde + Carbon dioxide + Sulfite Taurine + Oxoglutaric acid + Oxygen > Sulfite + Succinic acid + Carbon dioxide + Hydrogen ion + Aminoacetaldehyde + Sulfite Taurine + Adenosine triphosphate + Water > Taurine + Adenosine diphosphate + Phosphate + Hydrogen ion + ADP Taurine + Adenosine triphosphate + Water > Taurine + Adenosine diphosphate + Phosphate + Hydrogen ion + ADP alpha-Ketoglutarate + Oxygen + Taurine <> Aminoacetaldehyde + Carbon dioxide + Hydrogen ion + Sulfite + Succinic acid Taurine + alpha-Ketoglutarate + Oxygen <> Sulfite + Aminoacetaldehyde + Succinic acid + Carbon dioxide alpha-Ketoglutarate + Oxygen + Taurine <> Aminoacetaldehyde + Carbon dioxide + Hydrogen ion + Sulfite + Succinic acid | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| SMPDB Pathways: |
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| KEGG Pathways: | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| EcoCyc Pathways: |
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| Concentrations | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Not Available | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Spectra | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Spectra: | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| References | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| References: |
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| 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) | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Links | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| External Links: |
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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
- Uniprot ID:
- P18956
- Molecular weight:
- 61768
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
- Uniprot ID:
- P37610
- Molecular weight:
- 32409
Reactions
| Taurine + 2-oxoglutarate + O(2) = sulfite + aminoacetaldehyde + succinate + 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:
- 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). |
- 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
- Uniprot ID:
- Q47539
- Molecular weight:
- 29812
- 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
- Uniprot ID:
- Q47538
- Molecular weight:
- 28297
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
- Uniprot ID:
- Q47537
- Molecular weight:
- 34266
Transporters
- General function:
- Involved in transporter activity
- Specific function:
- Proton symporter that senses osmotic shifts and responds by importing osmolytes such as proline, glycine betaine, stachydrine, pipecolic acid, ectoine and taurine. It is both an osmosensor and an osmoregulator which is available to participate early in the bacterial osmoregulatory response
- Gene Name:
- proP
- Uniprot ID:
- P0C0L7
- Molecular weight:
- 54845
- 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
- Uniprot ID:
- Q47539
- Molecular weight:
- 29812
- General function:
- Involved in transporter activity
- Specific function:
- Non-specific porin
- Gene Name:
- ompN
- Uniprot ID:
- P77747
- Molecular weight:
- 41220
- General function:
- Involved in transporter activity
- Specific function:
- Uptake of inorganic phosphate, phosphorylated compounds, and some other negatively charged solutes
- Gene Name:
- phoE
- Uniprot ID:
- P02932
- Molecular weight:
- 38922
- General function:
- Involved in transporter activity
- Specific function:
- OmpF is a porin that forms passive diffusion pores which allow small molecular weight hydrophilic materials across the outer membrane. It is also a receptor for the bacteriophage T2
- Gene Name:
- ompF
- Uniprot ID:
- P02931
- Molecular weight:
- 39333
- 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
- Uniprot ID:
- Q47538
- Molecular weight:
- 28297
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
- Uniprot ID:
- Q47537
- Molecular weight:
- 34266
- General function:
- Involved in transporter activity
- Specific function:
- Forms passive diffusion pores which allow small molecular weight hydrophilic materials across the outer membrane
- Gene Name:
- ompC
- Uniprot ID:
- P06996
- Molecular weight:
- 40368