Showing metabocard for Taurine (MMDBc0000086)

Record Information
Version1.0
StatusDetected and Quantified
Creation Date2020-10-27 23:29:52 UTC
Update Date2024-09-29 09:31:21 UTC
Metabolite IDMMDBc0000086
Metabolite Identification
Common NameTaurine
DescriptionTaurine 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 including 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, neonates fed formula milk, and various disease states. Several inborn errors of taurine metabolism have been described. Perry syndrome is an unusual neuropsychiatric disorder inherited in an autosomal dominant fashion through three 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 that was 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: 168605 ). Hypertaurinuric cardiomyopathy 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 two with mitral valve prolapse, congestive cardiomyopathy eventually developed while the amounts of urinary taurine doubled (OMIM: 145350 ). 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 that 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/). Moreover, taurine is found to be associated with maple syrup urine disease, which is an inborn error of metabolism.
Structure
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for #<Metabolite:0x00007f9229ca0400>


  Mrv1652303262021222D          

  7  6  0  0  0  0            999 V2000
 9990.8842 9990.3497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9990.1699 9990.7611    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
 9991.5993 9990.7611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9990.5812 9991.4761    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9989.7563 9991.4761    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9989.4515 9990.3476    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9992.3123 9990.3497    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  1  0  0  0  0
  2  4  2  0  0  0  0
  2  5  2  0  0  0  0
  2  6  1  0  0  0  0
  3  7  1  0  0  0  0
M  END
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3D MOL for #<Metabolite:0x00007f9229ca0400>

HMDB0000251
     RDKit          3D
Taurine
 14 13  0  0  0  0  0  0  0  0999 V2000
   -2.2686   -0.4886   -0.3975 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1121    0.1191    0.2235 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1814   -0.2979   -0.4697 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5024    0.5260    0.4039 S   0  0  0  0  0  6  0  0  0  0  0  0
    1.4894    0.1368    1.8521 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2905    2.0230    0.3390 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9918    0.1674   -0.2404 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9273    0.1986   -0.8072 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7140   -1.2241    0.1640 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0377   -0.2447    1.2750 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1976    1.2282    0.1753 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3295   -1.3865   -0.3075 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1601   -0.0261   -1.5296 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3123   -0.7313   -0.0568 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  4  6  2  0
  4  7  1  0
  1  8  1  0
  1  9  1  0
  2 10  1  0
  2 11  1  0
  3 12  1  0
  3 13  1  0
  7 14  1  0
M  END
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3D SDF for #<Metabolite:0x00007f9229ca0400>


  Mrv1652303262021222D          

  7  6  0  0  0  0            999 V2000
 9990.8842 9990.3497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9990.1699 9990.7611    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
 9991.5993 9990.7611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9990.5812 9991.4761    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9989.7563 9991.4761    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9989.4515 9990.3476    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9992.3123 9990.3497    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  1  0  0  0  0
  2  4  2  0  0  0  0
  2  5  2  0  0  0  0
  2  6  1  0  0  0  0
  3  7  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0000086

> <DATABASE_NAME>
MIME

> <SMILES>
NCCS(O)(=O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C2H7NO3S/c3-1-2-7(4,5)6/h1-3H2,(H,4,5,6)

> <INCHI_KEY>
XOAAWQZATWQOTB-UHFFFAOYSA-N

> <FORMULA>
C2H7NO3S

> <MOLECULAR_WEIGHT>
125.147

> <EXACT_MASS>
125.014663785

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
14

> <JCHEM_AVERAGE_POLARIZABILITY>
10.824350988998525

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-aminoethane-1-sulfonic acid

> <ALOGPS_LOGP>
-2.19

> <JCHEM_LOGP>
-2.6146873946423876

> <ALOGPS_LOGS>
-0.08

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
-1.4937847370487942

> <JCHEM_PKA_STRONGEST_BASIC>
9.343935759428495

> <JCHEM_POLAR_SURFACE_AREA>
80.39

> <JCHEM_REFRACTIVITY>
24.605100000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.05e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
taurine

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for #<Metabolite:0x00007f9229ca0400>

HMDB0000251
     RDKit          3D
Taurine
 14 13  0  0  0  0  0  0  0  0999 V2000
   -2.2686   -0.4886   -0.3975 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1121    0.1191    0.2235 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1814   -0.2979   -0.4697 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5024    0.5260    0.4039 S   0  0  0  0  0  6  0  0  0  0  0  0
    1.4894    0.1368    1.8521 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2905    2.0230    0.3390 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9918    0.1674   -0.2404 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9273    0.1986   -0.8072 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7140   -1.2241    0.1640 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0377   -0.2447    1.2750 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1976    1.2282    0.1753 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3295   -1.3865   -0.3075 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1601   -0.0261   -1.5296 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3123   -0.7313   -0.0568 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  4  6  2  0
  4  7  1  0
  1  8  1  0
  1  9  1  0
  2 10  1  0
  2 11  1  0
  3 12  1  0
  3 13  1  0
  7 14  1  0
M  END
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PDB for #<Metabolite:0x00007f9229ca0400>

HEADER    PROTEIN                                 26-MAR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-MAR-20         0                                  
HETATM    1  C   UNK     0    8649.6508648.653   0.000  0.00  0.00           C+0
HETATM    2  S   UNK     0    8648.3178649.421   0.000  0.00  0.00           S+0
HETATM    3  C   UNK     0    8650.9858649.421   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0    8649.0858650.755   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0    8647.5458650.755   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0    8646.9768648.649   0.000  0.00  0.00           O+0
HETATM    7  N   UNK     0    8652.3168648.653   0.000  0.00  0.00           N+0
CONECT    1    2    3                                                       
CONECT    2    1    4    5    6                                             
CONECT    3    1    7                                                       
CONECT    4    2                                                            
CONECT    5    2                                                            
CONECT    6    2                                                            
CONECT    7    3                                                            
MASTER        0    0    0    0    0    0    0    0    7    0   12    0
END
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3D PDB for #<Metabolite:0x00007f9229ca0400>

COMPND    HMDB0000251
HETATM    1  N1  UNL     1      -2.269  -0.489  -0.398  1.00  0.00           N  
HETATM    2  C1  UNL     1      -1.112   0.119   0.224  1.00  0.00           C  
HETATM    3  C2  UNL     1       0.181  -0.298  -0.470  1.00  0.00           C  
HETATM    4  S1  UNL     1       1.502   0.526   0.404  1.00  0.00           S  
HETATM    5  O1  UNL     1       1.489   0.137   1.852  1.00  0.00           O  
HETATM    6  O2  UNL     1       1.291   2.023   0.339  1.00  0.00           O  
HETATM    7  O3  UNL     1       2.992   0.167  -0.240  1.00  0.00           O  
HETATM    8  H1  UNL     1      -2.927   0.199  -0.807  1.00  0.00           H  
HETATM    9  H2  UNL     1      -2.714  -1.224   0.164  1.00  0.00           H  
HETATM   10  H3  UNL     1      -1.038  -0.245   1.275  1.00  0.00           H  
HETATM   11  H4  UNL     1      -1.198   1.228   0.175  1.00  0.00           H  
HETATM   12  H5  UNL     1       0.330  -1.386  -0.308  1.00  0.00           H  
HETATM   13  H6  UNL     1       0.160  -0.026  -1.530  1.00  0.00           H  
HETATM   14  H7  UNL     1       3.312  -0.731  -0.057  1.00  0.00           H  
CONECT    1    2    8    9
CONECT    2    3   10   11
CONECT    3    4   12   13
CONECT    4    5    5    6    6
CONECT    4    7
CONECT    7   14
END
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SMILES for #<Metabolite:0x00007f9229ca0400>

NCCS(O)(=O)=O
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INCHI for #<Metabolite:0x00007f9229ca0400>

InChI=1S/C2H7NO3S/c3-1-2-7(4,5)6/h1-3H2,(H,4,5,6)
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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
Molecular FormulaC2H7NO3S
Average Mass125.147
Monoisotopic Mass125.014663785
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