Showing metabocard for N-Acetyltaurine (MMDBc0000716)

Record Information
Version1.0
StatusDetected and Quantified
Creation Date2020-12-10 18:53:24 UTC
Update Date2024-04-30 19:33:36 UTC
Metabolite IDMMDBc0000716
Metabolite Identification
Common NameN-Acetyltaurine
DescriptionN-Acetyltaurine (also known as NAT) is a highly water-soluble and hygroscopic compound formed by the acetylation of taurine. It is both an endogenous metabolite that is constitutively synthesized in the body and an exogenous metabolite formed by ethanol metabolism. NAT is formed by one or multiple N-acetylation reactions between taurine and ethanol metabolites (primarily acetate). The enzyme responsible for NAT synthesis is called NAT synthase, a cytosolic metalloenzyme located in the kidney and liver that can directly catalyze the esterification reaction between taurine and acetate, without the involvement of ATP and CoA. NAT is a potential biomarker of hyperacetatemia as well as ethanol consumption (PMID: 22228769 ). NAT is typically found in human urine with normal concentrations of 0.599-1.38 umol/mmol creatinine in alcohol-abstinent subjects. NAT can reach average levels of 8.38 umol/mmol creatinine (range 5.39-10.47 umol/mmol creatinine) in subjects consuming alcohol within 3 to 6 h after the start of drinking. Positive NAT results can be used as an indicator for recent alcohol consumption (PMID: 27520321 ). NAT is considered a direct alcohol biomarker that specifically represents the oxidative pathway of ethanol metabolism. Other direct alcohol biomarkers such as fatty acid ethyl esters (FAEE), ethyl glucuronide, ethyl sulfate, and phosphatidylethanol reflect the non-oxidative pathway of alcohol metabolism. NAT is also elevated in urine after periods of endurance exercise. NAT was previously found in nature as a major component in the sticky droplet of orb spider web. Due to its high hygroscopicity, N-acetyltaurine appears to ensure the orb spider’s web flexibility.
Structure
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for #<Metabolite:0x00007fdb596763d0>


  Mrv1652312111719142D          

 10  9  0  0  0  0            999 V2000
 2498.6690 2498.7642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2499.3836 2499.1758    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2500.0984 2498.7642    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 2500.8132 2499.1758    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2501.5282 2498.7642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2500.8132 2500.0011    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2497.9540 2499.1758    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
 2497.5403 2499.8926    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2498.3658 2499.8926    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2497.2351 2498.7621    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  7  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  2  0  0  0  0
  7  8  2  0  0  0  0
  7  9  2  0  0  0  0
  7 10  1  0  0  0  0
M  END
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3D MOL for #<Metabolite:0x00007fdb596763d0>

HMDB0240253
     RDKit          3D
N-Acetyltaurine
 19 18  0  0  0  0  0  0  0  0999 V2000
    3.1565    0.8073    0.0628 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1254   -0.2198    0.2986 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3978   -1.2480    0.9598 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8225   -0.0584   -0.2160 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1533   -1.0801    0.0349 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5080   -0.8272   -0.5396 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1912    0.6621    0.1427 S   0  0  0  0  0  6  0  0  0  0  0  0
   -1.3201    1.8460   -0.0545 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4087    0.4020    1.6183 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7352    0.9468   -0.5109 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5541    0.7613   -0.9913 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6907    1.8220    0.2348 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9971    0.7480    0.7773 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6053    0.7860   -0.7610 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2792   -2.0311   -0.3915 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1808   -1.2254    1.1470 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5436   -0.8519   -1.6314 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1917   -1.6543   -0.1883 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3959    0.4147    0.0084 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  7  9  2  0
  7 10  1  0
  1 11  1  0
  1 12  1  0
  1 13  1  0
  4 14  1  0
  5 15  1  0
  5 16  1  0
  6 17  1  0
  6 18  1  0
 10 19  1  0
M  END
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3D SDF for #<Metabolite:0x00007fdb596763d0>


  Mrv1652312111719142D          

 10  9  0  0  0  0            999 V2000
 2498.6690 2498.7642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2499.3836 2499.1758    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2500.0984 2498.7642    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 2500.8132 2499.1758    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2501.5282 2498.7642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2500.8132 2500.0011    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2497.9540 2499.1758    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
 2497.5403 2499.8926    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2498.3658 2499.8926    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2497.2351 2498.7621    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  7  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  2  0  0  0  0
  7  8  2  0  0  0  0
  7  9  2  0  0  0  0
  7 10  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0000716

> <DATABASE_NAME>
MIME

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

> <INCHI_IDENTIFIER>
InChI=1S/C4H9NO4S/c1-4(6)5-2-3-10(7,8)9/h2-3H2,1H3,(H,5,6)(H,7,8,9)

> <INCHI_KEY>
CXJAAWRLVGAKDV-UHFFFAOYSA-N

> <FORMULA>
C4H9NO4S

> <MOLECULAR_WEIGHT>
167.18

> <EXACT_MASS>
167.025228948

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
19

> <JCHEM_AVERAGE_POLARIZABILITY>
15.006627332279146

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
-1.94

> <JCHEM_LOGP>
-2.9325552482268433

> <ALOGPS_LOGS>
-0.80

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
14.939475088402919

> <JCHEM_PKA_STRONGEST_ACIDIC>
-1.031482931108826

> <JCHEM_PKA_STRONGEST_BASIC>
-1.7007132426937215

> <JCHEM_POLAR_SURFACE_AREA>
83.47

> <JCHEM_REFRACTIVITY>
34.0489

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.64e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-acetamidoethanesulfonic acid

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for #<Metabolite:0x00007fdb596763d0>

HMDB0240253
     RDKit          3D
N-Acetyltaurine
 19 18  0  0  0  0  0  0  0  0999 V2000
    3.1565    0.8073    0.0628 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1254   -0.2198    0.2986 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3978   -1.2480    0.9598 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8225   -0.0584   -0.2160 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1533   -1.0801    0.0349 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5080   -0.8272   -0.5396 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1912    0.6621    0.1427 S   0  0  0  0  0  6  0  0  0  0  0  0
   -1.3201    1.8460   -0.0545 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4087    0.4020    1.6183 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7352    0.9468   -0.5109 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5541    0.7613   -0.9913 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6907    1.8220    0.2348 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9971    0.7480    0.7773 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6053    0.7860   -0.7610 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2792   -2.0311   -0.3915 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1808   -1.2254    1.1470 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5436   -0.8519   -1.6314 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1917   -1.6543   -0.1883 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3959    0.4147    0.0084 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  7  9  2  0
  7 10  1  0
  1 11  1  0
  1 12  1  0
  1 13  1  0
  4 14  1  0
  5 15  1  0
  5 16  1  0
  6 17  1  0
  6 18  1  0
 10 19  1  0
M  END
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PDB for #<Metabolite:0x00007fdb596763d0>

HEADER    PROTEIN                                 11-DEC-17   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-DEC-17         0                                  
HETATM    1  C   UNK     0    4664.1824664.360   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    4665.5164665.128   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0    4666.8504664.360   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0    4668.1854665.128   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0    4669.5194664.360   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0    4668.1854666.669   0.000  0.00  0.00           O+0
HETATM    7  S   UNK     0    4662.8474665.128   0.000  0.00  0.00           S+0
HETATM    8  O   UNK     0    4662.0754666.466   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0    4663.6164666.466   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0    4661.5054664.356   0.000  0.00  0.00           O+0
CONECT    1    2    7                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4                                                            
CONECT    7    1    8    9   10                                             
CONECT    8    7                                                            
CONECT    9    7                                                            
CONECT   10    7                                                            
MASTER        0    0    0    0    0    0    0    0   10    0   18    0
END
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3D PDB for #<Metabolite:0x00007fdb596763d0>

COMPND    HMDB0240253
HETATM    1  C1  UNL     1       3.157   0.807   0.063  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.125  -0.220   0.299  1.00  0.00           C  
HETATM    3  O1  UNL     1       2.398  -1.248   0.960  1.00  0.00           O  
HETATM    4  N1  UNL     1       0.822  -0.058  -0.216  1.00  0.00           N  
HETATM    5  C3  UNL     1      -0.153  -1.080   0.035  1.00  0.00           C  
HETATM    6  C4  UNL     1      -1.508  -0.827  -0.540  1.00  0.00           C  
HETATM    7  S1  UNL     1      -2.191   0.662   0.143  1.00  0.00           S  
HETATM    8  O2  UNL     1      -1.320   1.846  -0.054  1.00  0.00           O  
HETATM    9  O3  UNL     1      -2.409   0.402   1.618  1.00  0.00           O  
HETATM   10  O4  UNL     1      -3.735   0.947  -0.511  1.00  0.00           O  
HETATM   11  H1  UNL     1       3.554   0.761  -0.991  1.00  0.00           H  
HETATM   12  H2  UNL     1       2.691   1.822   0.235  1.00  0.00           H  
HETATM   13  H3  UNL     1       3.997   0.748   0.777  1.00  0.00           H  
HETATM   14  H4  UNL     1       0.605   0.786  -0.761  1.00  0.00           H  
HETATM   15  H5  UNL     1       0.279  -2.031  -0.391  1.00  0.00           H  
HETATM   16  H6  UNL     1      -0.181  -1.225   1.147  1.00  0.00           H  
HETATM   17  H7  UNL     1      -1.544  -0.852  -1.631  1.00  0.00           H  
HETATM   18  H8  UNL     1      -2.192  -1.654  -0.188  1.00  0.00           H  
HETATM   19  H9  UNL     1      -4.396   0.415   0.008  1.00  0.00           H  
CONECT    1    2   11   12   13
CONECT    2    3    3    4
CONECT    4    5   14
CONECT    5    6   15   16
CONECT    6    7   17   18
CONECT    7    8    8    9    9
CONECT    7   10
CONECT   10   19
END
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SMILES for #<Metabolite:0x00007fdb596763d0>

CC(=O)NCCS(O)(=O)=O
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INCHI for #<Metabolite:0x00007fdb596763d0>

InChI=1S/C4H9NO4S/c1-4(6)5-2-3-10(7,8)9/h2-3H2,1H3,(H,5,6)(H,7,8,9)
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Synonyms
ValueSource
2-Acetamidoethanesulfonic acidChEBI
N-AcetyltaurineChEBI
2-AcetamidoethanesulfonateGenerator
2-AcetamidoethanesulphonateGenerator
2-Acetamidoethanesulphonic acidGenerator
NATHMDB
AcetyltaurineChEBI, HMDB
2-(Acetylamino)ethanesulfonic acidHMDB
[2-Acetylamino]ethanesulfonic acidHMDB
Magnesium acetyltaurinateMeSH, HMDB
ATaMgMeSH, HMDB
AcetyltaurinateMeSH, HMDB
Magnesium acetyltaurateMeSH, HMDB
NAcTHMDB
Molecular FormulaC4H9NO4S
Average Mass167.18
Monoisotopic Mass167.025228948
IUPAC Name2-acetamidoethane-1-sulfonic acid
Traditional Name2-acetamidoethanesulfonic acid
CAS Registry NumberNot Available
SMILES
CC(=O)NCCS(O)(=O)=O
InChI Identifier
InChI=1S/C4H9NO4S/c1-4(6)5-2-3-10(7,8)9/h2-3H2,1H3,(H,5,6)(H,7,8,9)
InChI KeyCXJAAWRLVGAKDV-UHFFFAOYSA-N