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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References transporters (1) Show 1 protein XML

Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2006-05-22 15:12:28 UTC

Update Date

2022-03-07 02:49:17 UTC

HMDB ID

HMDB0003045

Secondary Accession Numbers

HMDB03045

Metabolite Identification

Common Name

Ergothioneine

Description

Ergothioneine is a naturally occurring metabolite of histidine that has antioxidant properties. -- Pubchem. Ergothioneine is a product of plant origin that accumulates in animal tissues. Ergothioneine is biosynthesized exclusively by fungi and mycobacteria and is captured by plants through their roots. As an ingredient of human food, ET is distributed very unevenly. By far, the highest levels of Ergothioneine have been found in mushrooms (0.1-1 mg/g dried material). Ergothioneine is rapidly cleared from the circulation and then avidly retained with minimal metabolism: the whole-body half-life of ingested Ergothioneine in rats is 1 month. The content of Ergothioneine varies greatly among tissues and is strongly dependent on its dietary level. In addition to erythrocytes and bone marrow, high Ergothioneine levels have also been found in seminal fluid. The precise physiological role of ET has remained elusive since its discovery in 1909. It is known that Ergothioneine is a powerful scavenger of hydroxyl radicals and an inhibitor of iron or copper ion-dependent generation of hydroxyl radicals from hydrogen peroxide (H2O2). A specific ergothioneine transporter has recently been identified (gene symbol SLC22A4 - PMID: 15795384 ). Ergothioneine appears to play a pivotal protective role in monocytes, because the occurrence of rheumatoid arthritis and Crohn's disease has very recently been linked to variant ergothioneine transporter genes (PMID: 15795384 ). SLC22A4 is highly expressed in the kidney, where it is thought to aid in active secretion of organic cations, and may facilitate the active reabsorption of ergothioneine.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HMDB0003045
     RDKit          3D
Ergothioneine
 30 30  0  0  0  0  0  0  0  0999 V2000
   -2.3288   -1.6009    0.1806 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7556   -0.3029   -0.1457 N   0  0  0  0  0  4  0  0  0  0  0  0
   -2.5073    0.7076    0.5765 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9828   -0.0753   -1.5566 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3438   -0.2655    0.1935 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4828    0.3905   -0.8594 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9085    0.3883   -0.4624 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8205   -0.6679   -0.6580 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9990   -0.2589   -0.2004 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8941    0.9781    0.2684 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0595    1.9039    0.9298 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.5962    1.3834    0.1065 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1215    0.2014    1.5672 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3827    1.2936    1.9173 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4913   -0.6168    2.6676 O   0  0  0  0  0  1  0  0  0  0  0  0
   -1.4890   -2.2936    0.4806 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8083   -2.0799   -0.6839 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9891   -1.5543    1.0703 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1661    1.7276    0.3684 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5925    0.4709    1.6575 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5560    0.6435    0.1798 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6956    0.9455   -1.8498 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0775   -0.2066   -1.7223 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4971   -0.8593   -2.1865 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0065   -1.3529    0.1863 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4269   -0.2330   -1.7801 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1425    1.4227   -1.1051 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5492   -1.6205   -1.1070 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8972   -0.8030   -0.1942 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2498    2.3345    0.3839 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  2  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
  5 13  1  0
 13 14  2  0
 13 15  1  0
 12  7  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  3 19  1  0
  3 20  1  0
  3 21  1  0
  4 22  1  0
  4 23  1  0
  4 24  1  0
  5 25  1  1
  6 26  1  0
  6 27  1  0
  8 28  1  0
  9 29  1  0
 12 30  1  0
M  CHG  2   2   1  15  -1
M  END


  Mrv1652310301918472D          

 15 15  0  0  0  0            999 V2000
10001.067210000.2586    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10000.352110000.6700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.510310000.5149    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
10001.0672 9999.4319    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
10001.7845 9999.0175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.3500 9999.0175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.0672 9998.4532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.784510000.6700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.499610000.2586    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
10001.784510001.4967    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.963510000.7524    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9998.296110000.2674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.5510 9999.4828    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9999.3760 9999.4828    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.630910000.2674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  4  1  1  0  0  0
  1  8  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  4  7  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  2  0  0  0  0
 14 15  2  0  0  0  0
 11 12  1  0  0  0  0
 11 15  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
  2 15  1  0  0  0  0
 12  3  2  0  0  0  0
M  CHG  2   4   1   9  -1
M  END
> <DATABASE_ID>
HMDB0003045

> <DATABASE_NAME>
hmdb

> <SMILES>
C[N+](C)(C)[C@@H](CC1=CNC(=S)N1)C([O-])=O

> <INCHI_IDENTIFIER>
InChI=1S/C9H15N3O2S/c1-12(2,3)7(8(13)14)4-6-5-10-9(15)11-6/h5,7H,4H2,1-3H3,(H2-,10,11,13,14,15)/t7-/m0/s1

> <INCHI_KEY>
SSISHJJTAXXQAX-ZETCQYMHSA-N

> <FORMULA>
C9H15N3O2S

> <MOLECULAR_WEIGHT>
229.299

> <EXACT_MASS>
229.088497429

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
30

> <JCHEM_AVERAGE_POLARIZABILITY>
23.498800549659087

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
{5-[(2S)-2-carboxy-2-(trimethylazaniumyl)ethyl]-1H-imidazol-2-yl}sulfanide

> <ALOGPS_LOGP>
-1.72

> <JCHEM_LOGP>
-4.047872099397327

> <ALOGPS_LOGS>
-3.68

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
7.852522464253925

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.884701843879959

> <JCHEM_PKA_STRONGEST_BASIC>
5.311255391075792

> <JCHEM_POLAR_SURFACE_AREA>
65.98

> <JCHEM_REFRACTIVITY>
68.6873

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.94e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
ergothioneine

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0003045
     RDKit          3D
Ergothioneine
 30 30  0  0  0  0  0  0  0  0999 V2000
   -2.3288   -1.6009    0.1806 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7556   -0.3029   -0.1457 N   0  0  0  0  0  4  0  0  0  0  0  0
   -2.5073    0.7076    0.5765 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9828   -0.0753   -1.5566 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3438   -0.2655    0.1935 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4828    0.3905   -0.8594 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9085    0.3883   -0.4624 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8205   -0.6679   -0.6580 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9990   -0.2589   -0.2004 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8941    0.9781    0.2684 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0595    1.9039    0.9298 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.5962    1.3834    0.1065 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1215    0.2014    1.5672 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3827    1.2936    1.9173 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4913   -0.6168    2.6676 O   0  0  0  0  0  1  0  0  0  0  0  0
   -1.4890   -2.2936    0.4806 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8083   -2.0799   -0.6839 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9891   -1.5543    1.0703 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1661    1.7276    0.3684 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5925    0.4709    1.6575 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5560    0.6435    0.1798 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6956    0.9455   -1.8498 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0775   -0.2066   -1.7223 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4971   -0.8593   -2.1865 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0065   -1.3529    0.1863 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4269   -0.2330   -1.7801 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1425    1.4227   -1.1051 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5492   -1.6205   -1.1070 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8972   -0.8030   -0.1942 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2498    2.3345    0.3839 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  2  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
  5 13  1  0
 13 14  2  0
 13 15  1  0
 12  7  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  3 19  1  0
  3 20  1  0
  3 21  1  0
  4 22  1  0
  4 23  1  0
  4 24  1  0
  5 25  1  1
  6 26  1  0
  6 27  1  0
  8 28  1  0
  9 29  1  0
 12 30  1  0
M  CHG  2   2   1  15  -1
M  END

HEADER    PROTEIN                                 30-OCT-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   30-OCT-19         0                                  
HETATM    1  C   UNK     0    8668.6598667.149   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8667.3248667.917   0.000  0.00  0.00           C+0
HETATM    3  S   UNK     0    8662.0198667.628   0.000  0.00  0.00           S+0
HETATM    4  N   UNK     0    8668.6598665.606   0.000  0.00  0.00           N+1
HETATM    5  C   UNK     0    8669.9988664.833   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0    8667.3208664.833   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    8668.6598663.779   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8669.9988667.917   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0    8671.3338667.149   0.000  0.00  0.00           O-1
HETATM   10  O   UNK     0    8669.9988669.461   0.000  0.00  0.00           O+0
HETATM   11  N   UNK     0    8664.7328668.071   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0    8663.4868667.166   0.000  0.00  0.00           C+0
HETATM   13  N   UNK     0    8663.9628665.701   0.000  0.00  0.00           N+0
HETATM   14  C   UNK     0    8665.5028665.701   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8665.9788667.166   0.000  0.00  0.00           C+0
CONECT    1    2    4    8                                                  
CONECT    2    1   15                                                       
CONECT    3   12                                                            
CONECT    4    1    5    6    7                                             
CONECT    5    4                                                            
CONECT    6    4                                                            
CONECT    7    4                                                            
CONECT    8    1    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8                                                            
CONECT   11   12   15                                                       
CONECT   12   11   13    3                                                  
CONECT   13   12   14                                                       
CONECT   14   15   13                                                       
CONECT   15   14   11    2                                                  
MASTER        0    0    0    0    0    0    0    0   15    0   30    0
END

COMPND    HMDB0003045
HETATM    1  C1  UNL     1      -2.329  -1.601   0.181  1.00  0.00           C  
HETATM    2  N1  UNL     1      -1.756  -0.303  -0.146  1.00  0.00           N1+
HETATM    3  C2  UNL     1      -2.507   0.708   0.576  1.00  0.00           C  
HETATM    4  C3  UNL     1      -1.983  -0.075  -1.557  1.00  0.00           C  
HETATM    5  C4  UNL     1      -0.344  -0.265   0.193  1.00  0.00           C  
HETATM    6  C5  UNL     1       0.483   0.391  -0.859  1.00  0.00           C  
HETATM    7  C6  UNL     1       1.908   0.388  -0.462  1.00  0.00           C  
HETATM    8  C7  UNL     1       2.821  -0.668  -0.658  1.00  0.00           C  
HETATM    9  N2  UNL     1       3.999  -0.259  -0.200  1.00  0.00           N  
HETATM   10  C8  UNL     1       3.894   0.978   0.268  1.00  0.00           C  
HETATM   11  S1  UNL     1       5.059   1.904   0.930  1.00  0.00           S  
HETATM   12  N3  UNL     1       2.596   1.383   0.107  1.00  0.00           N  
HETATM   13  C9  UNL     1      -0.121   0.201   1.567  1.00  0.00           C  
HETATM   14  O1  UNL     1       0.383   1.294   1.917  1.00  0.00           O  
HETATM   15  O2  UNL     1      -0.491  -0.617   2.668  1.00  0.00           O1-
HETATM   16  H1  UNL     1      -1.489  -2.294   0.481  1.00  0.00           H  
HETATM   17  H2  UNL     1      -2.808  -2.080  -0.684  1.00  0.00           H  
HETATM   18  H3  UNL     1      -2.989  -1.554   1.070  1.00  0.00           H  
HETATM   19  H4  UNL     1      -2.166   1.728   0.368  1.00  0.00           H  
HETATM   20  H5  UNL     1      -2.593   0.471   1.657  1.00  0.00           H  
HETATM   21  H6  UNL     1      -3.556   0.643   0.180  1.00  0.00           H  
HETATM   22  H7  UNL     1      -1.696   0.946  -1.850  1.00  0.00           H  
HETATM   23  H8  UNL     1      -3.078  -0.207  -1.722  1.00  0.00           H  
HETATM   24  H9  UNL     1      -1.497  -0.859  -2.187  1.00  0.00           H  
HETATM   25  H10 UNL     1      -0.006  -1.353   0.186  1.00  0.00           H  
HETATM   26  H11 UNL     1       0.427  -0.233  -1.780  1.00  0.00           H  
HETATM   27  H12 UNL     1       0.143   1.423  -1.105  1.00  0.00           H  
HETATM   28  H13 UNL     1       2.549  -1.620  -1.107  1.00  0.00           H  
HETATM   29  H14 UNL     1       4.897  -0.803  -0.194  1.00  0.00           H  
HETATM   30  H15 UNL     1       2.250   2.335   0.384  1.00  0.00           H  
CONECT    1    2   16   17   18
CONECT    2    3    4    5
CONECT    3   19   20   21
CONECT    4   22   23   24
CONECT    5    6   13   25
CONECT    6    7   26   27
CONECT    7    8    8   12
CONECT    8    9   28
CONECT    9   10   29
CONECT   10   11   11   12
CONECT   12   30
CONECT   13   14   14   15
END

HMDB0003045
     RDKit          3D
Ergothioneine
 30 30  0  0  0  0  0  0  0  0999 V2000
   -2.3288   -1.6009    0.1806 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7556   -0.3029   -0.1457 N   0  0  0  0  0  4  0  0  0  0  0  0
   -2.5073    0.7076    0.5765 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9828   -0.0753   -1.5566 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3438   -0.2655    0.1935 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4828    0.3905   -0.8594 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9085    0.3883   -0.4624 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8205   -0.6679   -0.6580 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9990   -0.2589   -0.2004 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8941    0.9781    0.2684 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0595    1.9039    0.9298 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.5962    1.3834    0.1065 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1215    0.2014    1.5672 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3827    1.2936    1.9173 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4913   -0.6168    2.6676 O   0  0  0  0  0  1  0  0  0  0  0  0
   -1.4890   -2.2936    0.4806 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8083   -2.0799   -0.6839 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9891   -1.5543    1.0703 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1661    1.7276    0.3684 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5925    0.4709    1.6575 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5560    0.6435    0.1798 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6956    0.9455   -1.8498 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0775   -0.2066   -1.7223 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4971   -0.8593   -2.1865 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0065   -1.3529    0.1863 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4269   -0.2330   -1.7801 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1425    1.4227   -1.1051 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5492   -1.6205   -1.1070 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8972   -0.8030   -0.1942 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2498    2.3345    0.3839 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  2  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
  5 13  1  0
 13 14  2  0
 13 15  1  0
 12  7  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  3 19  1  0
  3 20  1  0
  3 21  1  0
  4 22  1  0
  4 23  1  0
  4 24  1  0
  5 25  1  1
  6 26  1  0
  6 27  1  0
  8 28  1  0
  9 29  1  0
 12 30  1  0
M  CHG  2   2   1  15  -1
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
(2S)-3-(2-Mercapto-1H-imidazol-5-yl)-2-(trimethylammonio)propanoate	ChEBI
(AlphaS)-alpha-carboxy-2,3-dihydro-N,N,N-trimethyl-2-thioxo-1H-imidazole-4-ethanaminium inner salt	ChEBI
(S)-(1-Carboxy-2-(2-mercaptoimidazol-4-yl)ethyl)trimethylammonium hydroxide	ChEBI
2-Mercaptohistidine trimethylbetaine	ChEBI
3-(2-Sulfanylidene-1,3-dihydroimidazol-4-yl)-2-trimethylammonio-propanoate	ChEBI
Ergothioneine thiol	ChEBI
Ergothionine	ChEBI
Erythrothioneine	ChEBI
L-Ergothioneine	ChEBI
L-Thioneine	ChEBI
Sympectothion	ChEBI
Thiolhistidine-betaine	ChEBI
Thiolhistidinebetaine	ChEBI
(2S)-3-(2-Mercapto-1H-imidazol-5-yl)-2-(trimethylammonio)propanoic acid	Generator
(AlphaS)-a-carboxy-2,3-dihydro-N,N,N-trimethyl-2-thioxo-1H-imidazole-4-ethanaminium inner salt	Generator
(AlphaS)-α-carboxy-2,3-dihydro-N,N,N-trimethyl-2-thioxo-1H-imidazole-4-ethanaminium inner salt	Generator
3-(2-Sulfanylidene-1,3-dihydroimidazol-4-yl)-2-trimethylammonio-propanoic acid	Generator
3-(2-Sulphanylidene-1,3-dihydroimidazol-4-yl)-2-trimethylammonio-propanoate	Generator
3-(2-Sulphanylidene-1,3-dihydroimidazol-4-yl)-2-trimethylammonio-propanoic acid	Generator
2 Thiol L histidine betaine	HMDB
2-Thiol-L-histidine-betaine	HMDB
Thioneine	HMDB

Chemical Formula

C₉H₁₅N₃O₂S

Average Molecular Weight

229.299

Monoisotopic Molecular Weight

229.088497429

IUPAC Name

{5-[(2S)-2-carboxy-2-(trimethylazaniumyl)ethyl]-1H-imidazol-2-yl}sulfanide

Traditional Name

ergothioneine

CAS Registry Number

497-30-3

SMILES

C[N+](C)(C)[C@@H](CC1=CNC(=S)N1)C([O-])=O

InChI Identifier

InChI=1S/C9H15N3O2S/c1-12(2,3)7(8(13)14)4-6-5-10-9(15)11-6/h5,7H,4H2,1-3H3,(H2-,10,11,13,14,15)/t7-/m0/s1

InChI Key

SSISHJJTAXXQAX-ZETCQYMHSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as histidine and derivatives. Histidine and derivatives are compounds containing cysteine or a derivative thereof resulting from reaction of cysteine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Histidine and derivatives

Alternative Parents

Substituents

Histidine or derivatives
Alpha-amino acid
L-alpha-amino acid
Imidazolyl carboxylic acid derivative
Aralkylamine
Imidazole-2-thione
Azole
Imidazole
Quaternary ammonium salt
Heteroaromatic compound
Tetraalkylammonium salt
Thiourea
Carboxylic acid salt
Organoheterocyclic compound
Azacycle
Carboxylic acid
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Organonitrogen compound
Organooxygen compound
Organopnictogen compound
Organic oxygen compound
Amine
Organosulfur compound
Organic oxide
Organic salt
Organic nitrogen compound
Carbonyl group
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

amino-acid betaine (CHEBI:4828 )
L-histidine derivative (CHEBI:4828 )

Ontology

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	1000000 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.059 g/L	ALOGPS
logP	-1.7	ALOGPS
logP	-4	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	1.88	ChemAxon
pKa (Strongest Basic)	5.31	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	65.98 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	68.69 m³·mol⁻¹	ChemAxon
Polarizability	23.5 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	147.204	30932474
DeepCCS	[M-H]-	144.846	30932474
DeepCCS	[M-2H]-	178.446	30932474
DeepCCS	[M+Na]+	153.35	30932474
AllCCS	[M+H]+	147.9	32859911
AllCCS	[M+H-H2O]+	144.4	32859911
AllCCS	[M+NH4]+	151.1	32859911
AllCCS	[M+Na]+	152.1	32859911
AllCCS	[M-H]-	157.5	32859911
AllCCS	[M+Na-2H]-	158.5	32859911
AllCCS	[M+HCOO]-	159.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Ergothioneine	C[N+](C)(C)[C@@H](CC1=CNC(=S)N1)C([O-])=O	2854.8	Standard polar	33892256
Ergothioneine	C[N+](C)(C)[C@@H](CC1=CNC(=S)N1)C([O-])=O	1774.5	Standard non polar	33892256
Ergothioneine	C[N+](C)(C)[C@@H](CC1=CNC(=S)N1)C([O-])=O	2293.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Ergothioneine,1TMS,isomer #1	C[N+](C)(C)[C@@H](CC1=CN([Si](C)(C)C)C(=S)[NH]1)C(=O)[O-]	2009.7	Semi standard non polar	33892256
Ergothioneine,1TMS,isomer #1	C[N+](C)(C)[C@@H](CC1=CN([Si](C)(C)C)C(=S)[NH]1)C(=O)[O-]	2095.4	Standard non polar	33892256
Ergothioneine,1TMS,isomer #1	C[N+](C)(C)[C@@H](CC1=CN([Si](C)(C)C)C(=S)[NH]1)C(=O)[O-]	2651.5	Standard polar	33892256
Ergothioneine,1TMS,isomer #2	C[N+](C)(C)[C@@H](CC1=C[NH]C(=S)N1[Si](C)(C)C)C(=O)[O-]	1993.0	Semi standard non polar	33892256
Ergothioneine,1TMS,isomer #2	C[N+](C)(C)[C@@H](CC1=C[NH]C(=S)N1[Si](C)(C)C)C(=O)[O-]	2082.4	Standard non polar	33892256
Ergothioneine,1TMS,isomer #2	C[N+](C)(C)[C@@H](CC1=C[NH]C(=S)N1[Si](C)(C)C)C(=O)[O-]	2627.2	Standard polar	33892256
Ergothioneine,2TMS,isomer #1	C[N+](C)(C)[C@@H](CC1=CN([Si](C)(C)C)C(=S)N1[Si](C)(C)C)C(=O)[O-]	2078.2	Semi standard non polar	33892256
Ergothioneine,2TMS,isomer #1	C[N+](C)(C)[C@@H](CC1=CN([Si](C)(C)C)C(=S)N1[Si](C)(C)C)C(=O)[O-]	2161.8	Standard non polar	33892256
Ergothioneine,2TMS,isomer #1	C[N+](C)(C)[C@@H](CC1=CN([Si](C)(C)C)C(=S)N1[Si](C)(C)C)C(=O)[O-]	2435.9	Standard polar	33892256
Ergothioneine,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1C=C(C[C@@H](C(=O)[O-])[N+](C)(C)C)[NH]C1=S	2201.2	Semi standard non polar	33892256
Ergothioneine,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1C=C(C[C@@H](C(=O)[O-])[N+](C)(C)C)[NH]C1=S	2328.4	Standard non polar	33892256
Ergothioneine,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1C=C(C[C@@H](C(=O)[O-])[N+](C)(C)C)[NH]C1=S	2685.9	Standard polar	33892256
Ergothioneine,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N1C(C[C@@H](C(=O)[O-])[N+](C)(C)C)=C[NH]C1=S	2170.9	Semi standard non polar	33892256
Ergothioneine,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N1C(C[C@@H](C(=O)[O-])[N+](C)(C)C)=C[NH]C1=S	2336.0	Standard non polar	33892256
Ergothioneine,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N1C(C[C@@H](C(=O)[O-])[N+](C)(C)C)=C[NH]C1=S	2653.6	Standard polar	33892256
Ergothioneine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1C=C(C[C@@H](C(=O)[O-])[N+](C)(C)C)N([Si](C)(C)C(C)(C)C)C1=S	2489.6	Semi standard non polar	33892256
Ergothioneine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1C=C(C[C@@H](C(=O)[O-])[N+](C)(C)C)N([Si](C)(C)C(C)(C)C)C1=S	2616.2	Standard non polar	33892256
Ergothioneine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1C=C(C[C@@H](C(=O)[O-])[N+](C)(C)C)N([Si](C)(C)C(C)(C)C)C1=S	2524.3	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Ergothioneine GC-MS (Non-derivatized) - 70eV, Positive	splash10-03dr-5910000000-5059c1d23a7b077f405f	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ergothioneine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ergothioneine 30V, Positive-QTOF	splash10-016r-9500000000-04f10497f2180ec7fad9	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ergothioneine 40V, Positive-QTOF	splash10-014i-9100000000-da6c9ba163f2d8ff5693	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ergothioneine 20V, Positive-QTOF	splash10-004i-3900000000-82fdfe23ca09b0ae98ce	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ergothioneine 10V, Positive-QTOF	splash10-002r-2920000000-1c6f86a16d521e0bbab6	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ergothioneine 35V, Positive-QTOF	splash10-004i-0900000000-9d0138913c95dbd5c498	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ergothioneine 50V, Positive-QTOF	splash10-004i-3900000000-caa65ea3e411af866d82	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ergothioneine 10V, Positive-QTOF	splash10-052r-9830000000-0adc722312e2f3cf4a1a	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ergothioneine 0V, Positive-QTOF	splash10-001r-0960000000-94c69f06737080f61979	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ergothioneine 10V, Positive-QTOF	splash10-000i-1930000000-588cc28e89f864acdd3d	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ergothioneine 30V, Positive-QTOF	splash10-0gdi-9850000000-40c5889b6855f1a4353e	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ergothioneine 0V, Positive-QTOF	splash10-001i-0290000000-81d6bfea2ae2d5d06472	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ergothioneine 30V, Positive-QTOF	splash10-052f-9000000000-28c8512538d456c43727	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ergothioneine 10V, Positive-QTOF	splash10-001i-0190000000-5bfc4fb56e55998326c9	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ergothioneine 20V, Positive-QTOF	splash10-01q9-0960000000-7536b2e5a9447d8762e8	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ergothioneine 40V, Positive-QTOF	splash10-0uxu-6900000000-9095b54dd80a9a95e5e0	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ergothioneine 10V, Negative-QTOF	splash10-004i-0190000000-0f87ac5b3b1e5f1dd7bb	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ergothioneine 20V, Negative-QTOF	splash10-004i-5690000000-06e985e77495cc5c0e75	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ergothioneine 40V, Negative-QTOF	splash10-0a4i-9000000000-e8772cee3888cb9ca84d	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ergothioneine 10V, Positive-QTOF	splash10-001i-0980000000-10a32741360fe7b33d09	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ergothioneine 20V, Positive-QTOF	splash10-00b9-0900000000-0949d8b6748b0ffb9616	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ergothioneine 40V, Positive-QTOF	splash10-004i-5900000000-4ddb7efd11211837e715	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ergothioneine 10V, Negative-QTOF	splash10-004i-0090000000-feef1aee555bb816227c	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ergothioneine 20V, Negative-QTOF	splash10-004j-5290000000-08d7e98139af1d46215b	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ergothioneine 40V, Negative-QTOF	splash10-004j-7900000000-e26a7c567169504547f2	2021-09-22	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood
Urine

Tissue Locations

Placenta

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Female	Normal	27355821	details
Blood	Detected and Quantified	0.99 (0.84–1.52) uM	Adult (>18 years old)	Both	Normal	24392160	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Ergothioneine

METLIN ID

PubChem Compound

5351619

PDB ID

Not Available

ChEBI ID

4828

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1080351

References

Synthesis Reference

Xu, Jinzhu; Yadan, Jean Claude. Synthesis of L-(+)-Ergothioneine. Journal of Organic Chemistry (1995), 60(20), 6296-301.

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Grundemann D, Harlfinger S, Golz S, Geerts A, Lazar A, Berkels R, Jung N, Rubbert A, Schomig E: Discovery of the ergothioneine transporter. Proc Natl Acad Sci U S A. 2005 Apr 5;102(14):5256-61. Epub 2005 Mar 28. [PubMed:15795384 ]
OHARA M, TOMITA K, WATANABE R, KONO K, WATANABE K: Estimation of ergothioneine in urine, blood and organs by determination of the alkaline perhydrol-labile sulfur. Jpn J Med Sci Biol. 1952 Oct;5(5):259-63. [PubMed:13034359 ]
Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]

Transporters

Enzyme Details

1. Solute carrier family 22 member 4

General function:: Involved in ion transmembrane transporter activity
Specific function:: Sodium-ion dependent, low affinity carnitine transporter. Probably transports one sodium ion with one molecule of carnitine. Also transports organic cations such as tetraethylammonium (TEA) without the involvement of sodium. Relative uptake activity ratio of carnitine to TEA is 1.78. A key substrate of this transporter seems to be ergothioneine (ET)
Gene Name:: SLC22A4
Uniprot ID:: Q9H015
Molecular weight:: 62154.5

Showing metabocard for Ergothioneine (HMDB0003045)

MOL for HMDB0003045 (Ergothioneine)

3D MOL for HMDB0003045 (Ergothioneine)

3D SDF for HMDB0003045 (Ergothioneine)

3D-SDF for HMDB0003045 (Ergothioneine)

PDB for HMDB0003045 (Ergothioneine)

3D PDB for HMDB0003045 (Ergothioneine)

SMILES for HMDB0003045 (Ergothioneine)

INCHI for HMDB0003045 (Ergothioneine)

Structure for HMDB0003045 (Ergothioneine)

3D Structure for HMDB0003045 (Ergothioneine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Transporters