MiMeDB: Showing metabocard for Thiamine (MMDBc0000079)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2020-10-27 23:29:37 UTC

Update Date

2024-10-10 01:31:36 UTC

Metabolite ID

MMDBc0000079

Metabolite Identification

Common Name

Thiamine

Description

Thiamine or thiamin, also known as vitamin B1, is a colorless compound with the chemical formula C12H17N4OS. It is soluble in water and insoluble in alcohol. Thiamine decomposes if heated. Thiamine was first discovered by Umetaro Suzuki in Japan when researching how rice bran cured patients of Beriberi. Thiamine plays a key role in intracellular glucose metabolism and it is thought that thiamine inhibits the effect of glucose and insulin on arterial smooth muscle cell proliferation. thiamine plays an important role in helping the body convert carbohydrates and fat into energy. It is essential for normal growth and development and helps to maintain proper functioning of the heart and the nervous and digestive systems. Thiamine cannot be stored in the body; however, once absorbed, the vitamin is concentrated in muscle tissue.

Structure

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

HMDB0000235
     RDKit          3D
Thiamine
 35 36  0  0  0  0  0  0  0  0999 V2000
    5.1909   -1.4321   -0.0637 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9661   -0.5749    0.0799 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8042    0.5339   -0.6607 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7301    1.3239   -0.5653 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6796    1.0289    0.3424 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5140    1.9222    0.3591 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5645    1.3938   -0.5358 N   0  0  0  0  0  4  0  0  0  0  0  0
   -0.3991    1.5916   -1.8735 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7291    0.8396   -2.5789 S   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4835    0.2798   -1.1525 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7611   -0.5230   -1.0437 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5663   -1.9797   -0.9174 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8549   -2.3804    0.1703 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6344    0.7225   -0.1659 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0315    0.4882    1.3003 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8708   -0.0972    1.0793 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8970   -0.4661    2.0561 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9932   -0.8769    0.9436 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.4729   -1.9085    0.8784 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0234   -0.7888   -0.3788 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0513   -2.1987   -0.8493 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5956    2.2169   -1.1588 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8037    2.9473   -0.0204 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1103    2.1271    1.3668 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4460    2.1375   -2.3499 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3066   -0.0859   -0.1823 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3930   -0.3021   -1.9377 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0683   -2.3644   -1.8394 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5894   -2.4497   -0.9505 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3754   -2.8107    0.8729 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5782    1.2262    1.9589 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1365    0.5652    1.3859 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7619   -0.5080    1.6484 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4509   -1.4018    1.9221 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6339    0.1464    2.8602 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 10 14  2  0
 14 15  1  0
  5 16  1  0
 16 17  1  0
 16 18  2  0
 18  2  1  0
 14  7  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  4 22  1  0
  6 23  1  0
  6 24  1  0
  8 25  1  0
 11 26  1  0
 11 27  1  0
 12 28  1  0
 12 29  1  0
 13 30  1  0
 15 31  1  0
 15 32  1  0
 15 33  1  0
 17 34  1  0
 17 35  1  0
M  CHG  1   7   1
M  END

  Mrv1652311131908262D          

 18 19  0  0  0  0            999 V2000
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4290   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0001   -1.6500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1435    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9281    0.6674    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.9281   -0.6674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1831   -1.4521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4130    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2380    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6505    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4755    0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1435   -0.4125    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
  7  1  1  0  0  0  0
  1  2  2  0  0  0  0
  1  3  1  0  0  0  0
  3  8  1  0  0  0  0
  3  4  2  0  0  0  0
  2  5  1  0  0  0  0
  4  6  1  0  0  0  0
  5  6  2  0  0  0  0
  6  9  1  0  0  0  0
 18  7  1  0  0  0  0
 11 10  1  0  0  0  0
 18 10  2  0  0  0  0
 11 14  1  0  0  0  0
 14 12  2  0  0  0  0
 12 18  1  0  0  0  0
 12 13  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
M  CHG  1  18   1
M  END
> <DATABASE_ID>
MMDBc0000079

> <DATABASE_NAME>
MIME

> <SMILES>
CC1=C(CCO)SC=[N+]1CC1=CN=C(C)N=C1N

> <INCHI_IDENTIFIER>
InChI=1S/C12H17N4OS/c1-8-11(3-4-17)18-7-16(8)6-10-5-14-9(2)15-12(10)13/h5,7,17H,3-4,6H2,1-2H3,(H2,13,14,15)/q+1

> <INCHI_KEY>
JZRWCGZRTZMZEH-UHFFFAOYSA-N

> <FORMULA>
C12H17N4OS

> <MOLECULAR_WEIGHT>
265.355

> <EXACT_MASS>
265.112306876

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
35

> <JCHEM_AVERAGE_POLARIZABILITY>
28.144123736165753

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
1

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-[(4-amino-2-methylpyrimidin-5-yl)methyl]-5-(2-hydroxyethyl)-4-methyl-1,3-thiazol-3-ium

> <ALOGPS_LOGP>
-2.11

> <JCHEM_LOGP>
-3.0974126491384126

> <ALOGPS_LOGS>
-4.29

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
19.25564694993423

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.504603864011504

> <JCHEM_PKA_STRONGEST_BASIC>
5.5375484421713

> <JCHEM_POLAR_SURFACE_AREA>
75.91

> <JCHEM_REFRACTIVITY>
73.39970000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.53e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
thiamine

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0000235
     RDKit          3D
Thiamine
 35 36  0  0  0  0  0  0  0  0999 V2000
    5.1909   -1.4321   -0.0637 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9661   -0.5749    0.0799 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8042    0.5339   -0.6607 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7301    1.3239   -0.5653 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6796    1.0289    0.3424 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5140    1.9222    0.3591 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5645    1.3938   -0.5358 N   0  0  0  0  0  4  0  0  0  0  0  0
   -0.3991    1.5916   -1.8735 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7291    0.8396   -2.5789 S   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4835    0.2798   -1.1525 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7611   -0.5230   -1.0437 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5663   -1.9797   -0.9174 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8549   -2.3804    0.1703 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6344    0.7225   -0.1659 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0315    0.4882    1.3003 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8708   -0.0972    1.0793 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8970   -0.4661    2.0561 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9932   -0.8769    0.9436 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.4729   -1.9085    0.8784 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0234   -0.7888   -0.3788 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0513   -2.1987   -0.8493 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5956    2.2169   -1.1588 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8037    2.9473   -0.0204 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1103    2.1271    1.3668 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4460    2.1375   -2.3499 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3066   -0.0859   -0.1823 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3930   -0.3021   -1.9377 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0683   -2.3644   -1.8394 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5894   -2.4497   -0.9505 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3754   -2.8107    0.8729 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5782    1.2262    1.9589 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1365    0.5652    1.3859 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7619   -0.5080    1.6484 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4509   -1.4018    1.9221 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6339    0.1464    2.8602 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 10 14  2  0
 14 15  1  0
  5 16  1  0
 16 17  1  0
 16 18  2  0
 18  2  1  0
 14  7  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  4 22  1  0
  6 23  1  0
  6 24  1  0
  8 25  1  0
 11 26  1  0
 11 27  1  0
 12 28  1  0
 12 29  1  0
 13 30  1  0
 15 31  1  0
 15 32  1  0
 15 33  1  0
 17 34  1  0
 17 35  1  0
M  CHG  1   7   1
M  END

HEADER    PROTEIN                                 13-NOV-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   13-NOV-19         0                                  
HETATM    1  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334   0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000  -1.540   0.000  0.00  0.00           C+0
HETATM    4  N   UNK     0      -1.334  -0.770   0.000  0.00  0.00           N+0
HETATM    5  N   UNK     0       0.000   1.540   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0      -1.334   0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667  -1.540   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0       0.000  -3.080   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.001   0.770   0.000  0.00  0.00           C+0
HETATM   11  S   UNK     0       5.466   1.246   0.000  0.00  0.00           S+0
HETATM   12  C   UNK     0       5.466  -1.246   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.942  -2.711   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.371   0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.911   0.000   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.681   1.334   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      10.221   1.334   0.000  0.00  0.00           O+0
HETATM   18  N   UNK     0       4.001  -0.770   0.000  0.00  0.00           N+1
CONECT    1    7    2    3                                                  
CONECT    2    1    5                                                       
CONECT    3    1    8    4                                                  
CONECT    4    3    6                                                       
CONECT    5    2    6                                                       
CONECT    6    4    5    9                                                  
CONECT    7    1   18                                                       
CONECT    8    3                                                            
CONECT    9    6                                                            
CONECT   10   11   18                                                       
CONECT   11   10   14                                                       
CONECT   12   14   18   13                                                  
CONECT   13   12                                                            
CONECT   14   11   12   15                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16                                                            
CONECT   18    7   10   12                                                  
MASTER        0    0    0    0    0    0    0    0   18    0   38    0
END

COMPND    HMDB0000235
HETATM    1  C1  UNL     1       5.191  -1.432  -0.064  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.966  -0.575   0.080  1.00  0.00           C  
HETATM    3  N1  UNL     1       3.804   0.534  -0.661  1.00  0.00           N  
HETATM    4  C3  UNL     1       2.730   1.324  -0.565  1.00  0.00           C  
HETATM    5  C4  UNL     1       1.680   1.029   0.342  1.00  0.00           C  
HETATM    6  C5  UNL     1       0.514   1.922   0.359  1.00  0.00           C  
HETATM    7  N2  UNL     1      -0.565   1.394  -0.536  1.00  0.00           N1+
HETATM    8  C6  UNL     1      -0.399   1.592  -1.873  1.00  0.00           C  
HETATM    9  S1  UNL     1      -1.729   0.840  -2.579  1.00  0.00           S  
HETATM   10  C7  UNL     1      -2.483   0.280  -1.152  1.00  0.00           C  
HETATM   11  C8  UNL     1      -3.761  -0.523  -1.044  1.00  0.00           C  
HETATM   12  C9  UNL     1      -3.566  -1.980  -0.917  1.00  0.00           C  
HETATM   13  O1  UNL     1      -2.855  -2.380   0.170  1.00  0.00           O  
HETATM   14  C10 UNL     1      -1.634   0.723  -0.166  1.00  0.00           C  
HETATM   15  C11 UNL     1      -2.032   0.488   1.300  1.00  0.00           C  
HETATM   16  C12 UNL     1       1.871  -0.097   1.079  1.00  0.00           C  
HETATM   17  N3  UNL     1       0.897  -0.466   2.056  1.00  0.00           N  
HETATM   18  N4  UNL     1       2.993  -0.877   0.944  1.00  0.00           N  
HETATM   19  H1  UNL     1       5.473  -1.909   0.878  1.00  0.00           H  
HETATM   20  H2  UNL     1       6.023  -0.789  -0.379  1.00  0.00           H  
HETATM   21  H3  UNL     1       5.051  -2.199  -0.849  1.00  0.00           H  
HETATM   22  H4  UNL     1       2.596   2.217  -1.159  1.00  0.00           H  
HETATM   23  H5  UNL     1       0.804   2.947  -0.020  1.00  0.00           H  
HETATM   24  H6  UNL     1       0.110   2.127   1.367  1.00  0.00           H  
HETATM   25  H7  UNL     1       0.446   2.138  -2.350  1.00  0.00           H  
HETATM   26  H8  UNL     1      -4.307  -0.086  -0.182  1.00  0.00           H  
HETATM   27  H9  UNL     1      -4.393  -0.302  -1.938  1.00  0.00           H  
HETATM   28  H10 UNL     1      -3.068  -2.364  -1.839  1.00  0.00           H  
HETATM   29  H11 UNL     1      -4.589  -2.450  -0.951  1.00  0.00           H  
HETATM   30  H12 UNL     1      -3.375  -2.811   0.873  1.00  0.00           H  
HETATM   31  H13 UNL     1      -1.578   1.226   1.959  1.00  0.00           H  
HETATM   32  H14 UNL     1      -3.136   0.565   1.386  1.00  0.00           H  
HETATM   33  H15 UNL     1      -1.762  -0.508   1.648  1.00  0.00           H  
HETATM   34  H16 UNL     1       0.451  -1.402   1.922  1.00  0.00           H  
HETATM   35  H17 UNL     1       0.634   0.146   2.860  1.00  0.00           H  
CONECT    1    2   19   20   21
CONECT    2    3    3   18
CONECT    3    4
CONECT    4    5    5   22
CONECT    5    6   16
CONECT    6    7   23   24
CONECT    7    8    8   14
CONECT    8    9   25
CONECT    9   10
CONECT   10   11   14   14
CONECT   11   12   26   27
CONECT   12   13   28   29
CONECT   13   30
CONECT   14   15
CONECT   15   31   32   33
CONECT   16   17   18   18
CONECT   17   34   35
END

HMDB0000235
     RDKit          3D
Thiamine
 35 36  0  0  0  0  0  0  0  0999 V2000
    5.1909   -1.4321   -0.0637 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9661   -0.5749    0.0799 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8042    0.5339   -0.6607 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7301    1.3239   -0.5653 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6796    1.0289    0.3424 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5140    1.9222    0.3591 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5645    1.3938   -0.5358 N   0  0  0  0  0  4  0  0  0  0  0  0
   -0.3991    1.5916   -1.8735 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7291    0.8396   -2.5789 S   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4835    0.2798   -1.1525 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7611   -0.5230   -1.0437 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5663   -1.9797   -0.9174 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8549   -2.3804    0.1703 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6344    0.7225   -0.1659 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0315    0.4882    1.3003 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8708   -0.0972    1.0793 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8970   -0.4661    2.0561 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9932   -0.8769    0.9436 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.4729   -1.9085    0.8784 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0234   -0.7888   -0.3788 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0513   -2.1987   -0.8493 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5956    2.2169   -1.1588 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8037    2.9473   -0.0204 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1103    2.1271    1.3668 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4460    2.1375   -2.3499 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3066   -0.0859   -0.1823 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3930   -0.3021   -1.9377 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0683   -2.3644   -1.8394 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5894   -2.4497   -0.9505 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3754   -2.8107    0.8729 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5782    1.2262    1.9589 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1365    0.5652    1.3859 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7619   -0.5080    1.6484 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4509   -1.4018    1.9221 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6339    0.1464    2.8602 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 10 14  2  0
 14 15  1  0
  5 16  1  0
 16 17  1  0
 16 18  2  0
 18  2  1  0
 14  7  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  4 22  1  0
  6 23  1  0
  6 24  1  0
  8 25  1  0
 11 26  1  0
 11 27  1  0
 12 28  1  0
 12 29  1  0
 13 30  1  0
 15 31  1  0
 15 32  1  0
 15 33  1  0
 17 34  1  0
 17 35  1  0
M  CHG  1   7   1
M  END

Synonyms

Value	Source
3-(4-AMINO-2-methyl-pyrimidin-5-ylmethyl)-5-(2-hydroxy-ethyl)-4-methyl-thiazol-3-ium	ChEBI
Aneurin	ChEBI
Antiberiberi factor	ChEBI
Thiamin	ChEBI
Thiamine(1+) ion	ChEBI
Thiaminium	ChEBI
Vitamin b1	ChEBI
Apate drops	HMDB
Beatine	HMDB
Bedome	HMDB
Begiolan	HMDB
Benerva	HMDB
Bequin	HMDB
Berin	HMDB
Betalin S	HMDB
Betaxin	HMDB
Bethiazine	HMDB
Beuion	HMDB
Bevitex	HMDB
Bevitine	HMDB
Bewon	HMDB
Biamine	HMDB
Bithiamin	HMDB
Biuno	HMDB
Bivatin	HMDB
Bivita	HMDB
Cernevit-12	HMDB
Clotiamina	HMDB
Eskapen	HMDB
Eskaphen	HMDB
Hybee	HMDB
Lixa-beta	HMDB
Metabolin	HMDB
Slowten	HMDB
THD	HMDB
Thiadoxine	HMDB
Thiaminal	HMDB
Thiamol	HMDB
Thiavit	HMDB
Tiamidon	HMDB
Tiaminal	HMDB
Trophite	HMDB
Vetalin S	HMDB
VIB	HMDB
Vinothiam	HMDB
Vitaneuron	HMDB
Mononitrate, thiamine	MeSH, HMDB
Thiamine mononitrate	MeSH, HMDB
Vitamin b 1	MeSH, HMDB

Molecular Formula

C₁₂H₁₇N₄OS

Average Mass

265.355

Monoisotopic Mass

265.112306876

IUPAC Name

3-[(4-amino-2-methylpyrimidin-5-yl)methyl]-5-(2-hydroxyethyl)-4-methyl-1,3-thiazol-3-ium

Traditional Name

thiamine

CAS Registry Number

70-16-6

SMILES

CC1=C(CCO)SC=[N+]1CC1=CN=C(C)N=C1N

InChI Identifier

InChI=1S/C12H17N4OS/c1-8-11(3-4-17)18-7-16(8)6-10-5-14-9(2)15-12(10)13/h5,7,17H,3-4,6H2,1-2H3,(H2,13,14,15)/q+1

InChI Key

JZRWCGZRTZMZEH-UHFFFAOYSA-N

Chemical Taxonomy

Functional Ontology

Physical Properties

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-00e9-3890000000-9f8b525433ab279ad512	2016-09-22	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-00di-9442000000-05ab93d3afb7b6f538e9	2017-10-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, N/A (Annotated)	splash10-000i-0109000000-48864f31ba475645654b	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, N/A (Annotated)	splash10-05o1-9200000000-2ec0f3e9e364cffde16e	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, N/A (Annotated)	splash10-0aou-9000000000-0184506492d9f5b68b97	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-03di-0090000000-872150be83cbd75d8ecf	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-0002-0930000000-ecf71c75bdea859139d5	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-0002-0900000000-4d9113fdc633fb1ccbb5	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative	splash10-0002-0900000000-4a8016299623af0c3027	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative	splash10-0002-1900000000-773912c9f325c419c77d	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive	splash10-014i-0390000000-95f3ca57c95542bdc7e7	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive	splash10-00di-0900000000-e079d1fc1e06396dc524	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive	splash10-00di-0900000000-ebb16d4f204f291b9a3a	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive	splash10-00e9-4900000000-ad4d4779d76b9edb7ec5	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive	splash10-001i-9600000000-b631eed5be831527fc17	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positive	splash10-00di-0900000000-50f2f613f576814eb627	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positive	splash10-002b-0900000000-2f184bbfec6bc0ef00c6	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positive	splash10-001i-9000000000-35bc744495a2570a565f	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive	splash10-00di-1900000000-d8a7ac327273c32b4524	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative	splash10-0002-0920000000-ca80ef6513c61be5b5e9	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-03di-0090000000-872150be83cbd75d8ecf	2017-09-14	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-0190000000-183af2449d1439af9825	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-0090000000-2230ebc7c6b73192c26f	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0002-7920000000-75670df9647a475ca92c	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-3090000000-d0ff9a733629a86b75c7	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03dj-3690000000-db3f204af490d7e1722e	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0005-9000000000-5196f2b4daab995967bf	2016-09-12	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, H₂O, experimental)		2012-12-04	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)		2012-12-04	View Spectrum
1D NMR	¹H NMR Spectrum (1D, D₂O, experimental)		2016-10-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, D₂O, experimental)		2016-10-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, experimental)		2021-10-10	View Spectrum
2D NMR	[¹H, ¹H]-TOCSY. Unexported temporarily by An Chi on Oct 15, 2021 until json or nmrML file is generated. 2D NMR Spectrum (experimental)		2012-12-04	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)		2012-12-05	View Spectrum

Biological Properties

Human Proteins and Enzymes

Human Pathways

Metabolic Reactions

Health Effects and Bioactivity

Microbial Sources

Exposure Sources

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Feces	Detected but not Quantified									HMDB
Human Cerebrospinal fluid (csf)	Detected and Quantified	0.01	0.00			uM	Adult (>18 years old)	Not Specified	Alcoholism	HMDB	182198
Human Cerebrospinal fluid (csf)	Detected and Quantified	0.02	0.00			uM	Adult (>18 years old)	Not Specified	Alcoholism	HMDB	182198
Human Cerebrospinal fluid (csf)	Detected and Quantified	0.1	0.01			uM	Not Specified	Not Specified	Friedreich's ataxia	HMDB	11383938
Human Cerebrospinal fluid (csf)	Detected and Quantified	0.115	0.0464			uM	Adult (>18 years old)	Both	Friedreich's ataxia	HMDB	1538220
Human Blood	Detected and Quantified	0.18	0.066			uM	Adult (>18 years old)	Both	Friedreich's ataxia	HMDB	1538220
Human Blood	Detected and Quantified	0.035	0.006			uM	Elderly (>65 years old)	Both	Hemodialysis	HMDB	11684545
Human Cerebrospinal fluid (csf)	Detected and Quantified	0.06	0.01			uM	Adult (>18 years old)	Not Specified	Autosomal recessive spastic ataxia of Charlevoix-Saguena	HMDB	11383938
Human Cerebrospinal fluid (csf)	Detected and Quantified	0.09	0.01			uM	Adult (>18 years old)	Not Specified	Olivopontocerebellar atrophy (OPCA)	HMDB	11383938
Human Cerebrospinal fluid (csf)	Detected and Quantified	0.0902	0.0411			uM	Adult (>18 years old)	Both	Olivopontocerebellar atrophy (OPCA)	HMDB	1538220
Human Blood	Detected and Quantified	0.17	0.051			uM	Adult (>18 years old)	Both	Olivopontocerebellar atrophy (OPCA)	HMDB	1538220
Human Urine	Detected and Quantified	0.132				umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	15051849
Human Urine	Detected and Quantified	0.0283	0.0191			umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	20502474
Human Cerebrospinal fluid (csf)	Detected and Quantified	0.0487	0.00275			uM	Adult (>18 years old)	Not Specified	Normal	HMDB	182198
Human Urine	Detected and Quantified	0.0511	0.0255			umol/mmol creatinine	Children (1 - 13 years old)	Both	Normal	HMDB	20576202
Human Blood	Detected and Quantified	0.096	0.018			uM	Adult (>18 years old)	Not Specified	Normal	HMDB	11684545
Human Cerebrospinal fluid (csf)	Detected and Quantified	0.141	0.0543			uM	Adult (>18 years old)	Both	Normal	HMDB	1538220
Human Cerebrospinal fluid (csf)	Detected and Quantified	0.006		0.005	0.007	uM	Adult (>18 years old)	Both	Normal	HMDB	Geigy Scientific Tables, 8th Rev edition, pp. 130. Edited by C. Lentner, West Cadwell, N.J.: Medical education Div., Ciba-Geigy Corp. Basel, Switzerland c1981-1992.
Human Urine	Detected and Quantified	0.02	0.01			umol/mmol creatinine	Newborn (0-30 days old)	Both	Normal	HMDB	Geigy Scientific Tables, 8th Rev edition, pp. 130. Edited by C. Lentner, West Cadwell, N.J.: Medical education Div., Ciba-Geigy Corp. Basel, Switzerland c1981-1992.
Human Blood	Detected and Quantified	0.12		0.094	0.280	uM	Adult (>18 years old)	Female	Normal	HMDB	Geigy Scientific Tables, 8th Rev edition, pp. 130. Edited by C. Lentner, West Cadwell, N.J.: Medical education Div., Ciba-Geigy Corp. Basel, Switzerland c1981-1992.
Human Urine	Detected and Quantified	0.12	0.09			umol/mmol creatinine	Children (1-13 years old)	Both	Normal	HMDB	Geigy Scientific Tables, 8th Rev edition, pp. 130. Edited by C. Lentner, West Cadwell, N.J.: Medical education Div., Ciba-Geigy Corp. Basel, Switzerland c1981-1992.
Human Blood	Detected and Quantified	0.16		0.06	0.41	uM	Children (1-13 years old)	Both	Normal	HMDB	Geigy Scientific Tables, 8th Rev edition, pp. 130. Edited by C. Lentner, West Cadwell, N.J.: Medical education Div., Ciba-Geigy Corp. Basel, Switzerland c1981-1992.
Human Urine	Detected and Quantified	0.22		0.20	0.60	umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	Geigy Scientific Tables, 8th Rev edition, pp. 130. Edited by C. Lentner, West Cadwell, N.J.: Medical education Div., Ciba-Geigy Corp. Basel, Switzerland c1981-1992.
Human Blood	Detected and Quantified	0.34		0.14	0.79	uM	Newborn (0-30 days old)	Both	Normal	HMDB	Geigy Scientific Tables, 8th Rev edition, pp. 130. Edited by C. Lentner, West Cadwell, N.J.: Medical education Div., Ciba-Geigy Corp. Basel, Switzerland c1981-1992.
Human Saliva	Detected and Quantified	0.247	0.006			uM	Adult (>18 years old)	Both	Normal	HMDB	https://doi.org/10.1007/s11306-015-0840-5
Human Blood	Detected and Quantified			0.050	0.120	uM	Adult (>18 years old)	Both	Normal	HMDB	Molecular You (https://molecularyou.com)
Human Adipose tissue	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Adrenal gland	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Brain	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Erythrocyte	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Fibroblasts	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Intestine	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Kidney	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Liver	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Neuron	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Placenta	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Skeletal muscle	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Testis	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	27543620
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	25037050
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	29808030
Human Urine	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	32966057
Human Blood	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	32966057

External Links

References

General References

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Showing metabocard for Thiamine (MMDBc0000079)

MOL for #<Metabolite:0x00007f539815c0f0>

3D MOL for #<Metabolite:0x00007f539815c0f0>

3D SDF for #<Metabolite:0x00007f539815c0f0>

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PDB for #<Metabolite:0x00007f539815c0f0>

3D PDB for #<Metabolite:0x00007f539815c0f0>

SMILES for #<Metabolite:0x00007f539815c0f0>

INCHI for #<Metabolite:0x00007f539815c0f0>

Structure for #<Metabolite:0x00007f539815c0f0>

3D Structure for #<Metabolite:0x00007f539815c0f0>