You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.

Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (8) Show 8 proteins XML

enzymes (8) Show 8 proteins

Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2022-03-07 02:49:00 UTC

HMDB ID

HMDB0000235

Secondary Accession Numbers

HMDB00235

Metabolite Identification

Common Name

Thiamine

Description

Thiamine, also known as aneurin or vitamin B1, belongs to the class of organic compounds known as thiamines. Thiamines are compounds containing a thiamine moiety, which is structurally characterized by a 3-[(4-Amino-2-methyl-pyrimidin-5-yl)methyl]-4-methyl-thiazol-5-yl backbone. Thiamine exists in all living species, ranging from bacteria to plants to humans. Thiamine biosynthesis occurs in bacteria, some protozoans, plants, and fungi. Thiamine is a vitamin and an essential nutrient meaning the body cannot synthesize it, and it must be obtained from the diet. It is soluble in water and insoluble in alcohol. Thiamine decomposes if heated. Thiamine was first discovered in 1897 by Umetaro Suzuki in Japan when researching how rice bran cured patients of Beriberi. Thiamine was the first B vitamin to be isolated in 1926 and was first made in 1936. 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. Thiamine has antioxidant, erythropoietic, cognition-and mood-modulatory, antiatherosclerotic, putative ergogenic, and detoxification activities. Natural derivatives of thiamine, such as thiamine monophosphate (ThMP), thiamine diphosphate (ThDP), also sometimes called thiamine pyrophosphate (TPP), thiamine triphosphate (ThTP), and adenosine thiamine triphosphate (AThTP), act as coenzymes in addition to performing unique biological functions. Thiamine deficiency can lead to beriberi, Wernicke-Korsakoff syndrome, optic neuropathy, Leigh's disease, African seasonal ataxia (or Nigerian seasonal ataxia), and central pontine myelinolysis. In Western countries, thiamine deficiency is seen mainly in chronic alcoholism. Thiamine supplements or thiamine therapy can be used for the treatment of a number of disorders including thiamine and niacin deficiency states, Korsakov's alcoholic psychosis, Wernicke-Korsakov syndrome, delirium, and peripheral neuritis. In humans, thiamine is involved in the metabolic disorder called 2-methyl-3-hydroxybutyryl-CoA dehydrogenase deficiency. Outside of the human body, Thiamine is found in high quantities in whole grains, legumes, pork, fruits, and yeast and fish. Grain processing removes much of the thiamine content in grains, so in many countries cereals and flours are enriched with thiamine.

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>
HMDB0000235

> <DATABASE_NAME>
hmdb

> <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

View in JSmol View NMR Assignments View Stereo Labels

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

Chemical Formula

C₁₂H₁₇N₄OS

Average Molecular Weight

265.355

Monoisotopic Molecular Weight

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

Description

Belongs to the class of organic compounds known as thiamines. Thiamines are compounds containing a thiamine moiety, which is structurally characterized by a 3-[(4-Amino-2-methyl-pyrimidin-5-yl)methyl]-4-methyl-thiazol-5-yl backbone.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Diazines

Sub Class

Pyrimidines and pyrimidine derivatives

Direct Parent

Thiamines

Alternative Parents

Substituents

Thiamine
4,5-disubstituted 1,3-thiazole
Aminopyrimidine
Imidolactam
Azole
Thiazole
Heteroaromatic compound
Azacycle
Alcohol
Organopnictogen compound
Primary amine
Primary alcohol
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Organic oxygen compound
Hydrocarbon derivative
Amine
Organic cation
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

thiamine (CHEBI:18385 )
Water-soluble vitamins (C00378 )
a vitamin (THIAMINE )

Ontology

Physiological effect

Adverse health effect

Nervous system disorder

Central nervous system disorder

Friedreich's ataxia - Concentration is elevated compared to control group (PMID: 11684545 , PMID: 32966057 , PMID: 1538220 , +9

Source	Link
Pubmed	PMID: 11684545
Pubmed	PMID: 32966057
Pubmed	PMID: 1538220
Pubmed	PMID: 1538220
Pubmed	PMID: 182198
Pubmed	PMID: 29808030
Pubmed	PMID: 11383938
Pubmed	PMID: 7887134
Pubmed	PMID: 6184954
Pubmed	PMID: 6182605
Pubmed	PMID: 8884658
Pubmed	PMID: 7595563

)

Psychiatric disorder (PMID: 11739473 , PMID: 22944140 , PMID: 16959481 , +6 More

Source	Link
Pubmed	PMID: 11739473
Pubmed	PMID: 22944140
Pubmed	PMID: 16959481
Pubmed	PMID: 16959481
Pubmed	PMID: 18182448
Pubmed	PMID: 32966057
Pubmed	PMID: 16439592
Pubmed	PMID: 1620285
Pubmed	PMID: 10625505

Psychoactive substance abuse disorder

Alcoholism - Concentration is decreased compared to control group (PMID: 15340856 , PMID: 15340856 , PMID: 1538220 , +8

Source	Link
Pubmed	PMID: 15340856
Pubmed	PMID: 15340856
Pubmed	PMID: 1538220
Pubmed	PMID: 182198
Pubmed	PMID: 29808030
Pubmed	PMID: 182198
Pubmed	PMID: 19036546
Pubmed	PMID: 11958947
Pubmed	PMID: 21359215
Pubmed	PMID: 1786450
Pubmed	PMID: 3410397

)

Disposition

Biological location

Cellular substructure

Extracellular

Non-excretory biofluid

Blood
Saliva

Excreta

Feces
Urine

Tissue

Connective tissue

Adipose tissue

Muscle tissue

Skeletal muscle

Organ

Gland

Adrenal gland

Cell

Hematocyte

Erythrocyte

Neuron

Green lentil

Lentils

Onion-family vegetables

True frog

Roe

Bivalvia

Clam

Cereals and cereal products

Potato bread

Sweet breads

Raisin bread

Herb and spice mixtures

Curry powder

Teas

Herbal tea

Herbal teas

Hibiscus tea

Other alcoholic beverage

Elk
Deer

Equines

Horse

Lagomorphs

Ovis

Sheep (Mutton, Lamb)

Caprae

Domestic goat

Coffee and coffee products

Coffee

Milk and milk products

Fermented milk products

Eggs

Confectioneries

Other confectioneries

Honey

Candies

Liquorice

Baking goods

Seasonings

Vinegar
Salt

Substitutes

Wrappers

Wonton wrapper

Fats and oils

Animal fats

Vegetable fats

Cocoa and cocoa products

Cocoa products

Soy

Soy products

Soy bean

Dishes

Other dishes

Baked beans

Snack foods

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Thiamine metabolism

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	248 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	500 mg/mL	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M-H]-	MetCCS_train_neg	160.3	30932474
[M+H]+	MetCCS_test_pos	162.373	30932474

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.015 g/L	ALOGPS
logP	-2.1	ALOGPS
logP	-3.1	ChemAxon
logS	-4.3	ALOGPS
pKa (Strongest Acidic)	15.5	ChemAxon
pKa (Strongest Basic)	5.54	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	75.91 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	73.4 m³·mol⁻¹	ChemAxon
Polarizability	28.14 Å³	ChemAxon
Number of Rings	2	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
AllCCS	[M+H]+	158.597	32859911
AllCCS	[M-H]-	163.755	32859911
DeepCCS	[M+H]+	161.241	30932474
DeepCCS	[M-H]-	158.883	30932474
DeepCCS	[M-2H]-	192.234	30932474
DeepCCS	[M+Na]+	167.352	30932474

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Thiamine	CC1=C(CCO)SC=[N+]1CC1=CN=C(C)N=C1N	3535.8	Standard polar	33892256
Thiamine	CC1=C(CCO)SC=[N+]1CC1=CN=C(C)N=C1N	2426.3	Standard non polar	33892256
Thiamine	CC1=C(CCO)SC=[N+]1CC1=CN=C(C)N=C1N	2498.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Thiamine,1TMS,isomer #1	CC1=NC=C(C[N+]2=CSC(CCO[Si](C)(C)C)=C2C)C(N)=N1	2471.7	Semi standard non polar	33892256
Thiamine,1TMS,isomer #2	CC1=NC=C(C[N+]2=CSC(CCO)=C2C)C(N[Si](C)(C)C)=N1	2549.4	Semi standard non polar	33892256
Thiamine,2TMS,isomer #1	CC1=NC=C(C[N+]2=CSC(CCO[Si](C)(C)C)=C2C)C(N[Si](C)(C)C)=N1	2502.4	Semi standard non polar	33892256
Thiamine,2TMS,isomer #1	CC1=NC=C(C[N+]2=CSC(CCO[Si](C)(C)C)=C2C)C(N[Si](C)(C)C)=N1	2467.2	Standard non polar	33892256
Thiamine,2TMS,isomer #1	CC1=NC=C(C[N+]2=CSC(CCO[Si](C)(C)C)=C2C)C(N[Si](C)(C)C)=N1	3264.5	Standard polar	33892256
Thiamine,2TMS,isomer #2	CC1=NC=C(C[N+]2=CSC(CCO)=C2C)C(N([Si](C)(C)C)[Si](C)(C)C)=N1	2540.1	Semi standard non polar	33892256
Thiamine,2TMS,isomer #2	CC1=NC=C(C[N+]2=CSC(CCO)=C2C)C(N([Si](C)(C)C)[Si](C)(C)C)=N1	2549.2	Standard non polar	33892256
Thiamine,2TMS,isomer #2	CC1=NC=C(C[N+]2=CSC(CCO)=C2C)C(N([Si](C)(C)C)[Si](C)(C)C)=N1	3162.5	Standard polar	33892256
Thiamine,3TMS,isomer #1	CC1=NC=C(C[N+]2=CSC(CCO[Si](C)(C)C)=C2C)C(N([Si](C)(C)C)[Si](C)(C)C)=N1	2514.5	Semi standard non polar	33892256
Thiamine,3TMS,isomer #1	CC1=NC=C(C[N+]2=CSC(CCO[Si](C)(C)C)=C2C)C(N([Si](C)(C)C)[Si](C)(C)C)=N1	2583.7	Standard non polar	33892256
Thiamine,3TMS,isomer #1	CC1=NC=C(C[N+]2=CSC(CCO[Si](C)(C)C)=C2C)C(N([Si](C)(C)C)[Si](C)(C)C)=N1	2946.7	Standard polar	33892256
Thiamine,1TBDMS,isomer #1	CC1=NC=C(C[N+]2=CSC(CCO[Si](C)(C)C(C)(C)C)=C2C)C(N)=N1	2740.7	Semi standard non polar	33892256
Thiamine,1TBDMS,isomer #2	CC1=NC=C(C[N+]2=CSC(CCO)=C2C)C(N[Si](C)(C)C(C)(C)C)=N1	2747.4	Semi standard non polar	33892256
Thiamine,2TBDMS,isomer #1	CC1=NC=C(C[N+]2=CSC(CCO[Si](C)(C)C(C)(C)C)=C2C)C(N[Si](C)(C)C(C)(C)C)=N1	2905.4	Semi standard non polar	33892256
Thiamine,2TBDMS,isomer #1	CC1=NC=C(C[N+]2=CSC(CCO[Si](C)(C)C(C)(C)C)=C2C)C(N[Si](C)(C)C(C)(C)C)=N1	2897.6	Standard non polar	33892256
Thiamine,2TBDMS,isomer #1	CC1=NC=C(C[N+]2=CSC(CCO[Si](C)(C)C(C)(C)C)=C2C)C(N[Si](C)(C)C(C)(C)C)=N1	3365.0	Standard polar	33892256
Thiamine,2TBDMS,isomer #2	CC1=NC=C(C[N+]2=CSC(CCO)=C2C)C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=N1	2927.6	Semi standard non polar	33892256
Thiamine,2TBDMS,isomer #2	CC1=NC=C(C[N+]2=CSC(CCO)=C2C)C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=N1	2959.6	Standard non polar	33892256
Thiamine,2TBDMS,isomer #2	CC1=NC=C(C[N+]2=CSC(CCO)=C2C)C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=N1	3242.0	Standard polar	33892256
Thiamine,3TBDMS,isomer #1	CC1=NC=C(C[N+]2=CSC(CCO[Si](C)(C)C(C)(C)C)=C2C)C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=N1	3094.1	Semi standard non polar	33892256
Thiamine,3TBDMS,isomer #1	CC1=NC=C(C[N+]2=CSC(CCO[Si](C)(C)C(C)(C)C)=C2C)C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=N1	3195.6	Standard non polar	33892256
Thiamine,3TBDMS,isomer #1	CC1=NC=C(C[N+]2=CSC(CCO[Si](C)(C)C(C)(C)C)=C2C)C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=N1	3187.4	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Thiamine GC-MS (Non-derivatized) - 70eV, Positive	splash10-00e9-3890000000-9f8b525433ab279ad512	2016-09-22	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Thiamine GC-MS (1 TMS) - 70eV, Positive	splash10-00di-9442000000-05ab93d3afb7b6f538e9	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Thiamine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Thiamine GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Thiamine GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Thiamine GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Thiamine Quattro_QQQ 10V, N/A-QTOF (Annotated)	splash10-000i-0109000000-48864f31ba475645654b	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Thiamine Quattro_QQQ 25V, N/A-QTOF (Annotated)	splash10-05o1-9200000000-2ec0f3e9e364cffde16e	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Thiamine Quattro_QQQ 40V, N/A-QTOF (Annotated)	splash10-0aou-9000000000-0184506492d9f5b68b97	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Thiamine LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative-QTOF	splash10-03di-0090000000-872150be83cbd75d8ecf	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Thiamine LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative-QTOF	splash10-0002-0930000000-ecf71c75bdea859139d5	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Thiamine LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative-QTOF	splash10-0002-0900000000-4d9113fdc633fb1ccbb5	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Thiamine LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative-QTOF	splash10-0002-0900000000-4a8016299623af0c3027	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Thiamine LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative-QTOF	splash10-0002-1900000000-773912c9f325c419c77d	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Thiamine LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive-QTOF	splash10-014i-0390000000-95f3ca57c95542bdc7e7	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Thiamine LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive-QTOF	splash10-00di-0900000000-e079d1fc1e06396dc524	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Thiamine LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive-QTOF	splash10-00di-0900000000-ebb16d4f204f291b9a3a	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Thiamine LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive-QTOF	splash10-00e9-4900000000-ad4d4779d76b9edb7ec5	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Thiamine LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive-QTOF	splash10-001i-9600000000-b631eed5be831527fc17	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Thiamine LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positive-QTOF	splash10-00di-0900000000-50f2f613f576814eb627	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Thiamine LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positive-QTOF	splash10-002b-0900000000-2f184bbfec6bc0ef00c6	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Thiamine LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positive-QTOF	splash10-001i-9000000000-35bc744495a2570a565f	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Thiamine LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive-QTOF	splash10-00di-1900000000-d8a7ac327273c32b4524	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Thiamine LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative-QTOF	splash10-0002-0920000000-ca80ef6513c61be5b5e9	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Thiamine LC-ESI-QQ , negative-QTOF	splash10-03di-0090000000-872150be83cbd75d8ecf	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Thiamine 10V, Positive-QTOF	splash10-014i-0190000000-183af2449d1439af9825	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Thiamine 20V, Positive-QTOF	splash10-0a4i-0090000000-2230ebc7c6b73192c26f	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Thiamine 40V, Positive-QTOF	splash10-0002-7920000000-75670df9647a475ca92c	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Thiamine 10V, Negative-QTOF	splash10-03di-3090000000-d0ff9a733629a86b75c7	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Thiamine 20V, Negative-QTOF	splash10-03dj-3690000000-db3f204af490d7e1722e	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Thiamine 40V, Negative-QTOF	splash10-0005-9000000000-5196f2b4daab995967bf	2016-09-12	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Experimental 1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	2012-12-04	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Experimental 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, experimental)	2021-10-10	Wishart Lab	View Spectrum
Experimental 2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	2012-12-05	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane (predicted from logP)
Mitochondria

Biospecimen Locations

Blood
Cerebrospinal Fluid (CSF)
Feces
Saliva
Urine

Tissue Locations

Adipose Tissue
Adrenal Gland
Brain
Erythrocyte
Fibroblasts
Intestine
Kidney
Liver
Neuron
Placenta
Skeletal Muscle
Testis

Pathways

Name	SMPDB/PathBank	KEGG
Thiamine Metabolism

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.34 (0.14-0.79) uM	Newborn (0-30 days old)	Both	Normal	Geigy Scientific ...	details
Blood	Detected and Quantified	0.16 (0.06-0.41) uM	Children (1-13 years old)	Both	Normal	Geigy Scientific ...	details
Blood	Detected and Quantified	0.096 +/- 0.018 uM	Adult (>18 years old)	Not Specified	Normal	11684545	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Blood	Detected and Quantified	0.12 (0.094-0.280) uM	Adult (>18 years old)	Female	Normal	Geigy Scientific ...	details
Blood	Detected and Quantified	0.050-0.120 uM	Adult (>18 years old)	Both	Normal	Molecular You	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.006 (0.005 - 0.007) uM	Adult (>18 years old)	Both	Normal	Geigy Scientific ...	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.141 +/- 0.0543 uM	Adult (>18 years old)	Both	Normal	1538220	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.0487 +/- 0.00275 uM	Adult (>18 years old)	Not Specified	Normal	182198	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	29808030	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	27543620	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	25037050	details
Saliva	Detected and Quantified	0.247 +/- 0.006 uM	Adult (>18 years old)	Both	Normal	Zerihun T. Dame, ...	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Urine	Detected and Quantified	0.12 +/- 0.09 umol/mmol creatinine	Children (1-13 years old)	Both	Normal	Geigy Scientific ...	details
Urine	Detected and Quantified	0.02 +/- 0.01 umol/mmol creatinine	Newborn (0-30 days old)	Both	Normal	Geigy Scientific ...	details
Urine	Detected and Quantified	0.22 (0.20-0.60) umol/mmol creatinine	Adult (>18 years old)	Both	Normal	Geigy Scientific ...	details
Urine	Detected and Quantified	0.132 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	15051849	details
Urine	Detected and Quantified	0.0283 +/- 0.0191 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	20502474	details
Urine	Detected and Quantified	0.0511 +/- 0.0255 umol/mmol creatinine	Children (1 - 13 years old)	Both	Normal	20576202	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.035 +/- 0.006 uM	Elderly (>65 years old)	Both	Hemodialysis	11684545	details
Blood	Detected and Quantified	0.18 +/- 0.066 uM	Adult (>18 years old)	Both	Friedreich's ataxia	1538220	details
Blood	Detected and Quantified	0.17 +/- 0.051 uM	Adult (>18 years old)	Both	Olivopontocerebellar atrophy (OPCA)	1538220	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.115 +/- 0.0464 uM	Adult (>18 years old)	Both	Friedreich's ataxia	1538220	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.0902 +/- 0.0411 uM	Adult (>18 years old)	Both	Olivopontocerebellar atrophy (OPCA)	1538220	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.02 +/- 0.00 uM	Adult (>18 years old)	Not Specified	Alcoholism	182198	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.01 +/- 0.00 uM	Adult (>18 years old)	Not Specified	Alcoholism	182198	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.09 +/- 0.01 uM	Adult (>18 years old)	Not Specified	Olivopontocerebellar atrophy (OPCA)	11383938	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.06 +/- 0.01 uM	Adult (>18 years old)	Not Specified	Autosomal recessive spastic ataxia of Charlevoix-Saguena	11383938	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.1 +/- 0.01 uM	Not Specified	Not Specified	Friedreich's ataxia	11383938	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	27015276	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	25037050	details

Associated Disorders and Diseases

Disease References

Hemodialysis
Hung SC, Hung SH, Tarng DC, Yang WC, Chen TW, Huang TP: Thiamine deficiency and unexplained encephalopathy in hemodialysis and peritoneal dialysis patients. Am J Kidney Dis. 2001 Nov;38(5):941-7. [PubMed:11684545 ]
Friedreich's ataxia
Pedraza OL, Botez MI: Thiamine status in inherited degenerative ataxias. J Neurol Neurosurg Psychiatry. 1992 Feb;55(2):136-7. [PubMed:1538220 ] Botez MI, Young SN: Biogenic amine metabolites and thiamine in cerebrospinal fluid in heredo-degenerative ataxias. Can J Neurol Sci. 2001 May;28(2):134-40. [PubMed:11383938 ]
Olivopontocerebral atrophy
Pedraza OL, Botez MI: Thiamine status in inherited degenerative ataxias. J Neurol Neurosurg Psychiatry. 1992 Feb;55(2):136-7. [PubMed:1538220 ] Botez MI, Young SN: Biogenic amine metabolites and thiamine in cerebrospinal fluid in heredo-degenerative ataxias. Can J Neurol Sci. 2001 May;28(2):134-40. [PubMed:11383938 ]
Alcoholism
Dastur DK, Santhadevi N, Quadros EV, Avari FC, Wadia NH, Desai MN, Bharucha EP: The B-vitamins in malnutrition with alcoholism. A model of intervitamin relationships. Br J Nutr. 1976 Sep;36(2):143-59. [PubMed:182198 ]
Hereditary spastic paraplegia
Botez MI, Young SN: Biogenic amine metabolites and thiamine in cerebrospinal fluid in heredo-degenerative ataxias. Can J Neurol Sci. 2001 May;28(2):134-40. [PubMed:11383938 ]
Colorectal cancer
Sinha R, Ahn J, Sampson JN, Shi J, Yu G, Xiong X, Hayes RB, Goedert JJ: Fecal Microbiota, Fecal Metabolome, and Colorectal Cancer Interrelations. PLoS One. 2016 Mar 25;11(3):e0152126. doi: 10.1371/journal.pone.0152126. eCollection 2016. [PubMed:27015276 ] Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]

Associated OMIM IDs

229300 (Friedreich's ataxia)
182601 (Hereditary spastic paraplegia)
114500 (Colorectal cancer)

External Links

DrugBank ID

DB00152

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Thiamine

METLIN ID

Not Available

PubChem Compound

1130

PDB ID

Not Available

ChEBI ID

18385

Food Biomarker Ontology

Not Available

VMH ID

THM

MarkerDB ID

MDB00000114

Good Scents ID

Not Available

References

Synthesis Reference

Sugimoto, Hirohiko; Ishiba, Teruyuki; Sato, Tomohiro; Nakai, Hiroshi; Hirai, Kentaro. Novel S-alkylation products from "isolated thiamin ylide" via thiaminium neothiaminthiolate ion pair. Journal of Organic Chemistry (1990), 55(2), 467-70.

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Dutta B, Huang W, Molero M, Kekuda R, Leibach FH, Devoe LD, Ganapathy V, Prasad PD: Cloning of the human thiamine transporter, a member of the folate transporter family. J Biol Chem. 1999 Nov 5;274(45):31925-9. [PubMed:10542220 ]
Bellazzi R, Guglielmann R, Ironi L, Patrini C: A hybrid input-output approach to model metabolic systems: an application to intracellular thiamine kinetics. J Biomed Inform. 2001 Aug;34(4):221-48. [PubMed:11977806 ]
Pietrzak I, Baczyk K: Comparison of the thiamine level in blood and erythrocyte transketolase activity in hemodialyzed and nondialyzed patients during recombinant human erythropoietin therapy. Miner Electrolyte Metab. 1997;23(3-6):277-82. [PubMed:9387133 ]
Singleton CK, Martin PR: Molecular mechanisms of thiamine utilization. Curr Mol Med. 2001 May;1(2):197-207. [PubMed:11899071 ]
Sato Y, Nakagawa M, Higuchi I, Osame M, Naito E, Oizumi K: Mitochondrial myopathy and familial thiamine deficiency. Muscle Nerve. 2000 Jul;23(7):1069-75. [PubMed:10883001 ]
Mastrogiacoma F, Bettendorff L, Grisar T, Kish SJ: Brain thiamine, its phosphate esters, and its metabolizing enzymes in Alzheimer's disease. Ann Neurol. 1996 May;39(5):585-91. [PubMed:8619543 ]
Molina JA, Jimenez-Jimenez FJ, Hernanz A, Fernandez-Vivancos E, Medina S, de Bustos F, Gomez-Escalonilla C, Sayed Y: Cerebrospinal fluid levels of thiamine in patients with Alzheimer's disease. J Neural Transm (Vienna). 2002 Jul;109(7-8):1035-44. [PubMed:12111441 ]
Pietrzak I, Baczyk K, Kubiak W: Recombinant human erythropoietin administration improves thiamine content in blood and erythrocytes transketolase activity in pre-dialyzed patients. Ann Univ Mariae Curie Sklodowska Med. 1994;48 Suppl 3:29-37. [PubMed:8192530 ]
Valerio G, Franzese A, Poggi V, Patrini C, Laforenza U, Tenore A: Lipophilic thiamine treatment in long-standing insulin-dependent diabetes mellitus. Acta Diabetol. 1999 Jun;36(1-2):73-6. [PubMed:10436256 ]
Herve C, Beyne P, Delacoux E: Determination of thiamine and its phosphate esters in human erythrocytes by high-performance liquid chromatography with isocratic elution. J Chromatogr B Biomed Appl. 1994 Mar 4;653(2):217-20. [PubMed:8205249 ]
Losa R, Sierra MI, Fernandez A, Blanco D, Buesa JM: Determination of thiamine and its phosphorylated forms in human plasma, erythrocytes and urine by HPLC and fluorescence detection: a preliminary study on cancer patients. J Pharm Biomed Anal. 2005 Apr 29;37(5):1025-9. [PubMed:15862682 ]
Pietrzak I, Baczyk K, Mlynarczyk M: [The influence of intermittent peritoneal dialysis on free and total thiamine concentration in plasma and erythrocytes of patients with end stage renal disease]. Pol Arch Med Wewn. 1994;92 Spec No:31-6. [PubMed:7731897 ]
Pedraza OL, Botez MI: Thiamine status in inherited degenerative ataxias. J Neurol Neurosurg Psychiatry. 1992 Feb;55(2):136-7. [PubMed:1538220 ]
Vinogradov VV, Tarasov IuA, Tishin VS, Bogdanovich VI, Spas VV: [Thiamine prevention of the corticosteroid reaction afer surgery]. Probl Endokrinol (Mosk). 1981 May-Jun;27(3):11-6. [PubMed:7291135 ]
Tanaka T, Sohmiya K, Kono T, Terasaki F, Horie R, Ohkaru Y, Muramatsu M, Takai S, Miyazaki M, Kitaura Y: Thiamine attenuates the hypertension and metabolic abnormalities in CD36-defective SHR: uncoupling of glucose oxidation from cellular entry accompanied with enhanced protein O-GlcNAcylation in CD36 deficiency. Mol Cell Biochem. 2007 May;299(1-2):23-35. [PubMed:16645728 ]
Bettendorff L, Mastrogiacomo F, Kish SJ, Grisar T: Thiamine, thiamine phosphates, and their metabolizing enzymes in human brain. J Neurochem. 1996 Jan;66(1):250-8. [PubMed:8522961 ]
Lee DC, Chu J, Satz W, Silbergleit R: Low plasma thiamine levels in elder patients admitted through the emergency department. Acad Emerg Med. 2000 Oct;7(10):1156-9. [PubMed:11015250 ]
Shimon I, Almog S, Vered Z, Seligmann H, Shefi M, Peleg E, Rosenthal T, Motro M, Halkin H, Ezra D: Improved left ventricular function after thiamine supplementation in patients with congestive heart failure receiving long-term furosemide therapy. Am J Med. 1995 May;98(5):485-90. [PubMed:7733128 ]
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 ]

Enzymes

Enzyme Details

1. Thiamin pyrophosphokinase 1

General function:: Involved in thiamin diphosphokinase activity
Specific function:: Catalyzes the phosphorylation of thiamine to thiamine pyrophosphate. Can also catalyze the phosphorylation of pyrithiamine to pyrithiamine pyrophosphate.
Gene Name:: TPK1
Uniprot ID:: Q9H3S4
Molecular weight:: 27265.05

Reactions

Adenosine triphosphate + Thiamine → Adenosine monophosphate + Thiamine pyrophosphate	details

Enzyme Details

2. Transketolase

General function:: Involved in catalytic activity
Specific function:: Catalyzes the transfer of a two-carbon ketol group from a ketose donor to an aldose acceptor, via a covalent intermediate with the cofactor thiamine pyrophosphate.
Gene Name:: TKT
Uniprot ID:: P29401
Molecular weight:: 67876.95

Enzyme Details

3. Thiamine-triphosphatase

General function:: Involved in adenylate cyclase activity
Specific function:: Hydrolase highly specific for thiamine triphosphate (ThTP).
Gene Name:: THTPA
Uniprot ID:: Q9BU02
Molecular weight:: 25565.685

Enzyme Details

4. Thiamine transporter 1

General function:: Involved in folic acid binding
Specific function:: High-affinity transporter for the intake of thiamine.
Gene Name:: SLC19A2
Uniprot ID:: O60779
Molecular weight:: 55399.49

Enzyme Details

5. Thiamine transporter THTR-1

General function:: Involved in folic acid binding
Specific function:: Not Available
Gene Name:: SLC19A2
Uniprot ID:: Q7Z7J1
Molecular weight:: 7567.7

Enzyme Details

6. Solute carrier family 19 thiamine transporter member 2

General function:: Not Available
Specific function:: Not Available
Gene Name:: SLC19A2
Uniprot ID:: B0FBR7
Molecular weight:: 1539.7

Enzyme Details

7. Solute carrier family 19 (Thiamine transporter), member 2

General function:: Involved in folic acid binding
Specific function:: Not Available
Gene Name:: SLC19A2
Uniprot ID:: Q5TIE1
Molecular weight:: 51277.0

Enzyme Details

8. 14 kDa phosphohistidine phosphatase

General function:: Involved in phosphohistidine phosphatase activity
Specific function:: Exhibits phosphohistidine phosphatase activity.
Gene Name:: PHPT1
Uniprot ID:: Q9NRX4
Molecular weight:: Not Available

Showing metabocard for Thiamine (HMDB0000235)

MOL for HMDB0000235 (Thiamine)

3D MOL for HMDB0000235 (Thiamine)

3D SDF for HMDB0000235 (Thiamine)

3D-SDF for HMDB0000235 (Thiamine)

PDB for HMDB0000235 (Thiamine)

3D PDB for HMDB0000235 (Thiamine)

SMILES for HMDB0000235 (Thiamine)

INCHI for HMDB0000235 (Thiamine)

Structure for HMDB0000235 (Thiamine)

3D Structure for HMDB0000235 (Thiamine)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes

Reactions