NP-MRD: Showing NP-Card for Thiamine (NP0001167)

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Record Information

Version

2.0

Created at

2005-11-16 15:48:42 UTC

Updated at

2021-07-01 14:27:34 UTC

NP-MRD ID

NP0001167

Secondary Accession Numbers

None

Natural Product 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>
NP0001167

> <DATABASE_NAME>
NP-MRD

> <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

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 cation	ChEBI
Thiamine ion	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	HMDB
Thiamine mononitrate	HMDB
Vitamin b 1	HMDB

Chemical Formula

C₁₂H₁₇N₄OS

Average Mass

265.3550 Da

Monoisotopic Mass

265.11231 Da

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

59-43-8

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

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, simulated)	v.dorna83@yahoo.com	Not Available	Not Available	2021-08-03	View Spectrum

Species

Species of Origin

Species Name	Source	Reference
Abelmoschus esculentus	FooDB	DTU Food
Abramis brama	FooDB	DTU Food
Acipenser	FooDB	USDA
Acipenseridae	FooDB	DTU Food
Actinidia chinensis	FooDB	DTU Food
Agaricus bisporus	FooDB	DTU Food
Agave	FooDB	USDA
Alhagi persarum	LOTUS Database	35616633
Allium ampeloprasum	FooDB	USDA
Allium ascalonicum	FooDB	USDA
Allium cepa	FooDB	USDA
Allium cepa L.	FooDB	DTU Food
Allium fistulosum	FooDB	USDA
Allium sativum	FooDB	DTU Food
Allium schoenoprasum	FooDB	DTU Food
Allium tuberosum	FooDB	USDA
Alosa sapidissima	FooDB	USDA
Amaranthus	FooDB	USDA
Anacardium occidentale	FooDB	DTU Food
Ananas comosus	FooDB	DTU Food
Anarhichas lupus	FooDB	DTU Food
Anatidae	FooDB	DTU Food
Anethum graveolens	FooDB	DTU Food
Anguilla	FooDB	USDA
Anguilliformes	FooDB	DTU Food
Annona cherimola	FooDB	DTU Food
Annona muricata	FooDB	USDA
Annona reticulata	FooDB	USDA
Anoplopoma fimbria	FooDB	USDA
Anthriscus cerefolium	FooDB	DTU Food
Apium graveolens	FooDB	DTU Food
Apium graveolens var. dulce	FooDB	USDA
Apium graveolens var. rapaceum	FooDB	DTU Food
Apium graveolens var. secalinum	FooDB	DTU Food
Aplodinotus grunniens	FooDB	USDA
Arachis hypogaea	FooDB	DTU Food
Archosargus probatocephalus	FooDB	USDA
Arctium lappa	FooDB	USDA
Armoracia rusticana	FooDB	DTU Food
Artemia salina	LOTUS Database	35616633
Artocarpus altilis	FooDB	USDA
Artocarpus heterophyllus	FooDB	USDA
Asparagus officinalis	FooDB	DTU Food
Astacidea	FooDB	DTU Food
Auricularia auricula-judae	FooDB	USDA
Auricularia polytricha	FooDB	USDA
Avena sativa L.	FooDB	DTU Food
Averrhoa carambola	FooDB	DTU Food
Basella alba	FooDB	USDA
Belone belone	FooDB	DTU Food
Benincasa hispida	FooDB	USDA
Bertholletia excelsa	FooDB	DTU Food
Beta vulgaris	FooDB	USDA
Beta vulgaris ssp. cicla	FooDB	DTU Food
Bison bison	FooDB	USDA
Bivalvia	FooDB	USDA
Borago officinalis	FooDB	USDA
Bos taurus	FooDB	DTU Food
Bos taurus X Bison bison	FooDB	USDA
Brachyura	FooDB	DTU Food
Brassica alboglabra	FooDB	USDA
Brassica juncea	FooDB	USDA
Brassica napus	FooDB	DTU Food
Brassica napus var. napus	FooDB	DTU Food
Brassica oleracea	FooDB	DTU Food
Brassica oleracea var. botrytis	FooDB	DTU Food
Brassica oleracea var. capitata	FooDB	USDA
Brassica oleracea var. gemmifera	FooDB	DTU Food
Brassica oleracea var. gongylodes	FooDB	DTU Food
Brassica oleracea var. italica	FooDB	DTU Food
Brassica oleracea var. sabauda	FooDB	DTU Food
Brassica rapa	FooDB	DTU Food
Brassica rapa ssp. chinensis	FooDB	DTU Food
Brassica rapa var. pekinensis	FooDB	USDA
Brassica rapa var. rapa	FooDB	DTU Food
Brosimum alicastrum	FooDB	USDA
Brosme brosme	FooDB	USDA
Bubalus bubalis	FooDB	USDA
Buccinidae	FooDB	USDA
Byrsonima crassifolia	FooDB	USDA
Cajanus cajan	FooDB	USDA
Callinectes sapidus	FooDB	USDA
Canarium ovatum	FooDB	USDA
Cancer magister	FooDB	USDA
Cantharellus cibarius	FooDB	DTU Food
Capparis spinosa	FooDB	USDA
Capra aegagrus hircus	FooDB	USDA
Capsicum annuum	FooDB	All-Creatures
Carica papaya L.	FooDB	DTU Food
Caridea	FooDB	DTU Food
Carthamus tinctorius	FooDB	DTU Food
Carum carvi	FooDB	USDA
Carya	FooDB	USDA
Carya illinoinensis	FooDB	DTU Food
Castanea	FooDB	DTU Food
Castanea crenata	FooDB	USDA
Castanea mollissima	FooDB	USDA
Castanea sativa	FooDB	USDA
Catostomus commersonii	FooDB	USDA
Celosia cristada	KNApSAcK Database	22123792
Ceratonia siliqua	FooDB	USDA
Cervidae	FooDB	USDA
Cervus canadensis	FooDB	USDA
Chamaemelum nobile	FooDB	USDA
Chamerion angustifolium	FooDB	USDA
Chanos chanos	FooDB	USDA
Chenopodium album	FooDB	USDA
Chenopodium quinoa	FooDB	USDA
Chionoecetes opilio	FooDB	USDA
Chondrus crispus	FooDB	USDA
Chrysanthemum coronarium	FooDB	USDA
Cicer arietinum	FooDB	DTU Food
Cichlidae	FooDB	USDA
Cichorium endivia	FooDB	DTU Food
Cichorium intybus	FooDB	DTU Food
Cinnamomum	FooDB	DTU Food
Cirsium	FooDB	DTU Food
Citrullus lanatus	FooDB	DTU Food
Citrus ×limon (L.) Burm. f. (pro sp.)	FooDB	DTU Food
Citrus aurantiifolia	FooDB	DTU Food
Citrus latifolia	FooDB	USDA
Citrus limon	FooDB	DTU Food
Citrus maxima	FooDB	USDA
Citrus paradisi	FooDB	DTU Food
Citrus reticulata	FooDB	DTU Food
Citrus X sinensis (L.) Osbeck (pro. sp.)	FooDB	DTU Food
Clinocardium nuttallii	FooDB	USDA
Clupea harengus harengus	FooDB	USDA
Clupea pallasii	FooDB	USDA
Clupeinae	FooDB	DTU Food
Cocos nucifera	FooDB	DTU Food
Coffea arabica L.	FooDB	DTU Food
Coffea canephora	FooDB	DTU Food
Colocasia esculenta	FooDB	USDA
Columba	FooDB	USDA
Columbidae	FooDB	DTU Food
Corchorus olitorius	FooDB	USDA
Coregonus	FooDB	DTU Food
Coregonus artedi	FooDB	USDA
Coregonus nasus	FooDB	USDA
Coriandrum sativum L.	FooDB	DTU Food
Corylus	FooDB	DTU Food
Corylus avellana	FooDB	USDA
Crassostrea gigas	FooDB	USDA
Crassostrea virginica	FooDB	USDA
Crocus sativus	FooDB	USDA
Cucumis melo	FooDB	DTU Food
Cucumis metuliferus	FooDB	USDA
Cucumis sativus L.	FooDB	DTU Food
Cucurbita	FooDB	DTU Food
Cucurbita maxima	FooDB	CalorieSlism
Cucurbita moschata	FooDB	USDA
Cuminum cyminum	FooDB	USDA
Curcuma longa	FooDB	USDA
Cyclopteridae	FooDB	DTU Food
Cydonia oblonga	FooDB	DTU Food
Cymbopogon citratus	FooDB	USDA
Cynara cardunculus	FooDB	USDA
Cynara scolymus	FooDB	DTU Food
Cyprinus carpio	FooDB	USDA
Dallia pectoralis	FooDB	USDA
Daucus carota	FooDB	USDA
Daucus carota ssp. sativus	FooDB	DTU Food
Dimocarpus longan	FooDB	USDA
Dioscorea	FooDB	DTU Food
Dioscorea pentaphylla	FooDB	USDA
Diospyros	FooDB	DTU Food
Diospyros kaki	FooDB	USDA
Dromaius novaehollandiae	FooDB	USDA
Durio zibethinus	FooDB	USDA
Dysphania ambrosioides	FooDB	USDA
Elaeis	FooDB	DTU Food
Elettaria cardamomum	FooDB	USDA
Engraulidae	FooDB	DTU Food
Engraulis encrasicolus	FooDB	USDA
Enteroctopus dofleini	FooDB	USDA
Epinephelus	FooDB	USDA
Equus caballus	FooDB	USDA
Eragrostis tef	FooDB	USDA
Eriobotrya japonica	FooDB	DTU Food
Eruca vesicaria subsp. Sativa	FooDB	USDA
Esox lucius	FooDB	DTU Food
Eucheuma	FooDB	DTU Food
Eugenia uniflora	FooDB	USDA
Eutrema japonicum	FooDB	USDA
Fagopyrum esculentum	FooDB	DTU Food
Fagus	FooDB	USDA
Feijoa sellowiana	FooDB	USDA
Ficus carica	FooDB	DTU Food
Foeniculum vulgare	FooDB	DTU Food
Fragaria x ananassa	FooDB	DTU Food
Gadiformes	FooDB	DTU Food
Gadus	FooDB	DTU Food
Gadus macrocephalus	FooDB	USDA
Gadus morhua	FooDB	USDA
Gallus gallus	FooDB	DTU Food
Gastropoda	FooDB	DTU Food
Ginkgo biloba	FooDB	USDA
Glycine max	FooDB	DTU Food
Gossypium	FooDB	DTU Food
Grifola frondosa	FooDB	USDA
Hedysarum alpinum	FooDB	USDA
Helianthus annuus L.	FooDB	DTU Food
Helianthus tuberosus	FooDB	DTU Food
Hibiscus sabbariffa	FooDB	USDA
Hippoglossus	FooDB	USDA
Hippoglossus hippoglossus	FooDB	DTU Food
Hippoglossus stenolepis	FooDB	USDA
Hippophae rhamnoides	KNApSAcK Database	22123792
Homarus americanus	FooDB	USDA
Homo sapiens	LOTUS Database	35616633
Hoplostethus atlanticus	FooDB	USDA
Hordeum vulgare	FooDB	DTU Food
Ictalurus punctatus	FooDB	USDA
Illicium verum	FooDB	USDA
Ipomoea batatas	FooDB	DTU Food
Juglans	FooDB	DTU Food
Juglans cinerea	FooDB	USDA
Juglans nigra L.	FooDB	DTU Food
Juglans regia	FooDB	USDA
Katsuwonus pelamis	FooDB	USDA
Lablab purpureus	FooDB	USDA
Lactuca sativa	FooDB	DG. Criossby. The Organic Constituents of Food. I. Lettuce. J. Food Sci. 1963, 28(3):347-355
Lagenaria siceraria	FooDB	USDA
Lagopus muta	FooDB	DTU Food
Laminaria	FooDB	USDA
Leiostomus xanthurus	FooDB	USDA
Lens culinaris	FooDB	DTU Food
Lentinus edodes	FooDB	USDA
Lepidium sativum	FooDB	DTU Food
Lepomis gibbosus	FooDB	USDA
Leporidae	FooDB	DTU Food
Lepus timidus	FooDB	DTU Food
Limanda limanda	FooDB	DTU Food
Linum usitatissimum	FooDB	DTU Food
Litchi chinensis	FooDB	DTU Food
Lophius piscatorius	FooDB	USDA
Lopholatilus chamaeleonticeps	FooDB	USDA
Lota lota	FooDB	DTU Food
Lupinus	FooDB	USDA
Lupinus albus	FooDB	USDA
Lutjanidae	FooDB	USDA
Lycium chinense	KNApSAcK Database	22123792
Macadamia	FooDB	USDA
Macadamia tetraphylla	FooDB	USDA
Malpighia emarginata	FooDB	USDA
Malus	FooDB	DTU Food
Malus pumila	FooDB	DTU Food
Mangifera indica	KNApSAcK Database	22123792
Manihot esculenta	FooDB	DTU Food
Manilkara zapota	FooDB	USDA
Maranta arundinacea	FooDB	USDA
Matricaria recutita	FooDB	USDA
Matteuccia struthiopteris	LOTUS Database	35616633
Medicago sativa	KNApSAcK Database	22123792
Melanogrammus aeglefinus	FooDB	DTU Food
Meleagris gallopavo	FooDB	DTU Food
Mentha spicata	FooDB	USDA
Mentha x piperita	FooDB	USDA
Merlangius merlangus	FooDB	DTU Food
Micromesistius poutassou	FooDB	DTU Food
Micropogonias undulatus	FooDB	USDA
Microstomus kitt	FooDB	DTU Food
Molva molva	FooDB	DTU Food
Momordica charantia	FooDB	USDA
Morchellaceae	FooDB	USDA
Morone saxatilis	FooDB	USDA
Morus alba	KNApSAcK Database	22123792
Mugil cephalus	FooDB	USDA
Mus musculus	LOTUS Database	35616633
Musa acuminata	FooDB	USDA
Musa x paradisiaca	FooDB	DTU Food
Myoxocephalus	FooDB	USDA
Myristica fragrans	FooDB	DTU Food
Mytilidae	FooDB	DTU Food
Mytilus edulis	FooDB	USDA
Nelumbo	FooDB	USDA
Nephelium lappaceum	FooDB	USDA
Nephropidae	FooDB	DTU Food
Nephrops norvegicus	FooDB	DTU Food
Numida meleagris	FooDB	USDA
Nuphar lutea	FooDB	USDA
Ocimum basilicum	FooDB	USDA
Octopus vulgaris	FooDB	DTU Food
Olea europaea	FooDB	DTU Food
Oncorhynchus	FooDB	USDA
Oncorhynchus gorbuscha	FooDB	USDA
Oncorhynchus keta	FooDB	USDA
Oncorhynchus kisutch	FooDB	USDA
Oncorhynchus mykiss	FooDB	DTU Food
Oncorhynchus nerka	FooDB	USDA
Oncorhynchus tshawytscha	FooDB	USDA
Ophiocordyceps sinensis	Fungi	KNApSAcK
Ophiodon elongatus	FooDB	USDA
Opuntia	FooDB	DTU Food
Opuntia cochenillifera	FooDB	USDA
Opuntia macrorhiza	FooDB	USDA
Origanum majorana	FooDB	USDA
Origanum vulgare	FooDB	USDA
Origanum X majoricum	FooDB	USDA
Oryctolagus	FooDB	USDA
Oryza rufipogon	FooDB	USDA
Oryza sativa	FooDB	DTU Food
Osmeridae	FooDB	USDA
Osmerus mordax	FooDB	USDA
Ovis aries	FooDB	DTU Food
Pachyrhizus erosus	FooDB	USDA
Palinuridae	FooDB	USDA
Panax ginseng	KNApSAcK Database	22123792
Panicum miliaceum	FooDB	DTU Food
Papaver	FooDB	DTU Food
Paralithodes camtschaticus	FooDB	USDA
Parastichopus californicus	FooDB	USDA
Passiflora edulis	FooDB	DTU Food
Pastinaca sativa	FooDB	DTU Food
Pectinidae	FooDB	USDA
Pediomelum esculentum	FooDB	USDA
Peprilus triacanthus	FooDB	USDA
Perciformes	FooDB	DTU Food
Percoidei	FooDB	USDA
Perilla frutescens var.arguta	KNApSAcK Database	22123792
Persea americana	FooDB	DTU Food
Petasites japonicus	FooDB	USDA
Petroselinum crispum	FooDB	DTU Food
Phaseolus lunatus	FooDB	USDA
Phaseolus vulgaris	FooDB	DTU Food
Phasianidae	FooDB	USDA
Phasianus colchicus	FooDB	USDA
Phoenix dactylifera	FooDB	DTU Food
Phragmites communis	KNApSAcK Database	22123792
Phyllostachys edulis	FooDB	DTU Food
Physalis	FooDB	DTU Food
Pimenta dioica	FooDB	USDA
Pimpinella anisum	FooDB	USDA
Pinus	FooDB	DTU Food
Pinus edulis	FooDB	USDA
Piper nigrum L.	FooDB	DTU Food
Pistacia vera	FooDB	DTU Food
Pisum sativum	FooDB	DTU Food
Pleuronectidae	FooDB	DTU Food
Pleuronectiformes	FooDB	DTU Food
Pleurotus ostreatus	FooDB	DTU Food
Pollachius	FooDB	DTU Food
Pollachius pollachius	FooDB	USDA
Polygonum alpinum	FooDB	USDA
Pomatomus saltatrix	FooDB	USDA
Portulaca oleracea	FooDB	USDA
Pouteria sapota	FooDB	USDA
Prunus armeniaca	FooDB	DTU Food
Prunus avium L.	FooDB	DTU Food
Prunus domestica	FooDB	DTU Food
Prunus dulcis	FooDB	DTU Food
Prunus persica	FooDB	DTU Food
Prunus persica var. nucipersica	FooDB	DTU Food
Prunus persica var. persica	FooDB	USDA
Prunus virginiana	FooDB	USDA
Psidium cattleianum	FooDB	USDA
Psidium guajava	FooDB	DTU Food
Psophocarpus tetragonolobus	FooDB	USDA
Punica granatum	FooDB	DTU Food
Pyrus communis	FooDB	DTU Food
Pyrus pyrifolia	FooDB	USDA
Quercus	FooDB	USDA
Ranidae	FooDB	DTU Food
Raphanus sativus	FooDB	USDA
Raphanus sativus var. longipinnatus	FooDB	DTU Food
Reinhardtius hippoglossoides	FooDB	DTU Food
Rheum rhabarbarum	FooDB	DTU Food
Ribes nigrum	FooDB	DTU Food
Ribes rubrum	FooDB	DTU Food
Ribes uva-crispa	FooDB	DTU Food
Rosa	FooDB	DTU Food
Rubus chamaemorus	FooDB	USDA
Rubus spectabilis	FooDB	USDA
Rumex	FooDB	USDA
Rumex acetosa	FooDB	DTU Food
Rumex articus	FooDB	USDA
Saccharina japonica	FooDB	DTU Food
Sagittaria latifolia	FooDB	USDA
Salmo salar	FooDB	USDA
Salmo trutta forma trutta	FooDB	USDA
Salmonella enterica	LOTUS Database	35616633
Salmonidae	FooDB	DTU Food
Salvelinus	FooDB	DTU Food
Salvelinus namaycush	FooDB	DTU Food
Salvia hispanica	FooDB	USDA
Salvia rosmarinus	FooDB	USDA
Sambucus nigra L.	FooDB	DTU Food
Sander lucioperca	FooDB	DTU Food
Satureja hortensis L.	FooDB	USDA
Scomberomorus cavalla	FooDB	USDA
Scomberomorus maculatus	FooDB	USDA
Scombridae	FooDB	DTU Food
Scophthalmus maximus	FooDB	DTU Food
Scorzonera hispanica	FooDB	DTU Food
Sebastes	FooDB	USDA
Sebastes alutus	FooDB	DTU Food
Sebastes viviparus	FooDB	DTU Food
Secale cereale	FooDB	DTU Food
Sechium edule	FooDB	DTU Food
Sepiidae	FooDB	USDA
Seriola lalandi	FooDB	USDA
Sesamum indicum	FooDB	DTU Food
Sesbania bispinosa	FooDB	USDA
Siluriformes	FooDB	DTU Food
Solanum lycopersicum	FooDB	DTU Food
Solanum lycopersicum var. lycopersicum	FooDB	USDA
Solanum melongena	FooDB	DTU Food
Solanum quitoense	FooDB	USDA
Solanum tuberosum	FooDB	DTU Food
Soleidae	FooDB	USDA
Sorghum bicolor	FooDB	USDA
Spinacia oleracea	FooDB	DTU Food
Spirulina	FooDB	USDA
Squaliformes	FooDB	USDA
Squalus acanthias	FooDB	DTU Food
Stenodus leucichthys	FooDB	USDA
Stenotomus chrysops	FooDB	USDA
Strombidae	FooDB	USDA
Struthio camelus	FooDB	USDA
Sus scrofa	FooDB	USDA
Sus scrofa domestica	FooDB	DTU Food
Synechococcus elongatus	LOTUS Database	35616633
Syzygium aromaticum	FooDB	USDA
Syzygium cumini	KNApSAcK Database	22123792
Tamarindus indica	FooDB	DTU Food
Taraxacum officinale	FooDB	DTU Food
Tetragonia tetragonioides	FooDB	USDA
Teuthida	FooDB	USDA
Theobroma cacao	LOTUS Database	35616633
Thunnus	FooDB	DTU Food
Thunnus albacares	FooDB	USDA
Thunnus thynnus	FooDB	USDA
Thymus vulgaris	FooDB	USDA
Trachinotus carolinus	FooDB	USDA
Trachurus symmetricus	FooDB	USDA
Tragopogon porrifolius	FooDB	USDA
Trigonella foenum-graecum	KNApSAcK Database	22123792
Trisopterus esmarkii	FooDB	DTU Food
Triticum	FooDB	DTU Food
Triticum aestivum	FooDB	USDA
Triticum durum	FooDB	DTU Food
Triticum spelta	FooDB	USDA
Triticum turanicum	FooDB	USDA
Trypanosoma brucei	LOTUS Database	35616633
Typha angustifolia	FooDB	USDA
Undaria pinnatifida	FooDB	USDA
Vaccinium	FooDB	DTU Food
Vaccinium macrocarpon	FooDB	USDA
Vaccinium myrtillus	FooDB	DTU Food
Vaccinium ovalifolium	FooDB	USDA
Vaccinium oxycoccos	FooDB	USDA
Vaccinium reticulatum	FooDB	USDA
Vaccinium vitis-idaea	FooDB	DTU Food
Vanilla	FooDB	USDA
Viburnum edule	FooDB	USDA
Vicia faba	FooDB	USDA
Vigna aconitifolia	FooDB	USDA
Vigna angularis	FooDB	DTU Food
Vigna mungo	FooDB	USDA
Vigna radiata	FooDB	DTU Food
Vigna unguiculata	FooDB	USDA
Vigna unguiculata ssp. cylindrica	FooDB	USDA
Vigna unguiculata ssp. unguiculata	FooDB	USDA
Vigna unguiculata var. sesquipedalis	FooDB	USDA
Virola surinamensis	FooDB	USDA
Vitis	FooDB	DTU Food
Xanthosoma sagittifolium	FooDB	USDA
Xiphias gladius	FooDB	USDA
Zea mays L.	FooDB	DTU Food
Zingiber officinale	FooDB	DTU Food
Zizania	FooDB	USDA
Ziziphus jujuba	KNApSAcK Database	22123792
Ziziphus zizyphus	FooDB	USDA
Zoarces americanus	FooDB	USDA

Species Where Detected

Species Name	Source	Reference
Cordyceps sinensis	KNApSAcK Database	22123792

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 )

Physical Properties

State

Solid

Experimental 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

Predicted 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

External Links

HMDB ID

HMDB0000235

DrugBank ID

DB00152

Phenol Explorer Compound ID

Not Available

FoodDB 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

Good Scents ID

Not Available

References

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 ]

Showing NP-Card for Thiamine (NP0001167)

MOL for NP0001167 (Thiamine)

3D MOL for NP0001167 (Thiamine)

3D SDF for NP0001167 (Thiamine)

3D-SDF for NP0001167 (Thiamine)

PDB for NP0001167 (Thiamine)

3D PDB for NP0001167 (Thiamine)

SMILES for NP0001167 (Thiamine)

INCHI for NP0001167 (Thiamine)

Structure for NP0001167 (Thiamine)

3D Structure for NP0001167 (Thiamine)