MiMeDB: Showing metabocard for thiamine phosphate (MMDBc0054676)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2022-06-05 23:23:53 UTC

Update Date

2024-04-20 06:15:36 UTC

Metabolite ID

MMDBc0054676

Metabolite Identification

Common Name

thiamine phosphate

Description

Thiamine monophosphate, also known as thiamin phosphoric acid or TMP, belongs to the class of organic compounds known as thiamine phosphates. These are thiamine derivatives in which the hydroxyl group of the ethanol moiety is substituted by a phosphate group. Thiamine monophosphate is a very strong basic compound (based on its pKa). Thiamine monophosphate is one of the five known natural thiamine phosphate derivatives. Thiamine (vitamin B1) is the transport form of the vitamin while the phosphorylated derivatives are the active forms.

Structure

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

HMDB0002666
     RDKit          3D
Thiamine monophosphate
 40 41  0  0  0  0  0  0  0  0999 V2000
   -6.2786    2.5952    0.6320 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9423    1.9355    0.3819 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7763    2.5582    0.5813 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5985    1.9701    0.2952 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5400    0.7094   -0.2249 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3872    0.0412   -0.7352 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5243   -0.8445   -0.0486 N   0  0  0  0  0  4  0  0  0  0  0  0
   -1.0420   -1.7577    0.8018 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3145   -2.5097    1.4727 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.5644   -1.6047    0.6227 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9618   -1.7522    0.9496 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1044   -1.8325    0.0384 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0815   -0.5342   -0.6226 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5448    0.2157   -0.2109 P   0  0  0  0  0  5  0  0  0  0  0  0
    6.5470    0.3249   -1.2700 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1620    1.8308    0.3151 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2300   -0.5130    1.1735 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8246   -0.7825   -0.1210 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4828    0.0914   -1.1638 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7724    0.0674   -0.4273 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7581   -1.2801   -0.9665 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9237    0.6761   -0.1271 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4577    3.2312   -0.3134 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2970    3.2713    1.4728 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0452    1.8288    0.6459 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7002    2.5206    0.4926 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5461   -0.4083   -1.7792 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6666    0.9379   -1.0592 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0543   -2.0007    1.0831 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1569   -0.9332    1.7607 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0774   -2.6667    1.6595 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1000   -1.9422    0.4366 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0038   -2.6376   -0.7350 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1387    1.9005    0.3038 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7860   -0.0434    1.9508 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9142    0.9620   -0.7154 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1009   -0.5455   -1.8328 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7208    0.4592   -1.9450 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8782   -2.0665   -0.2891 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6277   -1.4723   -1.9789 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
 13 14  1  0
 14 15  2  0
 14 16  1  0
 14 17  1  0
 10 18  2  0
 18 19  1  0
  5 20  1  0
 20 21  1  0
 20 22  2  0
 22  2  1  0
 18  7  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  4 26  1  0
  6 27  1  0
  6 28  1  0
  8 29  1  0
 11 30  1  0
 11 31  1  0
 12 32  1  0
 12 33  1  0
 16 34  1  0
 17 35  1  0
 19 36  1  0
 19 37  1  0
 19 38  1  0
 21 39  1  0
 21 40  1  0
M  CHG  1   7   1
M  END


  Mrv1652305012018422D          

 22 23  0  0  0  0            999 V2000
    1.3791    0.3676    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0147    1.2814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3791   -1.2786    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3777    0.3676    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0921   -0.0455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2293   -1.2786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8043    0.3676    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5169   -0.0455    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1047   -0.7579    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2293    0.3676    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9272   -0.7579    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0028    0.4492    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6703   -0.0357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4154   -0.8203    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.4097   -0.8203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6646   -0.0357    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    2.8052    0.3686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0907   -0.0438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0907   -0.8690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8052   -1.2814    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5198   -0.8690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5198   -0.0438    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  4  5  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
  8 11  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 12 16  1  0  0  0  0
 15 16  2  0  0  0  0
  1 16  1  0  0  0  0
 12  2  1  0  0  0  0
 13  4  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 17 22  1  0  0  0  0
 21 22  2  0  0  0  0
  1 18  1  0  0  0  0
 19  3  1  0  0  0  0
 21  6  1  0  0  0  0
M  CHG  1  16   1
M  END
> <DATABASE_ID>
MMDBc0054676

> <DATABASE_NAME>
MIME

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

> <INCHI_IDENTIFIER>
InChI=1S/C12H17N4O4PS/c1-8-11(3-4-20-21(17,18)19)22-7-16(8)6-10-5-14-9(2)15-12(10)13/h5,7H,3-4,6H2,1-2H3,(H3-,13,14,15,17,18,19)/p+1

> <INCHI_KEY>
HZSAJDVWZRBGIF-UHFFFAOYSA-O

> <FORMULA>
C12H18N4O4PS

> <MOLECULAR_WEIGHT>
345.334

> <EXACT_MASS>
345.078637286

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
40

> <JCHEM_AVERAGE_POLARIZABILITY>
32.5906471213632

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
1

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
-1.63

> <JCHEM_LOGP>
-5.696316403219863

> <ALOGPS_LOGS>
-3.92

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
6.712600648963036

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.6589988406382288

> <JCHEM_PKA_STRONGEST_BASIC>
5.507552519532389

> <JCHEM_POLAR_SURFACE_AREA>
122.44

> <JCHEM_REFRACTIVITY>
84.27259999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.56e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
thiamin monophosphate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0002666
     RDKit          3D
Thiamine monophosphate
 40 41  0  0  0  0  0  0  0  0999 V2000
   -6.2786    2.5952    0.6320 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9423    1.9355    0.3819 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7763    2.5582    0.5813 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5985    1.9701    0.2952 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5400    0.7094   -0.2249 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3872    0.0412   -0.7352 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5243   -0.8445   -0.0486 N   0  0  0  0  0  4  0  0  0  0  0  0
   -1.0420   -1.7577    0.8018 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3145   -2.5097    1.4727 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.5644   -1.6047    0.6227 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9618   -1.7522    0.9496 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1044   -1.8325    0.0384 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0815   -0.5342   -0.6226 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5448    0.2157   -0.2109 P   0  0  0  0  0  5  0  0  0  0  0  0
    6.5470    0.3249   -1.2700 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1620    1.8308    0.3151 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2300   -0.5130    1.1735 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8246   -0.7825   -0.1210 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4828    0.0914   -1.1638 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7724    0.0674   -0.4273 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7581   -1.2801   -0.9665 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9237    0.6761   -0.1271 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4577    3.2312   -0.3134 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2970    3.2713    1.4728 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0452    1.8288    0.6459 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7002    2.5206    0.4926 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5461   -0.4083   -1.7792 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6666    0.9379   -1.0592 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0543   -2.0007    1.0831 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1569   -0.9332    1.7607 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0774   -2.6667    1.6595 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1000   -1.9422    0.4366 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0038   -2.6376   -0.7350 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1387    1.9005    0.3038 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7860   -0.0434    1.9508 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9142    0.9620   -0.7154 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1009   -0.5455   -1.8328 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7208    0.4592   -1.9450 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8782   -2.0665   -0.2891 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6277   -1.4723   -1.9789 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
 13 14  1  0
 14 15  2  0
 14 16  1  0
 14 17  1  0
 10 18  2  0
 18 19  1  0
  5 20  1  0
 20 21  1  0
 20 22  2  0
 22  2  1  0
 18  7  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  4 26  1  0
  6 27  1  0
  6 28  1  0
  8 29  1  0
 11 30  1  0
 11 31  1  0
 12 32  1  0
 12 33  1  0
 16 34  1  0
 17 35  1  0
 19 36  1  0
 19 37  1  0
 19 38  1  0
 21 39  1  0
 21 40  1  0
M  CHG  1   7   1
M  END

HEADER    PROTEIN                                 01-MAY-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   01-MAY-20         0                                  
HETATM    1  C   UNK     0       2.574   0.686   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.027   2.392   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0       2.574  -2.387   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0      -2.572   0.686   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -3.905  -0.085   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.895  -2.387   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -5.235   0.686   0.000  0.00  0.00           O+0
HETATM    8  P   UNK     0      -6.565  -0.085   0.000  0.00  0.00           P+0
HETATM    9  O   UNK     0      -5.795  -1.415   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0      -7.895   0.686   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0      -7.331  -1.415   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -0.005   0.838   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.251  -0.067   0.000  0.00  0.00           C+0
HETATM   14  S   UNK     0      -0.775  -1.531   0.000  0.00  0.00           S+0
HETATM   15  C   UNK     0       0.765  -1.531   0.000  0.00  0.00           C+0
HETATM   16  N   UNK     0       1.241  -0.067   0.000  0.00  0.00           N+1
HETATM   17  C   UNK     0       5.236   0.688   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.903  -0.082   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.903  -1.622   0.000  0.00  0.00           C+0
HETATM   20  N   UNK     0       5.236  -2.392   0.000  0.00  0.00           N+0
HETATM   21  C   UNK     0       6.570  -1.622   0.000  0.00  0.00           C+0
HETATM   22  N   UNK     0       6.570  -0.082   0.000  0.00  0.00           N+0
CONECT    1   16   18                                                       
CONECT    2   12                                                            
CONECT    3   19                                                            
CONECT    4    5   13                                                       
CONECT    5    4    7                                                       
CONECT    6   21                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9   10   11                                             
CONECT    9    8                                                            
CONECT   10    8                                                            
CONECT   11    8                                                            
CONECT   12   13   16    2                                                  
CONECT   13   12   14    4                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   12   15    1                                                  
CONECT   17   18   22                                                       
CONECT   18   17   19    1                                                  
CONECT   19   18   20    3                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22    6                                                  
CONECT   22   17   21                                                       
MASTER        0    0    0    0    0    0    0    0   22    0   46    0
END

COMPND    HMDB0002666
HETATM    1  C1  UNL     1      -6.279   2.595   0.632  1.00  0.00           C  
HETATM    2  C2  UNL     1      -4.942   1.936   0.382  1.00  0.00           C  
HETATM    3  N1  UNL     1      -3.776   2.558   0.581  1.00  0.00           N  
HETATM    4  C3  UNL     1      -2.598   1.970   0.295  1.00  0.00           C  
HETATM    5  C4  UNL     1      -2.540   0.709  -0.225  1.00  0.00           C  
HETATM    6  C5  UNL     1      -1.387   0.041  -0.735  1.00  0.00           C  
HETATM    7  N2  UNL     1      -0.524  -0.844  -0.049  1.00  0.00           N1+
HETATM    8  C6  UNL     1      -1.042  -1.758   0.802  1.00  0.00           C  
HETATM    9  S1  UNL     1       0.315  -2.510   1.473  1.00  0.00           S  
HETATM   10  C7  UNL     1       1.564  -1.605   0.623  1.00  0.00           C  
HETATM   11  C8  UNL     1       2.962  -1.752   0.950  1.00  0.00           C  
HETATM   12  C9  UNL     1       4.104  -1.832   0.038  1.00  0.00           C  
HETATM   13  O1  UNL     1       4.081  -0.534  -0.623  1.00  0.00           O  
HETATM   14  P1  UNL     1       5.545   0.216  -0.211  1.00  0.00           P  
HETATM   15  O2  UNL     1       6.547   0.325  -1.270  1.00  0.00           O  
HETATM   16  O3  UNL     1       5.162   1.831   0.315  1.00  0.00           O  
HETATM   17  O4  UNL     1       6.230  -0.513   1.173  1.00  0.00           O  
HETATM   18  C10 UNL     1       0.825  -0.782  -0.121  1.00  0.00           C  
HETATM   19  C11 UNL     1       1.483   0.091  -1.164  1.00  0.00           C  
HETATM   20  C12 UNL     1      -3.772   0.067  -0.427  1.00  0.00           C  
HETATM   21  N3  UNL     1      -3.758  -1.280  -0.966  1.00  0.00           N  
HETATM   22  N4  UNL     1      -4.924   0.676  -0.127  1.00  0.00           N  
HETATM   23  H1  UNL     1      -6.458   3.231  -0.313  1.00  0.00           H  
HETATM   24  H2  UNL     1      -6.297   3.271   1.473  1.00  0.00           H  
HETATM   25  H3  UNL     1      -7.045   1.829   0.646  1.00  0.00           H  
HETATM   26  H4  UNL     1      -1.700   2.521   0.493  1.00  0.00           H  
HETATM   27  H5  UNL     1      -1.546  -0.408  -1.779  1.00  0.00           H  
HETATM   28  H6  UNL     1      -0.667   0.938  -1.059  1.00  0.00           H  
HETATM   29  H7  UNL     1      -2.054  -2.001   1.083  1.00  0.00           H  
HETATM   30  H8  UNL     1       3.157  -0.933   1.761  1.00  0.00           H  
HETATM   31  H9  UNL     1       3.077  -2.667   1.660  1.00  0.00           H  
HETATM   32  H10 UNL     1       5.100  -1.942   0.437  1.00  0.00           H  
HETATM   33  H11 UNL     1       4.004  -2.638  -0.735  1.00  0.00           H  
HETATM   34  H12 UNL     1       4.139   1.901   0.304  1.00  0.00           H  
HETATM   35  H13 UNL     1       5.786  -0.043   1.951  1.00  0.00           H  
HETATM   36  H14 UNL     1       1.914   0.962  -0.715  1.00  0.00           H  
HETATM   37  H15 UNL     1       2.101  -0.546  -1.833  1.00  0.00           H  
HETATM   38  H16 UNL     1       0.721   0.459  -1.945  1.00  0.00           H  
HETATM   39  H17 UNL     1      -3.878  -2.066  -0.289  1.00  0.00           H  
HETATM   40  H18 UNL     1      -3.628  -1.472  -1.979  1.00  0.00           H  
CONECT    1    2   23   24   25
CONECT    2    3    3   22
CONECT    3    4
CONECT    4    5    5   26
CONECT    5    6   20
CONECT    6    7   27   28
CONECT    7    8    8   18
CONECT    8    9   29
CONECT    9   10
CONECT   10   11   18   18
CONECT   11   12   30   31
CONECT   12   13   32   33
CONECT   13   14
CONECT   14   15   15   16   17
CONECT   16   34
CONECT   17   35
CONECT   18   19
CONECT   19   36   37   38
CONECT   20   21   22   22
CONECT   21   39   40
END

HMDB0002666
     RDKit          3D
Thiamine monophosphate
 40 41  0  0  0  0  0  0  0  0999 V2000
   -6.2786    2.5952    0.6320 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9423    1.9355    0.3819 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7763    2.5582    0.5813 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5985    1.9701    0.2952 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5400    0.7094   -0.2249 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3872    0.0412   -0.7352 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5243   -0.8445   -0.0486 N   0  0  0  0  0  4  0  0  0  0  0  0
   -1.0420   -1.7577    0.8018 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3145   -2.5097    1.4727 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.5644   -1.6047    0.6227 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9618   -1.7522    0.9496 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1044   -1.8325    0.0384 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0815   -0.5342   -0.6226 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5448    0.2157   -0.2109 P   0  0  0  0  0  5  0  0  0  0  0  0
    6.5470    0.3249   -1.2700 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1620    1.8308    0.3151 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2300   -0.5130    1.1735 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8246   -0.7825   -0.1210 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4828    0.0914   -1.1638 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7724    0.0674   -0.4273 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7581   -1.2801   -0.9665 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9237    0.6761   -0.1271 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4577    3.2312   -0.3134 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2970    3.2713    1.4728 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0452    1.8288    0.6459 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7002    2.5206    0.4926 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5461   -0.4083   -1.7792 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6666    0.9379   -1.0592 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0543   -2.0007    1.0831 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1569   -0.9332    1.7607 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0774   -2.6667    1.6595 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1000   -1.9422    0.4366 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0038   -2.6376   -0.7350 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1387    1.9005    0.3038 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7860   -0.0434    1.9508 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9142    0.9620   -0.7154 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1009   -0.5455   -1.8328 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7208    0.4592   -1.9450 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8782   -2.0665   -0.2891 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6277   -1.4723   -1.9789 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
 13 14  1  0
 14 15  2  0
 14 16  1  0
 14 17  1  0
 10 18  2  0
 18 19  1  0
  5 20  1  0
 20 21  1  0
 20 22  2  0
 22  2  1  0
 18  7  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  4 26  1  0
  6 27  1  0
  6 28  1  0
  8 29  1  0
 11 30  1  0
 11 31  1  0
 12 32  1  0
 12 33  1  0
 16 34  1  0
 17 35  1  0
 19 36  1  0
 19 37  1  0
 19 38  1  0
 21 39  1  0
 21 40  1  0
M  CHG  1   7   1
M  END

Synonyms

Value	Source
2-[3-[(4-Amino-2-methyl-pyrimidin-5-yl)methyl]-4-methyl-thiazol-3-ium-5-yl]ethyl dihydrogen phosphate	ChEBI
2-[3-[(4-Amino-2-methylpyrimidin-5-yl)methyl]-4-methyl-1,3-thiazol-3-ium-5-yl]ethyl dihydrogen phosphate	ChEBI
2-[3-[(4-Azanyl-2-methyl-pyrimidin-5-yl)methyl]-4-methyl-1,3-thiazol-3-ium-5-yl]ethyl dihydrogen phosphate	ChEBI
3-[(4-Amino-2-methyl-5-pyrimidinyl)methyl]-4-methyl-5-[2-(phosphonooxy)ethyl]thiazolium	ChEBI
Thiamin monophosphate	ChEBI
Thiamin phosphate	ChEBI
Thiamine phosphate	ChEBI
TMP	ChEBI
Vitamin b1 monophosphate	ChEBI
Vitamin b1 phosphate	ChEBI
2-[3-[(4-Amino-2-methyl-pyrimidin-5-yl)methyl]-4-methyl-thiazol-3-ium-5-yl]ethyl dihydrogen phosphoric acid	Generator
2-[3-[(4-Amino-2-methylpyrimidin-5-yl)methyl]-4-methyl-1,3-thiazol-3-ium-5-yl]ethyl dihydrogen phosphoric acid	Generator
2-[3-[(4-Azanyl-2-methyl-pyrimidin-5-yl)methyl]-4-methyl-1,3-thiazol-3-ium-5-yl]ethyl dihydrogen phosphoric acid	Generator
Thiamin monophosphoric acid	Generator
Thiamin phosphoric acid	Generator
Thiamine phosphoric acid	Generator
Vitamin b1 monophosphoric acid	Generator
Vitamin b1 phosphoric acid	Generator
Thiamine monophosphoric acid	Generator
Thiamine phosphoester	HMDB
monoPhosphate, thiamine	HMDB
Phosphoester, thiamine	HMDB
ThP	HMDB
Thiamin-p	HMDB
Thiamine-pi	HMDB
Thiamine monophosphate	ChEBI

Molecular Formula

C₁₂H₁₈N₄O₄PS

Average Mass

345.334

Monoisotopic Mass

345.078637286

IUPAC Name

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

Traditional Name

thiamin monophosphate

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C12H17N4O4PS/c1-8-11(3-4-20-21(17,18)19)22-7-16(8)6-10-5-14-9(2)15-12(10)13/h5,7H,3-4,6H2,1-2H3,(H3-,13,14,15,17,18,19)/p+1

InChI Key

HZSAJDVWZRBGIF-UHFFFAOYSA-O

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as thiamine phosphates. These are thiamine derivatives in which the hydroxyl group of the ethanol moiety is substituted by a phosphate group.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Diazines

Sub Class

Pyrimidines and pyrimidine derivatives

Direct Parent

Thiamine phosphates

Alternative Parents

Substituents

Thiamine-phosphate
4,5-disubstituted 1,3-thiazole
Monoalkyl phosphate
Hydropyrimidine
Organic phosphoric acid derivative
Phosphoric acid ester
Alkyl phosphate
Imidolactam
Azole
Thiazole
Heteroaromatic compound
Azacycle
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Organonitrogen compound
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Organic cation
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

1,3-thiazolium cation (CHEBI:9533 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.046 g/L	ALOGPS
logP	-1.6	ALOGPS
logP	-5.7	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Acidic)	1.66	ChemAxon
pKa (Strongest Basic)	5.51	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	122.44 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	84.27 m³·mol⁻¹	ChemAxon
Polarizability	32.59 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

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Positive	splash10-00di-0900000000-113c390c4d19be64bd0d	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-00ec-9600000000-7ac71f27ba3ca0e2fe91	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-00di-0900000000-3cf7f44d89518227c630	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-00di-1900000000-135b9e1aef14efaa6b3e	2021-09-20	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0002-0109000000-eaecb343c9ff0c6f060f	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0002-9148000000-58b0f8616c541d910c2a	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-3900000000-cbb443e2c206edc550d7	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-4109000000-1d9d048d26c541eac8d6	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-002b-9001000000-3b5f50e234444b8876e6	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9000000000-8a23656944b47d54a23a	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-006t-0519000000-8f42bf528fe96c321951	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00di-0930000000-7ae879f5468ac7078781	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00di-0900000000-b2954ab23477c3f8bdbc	2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, D₂O, experimental)		2016-10-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, D₂O, experimental)		2016-10-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-25	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular
Membrane
Mitochondria

Biospecimen Locations

Cerebrospinal Fluid (CSF)

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species
MMDBp0196230	Cancer-related nucleoside-triphosphatase	Enzyme	Q9BSD7	Homo sapiens
MMDBp0196656	14 kDa phosphohistidine phosphatase	Enzyme	Q9NRX4	Homo sapiens

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference
Alzheimer's disease		Association	Human Cerebrospinal Fluid (CSF)	HMDB	12111441

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites
Bacteria	Proteobacteria	143	Human ; Human feces; Pig ; Cattle ; Turkey ; Chicken ; Human feces; pleural fluid plaque; bal; Human stool
Bacteria	Aquificae	3
Bacteria	Actinobacteria	31	Human ; Cattle ; Human feces
Archaea/Archaea	Euryarchaeota	26
Bacteria	Spirochaetes	3
Archaea/Archaea	Thaumarchaeota	1
Bacteria	Cyanobacteria	14
Archaea/Archaea	Crenarchaeota	2
Bacteria	Planctomycetes	1
Bacteria	Firmicutes	100	Human feces; Human ; Catfish ; Cattle
Eukaryota/Fungi	Ascomycota	2
Bacteria	Thermotogae	1
Bacteria	Bacteroidetes	7	Human ; Human feces
Bacteria	Chloroflexi	4
Bacteria	Chlamydiae	2	Human ; Sheep
Bacteria	Chlorobi	6
Bacteria	Deinococcus-thermus	4
Bacteria	Dictyoglomi	2
Bacteria	Fusobacteria	1	Human ; Human feces
Bacteria	Acidobacteria	1
Archaea	Euryarchaeota	1
Bacteria	nah	1

Exposure Sources

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Cerebrospinal fluid (csf)	Detected and Quantified	0.0035	0.0038			uM	Adult (>18 years old)	Both	Alzheimer's disease	HMDB	12111441
Human Cerebrospinal fluid (csf)	Detected and Quantified	0.0043	0.0024			uM	Adult (>18 years old)	Both	Normal	HMDB	12111441

External Links

HMDB ID

HMDB0002666

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Thiamine_monophosphate

METLIN ID

Not Available

PubChem Compound

1131

PDB ID

Not Available

ChEBI ID

9533

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Tallaksen CM, Bohmer T, Bell H: Concentrations of the water-soluble vitamins thiamin, ascorbic acid, and folic acid in serum and cerebrospinal fluid of healthy individuals. Am J Clin Nutr. 1992 Sep;56(3):559-64. doi: 10.1093/ajcn/56.3.559. [PubMed:1503069 ]
Tallaksen CM, Bohmer T, Bell H, Karlsen J: Concomitant determination of thiamin and its phosphate esters in human blood and serum by high-performance liquid chromatography. J Chromatogr. 1991 Mar 8;564(1):127-36. doi: 10.1016/0378-4347(91)80075-n. [PubMed:1860908 ]
Kimura M, Itokawa Y: Determination of thiamine and its phosphate esters in human and rat blood by high-performance liquid chromatography with post-column derivatization. J Chromatogr. 1985 Sep 20;332:181-8. doi: 10.1016/s0021-9673(01)83295-7. [PubMed:4055941 ]
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Showing metabocard for thiamine phosphate (MMDBc0054676)

MOL for #<Metabolite:0x00007fdb094ae4f8>

3D MOL for #<Metabolite:0x00007fdb094ae4f8>

3D SDF for #<Metabolite:0x00007fdb094ae4f8>

3D-SDF for #<Metabolite:0x00007fdb094ae4f8>

PDB for #<Metabolite:0x00007fdb094ae4f8>

3D PDB for #<Metabolite:0x00007fdb094ae4f8>

SMILES for #<Metabolite:0x00007fdb094ae4f8>

INCHI for #<Metabolite:0x00007fdb094ae4f8>

Structure for #<Metabolite:0x00007fdb094ae4f8>

3D Structure for #<Metabolite:0x00007fdb094ae4f8>