NP-MRD: Showing NP-Card for Thiamine monophosphate (NP0002859)

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Record Information

Version

1.0

Created at

2020-11-23 19:42:11 UTC

Updated at

2021-08-12 19:52:21 UTC

NP-MRD ID

NP0002859

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Thiamine monophosphate

Provided By

BMRB

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. In humans, thiamine monophosphate is involved in the metabolic disorder called the thiamine metabolism pathway. Thiamine monophosphate is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Thiamine monophosphate is found in Mus musculus and Synechococcus elongatus. It was first documented in 1991 (PMID: 1860908). Based on a literature review a significant number of articles have been published on Thiamine monophosphate (PMID: 17984079) (PMID: 16352439) (PMID: 8333605) (PMID: 1503069).

Structure

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

NP0002859
     RDKit          3D

 40 41  0  0  0  0  0  0  0  0999 V2000
   -4.1767   -2.3302   -2.2634 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5268   -1.5146   -1.1958 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3795   -1.9002   -0.6107 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7680   -1.1859    0.3574 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3169    0.0011    0.7928 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7645    0.8665    1.8341 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3167    0.5848    2.0509 N   0  0  0  0  0  4  0  0  0  0  0  0
    0.0120   -0.3584    2.9417 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7106   -0.3911    2.8943 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.9401    0.8388    1.7014 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2469    1.3366    1.1390 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5787    0.7552   -0.1914 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6557   -0.6523   -0.0466 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0414   -1.3161   -1.5705 P   0  0  0  0  0  5  0  0  0  0  0  0
    5.0152   -0.3691   -2.2652 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6368   -1.5168   -2.4799 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7250   -2.8215   -1.3019 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6529    1.1929    1.4221 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3645    2.2961    0.4100 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4934    0.3827    0.1833 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1268    1.5969    0.5754 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0761   -0.3596   -0.7833 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0119   -3.4216   -2.1164 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2909   -2.1912   -2.2492 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8338   -2.0518   -3.2793 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8462   -1.4975    0.8266 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9187    1.9242    1.5391 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3178    0.7364    2.7753 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6659   -0.9742    3.5645 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0263    1.1303    1.8996 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2167    2.4616    1.0603 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6243    1.0681   -0.4813 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8768    0.9773   -1.0009 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6714   -2.4006   -2.9152 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7074   -2.8004   -1.4096 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0797    2.3207   -0.3997 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6385    2.2147   -0.0038 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4201    3.2359    1.0319 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4011    1.7973    1.5585 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3324    2.3350   -0.1525 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>
NP0002859

> <DATABASE_NAME>
NP-MRD

> <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

$$$$

NP0002859
     RDKit          3D

 40 41  0  0  0  0  0  0  0  0999 V2000
   -4.1767   -2.3302   -2.2634 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5268   -1.5146   -1.1958 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3795   -1.9002   -0.6107 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7680   -1.1859    0.3574 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3169    0.0011    0.7928 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7645    0.8665    1.8341 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3167    0.5848    2.0509 N   0  0  0  0  0  4  0  0  0  0  0  0
    0.0120   -0.3584    2.9417 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7106   -0.3911    2.8943 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.9401    0.8388    1.7014 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2469    1.3366    1.1390 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5787    0.7552   -0.1914 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6557   -0.6523   -0.0466 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0414   -1.3161   -1.5705 P   0  0  0  0  0  5  0  0  0  0  0  0
    5.0152   -0.3691   -2.2652 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6368   -1.5168   -2.4799 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7250   -2.8215   -1.3019 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6529    1.1929    1.4221 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3645    2.2961    0.4100 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4934    0.3827    0.1833 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1268    1.5969    0.5754 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0761   -0.3596   -0.7833 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0119   -3.4216   -2.1164 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2909   -2.1912   -2.2492 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8338   -2.0518   -3.2793 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8462   -1.4975    0.8266 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9187    1.9242    1.5391 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3178    0.7364    2.7753 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6659   -0.9742    3.5645 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0263    1.1303    1.8996 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2167    2.4616    1.0603 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6243    1.0681   -0.4813 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8768    0.9773   -1.0009 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6714   -2.4006   -2.9152 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7074   -2.8004   -1.4096 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0797    2.3207   -0.3997 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6385    2.2147   -0.0038 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4201    3.2359    1.0319 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4011    1.7973    1.5585 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3324    2.3350   -0.1525 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    NP0002859
HETATM    1  C1  UNL     1      -4.177  -2.330  -2.263  1.00  0.00           C  
HETATM    2  C2  UNL     1      -3.527  -1.515  -1.196  1.00  0.00           C  
HETATM    3  N1  UNL     1      -2.379  -1.900  -0.611  1.00  0.00           N  
HETATM    4  C3  UNL     1      -1.768  -1.186   0.357  1.00  0.00           C  
HETATM    5  C4  UNL     1      -2.317   0.001   0.793  1.00  0.00           C  
HETATM    6  C5  UNL     1      -1.765   0.866   1.834  1.00  0.00           C  
HETATM    7  N2  UNL     1      -0.317   0.585   2.051  1.00  0.00           N1+
HETATM    8  C6  UNL     1       0.012  -0.358   2.942  1.00  0.00           C  
HETATM    9  S1  UNL     1       1.711  -0.391   2.894  1.00  0.00           S  
HETATM   10  C7  UNL     1       1.940   0.839   1.701  1.00  0.00           C  
HETATM   11  C8  UNL     1       3.247   1.337   1.139  1.00  0.00           C  
HETATM   12  C9  UNL     1       3.579   0.755  -0.191  1.00  0.00           C  
HETATM   13  O1  UNL     1       3.656  -0.652  -0.047  1.00  0.00           O  
HETATM   14  P1  UNL     1       4.041  -1.316  -1.570  1.00  0.00           P  
HETATM   15  O2  UNL     1       5.015  -0.369  -2.265  1.00  0.00           O  
HETATM   16  O3  UNL     1       2.637  -1.517  -2.480  1.00  0.00           O  
HETATM   17  O4  UNL     1       4.725  -2.821  -1.302  1.00  0.00           O  
HETATM   18  C10 UNL     1       0.653   1.193   1.422  1.00  0.00           C  
HETATM   19  C11 UNL     1       0.364   2.296   0.410  1.00  0.00           C  
HETATM   20  C12 UNL     1      -3.493   0.383   0.183  1.00  0.00           C  
HETATM   21  N3  UNL     1      -4.127   1.597   0.575  1.00  0.00           N  
HETATM   22  N4  UNL     1      -4.076  -0.360  -0.783  1.00  0.00           N  
HETATM   23  H1  UNL     1      -4.012  -3.422  -2.116  1.00  0.00           H  
HETATM   24  H2  UNL     1      -5.291  -2.191  -2.249  1.00  0.00           H  
HETATM   25  H3  UNL     1      -3.834  -2.052  -3.279  1.00  0.00           H  
HETATM   26  H4  UNL     1      -0.846  -1.497   0.827  1.00  0.00           H  
HETATM   27  H5  UNL     1      -1.919   1.924   1.539  1.00  0.00           H  
HETATM   28  H6  UNL     1      -2.318   0.736   2.775  1.00  0.00           H  
HETATM   29  H7  UNL     1      -0.666  -0.974   3.565  1.00  0.00           H  
HETATM   30  H8  UNL     1       4.026   1.130   1.900  1.00  0.00           H  
HETATM   31  H9  UNL     1       3.217   2.462   1.060  1.00  0.00           H  
HETATM   32  H10 UNL     1       4.624   1.068  -0.481  1.00  0.00           H  
HETATM   33  H11 UNL     1       2.877   0.977  -1.001  1.00  0.00           H  
HETATM   34  H12 UNL     1       2.671  -2.401  -2.915  1.00  0.00           H  
HETATM   35  H13 UNL     1       5.707  -2.800  -1.410  1.00  0.00           H  
HETATM   36  H14 UNL     1       1.080   2.321  -0.400  1.00  0.00           H  
HETATM   37  H15 UNL     1      -0.638   2.215  -0.004  1.00  0.00           H  
HETATM   38  H16 UNL     1       0.420   3.236   1.032  1.00  0.00           H  
HETATM   39  H17 UNL     1      -4.401   1.797   1.558  1.00  0.00           H  
HETATM   40  H18 UNL     1      -4.332   2.335  -0.153  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

NP0002859
     RDKit          3D

40 41  0  0  0  0  0  0  0  0999 V2000
   -4.1767   -2.3302   -2.2634 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5268   -1.5146   -1.1958 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3795   -1.9002   -0.6107 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7680   -1.1859    0.3574 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3169    0.0011    0.7928 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7645    0.8665    1.8341 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3167    0.5848    2.0509 N   0  0  0  0  0  4  0  0  0  0  0  0
    0.0120   -0.3584    2.9417 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7106   -0.3911    2.8943 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.9401    0.8388    1.7014 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2469    1.3366    1.1390 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5787    0.7552   -0.1914 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6557   -0.6523   -0.0466 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0414   -1.3161   -1.5705 P   0  0  0  0  0  5  0  0  0  0  0  0
    5.0152   -0.3691   -2.2652 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6368   -1.5168   -2.4799 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7250   -2.8215   -1.3019 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6529    1.1929    1.4221 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3645    2.2961    0.4100 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4934    0.3827    0.1833 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1268    1.5969    0.5754 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0761   -0.3596   -0.7833 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0119   -3.4216   -2.1164 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2909   -2.1912   -2.2492 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8338   -2.0518   -3.2793 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8462   -1.4975    0.8266 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9187    1.9242    1.5391 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3178    0.7364    2.7753 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6659   -0.9742    3.5645 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0263    1.1303    1.8996 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2167    2.4616    1.0603 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6243    1.0681   -0.4813 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8768    0.9773   -1.0009 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6714   -2.4006   -2.9152 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7074   -2.8004   -1.4096 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0797    2.3207   -0.3997 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6385    2.2147   -0.0038 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4201    3.2359    1.0319 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4011    1.7973    1.5585 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3324    2.3350   -0.1525 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

View in JSmol View NMR Assignments

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

Chemical Formula

C₁₂H₁₈N₄O₄PS

Average Mass

345.3340 Da

Monoisotopic Mass

345.07864 Da

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

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Anas platyrhynchos	FooDB	FooDB
Anatidae	FooDB	FooDB
Anser anser	FooDB	FooDB
Bison bison	FooDB	FooDB
Bos taurus	FooDB	FooDB
Bos taurus X Bison bison	FooDB	FooDB
Bubalus bubalis	FooDB	FooDB
Capra aegagrus hircus	FooDB	FooDB
Cervidae	FooDB	FooDB
Cervus canadensis	FooDB	FooDB
Columba	FooDB	FooDB
Columbidae	FooDB	FooDB
Dromaius novaehollandiae	FooDB	FooDB
Equus caballus	FooDB	FooDB
Gallus gallus	FooDB	FooDB
Lagopus muta	FooDB	FooDB
Leporidae	FooDB	FooDB
Lepus timidus	FooDB	FooDB
Melanitta fusca	FooDB	FooDB
Meleagris gallopavo	FooDB	FooDB
Mus musculus	LOTUS Database	35616633
Numida meleagris	FooDB	FooDB
Odocoileus	FooDB	FooDB
Oryctolagus	FooDB	FooDB
Ovis aries	FooDB	FooDB
Phasianidae	FooDB	FooDB
Phasianus colchicus	FooDB	FooDB
Struthio camelus	FooDB	FooDB
Sus scrofa	FooDB	FooDB
Sus scrofa domestica	FooDB	FooDB
Synechococcus elongatus	LOTUS Database	35616633

Species Where Detected

Species Name	Source	Reference
Escherichia coli	KNApSAcK Database	22123792

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

Not Available

Substituents

Not Available

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
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

External Links

HMDB ID

HMDB0002666

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB 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

Good Scents ID

Not Available

References

General References

Ulrich EL, Akutsu H, Doreleijers JF, Harano Y, Ioannidis YE, Lin J, Livny M, Mading S, Maziuk D, Miller Z, Nakatani E, Schulte CF, Tolmie DE, Kent Wenger R, Yao H, Markley JL: BioMagResBank. Nucleic Acids Res. 2008 Jan;36(Database issue):D402-8. doi: 10.1093/nar/gkm957. Epub 2007 Nov 4. [PubMed:17984079 ]
Lu W, Kimball E, Rabinowitz JD: A high-performance liquid chromatography-tandem mass spectrometry method for quantitation of nitrogen-containing intracellular metabolites. J Am Soc Mass Spectrom. 2006 Jan;17(1):37-50. doi: 10.1016/j.jasms.2005.09.001. Epub 2005 Dec 15. [PubMed:16352439 ]
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 ]
Tallaksen CM, Bell H, Bohmer T: Thiamin and thiamin phosphate ester deficiency assessed by high performance liquid chromatography in four clinical cases of Wernicke encephalopathy. Alcohol Clin Exp Res. 1993 Jun;17(3):712-6. doi: 10.1111/j.1530-0277.1993.tb00825.x. [PubMed:8333605 ]
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 ]

Showing NP-Card for Thiamine monophosphate (NP0002859)

MOL for NP0002859 (Thiamine monophosphate)

3D MOL for NP0002859 (Thiamine monophosphate)

3D SDF for NP0002859 (Thiamine monophosphate)

3D-SDF for NP0002859 (Thiamine monophosphate)

PDB for NP0002859 (Thiamine monophosphate)

3D PDB for NP0002859 (Thiamine monophosphate)

SMILES for NP0002859 (Thiamine monophosphate)

INCHI for NP0002859 (Thiamine monophosphate)

Structure for NP0002859 (Thiamine monophosphate)

3D Structure for NP0002859 (Thiamine monophosphate)