Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (4) Show 4 proteins XML

enzymes (4) Show 4 proteins

Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2020-07-09 20:38:04 UTC

HMDB ID

HMDB0001555

Secondary Accession Numbers

HMDB01555

Metabolite Identification

Common Name

Pyridoxamine 5'-phosphate

Description

Pyridoxamine 5'-phosphate belongs to the class of organic compounds known as pyridoxamine 5'-phosphates. These are heterocyclic aromatic compounds containing a pyridoxamine that carries a phosphate group at the 5'-position. Vitamin B6 is a water-soluble compound that was discovered in 1930s during nutrition studies on rats. The vitamin was named pyridoxine to indicate its structural homology to pyridine. Later it was shown that vitamin B6 could exist in two other, slightly different, chemical forms, termed pyridoxal and pyridoxamine. All three forms of vitamin B6 are precursors of an activated compound known as pyridoxal 5-phosphate (PLP), which plays a vital role as the cofactor of a large number of essential enzymes in the human body. Vitamin B6 is a water-soluble vitamin. The three major forms of vitamin B6 are pyridoxine (also known as pyridoxol), pyridoxal, and pyridoxamine, which are all converted in the liver to pyridoxal 5-phosphate (PLP) a cofactor in many reactions of amino acid metabolism. PLP also is necessary for the enzymatic reaction governing the release of glucose from glycogen.

Structure

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

HMDB0001555
     RDKit          3D
Pyridoxamine 5'-phosphate
 29 29  0  0  0  0  0  0  0  0999 V2000
   -3.7171   -1.6528    0.2919 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4014   -0.9865   -0.0087 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5604   -1.6473   -0.8186 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3566   -1.1901   -1.0993 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0340    0.0309   -0.5054 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4254    0.4555   -0.6029 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9507   -0.7480    0.0566 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5904   -0.7607    0.0502 P   0  0  0  0  0  5  0  0  0  0  0  0
    4.3101    0.5248    0.2457 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1344   -1.9260    1.1799 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9798   -1.3218   -1.5495 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8511    0.7545    0.2984 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3825    2.0592    0.7700 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2013    3.0226   -0.1022 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0708    0.2264    0.5748 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9610    0.8612    1.4227 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2159   -1.1033    1.0885 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4450   -2.6851    0.7116 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2767   -1.8760   -0.6190 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3205   -1.5986   -1.7958 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7289    1.3637   -0.2230 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7390    0.2317   -1.6776 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1747   -2.8158    0.8340 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8445   -1.6867   -1.5881 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9123    2.3391    1.7505 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6187    2.3354    0.8274 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3098    2.4511   -1.0245 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4060    3.6810   -0.4753 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7153    1.6618    1.9875 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  1  0
  8  9  2  0
  8 10  1  0
  8 11  1  0
  5 12  1  0
 12 13  1  0
 13 14  1  0
 12 15  2  0
 15 16  1  0
 15  2  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  4 20  1  0
  6 21  1  0
  6 22  1  0
 10 23  1  0
 11 24  1  0
 13 25  1  0
 13 26  1  0
 14 27  1  0
 14 28  1  0
 16 29  1  0
M  END


  Mrv1652307092020582D          

 16 16  0  0  0  0            999 V2000
 9999.625210000.8709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.910710000.4584    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.196310000.8709    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
 9998.607710001.5845    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9997.477710000.4563    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9997.782710001.5845    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9999.6252 9999.2204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.9066 9999.6360    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
10001.0570 9998.3954    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10002.4822 9999.2204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.054910000.8710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.340510000.4585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.3405 9999.6334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.0549 9999.2209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.7694 9999.6334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.769410000.4585    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  3  6  1  0  0  0  0
  7  8  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 11  1  0  0  0  0
  1 12  1  0  0  0  0
 13  7  1  0  0  0  0
 14  9  1  0  0  0  0
 15 10  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0001555

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1=NC=C(COP(O)(O)=O)C(CN)=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C8H13N2O5P/c1-5-8(11)7(2-9)6(3-10-5)4-15-16(12,13)14/h3,11H,2,4,9H2,1H3,(H2,12,13,14)

> <INCHI_KEY>
ZMJGSOSNSPKHNH-UHFFFAOYSA-N

> <FORMULA>
C8H13N2O5P

> <MOLECULAR_WEIGHT>
248.173

> <EXACT_MASS>
248.056208048

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
29

> <JCHEM_AVERAGE_POLARIZABILITY>
22.149163667314372

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
{[4-(aminomethyl)-5-hydroxy-6-methylpyridin-3-yl]methoxy}phosphonic acid

> <ALOGPS_LOGP>
-0.99

> <JCHEM_LOGP>
-2.2240254392379724

> <ALOGPS_LOGS>
-1.57

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
6.741483417681486

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.7417589844386874

> <JCHEM_PKA_STRONGEST_BASIC>
9.905510964077699

> <JCHEM_POLAR_SURFACE_AREA>
125.9

> <JCHEM_REFRACTIVITY>
56.63570000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.61e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
pyridoxamine-5'-phosphate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0001555
     RDKit          3D
Pyridoxamine 5'-phosphate
 29 29  0  0  0  0  0  0  0  0999 V2000
   -3.7171   -1.6528    0.2919 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4014   -0.9865   -0.0087 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5604   -1.6473   -0.8186 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3566   -1.1901   -1.0993 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0340    0.0309   -0.5054 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4254    0.4555   -0.6029 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9507   -0.7480    0.0566 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5904   -0.7607    0.0502 P   0  0  0  0  0  5  0  0  0  0  0  0
    4.3101    0.5248    0.2457 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1344   -1.9260    1.1799 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9798   -1.3218   -1.5495 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8511    0.7545    0.2984 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3825    2.0592    0.7700 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2013    3.0226   -0.1022 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0708    0.2264    0.5748 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9610    0.8612    1.4227 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2159   -1.1033    1.0885 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4450   -2.6851    0.7116 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2767   -1.8760   -0.6190 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3205   -1.5986   -1.7958 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7289    1.3637   -0.2230 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7390    0.2317   -1.6776 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1747   -2.8158    0.8340 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8445   -1.6867   -1.5881 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9123    2.3391    1.7505 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6187    2.3354    0.8274 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3098    2.4511   -1.0245 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4060    3.6810   -0.4753 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7153    1.6618    1.9875 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  1  0
  8  9  2  0
  8 10  1  0
  8 11  1  0
  5 12  1  0
 12 13  1  0
 13 14  1  0
 12 15  2  0
 15 16  1  0
 15  2  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  4 20  1  0
  6 21  1  0
  6 22  1  0
 10 23  1  0
 11 24  1  0
 13 25  1  0
 13 26  1  0
 14 27  1  0
 14 28  1  0
 16 29  1  0
M  END

HEADER    PROTEIN                                 09-JUL-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-JUL-20         0                                  
HETATM    1  C   UNK     0    8665.9678668.292   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0    8664.6338667.522   0.000  0.00  0.00           O+0
HETATM    3  P   UNK     0    8663.3008668.292   0.000  0.00  0.00           P+0
HETATM    4  O   UNK     0    8664.0688669.624   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0    8661.9588667.518   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0    8662.5288669.624   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0    8665.9678665.211   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0    8664.6268665.987   0.000  0.00  0.00           N+0
HETATM    9  O   UNK     0    8668.6408663.671   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0    8671.3008665.211   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8668.6368668.293   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8667.3028667.523   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8667.3028665.982   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8668.6368665.212   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8669.9708665.982   0.000  0.00  0.00           C+0
HETATM   16  N   UNK     0    8669.9708667.523   0.000  0.00  0.00           N+0
CONECT    1    2   12                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4    5    6                                             
CONECT    4    3                                                            
CONECT    5    3                                                            
CONECT    6    3                                                            
CONECT    7    8   13                                                       
CONECT    8    7                                                            
CONECT    9   14                                                            
CONECT   10   15                                                            
CONECT   11   12   16                                                       
CONECT   12   11   13    1                                                  
CONECT   13   12   14    7                                                  
CONECT   14   13   15    9                                                  
CONECT   15   14   16   10                                                  
CONECT   16   15   11                                                       
MASTER        0    0    0    0    0    0    0    0   16    0   32    0
END

COMPND    HMDB0001555
HETATM    1  C1  UNL     1      -3.717  -1.653   0.292  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.401  -0.987  -0.009  1.00  0.00           C  
HETATM    3  N1  UNL     1      -1.560  -1.647  -0.819  1.00  0.00           N  
HETATM    4  C3  UNL     1      -0.357  -1.190  -1.099  1.00  0.00           C  
HETATM    5  C4  UNL     1      -0.034   0.031  -0.505  1.00  0.00           C  
HETATM    6  C5  UNL     1       1.425   0.455  -0.603  1.00  0.00           C  
HETATM    7  O1  UNL     1       1.951  -0.748   0.057  1.00  0.00           O  
HETATM    8  P1  UNL     1       3.590  -0.761   0.050  1.00  0.00           P  
HETATM    9  O2  UNL     1       4.310   0.525   0.246  1.00  0.00           O  
HETATM   10  O3  UNL     1       4.134  -1.926   1.180  1.00  0.00           O  
HETATM   11  O4  UNL     1       3.980  -1.322  -1.550  1.00  0.00           O  
HETATM   12  C6  UNL     1      -0.851   0.754   0.298  1.00  0.00           C  
HETATM   13  C7  UNL     1      -0.382   2.059   0.770  1.00  0.00           C  
HETATM   14  N2  UNL     1      -1.201   3.023  -0.102  1.00  0.00           N  
HETATM   15  C8  UNL     1      -2.071   0.226   0.575  1.00  0.00           C  
HETATM   16  O5  UNL     1      -2.961   0.861   1.423  1.00  0.00           O  
HETATM   17  H1  UNL     1      -4.216  -1.103   1.088  1.00  0.00           H  
HETATM   18  H2  UNL     1      -3.445  -2.685   0.712  1.00  0.00           H  
HETATM   19  H3  UNL     1      -4.277  -1.876  -0.619  1.00  0.00           H  
HETATM   20  H4  UNL     1       0.320  -1.599  -1.796  1.00  0.00           H  
HETATM   21  H5  UNL     1       1.729   1.364  -0.223  1.00  0.00           H  
HETATM   22  H6  UNL     1       1.739   0.232  -1.678  1.00  0.00           H  
HETATM   23  H7  UNL     1       4.175  -2.816   0.834  1.00  0.00           H  
HETATM   24  H8  UNL     1       4.844  -1.687  -1.588  1.00  0.00           H  
HETATM   25  H9  UNL     1      -0.912   2.339   1.750  1.00  0.00           H  
HETATM   26  H10 UNL     1       0.619   2.335   0.827  1.00  0.00           H  
HETATM   27  H11 UNL     1      -1.310   2.451  -1.024  1.00  0.00           H  
HETATM   28  H12 UNL     1      -0.406   3.681  -0.475  1.00  0.00           H  
HETATM   29  H13 UNL     1      -2.715   1.662   1.987  1.00  0.00           H  
CONECT    1    2   17   18   19
CONECT    2    3    3   15
CONECT    3    4
CONECT    4    5    5   20
CONECT    5    6   12
CONECT    6    7   21   22
CONECT    7    8
CONECT    8    9    9   10   11
CONECT   10   23
CONECT   11   24
CONECT   12   13   15   15
CONECT   13   14   25   26
CONECT   14   27   28
CONECT   15   16
CONECT   16   29
END

HMDB0001555
     RDKit          3D
Pyridoxamine 5'-phosphate
 29 29  0  0  0  0  0  0  0  0999 V2000
   -3.7171   -1.6528    0.2919 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4014   -0.9865   -0.0087 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5604   -1.6473   -0.8186 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3566   -1.1901   -1.0993 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0340    0.0309   -0.5054 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4254    0.4555   -0.6029 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9507   -0.7480    0.0566 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5904   -0.7607    0.0502 P   0  0  0  0  0  5  0  0  0  0  0  0
    4.3101    0.5248    0.2457 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1344   -1.9260    1.1799 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9798   -1.3218   -1.5495 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8511    0.7545    0.2984 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3825    2.0592    0.7700 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2013    3.0226   -0.1022 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0708    0.2264    0.5748 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9610    0.8612    1.4227 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2159   -1.1033    1.0885 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4450   -2.6851    0.7116 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2767   -1.8760   -0.6190 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3205   -1.5986   -1.7958 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7289    1.3637   -0.2230 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7390    0.2317   -1.6776 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1747   -2.8158    0.8340 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8445   -1.6867   -1.5881 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9123    2.3391    1.7505 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6187    2.3354    0.8274 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3098    2.4511   -1.0245 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4060    3.6810   -0.4753 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7153    1.6618    1.9875 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  1  0
  8  9  2  0
  8 10  1  0
  8 11  1  0
  5 12  1  0
 12 13  1  0
 13 14  1  0
 12 15  2  0
 15 16  1  0
 15  2  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  4 20  1  0
  6 21  1  0
  6 22  1  0
 10 23  1  0
 11 24  1  0
 13 25  1  0
 13 26  1  0
 14 27  1  0
 14 28  1  0
 16 29  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
4'-Deoxy-4'-aminopyridoxal-5'-phosphate	ChEBI
Pyridoxamine 5'-(dihydrogen phosphate)	ChEBI
Pyridoxamine 5'-phosphoric acid	ChEBI
Pyridoxamine 5-phosphate	ChEBI
Pyridoxamine 5-phosphoric acid	ChEBI
Pyridoxamine phosphate	ChEBI
4'-Deoxy-4'-aminopyridoxal-5'-phosphoric acid	Generator
Pyridoxamine 5'-(dihydrogen phosphoric acid)	Generator
Pyridoxamine phosphoric acid	Generator
Pyridoxamine-P	MeSH, HMDB
PMP	HMDB
Pyridoxamine 5'-phosphate	HMDB
Pyridoxamine 5’-phosphate	HMDB
4’-Deoxy-4’-aminopyridoxal-5’-phosphate	HMDB
4’-Deoxy-4’-aminopyridoxal-5’-phosphoric acid	HMDB

Chemical Formula

C₈H₁₃N₂O₅P

Average Molecular Weight

248.173

Monoisotopic Molecular Weight

248.056208048

IUPAC Name

{[4-(aminomethyl)-5-hydroxy-6-methylpyridin-3-yl]methoxy}phosphonic acid

Traditional Name

pyridoxamine-5'-phosphate

CAS Registry Number

529-96-4

SMILES

CC1=NC=C(COP(O)(O)=O)C(CN)=C1O

InChI Identifier

InChI=1S/C8H13N2O5P/c1-5-8(11)7(2-9)6(3-10-5)4-15-16(12,13)14/h3,11H,2,4,9H2,1H3,(H2,12,13,14)

InChI Key

ZMJGSOSNSPKHNH-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pyridoxamine 5'-phosphates. These are heterocyclic aromatic compounds containing a pyridoxamine that carries a phosphate group at the 5'-position.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pyridines and derivatives

Sub Class

Pyridoxamines

Direct Parent

Pyridoxamine 5'-phosphates

Alternative Parents

Substituents

Pyridoxamine 5'-phosphate
Monoalkyl phosphate
Aralkylamine
Hydroxypyridine
Methylpyridine
Organic phosphoric acid derivative
Alkyl phosphate
Phosphoric acid ester
Heteroaromatic compound
Azacycle
Primary aliphatic amine
Hydrocarbon derivative
Amine
Primary amine
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Organic oxide
Organopnictogen compound
Organic oxygen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

monohydroxypyridine (CHEBI:18335 )
methylpyridines (CHEBI:18335 )
aminoalkylpyridine (CHEBI:18335 )
vitamin B6 phosphate (CHEBI:18335 )

Ontology

Not Available

Non-excretory biofluid

Blood (PMID: 1783639)

Cellular substructure

Organelle

Mitochondria

Mitochondria (HMDB: HMDB0001555)

Mitochondria (HMDB: HMDB0001555)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0001555)

Source

Endogenous

Endogenous (HMDB: HMDB0001555)

Plant

Animal

Animal (HMDB: HMDB0001555)

Exogenous

Food

Food (HMDB: HMDB0001555)

Animal origin

Poultry

Pheasant (FooDB: FOOD00430)
Anatidae (FooDB: FOOD00576)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Greylag goose (FooDB: FOOD00368)
Emu (FooDB: FOOD00360)
Mallard duck (FooDB: FOOD00353)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)
Guinea hen (FooDB: FOOD00373)

Lagomorph

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Herb and spice mixture

Curry powder (FooDB: FOOD00678)

Herbs and Spices (FooDB: FOOD00866)

Vegetable

Onion-family vegetable

Allium (FooDB: FOOD00005)
Garden onion (FooDB: FOOD00006)
Leek (FooDB: FOOD00007)
Garden onion (var.) (FooDB: FOOD00226)
Shallot (FooDB: FOOD00243)
Wild leek (FooDB: FOOD00396)
Red onion (FooDB: FOOD00962)
Green onion (FooDB: FOOD00963)
Onion-family vegetables (FooDB: FOOD00855)

Common beet (FooDB: FOOD00025)
Endive (FooDB: FOOD00048)
Rocket salad (ssp.) (FooDB: FOOD00077)
Swamp cabbage (FooDB: FOOD00091)
Lettuce (FooDB: FOOD00095)
Garden cress (FooDB: FOOD00099)
Spinach (FooDB: FOOD00178)
Swiss chard (FooDB: FOOD00237)
Chicory leaves (FooDB: FOOD00250)
Garland chrysanthemum (FooDB: FOOD00333)
Corn salad (FooDB: FOOD00340)
Jute (FooDB: FOOD00389)
Lambsquarters (FooDB: FOOD00394)
Malabar spinach (FooDB: FOOD00404)
New Zealand spinach (FooDB: FOOD00415)
Yautia (FooDB: FOOD00510)
Ostrich fern (FooDB: FOOD00556)
Romaine lettuce (FooDB: FOOD00888)
Yau choy (FooDB: FOOD00976)
Iceberg lettuce (FooDB: FOOD00973)
Pea shoots (FooDB: FOOD00975)
Water spinach (FooDB: FOOD00977)
Rocket salad (FooDB: FOOD00244)
Green vegetables (FooDB: FOOD00872)

Fruit vegetable

Pepper (FooDB: FOOD00040)
Olive (FooDB: FOOD00121)
Avocado (FooDB: FOOD00130)
Cherry tomato (FooDB: FOOD00172)
Garden tomato (FooDB: FOOD00171)
Eggplant (FooDB: FOOD00174)
Garden tomato (var.) (FooDB: FOOD00173)
Pepper (C. baccatum) (FooDB: FOOD00231)
Pepper (C. chinense) (FooDB: FOOD00232)
Pepper (Capsicum) (FooDB: FOOD00233)
Groundcherry (FooDB: FOOD00371)
Pepper (C. frutescens) (FooDB: FOOD00428)
Mexican groundcherry (FooDB: FOOD00491)
Pepper (C. pubescens) (FooDB: FOOD00849)
Green bell pepper (FooDB: FOOD00877)
Yellow bell pepper (FooDB: FOOD00878)
Italian sweet red pepper (FooDB: FOOD00881)
Orange bell pepper (FooDB: FOOD00879)
Red bell pepper (FooDB: FOOD00880)
Jalapeno pepper (FooDB: FOOD00955)
Cubanelle pepper (FooDB: FOOD00971)

Tuber

Stalk vegetable

Other vegetable

Giant butterbur (FooDB: FOOD00314)
Carob (FooDB: FOOD00321)
Chinese water chestnut (FooDB: FOOD00332)
Horseradish tree (FooDB: FOOD00379)
Sacred lotus (FooDB: FOOD00402)
Nopal (FooDB: FOOD00416)
Okra (FooDB: FOOD00420)
Sesbania flower (FooDB: FOOD00469)
Agave (FooDB: FOOD00563)
Narrowleaf cattail (FooDB: FOOD00564)
Heart of palm (FooDB: FOOD00718)
Tree fern (FooDB: FOOD00797)

Mushroom

Castanospermum australe (FooDB: FOOD00893)
Gentiana lutea (FooDB: FOOD00894)
Juniperus communis (FooDB: FOOD00895)
Albizia gummifera (FooDB: FOOD00896)

Brassica

Brassicas (FooDB: FOOD00857)

Fruit

Tropical fruit

Citrus

Lime (FooDB: FOOD00053)
Lemon (FooDB: FOOD00054)
Sweet orange (FooDB: FOOD00057)
Pummelo (FooDB: FOOD00055)
Mandarin orange (Clementine, Tangerine) (FooDB: FOOD00056)
Grapefruit/Pummelo hybrid (FooDB: FOOD00255)
Grapefruit (FooDB: FOOD00256)
Persian lime (FooDB: FOOD00543)
Sour orange (FooDB: FOOD00918)
Mikan (FooDB: FOOD00932)
Clementine (FooDB: FOOD00959)
Citrus (FooDB: FOOD00859)

Pome

Berry

Black crowberry (FooDB: FOOD00075)
Black huckleberry (FooDB: FOOD00084)
Strawberry (FooDB: FOOD00083)
Sea-buckthornberry (FooDB: FOOD00087)
Mulberry (FooDB: FOOD00116)
Black mulberry (FooDB: FOOD00117)
Black chokeberry (FooDB: FOOD00136)
Gooseberry (FooDB: FOOD00157)
Blackcurrant (FooDB: FOOD00155)
Redcurrant (FooDB: FOOD00156)
Cloudberry (FooDB: FOOD00161)
Black raspberry (FooDB: FOOD00163)
Red raspberry (FooDB: FOOD00162)
Black elderberry (FooDB: FOOD00166)
Rowanberry (FooDB: FOOD00176)
Lowbush blueberry (FooDB: FOOD00189)
Sparkleberry (FooDB: FOOD00190)
American cranberry (FooDB: FOOD00192)
Bilberry (FooDB: FOOD00193)
Lingonberry (FooDB: FOOD00194)
Vaccinium (Blueberry, Cranberry, Huckleberry) (FooDB: FOOD00188)
Highbush blueberry (FooDB: FOOD00191)
Muscadine grape (FooDB: FOOD00203)
Common grape (FooDB: FOOD00204)
Bayberry (FooDB: FOOD00209)
Arctic blackberry (FooDB: FOOD00207)
Canada blueberry (FooDB: FOOD00211)
Elliott's blueberry (FooDB: FOOD00210)
Buffalo currant (FooDB: FOOD00213)
Bog bilberry (FooDB: FOOD00212)
Cascade huckleberry (FooDB: FOOD00220)
European cranberry (FooDB: FOOD00217)
Deerberry (FooDB: FOOD00218)
Oval-leaf huckleberry (FooDB: FOOD00221)
Evergreen huckleberry (FooDB: FOOD00222)
Red huckleberry (FooDB: FOOD00223)
Summer grape (FooDB: FOOD00227)
Fox grape (FooDB: FOOD00228)
Half-highbush blueberry (FooDB: FOOD00248)
Jostaberry (FooDB: FOOD00257)
Skunk currant (FooDB: FOOD00267)
Sweet rowanberry (FooDB: FOOD00265)
Squashberry (FooDB: FOOD00344)
Elderberry (FooDB: FOOD00358)
Grape (FooDB: FOOD00369)
Alaska blueberry (FooDB: FOOD00380)
Loganberry (FooDB: FOOD00400)
Ohelo berry (FooDB: FOOD00419)
Salmonberry (FooDB: FOOD00456)
Strawberry guava (FooDB: FOOD00482)
Boysenberry (FooDB: FOOD00542)
Chinese bayberry (FooDB: FOOD00852)
Nanking cherry (FooDB: FOOD00885)
Saskatoon berry (FooDB: FOOD00884)
Rabbiteye blueberry (FooDB: FOOD00898)
Blackberry (FooDB: FOOD00906)
Partridge berry (FooDB: FOOD00931)
Red grape (FooDB: FOOD00965)
Green grape (FooDB: FOOD00964)
Black plum (FooDB: FOOD00966)
Black raisin (FooDB: FOOD00968)
Wampee (FooDB: FOOD00980)
Green plum (FooDB: FOOD00979)
Chinese plum (FooDB: FOOD00978)
Goji (FooDB: FOOD00982)
Hawthorn (FooDB: FOOD00985)
Cape gooseberry (FooDB: FOOD00988)
Monk fruit (FooDB: FOOD00983)
Lantern fruit (FooDB: FOOD00986)
Rubus (Blackberry, Raspberry) (FooDB: FOOD00160)

Other fruit

Fig (FooDB: FOOD00081)
Date (FooDB: FOOD00135)
Jujube (FooDB: FOOD00388)

Drupe

European plum (FooDB: FOOD00147)
Apricot (FooDB: FOOD00144)
Prunus (Cherry, Plum) (FooDB: FOOD00143)
Sweet cherry (FooDB: FOOD00145)
Sour cherry (FooDB: FOOD00146)
Peach (FooDB: FOOD00149)
Nectarine (FooDB: FOOD00229)
Peach (var.) (FooDB: FOOD00230)
Common chokecherry (FooDB: FOOD00562)

Fruits (FooDB: FOOD00871)

Nut

Cashew nut (FooDB: FOOD00011)
Peanut (FooDB: FOOD00016)
Brazil nut (FooDB: FOOD00024)
Chestnut (FooDB: FOOD00045)
Pecan nut (FooDB: FOOD00044)
Common hazelnut (FooDB: FOOD00062)
Common walnut (FooDB: FOOD00094)
Black walnut (FooDB: FOOD00093)
Pine nut (FooDB: FOOD00138)
Pistachio (FooDB: FOOD00140)
Almond (FooDB: FOOD00148)
Macadamia nut (M. tetraphylla) (FooDB: FOOD00225)
Japanese walnut (FooDB: FOOD00240)
Acorn (FooDB: FOOD00282)
Beech nut (FooDB: FOOD00299)
Butternut (FooDB: FOOD00316)
Chinese chestnut (FooDB: FOOD00331)
European chestnut (FooDB: FOOD00363)
Hazelnut (FooDB: FOOD00376)
Hickory nut (FooDB: FOOD00377)
Japanese chestnut (FooDB: FOOD00385)
Pili nut (FooDB: FOOD00432)
Colorado pinyon (FooDB: FOOD00433)
Macadamia nut (FooDB: FOOD00525)
Walnut (FooDB: FOOD00608)
Mixed nuts (FooDB: FOOD00771)
Nuts (FooDB: FOOD00869)

Cereal and cereal product

Cereal

Cereal product

Dough

Sourdough (FooDB: FOOD00275)

Leavened bread

Flat bread

Other bread

Potato bread (FooDB: FOOD00811)
Other bread (FooDB: FOOD00269)

Sweet bread

Raisin bread (FooDB: FOOD00817)

Cereals and cereal products (FooDB: FOOD00858)

Pulse

Pea

Lentil

Lentils (FooDB: FOOD00098)

Other pulse

Lupine (FooDB: FOOD00104)
White lupine (FooDB: FOOD00403)

Bean

Green lentil (FooDB: FOOD00970)
Pulses (FooDB: FOOD00867)

Gourd

Watermelon (FooDB: FOOD00052)
Muskmelon (FooDB: FOOD00064)
Cucumber (FooDB: FOOD00065)
Cucurbita (FooDB: FOOD00066)
Bitter gourd (FooDB: FOOD00115)
Winter squash (FooDB: FOOD00283)
Butternut squash (FooDB: FOOD00317)
Calabash (FooDB: FOOD00318)
Chayote (FooDB: FOOD00325)
Towel gourd (FooDB: FOOD00492)
Wax gourd (FooDB: FOOD00499)
Tinda (FooDB: FOOD00559)
Horned melon (FooDB: FOOD00761)
Sunburst squash (pattypan squash) (FooDB: FOOD00874)
Green zucchini (FooDB: FOOD00875)
Yellow zucchini (FooDB: FOOD00876)
Japanese pumpkin (FooDB: FOOD00886)
Acorn squash (FooDB: FOOD00972)
Cantaloupe melon (FooDB: FOOD00984)

Coffee and coffee product

Coffee

Arabica coffee (FooDB: FOOD00059)
Robusta coffee (FooDB: FOOD00060)

Soy

Soy bean (FooDB: FOOD00085)

Soy product

Dish

Other dish

Taco shell (FooDB: FOOD00991)
Tostada shell (FooDB: FOOD00992)

Tea

Herbal tea

Hibiscus tea (FooDB: FOOD00723)
Greenthread tea (FooDB: FOOD00820)

Baking good

Wrapper

Wonton wrapper (FooDB: FOOD00818)

Abalone (FooDB: FOOD00279)
Conch (FooDB: FOOD00611)

Milk and milk product

Unfermented milk

Milk (Cow) (FooDB: FOOD00618)

Cocoa and cocoa product

Cocoa

Cocoa bean (FooDB: FOOD00182)

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Vitamin B6 Metabolism (HMDB: HMDB0001555)
Vitamin B6 (PathBank: SMP0002387)
Vitamin B6 Metabolism (PathBank: SMP0063472)

Hypophosphatasia (HMDB: HMDB0001555)

Disease pathway

Hypophosphatasia (PathBank: SMP0000503)

Role

Industrial application

Pharmaceutical industry

Pharmaceutical (HMDB: HMDB0001555)

Physical Properties

State

Solid

Experimental Molecular 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

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	MetCCS_train_pos	150.9	30932474
[M+H]+	Not Available	151.075	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000473

Predicted Molecular Properties

Property	Value	Source
Water Solubility	6.61 g/L	ALOGPS
logP	-0.99	ALOGPS
logP	-2.2	ChemAxon
logS	-1.6	ALOGPS
pKa (Strongest Acidic)	1.74	ChemAxon
pKa (Strongest Basic)	9.91	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	125.9 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	56.64 m³·mol⁻¹	ChemAxon
Polarizability	22.15 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	156.708	31661259
DarkChem	[M-H]-	154.746	31661259
AllCCS	[M+H]+	153.972	32859911
AllCCS	[M-H]-	149.875	32859911
DeepCCS	[M+H]+	151.21	30932474
DeepCCS	[M-H]-	148.852	30932474
DeepCCS	[M-2H]-	183.092	30932474
DeepCCS	[M+Na]+	157.628	30932474
AllCCS	[M+H]+	154.0	32859911
AllCCS	[M+H-H2O]+	150.3	32859911
AllCCS	[M+NH4]+	157.4	32859911
AllCCS	[M+Na]+	158.4	32859911
AllCCS	[M-H]-	149.9	32859911
AllCCS	[M+Na-2H]-	150.4	32859911
AllCCS	[M+HCOO]-	151.1	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Pyridoxamine 5'-phosphate	CC1=NC=C(COP(O)(O)=O)C(CN)=C1O	2721.8	Standard polar	33892256
Pyridoxamine 5'-phosphate	CC1=NC=C(COP(O)(O)=O)C(CN)=C1O	2250.4	Standard non polar	33892256
Pyridoxamine 5'-phosphate	CC1=NC=C(COP(O)(O)=O)C(CN)=C1O	2357.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Pyridoxamine 5'-phosphate,1TMS,isomer #1	CC1=NC=C(COP(=O)(O)O)C(CN)=C1O[Si](C)(C)C	2341.5	Semi standard non polar	33892256
Pyridoxamine 5'-phosphate,1TMS,isomer #2	CC1=NC=C(COP(=O)(O)O[Si](C)(C)C)C(CN)=C1O	2390.9	Semi standard non polar	33892256
Pyridoxamine 5'-phosphate,1TMS,isomer #3	CC1=NC=C(COP(=O)(O)O)C(CN[Si](C)(C)C)=C1O	2437.5	Semi standard non polar	33892256
Pyridoxamine 5'-phosphate,2TMS,isomer #1	CC1=NC=C(COP(=O)(O)O[Si](C)(C)C)C(CN)=C1O[Si](C)(C)C	2385.2	Semi standard non polar	33892256
Pyridoxamine 5'-phosphate,2TMS,isomer #1	CC1=NC=C(COP(=O)(O)O[Si](C)(C)C)C(CN)=C1O[Si](C)(C)C	2215.9	Standard non polar	33892256
Pyridoxamine 5'-phosphate,2TMS,isomer #1	CC1=NC=C(COP(=O)(O)O[Si](C)(C)C)C(CN)=C1O[Si](C)(C)C	3153.2	Standard polar	33892256
Pyridoxamine 5'-phosphate,2TMS,isomer #2	CC1=NC=C(COP(=O)(O)O)C(CN[Si](C)(C)C)=C1O[Si](C)(C)C	2385.2	Semi standard non polar	33892256
Pyridoxamine 5'-phosphate,2TMS,isomer #2	CC1=NC=C(COP(=O)(O)O)C(CN[Si](C)(C)C)=C1O[Si](C)(C)C	2353.7	Standard non polar	33892256
Pyridoxamine 5'-phosphate,2TMS,isomer #2	CC1=NC=C(COP(=O)(O)O)C(CN[Si](C)(C)C)=C1O[Si](C)(C)C	3418.2	Standard polar	33892256
Pyridoxamine 5'-phosphate,2TMS,isomer #3	CC1=NC=C(COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)C(CN)=C1O	2397.5	Semi standard non polar	33892256
Pyridoxamine 5'-phosphate,2TMS,isomer #3	CC1=NC=C(COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)C(CN)=C1O	2256.6	Standard non polar	33892256
Pyridoxamine 5'-phosphate,2TMS,isomer #3	CC1=NC=C(COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)C(CN)=C1O	3040.1	Standard polar	33892256
Pyridoxamine 5'-phosphate,2TMS,isomer #4	CC1=NC=C(COP(=O)(O)O[Si](C)(C)C)C(CN[Si](C)(C)C)=C1O	2436.4	Semi standard non polar	33892256
Pyridoxamine 5'-phosphate,2TMS,isomer #4	CC1=NC=C(COP(=O)(O)O[Si](C)(C)C)C(CN[Si](C)(C)C)=C1O	2331.7	Standard non polar	33892256
Pyridoxamine 5'-phosphate,2TMS,isomer #4	CC1=NC=C(COP(=O)(O)O[Si](C)(C)C)C(CN[Si](C)(C)C)=C1O	3154.1	Standard polar	33892256
Pyridoxamine 5'-phosphate,2TMS,isomer #5	CC1=NC=C(COP(=O)(O)O)C(CN([Si](C)(C)C)[Si](C)(C)C)=C1O	2541.5	Semi standard non polar	33892256
Pyridoxamine 5'-phosphate,2TMS,isomer #5	CC1=NC=C(COP(=O)(O)O)C(CN([Si](C)(C)C)[Si](C)(C)C)=C1O	2509.6	Standard non polar	33892256
Pyridoxamine 5'-phosphate,2TMS,isomer #5	CC1=NC=C(COP(=O)(O)O)C(CN([Si](C)(C)C)[Si](C)(C)C)=C1O	3600.9	Standard polar	33892256
Pyridoxamine 5'-phosphate,3TMS,isomer #1	CC1=NC=C(COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)C(CN)=C1O[Si](C)(C)C	2392.0	Semi standard non polar	33892256
Pyridoxamine 5'-phosphate,3TMS,isomer #1	CC1=NC=C(COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)C(CN)=C1O[Si](C)(C)C	2256.7	Standard non polar	33892256
Pyridoxamine 5'-phosphate,3TMS,isomer #1	CC1=NC=C(COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)C(CN)=C1O[Si](C)(C)C	2862.1	Standard polar	33892256
Pyridoxamine 5'-phosphate,3TMS,isomer #2	CC1=NC=C(COP(=O)(O)O[Si](C)(C)C)C(CN[Si](C)(C)C)=C1O[Si](C)(C)C	2431.7	Semi standard non polar	33892256
Pyridoxamine 5'-phosphate,3TMS,isomer #2	CC1=NC=C(COP(=O)(O)O[Si](C)(C)C)C(CN[Si](C)(C)C)=C1O[Si](C)(C)C	2365.1	Standard non polar	33892256
Pyridoxamine 5'-phosphate,3TMS,isomer #2	CC1=NC=C(COP(=O)(O)O[Si](C)(C)C)C(CN[Si](C)(C)C)=C1O[Si](C)(C)C	2891.1	Standard polar	33892256
Pyridoxamine 5'-phosphate,3TMS,isomer #3	CC1=NC=C(COP(=O)(O)O)C(CN([Si](C)(C)C)[Si](C)(C)C)=C1O[Si](C)(C)C	2486.7	Semi standard non polar	33892256
Pyridoxamine 5'-phosphate,3TMS,isomer #3	CC1=NC=C(COP(=O)(O)O)C(CN([Si](C)(C)C)[Si](C)(C)C)=C1O[Si](C)(C)C	2506.6	Standard non polar	33892256
Pyridoxamine 5'-phosphate,3TMS,isomer #3	CC1=NC=C(COP(=O)(O)O)C(CN([Si](C)(C)C)[Si](C)(C)C)=C1O[Si](C)(C)C	3219.5	Standard polar	33892256
Pyridoxamine 5'-phosphate,3TMS,isomer #4	CC1=NC=C(COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)C(CN[Si](C)(C)C)=C1O	2433.0	Semi standard non polar	33892256
Pyridoxamine 5'-phosphate,3TMS,isomer #4	CC1=NC=C(COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)C(CN[Si](C)(C)C)=C1O	2404.3	Standard non polar	33892256
Pyridoxamine 5'-phosphate,3TMS,isomer #4	CC1=NC=C(COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)C(CN[Si](C)(C)C)=C1O	2745.8	Standard polar	33892256
Pyridoxamine 5'-phosphate,3TMS,isomer #5	CC1=NC=C(COP(=O)(O)O[Si](C)(C)C)C(CN([Si](C)(C)C)[Si](C)(C)C)=C1O	2542.8	Semi standard non polar	33892256
Pyridoxamine 5'-phosphate,3TMS,isomer #5	CC1=NC=C(COP(=O)(O)O[Si](C)(C)C)C(CN([Si](C)(C)C)[Si](C)(C)C)=C1O	2508.0	Standard non polar	33892256
Pyridoxamine 5'-phosphate,3TMS,isomer #5	CC1=NC=C(COP(=O)(O)O[Si](C)(C)C)C(CN([Si](C)(C)C)[Si](C)(C)C)=C1O	3029.9	Standard polar	33892256
Pyridoxamine 5'-phosphate,4TMS,isomer #1	CC1=NC=C(COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)C(CN[Si](C)(C)C)=C1O[Si](C)(C)C	2449.4	Semi standard non polar	33892256
Pyridoxamine 5'-phosphate,4TMS,isomer #1	CC1=NC=C(COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)C(CN[Si](C)(C)C)=C1O[Si](C)(C)C	2403.5	Standard non polar	33892256
Pyridoxamine 5'-phosphate,4TMS,isomer #1	CC1=NC=C(COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)C(CN[Si](C)(C)C)=C1O[Si](C)(C)C	2581.6	Standard polar	33892256
Pyridoxamine 5'-phosphate,4TMS,isomer #2	CC1=NC=C(COP(=O)(O)O[Si](C)(C)C)C(CN([Si](C)(C)C)[Si](C)(C)C)=C1O[Si](C)(C)C	2523.2	Semi standard non polar	33892256
Pyridoxamine 5'-phosphate,4TMS,isomer #2	CC1=NC=C(COP(=O)(O)O[Si](C)(C)C)C(CN([Si](C)(C)C)[Si](C)(C)C)=C1O[Si](C)(C)C	2476.4	Standard non polar	33892256
Pyridoxamine 5'-phosphate,4TMS,isomer #2	CC1=NC=C(COP(=O)(O)O[Si](C)(C)C)C(CN([Si](C)(C)C)[Si](C)(C)C)=C1O[Si](C)(C)C	2798.7	Standard polar	33892256
Pyridoxamine 5'-phosphate,4TMS,isomer #3	CC1=NC=C(COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)C(CN([Si](C)(C)C)[Si](C)(C)C)=C1O	2522.1	Semi standard non polar	33892256
Pyridoxamine 5'-phosphate,4TMS,isomer #3	CC1=NC=C(COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)C(CN([Si](C)(C)C)[Si](C)(C)C)=C1O	2537.7	Standard non polar	33892256
Pyridoxamine 5'-phosphate,4TMS,isomer #3	CC1=NC=C(COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)C(CN([Si](C)(C)C)[Si](C)(C)C)=C1O	2695.8	Standard polar	33892256
Pyridoxamine 5'-phosphate,5TMS,isomer #1	CC1=NC=C(COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)C(CN([Si](C)(C)C)[Si](C)(C)C)=C1O[Si](C)(C)C	2535.7	Semi standard non polar	33892256
Pyridoxamine 5'-phosphate,5TMS,isomer #1	CC1=NC=C(COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)C(CN([Si](C)(C)C)[Si](C)(C)C)=C1O[Si](C)(C)C	2492.5	Standard non polar	33892256
Pyridoxamine 5'-phosphate,5TMS,isomer #1	CC1=NC=C(COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)C(CN([Si](C)(C)C)[Si](C)(C)C)=C1O[Si](C)(C)C	2562.4	Standard polar	33892256
Pyridoxamine 5'-phosphate,1TBDMS,isomer #1	CC1=NC=C(COP(=O)(O)O)C(CN)=C1O[Si](C)(C)C(C)(C)C	2624.2	Semi standard non polar	33892256
Pyridoxamine 5'-phosphate,1TBDMS,isomer #2	CC1=NC=C(COP(=O)(O)O[Si](C)(C)C(C)(C)C)C(CN)=C1O	2651.6	Semi standard non polar	33892256
Pyridoxamine 5'-phosphate,1TBDMS,isomer #3	CC1=NC=C(COP(=O)(O)O)C(CN[Si](C)(C)C(C)(C)C)=C1O	2709.3	Semi standard non polar	33892256
Pyridoxamine 5'-phosphate,2TBDMS,isomer #1	CC1=NC=C(COP(=O)(O)O[Si](C)(C)C(C)(C)C)C(CN)=C1O[Si](C)(C)C(C)(C)C	2857.6	Semi standard non polar	33892256
Pyridoxamine 5'-phosphate,2TBDMS,isomer #1	CC1=NC=C(COP(=O)(O)O[Si](C)(C)C(C)(C)C)C(CN)=C1O[Si](C)(C)C(C)(C)C	2607.8	Standard non polar	33892256
Pyridoxamine 5'-phosphate,2TBDMS,isomer #1	CC1=NC=C(COP(=O)(O)O[Si](C)(C)C(C)(C)C)C(CN)=C1O[Si](C)(C)C(C)(C)C	3283.0	Standard polar	33892256
Pyridoxamine 5'-phosphate,2TBDMS,isomer #2	CC1=NC=C(COP(=O)(O)O)C(CN[Si](C)(C)C(C)(C)C)=C1O[Si](C)(C)C(C)(C)C	2844.1	Semi standard non polar	33892256
Pyridoxamine 5'-phosphate,2TBDMS,isomer #2	CC1=NC=C(COP(=O)(O)O)C(CN[Si](C)(C)C(C)(C)C)=C1O[Si](C)(C)C(C)(C)C	2763.6	Standard non polar	33892256
Pyridoxamine 5'-phosphate,2TBDMS,isomer #2	CC1=NC=C(COP(=O)(O)O)C(CN[Si](C)(C)C(C)(C)C)=C1O[Si](C)(C)C(C)(C)C	3504.8	Standard polar	33892256
Pyridoxamine 5'-phosphate,2TBDMS,isomer #3	CC1=NC=C(COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)C(CN)=C1O	2894.1	Semi standard non polar	33892256
Pyridoxamine 5'-phosphate,2TBDMS,isomer #3	CC1=NC=C(COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)C(CN)=C1O	2623.7	Standard non polar	33892256
Pyridoxamine 5'-phosphate,2TBDMS,isomer #3	CC1=NC=C(COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)C(CN)=C1O	3165.2	Standard polar	33892256
Pyridoxamine 5'-phosphate,2TBDMS,isomer #4	CC1=NC=C(COP(=O)(O)O[Si](C)(C)C(C)(C)C)C(CN[Si](C)(C)C(C)(C)C)=C1O	2884.8	Semi standard non polar	33892256
Pyridoxamine 5'-phosphate,2TBDMS,isomer #4	CC1=NC=C(COP(=O)(O)O[Si](C)(C)C(C)(C)C)C(CN[Si](C)(C)C(C)(C)C)=C1O	2745.2	Standard non polar	33892256
Pyridoxamine 5'-phosphate,2TBDMS,isomer #4	CC1=NC=C(COP(=O)(O)O[Si](C)(C)C(C)(C)C)C(CN[Si](C)(C)C(C)(C)C)=C1O	3292.5	Standard polar	33892256
Pyridoxamine 5'-phosphate,2TBDMS,isomer #5	CC1=NC=C(COP(=O)(O)O)C(CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C1O	2971.3	Semi standard non polar	33892256
Pyridoxamine 5'-phosphate,2TBDMS,isomer #5	CC1=NC=C(COP(=O)(O)O)C(CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C1O	2884.4	Standard non polar	33892256
Pyridoxamine 5'-phosphate,2TBDMS,isomer #5	CC1=NC=C(COP(=O)(O)O)C(CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C1O	3607.8	Standard polar	33892256
Pyridoxamine 5'-phosphate,3TBDMS,isomer #1	CC1=NC=C(COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)C(CN)=C1O[Si](C)(C)C(C)(C)C	3064.6	Semi standard non polar	33892256
Pyridoxamine 5'-phosphate,3TBDMS,isomer #1	CC1=NC=C(COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)C(CN)=C1O[Si](C)(C)C(C)(C)C	2732.8	Standard non polar	33892256
Pyridoxamine 5'-phosphate,3TBDMS,isomer #1	CC1=NC=C(COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)C(CN)=C1O[Si](C)(C)C(C)(C)C	3052.4	Standard polar	33892256
Pyridoxamine 5'-phosphate,3TBDMS,isomer #2	CC1=NC=C(COP(=O)(O)O[Si](C)(C)C(C)(C)C)C(CN[Si](C)(C)C(C)(C)C)=C1O[Si](C)(C)C(C)(C)C	3071.0	Semi standard non polar	33892256
Pyridoxamine 5'-phosphate,3TBDMS,isomer #2	CC1=NC=C(COP(=O)(O)O[Si](C)(C)C(C)(C)C)C(CN[Si](C)(C)C(C)(C)C)=C1O[Si](C)(C)C(C)(C)C	2912.5	Standard non polar	33892256
Pyridoxamine 5'-phosphate,3TBDMS,isomer #2	CC1=NC=C(COP(=O)(O)O[Si](C)(C)C(C)(C)C)C(CN[Si](C)(C)C(C)(C)C)=C1O[Si](C)(C)C(C)(C)C	3133.2	Standard polar	33892256
Pyridoxamine 5'-phosphate,3TBDMS,isomer #3	CC1=NC=C(COP(=O)(O)O)C(CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C1O[Si](C)(C)C(C)(C)C	3150.2	Semi standard non polar	33892256
Pyridoxamine 5'-phosphate,3TBDMS,isomer #3	CC1=NC=C(COP(=O)(O)O)C(CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C1O[Si](C)(C)C(C)(C)C	3046.1	Standard non polar	33892256
Pyridoxamine 5'-phosphate,3TBDMS,isomer #3	CC1=NC=C(COP(=O)(O)O)C(CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C1O[Si](C)(C)C(C)(C)C	3362.1	Standard polar	33892256
Pyridoxamine 5'-phosphate,3TBDMS,isomer #4	CC1=NC=C(COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)C(CN[Si](C)(C)C(C)(C)C)=C1O	3103.5	Semi standard non polar	33892256
Pyridoxamine 5'-phosphate,3TBDMS,isomer #4	CC1=NC=C(COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)C(CN[Si](C)(C)C(C)(C)C)=C1O	2922.2	Standard non polar	33892256
Pyridoxamine 5'-phosphate,3TBDMS,isomer #4	CC1=NC=C(COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)C(CN[Si](C)(C)C(C)(C)C)=C1O	3043.3	Standard polar	33892256
Pyridoxamine 5'-phosphate,3TBDMS,isomer #5	CC1=NC=C(COP(=O)(O)O[Si](C)(C)C(C)(C)C)C(CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C1O	3192.7	Semi standard non polar	33892256
Pyridoxamine 5'-phosphate,3TBDMS,isomer #5	CC1=NC=C(COP(=O)(O)O[Si](C)(C)C(C)(C)C)C(CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C1O	3048.4	Standard non polar	33892256
Pyridoxamine 5'-phosphate,3TBDMS,isomer #5	CC1=NC=C(COP(=O)(O)O[Si](C)(C)C(C)(C)C)C(CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C1O	3232.9	Standard polar	33892256
Pyridoxamine 5'-phosphate,4TBDMS,isomer #1	CC1=NC=C(COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)C(CN[Si](C)(C)C(C)(C)C)=C1O[Si](C)(C)C(C)(C)C	3276.9	Semi standard non polar	33892256
Pyridoxamine 5'-phosphate,4TBDMS,isomer #1	CC1=NC=C(COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)C(CN[Si](C)(C)C(C)(C)C)=C1O[Si](C)(C)C(C)(C)C	3023.2	Standard non polar	33892256
Pyridoxamine 5'-phosphate,4TBDMS,isomer #1	CC1=NC=C(COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)C(CN[Si](C)(C)C(C)(C)C)=C1O[Si](C)(C)C(C)(C)C	2971.9	Standard polar	33892256
Pyridoxamine 5'-phosphate,4TBDMS,isomer #2	CC1=NC=C(COP(=O)(O)O[Si](C)(C)C(C)(C)C)C(CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C1O[Si](C)(C)C(C)(C)C	3379.7	Semi standard non polar	33892256
Pyridoxamine 5'-phosphate,4TBDMS,isomer #2	CC1=NC=C(COP(=O)(O)O[Si](C)(C)C(C)(C)C)C(CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C1O[Si](C)(C)C(C)(C)C	3146.5	Standard non polar	33892256
Pyridoxamine 5'-phosphate,4TBDMS,isomer #2	CC1=NC=C(COP(=O)(O)O[Si](C)(C)C(C)(C)C)C(CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C1O[Si](C)(C)C(C)(C)C	3094.4	Standard polar	33892256
Pyridoxamine 5'-phosphate,4TBDMS,isomer #3	CC1=NC=C(COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)C(CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C1O	3383.1	Semi standard non polar	33892256
Pyridoxamine 5'-phosphate,4TBDMS,isomer #3	CC1=NC=C(COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)C(CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C1O	3164.2	Standard non polar	33892256
Pyridoxamine 5'-phosphate,4TBDMS,isomer #3	CC1=NC=C(COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)C(CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C1O	3037.5	Standard polar	33892256
Pyridoxamine 5'-phosphate,5TBDMS,isomer #1	CC1=NC=C(COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)C(CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C1O[Si](C)(C)C(C)(C)C	3561.0	Semi standard non polar	33892256
Pyridoxamine 5'-phosphate,5TBDMS,isomer #1	CC1=NC=C(COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)C(CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C1O[Si](C)(C)C(C)(C)C	3251.7	Standard non polar	33892256
Pyridoxamine 5'-phosphate,5TBDMS,isomer #1	CC1=NC=C(COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)C(CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C1O[Si](C)(C)C(C)(C)C	3000.8	Standard polar	33892256

Spectra

Biological Properties

Cellular Locations

Mitochondria

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Name	SMPDB/PathBank	KEGG
Vitamin B6 Metabolism
Hypophosphatasia		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.015 +/- 0.005 uM	Adult (>18 years old)	Both	Normal	Geigy Scientific ...	details
Blood	Detected and Quantified	0.00098 +/- 0.00019 uM	Adult (>18 years old)	Both	Normal	1783639	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB02142

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

1053

PDB ID

Not Available

ChEBI ID

18335

Food Biomarker Ontology

Not Available

VMH ID

PYAM5P

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Katsunishi, Masatoshi; Kondo, Osamu. Pyridoxamine-5'-phosphate. Jpn. Tokkyo Koho (1972), 2 pp.

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Not Available

Enzymes

Enzyme Details

1. Pyridoxine-5'-phosphate oxidase

General function:: Involved in pyridoxamine-phosphate oxidase activity
Specific function:: Catalyzes the oxidation of either pyridoxine 5'-phosphate (PNP) or pyridoxamine 5'-phosphate (PMP) into pyridoxal 5'-phosphate (PLP).
Gene Name:: PNPO
Uniprot ID:: Q9NVS9
Molecular weight:: 29987.79

Reactions

Pyridoxamine 5'-phosphate + Water + Oxygen → Pyridoxal 5'-phosphate + Ammonia + Hydrogen peroxide	details

Enzyme Details

2. Pyridoxal kinase

General function:: Involved in pyridoxal kinase activity
Specific function:: Required for synthesis of pyridoxal-5-phosphate from vitamin B6.
Gene Name:: PDXK
Uniprot ID:: O00764
Molecular weight:: 35102.105

Reactions

Adenosine triphosphate + Pyridoxamine → ADP + Pyridoxamine 5'-phosphate	details

Enzyme Details

3. Pyridoxal phosphate phosphatase

General function:: Involved in catalytic activity
Specific function:: Protein serine phosphatase that dephosphorylates 'Ser-3' in cofilin and probably also dephosphorylates phospho-serine residues in DSTN. Regulates cofilin-dependent actin cytoskeleton reorganization. Required for normal progress through mitosis and normal cytokinesis. Does not dephosphorylate phospho-threonines in LIMK1. Does not dephosphorylate peptides containing phospho-tyrosine. Pyridoxal phosphate phosphatase. Has some activity towards pyridoxal 5'-phosphate (PLP), pyridoxine 5'-phosphate (PMP) and pyridoxine 5'-phosphate (PNP), with a highest activity with PLP followed by PNP.
Gene Name:: PDXP
Uniprot ID:: Q96GD0
Molecular weight:: 31697.735

Reactions

Pyridoxamine + Phosphate → Pyridoxamine 5'-phosphate + Water	details

Enzyme Details

4. Pyridoxal phosphate phosphatase PHOSPHO2

General function:: Involved in phosphatase activity
Specific function:: Phosphatase that has high activity toward pyridoxal 5'-phosphate (PLP). Also active at much lower level toward pyrophosphate, phosphoethanolamine (PEA), phosphocholine (PCho), phospho-l-tyrosine, fructose-6-phosphate, p-nitrophenyl phosphate, and h-glycerophosphate.
Gene Name:: PHOSPHO2
Uniprot ID:: Q8TCD6
Molecular weight:: 27768.72

Reactions

Pyridoxamine + Phosphate → Pyridoxamine 5'-phosphate + Water	details

Showing metabocard for Pyridoxamine 5'-phosphate (HMDB0001555)

MOL for HMDB0001555 (Pyridoxamine 5'-phosphate)

3D MOL for HMDB0001555 (Pyridoxamine 5'-phosphate)

3D SDF for HMDB0001555 (Pyridoxamine 5'-phosphate)

3D-SDF for HMDB0001555 (Pyridoxamine 5'-phosphate)

PDB for HMDB0001555 (Pyridoxamine 5'-phosphate)

3D PDB for HMDB0001555 (Pyridoxamine 5'-phosphate)

SMILES for HMDB0001555 (Pyridoxamine 5'-phosphate)

INCHI for HMDB0001555 (Pyridoxamine 5'-phosphate)

Structure for HMDB0001555 (Pyridoxamine 5'-phosphate)

3D Structure for HMDB0001555 (Pyridoxamine 5'-phosphate)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

Enzymes

Reactions

Reactions

Reactions

Reactions