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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2021-09-14 15:44:40 UTC

HMDB ID

HMDB0000481

Secondary Accession Numbers

HMDB00481

Metabolite Identification

Common Name

Allopurinol riboside

Description

Allopurinol is an analog of the natural purines in the body, and is quickly metabolized to oxypurines which is also a xanthine oxidase inhibitor. Allopurinol is a white, powdery drug used to treat gout. Its use in the United States was started in 1964. It is an isomer of hypoxanthine and inhibits the production of uric acid, the metabolite responsible for gout, by inhibiting the enzyme xanthine oxidase. The side effects of high levels of precursors are usually minor. A small percentage of people develop a rash and must discontinue this drug. The most serious adverse event is a hypersensitivity syndrome consisting of fever, skin rash, eosinophilia, hepatitis, and worsening renal function. In some cases, allopurinol hypersensitivity syndrome.

Structure

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

HMDB0000481
     RDKit          3D
Allopurinol riboside
 31 33  0  0  0  0  0  0  0  0999 V2000
    5.3862   -1.3135   -0.6162 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4288   -0.7176   -0.0796 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6804    0.1917    0.8721 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6962    0.8756    1.4968 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4304    0.6153    1.1317 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0926   -0.2856    0.1818 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1285   -0.9732   -0.4427 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5068   -1.8110   -1.3498 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1838   -1.5928   -1.2289 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9090   -0.6918   -0.3266 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3698   -0.1643    0.1149 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4189   -1.0604   -0.1696 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5248   -0.2395    0.0575 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.8178   -0.9219   -0.3081 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9376   -2.0623    0.4688 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2112    0.9371   -0.8350 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.9326    2.0668   -0.4562 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7268    1.1250   -0.5587 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6063    2.2120    0.3112 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8594    1.6135    2.2659 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6348    1.1327    1.6002 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0501   -2.4811   -1.9946 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4038    0.0060    1.2109 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5032    0.1029    1.0932 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6394   -0.2337    0.0131 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8824   -1.0927   -1.3819 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4197   -1.9426    1.2946 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4017    0.7295   -1.8945 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3544    2.8216   -0.2190 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1599    1.2873   -1.5040 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6769    1.8671    1.2527 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 13 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
  7  2  1  0
 18 11  1  0
 10  6  1  0
  4 20  1  0
  5 21  1  0
  8 22  1  0
 11 23  1  1
 13 24  1  1
 14 25  1  0
 14 26  1  0
 15 27  1  0
 16 28  1  6
 17 29  1  0
 18 30  1  6
 19 31  1  0
M  END


  Mrv0541 02231218332D          

 19 21  0  0  1  0            999 V2000
   11.8229   -8.5525    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   11.8229   -9.3775    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   12.6076   -9.6325    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   13.0925   -8.9650    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   12.6076   -8.2976    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.1555   -8.0676    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.9175   -8.9650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8625  -10.4171    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.1555   -9.8624    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.1555   -7.2426    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.3709   -6.9876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8859   -7.6551    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3709   -8.3225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3300   -9.6795    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0655   -7.7413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7299   -8.4950    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.2148   -9.1624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0353   -9.0762    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.5806   -7.0739    0.0000 O   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  1  0  0  0  0
  4  5  1  0  0  0  0
  5  1  1  0  0  0  0
  1  6  1  6  0  0  0
  4  7  1  6  0  0  0
  3  8  1  1  0  0  0
  2  9  1  1  0  0  0
  6 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13  6  1  0  0  0  0
  7 14  1  0  0  0  0
 12 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 13  1  0  0  0  0
 15 19  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0000481

> <DATABASE_NAME>
hmdb

> <SMILES>
OC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1N=CC2=C1NC=NC2=O

> <INCHI_IDENTIFIER>
InChI=1S/C10H12N4O5/c15-2-5-6(16)7(17)10(19-5)14-8-4(1-13-14)9(18)12-3-11-8/h1,3,5-7,10,15-17H,2H2,(H,11,12,18)/t5-,6-,7-,10-/m1/s1

> <INCHI_KEY>
KFQUAMTWOJHPEJ-DAGMQNCNSA-N

> <FORMULA>
C10H12N4O5

> <MOLECULAR_WEIGHT>
268.2261

> <EXACT_MASS>
268.080769514

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_AVERAGE_POLARIZABILITY>
24.347949928104413

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1H,4H,7H-pyrazolo[3,4-d]pyrimidin-4-one

> <ALOGPS_LOGP>
-1.70

> <JCHEM_LOGP>
-2.024123547

> <ALOGPS_LOGS>
-1.26

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.423756016437885

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.3612591943656644

> <JCHEM_PKA_STRONGEST_BASIC>
-1.5189939356264377

> <JCHEM_POLAR_SURFACE_AREA>
129.20000000000002

> <JCHEM_REFRACTIVITY>
72.32229999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.48e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-7H-pyrazolo[3,4-d]pyrimidin-4-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0000481
     RDKit          3D
Allopurinol riboside
 31 33  0  0  0  0  0  0  0  0999 V2000
    5.3862   -1.3135   -0.6162 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4288   -0.7176   -0.0796 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6804    0.1917    0.8721 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6962    0.8756    1.4968 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4304    0.6153    1.1317 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0926   -0.2856    0.1818 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1285   -0.9732   -0.4427 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5068   -1.8110   -1.3498 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1838   -1.5928   -1.2289 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9090   -0.6918   -0.3266 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3698   -0.1643    0.1149 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4189   -1.0604   -0.1696 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5248   -0.2395    0.0575 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.8178   -0.9219   -0.3081 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9376   -2.0623    0.4688 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2112    0.9371   -0.8350 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.9326    2.0668   -0.4562 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7268    1.1250   -0.5587 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6063    2.2120    0.3112 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8594    1.6135    2.2659 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6348    1.1327    1.6002 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0501   -2.4811   -1.9946 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4038    0.0060    1.2109 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5032    0.1029    1.0932 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6394   -0.2337    0.0131 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8824   -1.0927   -1.3819 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4197   -1.9426    1.2946 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4017    0.7295   -1.8945 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3544    2.8216   -0.2190 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1599    1.2873   -1.5040 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6769    1.8671    1.2527 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 13 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
  7  2  1  0
 18 11  1  0
 10  6  1  0
  4 20  1  0
  5 21  1  0
  8 22  1  0
 11 23  1  1
 13 24  1  1
 14 25  1  0
 14 26  1  0
 15 27  1  0
 16 28  1  6
 17 29  1  0
 18 30  1  6
 19 31  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  C   UNK     0      22.069 -15.965   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      22.069 -17.505   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      23.534 -17.981   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      24.439 -16.735   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      23.534 -15.489   0.000  0.00  0.00           O+0
HETATM    6  N   UNK     0      20.824 -15.060   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0      25.979 -16.735   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      24.010 -19.445   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0      20.824 -18.410   0.000  0.00  0.00           O+0
HETATM   10  N   UNK     0      20.824 -13.520   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0      19.359 -13.044   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      18.454 -14.290   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      19.359 -15.535   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      26.749 -18.068   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      16.922 -14.450   0.000  0.00  0.00           C+0
HETATM   16  N   UNK     0      16.296 -15.857   0.000  0.00  0.00           N+0
HETATM   17  C   UNK     0      17.201 -17.103   0.000  0.00  0.00           C+0
HETATM   18  N   UNK     0      18.733 -16.942   0.000  0.00  0.00           N+0
HETATM   19  O   UNK     0      16.017 -13.205   0.000  0.00  0.00           O+0
CONECT    1    2    5    6                                                  
CONECT    2    1    3    9                                                  
CONECT    3    2    4    8                                                  
CONECT    4    3    5    7                                                  
CONECT    5    4    1                                                       
CONECT    6    1   10   13                                                  
CONECT    7    4   14                                                       
CONECT    8    3                                                            
CONECT    9    2                                                            
CONECT   10    6   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   15                                                  
CONECT   13   12    6   18                                                  
CONECT   14    7                                                            
CONECT   15   12   16   19                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   13                                                       
CONECT   19   15                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   42    0
END

COMPND    HMDB0000481
HETATM    1  O1  UNL     1       5.386  -1.314  -0.616  1.00  0.00           O  
HETATM    2  C1  UNL     1       4.429  -0.718  -0.080  1.00  0.00           C  
HETATM    3  N1  UNL     1       4.680   0.192   0.872  1.00  0.00           N  
HETATM    4  C2  UNL     1       3.696   0.876   1.497  1.00  0.00           C  
HETATM    5  N2  UNL     1       2.430   0.615   1.132  1.00  0.00           N  
HETATM    6  C3  UNL     1       2.093  -0.286   0.182  1.00  0.00           C  
HETATM    7  C4  UNL     1       3.129  -0.973  -0.443  1.00  0.00           C  
HETATM    8  C5  UNL     1       2.507  -1.811  -1.350  1.00  0.00           C  
HETATM    9  N3  UNL     1       1.184  -1.593  -1.229  1.00  0.00           N  
HETATM   10  N4  UNL     1       0.909  -0.692  -0.327  1.00  0.00           N  
HETATM   11  C6  UNL     1      -0.370  -0.164   0.115  1.00  0.00           C  
HETATM   12  O2  UNL     1      -1.419  -1.060  -0.170  1.00  0.00           O  
HETATM   13  C7  UNL     1      -2.525  -0.239   0.057  1.00  0.00           C  
HETATM   14  C8  UNL     1      -3.818  -0.922  -0.308  1.00  0.00           C  
HETATM   15  O3  UNL     1      -3.938  -2.062   0.469  1.00  0.00           O  
HETATM   16  C9  UNL     1      -2.211   0.937  -0.835  1.00  0.00           C  
HETATM   17  O4  UNL     1      -2.933   2.067  -0.456  1.00  0.00           O  
HETATM   18  C10 UNL     1      -0.727   1.125  -0.559  1.00  0.00           C  
HETATM   19  O5  UNL     1      -0.606   2.212   0.311  1.00  0.00           O  
HETATM   20  H1  UNL     1       3.859   1.613   2.266  1.00  0.00           H  
HETATM   21  H2  UNL     1       1.635   1.133   1.600  1.00  0.00           H  
HETATM   22  H3  UNL     1       3.050  -2.481  -1.995  1.00  0.00           H  
HETATM   23  H4  UNL     1      -0.404   0.006   1.211  1.00  0.00           H  
HETATM   24  H5  UNL     1      -2.503   0.103   1.093  1.00  0.00           H  
HETATM   25  H6  UNL     1      -4.639  -0.234   0.013  1.00  0.00           H  
HETATM   26  H7  UNL     1      -3.882  -1.093  -1.382  1.00  0.00           H  
HETATM   27  H8  UNL     1      -3.420  -1.943   1.295  1.00  0.00           H  
HETATM   28  H9  UNL     1      -2.402   0.730  -1.894  1.00  0.00           H  
HETATM   29  H10 UNL     1      -2.354   2.822  -0.219  1.00  0.00           H  
HETATM   30  H11 UNL     1      -0.160   1.287  -1.504  1.00  0.00           H  
HETATM   31  H12 UNL     1      -0.677   1.867   1.253  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    7
CONECT    3    4    4
CONECT    4    5   20
CONECT    5    6   21
CONECT    6    7    7   10
CONECT    7    8
CONECT    8    9    9   22
CONECT    9   10
CONECT   10   11
CONECT   11   12   18   23
CONECT   12   13
CONECT   13   14   16   24
CONECT   14   15   25   26
CONECT   15   27
CONECT   16   17   18   28
CONECT   17   29
CONECT   18   19   30
CONECT   19   31
END

HMDB0000481
     RDKit          3D
Allopurinol riboside
 31 33  0  0  0  0  0  0  0  0999 V2000
    5.3862   -1.3135   -0.6162 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4288   -0.7176   -0.0796 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6804    0.1917    0.8721 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6962    0.8756    1.4968 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4304    0.6153    1.1317 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0926   -0.2856    0.1818 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1285   -0.9732   -0.4427 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5068   -1.8110   -1.3498 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1838   -1.5928   -1.2289 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9090   -0.6918   -0.3266 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3698   -0.1643    0.1149 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4189   -1.0604   -0.1696 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5248   -0.2395    0.0575 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.8178   -0.9219   -0.3081 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9376   -2.0623    0.4688 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2112    0.9371   -0.8350 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.9326    2.0668   -0.4562 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7268    1.1250   -0.5587 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6063    2.2120    0.3112 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8594    1.6135    2.2659 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6348    1.1327    1.6002 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0501   -2.4811   -1.9946 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4038    0.0060    1.2109 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5032    0.1029    1.0932 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6394   -0.2337    0.0131 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8824   -1.0927   -1.3819 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4197   -1.9426    1.2946 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4017    0.7295   -1.8945 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3544    2.8216   -0.2190 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1599    1.2873   -1.5040 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6769    1.8671    1.2527 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 13 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
  7  2  1  0
 18 11  1  0
 10  6  1  0
  4 20  1  0
  5 21  1  0
  8 22  1  0
 11 23  1  1
 13 24  1  1
 14 25  1  0
 14 26  1  0
 15 27  1  0
 16 28  1  6
 17 29  1  0
 18 30  1  6
 19 31  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
4-Hydroxy[3,4-D]pyrazolopyrimidine riboside	ChEBI
Allopurinol ribonucleoside	ChEBI
Allopurinol-1-ribonucleoside	ChEBI

Chemical Formula

C₁₀H₁₂N₄O₅

Average Molecular Weight

268.2261

Monoisotopic Molecular Weight

268.080769514

IUPAC Name

1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1H,4H,7H-pyrazolo[3,4-d]pyrimidin-4-one

Traditional Name

1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-7H-pyrazolo[3,4-d]pyrimidin-4-one

CAS Registry Number

16220-07-8

SMILES

OC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1N=CC2=C1NC=NC2=O

InChI Identifier

InChI=1S/C10H12N4O5/c15-2-5-6(16)7(17)10(19-5)14-8-4(1-13-14)9(18)12-3-11-8/h1,3,5-7,10,15-17H,2H2,(H,11,12,18)/t5-,6-,7-,10-/m1/s1

InChI Key

KFQUAMTWOJHPEJ-DAGMQNCNSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pyrazolo[3,4-d]pyrimidine glycosides. These are nucleosides or derivatives thereof that consist of a pyazolo[3,2-d]pyrimidine ring system that is N-glycosidically linked to a ribose or deoxyribose. They bear the sugar moiety on the pyrimidine part of the molecule.

Kingdom

Organic compounds

Super Class

Nucleosides, nucleotides, and analogues

Class

Pyrazolo[3,4-d]pyrimidine glycosides

Sub Class

Not Available

Direct Parent

Pyrazolo[3,4-d]pyrimidine glycosides

Alternative Parents

Substituents

Pyrazolo[3,4-d]pyrimidine glycoside
Glycosyl compound
N-glycosyl compound
Pentose monosaccharide
Pyrazolo[3,4-d]pyrimidine
Pyrazolopyrimidine
Pyrimidone
Monosaccharide
Pyrimidine
Azole
Heteroaromatic compound
Pyrazole
Vinylogous amide
Tetrahydrofuran
Secondary alcohol
Organoheterocyclic compound
Azacycle
Oxacycle
Primary alcohol
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

nucleoside analogue (CHEBI:74074 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 838831)

Cellular substructure

Cytoplasm (HMDB: HMDB0000481)

Source

Endogenous

Endogenous (HMDB: HMDB0000481)

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

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

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

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

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

Equine

Horse (FooDB: FOOD00378)

Process

Not Available

Role

Not Available

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

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	14.8 g/L	ALOGPS
logP	-1.7	ALOGPS
logP	-2	ChemAxon
logS	-1.3	ALOGPS
pKa (Strongest Acidic)	7.36	ChemAxon
pKa (Strongest Basic)	-1.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	129.2 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	72.32 m³·mol⁻¹	ChemAxon
Polarizability	24.35 Å³	ChemAxon
Number of Rings	3	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]+	159.854	31661259
DarkChem	[M-H]-	155.813	31661259
AllCCS	[M+H]+	160.434	32859911
AllCCS	[M-H]-	158.437	32859911
DeepCCS	[M+H]+	151.848	30932474
DeepCCS	[M-H]-	149.453	30932474
DeepCCS	[M-2H]-	183.809	30932474
DeepCCS	[M+Na]+	158.495	30932474
AllCCS	[M+H]+	160.4	32859911
AllCCS	[M+H-H2O]+	156.8	32859911
AllCCS	[M+NH4]+	163.8	32859911
AllCCS	[M+Na]+	164.8	32859911
AllCCS	[M-H]-	158.4	32859911
AllCCS	[M+Na-2H]-	157.9	32859911
AllCCS	[M+HCOO]-	157.4	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	1.92 minutes	32390414
Predicted by Siyang on May 30, 2022	9.1341 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	5.22 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	185.0 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	627.6 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	246.6 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	61.6 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	160.6 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	50.7 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	299.6 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	257.4 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	667.0 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	568.8 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	57.1 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	764.7 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	177.1 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	205.9 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	606.7 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	377.3 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	303.1 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Allopurinol riboside	OC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1N=CC2=C1NC=NC2=O	3398.3	Standard polar	33892256
Allopurinol riboside	OC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1N=CC2=C1NC=NC2=O	1851.3	Standard non polar	33892256
Allopurinol riboside	OC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1N=CC2=C1NC=NC2=O	2839.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Allopurinol riboside,1TMS,isomer #1	C[Si](C)(C)OC[C@H]1O[C@@H](N2N=CC3=C2[NH]C=NC3=O)[C@H](O)[C@@H]1O	2543.7	Semi standard non polar	33892256
Allopurinol riboside,1TMS,isomer #2	C[Si](C)(C)O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1N=CC2=C1[NH]C=NC2=O	2547.0	Semi standard non polar	33892256
Allopurinol riboside,1TMS,isomer #3	C[Si](C)(C)O[C@@H]1[C@@H](CO)O[C@@H](N2N=CC3=C2[NH]C=NC3=O)[C@@H]1O	2556.0	Semi standard non polar	33892256
Allopurinol riboside,1TMS,isomer #4	C[Si](C)(C)N1C=NC(=O)C2=C1N([C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O)N=C2	2642.8	Semi standard non polar	33892256
Allopurinol riboside,2TMS,isomer #1	C[Si](C)(C)OC[C@H]1O[C@@H](N2N=CC3=C2[NH]C=NC3=O)[C@H](O[Si](C)(C)C)[C@@H]1O	2517.8	Semi standard non polar	33892256
Allopurinol riboside,2TMS,isomer #2	C[Si](C)(C)OC[C@H]1O[C@@H](N2N=CC3=C2[NH]C=NC3=O)[C@H](O)[C@@H]1O[Si](C)(C)C	2523.2	Semi standard non polar	33892256
Allopurinol riboside,2TMS,isomer #3	C[Si](C)(C)OC[C@H]1O[C@@H](N2N=CC3=C2N([Si](C)(C)C)C=NC3=O)[C@H](O)[C@@H]1O	2624.7	Semi standard non polar	33892256
Allopurinol riboside,2TMS,isomer #4	C[Si](C)(C)O[C@@H]1[C@@H](CO)O[C@@H](N2N=CC3=C2[NH]C=NC3=O)[C@@H]1O[Si](C)(C)C	2537.1	Semi standard non polar	33892256
Allopurinol riboside,2TMS,isomer #5	C[Si](C)(C)O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1N=CC2=C1N([Si](C)(C)C)C=NC2=O	2641.8	Semi standard non polar	33892256
Allopurinol riboside,2TMS,isomer #6	C[Si](C)(C)O[C@@H]1[C@@H](CO)O[C@@H](N2N=CC3=C2N([Si](C)(C)C)C=NC3=O)[C@@H]1O	2645.5	Semi standard non polar	33892256
Allopurinol riboside,3TMS,isomer #1	C[Si](C)(C)OC[C@H]1O[C@@H](N2N=CC3=C2[NH]C=NC3=O)[C@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C	2522.7	Semi standard non polar	33892256
Allopurinol riboside,3TMS,isomer #2	C[Si](C)(C)OC[C@H]1O[C@@H](N2N=CC3=C2N([Si](C)(C)C)C=NC3=O)[C@H](O[Si](C)(C)C)[C@@H]1O	2628.5	Semi standard non polar	33892256
Allopurinol riboside,3TMS,isomer #3	C[Si](C)(C)OC[C@H]1O[C@@H](N2N=CC3=C2N([Si](C)(C)C)C=NC3=O)[C@H](O)[C@@H]1O[Si](C)(C)C	2621.0	Semi standard non polar	33892256
Allopurinol riboside,3TMS,isomer #4	C[Si](C)(C)O[C@@H]1[C@@H](CO)O[C@@H](N2N=CC3=C2N([Si](C)(C)C)C=NC3=O)[C@@H]1O[Si](C)(C)C	2641.2	Semi standard non polar	33892256
Allopurinol riboside,4TMS,isomer #1	C[Si](C)(C)OC[C@H]1O[C@@H](N2N=CC3=C2N([Si](C)(C)C)C=NC3=O)[C@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C	2652.6	Semi standard non polar	33892256
Allopurinol riboside,4TMS,isomer #1	C[Si](C)(C)OC[C@H]1O[C@@H](N2N=CC3=C2N([Si](C)(C)C)C=NC3=O)[C@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C	2904.9	Standard non polar	33892256
Allopurinol riboside,4TMS,isomer #1	C[Si](C)(C)OC[C@H]1O[C@@H](N2N=CC3=C2N([Si](C)(C)C)C=NC3=O)[C@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C	3122.0	Standard polar	33892256
Allopurinol riboside,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2N=CC3=C2[NH]C=NC3=O)[C@H](O)[C@@H]1O	2789.8	Semi standard non polar	33892256
Allopurinol riboside,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1N=CC2=C1[NH]C=NC2=O	2791.8	Semi standard non polar	33892256
Allopurinol riboside,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H](CO)O[C@@H](N2N=CC3=C2[NH]C=NC3=O)[C@@H]1O	2800.0	Semi standard non polar	33892256
Allopurinol riboside,1TBDMS,isomer #4	CC(C)(C)[Si](C)(C)N1C=NC(=O)C2=C1N([C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O)N=C2	2897.6	Semi standard non polar	33892256
Allopurinol riboside,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2N=CC3=C2[NH]C=NC3=O)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O	2990.3	Semi standard non polar	33892256
Allopurinol riboside,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2N=CC3=C2[NH]C=NC3=O)[C@H](O)[C@@H]1O[Si](C)(C)C(C)(C)C	2995.6	Semi standard non polar	33892256
Allopurinol riboside,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2N=CC3=C2N([Si](C)(C)C(C)(C)C)C=NC3=O)[C@H](O)[C@@H]1O	3083.8	Semi standard non polar	33892256
Allopurinol riboside,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H](CO)O[C@@H](N2N=CC3=C2[NH]C=NC3=O)[C@@H]1O[Si](C)(C)C(C)(C)C	2986.9	Semi standard non polar	33892256
Allopurinol riboside,2TBDMS,isomer #5	CC(C)(C)[Si](C)(C)O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1N=CC2=C1N([Si](C)(C)C(C)(C)C)C=NC2=O	3081.1	Semi standard non polar	33892256
Allopurinol riboside,2TBDMS,isomer #6	CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H](CO)O[C@@H](N2N=CC3=C2N([Si](C)(C)C(C)(C)C)C=NC3=O)[C@@H]1O	3086.7	Semi standard non polar	33892256
Allopurinol riboside,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2N=CC3=C2[NH]C=NC3=O)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O[Si](C)(C)C(C)(C)C	3181.8	Semi standard non polar	33892256
Allopurinol riboside,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2N=CC3=C2N([Si](C)(C)C(C)(C)C)C=NC3=O)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O	3282.5	Semi standard non polar	33892256
Allopurinol riboside,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2N=CC3=C2N([Si](C)(C)C(C)(C)C)C=NC3=O)[C@H](O)[C@@H]1O[Si](C)(C)C(C)(C)C	3277.4	Semi standard non polar	33892256
Allopurinol riboside,3TBDMS,isomer #4	CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H](CO)O[C@@H](N2N=CC3=C2N([Si](C)(C)C(C)(C)C)C=NC3=O)[C@@H]1O[Si](C)(C)C(C)(C)C	3281.8	Semi standard non polar	33892256
Allopurinol riboside,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2N=CC3=C2N([Si](C)(C)C(C)(C)C)C=NC3=O)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O[Si](C)(C)C(C)(C)C	3444.3	Semi standard non polar	33892256
Allopurinol riboside,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2N=CC3=C2N([Si](C)(C)C(C)(C)C)C=NC3=O)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O[Si](C)(C)C(C)(C)C	3635.7	Standard non polar	33892256
Allopurinol riboside,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2N=CC3=C2N([Si](C)(C)C(C)(C)C)C=NC3=O)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O[Si](C)(C)C(C)(C)C	3443.4	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Allopurinol riboside GC-MS (Non-derivatized) - 70eV, Positive	splash10-0adl-9230000000-f2b42573dba0039df9fc	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Allopurinol riboside GC-MS (3 TMS) - 70eV, Positive	splash10-0gir-5955300000-84fcb654b6b0639a529b	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Allopurinol riboside GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Allopurinol riboside GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Allopurinol riboside GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Allopurinol riboside GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Allopurinol riboside GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Allopurinol riboside GC-MS (TMS_1_4) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Allopurinol riboside GC-MS (TMS_2_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Allopurinol riboside GC-MS (TMS_2_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Allopurinol riboside GC-MS (TMS_2_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Allopurinol riboside GC-MS (TMS_2_4) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Allopurinol riboside GC-MS (TMS_2_5) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Allopurinol riboside GC-MS (TMS_2_6) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Allopurinol riboside GC-MS (TMS_3_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Allopurinol riboside GC-MS (TMS_3_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Allopurinol riboside GC-MS (TMS_3_4) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Allopurinol riboside GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Allopurinol riboside GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Allopurinol riboside GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Allopurinol riboside GC-MS (TBDMS_1_4) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Allopurinol riboside GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Allopurinol riboside GC-MS (TBDMS_2_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Allopurinol riboside GC-MS (TBDMS_2_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Allopurinol riboside GC-MS (TBDMS_2_4) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Allopurinol riboside 10V, Positive-QTOF	splash10-000i-0920000000-a9fa0dd7e6fa50ea6984	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Allopurinol riboside 20V, Positive-QTOF	splash10-000i-0900000000-21c7b658689fb9512f0b	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Allopurinol riboside 40V, Positive-QTOF	splash10-052r-1900000000-a0d5d35743edd0e2288b	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Allopurinol riboside 10V, Negative-QTOF	splash10-000i-0900000000-ab1c150a018c7c95cfcf	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Allopurinol riboside 20V, Negative-QTOF	splash10-000i-0900000000-c23b7002c1cf46d80397	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Allopurinol riboside 40V, Negative-QTOF	splash10-0a4r-4900000000-94845c316294342528a8	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Allopurinol riboside 10V, Negative-QTOF	splash10-014j-0290000000-1fe2c9a9f3ca1ec73a39	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Allopurinol riboside 20V, Negative-QTOF	splash10-000i-0900000000-dc2d53701ff620e1a6e4	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Allopurinol riboside 40V, Negative-QTOF	splash10-000i-4900000000-32ca35fb23ae98d9baef	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Allopurinol riboside 10V, Positive-QTOF	splash10-000i-0910000000-8f996cedd72f2106a9ba	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Allopurinol riboside 20V, Positive-QTOF	splash10-000i-0900000000-2fcf648123cc944c1522	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Allopurinol riboside 40V, Positive-QTOF	splash10-000i-2900000000-36c56b92eacd3d7ca10d	2021-09-25	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	5.0 (0.05-10.0) uM	Adult (>18 years old)	Both	Normal	838831	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022067

KNApSAcK ID

Not Available

Chemspider ID

18512601

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

5468

PubChem Compound

5273534

PDB ID

Not Available

ChEBI ID

74074

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Korbukh, I. A.; Yakunina, N. G.; Preobrazhenskaya, M. N. Synthesis and reactions of 4- and 4,6-substituted pyrazolo[3,4-d]pyrimidine nucleosides. Bioorganicheskaya Khimiya (1980), 6(11), 1632-8.

Material Safety Data Sheet (MSDS)

Not Available

General References

Ledvinova J, Poupetova H, Hanackova A, Pisacka M, Elleder M: Blood group B glycosphingolipids in alpha-galactosidase deficiency (Fabry disease): influence of secretor status. Biochim Biophys Acta. 1997 Apr 1;1345(2):180-7. [PubMed:9106497 ]
Nelson DJ, Elion GB: Metabolic studies of high doses of allopurinol in humans. Adv Exp Med Biol. 1984;165 Pt A:167-70. [PubMed:6720373 ]

Showing metabocard for Allopurinol riboside (HMDB0000481)

MOL for HMDB0000481 (Allopurinol riboside)

3D MOL for HMDB0000481 (Allopurinol riboside)

3D SDF for HMDB0000481 (Allopurinol riboside)

3D-SDF for HMDB0000481 (Allopurinol riboside)

PDB for HMDB0000481 (Allopurinol riboside)

3D PDB for HMDB0000481 (Allopurinol riboside)

SMILES for HMDB0000481 (Allopurinol riboside)

INCHI for HMDB0000481 (Allopurinol riboside)

Structure for HMDB0000481 (Allopurinol riboside)

3D Structure for HMDB0000481 (Allopurinol riboside)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra