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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (2) Show 2 proteins XML

Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2021-09-14 15:44:42 UTC

HMDB ID

HMDB0000071

Secondary Accession Numbers

HMDB00071

Metabolite Identification

Common Name

Deoxyinosine

Description

Deoxyinosine is a nucleoside that is formed when hypoxanthine is attached to a deoxyribose ring (also known as a ribofuranose) via a beta-N9-glycosidic bond. Deoxyinosine is found in DNA while inosine is found in RNA. Inosine is a nucleic acid important for RNA editing. Adenosine deaminase (ADA) catalyzes the conversion of adenosine and deoxyadenosine to inosine and deoxyinosine, respectively. ADA-deficient individuals suffer from severe combined immunodeficiency (SCID) and are unable to produce significant numbers of mature T or B lymphocytes. This occurs as a consequence of the accumulation of ADA substrates or their metabolites. Inosine is also an intermediate in a chain of purine nucleotides reactions required for muscle movements. Moreover, deoxyinosine is found to be associated with purine nucleoside phosphorylase (PNP) deficiency, which is an inborn error of metabolism.

Structure

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

HMDB0000071
     RDKit          3D
Deoxyinosine
 30 32  0  0  0  0  0  0  0  0999 V2000
   -5.0427    1.5528    1.2843 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2093    0.8391    0.6678 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5961    0.0226   -0.3412 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7125   -0.7499   -1.0127 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3871   -0.7392   -0.7003 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9589    0.0464    0.2833 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8609    0.8348    0.9685 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1338    1.4959    1.8794 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8366    1.1426    1.7746 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7265    0.2329    0.7731 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5385   -0.3430    0.4097 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5253   -1.0994   -0.8676 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9677   -0.9175   -1.3603 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6098   -2.1499   -1.4302 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5519   -0.0615   -0.2808 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.7016    0.7858   -0.7385 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0749    1.5914    0.3572 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4562    0.6965    0.1285 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6002    0.0162   -0.5760 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0970   -1.3760   -1.8064 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0511    1.5466    2.4085 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0047   -0.9436    1.2143 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3877   -2.1885   -0.6174 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1896   -0.7600   -1.6139 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0037   -0.4428   -2.3456 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1218   -2.3480   -0.5942 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8759   -0.6542    0.5868 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5644    0.1052   -0.9097 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4733    1.4447   -1.5734 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5450    2.4198    0.3937 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  2  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
 13 15  1  0
 15 16  1  0
 16 17  1  0
 15 18  1  0
  7  2  1  0
 18 11  1  0
 10  6  1  0
  3 19  1  0
  4 20  1  0
  9 21  1  0
 11 22  1  1
 12 23  1  0
 12 24  1  0
 13 25  1  6
 14 26  1  0
 15 27  1  1
 16 28  1  0
 16 29  1  0
 17 30  1  0
M  END

ChEBI
  Mrv1652303182019232D          

 18 20  0  0  1  0            999 V2000
    7.7048  -16.8513    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.7048  -17.6701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4327  -18.0946    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.1605  -17.6701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1605  -16.8513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4327  -16.4266    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9490  -16.5783    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.4342  -17.2758    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9490  -17.9430    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.3433  -20.2176    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.6162  -19.4290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9490  -18.9438    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.2819  -19.4290    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.5244  -20.2176    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.9482  -20.7634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2212  -21.6429    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.8285  -20.9151    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4327  -15.5775    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  6  1  1  0  0  0  0
  3  2  2  0  0  0  0
  4  3  1  0  0  0  0
  5  6  1  0  0  0  0
 18  6  2  0  0  0  0
  7  5  1  0  0  0  0
  4  5  2  0  0  0  0
  9  4  1  0  0  0  0
 12  9  1  1  0  0  0
  8  9  1  0  0  0  0
  7  8  2  0  0  0  0
 11 10  1  0  0  0  0
 14 10  1  0  0  0  0
 10 17  1  6  0  0  0
 12 11  1  0  0  0  0
 13 12  1  0  0  0  0
 14 13  1  0  0  0  0
 14 15  1  1  0  0  0
 16 15  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0000071

> <DATABASE_NAME>
hmdb

> <SMILES>
OC[C@H]1O[C@H](C[C@@H]1O)N1C=NC2=C1N=CNC2=O

> <INCHI_IDENTIFIER>
InChI=1S/C10H12N4O4/c15-2-6-5(16)1-7(18-6)14-4-13-8-9(14)11-3-12-10(8)17/h3-7,15-16H,1-2H2,(H,11,12,17)/t5-,6+,7+/m0/s1

> <INCHI_KEY>
VGONTNSXDCQUGY-RRKCRQDMSA-N

> <FORMULA>
C10H12N4O4

> <MOLECULAR_WEIGHT>
252.23

> <EXACT_MASS>
252.085854882

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
30

> <JCHEM_AVERAGE_POLARIZABILITY>
23.69386736747174

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
9-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-9H-purin-6-ol

> <ALOGPS_LOGP>
-1.67

> <JCHEM_LOGP>
-0.6649651763333334

> <ALOGPS_LOGS>
-1.40

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.889081575302495

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.675326207558905

> <JCHEM_PKA_STRONGEST_BASIC>
-0.10182461793317621

> <JCHEM_POLAR_SURFACE_AREA>
113.52

> <JCHEM_REFRACTIVITY>
58.96539999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.01e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2'-deoxy-inosine

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0000071
     RDKit          3D
Deoxyinosine
 30 32  0  0  0  0  0  0  0  0999 V2000
   -5.0427    1.5528    1.2843 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2093    0.8391    0.6678 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5961    0.0226   -0.3412 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7125   -0.7499   -1.0127 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3871   -0.7392   -0.7003 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9589    0.0464    0.2833 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8609    0.8348    0.9685 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1338    1.4959    1.8794 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8366    1.1426    1.7746 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7265    0.2329    0.7731 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5385   -0.3430    0.4097 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5253   -1.0994   -0.8676 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9677   -0.9175   -1.3603 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6098   -2.1499   -1.4302 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5519   -0.0615   -0.2808 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.7016    0.7858   -0.7385 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0749    1.5914    0.3572 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4562    0.6965    0.1285 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6002    0.0162   -0.5760 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0970   -1.3760   -1.8064 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0511    1.5466    2.4085 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0047   -0.9436    1.2143 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3877   -2.1885   -0.6174 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1896   -0.7600   -1.6139 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0037   -0.4428   -2.3456 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1218   -2.3480   -0.5942 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8759   -0.6542    0.5868 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5644    0.1052   -0.9097 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4733    1.4447   -1.5734 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5450    2.4198    0.3937 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  2  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
 13 15  1  0
 15 16  1  0
 16 17  1  0
 15 18  1  0
  7  2  1  0
 18 11  1  0
 10  6  1  0
  3 19  1  0
  4 20  1  0
  9 21  1  0
 11 22  1  1
 12 23  1  0
 12 24  1  0
 13 25  1  6
 14 26  1  0
 15 27  1  1
 16 28  1  0
 16 29  1  0
 17 30  1  0
M  END

HEADER    PROTEIN                                 18-MAR-20   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: ChEBI                                             
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   18-MAR-20         0                                  
HETATM    1  N   UNK     0      14.382 -31.456   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0      14.382 -32.984   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0      15.741 -33.777   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0      17.100 -32.984   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      17.100 -31.456   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      15.741 -30.663   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0      18.571 -30.946   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0      19.477 -32.248   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0      18.571 -33.494   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0      19.307 -37.740   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      19.817 -36.267   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      18.571 -35.362   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      17.326 -36.267   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      17.779 -37.740   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      16.703 -38.758   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      17.213 -40.400   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      20.213 -39.042   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      15.741 -29.078   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    9                                                  
CONECT    5    6    7    4                                                  
CONECT    6    1    5   18                                                  
CONECT    7    5    8                                                       
CONECT    8    9    7                                                       
CONECT    9    4   12    8                                                  
CONECT   10   11   14   17                                                  
CONECT   11   10   12                                                       
CONECT   12    9   11   13                                                  
CONECT   13   12   14                                                       
CONECT   14   10   13   15                                                  
CONECT   15   14   16                                                       
CONECT   16   15                                                            
CONECT   17   10                                                            
CONECT   18    6                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   40    0
END

COMPND    HMDB0000071
HETATM    1  O1  UNL     1      -5.043   1.553   1.284  1.00  0.00           O  
HETATM    2  C1  UNL     1      -4.209   0.839   0.668  1.00  0.00           C  
HETATM    3  N1  UNL     1      -4.596   0.023  -0.341  1.00  0.00           N  
HETATM    4  C2  UNL     1      -3.712  -0.750  -1.013  1.00  0.00           C  
HETATM    5  N2  UNL     1      -2.387  -0.739  -0.700  1.00  0.00           N  
HETATM    6  C3  UNL     1      -1.959   0.046   0.283  1.00  0.00           C  
HETATM    7  C4  UNL     1      -2.861   0.835   0.969  1.00  0.00           C  
HETATM    8  N3  UNL     1      -2.134   1.496   1.879  1.00  0.00           N  
HETATM    9  C5  UNL     1      -0.837   1.143   1.775  1.00  0.00           C  
HETATM   10  N4  UNL     1      -0.726   0.233   0.773  1.00  0.00           N  
HETATM   11  C6  UNL     1       0.538  -0.343   0.410  1.00  0.00           C  
HETATM   12  C7  UNL     1       0.525  -1.099  -0.868  1.00  0.00           C  
HETATM   13  C8  UNL     1       1.968  -0.917  -1.360  1.00  0.00           C  
HETATM   14  O2  UNL     1       2.610  -2.150  -1.430  1.00  0.00           O  
HETATM   15  C9  UNL     1       2.552  -0.061  -0.281  1.00  0.00           C  
HETATM   16  C10 UNL     1       3.702   0.786  -0.738  1.00  0.00           C  
HETATM   17  O3  UNL     1       4.075   1.591   0.357  1.00  0.00           O  
HETATM   18  O4  UNL     1       1.456   0.697   0.129  1.00  0.00           O  
HETATM   19  H1  UNL     1      -5.600   0.016  -0.576  1.00  0.00           H  
HETATM   20  H2  UNL     1      -4.097  -1.376  -1.806  1.00  0.00           H  
HETATM   21  H3  UNL     1      -0.051   1.547   2.409  1.00  0.00           H  
HETATM   22  H4  UNL     1       1.005  -0.944   1.214  1.00  0.00           H  
HETATM   23  H5  UNL     1       0.388  -2.188  -0.617  1.00  0.00           H  
HETATM   24  H6  UNL     1      -0.190  -0.760  -1.614  1.00  0.00           H  
HETATM   25  H7  UNL     1       2.004  -0.443  -2.346  1.00  0.00           H  
HETATM   26  H8  UNL     1       3.122  -2.348  -0.594  1.00  0.00           H  
HETATM   27  H9  UNL     1       2.876  -0.654   0.587  1.00  0.00           H  
HETATM   28  H10 UNL     1       4.564   0.105  -0.910  1.00  0.00           H  
HETATM   29  H11 UNL     1       3.473   1.445  -1.573  1.00  0.00           H  
HETATM   30  H12 UNL     1       3.545   2.420   0.394  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    7
CONECT    3    4   19
CONECT    4    5    5   20
CONECT    5    6
CONECT    6    7    7   10
CONECT    7    8
CONECT    8    9    9
CONECT    9   10   21
CONECT   10   11
CONECT   11   12   18   22
CONECT   12   13   23   24
CONECT   13   14   15   25
CONECT   14   26
CONECT   15   16   18   27
CONECT   16   17   28   29
CONECT   17   30
END

HMDB0000071
     RDKit          3D
Deoxyinosine
 30 32  0  0  0  0  0  0  0  0999 V2000
   -5.0427    1.5528    1.2843 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2093    0.8391    0.6678 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5961    0.0226   -0.3412 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7125   -0.7499   -1.0127 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3871   -0.7392   -0.7003 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9589    0.0464    0.2833 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8609    0.8348    0.9685 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1338    1.4959    1.8794 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8366    1.1426    1.7746 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7265    0.2329    0.7731 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5385   -0.3430    0.4097 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5253   -1.0994   -0.8676 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9677   -0.9175   -1.3603 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6098   -2.1499   -1.4302 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5519   -0.0615   -0.2808 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.7016    0.7858   -0.7385 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0749    1.5914    0.3572 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4562    0.6965    0.1285 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6002    0.0162   -0.5760 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0970   -1.3760   -1.8064 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0511    1.5466    2.4085 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0047   -0.9436    1.2143 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3877   -2.1885   -0.6174 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1896   -0.7600   -1.6139 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0037   -0.4428   -2.3456 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1218   -2.3480   -0.5942 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8759   -0.6542    0.5868 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5644    0.1052   -0.9097 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4733    1.4447   -1.5734 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5450    2.4198    0.3937 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  2  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
 13 15  1  0
 15 16  1  0
 16 17  1  0
 15 18  1  0
  7  2  1  0
 18 11  1  0
 10  6  1  0
  3 19  1  0
  4 20  1  0
  9 21  1  0
 11 22  1  1
 12 23  1  0
 12 24  1  0
 13 25  1  6
 14 26  1  0
 15 27  1  1
 16 28  1  0
 16 29  1  0
 17 30  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
9-(2-Deoxy-beta-D-erythro-pentofuranosyl)-9H-purin-6-ol	ChEBI
9-(2-Deoxy-b-D-erythro-pentofuranosyl)-9H-purin-6-ol	Generator
9-(2-Deoxy-β-D-erythro-pentofuranosyl)-9H-purin-6-ol	Generator
2'-Deoxyinosine	HMDB
2-Deoxy-inosine	HMDB
9-(2-Deoxy-b-D-erythro-pentofuranosyl)-1,9-dihydro-6H-purin-6-one	HMDB
9-(2-Deoxy-b-D-erythro-pentofuranosyl)-hypoxanthine	HMDB
9-(2-Deoxy-beta-D-erythro-pentofuranosyl)-hypoxanthine	HMDB
9-(2-Deoxy-beta-delta-erythro-pentofuranosyl)-1,9-dihydro-6H-purin-6-one	HMDB
9-(2-Deoxy-beta-delta-erythro-pentofuranosyl)-hypoxanthine	HMDB
D-Ino	HMDB
delta-Ino	HMDB
DInosine	HMDB
Deoxyribose-inosine	HMDB
Deoxyinosine	ChEBI

Chemical Formula

C₁₀H₁₂N₄O₄

Average Molecular Weight

252.23

Monoisotopic Molecular Weight

252.085854882

IUPAC Name

9-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-9H-purin-6-ol

Traditional Name

2'-deoxy-inosine

CAS Registry Number

890-38-0

SMILES

OC[C@H]1O[C@H](C[C@@H]1O)N1C=NC2=C1N=CNC2=O

InChI Identifier

InChI=1S/C10H12N4O4/c15-2-6-5(16)1-7(18-6)14-4-13-8-9(14)11-3-12-10(8)17/h3-7,15-16H,1-2H2,(H,11,12,17)/t5-,6+,7+/m0/s1

InChI Key

VGONTNSXDCQUGY-RRKCRQDMSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as purine 2'-deoxyribonucleosides. Purine 2'-deoxyribonucleosides are compounds consisting of a purine linked to a ribose which lacks a hydroxyl group at position 2.

Kingdom

Organic compounds

Super Class

Nucleosides, nucleotides, and analogues

Class

Purine nucleosides

Sub Class

Purine 2'-deoxyribonucleosides

Direct Parent

Purine 2'-deoxyribonucleosides

Alternative Parents

Substituents

Purine 2'-deoxyribonucleoside
Hypoxanthine
Imidazopyrimidine
Purine
Hydroxypyrimidine
N-substituted imidazole
Pyrimidine
Tetrahydrofuran
Heteroaromatic compound
Azole
Imidazole
Secondary alcohol
Azacycle
Organoheterocyclic compound
Oxacycle
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Alcohol
Organic oxygen compound
Primary alcohol
Organic nitrogen compound
Organopnictogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

purine 2'-deoxyribonucleoside (CHEBI:28997 )

Ontology

Physiological effect

Health effect

Attachment loss (HMDB: HMDB0000071)
Periodontal Probing Depth (HMDB: HMDB0000071)

All tissues (HMDB: HMDB0000071)
All tissues (HMDB: HMDB0000071)

Tissue

All Tissues (HMDB: HMDB0000071)

Organ

Placenta (HMDB: HMDB0000071)

Excreta

Biofluid or Excreta

Urine (PMID: 8595732)
Feces (PMID: 27275383)

Non-excretory biofluid

Biofluid or Excreta

Blood (HMDB: HMDB0000071)
Saliva (PMID: 22308371)

Cellular substructure

Route of exposure

Enteral

Ingestion (HMDB: HMDB0000071)

Source

Endogenous

Endogenous (HMDB: HMDB0000071)

Plant

Fabaceae (HMDB: HMDB0000071)

Exogenous

Food

Food (HMDB: HMDB0000071)

Animal origin

Poultry

Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)
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)

Equine

Horse (FooDB: FOOD00378)

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)

Pulse

Bean

Yellow wax bean (FooDB: FOOD00882)
Green bean (FooDB: FOOD00883)

Pulses (FooDB: FOOD00867)

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Purine Metabolism (HMDB: HMDB0000071)
Purine Deoxyribonucleosides Degradation (PathBank: SMP0002089)

Azathioprine Action Pathway (HMDB: HMDB0000071)

Disease pathway

Adenosine Deaminase Deficiency (PathBank: SMP0000144)
Adenylosuccinate Lyase Deficiency (PathBank: SMP0000167)
Gout or Kelley-Seegmiller Syndrome (PathBank: SMP0000365)
Lesch-Nyhan Syndrome (LNS) (PathBank: SMP0000364)
Molybdenum Cofactor Deficiency (PathBank: SMP0000203)
Xanthine Dehydrogenase Deficiency (Xanthinuria) (PathBank: SMP0000220)
Purine Nucleoside Phosphorylase Deficiency (PathBank: SMP0000210)
AICA-Ribosiduria (PathBank: SMP0000168)
Xanthinuria Type I (PathBank: SMP0000512)
Xanthinuria Type II (PathBank: SMP0000513)
Adenine Phosphoribosyltransferase Deficiency (APRT) (PathBank: SMP0000535)
Mitochondrial DNA Depletion Syndrome (PathBank: SMP0000536)
Myoadenylate Deaminase Deficiency (PathBank: SMP0000537)
Mitochondrial DNA Depletion Syndrome (PathBank: SMP0120601)

Drug action pathway

Azathioprine Action Pathway (PathBank: SMP0000427)
Mercaptopurine Action Pathway (PathBank: SMP0000428)
Thioguanine Action Pathway (PathBank: SMP0000430)

Role

Industrial application

Pharmaceutical industry

Pharmaceutical (HMDB: HMDB0000071)

Biomarker

Eosinophilic esophagitis (MarkerDB: MDB00000037)
Purine nucleoside phosphorylase deficiency (MarkerDB: MDB00000037)

Biological role

human metabolite (HMDB: HMDB0000071)
Saccharomyces cerevisiae metabolite (HMDB: HMDB0000071)
plant metabolite (HMDB: HMDB0000071)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	250 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	-1.71	FORD,H ET AL. (1991)

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M-H]-	MetCCS_train_neg	153.399	30932474
[M+H]+	MetCCS_train_pos	151.712	30932474
[M-H]-	Not Available	153.399	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000097
[M+H]+	Not Available	151.928	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000097

Predicted Molecular Properties

Property	Value	Source
Water Solubility	18.7 g/L	ALOGPS
logP	-1.7	ALOGPS
logP	-0.66	ChemAxon
logS	-1.4	ALOGPS
pKa (Strongest Acidic)	11.68	ChemAxon
pKa (Strongest Basic)	-0.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	113.52 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	58.97 m³·mol⁻¹	ChemAxon
Polarizability	23.69 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]+	154.554	31661259
DarkChem	[M-H]-	154.009	31661259
AllCCS	[M+H]+	156.572	32859911
AllCCS	[M-H]-	156.243	32859911
DeepCCS	[M+H]+	149.735	30932474
DeepCCS	[M-H]-	147.339	30932474
DeepCCS	[M-2H]-	180.876	30932474
DeepCCS	[M+Na]+	155.647	30932474
AllCCS	[M+H]+	156.6	32859911
AllCCS	[M+H-H2O]+	152.9	32859911
AllCCS	[M+NH4]+	160.0	32859911
AllCCS	[M+Na]+	161.0	32859911
AllCCS	[M-H]-	156.2	32859911
AllCCS	[M+Na-2H]-	155.8	32859911
AllCCS	[M+HCOO]-	155.5	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Deoxyinosine	OC[C@H]1O[C@H](C[C@@H]1O)N1C=NC2=C1N=CNC2=O	3296.2	Standard polar	33892256
Deoxyinosine	OC[C@H]1O[C@H](C[C@@H]1O)N1C=NC2=C1N=CNC2=O	2352.6	Standard non polar	33892256
Deoxyinosine	OC[C@H]1O[C@H](C[C@@H]1O)N1C=NC2=C1N=CNC2=O	2765.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Deoxyinosine,1TMS,isomer #1	C[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC3=C2N=C[NH]C3=O)C[C@@H]1O	2444.3	Semi standard non polar	33892256
Deoxyinosine,1TMS,isomer #2	C[Si](C)(C)O[C@H]1C[C@H](N2C=NC3=C2N=C[NH]C3=O)O[C@@H]1CO	2465.2	Semi standard non polar	33892256
Deoxyinosine,1TMS,isomer #3	C[Si](C)(C)N1C=NC2=C(N=CN2[C@H]2C[C@H](O)[C@@H](CO)O2)C1=O	2550.0	Semi standard non polar	33892256
Deoxyinosine,2TMS,isomer #1	C[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC3=C2N=C[NH]C3=O)C[C@@H]1O[Si](C)(C)C	2397.8	Semi standard non polar	33892256
Deoxyinosine,2TMS,isomer #2	C[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC3=C2N=CN([Si](C)(C)C)C3=O)C[C@@H]1O	2509.6	Semi standard non polar	33892256
Deoxyinosine,2TMS,isomer #3	C[Si](C)(C)O[C@H]1C[C@H](N2C=NC3=C2N=CN([Si](C)(C)C)C3=O)O[C@@H]1CO	2521.1	Semi standard non polar	33892256
Deoxyinosine,3TMS,isomer #1	C[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC3=C2N=CN([Si](C)(C)C)C3=O)C[C@@H]1O[Si](C)(C)C	2507.8	Semi standard non polar	33892256
Deoxyinosine,3TMS,isomer #1	C[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC3=C2N=CN([Si](C)(C)C)C3=O)C[C@@H]1O[Si](C)(C)C	2766.2	Standard non polar	33892256
Deoxyinosine,3TMS,isomer #1	C[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC3=C2N=CN([Si](C)(C)C)C3=O)C[C@@H]1O[Si](C)(C)C	3283.4	Standard polar	33892256
Deoxyinosine,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC3=C2N=C[NH]C3=O)C[C@@H]1O	2677.5	Semi standard non polar	33892256
Deoxyinosine,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)O[C@H]1C[C@H](N2C=NC3=C2N=C[NH]C3=O)O[C@@H]1CO	2691.1	Semi standard non polar	33892256
Deoxyinosine,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N1C=NC2=C(N=CN2[C@H]2C[C@H](O)[C@@H](CO)O2)C1=O	2786.2	Semi standard non polar	33892256
Deoxyinosine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC3=C2N=C[NH]C3=O)C[C@@H]1O[Si](C)(C)C(C)(C)C	2846.0	Semi standard non polar	33892256
Deoxyinosine,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC3=C2N=CN([Si](C)(C)C(C)(C)C)C3=O)C[C@@H]1O	2958.6	Semi standard non polar	33892256
Deoxyinosine,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)O[C@H]1C[C@H](N2C=NC3=C2N=CN([Si](C)(C)C(C)(C)C)C3=O)O[C@@H]1CO	2970.6	Semi standard non polar	33892256
Deoxyinosine,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC3=C2N=CN([Si](C)(C)C(C)(C)C)C3=O)C[C@@H]1O[Si](C)(C)C(C)(C)C	3163.6	Semi standard non polar	33892256
Deoxyinosine,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC3=C2N=CN([Si](C)(C)C(C)(C)C)C3=O)C[C@@H]1O[Si](C)(C)C(C)(C)C	3408.6	Standard non polar	33892256
Deoxyinosine,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC3=C2N=CN([Si](C)(C)C(C)(C)C)C3=O)C[C@@H]1O[Si](C)(C)C(C)(C)C	3426.5	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Deoxyinosine GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-0udi-0933100000-09d719c947c60bf0f309	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Deoxyinosine GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-0zfr-0940000000-e72ee71b7bb48b638ddc	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Deoxyinosine GC-MS (3 TMS)	splash10-0zfr-2930000000-4781d246f6996b2513f8	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Deoxyinosine GC-EI-TOF (Non-derivatized)	splash10-0udi-0933100000-09d719c947c60bf0f309	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Deoxyinosine GC-EI-TOF (Non-derivatized)	splash10-0zfr-0940000000-e72ee71b7bb48b638ddc	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Deoxyinosine GC-MS (Non-derivatized)	splash10-0zfr-2930000000-4781d246f6996b2513f8	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Deoxyinosine GC-MS (Non-derivatized) - 70eV, Positive	splash10-059x-9460000000-45b38a8f7526df1e95a5	2016-09-22	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Deoxyinosine GC-MS (2 TMS) - 70eV, Positive	splash10-0v6u-8976000000-3868aac5f35f48870953	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Deoxyinosine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Deoxyinosine GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Deoxyinosine GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Deoxyinosine GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Deoxyinosine GC-MS (TMS_2_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Deoxyinosine GC-MS (TMS_2_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Deoxyinosine GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Deoxyinosine GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Deoxyinosine GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Deoxyinosine GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Deoxyinosine GC-MS (TBDMS_2_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Deoxyinosine GC-MS (TBDMS_2_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0f79-9300000000-1d2cd609ae1f49c1960f	2014-09-20	Not Available	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Deoxyinosine Quattro_QQQ 10V, Positive-QTOF (Annotated)	splash10-000i-0900000000-699f2e0add16852a454c	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Deoxyinosine Quattro_QQQ 25V, Positive-QTOF (Annotated)	splash10-000i-1900000000-ab78094925c0c212f113	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Deoxyinosine Quattro_QQQ 40V, Positive-QTOF (Annotated)	splash10-000i-5900000000-f14b9bd6e2a698307815	2012-07-24	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Deoxyinosine 10V, Positive-QTOF	splash10-000i-0920000000-a304c7b397cc865f33d1	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Deoxyinosine 20V, Positive-QTOF	splash10-000i-0900000000-984f375947cefdcfb884	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Deoxyinosine 40V, Positive-QTOF	splash10-01p9-0900000000-9bc9620b62695f652342	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Deoxyinosine 10V, Negative-QTOF	splash10-0udi-0290000000-5c34e254b55e1aa880cc	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Deoxyinosine 20V, Negative-QTOF	splash10-000i-0910000000-877252e0b2d402f920ab	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Deoxyinosine 40V, Negative-QTOF	splash10-052u-3900000000-d17c7ebc047d144462a1	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Deoxyinosine 10V, Negative-QTOF	splash10-0f79-0970000000-3ec5c5a89b8c9af39d7e	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Deoxyinosine 20V, Negative-QTOF	splash10-052r-0900000000-40c1b23e6815e6181307	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Deoxyinosine 40V, Negative-QTOF	splash10-0a5l-3900000000-9d7c6bf0280c77658451	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Deoxyinosine 10V, Positive-QTOF	splash10-000i-0900000000-b2e36fb98660834d7d24	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Deoxyinosine 20V, Positive-QTOF	splash10-000i-0900000000-f660b2a54215a2689fa2	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Deoxyinosine 40V, Positive-QTOF	splash10-000i-1900000000-4cf4a407cd370c6b4927	2021-09-24	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Experimental 1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	2012-12-04	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, 100 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, 200 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, 300 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, 400 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, 500 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, 600 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, 700 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, 800 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, 900 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
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Experimental 2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	2012-12-04	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular
Nucleus

Biospecimen Locations

Blood
Feces
Saliva
Urine

Tissue Locations

All Tissues
Placenta

Pathways

Name	SMPDB/PathBank	KEGG
Purine metabolism	Not Available
Adenosine Deaminase Deficiency		Not Available
Adenylosuccinate Lyase Deficiency		Not Available
Gout or Kelley-Seegmiller Syndrome		Not Available
Lesch-Nyhan Syndrome (LNS)		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Normal	Not Available	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	29808030	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	25037050	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	27543620	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	Zerihun T. Dame, ...	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Urine	Detected and Quantified	1.00 (0.00-2.00) umol/mmol creatinine	Adult (>18 years old)	Both	Normal	16613999	details
Urine	Detected and Quantified	< 0.1 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	8595732	details
Urine	Detected and Quantified	0-6 umol/mmol creatinine	Children (1 - 18 years old)	Both	Normal	BC Children's Hos...	details
Urine	Detected and Quantified	<0.1 umol/mmol creatinine	Infant (0-1 year old)	Both	Normal	30817767	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	25037050	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal Cancer	27275383	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	27015276	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Attachment loss	31026179	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Periodontal Probing Depth	31026179	details
Urine	Detected and Quantified	1.573 +/- 1.68 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Eosinophilic esophagitis	Analysis of 30 no...	details
Urine	Detected and Quantified	3.2 umol/mmol creatinine	Adult (>18 years old)	Both	Purine nucleoside phosphorylase (PNP) deficiency	8595732	details

Associated Disorders and Diseases

Disease References

Colorectal cancer
Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ] Sinha R, Ahn J, Sampson JN, Shi J, Yu G, Xiong X, Hayes RB, Goedert JJ: Fecal Microbiota, Fecal Metabolome, and Colorectal Cancer Interrelations. PLoS One. 2016 Mar 25;11(3):e0152126. doi: 10.1371/journal.pone.0152126. eCollection 2016. [PubMed:27015276 ] Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
Attachment loss
Liebsch C, Pitchika V, Pink C, Samietz S, Kastenmuller G, Artati A, Suhre K, Adamski J, Nauck M, Volzke H, Friedrich N, Kocher T, Holtfreter B, Pietzner M: The Saliva Metabolome in Association to Oral Health Status. J Dent Res. 2019 Jun;98(6):642-651. doi: 10.1177/0022034519842853. Epub 2019 Apr 26. [PubMed:31026179 ]
Periodontal Probing Depth
Liebsch C, Pitchika V, Pink C, Samietz S, Kastenmuller G, Artati A, Suhre K, Adamski J, Nauck M, Volzke H, Friedrich N, Kocher T, Holtfreter B, Pietzner M: The Saliva Metabolome in Association to Oral Health Status. J Dent Res. 2019 Jun;98(6):642-651. doi: 10.1177/0022034519842853. Epub 2019 Apr 26. [PubMed:31026179 ]
Purine nucleoside phosphorylase deficiency
Chantin C, Bonin B, Boulieu R, Bory C: Liquid-chromatographic study of purine metabolism abnormalities in purine nucleoside phosphorylase deficiency. Clin Chem. 1996 Feb;42(2):326-8. [PubMed:8595732 ]
Eosinophilic esophagitis
Slae, M., Huynh, H., Wishart, D.S. (2014). Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work). NA.

Associated OMIM IDs

114500 (Colorectal cancer)
164050 (Purine nucleoside phosphorylase deficiency )
610247 (Eosinophilic esophagitis)

External Links

DrugBank ID

DB02380

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB012323

KNApSAcK ID

Not Available

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Wikipedia Link

Not Available

METLIN ID

3383

PubChem Compound

65058

PDB ID

Not Available

ChEBI ID

28997

Food Biomarker Ontology

Not Available

VMH ID

DIN

MarkerDB ID

MDB00000037

Good Scents ID

Not Available

References

Synthesis Reference

Robins, Morris J.; Basom, Gerald L. Nucleic Acid Related Compounds. 8. Direct Conversion of 2′-Deoxyinosine to 6-Chloropurine 2′-Deoxyriboside and Selected 6-Substituted Deoxynucleosides and Their Evaluation As Substrates of Adenosine Deaminase. Canadian Journal of Chemistry, 1973, 51(19): 3161-3169, https://doi.org/10.1139/v73-471

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Cohen A, Doyle D, Martin DW Jr, Ammann AJ: Abnormal purine metabolism and purine overproduction in a patient deficient in purine nucleoside phosphorylase. N Engl J Med. 1976 Dec 23;295(26):1449-54. [PubMed:825775 ]
Kewn S, Hoggard PG, Henry-Mowatt JS, Veal GJ, Sales SD, Barry MG, Back DJ: Intracellular activation of 2',3'-dideoxyinosine and drug interactions in vitro. AIDS Res Hum Retroviruses. 1999 Jun 10;15(9):793-802. [PubMed:10381167 ]
Bemi V, Tazzni N, Banditelli S, Giorgelli F, Pesi R, Turchi G, Mattana A, Sgarrella F, Tozzi MG, Camici M: Deoxyadenosine metabolism in a human colon-carcinoma cell line (LoVo) in relation to its cytotoxic effect in combination with deoxycoformycin. Int J Cancer. 1998 Mar 2;75(5):713-20. [PubMed:9495239 ]
Chantin C, Bonin B, Boulieu R, Bory C: Liquid-chromatographic study of purine metabolism abnormalities in purine nucleoside phosphorylase deficiency. Clin Chem. 1996 Feb;42(2):326-8. [PubMed:8595732 ]
Ablett E, Pedley J, Dannoy PA, Sturm RA, Parsons PG: UVB-specific regulation of gene expression in human melanocytic cells: cell cycle effects and implication in the generation of melanoma. Mutat Res. 1998 Nov 9;422(1):31-41. [PubMed:9920426 ]
Bazar LS, Collier GB, Vanek PG, Siles BA, Kow YW, Doetsch PW, Cunningham RP, Chirikjian JG: Mutation identification DNA analysis system (MIDAS) for detection of known mutations. Electrophoresis. 1999 Jun;20(6):1141-8. [PubMed:10380753 ]
Sjoberg AH, Wang L, Eriksson S: Substrate specificity of human recombinant mitochondrial deoxyguanosine kinase with cytostatic and antiviral purine and pyrimidine analogs. Mol Pharmacol. 1998 Feb;53(2):270-3. [PubMed:9463485 ]
Brunk E, Sahoo S, Zielinski DC, Altunkaya A, Drager A, Mih N, Gatto F, Nilsson A, Preciat Gonzalez GA, Aurich MK, Prlic A, Sastry A, Danielsdottir AD, Heinken A, Noronha A, Rose PW, Burley SK, Fleming RMT, Nielsen J, Thiele I, Palsson BO: Recon3D enables a three-dimensional view of gene variation in human metabolism. Nat Biotechnol. 2018 Mar;36(3):272-281. doi: 10.1038/nbt.4072. Epub 2018 Feb 19. [PubMed:29457794 ]
Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]

Enzymes

Enzyme Details

1. Adenosine deaminase

General function:: Involved in deaminase activity
Specific function:: Catalyzes the hydrolytic deamination of adenosine and 2-deoxyadenosine. Plays an important role in purine metabolism and in adenosine homeostasis. Modulates signaling by extracellular adenosine, and so contributes indirectly to cellular signaling events. Acts as a positive regulator of T-cell coactivation, by binding DPP4. Its interaction with DPP4 regulates lymphocyte-epithelial cell adhesion.
Gene Name:: ADA
Uniprot ID:: P00813
Molecular weight:: 40764.13

Reactions

Deoxyadenosine + Water → Deoxyinosine + Ammonia	details

Enzyme Details

2. Purine nucleoside phosphorylase

General function:: Involved in purine-nucleoside phosphorylase activity
Specific function:: The purine nucleoside phosphorylases catalyze the phosphorolytic breakdown of the N-glycosidic bond in the beta-(deoxy)ribonucleoside molecules, with the formation of the corresponding free purine bases and pentose-1-phosphate.
Gene Name:: PNP
Uniprot ID:: P00491
Molecular weight:: 32117.69

Reactions

Deoxyinosine + Phosphate → Hypoxanthine + Deoxyribose 1-phosphate	details

Showing metabocard for Deoxyinosine (HMDB0000071)

MOL for HMDB0000071 (Deoxyinosine)

3D MOL for HMDB0000071 (Deoxyinosine)

3D SDF for HMDB0000071 (Deoxyinosine)

3D-SDF for HMDB0000071 (Deoxyinosine)

PDB for HMDB0000071 (Deoxyinosine)

3D PDB for HMDB0000071 (Deoxyinosine)

SMILES for HMDB0000071 (Deoxyinosine)

INCHI for HMDB0000071 (Deoxyinosine)

Structure for HMDB0000071 (Deoxyinosine)

3D Structure for HMDB0000071 (Deoxyinosine)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes

Reactions

Reactions