NP-MRD: Showing NP-Card for Deoxyinosine (NP0000903)

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Record Information

Version

1.0

Created at

2005-11-16 15:48:42 UTC

Updated at

2021-10-07 20:38:43 UTC

NP-MRD ID

NP0000903

Secondary Accession Numbers

None

Natural Product 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>
NP0000903

> <DATABASE_NAME>
NP-MRD

> <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

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 Mass

252.2300 Da

Monoisotopic Mass

252.08585 Da

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

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Anas platyrhynchos	FooDB	FooDB
Anatidae	FooDB	FooDB
Anser anser	FooDB	FooDB
Asterias forbesi	LOTUS Database	35616633
Bison bison	FooDB	FooDB
Bos taurus	FooDB	FooDB
Bos taurus X Bison bison	FooDB	FooDB
Bubalus bubalis	FooDB	FooDB
Capra aegagrus hircus	FooDB	FooDB
Cervidae	FooDB	FooDB
Cervus canadensis	FooDB	FooDB
Columba	FooDB	FooDB
Columbidae	FooDB	FooDB
Dromaius novaehollandiae	FooDB	FooDB
Equus caballus	FooDB	FooDB
Gallus gallus	FooDB	FooDB
Homo sapiens	LOTUS Database	35616633
Lagopus muta	FooDB	FooDB
Leporidae	FooDB	FooDB
Lepus timidus	FooDB	FooDB
Melanitta fusca	FooDB	FooDB
Meleagris gallopavo	FooDB	FooDB
Mus musculus	LOTUS Database	35616633
Numida meleagris	FooDB	FooDB
Odocoileus	FooDB	FooDB
Oryctolagus	FooDB	FooDB
Ovis aries	FooDB	FooDB
Phaseolus vulgaris	KNApSAcK Database	22123792
Phasianidae	FooDB	FooDB
Phasianus colchicus	FooDB	FooDB
Struthio camelus	FooDB	FooDB
Sus scrofa	FooDB	FooDB
Sus scrofa domestica	FooDB	FooDB

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 )

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	250 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	32500 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	-1.71	Barchi Jr, J. J., Marquez, V. E., Driscoll, J. S., Ford Jr, H., Mitsuya, H., Shirasaka, T., Aoki, S., & Kelley, J. A. (1991). Potential anti-AIDS drugs. Lipophilic, adenosine deaminase-activated prodrugs. Journal of medicinal chemistry, 34(5), 1647-1655.

Predicted 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

External Links

HMDB ID

HMDB0000071

DrugBank ID

DB02380

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

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

Good Scents ID

rw1136451

References

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 ]

Showing NP-Card for Deoxyinosine (NP0000903)

MOL for NP0000903 (Deoxyinosine)

3D MOL for NP0000903 (Deoxyinosine)

3D SDF for NP0000903 (Deoxyinosine)

3D-SDF for NP0000903 (Deoxyinosine)

PDB for NP0000903 (Deoxyinosine)

3D PDB for NP0000903 (Deoxyinosine)

SMILES for NP0000903 (Deoxyinosine)

INCHI for NP0000903 (Deoxyinosine)

Structure for NP0000903 (Deoxyinosine)

3D Structure for NP0000903 (Deoxyinosine)