MiMeDB: Showing metabocard for Inosine (MMDBc0000064)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2020-10-27 23:29:04 UTC

Update Date

2022-08-30 23:28:57 UTC

Metabolite ID

MMDBc0000064

Metabolite Identification

Common Name

Inosine

Description

Inosine, also known as hypoxanthosine or inotin, belongs to the class of organic compounds known as purine nucleosides. Purine nucleosides are compounds comprising a purine base attached to a ribosyl or deoxyribosyl moiety. Inosine is a moderately basic compound (based on its pKa). Inosine exists in all living species, ranging from bacteria to humans. Within humans, inosine participates in a number of enzymatic reactions. In particular, inosine can be biosynthesized from inosinic acid through its interaction with the enzyme cytosolic purine 5'-nucleotidase. In addition, inosine can be converted into hypoxanthine and ribose 1-phosphate through its interaction with the enzyme purine nucleoside phosphorylase. Inosine, with regard to humans, has been found to be associated with several diseases such as ulcerative colitis, degenerative disc disease, kidney disease, and gout. Inosine is a purine nucleoside that has hypoxanthine linked by the N9 nitrogen to the C1 carbon of ribose. It is an intermediate in the degradation of purines and purine nucleosides to uric acid and in pathways of purine salvage. It also occurs in the anticodon of certain transfer RNA molecules (Dorland, 28th ed). Inosine is found to be associated with purine nucleoside phosphorylase deficiency and xanthinuria type I, which are inborn errors of metabolism.

Structure

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

HMDB0000195
     RDKit          3D
Inosine
 31 33  0  0  0  0  0  0  0  0999 V2000
   -3.4275    2.5315    0.2045 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1924    2.1387   -0.2975 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1259    0.6528   -0.5773 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8648    0.3781   -1.0680 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5313   -0.9083   -0.7157 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8852   -1.0074   -0.4428 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5549   -2.1305   -0.2225 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8492   -1.8611   -0.0037 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9676   -0.5195   -0.0953 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1007    0.2749    0.0490 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3308   -0.3046    0.3278 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9250    1.5935   -0.0956 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7145    2.1391   -0.3679 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6353    1.3532   -0.5029 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7492    0.0353   -0.3699 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3335   -1.2996    0.4820 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9928   -2.5092    0.2042 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3461   -0.1874    0.6399 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.6334   -0.7371    0.6057 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8060    1.7628    0.7031 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3944    2.3904    0.4223 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9686    2.6455   -1.2690 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8782    0.3799   -1.3564 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7575   -1.5702   -1.5805 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1011   -3.1166   -0.2237 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1789   -0.0181   -0.1460 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6388    3.2228   -0.4740 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7308   -1.3862    1.4036 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8060   -2.8070   -0.7214 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1860    0.3694    1.5874 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6558   -1.5053    0.0063 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 10 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
  5 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 18  3  1  0
 15  6  1  0
 15  9  1  0
  1 20  1  0
  2 21  1  0
  2 22  1  0
  3 23  1  6
  5 24  1  6
  7 25  1  0
 11 26  1  0
 13 27  1  0
 16 28  1  1
 17 29  1  0
 18 30  1  1
 19 31  1  0
M  END


  Mrv1652309032023562D          

 19 21  0  0  1  0            999 V2000
   -0.2169    0.6674    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5678    0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7018    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2169   -0.6674    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2352    0.8974    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2352   -0.8974    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4718   -1.4521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0801   -2.0652    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0131    2.1195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4718    1.4521    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2564    1.7070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2564    2.5320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6854    1.7070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4718    2.7869    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9709    2.9445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9709    3.7695    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6854    2.5320    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9709    1.2945    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1 11  1  1  0  0  0
  2  1  1  0  0  0  0
  2  6  1  6  0  0  0
  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
  4  7  1  6  0  0  0
  3  5  1  0  0  0  0
  5  4  1  0  0  0  0
  5  8  1  1  0  0  0
  8  9  1  0  0  0  0
 10 11  1  0  0  0  0
 10 15  2  0  0  0  0
 12 11  1  0  0  0  0
 19 12  2  0  0  0  0
 12 13  1  0  0  0  0
 15 13  1  0  0  0  0
 13 16  2  0  0  0  0
 18 14  2  0  0  0  0
 14 19  1  0  0  0  0
 18 16  1  0  0  0  0
 16 17  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0000064

> <DATABASE_NAME>
MIME

> <SMILES>
OC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=NC2=C(O)N=CN=C12

> <INCHI_IDENTIFIER>
InChI=1S/C10H12N4O5/c15-1-4-6(16)7(17)10(19-4)14-3-13-5-8(14)11-2-12-9(5)18/h2-4,6-7,10,15-17H,1H2,(H,11,12,18)/t4-,6-,7-,10-/m1/s1

> <INCHI_KEY>
UGQMRVRMYYASKQ-KQYNXXCUSA-N

> <FORMULA>
C10H12N4O5

> <MOLECULAR_WEIGHT>
268.2261

> <EXACT_MASS>
268.080769514

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
31

> <JCHEM_AVERAGE_POLARIZABILITY>
24.603674083841288

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-6,9-dihydro-3H-purin-6-one

> <JCHEM_LOGP>
-1.9609272363333337

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.456472643760424

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.941792414582618

> <JCHEM_PKA_STRONGEST_BASIC>
2.7357381933005236

> <JCHEM_POLAR_SURFACE_AREA>
129.20000000000002

> <JCHEM_REFRACTIVITY>
60.898399999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
inosine

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0000195
     RDKit          3D
Inosine
 31 33  0  0  0  0  0  0  0  0999 V2000
   -3.4275    2.5315    0.2045 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1924    2.1387   -0.2975 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1259    0.6528   -0.5773 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8648    0.3781   -1.0680 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5313   -0.9083   -0.7157 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8852   -1.0074   -0.4428 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5549   -2.1305   -0.2225 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8492   -1.8611   -0.0037 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9676   -0.5195   -0.0953 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1007    0.2749    0.0490 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3308   -0.3046    0.3278 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9250    1.5935   -0.0956 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7145    2.1391   -0.3679 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6353    1.3532   -0.5029 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7492    0.0353   -0.3699 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3335   -1.2996    0.4820 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9928   -2.5092    0.2042 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3461   -0.1874    0.6399 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.6334   -0.7371    0.6057 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8060    1.7628    0.7031 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3944    2.3904    0.4223 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9686    2.6455   -1.2690 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8782    0.3799   -1.3564 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7575   -1.5702   -1.5805 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1011   -3.1166   -0.2237 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1789   -0.0181   -0.1460 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6388    3.2228   -0.4740 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7308   -1.3862    1.4036 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8060   -2.8070   -0.7214 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1860    0.3694    1.5874 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6558   -1.5053    0.0063 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 10 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
  5 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 18  3  1  0
 15  6  1  0
 15  9  1  0
  1 20  1  0
  2 21  1  0
  2 22  1  0
  3 23  1  6
  5 24  1  6
  7 25  1  0
 11 26  1  0
 13 27  1  0
 16 28  1  1
 17 29  1  0
 18 30  1  1
 19 31  1  0
M  END

HEADER    PROTEIN                                 03-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-SEP-20         0                                  
HETATM    1  C   UNK     0      -0.405   1.246   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.060   0.770   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -1.310   0.000   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       1.060  -0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.405  -1.246   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       2.306   1.675   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0       2.306  -1.675   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -0.881  -2.711   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       0.150  -3.855   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       0.024   3.956   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0      -0.881   2.711   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0      -2.345   3.186   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.345   4.726   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -5.013   3.186   0.000  0.00  0.00           C+0
HETATM   15  N   UNK     0      -0.881   5.202   0.000  0.00  0.00           N+0
HETATM   16  C   UNK     0      -3.679   5.496   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -3.679   7.036   0.000  0.00  0.00           O+0
HETATM   18  N   UNK     0      -5.013   4.726   0.000  0.00  0.00           N+0
HETATM   19  N   UNK     0      -3.679   2.416   0.000  0.00  0.00           N+0
CONECT    1   11    2    3                                                  
CONECT    2    1    6    4                                                  
CONECT    3    1    5                                                       
CONECT    4    2    7    5                                                  
CONECT    5    3    4    8                                                  
CONECT    6    2                                                            
CONECT    7    4                                                            
CONECT    8    5    9                                                       
CONECT    9    8                                                            
CONECT   10   11   15                                                       
CONECT   11    1   10   12                                                  
CONECT   12   11   19   13                                                  
CONECT   13   12   15   16                                                  
CONECT   14   18   19                                                       
CONECT   15   10   13                                                       
CONECT   16   13   18   17                                                  
CONECT   17   16                                                            
CONECT   18   14   16                                                       
CONECT   19   12   14                                                       
MASTER        0    0    0    0    0    0    0    0   19    0   42    0
END

COMPND    HMDB0000195
HETATM    1  O1  UNL     1      -3.428   2.531   0.204  1.00  0.00           O  
HETATM    2  C1  UNL     1      -2.192   2.139  -0.297  1.00  0.00           C  
HETATM    3  C2  UNL     1      -2.126   0.653  -0.577  1.00  0.00           C  
HETATM    4  O2  UNL     1      -0.865   0.378  -1.068  1.00  0.00           O  
HETATM    5  C3  UNL     1      -0.531  -0.908  -0.716  1.00  0.00           C  
HETATM    6  N1  UNL     1       0.885  -1.007  -0.443  1.00  0.00           N  
HETATM    7  C4  UNL     1       1.555  -2.130  -0.223  1.00  0.00           C  
HETATM    8  N2  UNL     1       2.849  -1.861  -0.004  1.00  0.00           N  
HETATM    9  C5  UNL     1       2.968  -0.520  -0.095  1.00  0.00           C  
HETATM   10  C6  UNL     1       4.101   0.275   0.049  1.00  0.00           C  
HETATM   11  O3  UNL     1       5.331  -0.305   0.328  1.00  0.00           O  
HETATM   12  N3  UNL     1       3.925   1.594  -0.096  1.00  0.00           N  
HETATM   13  C7  UNL     1       2.715   2.139  -0.368  1.00  0.00           C  
HETATM   14  N4  UNL     1       1.635   1.353  -0.503  1.00  0.00           N  
HETATM   15  C8  UNL     1       1.749   0.035  -0.370  1.00  0.00           C  
HETATM   16  C9  UNL     1      -1.334  -1.300   0.482  1.00  0.00           C  
HETATM   17  O4  UNL     1      -1.993  -2.509   0.204  1.00  0.00           O  
HETATM   18  C10 UNL     1      -2.346  -0.187   0.640  1.00  0.00           C  
HETATM   19  O5  UNL     1      -3.633  -0.737   0.606  1.00  0.00           O  
HETATM   20  H1  UNL     1      -3.806   1.763   0.703  1.00  0.00           H  
HETATM   21  H2  UNL     1      -1.394   2.390   0.422  1.00  0.00           H  
HETATM   22  H3  UNL     1      -1.969   2.646  -1.269  1.00  0.00           H  
HETATM   23  H4  UNL     1      -2.878   0.380  -1.356  1.00  0.00           H  
HETATM   24  H5  UNL     1      -0.758  -1.570  -1.580  1.00  0.00           H  
HETATM   25  H6  UNL     1       1.101  -3.117  -0.224  1.00  0.00           H  
HETATM   26  H7  UNL     1       6.179  -0.018  -0.146  1.00  0.00           H  
HETATM   27  H8  UNL     1       2.639   3.223  -0.474  1.00  0.00           H  
HETATM   28  H9  UNL     1      -0.731  -1.386   1.404  1.00  0.00           H  
HETATM   29  H10 UNL     1      -1.806  -2.807  -0.721  1.00  0.00           H  
HETATM   30  H11 UNL     1      -2.186   0.369   1.587  1.00  0.00           H  
HETATM   31  H12 UNL     1      -3.656  -1.505   0.006  1.00  0.00           H  
CONECT    1    2   20
CONECT    2    3   21   22
CONECT    3    4   18   23
CONECT    4    5
CONECT    5    6   16   24
CONECT    6    7   15
CONECT    7    8    8   25
CONECT    8    9
CONECT    9   10   10   15
CONECT   10   11   12
CONECT   11   26
CONECT   12   13   13
CONECT   13   14   27
CONECT   14   15   15
CONECT   16   17   18   28
CONECT   17   29
CONECT   18   19   30
CONECT   19   31
END

HMDB0000195
     RDKit          3D
Inosine
 31 33  0  0  0  0  0  0  0  0999 V2000
   -3.4275    2.5315    0.2045 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1924    2.1387   -0.2975 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1259    0.6528   -0.5773 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8648    0.3781   -1.0680 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5313   -0.9083   -0.7157 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8852   -1.0074   -0.4428 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5549   -2.1305   -0.2225 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8492   -1.8611   -0.0037 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9676   -0.5195   -0.0953 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1007    0.2749    0.0490 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3308   -0.3046    0.3278 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9250    1.5935   -0.0956 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7145    2.1391   -0.3679 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6353    1.3532   -0.5029 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7492    0.0353   -0.3699 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3335   -1.2996    0.4820 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9928   -2.5092    0.2042 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3461   -0.1874    0.6399 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.6334   -0.7371    0.6057 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8060    1.7628    0.7031 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3944    2.3904    0.4223 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9686    2.6455   -1.2690 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8782    0.3799   -1.3564 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7575   -1.5702   -1.5805 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1011   -3.1166   -0.2237 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1789   -0.0181   -0.1460 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6388    3.2228   -0.4740 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7308   -1.3862    1.4036 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8060   -2.8070   -0.7214 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1860    0.3694    1.5874 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6558   -1.5053    0.0063 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 10 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
  5 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 18  3  1  0
 15  6  1  0
 15  9  1  0
  1 20  1  0
  2 21  1  0
  2 22  1  0
  3 23  1  6
  5 24  1  6
  7 25  1  0
 11 26  1  0
 13 27  1  0
 16 28  1  1
 17 29  1  0
 18 30  1  1
 19 31  1  0
M  END

Synonyms

Value	Source
9-beta-D-Ribofuranosyl-9H-purin-6-ol	ChEBI
9-beta-D-Ribofuranosylhypoxanthine	ChEBI
Hypoxanthine D-riboside	ChEBI
Hypoxanthosine	ChEBI
i	ChEBI
Inosin	ChEBI
Inosina	ChEBI
Inosinum	ChEBI
Inotin	Kegg
9-b-D-Ribofuranosyl-9H-purin-6-ol	Generator
9-Β-D-ribofuranosyl-9H-purin-6-ol	Generator
9-b-D-Ribofuranosylhypoxanthine	Generator
9-Β-D-ribofuranosylhypoxanthine	Generator
(-)-Inosine	HMDB
1,9-Dihydro-9-b-D-ribofuranosyl-6H-purin-6-one	HMDB
1,9-Dihydro-9-beta-D-ribofuranosyl-6H-purin-6-one	HMDB
1,9-Dihydro-9-beta-delta-ribofuranosyl-6H-purin-6-one	HMDB
9-b-D-Ribofuranosyl-hypoxanthine	HMDB
9-beta-D-Ribofuranosyl-hypoxanthine	HMDB
9-beta-delta-Ribofuranosyl-hypoxanthine	HMDB
9-beta-delta-Ribofuranosylhypoxanthine	HMDB
9beta-D-Ribofuranosylhypoxanthine	HMDB
9beta-delta-Ribofuranosylhypoxanthine	HMDB
Atorel	HMDB
beta-D-Ribofuranoside hypoxanthine-9	HMDB
beta-delta-Ribofuranoside hypoxanthine-9	HMDB
beta-Inosine	HMDB
HXR	HMDB
Hypoxanthine 9-beta-D-ribofuranoside	HMDB
Hypoxanthine 9-beta-delta-ribofuranoside	HMDB
Hypoxanthine nucleoside	HMDB
Hypoxanthine ribonucleoside	HMDB
Hypoxanthine riboside	HMDB
Hypoxanthine-9 beta-D-ribofuranoside	HMDB
Hypoxanthine-9 beta-delta-ribofuranoside	HMDB
Hypoxanthine-9-beta-D-ribofuranoside	HMDB
Hypoxanthine-9-beta-delta-ribofuranoside	HMDB
Hypoxanthine-9-D-ribofuranoside	HMDB
Hypoxanthine-9-delta-ribofuranoside	HMDB
Hypoxanthine-ribose	HMDB
Indole-3-carboxaldehyde	HMDB
Ino	HMDB
Inosie	HMDB
Iso-prinosine	HMDB
Oxiamin	HMDB
Panholic-L	HMDB
Pantholic-L	HMDB
Ribonosine	HMDB
Selfer	HMDB
Trophicardyl	HMDB

Molecular Formula

C₁₀H₁₂N₄O₅

Average Mass

268.2261

Monoisotopic Mass

268.080769514

IUPAC Name

9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-6,9-dihydro-3H-purin-6-one

Traditional Name

inosine

CAS Registry Number

58-63-9

SMILES

OC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=NC2=C(O)N=CN=C12

InChI Identifier

InChI=1S/C10H12N4O5/c15-1-4-6(16)7(17)10(19-4)14-3-13-5-8(14)11-2-12-9(5)18/h2-4,6-7,10,15-17H,1H2,(H,11,12,18)/t4-,6-,7-,10-/m1/s1

InChI Key

UGQMRVRMYYASKQ-KQYNXXCUSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as purine nucleosides. Purine nucleosides are compounds comprising a purine base attached to a ribosyl or deoxyribosyl moiety.

Kingdom

Organic compounds

Super Class

Nucleosides, nucleotides, and analogues

Class

Purine nucleosides

Sub Class

Not Available

Direct Parent

Purine nucleosides

Alternative Parents

Substituents

Purine nucleoside
Glycosyl compound
N-glycosyl compound
6-oxopurine
Hypoxanthine
Pentose monosaccharide
Purinone
Imidazopyrimidine
Purine
Pyrimidone
Pyrimidine
Monosaccharide
N-substituted imidazole
Vinylogous amide
Tetrahydrofuran
Heteroaromatic compound
Azole
Imidazole
Secondary alcohol
Oxacycle
Azacycle
Organoheterocyclic compound
Alcohol
Organonitrogen compound
Organic nitrogen compound
Organooxygen compound
Organic oxide
Organopnictogen compound
Organic oxygen compound
Hydrocarbon derivative
Primary alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

inosines (CHEBI:17596 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
logP	-2	ChemAxon
pKa (Strongest Acidic)	6.94	ChemAxon
pKa (Strongest Basic)	2.74	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	60.9 m³·mol⁻¹	ChemAxon
Polarizability	24.6 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

Spectra

Chromatographic Retention Times and Retention Indices

Retention Times

Not Available

Retention Indices

Not Available

Chromatographic Retention Times and Retention Indices

Retention Times

Not Available

Retention Indices

Not Available

Biological Properties

Cellular Locations

Cytoplasm
Extracellular
Lysosome
Mitochondria

Biospecimen Locations

Blood
Brain
Cellular Cytoplasm
Cerebrospinal Fluid (CSF)
Erythrocyte
Feces
Fibroblasts
Intestine
Kidney
Liver
Neuron
Pancreas
Pericardial Effusion
Placenta
Platelet
Prostate
Saliva
Spleen
Testis
Urine

Tissue Locations

Brain
Erythrocyte
Fibroblasts
Intestine
Kidney
Liver
Neuron
Pancreas
Placenta
Platelet
Prostate
Spleen
Testis

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species
MMDBp0191677	5'-nucleotidase	Unknown	P21589	Homo_sapiens
MMDBp0191680	Cytosolic 5'-nucleotidase 1B	Unknown	Q96P26	Homo_sapiens
MMDBp0191681	Cytosolic 5'-nucleotidase 1A	Unknown	Q9BXI3	Homo_sapiens
MMDBp0191682	5'(3')-deoxyribonucleotidase, cytosolic type	Unknown	Q8TCD5	Homo_sapiens
MMDBp0191684	5'(3')-deoxyribonucleotidase, mitochondrial	Unknown	Q9NPB1	Homo_sapiens
MMDBp0191852	Xanthine dehydrogenase/oxidase	Unknown	P47989	Homo_sapiens
MMDBp0192304	Adenosine deaminase	Enzyme	P00813	Homo_sapiens
MMDBp0193629	Equilibrative nucleoside transporter 4	Unknown	Q7RTT9	Homo_sapiens
MMDBp0193860	Cytosolic 5'-nucleotidase 3	Enzyme	Q9H0P0	Homo_sapiens
MMDBp0193932	Cytosolic purine 5'-nucleotidase	Unknown	P49902	Homo_sapiens
MMDBp0193933	Purine nucleoside phosphorylase	Enzyme	P00491	Homo_sapiens
MMDBp0196393	tRNA-specific adenosine deaminase 1	Unknown	Q9BUB4	Homo_sapiens
MMDBp0196704	Adenosine deaminase CECR1	Unknown	Q9NZK5

Human Pathways

Pathways

Name	SMPDB/PathBank

Microbial Pathways

Pathways

Not Available

Metabolic Reactions

Reactions

This table shows at most 20 reactions. For the full list of associated reactions:

See All Associated Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference
Canavan disease		Association	Human Blood	HMDB	16139832
Canavan disease	Slight Decrease	Association	Human Urine	HMDB	16139832
Coronary artery disease	Slight Increase	Association	Human Pericardial Effusion	HMDB	10499868
Critical illnesses	Decreased	Association	Human Blood	HMDB	9663253
Degenerative disc disease		Association	Human Cerebrospinal Fluid (CSF)	HMDB	6656991
Kidney disease		Association	Human Blood	HMDB	9607216
Purine nucleoside phosphorylase deficiency	Increased	Association	Human Blood	HMDB	8595732
Purine nucleoside phosphorylase deficiency	Increased	Association	Human Urine	HMDB	8595732
Septic shock		Association	Human Blood	HMDB	9663253
Eosinophilic esophagitis		Association	Human Urine	HMDB	Slae, M., Huynh, H., Wishart, D.S. (2014). Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work)

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Firmicutes	540	Human feces; Human pleural fluid plaque; Pig ; Human ; Cattle	Microbial culture; Metabolic reconstruction
Eukaryota	Apicomplexa	1		Microbial culture
Bacteria	Bacteroidetes	242	Human feces; Human appendix biopsy; Human	Microbial culture; Metabolic reconstruction
Bacteria	Proteobacteria	451	Human feces; Human sputum; Human ; Human unknown; Pig ; Human pleural fluid plaque; Human dental plaque; Human nasal swab; Human feces; pleural fluid plaque; bal; River trout ; Cattle	Indirect association between microbiota composition and metabolites measured in host biospecimen; Metabolic reconstruction
Bacteria	Actinobacteria	170	Human feces; Human sputum; Human bronchial brush; Human nasopharyngeal swab; Human pleural fluid plaque; Human dental plaque; Human ; Cattle	Metabolic reconstruction
Bacteria	Verrucomicrobia	2	Human ; Human feces	Metabolic reconstruction
Bacteria	Synergistetes	5	Human feces	Metabolic reconstruction
Bacteria	Spirochaetes	6	Human feces; Human	Metabolic reconstruction
Archaea	Thaumarchaeota	1	Human feces	Metabolic reconstruction
Bacteria	Fusobacteria	24	Human feces; Human	Metabolic reconstruction
Archaea	Euryarchaeota	5	Human feces; Cattle ; Human	Metabolic reconstruction
Bacteria	Candidatus Melainabacteria	2	Human feces	Metabolic reconstruction
Bacteria	Tenericutes	4	Human feces	Metabolic reconstruction
Bacteria	Planctomycetes	2	Human feces	Metabolic reconstruction
Archaea	Crenarchaeota	1	Human feces	Metabolic reconstruction
Archaea/Archaea	Euryarchaeota	17	Human feces; Cattle ; Human	Metabolic reconstruction
Bacteria	Aquificae	1
Bacteria	Deinococcus-Thermus	1
Bacteria	nah	1
Bacteria/NULL	nah	1
Bacteria	Chlorobi	1
Bacteria/NULL	Proteobacteria	1	Human feces; Human sputum; Human ; Human unknown; Pig ; Human pleural fluid plaque; Human dental plaque; Human nasal swab; Human feces; pleural fluid plaque; bal; River trout ; Cattle	Indirect association between microbiota composition and metabolites measured in host biospecimen; Metabolic reconstruction
Eukaryota/Fungi	Ascomycota	13	Human feces	Unknown

Exposure Sources

Other Exposures

Source Type	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Age	Sex	Health Condition	Data Source	Reference
Human Feces	Detected but not Quantified								HMDB
Human	Detected and Quantified	0.68	0.47			Adult (>18 years old)	Both	Canavan disease	HMDB	16139832
Human	Detected and Quantified	1.00	1.61			Adult (>18 years old)	Both	Canavan disease	HMDB	16139832
Human	Detected and Quantified	0.658		0.321	1.331	Adult (>18 years old)	Both	Coronary artery disease	HMDB	10499868
Human	Detected and Quantified	0.19	0.17			Adult (>18 years old)	Both	Major trauma	HMDB	9663253
Human	Detected and Quantified	0.70		0.60	0.80	Adult (>18 years old)	Both	Degenerative disc disease	HMDB	6656991
Human	Detected and Quantified	1.6	0.4			Adult (>18 years old)	Both	Kidney disease	HMDB	9607216
Human	Detected and Quantified	30				Adult (>18 years old)	Both	Purine nucleoside phosphorylase deficiency	HMDB	8595732
Human	Detected and Quantified	14000				Adult (>18 years old)	Both	Purine nucleoside phosphorylase deficiency	HMDB	8595732
Human	Detected and Quantified	0.19	0.17 uM			Adult (>18 years old)	Both	Septic shock	HMDB	9663253
Human	Detected and Quantified	1.0	0.5			Adult (>18 years old)	Both	Solid tumors	HMDB	6736109
Human	Detected and Quantified	0.5				Children (1-13 years old)	Male	Xanthinuria type 1	HMDB	3818951
Human	Detected and Quantified	0.6				Adult (>18 years old)	Female	Xanthinuria type 1	HMDB	3818951
Human	Detected and Quantified	0.5				Infant (0-1 year old)	Both	Normal	HMDB	30817767
Human	Detected and Quantified	1				Adult (>18 years old)	Both	Normal	HMDB	15882454
Human	Detected and Quantified			0	25	Newborn (0-30 days old)	Both	Normal	HMDB	31506554
Human	Detected and Quantified	0.05	0.01			Adult (>18 years old)	Both	Normal	HMDB	9663253
Human	Detected and Quantified	0.20	0.07			Adult (>18 years old)	Both	Normal	HMDB	16139832
Human	Detected and Quantified	0.28	0.15			Adult (>18 years old)	Female	Normal	HMDB	9129323
Human	Detected and Quantified	0.28	0.33			Adolescent (13-18 years old)	Both	Normal	HMDB	16139832
Human	Detected and Quantified	0.3	0.1			Adult (>18 years old)	Both	Normal	HMDB	8595732
Human	Detected and Quantified	0.30	0.16			Adult (>18 years old)	Both	Normal	HMDB	9129323
Human	Detected and Quantified	0.31	0.17			Adult (>18 years old)	Male	Normal	HMDB	9129323
Human	Detected and Quantified	0.347		0.159	1.037	Adult (>18 years old)	Both	Normal	HMDB	10499868
Human	Detected and Quantified	0.6		0.0	1.2	Newborn (0-30 days old)	Both	Normal	HMDB	6681617
Human	Detected and Quantified	0.64	0.35			Adult (>18 years old)	Both	Normal	HMDB	8597780
Human	Detected and Quantified	0.68	0.20			Adult (>18 years old)	Both	Normal	HMDB	11310987
Human	Detected and Quantified	0.71	0.89			Children (1-13 years old)	Both	Normal	HMDB	16139832
Human	Detected and Quantified	0.73	0.16			Adult (>18 years old)	Both	Normal	HMDB	11310987
Human	Detected and Quantified	0.9	0.2			Adult (>18 years old)	Male	normal	HMDB	3818951
Human	Detected and Quantified	0.96	0.23			Adult (>18 years old)	Both	Normal	HMDB	11310987
Human	Detected and Quantified	1.04	0.56			Adult (>18 years old)	Both	Normal	HMDB	16139832
Human	Detected and Quantified	1.4		0.4	6.5	Adult (>18 years old)	Both	Normal	HMDB	24023812
Human	Detected and Quantified	5.0	0.8			Adult (>18 years old)	Both	Normal	HMDB	9607216
Human	Detected and Quantified	2.388	2.543			Children (1 - 13 years old)	Not Specified	Eosinophilic esophagitis	HMDB	Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work)
Human	Detected and Quantified	1.653				Children (1 - 13 years old)	Not Specified	Normal	HMDB	Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work)
Human	Detected and Quantified			0	21	Children (1 - 18 years old)	Both	Normal	HMDB	BC Children's Hospital Biochemical Genetics Lab
Human	Detected and Quantified	0.37	0.80			Adult (>18 years old)	Both	Normal	HMDB	https://doi.org/10.1007/s11306-015-0840-5
Human Brain	Detected but not Quantified					Not Specified	Not Specified	Normal	HMDB	34986597
Human Erythrocyte	Detected but not Quantified					Not Specified	Not Specified	Normal	HMDB	34986597
Human Fibroblasts	Detected but not Quantified					Not Specified	Not Specified	Normal	HMDB	34986597
Human Intestine	Detected but not Quantified					Not Specified	Not Specified	Normal	HMDB	34986597
Human Kidney	Detected but not Quantified					Not Specified	Not Specified	Normal	HMDB	34986597
Human Liver	Detected but not Quantified					Not Specified	Not Specified	Normal	HMDB	34986597
Human Neuron	Detected but not Quantified					Not Specified	Not Specified	Normal	HMDB	34986597
Human Pancreas	Detected but not Quantified					Not Specified	Not Specified	Normal	HMDB	34986597
Human Placenta	Detected but not Quantified					Not Specified	Not Specified	Normal	HMDB	34986597
Human Platelet	Detected but not Quantified					Not Specified	Not Specified	Normal	HMDB	34986597
Human Prostate	Detected but not Quantified					Not Specified	Not Specified	Normal	HMDB	34986597
Human Spleen	Detected but not Quantified					Not Specified	Not Specified	Normal	HMDB	34986597
Human Testis	Detected but not Quantified					Not Specified	Not Specified	Normal	HMDB	34986597
Human Feces	Detected but not Quantified					Adult (>18 years old)	Both	Normal	HMDB	21330412
Human Feces	Detected but not Quantified					Children (6 - 18 years old)	Not Specified	Normal	HMDB	27609529
Human Feces	Detected but not Quantified					Adult (>18 years old)	Male	Normal	HMDB	28270806
Human Feces	Detected but not Quantified					Adult (>18 years old)	Both	Normal	HMDB	27543620
Human Feces	Detected but not Quantified					Adult (>18 years old)	Both	Normal	HMDB	25037050
Human Feces	Detected but not Quantified					Adult (>18 years old)	Both	Normal	HMDB	29808030
Human Urine	Detected but not Quantified					Adult (>18 years old)	Both	Normal	HMDB	28157703
Human Urine	Detected but not Quantified					Adult (>18 years old)	Both	Normal	HMDB	32966057
Human Blood	Detected but not Quantified					Adult (>18 years old)	Both	Normal	HMDB	32966057

External Links

HMDB ID

HMDB0000195

DrugBank ID

DB04335

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Wikipedia Link

METLIN ID

PubChem Compound

6021

PDB ID

Not Available

ChEBI ID

17596

Food Biomarker Ontology

Not Available

CMMC Knowledgebase

Not Available

General References

Nakao T, Nagai F, Nakao M: Posttransfusion viability of rabbit erythrocytes preserved in a medium containing inosine, adenine, and isoosmotic sucrose. Vox Sang. 1982;42(4):217-22. doi: 10.1111/j.1423-0410.1982.tb01098.x. [PubMed:7090336 ]
Castro-Gago M, Cid E, Trabazo S, Pavon P, Camina F, Rodriguez-Segade S, Einis Punal J, Rodriguez-Nunez A: Cerebrospinal fluid purine metabolites and pyrimidine bases after brief febrile convulsions. Epilepsia. 1995 May;36(5):471-4. doi: 10.1111/j.1528-1157.1995.tb00488.x. [PubMed:7614924 ]
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Showing metabocard for Inosine (MMDBc0000064)

MOL for #<Metabolite:0x00007f1240c81528>

3D MOL for #<Metabolite:0x00007f1240c81528>

3D SDF for #<Metabolite:0x00007f1240c81528>

3D-SDF for #<Metabolite:0x00007f1240c81528>

PDB for #<Metabolite:0x00007f1240c81528>

3D PDB for #<Metabolite:0x00007f1240c81528>

SMILES for #<Metabolite:0x00007f1240c81528>

INCHI for #<Metabolite:0x00007f1240c81528>

Structure for #<Metabolite:0x00007f1240c81528>

3D Structure for #<Metabolite:0x00007f1240c81528>