NP-MRD: Showing NP-Card for Inosine (NP0000919)

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Record Information

Version

2.0

Created at

2005-11-16 15:48:42 UTC

Updated at

2022-02-04 02:32:15 UTC

NP-MRD ID

NP0000919

Secondary Accession Numbers

None

Natural Product 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 formed when hypoxanthine is attached to a ribose ring a beta-N9-glycosidic bond. Inosine is an intermediate in the degradation of purines and purine nucleosides to uric acid. Inosine is also an intermediate in the purine salvage pathway. Inosine occurs in the anticodon of certain transfer RNA molecules and is essential for proper translation of the genetic code in wobble base pairs. Inosine exists in all living species, ranging from bacteria to plants to humans. Inosine participates in a number of enzymatic reactions. In particular, inosine can be biosynthesized from inosinic acid through its interaction with the enzyme known as cytosolic purine 5'-nucleotidase. In addition, inosine can be converted into hypoxanthine and ribose 1-phosphate through its interaction with the enzyme known as purine nucleoside phosphorylase. Altered levels of inosine have also been associated with purine nucleoside phosphorylase deficiency and xanthinuria type I, both of which are inborn errors of metabolism. Animal studies have suggested that inosine has neuroprotective properties. It has been proposed as a potential treatment for spinal cord injury (PMID: 16317421 ) And for administration after stroke, as inosine appears to induce axonal rewiring (PMID: 12084941 ). After ingestion, inosine is metabolized into uric acid, which has been found to be a natural antioxidant and peroxynitrite scavenger. As such, inosine may have potential benefits to patients with multiple sclerosis and Parkinson’s disease (PMID: 19425822 ). Inosine can also be produced by gut bacteria and appears to have a number of beneficial effects. Inosine, has been shown to activate peroxisome proliferator-activated receptor (PPAR)-gamma signaling in human colon epithelial cells. Furthermore, exogenous treatment of inosine has been found to protect against DSS-induced colitis in rodents by improving adenosine 2A receptor (A2AR)/PPAR-gamma-dependent mucosal barrier functions (PMID: 33820558 ). Microbiome-derived inosine has also been shown to modulate the response to checkpoint inhibitor immunotherapy in cancer models. In particular, decreased gut barrier function induced by immunotherapy increases systemic translocation of bacterially derived inosine and activates antitumor T cells. The effect of inosine is dependent on T cell expression of the adenosine A2A receptor and requires co-stimulation. Inosine appears to have other roles in non-mammalian system. For instance, it has been found to be an important feed stimulant by itself or in combination with certain amino acids in some species of farmed fish. For example, inosine and inosine-5-monophosphate have been reported as specific feeding stimulants for turbot fry, (Scophthalmus maximus) and Japanese amberjack.

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>
NP0000919

> <DATABASE_NAME>
NP-MRD

> <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

View in JSmol

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

Chemical Formula

C₁₀H₁₂N₄O₅

Average Mass

268.2261 Da

Monoisotopic Mass

268.08077 Da

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=C1NC=NC2=O

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

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, simulated)	Ahselim			2022-02-04	View Spectrum
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
Abelmoschus esculentus	FooDB	FooDB
Actinidia chinensis	FooDB	FooDB
Agaricus bisporus	FooDB	FooDB
Agave	FooDB	FooDB
Allium ampeloprasum	FooDB	FooDB
Allium ascalonicum	FooDB	FooDB
Allium cepa	FooDB	FooDB
Allium cepa L.	FooDB	FooDB
Allium fistulosum	FooDB	FooDB
Allium sativum	FooDB	FooDB
Allium schoenoprasum	FooDB	FooDB
Allium tuberosum	FooDB	FooDB
Allium tuberosum Rottl.ex Spreng.	KNApSAcK Database	22123792
Aloysia triphylla	FooDB	FooDB
Amaranthus	FooDB	FooDB
Amelanchier alnifolia	FooDB	FooDB
Anacardium occidentale	FooDB	FooDB
Ananas comosus	FooDB	FooDB
Anas platyrhynchos	FooDB	FooDB
Anatidae	FooDB	FooDB
Anethum graveolens	FooDB	FooDB
Angelica keiskei	FooDB	FooDB
Annona cherimola	FooDB	FooDB
Annona muricata	FooDB	FooDB
Annona reticulata	FooDB	FooDB
Annona squamosa	FooDB	FooDB
Anser anser	FooDB	FooDB
Anthriscus cerefolium	FooDB	FooDB
Apium graveolens	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Apium graveolens var. dulce	FooDB	FooDB
Apium graveolens var. rapaceum	FooDB	FooDB
Apium graveolens var. secalinum	FooDB	FooDB
Aplysia kurodai	LOTUS Database	35616633
Arabidopsis thaliana	LOTUS Database	35616633
Arachis hypogaea	FooDB	FooDB
Arctium lappa	FooDB	FooDB
Armoracia rusticana	FooDB	FooDB
Artemisia dracunculus	FooDB	FooDB
Artemisia vulgaris	FooDB	FooDB
Artocarpus altilis	FooDB	FooDB
Artocarpus heterophyllus	FooDB	FooDB
Asparagus officinalis	FooDB	FooDB
Asterias forbesi	LOTUS Database	35616633
Attalea speciosa	FooDB	FooDB
Auricularia auricula-judae	FooDB	FooDB
Auricularia polytricha	FooDB	FooDB
Avena sativa L.	FooDB	FooDB
Averrhoa carambola	FooDB	FooDB
Basella alba	FooDB	FooDB
Benincasa hispida	FooDB	FooDB
Bertholletia excelsa	FooDB	FooDB
Beta vulgaris	KNApSAcK Database	22123792
Beta vulgaris ssp. cicla	FooDB	FooDB
Bison bison	FooDB	FooDB
Borago officinalis	FooDB	FooDB
Bos taurus	FooDB	FooDB
Bos taurus X Bison bison	FooDB	FooDB
Brassica alboglabra	FooDB	FooDB
Brassica juncea	FooDB	FooDB
Brassica napus	FooDB	FooDB
Brassica napus var. napus	FooDB	FooDB
Brassica oleracea	FooDB	FooDB
Brassica oleracea var. botrytis	FooDB	FooDB
Brassica oleracea var. capitata	FooDB	FooDB
Brassica oleracea var. gemmifera	FooDB	FooDB
Brassica oleracea var. gongylodes	FooDB	FooDB
Brassica oleracea var. italica	FooDB	FooDB
Brassica oleracea var. sabauda	FooDB	FooDB
Brassica oleracea var. viridis	FooDB	FooDB
Brassica rapa	FooDB	FooDB
Brassica rapa ssp. chinensis	FooDB	FooDB
Brassica rapa var. pekinensis	FooDB	FooDB
Brassica rapa var. rapa	FooDB	FooDB
Brassica ruvo	FooDB	FooDB
Brosimum alicastrum	FooDB	FooDB
Bubalus bubalis	FooDB	FooDB
Byrsonima crassifolia	FooDB	FooDB
Cajanus cajan	FooDB	FooDB
Canarium ovatum	FooDB	FooDB
Cannabis sativa	CannabisDB	Not Available
Cantharellus cibarius	FooDB	FooDB
Capparis spinosa	FooDB	FooDB
Capra aegagrus hircus	FooDB	FooDB
Capsicum annuum	FooDB	FooDB
Capsicum annuum L.	FooDB	FooDB
Capsicum annuum var. annuum	FooDB	FooDB
Capsicum chinense	FooDB	FooDB
Capsicum pubescens	FooDB	FooDB
Carica papaya L.	FooDB	FooDB
Carissa macrocarpa	FooDB	FooDB
Carthamus tinctorius	FooDB	FooDB
Carum carvi	FooDB	FooDB
Carya	FooDB	FooDB
Carya illinoinensis	FooDB	FooDB
Castanea	FooDB	FooDB
Castanea crenata	FooDB	FooDB
Castanea mollissima	FooDB	FooDB
Castanea sativa	FooDB	FooDB
Ceratonia siliqua	FooDB	FooDB
Cervidae	FooDB	FooDB
Cervus canadensis	FooDB	FooDB
Chamaemelum nobile	FooDB	FooDB
Chamerion angustifolium	FooDB	FooDB
Chenopodium album	FooDB	FooDB
Chenopodium quinoa	FooDB	FooDB
Chrysanthemum coronarium	FooDB	FooDB
Cicer arietinum	FooDB	FooDB
Cichorium endivia	FooDB	FooDB
Cichorium intybus	FooDB	FooDB
Cichorium pumilum	LOTUS Database	35616633
Cinnamomum	FooDB	FooDB
Cinnamomum aromaticum	FooDB	FooDB
Cinnamomum verum	FooDB	FooDB
Cirsium	FooDB	FooDB
Citrullus lanatus	FooDB	FooDB
Citrus ×limon (L.) Burm. f. (pro sp.)	FooDB	FooDB
Citrus aurantiifolia	FooDB	FooDB
Citrus latifolia	FooDB	FooDB
Citrus limon	FooDB	FooDB
Citrus maxima	FooDB	FooDB
Citrus paradisi	FooDB	FooDB
Citrus reticulata	FooDB	FooDB
Citrus X sinensis (L.) Osbeck (pro. sp.)	FooDB	FooDB
Cocos nucifera	FooDB	FooDB
Coffea arabica L.	FooDB	FooDB
Coffea canephora	FooDB	FooDB
Colocasia esculenta	FooDB	FooDB
Columba	FooDB	FooDB
Columbidae	FooDB	FooDB
Corchorus olitorius	FooDB	FooDB
Coriandrum sativum L.	FooDB	FooDB
Corylus	FooDB	FooDB
Corylus avellana	FooDB	FooDB
Crateva religiosa	FooDB	FooDB
Crocus sativus	FooDB	FooDB
Cucumis melo	FooDB	FooDB
Cucumis metuliferus	FooDB	FooDB
Cucumis sativus L.	FooDB	FooDB
Cucurbita	FooDB	FooDB
Cucurbita maxima	FooDB	FooDB
Cucurbita moschata	FooDB	FooDB
Cuminum cyminum	FooDB	FooDB
Curcuma longa	FooDB	FooDB
Cydonia oblonga	FooDB	FooDB
Cymbopogon citratus	FooDB	FooDB
Cynara cardunculus	FooDB	FooDB
Cynara scolymus	FooDB	FooDB
Daphnia pulex	LOTUS Database	35616633
Daucus carota	FooDB	FooDB
Daucus carota ssp. sativus	FooDB	FooDB
Dimocarpus longan	FooDB	FooDB
Dioscorea	FooDB	FooDB
Dioscorea pentaphylla	FooDB	FooDB
Diospyros	FooDB	FooDB
Diospyros kaki	FooDB	FooDB
Diospyros virginiana	FooDB	FooDB
Dromaius novaehollandiae	FooDB	FooDB
Durio zibethinus	FooDB	FooDB
Dysphania ambrosioides	FooDB	FooDB
Elaeis	FooDB	FooDB
Eleocharis dulcis	FooDB	FooDB
Elettaria cardamomum	FooDB	FooDB
Empetrum nigrum	FooDB	FooDB
Equus caballus	FooDB	FooDB
Eragrostis tef	FooDB	FooDB
Eriobotrya japonica	FooDB	FooDB
Eruca vesicaria subsp. Sativa	FooDB	FooDB
Erwinia carotovora	LOTUS Database	35616633
Eugenia javanica	FooDB	FooDB
Eugenia uniflora	FooDB	FooDB
Eutrema japonicum	FooDB	FooDB
Fagopyrum esculentum	FooDB	FooDB
Fagopyrum tataricum	FooDB	FooDB
Fagus	FooDB	FooDB
Feijoa sellowiana	FooDB	FooDB
Ficus carica	FooDB	FooDB
Flammulina velutipes	FooDB	FooDB
Foeniculum vulgare	FooDB	FooDB
Fragaria x ananassa	FooDB	FooDB
Fritillaria cirrhosa	KNApSAcK Database	22123792
Fritillaria thunbergii	LOTUS Database	35616633
Gallus gallus	FooDB	FooDB
Garcinia mangostana	FooDB	FooDB
Gaylussacia baccata	FooDB	FooDB
Geodia barretti	LOTUS Database	35616633
Ginkgo biloba	FooDB	FooDB
Glycine max	FooDB	FooDB
Gossypium	FooDB	FooDB
Grifola frondosa	FooDB	FooDB
Hedysarum alpinum	FooDB	FooDB
Helianthus annuus L.	FooDB	FooDB
Helianthus tuberosus	FooDB	FooDB
Hibiscus sabbariffa	FooDB	FooDB
Hippophae rhamnoides	FooDB	FooDB
Homo sapiens	LOTUS Database	35616633
Hordeum vulgare	FooDB	FooDB
Hyssopus officinalis L.	FooDB	FooDB
Illicium verum	FooDB	FooDB
Ipomoea aquatica	FooDB	FooDB
Ipomoea batatas	FooDB	FooDB
Isodictya erinacea	LOTUS Database	35616633
Juglans	FooDB	FooDB
Juglans ailanthifolia	FooDB	FooDB
Juglans cinerea	FooDB	FooDB
Juglans nigra L.	FooDB	FooDB
Juglans regia	FooDB	FooDB
Lablab purpureus	FooDB	FooDB
Lactuca sativa	FooDB	FooDB
Lagenaria siceraria	FooDB	FooDB
Lagopus muta	FooDB	FooDB
Lasiodiplodia theobromae	LOTUS Database	35616633
Lates calcarifer	LOTUS Database	35616633
Lathyrus sativus	FooDB	FooDB
Laurus nobilis L.	FooDB	FooDB
Lens culinaris	FooDB	FooDB
Lentinus edodes	FooDB	FooDB
Lepidium sativum	FooDB	FooDB
Leporidae	FooDB	FooDB
Lepus timidus	FooDB	FooDB
Levisticum officinale	FooDB	FooDB
Linum usitatissimum	FooDB	FooDB
Litchi chinensis	FooDB	FooDB
Luffa aegyptiaca	FooDB	FooDB
Lupinus	FooDB	FooDB
Lupinus albus	FooDB	FooDB
Macadamia	FooDB	FooDB
Macadamia tetraphylla	FooDB	FooDB
Malpighia emarginata	FooDB	FooDB
Malus	FooDB	FooDB
Malus pumila	FooDB	FooDB
Mammea americana	FooDB	FooDB
Mangifera indica	FooDB	FooDB
Manihot esculenta	FooDB	FooDB
Manilkara zapota	FooDB	FooDB
Maranta arundinacea	FooDB	FooDB
Matricaria recutita	FooDB	FooDB
Matteuccia struthiopteris	FooDB	FooDB
Medicago sativa	FooDB	FooDB
Melanitta fusca	FooDB	FooDB
Meleagris gallopavo	FooDB	FooDB
Melissa officinalis L.	FooDB	FooDB
Mentha	FooDB	FooDB
Mentha aquatica	FooDB	FooDB
Mentha arvensis	FooDB	FooDB
Mentha spicata	FooDB	FooDB
Mentha x piperita	FooDB	FooDB
Mespilus germanica	FooDB	FooDB
Metroxylon sagu	FooDB	FooDB
Momordica charantia	FooDB	FooDB
Morchellaceae	FooDB	FooDB
Morella rubra	FooDB	FooDB
Moringa oleifera	FooDB	FooDB
Morus	FooDB	FooDB
Morus nigra	FooDB	FooDB
Mus musculus	LOTUS Database	35616633
Musa acuminata	FooDB	FooDB
Musa x paradisiaca	FooDB	FooDB
Myrica	FooDB	FooDB
Myristica fragrans	FooDB	FooDB
Naja kaouthia	LOTUS Database	35616633
Naja naja	LOTUS Database	35616633
Nelumbo	FooDB	FooDB
Nelumbo nucifera	FooDB	FooDB
Nephelium lappaceum	FooDB	FooDB
Neptunea antiqua	LOTUS Database	35616633
Numida meleagris	FooDB	FooDB
Nuphar lutea	FooDB	FooDB
Ocimum basilicum	FooDB	FooDB
Odocoileus	FooDB	FooDB
Oenothera biennis	FooDB	FooDB
Olea europaea	FooDB	FooDB
Ophiocordyceps sinensis	Fungi	KNApSAcK
Opuntia	FooDB	FooDB
Opuntia cochenillifera	FooDB	FooDB
Opuntia macrorhiza	FooDB	FooDB
Origanum majorana	FooDB	FooDB
Origanum onites	FooDB	FooDB
Origanum vulgare	FooDB	FooDB
Origanum X majoricum	FooDB	FooDB
Oryctolagus	FooDB	FooDB
Oryza rufipogon	FooDB	FooDB
Oryza sativa	FooDB	FooDB
Ovis aries	FooDB	FooDB
Pachliopta aristolochiae	LOTUS Database	35616633
Pachyrhizus erosus	FooDB	FooDB
Panax ginseng	FooDB	FooDB
Pangium edule	FooDB	FooDB
Panicum miliaceum	FooDB	FooDB
Passiflora edulis	FooDB	FooDB
Pastinaca sativa	FooDB	FooDB
Pediomelum esculentum	FooDB	FooDB
Perideridia oregana	FooDB	FooDB
Persea americana	FooDB	FooDB
Petasites japonicus	FooDB	FooDB
Petroselinum crispum	FooDB	FooDB
Phaseolus coccineus	FooDB	FooDB
Phaseolus lunatus	FooDB	FooDB
Phaseolus vulgaris	FooDB	FooDB
Phasianidae	FooDB	FooDB
Phasianus colchicus	FooDB	FooDB
Phoenix dactylifera	FooDB	FooDB
Photinia melanocarpa	FooDB	FooDB
Phyllostachys edulis	FooDB	FooDB
Physalis	FooDB	FooDB
Physalis philadelphica var. immaculata	FooDB	FooDB
Phytolacca americana	FooDB	FooDB
Pimenta dioica	FooDB	FooDB
Pimpinella anisum	FooDB	FooDB
Pinus	FooDB	FooDB
Pinus edulis	FooDB	FooDB
Piper nigrum L.	FooDB	FooDB
Pistacia vera	FooDB	FooDB
Pisum sativum	FooDB	FooDB
Pleurotus ostreatus	FooDB	FooDB
Polygonum alpinum	FooDB	FooDB
Portulaca oleracea	FooDB	FooDB
Pouteria sapota	FooDB	FooDB
Prunus armeniaca	FooDB	FooDB
Prunus avium	FooDB	FooDB
Prunus avium L.	FooDB	FooDB
Prunus cerasus	FooDB	FooDB
Prunus domestica	FooDB	FooDB
Prunus dulcis	FooDB	FooDB
Prunus persica	FooDB	FooDB
Prunus persica var. nucipersica	FooDB	FooDB
Prunus persica var. persica	FooDB	FooDB
Prunus tomentosa	FooDB	FooDB
Prunus virginiana	FooDB	FooDB
Pseudo-nitzschia multistriata	LOTUS Database	35616633
Psidium cattleianum	FooDB	FooDB
Psidium guajava	FooDB	FooDB
Psophocarpus tetragonolobus	FooDB	FooDB
Punica granatum	FooDB	FooDB
Pyrus communis	FooDB	FooDB
Pyrus pyrifolia	FooDB	FooDB
Quercus	FooDB	FooDB
Raphanus sativus	FooDB	FooDB
Raphanus sativus var. longipinnatus	FooDB	FooDB
Raphanus sativus var. sativus	FooDB	FooDB
Reboulia hemisphaerica	LOTUS Database	35616633
Rheum rhabarbarum	FooDB	FooDB
Ribes aureum	FooDB	FooDB
Ribes glandulosum	FooDB	FooDB
Ribes nigrum	FooDB	FooDB
Ribes rubrum	FooDB	FooDB
Ribes uva-crispa	FooDB	FooDB
Rosa	FooDB	FooDB
Rubus arcticus	FooDB	FooDB
Rubus chamaemorus	FooDB	FooDB
Rubus idaeus	FooDB	FooDB
Rubus occidentalis	FooDB	FooDB
Rubus spectabilis	FooDB	FooDB
Rumex	FooDB	FooDB
Rumex acetosa	FooDB	FooDB
Rumex articus	FooDB	FooDB
Russula cyanoxantha	LOTUS Database	35616633
Sagittaria latifolia	FooDB	FooDB
Salix pulchra	FooDB	FooDB
Salvia elegans	FooDB	FooDB
Salvia hispanica	FooDB	FooDB
Salvia officinalis	FooDB	FooDB
Salvia rosmarinus	FooDB	FooDB
Sambucus nigra	FooDB	FooDB
Sambucus nigra L.	FooDB	FooDB
Satureja hortensis L.	FooDB	FooDB
Satureja montana	FooDB	FooDB
Scorzonera hispanica	FooDB	FooDB
Secale cereale	FooDB	FooDB
Sechium edule	FooDB	FooDB
Sesamum indicum	FooDB	FooDB
Sesbania bispinosa	FooDB	FooDB
Sinapis alba	FooDB	FooDB
Sisymbrium	FooDB	FooDB
Solanum lycopersicum	FooDB	FooDB
Solanum lycopersicum var. cerasiforme	FooDB	FooDB
Solanum lycopersicum var. lycopersicum	FooDB	FooDB
Solanum melongena	FooDB	FooDB
Solanum quitoense	FooDB	FooDB
Solanum tuberosum	FooDB	FooDB
Sorbus aucuparia	FooDB	FooDB
Sorghum bicolor	FooDB	FooDB
Spinacia oleracea	FooDB	FooDB
Struthio camelus	FooDB	FooDB
Sus scrofa	FooDB	FooDB
Sus scrofa domestica	FooDB	FooDB
Synechococcus elongatus	LOTUS Database	35616633
Syzygium aromaticum	FooDB	FooDB
Syzygium cumini	FooDB	FooDB
Syzygium jambos	FooDB	FooDB
Tamarindus indica	FooDB	FooDB
Taraxacum officinale	FooDB	FooDB
Tetragonia tetragonioides	FooDB	FooDB
Thelesperma	FooDB	FooDB
Thymus pulegioides	FooDB	FooDB
Thymus vulgaris	FooDB	FooDB
Tilia cordata	FooDB	FooDB
Tilia L.	FooDB	FooDB
Tragopogon porrifolius	FooDB	FooDB
Trigonella foenum-graecum	FooDB	FooDB
Triticum	FooDB	FooDB
Triticum aestivum	FooDB	FooDB
Triticum durum	FooDB	FooDB
Triticum spelta	FooDB	FooDB
Triticum turanicum	FooDB	FooDB
Trypanosoma brucei	LOTUS Database	35616633
Typha angustifolia	FooDB	FooDB
Vaccinium	FooDB	FooDB
Vaccinium angustifolium	FooDB	FooDB
Vaccinium angustifolium X Vaccinium corymbosum	FooDB	FooDB
Vaccinium arboreum	FooDB	FooDB
Vaccinium corymbosum	FooDB	FooDB
Vaccinium deliciosum	FooDB	FooDB
Vaccinium elliottii	FooDB	FooDB
Vaccinium macrocarpon	FooDB	FooDB
Vaccinium myrtilloides	FooDB	FooDB
Vaccinium myrtillus	FooDB	FooDB
Vaccinium ovalifolium	FooDB	FooDB
Vaccinium ovatum	FooDB	FooDB
Vaccinium oxycoccos	FooDB	FooDB
Vaccinium parvifolium	FooDB	FooDB
Vaccinium reticulatum	FooDB	FooDB
Vaccinium stamineum	FooDB	FooDB
Vaccinium uliginosum	FooDB	FooDB
Vaccinium vitis-idaea	FooDB	FooDB
Valerianella locusta	FooDB	FooDB
Vanilla	FooDB	FooDB
Verbena officinalis	FooDB	FooDB
Viburnum edule	FooDB	FooDB
Vicia faba	FooDB	FooDB
Vigna aconitifolia	FooDB	FooDB
Vigna angularis	FooDB	FooDB
Vigna mungo	FooDB	FooDB
Vigna radiata	FooDB	FooDB
Vigna umbellata	FooDB	FooDB
Vigna unguiculata	FooDB	FooDB
Vigna unguiculata ssp. cylindrica	FooDB	FooDB
Vigna unguiculata ssp. unguiculata	FooDB	FooDB
Vigna unguiculata var. sesquipedalis	FooDB	FooDB
Vitis	FooDB	FooDB
Vitis aestivalis	FooDB	FooDB
Vitis labrusca	FooDB	FooDB
Vitis rotundifolia	FooDB	FooDB
Vitis vinifera L.	FooDB	FooDB
Xanthosoma sagittifolium	FooDB	FooDB
Zea mays L.	FooDB	FooDB
Zingiber officinale	FooDB	FooDB
Zizania	FooDB	FooDB
Zizania aquatica	FooDB	FooDB
Ziziphus jujuba	LOTUS Database	35616633
Ziziphus zizyphus	FooDB	FooDB

Species Where Detected

Species Name	Source	Reference
Cordyceps militaris cv.	KNApSAcK Database	22123792
Cordyceps sinensis	KNApSAcK Database	22123792
Escherichia coli	KNApSAcK Database	22123792
Homo sapiens (Urine)	KNApSAcK Database	22123792

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 )

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	218 °C	Not Available
Boiling Point	732.82 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	15.8 mg/mL	Yalkowsky, S. H., & Dannenfelser, R. M. (1992). Aquasol database of aqueous solubility. College of Pharmacy, University of Arizona, Tucson, AZ, 189.
LogP	-2.10	Hansch CH, Leo A and Hoekman DH. "Exploring QSAR: Hydrophobic, Electronic, and Steric Constraints. Volume 1" ACS Publications (1995).

Predicted Properties

Property	Value	Source
Water Solubility	13.8 g/L	ALOGPS
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

External Links

HMDB ID

HMDB0000195

DrugBank ID

DB04335

Phenol Explorer Compound ID

Not Available

FoodDB 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

Good Scents ID

rw1136831

References

General References

Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. doi: 10.1038/nature07762. [PubMed:19212411 ]
Eells JT, Spector R: Purine and pyrimidine base and nucleoside concentrations in human cerebrospinal fluid and plasma. Neurochem Res. 1983 Nov;8(11):1451-7. [PubMed:6656991 ]
Nakayama Y, Kinoshita A, Tomita M: Dynamic simulation of red blood cell metabolism and its application to the analysis of a pathological condition. Theor Biol Med Model. 2005 May 9;2:18. [PubMed:15882454 ]
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 ]
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. [PubMed:7614924 ]
Rodriguez-Nunez A, Camina F, Lojo S, Rodriguez-Segade S, Castro-Gago M: Concentrations of nucleotides, nucleosides, purine bases and urate in cerebrospinal fluid of children with meningitis. Acta Paediatr. 1993 Oct;82(10):849-52. [PubMed:8241644 ]
Scott GS, Spitsin SV, Kean RB, Mikheeva T, Koprowski H, Hooper DC: Therapeutic intervention in experimental allergic encephalomyelitis by administration of uric acid precursors. Proc Natl Acad Sci U S A. 2002 Dec 10;99(25):16303-8. Epub 2002 Nov 25. [PubMed:12451183 ]
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. [PubMed:7090336 ]
Harkness RA, Lund RJ: Cerebrospinal fluid concentrations of hypoxanthine, xanthine, uridine and inosine: high concentrations of the ATP metabolite, hypoxanthine, after hypoxia. J Clin Pathol. 1983 Jan;36(1):1-8. [PubMed:6681617 ]
Hsiao G, Lin KH, Chang Y, Chen TL, Tzu NH, Chou DS, Sheu JR: Protective mechanisms of inosine in platelet activation and cerebral ischemic damage. Arterioscler Thromb Vasc Biol. 2005 Sep;25(9):1998-2004. Epub 2005 Jun 23. [PubMed:15976325 ]
Jabs CM, Sigurdsson GH, Neglen P: Plasma levels of high-energy compounds compared with severity of illness in critically ill patients in the intensive care unit. Surgery. 1998 Jul;124(1):65-72. [PubMed:9663253 ]
Fazekas L, Horkay F, Kekesi V, Huszar E, Barat E, Fazekas R, Szabo T, Juhasz-Nagy A, Naszlady A: Enhanced accumulation of pericardial fluid adenosine and inosine in patients with coronary artery disease. Life Sci. 1999;65(10):1005-12. [PubMed:10499868 ]
Mattle HP, Lienert C, Greeve I: [Uric acid and multiple sclerosis]. Ther Umsch. 2004 Sep;61(9):553-5. [PubMed:15493114 ]
Fukumori Y, Takeda H, Fujisawa T, Ushijima K, Onodera S, Shiomi N: Blood glucose and insulin concentrations are reduced in humans administered sucrose with inosine or adenosine. J Nutr. 2000 Aug;130(8):1946-9. [PubMed:10917906 ]
Burger DM, Kraayeveld CL, Meenhorst PL, Mulder JW, Hoetelmans RM, Koks CH, Beijnen JH: Study on didanosine concentrations in cerebrospinal fluid. Implications for the treatment and prevention of AIDS dementia complex. Pharm World Sci. 1995 Nov 24;17(6):218-21. [PubMed:8597780 ]
Mabley JG, Rabinovitch A, Suarez-Pinzon W, Hasko G, Pacher P, Power R, Southan G, Salzman A, Szabo C: Inosine protects against the development of diabetes in multiple-low-dose streptozotocin and nonobese diabetic mouse models of type 1 diabetes. Mol Med. 2003 Mar-Apr;9(3-4):96-104. [PubMed:12865945 ]
Yamamoto T, Moriwaki Y, Cheng J, Takahashi S, Tsutsumi Z, Ka T, Hada T: Effect of inosine on the plasma concentration of uridine and purine bases. Metabolism. 2002 Apr;51(4):438-42. [PubMed:11912550 ]
Kurtz TW, Kabra PM, Booth BE, Al-Bander HA, Portale AA, Serena BG, Tsai HC, Morris RC Jr: Liquid-chromatographic measurements of inosine, hypoxanthine, and xanthine in studies of fructose-induced degradation of adenine nucleotides in humans and rats. Clin Chem. 1986 May;32(5):782-6. [PubMed:3698269 ]
Niwa T, Takeda N, Yoshizumi H: RNA metabolism in uremic patients: accumulation of modified ribonucleosides in uremic serum. Technical note. Kidney Int. 1998 Jun;53(6):1801-6. [PubMed:9607216 ]
Osborne WR, Hammond WP, Dale DC: Human cyclic hematopoiesis is associated with aberrant purine metabolism. J Lab Clin Med. 1985 Apr;105(4):403-9. [PubMed:3981053 ]
Liu F, You SW, Yao LP, Liu HL, Jiao XY, Shi M, Zhao QB, Ju G: Secondary degeneration reduced by inosine after spinal cord injury in rats. Spinal Cord. 2006 Jul;44(7):421-6. doi: 10.1038/sj.sc.3101878. Epub 2005 Nov 29. [PubMed:16317421 ]
Chen P, Goldberg DE, Kolb B, Lanser M, Benowitz LI: Inosine induces axonal rewiring and improves behavioral outcome after stroke. Proc Natl Acad Sci U S A. 2002 Jun 25;99(13):9031-6. doi: 10.1073/pnas.132076299. [PubMed:12084941 ]
Markowitz CE, Spitsin S, Zimmerman V, Jacobs D, Udupa JK, Hooper DC, Koprowski H: The treatment of multiple sclerosis with inosine. J Altern Complement Med. 2009 Jun;15(6):619-25. doi: 10.1089/acm.2008.0513. [PubMed:19425822 ]
Li D, Feng Y, Tian M, Ji J, Hu X, Chen F: Gut microbiota-derived inosine from dietary barley leaf supplementation attenuates colitis through PPARgamma signaling activation. Microbiome. 2021 Apr 5;9(1):83. doi: 10.1186/s40168-021-01028-7. [PubMed:33820558 ]
Stegmann KM, Dickmanns A, Gerber S, Nikolova V, Klemke L, Manzini V, Schlosser D, Bierwirth C, Freund J, Sitte M, Lugert R, Salinas G, Meister TL, Pfaender S, Gorlich D, Wollnik B, Gross U, Dobbelstein M: The folate antagonist methotrexate diminishes replication of the coronavirus SARS-CoV-2 and enhances the antiviral efficacy of remdesivir in cell culture models. Virus Res. 2021 Sep;302:198469. doi: 10.1016/j.virusres.2021.198469. Epub 2021 Jun 6. [PubMed:34090962 ]

Showing NP-Card for Inosine (NP0000919)

MOL for NP0000919 (Inosine)

3D MOL for NP0000919 (Inosine)

3D SDF for NP0000919 (Inosine)

3D-SDF for NP0000919 (Inosine)

PDB for NP0000919 (Inosine)

3D PDB for NP0000919 (Inosine)

SMILES for NP0000919 (Inosine)

INCHI for NP0000919 (Inosine)

Structure for NP0000919 (Inosine)

3D Structure for NP0000919 (Inosine)