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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (13) Show 13 proteins XML

Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2023-05-30 20:55:52 UTC

HMDB ID

HMDB0000195

Secondary Accession Numbers

HMDB00195

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 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‚Äôs 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>
HMDB0000195

> <DATABASE_NAME>
hmdb

> <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 View NMR Assignments View Stereo Labels

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 Molecular Weight

268.2261

Monoisotopic Molecular Weight

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 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 9663253)
Cerebrospinal Fluid (CSF) (PMID: 8597780)
Pericardial Effusion (PMID: 10499868)
Cellular Cytoplasm (PMID: 15882454)
Saliva (PMID: 11310987)

Organ

Cell

Hematocyte

Platelet (HMDB: HMDB0000195)

Excreta

Biofluid or Excreta

Urine (PMID: 16139832)
Feces (PMID: 21330412)

Cellular substructure

Cytoplasm (HMDB: HMDB0000195)
Extracellular (HMDB: HMDB0000195)

Organelle

Lysosome (HMDB: HMDB0000195)
Mitochondrion (HMDB: HMDB0000195)

Source

Exogenous

Exogenous (HMDB: HMDB0000195)

Food

Animal origin

Poultry

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

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

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

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

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

Equine

Horse (FooDB: FOOD00378)

Herb and spice mixture

Curry powder (FooDB: FOOD00678)

Herbs and Spices (FooDB: FOOD00866)

Vegetable

Cabbage

Onion-family vegetable

Allium (FooDB: FOOD00005)
Garden onion (FooDB: FOOD00006)
Leek (FooDB: FOOD00007)
Garden onion (var.) (FooDB: FOOD00226)
Shallot (FooDB: FOOD00243)
Wild leek (FooDB: FOOD00396)
Red onion (FooDB: FOOD00962)
Green onion (FooDB: FOOD00963)
Onion-family vegetables (FooDB: FOOD00855)

Root vegetable

Shoot vegetable

Leaf vegetable

Common beet (FooDB: FOOD00025)
Endive (FooDB: FOOD00048)
Rocket salad (ssp.) (FooDB: FOOD00077)
Swamp cabbage (FooDB: FOOD00091)
Lettuce (FooDB: FOOD00095)
Garden cress (FooDB: FOOD00099)
Spinach (FooDB: FOOD00178)
Swiss chard (FooDB: FOOD00237)
Chicory leaves (FooDB: FOOD00250)
Garland chrysanthemum (FooDB: FOOD00333)
Corn salad (FooDB: FOOD00340)
Jute (FooDB: FOOD00389)
Lambsquarters (FooDB: FOOD00394)
Malabar spinach (FooDB: FOOD00404)
New Zealand spinach (FooDB: FOOD00415)
Yautia (FooDB: FOOD00510)
Ostrich fern (FooDB: FOOD00556)
Romaine lettuce (FooDB: FOOD00888)
Iceberg lettuce (FooDB: FOOD00973)
Pea shoots (FooDB: FOOD00975)
Yau choy (FooDB: FOOD00976)
Water spinach (FooDB: FOOD00977)
Rocket salad (FooDB: FOOD00244)
Green vegetables (FooDB: FOOD00872)

Fruit vegetable

Pepper (FooDB: FOOD00040)
Olive (FooDB: FOOD00121)
Avocado (FooDB: FOOD00130)
Garden tomato (FooDB: FOOD00171)
Cherry tomato (FooDB: FOOD00172)
Garden tomato (var.) (FooDB: FOOD00173)
Eggplant (FooDB: FOOD00174)
Pepper (C. baccatum) (FooDB: FOOD00231)
Pepper (C. chinense) (FooDB: FOOD00232)
Pepper (Capsicum) (FooDB: FOOD00233)
Groundcherry (FooDB: FOOD00371)
Pepper (C. frutescens) (FooDB: FOOD00428)
Mexican groundcherry (FooDB: FOOD00491)
Pepper (C. pubescens) (FooDB: FOOD00849)
Green bell pepper (FooDB: FOOD00877)
Yellow bell pepper (FooDB: FOOD00878)
Orange bell pepper (FooDB: FOOD00879)
Red bell pepper (FooDB: FOOD00880)
Italian sweet red pepper (FooDB: FOOD00881)
Jalapeno pepper (FooDB: FOOD00955)
Cubanelle pepper (FooDB: FOOD00971)

Tuber

Stalk vegetable

Other vegetable

Giant butterbur (FooDB: FOOD00314)
Carob (FooDB: FOOD00321)
Chinese water chestnut (FooDB: FOOD00332)
Horseradish tree (FooDB: FOOD00379)
Sacred lotus (FooDB: FOOD00402)
Nopal (FooDB: FOOD00416)
Okra (FooDB: FOOD00420)
Sesbania flower (FooDB: FOOD00469)
Agave (FooDB: FOOD00563)
Narrowleaf cattail (FooDB: FOOD00564)
Heart of palm (FooDB: FOOD00718)
Tree fern (FooDB: FOOD00797)

Mushroom

Castanospermum australe (FooDB: FOOD00893)
Gentiana lutea (FooDB: FOOD00894)
Juniperus communis (FooDB: FOOD00895)
Albizia gummifera (FooDB: FOOD00896)

Brassica

Brassicas (FooDB: FOOD00857)

Fruit

Tropical fruit

Citrus

Lime (FooDB: FOOD00053)
Lemon (FooDB: FOOD00054)
Pummelo (FooDB: FOOD00055)
Mandarin orange (Clementine, Tangerine) (FooDB: FOOD00056)
Sweet orange (FooDB: FOOD00057)
Grapefruit/Pummelo hybrid (FooDB: FOOD00255)
Grapefruit (FooDB: FOOD00256)
Persian lime (FooDB: FOOD00543)
Sour orange (FooDB: FOOD00918)
Mikan (FooDB: FOOD00932)
Clementine (FooDB: FOOD00959)
Citrus (FooDB: FOOD00859)

Pome

Berry

Black crowberry (FooDB: FOOD00075)
Strawberry (FooDB: FOOD00083)
Black huckleberry (FooDB: FOOD00084)
Sea-buckthornberry (FooDB: FOOD00087)
Mulberry (FooDB: FOOD00116)
Black mulberry (FooDB: FOOD00117)
Black chokeberry (FooDB: FOOD00136)
Blackcurrant (FooDB: FOOD00155)
Redcurrant (FooDB: FOOD00156)
Gooseberry (FooDB: FOOD00157)
Cloudberry (FooDB: FOOD00161)
Red raspberry (FooDB: FOOD00162)
Black raspberry (FooDB: FOOD00163)
Black elderberry (FooDB: FOOD00166)
Rowanberry (FooDB: FOOD00176)
Vaccinium (Blueberry, Cranberry, Huckleberry) (FooDB: FOOD00188)
Lowbush blueberry (FooDB: FOOD00189)
Sparkleberry (FooDB: FOOD00190)
Highbush blueberry (FooDB: FOOD00191)
American cranberry (FooDB: FOOD00192)
Bilberry (FooDB: FOOD00193)
Lingonberry (FooDB: FOOD00194)
Muscadine grape (FooDB: FOOD00203)
Common grape (FooDB: FOOD00204)
Arctic blackberry (FooDB: FOOD00207)
Bayberry (FooDB: FOOD00209)
Elliott's blueberry (FooDB: FOOD00210)
Canada blueberry (FooDB: FOOD00211)
Bog bilberry (FooDB: FOOD00212)
Buffalo currant (FooDB: FOOD00213)
European cranberry (FooDB: FOOD00217)
Deerberry (FooDB: FOOD00218)
Cascade huckleberry (FooDB: FOOD00220)
Oval-leaf huckleberry (FooDB: FOOD00221)
Evergreen huckleberry (FooDB: FOOD00222)
Red huckleberry (FooDB: FOOD00223)
Summer grape (FooDB: FOOD00227)
Fox grape (FooDB: FOOD00228)
Half-highbush blueberry (FooDB: FOOD00248)
Jostaberry (FooDB: FOOD00257)
Sweet rowanberry (FooDB: FOOD00265)
Skunk currant (FooDB: FOOD00267)
Squashberry (FooDB: FOOD00344)
Elderberry (FooDB: FOOD00358)
Grape (FooDB: FOOD00369)
Alaska blueberry (FooDB: FOOD00380)
Loganberry (FooDB: FOOD00400)
Ohelo berry (FooDB: FOOD00419)
Salmonberry (FooDB: FOOD00456)
Strawberry guava (FooDB: FOOD00482)
Boysenberry (FooDB: FOOD00542)
Chinese bayberry (FooDB: FOOD00852)
Saskatoon berry (FooDB: FOOD00884)
Nanking cherry (FooDB: FOOD00885)
Rabbiteye blueberry (FooDB: FOOD00898)
Blackberry (FooDB: FOOD00906)
Partridge berry (FooDB: FOOD00931)
Green grape (FooDB: FOOD00964)
Red grape (FooDB: FOOD00965)
Black plum (FooDB: FOOD00966)
Black raisin (FooDB: FOOD00968)
Chinese plum (FooDB: FOOD00978)
Green plum (FooDB: FOOD00979)
Wampee (FooDB: FOOD00980)
Goji (FooDB: FOOD00982)
Monk fruit (FooDB: FOOD00983)
Hawthorn (FooDB: FOOD00985)
Lantern fruit (FooDB: FOOD00986)
Cape gooseberry (FooDB: FOOD00988)
Rubus (Blackberry, Raspberry) (FooDB: FOOD00160)

Other fruit

Fig (FooDB: FOOD00081)
Date (FooDB: FOOD00135)
Jujube (FooDB: FOOD00388)

Drupe

Prunus (Cherry, Plum) (FooDB: FOOD00143)
Apricot (FooDB: FOOD00144)
Sweet cherry (FooDB: FOOD00145)
Sour cherry (FooDB: FOOD00146)
European plum (FooDB: FOOD00147)
Peach (FooDB: FOOD00149)
Nectarine (FooDB: FOOD00229)
Peach (var.) (FooDB: FOOD00230)
Common chokecherry (FooDB: FOOD00562)

Fruits (FooDB: FOOD00871)

Nut

Cashew nut (FooDB: FOOD00011)
Peanut (FooDB: FOOD00016)
Brazil nut (FooDB: FOOD00024)
Pecan nut (FooDB: FOOD00044)
Chestnut (FooDB: FOOD00045)
Common hazelnut (FooDB: FOOD00062)
Black walnut (FooDB: FOOD00093)
Common walnut (FooDB: FOOD00094)
Pine nut (FooDB: FOOD00138)
Pistachio (FooDB: FOOD00140)
Almond (FooDB: FOOD00148)
Macadamia nut (M. tetraphylla) (FooDB: FOOD00225)
Japanese walnut (FooDB: FOOD00240)
Acorn (FooDB: FOOD00282)
Beech nut (FooDB: FOOD00299)
Butternut (FooDB: FOOD00316)
Chinese chestnut (FooDB: FOOD00331)
European chestnut (FooDB: FOOD00363)
Hazelnut (FooDB: FOOD00376)
Hickory nut (FooDB: FOOD00377)
Japanese chestnut (FooDB: FOOD00385)
Pili nut (FooDB: FOOD00432)
Colorado pinyon (FooDB: FOOD00433)
Macadamia nut (FooDB: FOOD00525)
Walnut (FooDB: FOOD00608)
Mixed nuts (FooDB: FOOD00771)
Nuts (FooDB: FOOD00869)

Cereal and cereal product

Cereal

Cereal product

Dough

Sourdough (FooDB: FOOD00275)

Leavened bread

Flat bread

Other bread

Potato bread (FooDB: FOOD00811)
Other bread (FooDB: FOOD00269)

Sweet bread

Raisin bread (FooDB: FOOD00817)

Cereals and cereal products (FooDB: FOOD00858)

Pulse

Pea

Lentil

Lentils (FooDB: FOOD00098)

Other pulse

Lupine (FooDB: FOOD00104)
White lupine (FooDB: FOOD00403)

Bean

Green lentil (FooDB: FOOD00970)
Pulses (FooDB: FOOD00867)

Gourd

Watermelon (FooDB: FOOD00052)
Muskmelon (FooDB: FOOD00064)
Cucumber (FooDB: FOOD00065)
Cucurbita (FooDB: FOOD00066)
Bitter gourd (FooDB: FOOD00115)
Winter squash (FooDB: FOOD00283)
Butternut squash (FooDB: FOOD00317)
Calabash (FooDB: FOOD00318)
Chayote (FooDB: FOOD00325)
Towel gourd (FooDB: FOOD00492)
Wax gourd (FooDB: FOOD00499)
Tinda (FooDB: FOOD00559)
Horned melon (FooDB: FOOD00761)
Sunburst squash (pattypan squash) (FooDB: FOOD00874)
Green zucchini (FooDB: FOOD00875)
Yellow zucchini (FooDB: FOOD00876)
Japanese pumpkin (FooDB: FOOD00886)
Acorn squash (FooDB: FOOD00972)
Cantaloupe melon (FooDB: FOOD00984)

Coffee and coffee product

Coffee

Arabica coffee (FooDB: FOOD00059)
Robusta coffee (FooDB: FOOD00060)

Soy

Soy bean (FooDB: FOOD00085)

Soy product

Dish

Other dish

Taco shell (FooDB: FOOD00991)
Tostada shell (FooDB: FOOD00992)

Tea

Herbal tea

Hibiscus tea (FooDB: FOOD00723)
Greenthread tea (FooDB: FOOD00820)

Baking good

Wrapper

Wonton wrapper (FooDB: FOOD00818)

Beverage

Fermented beverage

Beer (FooDB: FOOD00268)

Abalone (FooDB: FOOD00279)
Conch (FooDB: FOOD00611)

Milk and milk product

Unfermented milk

Milk (Cow) (FooDB: FOOD00618)

Cocoa and cocoa product

Cocoa

Cocoa bean (FooDB: FOOD00182)

Endogenous

Endogenous (HMDB: HMDB0000195)

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Purine Metabolism (HMDB: HMDB0000195)
Adenine and Adenosine Salvage I (PathBank: SMP0002081)
Adenine and Adenosine Salvage II (PathBank: SMP0002083)
Purine Ribonucleosides Degradation (PathBank: SMP0002088)
Adenosine Nucleotides Degradation (PathBank: SMP0002103)
AMP Degradation (Hypoxanthine Route) (PathBank: SMP0012052)

Disease pathway

Purine Nucleoside Phosphorylase Deficiency (HMDB: HMDB0000195)
Xanthinuria Type II (PathBank: SMP0120578)
Gout or Kelley-Seegmiller Syndrome (PathBank: SMP0120709)
Xanthine Dehydrogenase Deficiency (Xanthinuria) (PathBank: SMP0120717)
Mitochondrial DNA Depletion Syndrome (PathBank: SMP0120820)
Adenylosuccinate Lyase Deficiency (PathBank: SMP0120670)
AICA-Ribosiduria (PathBank: SMP0120673)
Adenine Phosphoribosyltransferase Deficiency (APRT) (PathBank: SMP0120819)
Myoadenylate Deaminase Deficiency (PathBank: SMP0120821)
Adenosine Deaminase Deficiency (PathBank: SMP0120448)
Lesch-Nyhan Syndrome (LNS) (PathBank: SMP0120508)
Molybdenum Cofactor Deficiency (PathBank: SMP0120752)
Xanthinuria Type I (PathBank: SMP0120577)
Mitochondrial DNA Depletion Syndrome (PathBank: SMP0000536)

Drug action pathway

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

Role

Biological role

Modulator

Immunomodulator (HMDB: HMDB0000195)

Industrial application

Neuroprotective agent (HMDB: HMDB0000195)

Pharmaceutical industry

Biomarker

Purine nucleoside phosphorylase deficiency (MarkerDB: MDB00000095)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	218 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	15.8 mg/mL	YALKOWSKY,SH & DANNENFELSER,RM (1992)
LogP	-2.10	HANSCH,C ET AL. (1995)

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M-H]-	Astarita_neg	152.7	30932474
[M-H]-	Baker	161.698	30932474
[M-H]-	MetCCS_test_neg	155.7	30932474
[M+H]+	Astarita_pos	153.3	30932474
[M+H]+	Baker	159.251	30932474
[M-H]-	Not Available	158.8	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000151
[M+H]+	Not Available	159.251	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000151

Predicted Molecular 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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	159.828	31661259
DarkChem	[M-H]-	155.669	31661259
AllCCS	[M+H]+	160.057	32859911
AllCCS	[M-H]-	158.368	32859911
DeepCCS	[M-2H]-	186.419	30932474
DeepCCS	[M+Na]+	161.178	30932474
AllCCS	[M+H]+	160.1	32859911
AllCCS	[M+H-H2O]+	156.5	32859911
AllCCS	[M+NH4]+	163.3	32859911
AllCCS	[M+Na]+	164.3	32859911
AllCCS	[M-H]-	158.4	32859911
AllCCS	[M+Na-2H]-	157.9	32859911
AllCCS	[M+HCOO]-	157.4	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Inosine	OC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=NC2=C(O)N=CN=C12	3440.7	Standard polar	33892256
Inosine	OC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=NC2=C(O)N=CN=C12	1834.9	Standard non polar	33892256
Inosine	OC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=NC2=C(O)N=CN=C12	2504.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Inosine,1TMS,isomer #1	C[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC3=C(O)N=CN=C32)[C@H](O)[C@@H]1O	2645.9	Semi standard non polar	33892256
Inosine,1TMS,isomer #2	C[Si](C)(C)O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1C=NC2=C(O)N=CN=C21	2627.9	Semi standard non polar	33892256
Inosine,1TMS,isomer #3	C[Si](C)(C)O[C@@H]1[C@@H](CO)O[C@@H](N2C=NC3=C(O)N=CN=C32)[C@@H]1O	2629.8	Semi standard non polar	33892256
Inosine,1TMS,isomer #4	C[Si](C)(C)OC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O	2559.3	Semi standard non polar	33892256
Inosine,2TMS,isomer #1	C[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC3=C(O[Si](C)(C)C)N=CN=C32)[C@H](O)[C@@H]1O	2550.3	Semi standard non polar	33892256
Inosine,2TMS,isomer #2	C[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC3=C(O)N=CN=C32)[C@H](O[Si](C)(C)C)[C@@H]1O	2623.9	Semi standard non polar	33892256
Inosine,2TMS,isomer #3	C[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC3=C(O)N=CN=C32)[C@H](O)[C@@H]1O[Si](C)(C)C	2616.5	Semi standard non polar	33892256
Inosine,2TMS,isomer #4	C[Si](C)(C)O[C@@H]1[C@@H](CO)O[C@@H](N2C=NC3=C(O)N=CN=C32)[C@@H]1O[Si](C)(C)C	2607.7	Semi standard non polar	33892256
Inosine,2TMS,isomer #5	C[Si](C)(C)OC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O[Si](C)(C)C	2539.4	Semi standard non polar	33892256
Inosine,2TMS,isomer #6	C[Si](C)(C)OC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@H]1O	2544.7	Semi standard non polar	33892256
Inosine,3TMS,isomer #1	C[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC3=C(O[Si](C)(C)C)N=CN=C32)[C@H](O[Si](C)(C)C)[C@@H]1O	2548.7	Semi standard non polar	33892256
Inosine,3TMS,isomer #2	C[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC3=C(O[Si](C)(C)C)N=CN=C32)[C@H](O)[C@@H]1O[Si](C)(C)C	2549.6	Semi standard non polar	33892256
Inosine,3TMS,isomer #3	C[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC3=C(O)N=CN=C32)[C@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C	2569.5	Semi standard non polar	33892256
Inosine,3TMS,isomer #4	C[Si](C)(C)OC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@H]1O[Si](C)(C)C	2540.6	Semi standard non polar	33892256
Inosine,4TMS,isomer #1	C[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC3=C(O[Si](C)(C)C)N=CN=C32)[C@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C	2558.9	Semi standard non polar	33892256
Inosine,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC3=C(O)N=CN=C32)[C@H](O)[C@@H]1O	2897.2	Semi standard non polar	33892256
Inosine,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1C=NC2=C(O)N=CN=C21	2880.9	Semi standard non polar	33892256
Inosine,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H](CO)O[C@@H](N2C=NC3=C(O)N=CN=C32)[C@@H]1O	2876.3	Semi standard non polar	33892256
Inosine,1TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O	2806.5	Semi standard non polar	33892256
Inosine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC3=C(O[Si](C)(C)C(C)(C)C)N=CN=C32)[C@H](O)[C@@H]1O	3015.8	Semi standard non polar	33892256
Inosine,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC3=C(O)N=CN=C32)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O	3091.9	Semi standard non polar	33892256
Inosine,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC3=C(O)N=CN=C32)[C@H](O)[C@@H]1O[Si](C)(C)C(C)(C)C	3091.2	Semi standard non polar	33892256
Inosine,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H](CO)O[C@@H](N2C=NC3=C(O)N=CN=C32)[C@@H]1O[Si](C)(C)C(C)(C)C	3080.0	Semi standard non polar	33892256
Inosine,2TBDMS,isomer #5	CC(C)(C)[Si](C)(C)OC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O[Si](C)(C)C(C)(C)C	2992.7	Semi standard non polar	33892256
Inosine,2TBDMS,isomer #6	CC(C)(C)[Si](C)(C)OC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](CO)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]1O	3000.8	Semi standard non polar	33892256
Inosine,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC3=C(O[Si](C)(C)C(C)(C)C)N=CN=C32)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O	3189.5	Semi standard non polar	33892256
Inosine,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC3=C(O[Si](C)(C)C(C)(C)C)N=CN=C32)[C@H](O)[C@@H]1O[Si](C)(C)C(C)(C)C	3195.5	Semi standard non polar	33892256
Inosine,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC3=C(O)N=CN=C32)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O[Si](C)(C)C(C)(C)C	3214.4	Semi standard non polar	33892256
Inosine,3TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](CO)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]1O[Si](C)(C)C(C)(C)C	3175.2	Semi standard non polar	33892256
Inosine,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC3=C(O[Si](C)(C)C(C)(C)C)N=CN=C32)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O[Si](C)(C)C(C)(C)C	3361.9	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Inosine GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-0frt-0890000000-c0c5ebc2bbf12c1a7edf	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Inosine GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (4 TMS)	splash10-00di-9440000000-566aadb777ee03fb22fb	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Inosine GC-MS (4 TMS)	splash10-0fsi-1690000000-364bf8794afeeff6ba51	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Inosine GC-EI-TOF (Non-derivatized)	splash10-0frt-0890000000-c0c5ebc2bbf12c1a7edf	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Inosine GC-EI-TOF (Non-derivatized)	splash10-00di-9440000000-566aadb777ee03fb22fb	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Inosine GC-MS (Non-derivatized)	splash10-0fsi-1690000000-364bf8794afeeff6ba51	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Inosine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0adl-9250000000-d6ee10ae0804bda3e4ce	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Inosine GC-MS (3 TMS) - 70eV, Positive	splash10-0lmr-8659500000-9f567e118aa09e880541	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Inosine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Inosine GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Inosine GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Inosine GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Inosine GC-MS (TMS_1_4) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Inosine GC-MS (TMS_2_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Inosine GC-MS (TMS_2_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Inosine GC-MS (TMS_2_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Inosine GC-MS (TMS_2_4) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Inosine GC-MS (TMS_2_5) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Inosine GC-MS (TMS_2_6) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Inosine GC-MS (TMS_3_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Inosine GC-MS (TMS_3_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Inosine GC-MS (TMS_3_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Inosine GC-MS (TMS_3_4) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Inosine GC-MS (TMS_4_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Inosine GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Inosine LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative-QTOF	splash10-014r-0490020000-6eeacbf0ca8726ed8542	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Inosine LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative-QTOF	splash10-0006-9100000000-cdcc2e477ba37ca8f07a	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Inosine LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative-QTOF	splash10-001i-0900000000-f96733a8f63a90d3644d	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Inosine LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative-QTOF	splash10-0002-0900000000-b9b05cbee9a42ce87c0f	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Inosine LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative-QTOF	splash10-015i-0696011000-c836d8cd13395c898ae1	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Inosine LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative-QTOF	splash10-0006-9100000000-d8c6fdb9231ac2c6e939	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Inosine LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative-QTOF	splash10-001i-0900000000-632ba91cd477e5aaf9e5	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Inosine LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative-QTOF	splash10-001i-0910000000-fc11279b73334e4ea0a8	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Inosine LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative-QTOF	splash10-014i-0090000000-00981efb4a9571473866	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Inosine LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative-QTOF	splash10-014i-0390000000-989ff580a7b60b151996	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Inosine LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative-QTOF	splash10-000i-0920000000-b78cba83cbf8f1ae48f3	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Inosine LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative-QTOF	splash10-000i-0910000000-505a6507fcb525fe9a14	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Inosine LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative-QTOF	splash10-052r-2900000000-33d1372d34f6b06e3a2f	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Inosine LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative-QTOF	splash10-000i-0930000000-9285a36e16cdf00b3f71	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Inosine LC-ESI-QQ , negative-QTOF	splash10-014i-0090000000-00981efb4a9571473866	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Inosine LC-ESI-QQ , negative-QTOF	splash10-014i-0390000000-989ff580a7b60b151996	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Inosine LC-ESI-QQ , negative-QTOF	splash10-000i-0920000000-b78cba83cbf8f1ae48f3	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Inosine LC-ESI-QQ , negative-QTOF	splash10-000i-0910000000-c6d9b3470f4bf20f2031	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Inosine LC-ESI-QQ , negative-QTOF	splash10-052r-2900000000-33d1372d34f6b06e3a2f	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Inosine LC-ESI-IT , negative-QTOF	splash10-000i-0900000000-cb192ec0941c4e4f04b1	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Inosine LC-ESI-ITFT , negative-QTOF	splash10-0006-9100000000-1b4c3c2319fbba7de36b	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Inosine LC-ESI-ITFT , negative-QTOF	splash10-001i-0900000000-cc8e5ee2239e2de92705	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Inosine LC-ESI-ITFT , negative-QTOF	splash10-0006-9100000000-d8c6fdb9231ac2c6e939	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Inosine LC-ESI-ITFT , negative-QTOF	splash10-001i-0900000000-632ba91cd477e5aaf9e5	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Inosine LC-ESI-QTOF , negative-QTOF	splash10-000i-0930000000-6d3be934cd4b9ed750dd	2017-09-14	HMDB team, MONA	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Experimental 1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	2012-12-04	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Experimental 2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	2012-12-05	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular
Mitochondria
Lysosome

Biospecimen Locations

Blood
Cellular Cytoplasm
Cerebrospinal Fluid (CSF)
Feces
Pericardial Effusion
Saliva
Urine

Tissue Locations

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

Pathways

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

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.20 +/- 0.07 uM	Adult (>18 years old)	Both	Normal	16139832	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Blood	Detected and Quantified	0.05 +/- 0.01 uM	Adult (>18 years old)	Both	Normal	9663253	details
Blood	Detected and Quantified	5.0 +/- 0.8 uM	Adult (>18 years old)	Both	Normal	9607216	details
Blood	Detected and Quantified	0.3 +/- 0.1 uM	Adult (>18 years old)	Both	Normal	8595732	details
Blood	Detected and Quantified	0.9 +/- 0.2 uM	Adult (>18 years old)	Male	normal	3818951	details
Cellular Cytoplasm	Detected and Quantified	1 uM	Adult (>18 years old)	Both	Normal	15882454	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.64 +/- 0.35 uM	Adult (>18 years old)	Both	Normal	8597780	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.6 (0.0-1.2) uM	Newborn (0-30 days old)	Both	Normal	6681617	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	28270806	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	25037050	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	21330412	details
Feces	Detected but not Quantified	Not Quantified	Children (6 - 18 years old)	Not Specified	Normal	27609529	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	29808030	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	27543620	details
Pericardial Effusion	Detected and Quantified	0.347 (0.159 - 1.037) uM	Adult (>18 years old)	Both	Normal	10499868	details
Saliva	Detected and Quantified	0.37 +/- 0.80 uM	Adult (>18 years old)	Both	Normal	Zerihun T. Dame, ...	details
Saliva	Detected and Quantified	0.68 +/- 0.20 uM	Adult (>18 years old)	Both	Normal	11310987	details
Saliva	Detected and Quantified	0.96 +/- 0.23 uM	Adult (>18 years old)	Both	Normal	11310987	details
Saliva	Detected and Quantified	0.73 +/- 0.16 uM	Adult (>18 years old)	Both	Normal	11310987	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Urine	Detected and Quantified	1.653 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Normal	Analysis of 30 no...	details
Urine	Detected and Quantified	0.28 +/- 0.15 umol/mmol creatinine	Adult (>18 years old)	Female	Normal	9129323	details
Urine	Detected and Quantified	0.31 +/- 0.17 umol/mmol creatinine	Adult (>18 years old)	Male	Normal	9129323	details
Urine	Detected and Quantified	0.30 +/- 0.16 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	9129323	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	28157703	details
Urine	Detected and Quantified	0-21 umol/mmol creatinine	Children (1 - 18 years old)	Both	Normal	BC Children's Hos...	details
Urine	Detected and Quantified	0.71 +/- 0.89 umol/mmol creatinine	Children (1-13 years old)	Both	Normal	16139832	details
Urine	Detected and Quantified	0.28 +/- 0.33 umol/mmol creatinine	Adolescent (13-18 years old)	Both	Normal	16139832	details
Urine	Detected and Quantified	1.04 +/- 0.56 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	16139832	details
Urine	Detected and Quantified	1.4 (0.4-6.5) umol/mmol creatinine	Adult (>18 years old)	Both	Normal	24023812	details
Urine	Detected and Quantified	0.59 (0.38-1.00) umol/mmol creatinine	Newborn (0-30 days old)	Both	Normal	Analysis of 40 NI...	details
Urine	Detected and Quantified	0.5 umol/mmol creatinine	Infant (0-1 year old)	Both	Normal	30817767	details
Urine	Detected and Quantified	0-25 umol/mmol creatinine	Newborn (0-30 days old)	Both	Normal	31506554	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.68 +/- 0.47 uM	Adult (>18 years old)	Both	Canavan disease	16139832	details
Blood	Detected and Quantified	0.19 +/- 0.17 uM uM	Adult (>18 years old)	Both	Septic shock	9663253	details
Blood	Detected and Quantified	0.19 +/- 0.17 uM	Adult (>18 years old)	Both	Cardiogenic shock	9663253	details
Blood	Detected and Quantified	0.19 +/- 0.17 uM	Adult (>18 years old)	Both	Major trauma	9663253	details
Blood	Detected and Quantified	30.0 uM	Adult (>18 years old)	Both	Purine nucleoside phosphorylase deficiency	8595732	details
Blood	Detected and Quantified	1.0 +/- 0.5 uM	Adult (>18 years old)	Both	Solid tumors	6736109	details
Blood	Detected and Quantified	0.5 uM	Children (1-13 years old)	Male	Xanthinuria type 1	3818951	details
Blood	Detected and Quantified	0.6 uM	Adult (>18 years old)	Female	Xanthinuria type 1	3818951	details
Blood	Detected and Quantified	1.6 +/- 0.4 uM	Adult (>18 years old)	Both	Kidney disease	9607216	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.70 (0.60-0.80) uM	Adult (>18 years old)	Both	Degenerative disc disease	6656991	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Gout	28270806	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal Cancer	27275383	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Irritable bowel syndrome	21330412	details
Feces	Detected but not Quantified	Not Quantified	Children (6 - 18 years old)	Not Specified	Crohns disease	27609529	details
Feces	Detected but not Quantified	Not Quantified	Children (6 - 18 years old)	Not Specified	Ulcerative colitis	27609529	details
Feces	Detected but not Quantified	Not Quantified	Children (6 - 18 years old)	Not Specified	Unclassified IBD	27609529	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	25037050	details
Pericardial Effusion	Detected and Quantified	0.658 (0.321 - 1.331) uM	Adult (>18 years old)	Both	Coronary artery disease	10499868	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Attachment loss	31026179	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Periodontal Probing Depth	31026179	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Tooth Decay	31026179	details
Urine	Detected and Quantified	2.388 +/- 2.543 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Eosinophilic esophagitis	Analysis of 30 no...	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Bladder cancer	28157703	details
Urine	Detected and Quantified	1.00 +/- 1.61 umol/mmol creatinine	Adult (>18 years old)	Both	Canavan disease	16139832	details
Urine	Detected and Quantified	14000.0 umol/mmol creatinine	Adult (>18 years old)	Both	Purine nucleoside phosphorylase deficiency	8595732	details

Associated Disorders and Diseases

Disease References

Critical illnesses
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 ]
Canavan disease
Tavazzi B, Lazzarino G, Leone P, Amorini AM, Bellia F, Janson CG, Di Pietro V, Ceccarelli L, Donzelli S, Francis JS, Giardina B: Simultaneous high performance liquid chromatographic separation of purines, pyrimidines, N-acetylated amino acids, and dicarboxylic acids for the chemical diagnosis of inborn errors of metabolism. Clin Biochem. 2005 Nov;38(11):997-1008. Epub 2005 Sep 1. [PubMed:16139832 ]
Kidney disease
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 ]
Purine nucleoside phosphorylase deficiency
Chantin C, Bonin B, Boulieu R, Bory C: Liquid-chromatographic study of purine metabolism abnormalities in purine nucleoside phosphorylase deficiency. Clin Chem. 1996 Feb;42(2):326-8. [PubMed:8595732 ]
Thymidine treatment
Leyva A, Schornagel JH, Kraal I, Wadman SK, Pinedo HM: Clinical and biochemical studies of high-dose thymidine treatment in patients with solid tumors. J Cancer Res Clin Oncol. 1984;107(3):211-6. [PubMed:6736109 ]
Septic shock
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 ]
Xanthinuria type 1
Mateos FA, Puig JG, Jimenez ML, Fox IH: Hereditary xanthinuria. Evidence for enhanced hypoxanthine salvage. J Clin Invest. 1987 Mar;79(3):847-52. [PubMed:3818951 ]
Degenerative disc disease
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 ]
Irritable bowel syndrome
Ponnusamy K, Choi JN, Kim J, Lee SY, Lee CH: Microbial community and metabolomic comparison of irritable bowel syndrome faeces. J Med Microbiol. 2011 Jun;60(Pt 6):817-27. doi: 10.1099/jmm.0.028126-0. Epub 2011 Feb 17. [PubMed:21330412 ]
Colorectal cancer
Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ] Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
Crohn's disease
Kolho KL, Pessia A, Jaakkola T, de Vos WM, Velagapudi V: Faecal and Serum Metabolomics in Paediatric Inflammatory Bowel Disease. J Crohns Colitis. 2017 Mar 1;11(3):321-334. doi: 10.1093/ecco-jcc/jjw158. [PubMed:27609529 ]
Ulcerative colitis
Kolho KL, Pessia A, Jaakkola T, de Vos WM, Velagapudi V: Faecal and Serum Metabolomics in Paediatric Inflammatory Bowel Disease. J Crohns Colitis. 2017 Mar 1;11(3):321-334. doi: 10.1093/ecco-jcc/jjw158. [PubMed:27609529 ]
Gout
Shao T, Shao L, Li H, Xie Z, He Z, Wen C: Combined Signature of the Fecal Microbiome and Metabolome in Patients with Gout. Front Microbiol. 2017 Feb 21;8:268. doi: 10.3389/fmicb.2017.00268. eCollection 2017. [PubMed:28270806 ]
Coronary artery disease
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 ]
Attachment loss
Liebsch C, Pitchika V, Pink C, Samietz S, Kastenmuller G, Artati A, Suhre K, Adamski J, Nauck M, Volzke H, Friedrich N, Kocher T, Holtfreter B, Pietzner M: The Saliva Metabolome in Association to Oral Health Status. J Dent Res. 2019 Jun;98(6):642-651. doi: 10.1177/0022034519842853. Epub 2019 Apr 26. [PubMed:31026179 ]
Periodontal Probing Depth
Liebsch C, Pitchika V, Pink C, Samietz S, Kastenmuller G, Artati A, Suhre K, Adamski J, Nauck M, Volzke H, Friedrich N, Kocher T, Holtfreter B, Pietzner M: The Saliva Metabolome in Association to Oral Health Status. J Dent Res. 2019 Jun;98(6):642-651. doi: 10.1177/0022034519842853. Epub 2019 Apr 26. [PubMed:31026179 ]
Tooth Decay
Liebsch C, Pitchika V, Pink C, Samietz S, Kastenmuller G, Artati A, Suhre K, Adamski J, Nauck M, Volzke H, Friedrich N, Kocher T, Holtfreter B, Pietzner M: The Saliva Metabolome in Association to Oral Health Status. J Dent Res. 2019 Jun;98(6):642-651. doi: 10.1177/0022034519842853. Epub 2019 Apr 26. [PubMed:31026179 ]
Eosinophilic esophagitis
Slae, M., Huynh, H., Wishart, D.S. (2014). Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work). NA.

Associated OMIM IDs

271900 (Canavan disease)
164050 (Purine nucleoside phosphorylase deficiency )
278300 (Xanthinuria type 1)
114500 (Colorectal cancer)
266600 (Crohn's disease)
138900 (Gout)
610247 (Eosinophilic esophagitis)

External Links

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

VMH ID

INS

MarkerDB ID

MDB00000095

Good Scents ID

Not Available

References

Synthesis Reference

Shi, Qingshan; Qiu, Yutang; Li, Liangqiu; Lin, Xiaoping. New inosine-producing bacterium and method for producing inosine. Faming Zhuanli Shenqing Gongkai Shuomingshu (2003), 6 pp.

Material Safety Data Sheet (MSDS)

Download (PDF)

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 ]
Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]
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 ]

Only showing the first 10 proteins. There are 13 proteins in total.

Show all enzymes and transporters

Enzymes

Enzyme Details

1. 5'-nucleotidase

General function:: Involved in hydrolase activity
Specific function:: Hydrolyzes extracellular nucleotides into membrane permeable nucleosides.
Gene Name:: NT5E
Uniprot ID:: P21589
Molecular weight:: 57948.125

Reactions

Inosinic acid + Water → Inosine + Phosphate	details

Enzyme Details

2. Cytosolic 5'-nucleotidase 1B

General function:: Involved in nucleotide binding
Specific function:: Dephosphorylates the 5' and 2'(3')-phosphates of deoxyribonucleotides. Helps to regulate adenosine levels (By similarity).
Gene Name:: NT5C1B
Uniprot ID:: Q96P26
Molecular weight:: 68803.055

Reactions

Inosinic acid + Water → Inosine + Phosphate	details

Enzyme Details

3. Cytosolic 5'-nucleotidase 1A

General function:: Involved in nucleotide binding
Specific function:: Dephosphorylates the 5' and 2'(3')-phosphates of deoxyribonucleotides and has a broad substrate specificity. Helps to regulate adenosine levels in heart during ischemia and hypoxia.
Gene Name:: NT5C1A
Uniprot ID:: Q9BXI3
Molecular weight:: 41020.145

Reactions

Inosinic acid + Water → Inosine + Phosphate	details

Enzyme Details

4. 5'(3')-deoxyribonucleotidase, cytosolic type

General function:: Involved in metal ion binding
Specific function:: Dephosphorylates the 5' and 2'(3')-phosphates of deoxyribonucleotides, with a preference for dUMP and dTMP, intermediate activity towards dGMP, and low activity towards dCMP and dAMP.
Gene Name:: NT5C
Uniprot ID:: Q8TCD5
Molecular weight:: Not Available

Reactions

Inosinic acid + Water → Inosine + Phosphate	details

Enzyme Details

5. 5'(3')-deoxyribonucleotidase, mitochondrial

General function:: Involved in phosphatase activity
Specific function:: Dephosphorylates specifically the 5' and 2'(3')-phosphates of uracil and thymine deoxyribonucleotides, and so protects mitochondrial DNA replication from excess dTTP. Has only marginal activity towards dIMP and dGMP.
Gene Name:: NT5M
Uniprot ID:: Q9NPB1
Molecular weight:: Not Available

Reactions

Inosinic acid + Water → Inosine + Phosphate	details

Enzyme Details

6. Xanthine dehydrogenase/oxidase

General function:: Involved in oxidoreductase activity
Specific function:: Key enzyme in purine degradation. Catalyzes the oxidation of hypoxanthine to xanthine. Catalyzes the oxidation of xanthine to uric acid. Contributes to the generation of reactive oxygen species. Has also low oxidase activity towards aldehydes (in vitro).
Gene Name:: XDH
Uniprot ID:: P47989
Molecular weight:: 146422.99

References

STIRPE F, DELLACORTE E: REGULATION OF XANTHINE DEHYDROGENASE IN CHICK LIVER. EFFECT OF STARVATION AND OF ADMINISTRATION OF PURINES AND PURINE NUCLEOSIDES. Biochem J. 1965 Feb;94:309-13. [PubMed:14348191 ]

Enzyme Details

7. Adenosine deaminase

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

Reactions

Adenosine + Water → Inosine + Ammonia	details

Enzyme Details

8. Equilibrative nucleoside transporter 4

General function:: Involved in nucleoside transmembrane transporter activity
Specific function:: Functions as a polyspecific organic cation transporter, efficiently transporting many organic cations such as monoamine neurotransmitters 1-methyl-4-phenylpyridinium and biogenic amines including serotonin, dopamine, norepinephrine and epinephrine. May play a role in regulating central nervous system homeostasis of monoamine neurotransmitters. May be involved in luminal transport of organic cations in the kidney and seems to use luminal proton gradient to drive organic cation reabsorption. Does not seem to transport nucleoside and nucleoside analogs such as uridine, cytidine, thymidine, adenosine, inosine, guanosine, and azidothymidine. In (PubMed:16873718) adenosine is efficiently transported but in a fashion highly sensitive to extracellular pH, with maximal activity in the pH range 5.5 to 6.5. Glu-206 is essential for the cation selectivity and may function as the charge sensor for cationic substrates. Transport is chloride and sodium-independent but appears to be sensitive to changes in membrane potential. Weakly inhibited by the classical inhibitors of equilibrative nucleoside transport, dipyridamole, dilazep, and nitrobenzylthioinosine. May play a role in the regulation of extracellular adenosine concentrations in cardiac tissues, in particular during ischemia
Gene Name:: SLC29A4
Uniprot ID:: Q7RTT9
Molecular weight:: 58058.0

Enzyme Details

9. Cytosolic 5'-nucleotidase 3

General function:: Involved in magnesium ion binding
Specific function:: Can act both as nucleotidase and as phosphotransferase.
Gene Name:: NT5C3
Uniprot ID:: Q9H0P0
Molecular weight:: 33914.91

Reactions

Inosinic acid + Water → Inosine + Phosphate	details

Enzyme Details

10. Cytosolic purine 5'-nucleotidase

General function:: Involved in 5'-nucleotidase activity
Specific function:: May have a critical role in the maintenance of a constant composition of intracellular purine/pyrimidine nucleotides in cooperation with other nucleotidases. Preferentially hydrolyzes inosine 5'-monophosphate (IMP) and other purine nucleotides.
Gene Name:: NT5C2
Uniprot ID:: P49902
Molecular weight:: 64969.2

Reactions

Inosinic acid + Water → Inosine + Phosphate	details

Only showing the first 10 proteins. There are 13 proteins in total.

Show all enzymes and transporters

Showing metabocard for Inosine (HMDB0000195)

MOL for HMDB0000195 (Inosine)

3D MOL for HMDB0000195 (Inosine)

3D SDF for HMDB0000195 (Inosine)

3D-SDF for HMDB0000195 (Inosine)

PDB for HMDB0000195 (Inosine)

3D PDB for HMDB0000195 (Inosine)

SMILES for HMDB0000195 (Inosine)

INCHI for HMDB0000195 (Inosine)

Structure for HMDB0000195 (Inosine)

3D Structure for HMDB0000195 (Inosine)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes

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References

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