Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (9) Show 9 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 20:55:57 UTC

HMDB ID

HMDB0000299

Secondary Accession Numbers

HMDB00299

Metabolite Identification

Common Name

Xanthosine

Description

Xanthosine, also known as xanthine riboside, 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. Xanthosine is a nucleoside derived from xanthine and ribose. Xanthosine exists in all living species, ranging from bacteria to plants to humans. In plants xanthosine is the biosynthetic precursor to 7-methylxanthosine which is produced by the action of the enzyme known as 7-methylxanthosine synthase. 7-Methylxanthosine in turn is the precursor to theobromine (the active alkaloid in chocolate), which in turn is the precursor to caffeine, the active alkaloid in coffee and tea. Within humans, xanthosine participates in a number of enzymatic reactions. In particular, xanthosine can be biosynthesized from xanthylic acid; which is catalyzed by the enzyme cytosolic purine 5'-nucleotidase. In addition, xanthosine can be converted into xanthine and ribose 1-phosphate; which is mediated by the enzyme purine nucleoside phosphorylase. Xanthosine monophosphate (XMP) is an intermediate in purine metabolism, formed from IMP (inosine monophosphate).

Structure

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

HMDB0000299
     RDKit          3D
Xanthosine
 32 34  0  0  0  0  0  0  0  0999 V2000
   -5.0067    0.4182    0.1166 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9402   -0.2156    0.7502 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6340    0.5263    0.4664 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5702   -0.0814    1.0815 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4917    0.1380    0.2334 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6755   -0.5961    0.5811 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8007   -1.7835    1.1745 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1211   -2.1026    1.3116 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8486   -1.0749    0.7835 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2002   -0.8491    0.6468 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1407   -1.7532    1.0839 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6152    0.2873    0.0696 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7473    1.1878   -0.3669 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1602    2.3705   -0.9673 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4307    0.9588   -0.2292 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9353   -0.1662    0.3436 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0880   -0.2610   -1.1025 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3057    0.1663   -2.1617 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4024    0.4887   -1.0189 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1694    1.7656   -1.5303 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3116   -0.1290   -0.6555 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8044   -1.2496    0.3711 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1719   -0.2265    1.8297 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6865    1.5764    0.8417 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3244    1.2413    0.1944 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0432   -2.3859    1.4913 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4603   -1.8406    2.0276 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7331    2.7399   -1.8119 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2653   -1.3672   -1.1357 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6039   -0.1954   -2.0099 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2100   -0.0297   -1.5692 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0472    2.4422   -0.8396 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
 13 15  1  0
 15 16  2  0
  5 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 19  3  1  0
 16  6  1  0
 16  9  1  0
  1 21  1  0
  2 22  1  0
  2 23  1  0
  3 24  1  1
  5 25  1  6
  7 26  1  0
 11 27  1  0
 14 28  1  0
 17 29  1  1
 18 30  1  0
 19 31  1  6
 20 32  1  0
M  END

Xanthosine 5'-triphosphate.mol
  Mrv1652309042000002D          

 20 22  0  0  0  0            999 V2000
    3.0342    0.5318    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2373    0.7453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6853    0.1322    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8568   -0.6748    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6105   -1.0103    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1424   -1.0873    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0561   -1.9078    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5293   -0.5352    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8648    0.2184    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2777   -0.7068    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6133   -1.4604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4337   -1.3742    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6053   -0.5672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3197   -0.1547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0342   -0.5672    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3197    0.6703    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6053    1.0828    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6053    1.9078    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8908    0.6703    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8908   -0.1547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  2  1  6  0  0  0
  3  4  1  0  0  0  0
  4  5  1  1  0  0  0
  4  6  1  0  0  0  0
  6  7  1  1  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  3  9  1  0  0  0  0
  8 10  1  6  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  2  0  0  0  0
 19 20  1  0  0  0  0
 13 20  2  0  0  0  0
 10 20  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0000299

> <DATABASE_NAME>
hmdb

> <SMILES>
OC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=NC2=C1N=C(O)N=C2O

> <INCHI_IDENTIFIER>
InChI=1S/C10H12N4O6/c15-1-3-5(16)6(17)9(20-3)14-2-11-4-7(14)12-10(19)13-8(4)18/h2-3,5-6,9,15-17H,1H2,(H2,12,13,18,19)/t3-,5-,6-,9-/m1/s1

> <INCHI_KEY>
UBORTCNDUKBEOP-UUOKFMHZSA-N

> <FORMULA>
C10H12N4O6

> <MOLECULAR_WEIGHT>
284.2255

> <EXACT_MASS>
284.075684136

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
32

> <JCHEM_AVERAGE_POLARIZABILITY>
25.54856291933196

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
-1.60

> <JCHEM_LOGP>
-1.1903825390000002

> <ALOGPS_LOGS>
-1.01

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.473029142968798

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.331641933271216

> <JCHEM_PKA_STRONGEST_BASIC>
0.07830393650019773

> <JCHEM_POLAR_SURFACE_AREA>
153.98000000000002

> <JCHEM_REFRACTIVITY>
62.40299999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.78e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]purine-2,6-diol

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0000299
     RDKit          3D
Xanthosine
 32 34  0  0  0  0  0  0  0  0999 V2000
   -5.0067    0.4182    0.1166 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9402   -0.2156    0.7502 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6340    0.5263    0.4664 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5702   -0.0814    1.0815 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4917    0.1380    0.2334 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6755   -0.5961    0.5811 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8007   -1.7835    1.1745 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1211   -2.1026    1.3116 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8486   -1.0749    0.7835 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2002   -0.8491    0.6468 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1407   -1.7532    1.0839 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6152    0.2873    0.0696 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7473    1.1878   -0.3669 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1602    2.3705   -0.9673 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4307    0.9588   -0.2292 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9353   -0.1662    0.3436 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0880   -0.2610   -1.1025 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3057    0.1663   -2.1617 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4024    0.4887   -1.0189 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1694    1.7656   -1.5303 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3116   -0.1290   -0.6555 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8044   -1.2496    0.3711 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1719   -0.2265    1.8297 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6865    1.5764    0.8417 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3244    1.2413    0.1944 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0432   -2.3859    1.4913 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4603   -1.8406    2.0276 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7331    2.7399   -1.8119 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2653   -1.3672   -1.1357 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6039   -0.1954   -2.0099 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2100   -0.0297   -1.5692 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0472    2.4422   -0.8396 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
 13 15  1  0
 15 16  2  0
  5 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 19  3  1  0
 16  6  1  0
 16  9  1  0
  1 21  1  0
  2 22  1  0
  2 23  1  0
  3 24  1  1
  5 25  1  6
  7 26  1  0
 11 27  1  0
 14 28  1  0
 17 29  1  1
 18 30  1  0
 19 31  1  6
 20 32  1  0
M  END

HEADER    PROTEIN                                 04-SEP-20   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: Xanthosine 5'-triphosphate.mol                    
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-20         0                                  
HETATM    1  O   UNK     0       5.664   0.993   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       4.176   1.391   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.146   0.247   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.466  -1.260   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       4.873  -1.886   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       2.132  -2.030   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       1.971  -3.561   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       0.988  -0.999   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       1.614   0.408   0.000  0.00  0.00           O+0
HETATM   10  N   UNK     0      -0.518  -1.319   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0      -1.145  -2.726   0.000  0.00  0.00           C+0
HETATM   12  N   UNK     0      -2.676  -2.565   0.000  0.00  0.00           N+0
HETATM   13  C   UNK     0      -2.997  -1.059   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -4.330  -0.289   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -5.664  -1.059   0.000  0.00  0.00           O+0
HETATM   16  N   UNK     0      -4.330   1.251   0.000  0.00  0.00           N+0
HETATM   17  C   UNK     0      -2.997   2.021   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -2.997   3.561   0.000  0.00  0.00           O+0
HETATM   19  N   UNK     0      -1.663   1.251   0.000  0.00  0.00           N+0
HETATM   20  C   UNK     0      -1.663  -0.289   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    9                                                  
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   10                                                  
CONECT    9    8    3                                                       
CONECT   10    8   11   20                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   20                                                  
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19   13   10                                                  
MASTER        0    0    0    0    0    0    0    0   20    0   44    0
END

COMPND    HMDB0000299
HETATM    1  O1  UNL     1      -5.007   0.418   0.117  1.00  0.00           O  
HETATM    2  C1  UNL     1      -3.940  -0.216   0.750  1.00  0.00           C  
HETATM    3  C2  UNL     1      -2.634   0.526   0.466  1.00  0.00           C  
HETATM    4  O2  UNL     1      -1.570  -0.081   1.081  1.00  0.00           O  
HETATM    5  C3  UNL     1      -0.492   0.138   0.233  1.00  0.00           C  
HETATM    6  N1  UNL     1       0.676  -0.596   0.581  1.00  0.00           N  
HETATM    7  C4  UNL     1       0.801  -1.783   1.175  1.00  0.00           C  
HETATM    8  N2  UNL     1       2.121  -2.103   1.312  1.00  0.00           N  
HETATM    9  C5  UNL     1       2.849  -1.075   0.784  1.00  0.00           C  
HETATM   10  C6  UNL     1       4.200  -0.849   0.647  1.00  0.00           C  
HETATM   11  O3  UNL     1       5.141  -1.753   1.084  1.00  0.00           O  
HETATM   12  N3  UNL     1       4.615   0.287   0.070  1.00  0.00           N  
HETATM   13  C7  UNL     1       3.747   1.188  -0.367  1.00  0.00           C  
HETATM   14  O4  UNL     1       4.160   2.370  -0.967  1.00  0.00           O  
HETATM   15  N4  UNL     1       2.431   0.959  -0.229  1.00  0.00           N  
HETATM   16  C8  UNL     1       1.935  -0.166   0.344  1.00  0.00           C  
HETATM   17  C9  UNL     1      -1.088  -0.261  -1.103  1.00  0.00           C  
HETATM   18  O5  UNL     1      -0.306   0.166  -2.162  1.00  0.00           O  
HETATM   19  C10 UNL     1      -2.402   0.489  -1.019  1.00  0.00           C  
HETATM   20  O6  UNL     1      -2.169   1.766  -1.530  1.00  0.00           O  
HETATM   21  H1  UNL     1      -5.312  -0.129  -0.655  1.00  0.00           H  
HETATM   22  H2  UNL     1      -3.804  -1.250   0.371  1.00  0.00           H  
HETATM   23  H3  UNL     1      -4.172  -0.227   1.830  1.00  0.00           H  
HETATM   24  H4  UNL     1      -2.687   1.576   0.842  1.00  0.00           H  
HETATM   25  H5  UNL     1      -0.324   1.241   0.194  1.00  0.00           H  
HETATM   26  H6  UNL     1      -0.043  -2.386   1.491  1.00  0.00           H  
HETATM   27  H7  UNL     1       5.460  -1.841   2.028  1.00  0.00           H  
HETATM   28  H8  UNL     1       3.733   2.740  -1.812  1.00  0.00           H  
HETATM   29  H9  UNL     1      -1.265  -1.367  -1.136  1.00  0.00           H  
HETATM   30  H10 UNL     1       0.604  -0.195  -2.010  1.00  0.00           H  
HETATM   31  H11 UNL     1      -3.210  -0.030  -1.569  1.00  0.00           H  
HETATM   32  H12 UNL     1      -2.047   2.442  -0.840  1.00  0.00           H  
CONECT    1    2   21
CONECT    2    3   22   23
CONECT    3    4   19   24
CONECT    4    5
CONECT    5    6   17   25
CONECT    6    7   16
CONECT    7    8    8   26
CONECT    8    9
CONECT    9   10   10   16
CONECT   10   11   12
CONECT   11   27
CONECT   12   13   13
CONECT   13   14   15
CONECT   14   28
CONECT   15   16   16
CONECT   17   18   19   29
CONECT   18   30
CONECT   19   20   31
CONECT   20   32
END

HMDB0000299
     RDKit          3D
Xanthosine
 32 34  0  0  0  0  0  0  0  0999 V2000
   -5.0067    0.4182    0.1166 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9402   -0.2156    0.7502 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6340    0.5263    0.4664 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5702   -0.0814    1.0815 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4917    0.1380    0.2334 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6755   -0.5961    0.5811 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8007   -1.7835    1.1745 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1211   -2.1026    1.3116 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8486   -1.0749    0.7835 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2002   -0.8491    0.6468 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1407   -1.7532    1.0839 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6152    0.2873    0.0696 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7473    1.1878   -0.3669 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1602    2.3705   -0.9673 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4307    0.9588   -0.2292 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9353   -0.1662    0.3436 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0880   -0.2610   -1.1025 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3057    0.1663   -2.1617 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4024    0.4887   -1.0189 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1694    1.7656   -1.5303 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3116   -0.1290   -0.6555 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8044   -1.2496    0.3711 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1719   -0.2265    1.8297 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6865    1.5764    0.8417 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3244    1.2413    0.1944 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0432   -2.3859    1.4913 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4603   -1.8406    2.0276 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7331    2.7399   -1.8119 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2653   -1.3672   -1.1357 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6039   -0.1954   -2.0099 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2100   -0.0297   -1.5692 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0472    2.4422   -0.8396 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
 13 15  1  0
 15 16  2  0
  5 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 19  3  1  0
 16  6  1  0
 16  9  1  0
  1 21  1  0
  2 22  1  0
  2 23  1  0
  3 24  1  1
  5 25  1  6
  7 26  1  0
 11 27  1  0
 14 28  1  0
 17 29  1  1
 18 30  1  0
 19 31  1  6
 20 32  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
9-beta-D-Ribofuranosyl-3,9-dihydro-1H-purine-2,6-dione	ChEBI
9-beta-D-Ribofuranosylxanthine	ChEBI
Xanthine 9-beta-D-ribofuranoside	ChEBI
Xanthine riboside	ChEBI
9-b-D-Ribofuranosyl-3,9-dihydro-1H-purine-2,6-dione	Generator
9-Β-D-ribofuranosyl-3,9-dihydro-1H-purine-2,6-dione	Generator
9-b-D-Ribofuranosylxanthine	Generator
9-Β-D-ribofuranosylxanthine	Generator
Xanthine 9-b-D-ribofuranoside	Generator
Xanthine 9-β-D-ribofuranoside	Generator
3,9-Dihydro-9-b-D-ribofuranosyl-1H-purine-2,6-dione	HMDB
3,9-Dihydro-9-beta-delta-ribofuranosyl-1H-purine-2,6-dione	HMDB
3,9-Dihydro-9-D-ribofuranosyl-1H-purine-2,6-dione	HMDB
3,9-Dihydro-9-delta-ribofuranosyl-1H-purine-2,6-dione	HMDB
9-beta-delta-Ribofuranosylxanthine	HMDB
9-D-Ribofuranosylxanthine	HMDB
9-delta-Ribofuranosylxanthine	HMDB
9 beta-D-Ribofuranosylxanthine	HMDB

Chemical Formula

C₁₀H₁₂N₄O₆

Average Molecular Weight

284.2255

Monoisotopic Molecular Weight

284.075684136

IUPAC Name

9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-9H-purine-2,6-diol

Traditional Name

9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]purine-2,6-diol

CAS Registry Number

146-80-5

SMILES

OC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=NC2=C1N=C(O)N=C2O

InChI Identifier

InChI=1S/C10H12N4O6/c15-1-3-5(16)6(17)9(20-3)14-2-11-4-7(14)12-10(19)13-8(4)18/h2-3,5-6,9,15-17H,1H2,(H2,12,13,18,19)/t3-,5-,6-,9-/m1/s1

InChI Key

UBORTCNDUKBEOP-UUOKFMHZSA-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
Xanthine
6-oxopurine
Purinone
Pentose monosaccharide
Purine
Imidazopyrimidine
Alkaloid or derivatives
Pyrimidone
Pyrimidine
Monosaccharide
N-substituted imidazole
Imidazole
Heteroaromatic compound
Tetrahydrofuran
Azole
Vinylogous amide
Lactam
Urea
Secondary alcohol
Organoheterocyclic compound
Azacycle
Oxacycle
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Alcohol
Primary alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

xanthosines (CHEBI:18107 )
Purine alkaloids (C01762 )

Ontology

Physiological effect

Health effect

Digestive system disorder

Hepatobiliary disorder

Hepatic disorder

Liver damage (PMID: 31434538)

Nervous system disorder

Nerve damage (PMID: 31434538)

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 16139832)

Organ

Placenta (HMDB: HMDB0000299)

Excreta

Biofluid or Excreta

Urine (PMID: 9129323)
Feces (PMID: 27609529)

Cellular substructure

Cytoplasm (HMDB: HMDB0000299)

Source

Endogenous

Endogenous (HMDB: HMDB0000299)

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

Other fruit

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

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)

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)

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

Cocoa and cocoa product

Cocoa

Cocoa bean (FooDB: FOOD00182)

Process

Naturally occurring process

Biological process

Biochemical pathway

Disease pathway

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)
Purine Nucleoside Phosphorylase Deficiency (PathBank: SMP0120756)
Adenine Phosphoribosyltransferase Deficiency (APRT) (PathBank: SMP0120819)
Myoadenylate Deaminase Deficiency (PathBank: SMP0120821)
Lesch-Nyhan Syndrome (LNS) (PathBank: SMP0120508)
Molybdenum Cofactor Deficiency (PathBank: SMP0120752)
Adenosine Deaminase Deficiency (PathBank: SMP0120448)
Xanthinuria Type I (PathBank: SMP0120577)
Mitochondrial DNA Depletion Syndrome (PathBank: SMP0000536)

Metabolic pathway

Purine Metabolism (PathBank: SMP0063668)
Purine Ribonucleosides Degradation (PathBank: SMP0002088)

Drug action pathway

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

Role

Biological role

Waste product (PMID: 35448883)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M-H]-	Astarita_neg	154.0	30932474
[M-H]-	Baker	161.363	30932474
[M+H]+	Astarita_pos	157.7	30932474
[M+H]+	Baker	166.49	30932474
[M-H]-	Not Available	159.6	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000156
[M+H]+	Not Available	163.6	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000156

Predicted Molecular Properties

Property	Value	Source
Water Solubility	27.8 g/L	ALOGPS
logP	-1.6	ALOGPS
logP	-1.2	ChemAxon
logS	-1	ALOGPS
pKa (Strongest Acidic)	11.33	ChemAxon
pKa (Strongest Basic)	0.078	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	153.98 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	62.4 m³·mol⁻¹	ChemAxon
Polarizability	25.55 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]+	163.363	31661259
DarkChem	[M-H]-	159.483	31661259
AllCCS	[M+H]+	163.046	32859911
AllCCS	[M-H]-	160.531	32859911
DeepCCS	[M+H]+	154.154	30932474
DeepCCS	[M-H]-	151.759	30932474
DeepCCS	[M-2H]-	185.775	30932474
DeepCCS	[M+Na]+	160.63	30932474
AllCCS	[M+H]+	163.0	32859911
AllCCS	[M+H-H2O]+	159.6	32859911
AllCCS	[M+NH4]+	166.2	32859911
AllCCS	[M+Na]+	167.1	32859911
AllCCS	[M-H]-	160.5	32859911
AllCCS	[M+Na-2H]-	160.0	32859911
AllCCS	[M+HCOO]-	159.5	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Xanthosine	OC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=NC2=C1N=C(O)N=C2O	3692.7	Standard polar	33892256
Xanthosine	OC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=NC2=C1N=C(O)N=C2O	1866.2	Standard non polar	33892256
Xanthosine	OC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=NC2=C1N=C(O)N=C2O	2650.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Xanthosine,1TMS,isomer #1	C[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC3=C(O)N=C(O)N=C32)[C@H](O)[C@@H]1O	2938.4	Semi standard non polar	33892256
Xanthosine,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=C(O)N=C21	2942.9	Semi standard non polar	33892256
Xanthosine,1TMS,isomer #3	C[Si](C)(C)O[C@@H]1[C@@H](CO)O[C@@H](N2C=NC3=C(O)N=C(O)N=C32)[C@@H]1O	2927.6	Semi standard non polar	33892256
Xanthosine,1TMS,isomer #4	C[Si](C)(C)OC1=NC(O)=C2N=CN([C@@H]3O[C@H](CO)[C@@H](O)[C@H]3O)C2=N1	2840.6	Semi standard non polar	33892256
Xanthosine,1TMS,isomer #5	C[Si](C)(C)OC1=NC(O)=NC2=C1N=CN2[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O	2802.6	Semi standard non polar	33892256
Xanthosine,2TMS,isomer #1	C[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC3=C(O[Si](C)(C)C)N=C(O)N=C32)[C@H](O)[C@@H]1O	2777.1	Semi standard non polar	33892256
Xanthosine,2TMS,isomer #10	C[Si](C)(C)OC1=NC(O[Si](C)(C)C)=C2N=CN([C@@H]3O[C@H](CO)[C@@H](O)[C@H]3O)C2=N1	2707.5	Semi standard non polar	33892256
Xanthosine,2TMS,isomer #2	C[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC3=C(O)N=C(O[Si](C)(C)C)N=C32)[C@H](O)[C@@H]1O	2802.9	Semi standard non polar	33892256
Xanthosine,2TMS,isomer #3	C[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC3=C(O)N=C(O)N=C32)[C@H](O[Si](C)(C)C)[C@@H]1O	2917.7	Semi standard non polar	33892256
Xanthosine,2TMS,isomer #4	C[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC3=C(O)N=C(O)N=C32)[C@H](O)[C@@H]1O[Si](C)(C)C	2899.7	Semi standard non polar	33892256
Xanthosine,2TMS,isomer #5	C[Si](C)(C)O[C@@H]1[C@@H](CO)O[C@@H](N2C=NC3=C(O)N=C(O)N=C32)[C@@H]1O[Si](C)(C)C	2902.2	Semi standard non polar	33892256
Xanthosine,2TMS,isomer #6	C[Si](C)(C)OC1=NC(O)=NC2=C1N=CN2[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O[Si](C)(C)C	2783.0	Semi standard non polar	33892256
Xanthosine,2TMS,isomer #7	C[Si](C)(C)OC1=NC(O)=C2N=CN([C@@H]3O[C@H](CO)[C@@H](O)[C@H]3O[Si](C)(C)C)C2=N1	2810.1	Semi standard non polar	33892256
Xanthosine,2TMS,isomer #8	C[Si](C)(C)OC1=NC(O)=NC2=C1N=CN2[C@@H]1O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@H]1O	2771.3	Semi standard non polar	33892256
Xanthosine,2TMS,isomer #9	C[Si](C)(C)OC1=NC(O)=C2N=CN([C@@H]3O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@H]3O)C2=N1	2793.7	Semi standard non polar	33892256
Xanthosine,3TMS,isomer #1	C[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC3=C(O[Si](C)(C)C)N=C(O[Si](C)(C)C)N=C32)[C@H](O)[C@@H]1O	2687.0	Semi standard non polar	33892256
Xanthosine,3TMS,isomer #10	C[Si](C)(C)OC1=NC(O[Si](C)(C)C)=C2N=CN([C@@H]3O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@H]3O)C2=N1	2703.5	Semi standard non polar	33892256
Xanthosine,3TMS,isomer #2	C[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC3=C(O[Si](C)(C)C)N=C(O)N=C32)[C@H](O[Si](C)(C)C)[C@@H]1O	2701.4	Semi standard non polar	33892256
Xanthosine,3TMS,isomer #3	C[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC3=C(O[Si](C)(C)C)N=C(O)N=C32)[C@H](O)[C@@H]1O[Si](C)(C)C	2689.3	Semi standard non polar	33892256
Xanthosine,3TMS,isomer #4	C[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC3=C(O)N=C(O[Si](C)(C)C)N=C32)[C@H](O[Si](C)(C)C)[C@@H]1O	2749.9	Semi standard non polar	33892256
Xanthosine,3TMS,isomer #5	C[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC3=C(O)N=C(O[Si](C)(C)C)N=C32)[C@H](O)[C@@H]1O[Si](C)(C)C	2737.2	Semi standard non polar	33892256
Xanthosine,3TMS,isomer #6	C[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC3=C(O)N=C(O)N=C32)[C@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C	2853.1	Semi standard non polar	33892256
Xanthosine,3TMS,isomer #7	C[Si](C)(C)OC1=NC(O)=NC2=C1N=CN2[C@@H]1O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@H]1O[Si](C)(C)C	2694.2	Semi standard non polar	33892256
Xanthosine,3TMS,isomer #8	C[Si](C)(C)OC1=NC(O)=C2N=CN([C@@H]3O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@H]3O[Si](C)(C)C)C2=N1	2736.2	Semi standard non polar	33892256
Xanthosine,3TMS,isomer #9	C[Si](C)(C)OC1=NC(O[Si](C)(C)C)=C2N=CN([C@@H]3O[C@H](CO)[C@@H](O)[C@H]3O[Si](C)(C)C)C2=N1	2699.1	Semi standard non polar	33892256
Xanthosine,4TMS,isomer #1	C[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC3=C(O[Si](C)(C)C)N=C(O[Si](C)(C)C)N=C32)[C@H](O[Si](C)(C)C)[C@@H]1O	2709.0	Semi standard non polar	33892256
Xanthosine,4TMS,isomer #2	C[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC3=C(O[Si](C)(C)C)N=C(O[Si](C)(C)C)N=C32)[C@H](O)[C@@H]1O[Si](C)(C)C	2700.1	Semi standard non polar	33892256
Xanthosine,4TMS,isomer #3	C[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC3=C(O[Si](C)(C)C)N=C(O)N=C32)[C@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C	2662.3	Semi standard non polar	33892256
Xanthosine,4TMS,isomer #4	C[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC3=C(O)N=C(O[Si](C)(C)C)N=C32)[C@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C	2717.8	Semi standard non polar	33892256
Xanthosine,4TMS,isomer #5	C[Si](C)(C)OC1=NC(O[Si](C)(C)C)=C2N=CN([C@@H]3O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@H]3O[Si](C)(C)C)C2=N1	2710.5	Semi standard non polar	33892256
Xanthosine,5TMS,isomer #1	C[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC3=C(O[Si](C)(C)C)N=C(O[Si](C)(C)C)N=C32)[C@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C	2737.5	Semi standard non polar	33892256
Xanthosine,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC3=C(O)N=C(O)N=C32)[C@H](O)[C@@H]1O	3210.5	Semi standard non polar	33892256
Xanthosine,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=C(O)N=C21	3215.6	Semi standard non polar	33892256
Xanthosine,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H](CO)O[C@@H](N2C=NC3=C(O)N=C(O)N=C32)[C@@H]1O	3199.1	Semi standard non polar	33892256
Xanthosine,1TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC1=NC(O)=C2N=CN([C@@H]3O[C@H](CO)[C@@H](O)[C@H]3O)C2=N1	3070.9	Semi standard non polar	33892256
Xanthosine,1TBDMS,isomer #5	CC(C)(C)[Si](C)(C)OC1=NC(O)=NC2=C1N=CN2[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O	3039.7	Semi standard non polar	33892256
Xanthosine,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=C(O)N=C32)[C@H](O)[C@@H]1O	3238.3	Semi standard non polar	33892256
Xanthosine,2TBDMS,isomer #10	CC(C)(C)[Si](C)(C)OC1=NC(O[Si](C)(C)C(C)(C)C)=C2N=CN([C@@H]3O[C@H](CO)[C@@H](O)[C@H]3O)C2=N1	3134.4	Semi standard non polar	33892256
Xanthosine,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC3=C(O)N=C(O[Si](C)(C)C(C)(C)C)N=C32)[C@H](O)[C@@H]1O	3277.9	Semi standard non polar	33892256
Xanthosine,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC3=C(O)N=C(O)N=C32)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O	3418.3	Semi standard non polar	33892256
Xanthosine,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC3=C(O)N=C(O)N=C32)[C@H](O)[C@@H]1O[Si](C)(C)C(C)(C)C	3415.3	Semi standard non polar	33892256
Xanthosine,2TBDMS,isomer #5	CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H](CO)O[C@@H](N2C=NC3=C(O)N=C(O)N=C32)[C@@H]1O[Si](C)(C)C(C)(C)C	3403.1	Semi standard non polar	33892256
Xanthosine,2TBDMS,isomer #6	CC(C)(C)[Si](C)(C)OC1=NC(O)=NC2=C1N=CN2[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O[Si](C)(C)C(C)(C)C	3229.9	Semi standard non polar	33892256
Xanthosine,2TBDMS,isomer #7	CC(C)(C)[Si](C)(C)OC1=NC(O)=C2N=CN([C@@H]3O[C@H](CO)[C@@H](O)[C@H]3O[Si](C)(C)C(C)(C)C)C2=N1	3271.3	Semi standard non polar	33892256
Xanthosine,2TBDMS,isomer #8	CC(C)(C)[Si](C)(C)OC1=NC(O)=NC2=C1N=CN2[C@@H]1O[C@H](CO)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]1O	3222.8	Semi standard non polar	33892256
Xanthosine,2TBDMS,isomer #9	CC(C)(C)[Si](C)(C)OC1=NC(O)=C2N=CN([C@@H]3O[C@H](CO)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]3O)C2=N1	3266.3	Semi standard non polar	33892256
Xanthosine,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=C(O[Si](C)(C)C(C)(C)C)N=C32)[C@H](O)[C@@H]1O	3330.7	Semi standard non polar	33892256
Xanthosine,3TBDMS,isomer #10	CC(C)(C)[Si](C)(C)OC1=NC(O[Si](C)(C)C(C)(C)C)=C2N=CN([C@@H]3O[C@H](CO)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]3O)C2=N1	3338.4	Semi standard non polar	33892256
Xanthosine,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=C(O)N=C32)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O	3355.2	Semi standard non polar	33892256
Xanthosine,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC3=C(O[Si](C)(C)C(C)(C)C)N=C(O)N=C32)[C@H](O)[C@@H]1O[Si](C)(C)C(C)(C)C	3351.7	Semi standard non polar	33892256
Xanthosine,3TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC3=C(O)N=C(O[Si](C)(C)C(C)(C)C)N=C32)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O	3416.6	Semi standard non polar	33892256
Xanthosine,3TBDMS,isomer #5	CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC3=C(O)N=C(O[Si](C)(C)C(C)(C)C)N=C32)[C@H](O)[C@@H]1O[Si](C)(C)C(C)(C)C	3410.8	Semi standard non polar	33892256
Xanthosine,3TBDMS,isomer #6	CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC3=C(O)N=C(O)N=C32)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O[Si](C)(C)C(C)(C)C	3523.2	Semi standard non polar	33892256
Xanthosine,3TBDMS,isomer #7	CC(C)(C)[Si](C)(C)OC1=NC(O)=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	3345.5	Semi standard non polar	33892256
Xanthosine,3TBDMS,isomer #8	CC(C)(C)[Si](C)(C)OC1=NC(O)=C2N=CN([C@@H]3O[C@H](CO)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]3O[Si](C)(C)C(C)(C)C)C2=N1	3407.7	Semi standard non polar	33892256
Xanthosine,3TBDMS,isomer #9	CC(C)(C)[Si](C)(C)OC1=NC(O[Si](C)(C)C(C)(C)C)=C2N=CN([C@@H]3O[C@H](CO)[C@@H](O)[C@H]3O[Si](C)(C)C(C)(C)C)C2=N1	3334.0	Semi standard non polar	33892256
Xanthosine,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=C(O[Si](C)(C)C(C)(C)C)N=C32)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O	3502.4	Semi standard non polar	33892256
Xanthosine,4TBDMS,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=C(O[Si](C)(C)C(C)(C)C)N=C32)[C@H](O)[C@@H]1O[Si](C)(C)C(C)(C)C	3503.4	Semi standard non polar	33892256
Xanthosine,4TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC3=C(O[Si](C)(C)C(C)(C)C)N=C(O)N=C32)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O[Si](C)(C)C(C)(C)C	3481.9	Semi standard non polar	33892256
Xanthosine,4TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC3=C(O)N=C(O[Si](C)(C)C(C)(C)C)N=C32)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O[Si](C)(C)C(C)(C)C	3535.2	Semi standard non polar	33892256
Xanthosine,4TBDMS,isomer #5	CC(C)(C)[Si](C)(C)OC1=NC(O[Si](C)(C)C(C)(C)C)=C2N=CN([C@@H]3O[C@H](CO)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]3O[Si](C)(C)C(C)(C)C)C2=N1	3492.9	Semi standard non polar	33892256
Xanthosine,5TBDMS,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=C(O[Si](C)(C)C(C)(C)C)N=C32)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O[Si](C)(C)C(C)(C)C	3682.6	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Xanthosine GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-0032-0963000000-08e48347b76242e521e6	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Xanthosine GC-EI-TOF (Non-derivatized)	splash10-0032-0963000000-08e48347b76242e521e6	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Xanthosine GC-MS (Non-derivatized) - 70eV, Positive	splash10-05fu-9250000000-9694fd3e1c7370e27866	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Xanthosine GC-MS (5 TMS) - 70eV, Positive	splash10-0059-2110049000-cbeec0d3159947f31d5f	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Xanthosine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Xanthosine GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Xanthosine GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Xanthosine GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Xanthosine GC-MS (TMS_1_4) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Xanthosine GC-MS (TMS_1_5) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Xanthosine GC-MS (TMS_2_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Xanthosine GC-MS (TMS_2_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Xanthosine GC-MS (TMS_2_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Xanthosine GC-MS (TMS_2_4) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Xanthosine GC-MS (TMS_2_5) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Xanthosine GC-MS (TMS_2_6) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Xanthosine GC-MS (TMS_2_7) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Xanthosine GC-MS (TMS_2_8) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Xanthosine GC-MS (TMS_2_9) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Xanthosine GC-MS (TMS_2_10) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Xanthosine GC-MS (TMS_3_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Xanthosine GC-MS (TMS_3_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Xanthosine GC-MS (TMS_3_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Xanthosine GC-MS (TMS_3_4) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Xanthosine GC-MS (TMS_3_5) - 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 - Xanthosine Quattro_QQQ 10V, Positive-QTOF (Annotated)	splash10-0udi-0900000000-e3e76f5bf26f34680c35	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Xanthosine Quattro_QQQ 25V, Positive-QTOF (Annotated)	splash10-0udi-7900000000-6e1f70509da5adf99678	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Xanthosine Quattro_QQQ 40V, Positive-QTOF (Annotated)	splash10-0a4r-9500000000-3cce63949eec45fa9204	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Xanthosine LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative-QTOF	splash10-0udi-0910000000-b2c7e01e9105bba310aa	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Xanthosine LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative-QTOF	splash10-0udi-0910000000-e6e1d21c0d22b3ad2821	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Xanthosine LC-ESI-QTOF , negative-QTOF	splash10-0udi-0910000000-b2c7e01e9105bba310aa	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Xanthosine LC-ESI-QTOF , negative-QTOF	splash10-0udi-0910000000-e6e1d21c0d22b3ad2821	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Xanthosine 40V, Positive-QTOF	splash10-0uk9-8900000000-b0f93d77cf447ada9ed9	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Xanthosine 20V, Positive-QTOF	splash10-0udi-1900000000-19c92745c311f6435fd3	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Xanthosine 35V, Positive-QTOF	splash10-0udi-2910000000-6f97748a645ffb972e67	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Xanthosine 0V, Positive-QTOF	splash10-03di-0900000000-a999e0e022115ec9ec7a	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Xanthosine 10V, Positive-QTOF	splash10-0udi-0910000000-63959f162289e268a620	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Xanthosine 20V, Positive-QTOF	splash10-0zg0-8900000000-f8aa72afbf821cfb2cf2	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Xanthosine 10V, Positive-QTOF	splash10-0udi-4900000000-943b0d3fbe3cd8345d54	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Xanthosine 40V, Positive-QTOF	splash10-06rl-9400000000-3072bed88bbdca66de69	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Xanthosine 35V, Negative-QTOF	splash10-0udi-0900000000-f3b10c4bf03522fbd1ff	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Xanthosine 10V, Negative-QTOF	splash10-0udi-0940000000-f59c82b81d81cd9c6b68	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Xanthosine 30V, Negative-QTOF	splash10-0udi-0900000000-e0cf07456bb1d35aec56	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Xanthosine 20V, Negative-QTOF	splash10-0udi-0900000000-6189db27589e05c3f039	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Xanthosine 10V, Positive-QTOF	splash10-0udi-0940000000-2394018b58d040767e06	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Xanthosine 20V, Positive-QTOF	splash10-0udi-0900000000-fec1dd4fe1f5f7e56482	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Xanthosine 40V, Positive-QTOF	splash10-0f79-1900000000-850759ea222062877fa9	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Xanthosine 10V, Negative-QTOF	splash10-0f8c-1590000000-4fdccf755ee2b8b75ac6	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Xanthosine 20V, Negative-QTOF	splash10-0f6x-6910000000-308e886a8ecec5d8cd09	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Xanthosine 40V, Negative-QTOF	splash10-0006-9500000000-af861bef2f6b2f10296c	2016-09-12	Wishart Lab	View Spectrum

NMR Spectra

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

Biospecimen Locations

Blood
Feces
Urine

Tissue Locations

Placenta

Pathways

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

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	5.08 +/- 0.30 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	0.0842 +/- 0.0451 uM	Adult (>18 years old)	Both	Normal	12675874	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	29808030	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	25037050	details
Feces	Detected but not Quantified	Not Quantified	Children (6 - 18 years old)	Not Specified	Normal	27609529	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	27543620	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Urine	Detected and Quantified	0.59 +/- 0.36 umol/mmol creatinine	Adult (>18 years old)	Female	Normal	9129323	details
Urine	Detected and Quantified	2.14 (1.63-3.42) umol/mmol creatinine	Newborn (0-30 days old)	Both	Normal	Analysis of 40 NI...	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.340 +/- 0.221 uM	Adult (>18 years old)	Both	Uremia	12675874	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Metastatic melanoma	28923537	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	25037050	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
Urine	Detected and Quantified	0.99 umol/mmol creatinine	Adult (>18 years old)	Both	Breast tumour	9129323	details

Associated Disorders and Diseases

Disease References

Uremia
Vanholder R, De Smet R, Glorieux G, Argiles A, Baurmeister U, Brunet P, Clark W, Cohen G, De Deyn PP, Deppisch R, Descamps-Latscha B, Henle T, Jorres A, Lemke HD, Massy ZA, Passlick-Deetjen J, Rodriguez M, Stegmayr B, Stenvinkel P, Tetta C, Wanner C, Zidek W: Review on uremic toxins: classification, concentration, and interindividual variability. Kidney Int. 2003 May;63(5):1934-43. doi: 10.1046/j.1523-1755.2003.00924.x. [PubMed:12675874 ]
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 ]
Metastatic melanoma
Frankel AE, Coughlin LA, Kim J, Froehlich TW, Xie Y, Frenkel EP, Koh AY: Metagenomic Shotgun Sequencing and Unbiased Metabolomic Profiling Identify Specific Human Gut Microbiota and Metabolites Associated with Immune Checkpoint Therapy Efficacy in Melanoma Patients. Neoplasia. 2017 Oct;19(10):848-855. doi: 10.1016/j.neo.2017.08.004. Epub 2017 Sep 15. [PubMed:28923537 ]
Colorectal cancer
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 ]

Associated OMIM IDs

266600 (Crohn's disease)
114500 (Colorectal cancer)

External Links

DrugBank ID

Not Available

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

PDB ID

Not Available

ChEBI ID

18107

Food Biomarker Ontology

Not Available

VMH ID

XTSN

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Enei, Hitoshi; Sato, Katsuaki; Hirose, Yoshio. Xanthosine production by fermentation. Jpn. Kokai Tokkyo Koho (1975), 3 pp.

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Marti R, Nishigaki Y, Hirano M: Elevated plasma deoxyuridine in patients with thymidine phosphorylase deficiency. Biochem Biophys Res Commun. 2003 Mar 28;303(1):14-8. [PubMed:12646159 ]
Dudley E, Lemiere F, Van Dongen W, Tuytten R, El-Sharkawi S, Brenton AG, Esmans EL, Newton RP: Analysis of urinary nucleosides. IV. Identification of urinary purine nucleosides by liquid chromatography/electrospray mass spectrometry. Rapid Commun Mass Spectrom. 2004;18(22):2730-8. [PubMed:15499664 ]
Liebich HM, Di Stefano C, Wixforth A, Schmid HR: Quantitation of urinary nucleosides by high-performance liquid chromatography. J Chromatogr A. 1997 Feb 28;763(1-2):193-7. [PubMed:9129323 ]
Khalil PN, Erb N, Khalil MN, Escherich G, Janka-Schaub GE: Validation and application of a high-performance liquid chromatographic-based assay for determination of the inosine 5'-monophosphate dehydrogenase activity in erythrocytes. J Chromatogr B Analyt Technol Biomed Life Sci. 2006 Sep 14;842(1):1-7. Epub 2006 May 24. [PubMed:16725387 ]
Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]

Enzymes

Enzyme Details

1. 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

Xanthylic acid + Water → Xanthosine + 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

Xanthylic acid + Water → Xanthosine + 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

Xanthylic acid + Water → Xanthosine + 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

Xanthylic acid + Water → Xanthosine + 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

Xanthylic acid + Water → Xanthosine + Phosphate	details

Enzyme Details

6. Inosine triphosphate pyrophosphatase

General function:: Involved in hydrolase activity
Specific function:: Pyrophosphatase that hydrolyzes the non-canonical purine nucleotides inosine triphosphate (ITP), deoxyinosine triphosphate (dITP) as well as 2'-deoxy-N-6-hydroxylaminopurine triposphate (dHAPTP) and xanthosine 5'-triphosphate (XTP) to their respective monophosphate derivatives. The enzyme does not distinguish between the deoxy- and ribose forms. Probably excludes non-canonical purines from RNA and DNA precursor pools, thus preventing their incorporation into RNA and DNA and avoiding chromosomal lesions.
Gene Name:: ITPA
Uniprot ID:: Q9BY32
Molecular weight:: 16833.23

Enzyme Details

7. 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

Xanthylic acid + Water → Xanthosine + Phosphate	details

Enzyme Details

8. 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

Xanthylic acid + Water → Xanthosine + Phosphate	details

Enzyme Details

9. Purine nucleoside phosphorylase

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

Reactions

Xanthosine + Phosphate → Xanthine + Ribose 1-phosphate	details

Showing metabocard for Xanthosine (HMDB0000299)

MOL for HMDB0000299 (Xanthosine)

3D MOL for HMDB0000299 (Xanthosine)

3D SDF for HMDB0000299 (Xanthosine)

3D-SDF for HMDB0000299 (Xanthosine)

PDB for HMDB0000299 (Xanthosine)

3D PDB for HMDB0000299 (Xanthosine)

SMILES for HMDB0000299 (Xanthosine)

INCHI for HMDB0000299 (Xanthosine)

Structure for HMDB0000299 (Xanthosine)

3D Structure for HMDB0000299 (Xanthosine)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes

Reactions

Reactions

Reactions

Reactions

Reactions

Reactions

Reactions

Reactions