MiMeDB: Showing metabocard for Xanthosine (MMDBc0000338)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2020-12-10 18:35:40 UTC

Update Date

2024-04-30 19:31:51 UTC

Metabolite ID

MMDBc0000338

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>
MMDBc0000338

> <DATABASE_NAME>
MIME

> <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

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

Molecular Formula

C₁₀H₁₂N₄O₆

Average Mass

284.2255

Monoisotopic Mass

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

Not Available

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 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted 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

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-0032-0963000000-08e48347b76242e521e6	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0032-0963000000-08e48347b76242e521e6	2017-09-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-05fu-9250000000-9694fd3e1c7370e27866	2017-09-01	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (5 TMS) - 70eV, Positive	splash10-0059-2110049000-cbeec0d3159947f31d5f	2017-10-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_4) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_5) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_4) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_5) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_6) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_7) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_8) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_9) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_10) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_3_1) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_3_2) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_3_3) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_3_4) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_3_5) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-0udi-0900000000-e3e76f5bf26f34680c35	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-0udi-7900000000-6e1f70509da5adf99678	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-0a4r-9500000000-3cce63949eec45fa9204	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative	splash10-0udi-0910000000-b2c7e01e9105bba310aa	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative	splash10-0udi-0910000000-e6e1d21c0d22b3ad2821	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-0udi-0910000000-b2c7e01e9105bba310aa	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-0udi-0910000000-e6e1d21c0d22b3ad2821	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-0uk9-8900000000-b0f93d77cf447ada9ed9	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-0udi-1900000000-19c92745c311f6435fd3	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Positive	splash10-0udi-2910000000-6f97748a645ffb972e67	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 0V, Positive	splash10-03di-0900000000-a999e0e022115ec9ec7a	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-0910000000-63959f162289e268a620	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-0zg0-8900000000-f8aa72afbf821cfb2cf2	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-4900000000-943b0d3fbe3cd8345d54	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-06rl-9400000000-3072bed88bbdca66de69	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-0udi-0900000000-f3b10c4bf03522fbd1ff	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0940000000-f59c82b81d81cd9c6b68	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Negative	splash10-0udi-0900000000-e0cf07456bb1d35aec56	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-0udi-0900000000-6189db27589e05c3f039	2021-09-20	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-0940000000-2394018b58d040767e06	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0udi-0900000000-fec1dd4fe1f5f7e56482	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0f79-1900000000-850759ea222062877fa9	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0f8c-1590000000-4fdccf755ee2b8b75ac6	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0f6x-6910000000-308e886a8ecec5d8cd09	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9500000000-af861bef2f6b2f10296c	2016-09-12	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)		2012-12-04	View Spectrum
1D NMR	¹H NMR Spectrum (1D, D₂O, experimental)		2016-10-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-16	View Spectrum
2D NMR	[¹H, ¹H]-TOCSY. Unexported temporarily by An Chi on Oct 15, 2021 until json or nmrML file is generated. 2D NMR Spectrum (experimental)		2012-12-04	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)		2012-12-05	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm

Biospecimen Locations

Blood
Feces
Placenta
Urine

Tissue Locations

Placenta

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species
MMDBp0191677	5'-nucleotidase	Unknown	P21589	Homo sapiens
MMDBp0191680	Cytosolic 5'-nucleotidase 1B	Unknown	Q96P26	Homo sapiens
MMDBp0191681	Cytosolic 5'-nucleotidase 1A	Unknown	Q9BXI3	Homo sapiens
MMDBp0191682	5'(3')-deoxyribonucleotidase, cytosolic type	Unknown	Q8TCD5	Homo sapiens
MMDBp0191684	5'(3')-deoxyribonucleotidase, mitochondrial	Unknown	Q9NPB1	Homo sapiens
MMDBp0192097	Inosine triphosphate pyrophosphatase	Unknown	Q9BY32	Homo sapiens
MMDBp0193860	Cytosolic 5'-nucleotidase 3	Enzyme	Q9H0P0	Homo sapiens
MMDBp0193932	Cytosolic purine 5'-nucleotidase	Unknown	P49902	Homo sapiens
MMDBp0193933	Purine nucleoside phosphorylase	Enzyme	P00491	Homo sapiens

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference
MMDBr0002940	Guanosine	Ammonia	Not Available	Guanosine Aminohydrolase	VMH; KEGG	30371894
MMDBr0005596	Xanthosine	Xanthosine	Not Available	Transport of Xanthosine	VMH	30371894
MMDBr0007155	Water	D-Ribose	Not Available	Xanthosine hydrolase	VMH	30371894
MMDBr0007559	Phosphate	Ribose-1-phosphate	Not Available	Purine-Nucleoside Phosphorylase (Xanthosine)	VMH; KEGG	30371894
MMDBr0007644	Water	Phosphate	Not Available	5'-Nucleotidase (XMP)	VMH; KEGG	30371894
MMDBr0008011	Hydrogen Ion	Hydrogen Ion	Not Available	Xanthosine transport via proton symport (periplasm)	VMH	30371894
MMDBr0014707	Phosphate	Ribose-1-phosphate	Pyrimidine/purine nucleoside phosphorylase	Phosphorylation	RHEA	34755880
MMDBr0014845	Water	Phosphate	5'-nucleotidase YutF	Hydrolysis of nucleotide	RHEA	34755880
MMDBr0019314	Xanthosine	Xanthine	Purine nucleoside phosphorylase 2	Phosphorylation	PathBank	31602464

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference
Uremia		Association	Human Blood	HMDB	12675874

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Firmicutes	389	Human stool; Human ; Human urine; Human feces; Human pleural fluid plaque; Pig ; Human mucosa; Human sputum; Human saliva; Human supragingival plaque; Cattle ; Human subgingival plaque	Indirect association between microbiota composition and metabolites measured in host biospecimen; Metabolic reconstruction
Bacteria	Proteobacteria	370	Human feces; Human sputum; Human ; Human unknown; Pig ; Human pleural fluid plaque; Human dental plaque; Human nasal swab; Human stool; Human feces; pleural fluid plaque; bal; River trout ; Cattle	Metabolic reconstruction
Bacteria	Actinobacteria	129	Human feces; Human sputum; Human bronchial brush; Human nasopharyngeal swab; Human pleural fluid plaque; Human dental plaque; Human ; Human supragingival plaque; Human mucosa; Human subgingival plaque; Human saliva	Metabolic reconstruction
Bacteria	Verrucomicrobia	1	Human ; Human feces	Metabolic reconstruction
Bacteria	Bacteroidetes	126	Human feces; Human appendix biopsy; Human ; Human stool; Human saliva; Human gastric fluid; Human urine; Human subgingival plaque; Human supragingival plaque	Metabolic reconstruction
Bacteria	Synergistetes	4	Human feces	Metabolic reconstruction
Bacteria	Spirochaetes	5	Human feces; Human	Metabolic reconstruction
Archaea	Thaumarchaeota	1		Metabolic reconstruction
Bacteria	Fusobacteria	20	Human feces; Human	Metabolic reconstruction
Archaea	Euryarchaeota	5		Metabolic reconstruction
Bacteria	Candidatus melainabacteria	1	Human feces	Metabolic reconstruction
Bacteria	Tenericutes	4	Human feces	Metabolic reconstruction
Bacteria	Planctomycetes	2	Human feces	Metabolic reconstruction
Archaea	Crenarchaeota	1		Metabolic reconstruction
Bacteria	Chlorobi	1
Eukaryota/Fungi	Ascomycota	1	Human feces; Human saliva	Unknown

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Units	Age	Sex	Health Condition	Data Source	Reference
Human Feces	Detected but not Quantified							HMDB
Human Blood	Detected and Quantified	0.340	0.221	uM	Adult (>18 years old)	Both	Uremia	HMDB	12675874
Human Blood	Detected and Quantified	0.0842	0.0451	uM	Adult (>18 years old)	Both	Normal	HMDB	12675874
Human Urine	Detected and Quantified	0.59	0.36	umol/mmol creatinine	Adult (>18 years old)	Female	Normal	HMDB	9129323
Human Blood	Detected and Quantified	5.08	0.30	uM	Adult (>18 years old)	Both	Normal	HMDB	16139832
Human Placenta	Detected but not Quantified				Not Specified	Not Specified	Normal	HMDB	34986597
Human Feces	Detected but not Quantified				Children (6 - 18 years old)	Not Specified	Normal	HMDB	27609529
Human Feces	Detected but not Quantified				Adult (>18 years old)	Both	Normal	HMDB	27543620
Human Feces	Detected but not Quantified				Adult (>18 years old)	Both	Normal	HMDB	25037050
Human Feces	Detected but not Quantified				Adult (>18 years old)	Both	Normal	HMDB	29808030
Human Urine	Detected but not Quantified				Adult (>18 years old)	Both	Normal	HMDB	32966057
Human Blood	Detected but not Quantified				Adult (>18 years old)	Both	Normal	HMDB	32966057

External Links

HMDB ID

HMDB0000299

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

References

Synthesis Reference

Not Available

General References

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. doi: 10.1016/s0021-9673(96)00757-1. [PubMed:9129323 ]
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. doi: 10.1016/s0006-291x(03)00294-8. [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. doi: 10.1002/rcm.1685. [PubMed:15499664 ]
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. doi: 10.1016/j.jchromb.2006.04.040. 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 ]

Showing metabocard for Xanthosine (MMDBc0000338)

MOL for #<Metabolite:0x00007fd100354020>

3D MOL for #<Metabolite:0x00007fd100354020>

3D SDF for #<Metabolite:0x00007fd100354020>

3D-SDF for #<Metabolite:0x00007fd100354020>

PDB for #<Metabolite:0x00007fd100354020>

3D PDB for #<Metabolite:0x00007fd100354020>

SMILES for #<Metabolite:0x00007fd100354020>

INCHI for #<Metabolite:0x00007fd100354020>

Structure for #<Metabolite:0x00007fd100354020>

3D Structure for #<Metabolite:0x00007fd100354020>