MiMeDB: Showing metabocard for Xanthylic acid (MMDBc0029670)

Microbial

Plant

Animal

Record Information

Version

2.0

Status

Detected and Quantified

Creation Date

2021-11-17 23:36:52 UTC

Update Date

2024-04-30 19:40:25 UTC

Metabolite ID

MMDBc0029670

Metabolite Identification

Common Name

Xanthylic acid

Description

Xanthylic acid is an important metabolic intermediate in the purine metabolism, and is a product or substrate of the enzymes inosine monophosphate dehydrogenase (EC 1.1.1.205), hypoxanthine phosphoribosyltransferase (EC 2.4.2.8), xanthine phosphoribosyltransferase (EC 2.4.2.22), 5'-ribonucleotide phosphohydrolase (EC 3.1.3.5), Ap4A hydrolase (EC 3.6.1.17), nucleoside-triphosphate diphosphatase (EC 3.6.1.19), phosphoribosylamine-glycine ligase (EC 6.3.4.1), and glutamine amidotransferase (EC 6.3.5.2). (KEGG)

Structure

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

HMDB0001554
     RDKit          3D
Xanthylic acid
 37 39  0  0  0  0  0  0  0  0999 V2000
   -3.7586    2.4018    1.7693 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6860    1.4332    1.0050 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6526    1.2079    0.1018 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6091    0.1841   -0.7442 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5076   -0.0362   -1.5799 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5310   -0.6848   -0.7096 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1666   -1.7766   -1.4185 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9845   -2.1944   -0.9643 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5659   -1.4097    0.0281 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3205   -1.4810    0.7797 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0074   -0.1437    1.1104 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1728    0.1148    0.5995 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2037    1.2115   -0.4684 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4984    1.0765   -1.0060 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4948    2.3566   -0.7232 P   0  0  0  0  0  5  0  0  0  0  0  0
    3.3554    2.8090    0.7514 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0839    1.6598   -0.7638 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4494    3.6698   -1.6900 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9388   -1.0860    0.2050 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6270   -1.5344    1.3310 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7937   -2.0304   -0.0771 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2096   -3.2823    0.3488 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5048   -0.4653    0.2232 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6513    0.5920    1.0381 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4746    1.8659    0.0027 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4562   -3.0616   -1.3539 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3702   -2.0487    1.7126 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7828    0.6232    1.4689 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5060    0.7933   -1.2690 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8776    2.1535   -0.1695 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0039    0.6767   -0.4908 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1894    3.6945   -2.3465 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6626   -0.9512   -0.5839 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5464   -1.8047    1.1464 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5546   -2.0696   -1.1641 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2305   -3.2553    1.3572 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9345    0.7921    1.7712 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
 15 18  1  0
 12 19  1  0
 19 20  1  0
 19 21  1  0
 21 22  1  0
  9 23  1  0
 23 24  1  0
 24  2  1  0
 23  6  2  0
 21 10  1  0
  3 25  1  0
  8 26  1  0
 10 27  1  1
 12 28  1  1
 13 29  1  0
 13 30  1  0
 17 31  1  0
 18 32  1  0
 19 33  1  6
 20 34  1  0
 21 35  1  6
 22 36  1  0
 24 37  1  0
M  END


  Mrv1652305012019262D          

 24 26  0  0  0  0            999 V2000
 9999.8098 9998.0286    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10002.1105 9999.8848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.6018 9998.0204    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10002.8259 9999.4704    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10003.5434 9999.8848    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
10003.129910000.6014    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10004.2588 9999.4704    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10003.956910000.6014    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.7231 9999.9643    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.3106 9998.6947    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10001.1356 9998.6947    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10001.3905 9999.4793    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9998.447410000.8803    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9999.3406 9999.8883    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9999.254310000.7087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.674710000.6086    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9997.2698 9997.8085    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9997.2279 9999.9943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.9729 9999.2097    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9997.5250 9998.5965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.3320 9998.7681    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9998.5870 9999.5527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.034910000.1659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.0551 9999.4758    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  5  8  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
  9 12  1  0  0  0  0
 10  1  1  1  0  0  0
 12  2  1  6  0  0  0
 11  3  1  1  0  0  0
 13 15  2  0  0  0  0
 14 15  1  0  0  0  0
 18 23  1  0  0  0  0
 22 23  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 16 18  2  0  0  0  0
 20 17  2  0  0  0  0
 13 23  1  0  0  0  0
 22 14  1  0  0  0  0
 24 14  1  6  0  0  0
 24 10  1  0  0  0  0
  9 24  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0029670

> <DATABASE_NAME>
MIME

> <SMILES>
O[C@@H]1[C@@H](COP(O)(O)=O)O[C@H]([C@@H]1O)N1C=NC2=C1NC(=O)NC2=O

> <INCHI_IDENTIFIER>
InChI=1S/C10H13N4O9P/c15-5-3(1-22-24(19,20)21)23-9(6(5)16)14-2-11-4-7(14)12-10(18)13-8(4)17/h2-3,5-6,9,15-16H,1H2,(H2,19,20,21)(H2,12,13,17,18)/t3-,5-,6-,9-/m1/s1

> <INCHI_KEY>
DCTLYFZHFGENCW-UUOKFMHZSA-N

> <FORMULA>
C10H13N4O9P

> <MOLECULAR_WEIGHT>
364.2054

> <EXACT_MASS>
364.042014546

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
37

> <JCHEM_AVERAGE_POLARIZABILITY>
29.985224417890663

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
{[(2R,3S,4R,5R)-5-(2,6-dioxo-2,3,6,9-tetrahydro-1H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}phosphonic acid

> <ALOGPS_LOGP>
-1.95

> <JCHEM_LOGP>
-2.178401021903641

> <ALOGPS_LOGS>
-2.17

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
6.249797574142393

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.2561237815860213

> <JCHEM_PKA_STRONGEST_BASIC>
0.06851150749800639

> <JCHEM_POLAR_SURFACE_AREA>
192.46999999999997

> <JCHEM_REFRACTIVITY>
73.08139999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.49e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
xanthosine monophosphate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0001554
     RDKit          3D
Xanthylic acid
 37 39  0  0  0  0  0  0  0  0999 V2000
   -3.7586    2.4018    1.7693 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6860    1.4332    1.0050 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6526    1.2079    0.1018 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6091    0.1841   -0.7442 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5076   -0.0362   -1.5799 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5310   -0.6848   -0.7096 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1666   -1.7766   -1.4185 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9845   -2.1944   -0.9643 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5659   -1.4097    0.0281 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3205   -1.4810    0.7797 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0074   -0.1437    1.1104 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1728    0.1148    0.5995 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2037    1.2115   -0.4684 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4984    1.0765   -1.0060 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4948    2.3566   -0.7232 P   0  0  0  0  0  5  0  0  0  0  0  0
    3.3554    2.8090    0.7514 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0839    1.6598   -0.7638 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4494    3.6698   -1.6900 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9388   -1.0860    0.2050 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6270   -1.5344    1.3310 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7937   -2.0304   -0.0771 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2096   -3.2823    0.3488 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5048   -0.4653    0.2232 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6513    0.5920    1.0381 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4746    1.8659    0.0027 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4562   -3.0616   -1.3539 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3702   -2.0487    1.7126 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7828    0.6232    1.4689 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5060    0.7933   -1.2690 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8776    2.1535   -0.1695 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0039    0.6767   -0.4908 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1894    3.6945   -2.3465 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6626   -0.9512   -0.5839 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5464   -1.8047    1.1464 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5546   -2.0696   -1.1641 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2305   -3.2553    1.3572 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9345    0.7921    1.7712 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
 15 18  1  0
 12 19  1  0
 19 20  1  0
 19 21  1  0
 21 22  1  0
  9 23  1  0
 23 24  1  0
 24  2  1  0
 23  6  2  0
 21 10  1  0
  3 25  1  0
  8 26  1  0
 10 27  1  1
 12 28  1  1
 13 29  1  0
 13 30  1  0
 17 31  1  0
 18 32  1  0
 19 33  1  6
 20 34  1  0
 21 35  1  6
 22 36  1  0
 24 37  1  0
M  END

HEADER    PROTEIN                                 01-MAY-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   01-MAY-20         0                                  
HETATM    1  O   UNK     0    8666.3128662.987   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0    8670.6068666.452   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0    8669.6578662.971   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0    8671.9428665.678   0.000  0.00  0.00           O+0
HETATM    5  P   UNK     0    8673.2818666.452   0.000  0.00  0.00           P+0
HETATM    6  O   UNK     0    8672.5098667.789   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0    8674.6168665.678   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0    8674.0538667.789   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0    8668.0168666.600   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0    8667.2468664.230   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8668.7868664.230   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8669.2628665.695   0.000  0.00  0.00           C+0
HETATM   13  N   UNK     0    8663.7688668.310   0.000  0.00  0.00           N+0
HETATM   14  N   UNK     0    8665.4368666.458   0.000  0.00  0.00           N+0
HETATM   15  C   UNK     0    8665.2758667.990   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0    8660.4598667.803   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0    8661.5708662.576   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0    8661.4928666.656   0.000  0.00  0.00           C+0
HETATM   19  N   UNK     0    8661.0168665.191   0.000  0.00  0.00           N+0
HETATM   20  C   UNK     0    8662.0478664.047   0.000  0.00  0.00           C+0
HETATM   21  N   UNK     0    8663.5538664.367   0.000  0.00  0.00           N+0
HETATM   22  C   UNK     0    8664.0298665.832   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0    8662.9988666.976   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0    8666.7708665.688   0.000  0.00  0.00           C+0
CONECT    1   10                                                            
CONECT    2    4   12                                                       
CONECT    3   11                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6    7    8                                             
CONECT    6    5                                                            
CONECT    7    5                                                            
CONECT    8    5                                                            
CONECT    9   12   24                                                       
CONECT   10   11    1   24                                                  
CONECT   11   10   12    3                                                  
CONECT   12   11    9    2                                                  
CONECT   13   15   23                                                       
CONECT   14   15   22   24                                                  
CONECT   15   13   14                                                       
CONECT   16   18                                                            
CONECT   17   20                                                            
CONECT   18   23   19   16                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   17                                                  
CONECT   21   20   22                                                       
CONECT   22   23   21   14                                                  
CONECT   23   18   22   13                                                  
CONECT   24   14   10    9                                                  
MASTER        0    0    0    0    0    0    0    0   24    0   52    0
END

COMPND    HMDB0001554
HETATM    1  O1  UNL     1      -3.759   2.402   1.769  1.00  0.00           O  
HETATM    2  C1  UNL     1      -3.686   1.433   1.005  1.00  0.00           C  
HETATM    3  N1  UNL     1      -4.653   1.208   0.102  1.00  0.00           N  
HETATM    4  C2  UNL     1      -4.609   0.184  -0.744  1.00  0.00           C  
HETATM    5  O2  UNL     1      -5.508  -0.036  -1.580  1.00  0.00           O  
HETATM    6  C3  UNL     1      -3.531  -0.685  -0.710  1.00  0.00           C  
HETATM    7  N2  UNL     1      -3.167  -1.777  -1.418  1.00  0.00           N  
HETATM    8  C4  UNL     1      -1.985  -2.194  -0.964  1.00  0.00           C  
HETATM    9  N3  UNL     1      -1.566  -1.410   0.028  1.00  0.00           N  
HETATM   10  C5  UNL     1      -0.320  -1.481   0.780  1.00  0.00           C  
HETATM   11  O3  UNL     1      -0.007  -0.144   1.110  1.00  0.00           O  
HETATM   12  C6  UNL     1       1.173   0.115   0.600  1.00  0.00           C  
HETATM   13  C7  UNL     1       1.204   1.211  -0.468  1.00  0.00           C  
HETATM   14  O4  UNL     1       2.498   1.076  -1.006  1.00  0.00           O  
HETATM   15  P1  UNL     1       3.495   2.357  -0.723  1.00  0.00           P  
HETATM   16  O5  UNL     1       3.355   2.809   0.751  1.00  0.00           O  
HETATM   17  O6  UNL     1       5.084   1.660  -0.764  1.00  0.00           O  
HETATM   18  O7  UNL     1       3.449   3.670  -1.690  1.00  0.00           O  
HETATM   19  C8  UNL     1       1.939  -1.086   0.205  1.00  0.00           C  
HETATM   20  O8  UNL     1       2.627  -1.534   1.331  1.00  0.00           O  
HETATM   21  C9  UNL     1       0.794  -2.030  -0.077  1.00  0.00           C  
HETATM   22  O9  UNL     1       1.210  -3.282   0.349  1.00  0.00           O  
HETATM   23  C10 UNL     1      -2.505  -0.465   0.223  1.00  0.00           C  
HETATM   24  N4  UNL     1      -2.651   0.592   1.038  1.00  0.00           N  
HETATM   25  H1  UNL     1      -5.475   1.866   0.003  1.00  0.00           H  
HETATM   26  H2  UNL     1      -1.456  -3.062  -1.354  1.00  0.00           H  
HETATM   27  H3  UNL     1      -0.370  -2.049   1.713  1.00  0.00           H  
HETATM   28  H4  UNL     1       1.783   0.623   1.469  1.00  0.00           H  
HETATM   29  H5  UNL     1       0.506   0.793  -1.269  1.00  0.00           H  
HETATM   30  H6  UNL     1       0.878   2.153  -0.169  1.00  0.00           H  
HETATM   31  H7  UNL     1       5.004   0.677  -0.491  1.00  0.00           H  
HETATM   32  H8  UNL     1       4.189   3.694  -2.347  1.00  0.00           H  
HETATM   33  H9  UNL     1       2.663  -0.951  -0.584  1.00  0.00           H  
HETATM   34  H10 UNL     1       3.546  -1.805   1.146  1.00  0.00           H  
HETATM   35  H11 UNL     1       0.555  -2.070  -1.164  1.00  0.00           H  
HETATM   36  H12 UNL     1       1.231  -3.255   1.357  1.00  0.00           H  
HETATM   37  H13 UNL     1      -1.935   0.792   1.771  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   24
CONECT    3    4   25
CONECT    4    5    5    6
CONECT    6    7   23   23
CONECT    7    8    8
CONECT    8    9   26
CONECT    9   10   23
CONECT   10   11   21   27
CONECT   11   12
CONECT   12   13   19   28
CONECT   13   14   29   30
CONECT   14   15
CONECT   15   16   16   17   18
CONECT   17   31
CONECT   18   32
CONECT   19   20   21   33
CONECT   20   34
CONECT   21   22   35
CONECT   22   36
CONECT   23   24
CONECT   24   37
END

HMDB0001554
     RDKit          3D
Xanthylic acid
 37 39  0  0  0  0  0  0  0  0999 V2000
   -3.7586    2.4018    1.7693 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6860    1.4332    1.0050 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6526    1.2079    0.1018 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6091    0.1841   -0.7442 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5076   -0.0362   -1.5799 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5310   -0.6848   -0.7096 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1666   -1.7766   -1.4185 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9845   -2.1944   -0.9643 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5659   -1.4097    0.0281 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3205   -1.4810    0.7797 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0074   -0.1437    1.1104 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1728    0.1148    0.5995 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2037    1.2115   -0.4684 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4984    1.0765   -1.0060 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4948    2.3566   -0.7232 P   0  0  0  0  0  5  0  0  0  0  0  0
    3.3554    2.8090    0.7514 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0839    1.6598   -0.7638 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4494    3.6698   -1.6900 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9388   -1.0860    0.2050 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6270   -1.5344    1.3310 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7937   -2.0304   -0.0771 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2096   -3.2823    0.3488 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5048   -0.4653    0.2232 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6513    0.5920    1.0381 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4746    1.8659    0.0027 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4562   -3.0616   -1.3539 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3702   -2.0487    1.7126 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7828    0.6232    1.4689 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5060    0.7933   -1.2690 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8776    2.1535   -0.1695 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0039    0.6767   -0.4908 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1894    3.6945   -2.3465 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6626   -0.9512   -0.5839 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5464   -1.8047    1.1464 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5546   -2.0696   -1.1641 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2305   -3.2553    1.3572 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9345    0.7921    1.7712 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
 15 18  1  0
 12 19  1  0
 19 20  1  0
 19 21  1  0
 21 22  1  0
  9 23  1  0
 23 24  1  0
 24  2  1  0
 23  6  2  0
 21 10  1  0
  3 25  1  0
  8 26  1  0
 10 27  1  1
 12 28  1  1
 13 29  1  0
 13 30  1  0
 17 31  1  0
 18 32  1  0
 19 33  1  6
 20 34  1  0
 21 35  1  6
 22 36  1  0
 24 37  1  0
M  END

Synonyms

Value	Source
(9-D-Ribosylxanthine)-5'-phosphate	ChEBI
Xanthosine 5'-phosphate	ChEBI
Xanthosine monophosphate	ChEBI
XMP	ChEBI
(9-D-Ribosylxanthine)-5'-phosphoric acid	Generator
Xanthylate	Generator
Xanthosine 5'-phosphoric acid	Generator
Xanthosine monophosphoric acid	Generator
5'-Xanthonylate monophosphate	HMDB
Xanthosine-5'-P	HMDB
Xanthosine-5'-phosphate	HMDB
Xanthosine monophosphate, 8-(14)C-labeled	MeSH, HMDB
Xanthosine 5'-monophosphate	HMDB
Xanthosine 5’-monophosphate	HMDB
Xanthosine 5’-phosphate	HMDB
Xanthylic acid	HMDB

Molecular Formula

C₁₀H₁₃N₄O₉P

Average Mass

364.2054

Monoisotopic Mass

364.042014546

IUPAC Name

{[(2R,3S,4R,5R)-5-(2,6-dioxo-2,3,6,9-tetrahydro-1H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}phosphonic acid

Traditional Name

xanthosine monophosphate

CAS Registry Number

523-98-8

SMILES

O[C@@H]1[C@@H](COP(O)(O)=O)O[C@H]([C@@H]1O)N1C=NC2=C1NC(=O)NC2=O

InChI Identifier

InChI=1S/C10H13N4O9P/c15-5-3(1-22-24(19,20)21)23-9(6(5)16)14-2-11-4-7(14)12-10(18)13-8(4)17/h2-3,5-6,9,15-16H,1H2,(H2,19,20,21)(H2,12,13,17,18)/t3-,5-,6-,9-/m1/s1

InChI Key

DCTLYFZHFGENCW-UUOKFMHZSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as purine ribonucleoside monophosphates. These are nucleotides consisting of a purine base linked to a ribose to which one monophosphate group is attached.

Kingdom

Organic compounds

Super Class

Nucleosides, nucleotides, and analogues

Class

Purine nucleotides

Sub Class

Purine ribonucleotides

Direct Parent

Purine ribonucleoside monophosphates

Alternative Parents

Substituents

Purine ribonucleoside monophosphate
Pentose phosphate
Pentose-5-phosphate
Glycosyl compound
N-glycosyl compound
Xanthine
6-oxopurine
Monosaccharide phosphate
Pentose monosaccharide
Purinone
Imidazopyrimidine
Purine
Alkaloid or derivatives
Monoalkyl phosphate
Pyrimidone
Monosaccharide
N-substituted imidazole
Organic phosphoric acid derivative
Alkyl phosphate
Phosphoric acid ester
Pyrimidine
Heteroaromatic compound
Azole
Vinylogous amide
Imidazole
Tetrahydrofuran
Lactam
1,2-diol
Urea
Secondary alcohol
Azacycle
Oxacycle
Organoheterocyclic compound
Alcohol
Organic oxide
Organonitrogen compound
Organopnictogen compound
Organic oxygen compound
Organooxygen compound
Hydrocarbon derivative
Organic nitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

xanthosine 5'-phosphate (CHEBI:15652 )
purine ribonucleoside 5'-monophosphate (CHEBI:15652 )
Purine alkaloids (C00655 )

Functional Ontology

Not Available

Physical Properties

State

Solid

Predicted Properties

Property	Value	Source
Water Solubility	2.49 g/L	ALOGPS
logP	-2	ALOGPS
logP	-2.2	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Acidic)	1.26	ChemAxon
pKa (Strongest Basic)	0.069	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	192.47 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	73.08 m³·mol⁻¹	ChemAxon
Polarizability	29.99 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0002-9613000000-3054f73e4c9456039ed6	2017-09-01	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-01ot-9521200000-1e6fc3c628d8ebd23b37	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
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-0ik9-7964000000-bce7ee60221f82790f35	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-0002-9400000000-05c1ae772c001a15a8c6	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Positive	splash10-0002-9200000000-743d2f19ea30c814c56a	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-0002-9210000000-f36c079a2869c6c7c63d	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-0002-9300000000-0cea344051256ed9d642	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-0002-9300000000-1295bb6a6dfffef31dd2	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-0002-9400000000-7125a3a52d3308d6b367	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-0fb9-9400000000-f93509061523b8f0b012	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-0002-9310000000-a910c200bfc66c8e1c46	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-0002-9000000000-1ff54bb8d71e1ea585f2	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-03fs-9380000000-2a0fbd1929733b4918d1	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-03di-1039000000-f0bd4ff644ac79937301	2021-09-20	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-0913000000-d17f1d77b992fc6e9f04	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0udi-0900000000-efbdb918f50ba610575d	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0udi-2900000000-cf070bd16aacd3dcb6fb	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0imi-6509000000-d931cb1dcaeba678220c	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0fbc-9300000000-e596281ec38113a9653c	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9100000000-1caa46ecd17db343ddd3	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-0900000000-ac450658003af6c0a109	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0udi-0900000000-448bfe6677d2f8fe1f3c	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0udi-1900000000-10c12403e596a9b5bf0a	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-3009000000-8a668987618bcd1531e7	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-9000000000-4b2bf772bc8415c9f24c	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9201000000-907dd40cbb70b7a5c62d	2021-09-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-29	View Spectrum

Chromatographic Retention Times and Retention Indices

Retention Times

Chromatography Type	Technique	Column	Deposition Date	Retention Time (s)
Liquid Chromatography	HILIC	Waters Acquity UPLC-BEH Amide column (eluted)	2025-10-23	556.9
Liquid Chromatography	HILIC	Accucore 150 Amide HILIC (eluted)	2025-10-23	407.7
Liquid Chromatography	Reversed-phase	Hypersil Gold 1.9 µm C18 (void)	2025-10-23	64.9
Liquid Chromatography	Reversed-phase	Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) (eluted)	2025-10-23	259.3
Liquid Chromatography	Reversed-phase	XBridge C18 3.5u 2.1x50 mm (eluted)	2025-10-23	331.7
Liquid Chromatography	Reversed-phase	Ascentis Express C18 (eluted)	2025-10-23	255.0
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-23	403.6
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (eluted)	2025-10-23	849.2
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC (eluted)	2025-10-23	789.4
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-23	148.8
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (eluted)	2025-10-23	442.5
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-23	164.9
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-23	37.5
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (eluted)	2025-10-23	460.8
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (eluted)	2025-10-23	917.3
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (void)	2025-10-23	56.9
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-23	271.0
Liquid Chromatography	Reversed-phase	Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex (eluted)	2025-10-23	628.7
Liquid Chromatography	Reversed-phase	Waters Atlantis T3 (2.1 x 150 mm, 5 um) (eluted)	2025-10-23	561.4

Retention Indices

Chromatography Type	Peak Label	SMILES	Stationary Phase	Deposition Date	Retention Index
Gas Chromatography	Xanthylic acid_TMS_1	C[Si](C)(C)O[C@@H]1[C@@H](COP(=O)(O)O)O[C@@H](N2C=NC3=C2[NH]C(=O)[NH]C3=O)[C@@H]1O	standard non polar	2025-10-23	2424.33
Gas Chromatography	Xanthylic acid_TMS_2	C[Si](C)(C)O[C@@H]1[C@H](O)[C@@H](COP(=O)(O)O)O[C@H]1N1C=NC2=C1[NH]C(=O)[NH]C2=O	standard non polar	2025-10-23	2443.79
Gas Chromatography	Xanthylic acid_TMS_3	C[Si](C)(C)OP(=O)(O)OC[C@H]1O[C@@H](N2C=NC3=C2[NH]C(=O)[NH]C3=O)[C@H](O)[C@@H]1O	standard non polar	2025-10-23	1590.19
Gas Chromatography	Xanthylic acid_TMS_4	C[Si](C)(C)N1C(=O)[NH]C(=O)C2=C1N([C@@H]1O[C@H](COP(=O)(O)O)[C@@H](O)[C@H]1O)C=N2	standard non polar	2025-10-23	2588.4
Gas Chromatography	Xanthylic acid_TMS_5	C[Si](C)(C)N1C(=O)[NH]C2=C(N=CN2[C@@H]2O[C@H](COP(=O)(O)O)[C@@H](O)[C@H]2O)C1=O	standard non polar	2025-10-23	2859.68
Gas Chromatography	Xanthylic acid_TMS_6	C[Si](C)(C)O[C@@H]1[C@@H](COP(=O)(O)O)O[C@@H](N2C=NC3=C2[NH]C(=O)[NH]C3=O)[C@@H]1O[Si](C)(C)C	standard non polar	2025-10-23	2301.92
Gas Chromatography	Xanthylic acid_TMS_7	C[Si](C)(C)O[C@@H]1[C@@H](COP(=O)(O)O[Si](C)(C)C)O[C@@H](N2C=NC3=C2[NH]C(=O)[NH]C3=O)[C@@H]1O	standard non polar	2025-10-23	1078.9
Gas Chromatography	Xanthylic acid_TMS_8	C[Si](C)(C)O[C@@H]1[C@@H](COP(=O)(O)O)O[C@@H](N2C=NC3=C2[NH]C(=O)N([Si](C)(C)C)C3=O)[C@@H]1O	standard non polar	2025-10-23	2083.59
Gas Chromatography	Xanthylic acid_TMS_9	C[Si](C)(C)O[C@@H]1[C@@H](COP(=O)(O)O)O[C@@H](N2C=NC3=C2N([Si](C)(C)C)C(=O)[NH]C3=O)[C@@H]1O	standard non polar	2025-10-23	1585.65
Gas Chromatography	Xanthylic acid_TMS_10	C[Si](C)(C)O[C@@H]1[C@H](O)[C@@H](COP(=O)(O)O[Si](C)(C)C)O[C@H]1N1C=NC2=C1[NH]C(=O)[NH]C2=O	standard non polar	2025-10-23	1387.31
Gas Chromatography	Xanthylic acid_TMS_11	C[Si](C)(C)O[C@@H]1[C@H](O)[C@@H](COP(=O)(O)O)O[C@H]1N1C=NC2=C1[NH]C(=O)N([Si](C)(C)C)C2=O	standard non polar	2025-10-23	1645.11
Gas Chromatography	Xanthylic acid_TMS_12	C[Si](C)(C)O[C@@H]1[C@H](O)[C@@H](COP(=O)(O)O)O[C@H]1N1C=NC2=C1N([Si](C)(C)C)C(=O)[NH]C2=O	standard non polar	2025-10-23	2569.0
Gas Chromatography	Xanthylic acid_TMS_13	C[Si](C)(C)OP(=O)(OC[C@H]1O[C@@H](N2C=NC3=C2[NH]C(=O)[NH]C3=O)[C@H](O)[C@@H]1O)O[Si](C)(C)C	standard non polar	2025-10-23	1554.77
Gas Chromatography	Xanthylic acid_TMS_14	C[Si](C)(C)OP(=O)(O)OC[C@H]1O[C@@H](N2C=NC3=C2[NH]C(=O)N([Si](C)(C)C)C3=O)[C@H](O)[C@@H]1O	standard non polar	2025-10-23	2026.5
Gas Chromatography	Xanthylic acid_TMS_15	C[Si](C)(C)OP(=O)(O)OC[C@H]1O[C@@H](N2C=NC3=C2N([Si](C)(C)C)C(=O)[NH]C3=O)[C@H](O)[C@@H]1O	standard non polar	2025-10-23	2137.93
Gas Chromatography	Xanthylic acid_TMS_16	C[Si](C)(C)N1C(=O)C2=C(N([C@@H]3O[C@H](COP(=O)(O)O)[C@@H](O)[C@H]3O)C=N2)N([Si](C)(C)C)C1=O	standard non polar	2025-10-23	2028.71
Gas Chromatography	Xanthylic acid_TMS_17	C[Si](C)(C)O[C@@H]1[C@@H](COP(=O)(O)O[Si](C)(C)C)O[C@@H](N2C=NC3=C2[NH]C(=O)[NH]C3=O)[C@@H]1O[Si](C)(C)C	standard non polar	2025-10-23	1461.88
Gas Chromatography	Xanthylic acid_TMS_18	C[Si](C)(C)O[C@@H]1[C@@H](COP(=O)(O)O)O[C@@H](N2C=NC3=C2[NH]C(=O)N([Si](C)(C)C)C3=O)[C@@H]1O[Si](C)(C)C	standard non polar	2025-10-23	1058.52
Gas Chromatography	Xanthylic acid_TMS_19	C[Si](C)(C)O[C@@H]1[C@@H](COP(=O)(O)O)O[C@@H](N2C=NC3=C2N([Si](C)(C)C)C(=O)[NH]C3=O)[C@@H]1O[Si](C)(C)C	standard non polar	2025-10-23	783.728
Gas Chromatography	Xanthylic acid_TMS_20	C[Si](C)(C)O[C@@H]1[C@@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)O[C@@H](N2C=NC3=C2[NH]C(=O)[NH]C3=O)[C@@H]1O	standard non polar	2025-10-23	1685.5
Gas Chromatography	Xanthylic acid_TMS_21	C[Si](C)(C)O[C@@H]1[C@@H](COP(=O)(O)O[Si](C)(C)C)O[C@@H](N2C=NC3=C2[NH]C(=O)N([Si](C)(C)C)C3=O)[C@@H]1O	standard non polar	2025-10-23	3294.18
Gas Chromatography	Xanthylic acid_TMS_22	C[Si](C)(C)O[C@@H]1[C@@H](COP(=O)(O)O[Si](C)(C)C)O[C@@H](N2C=NC3=C2N([Si](C)(C)C)C(=O)[NH]C3=O)[C@@H]1O	standard non polar	2025-10-23	2003.09
Gas Chromatography	Xanthylic acid_TMS_23	C[Si](C)(C)O[C@@H]1[C@@H](COP(=O)(O)O)O[C@@H](N2C=NC3=C2N([Si](C)(C)C)C(=O)N([Si](C)(C)C)C3=O)[C@@H]1O	standard non polar	2025-10-23	2068.55
Gas Chromatography	Xanthylic acid_TMS_24	C[Si](C)(C)O[C@@H]1[C@H](O)[C@@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)O[C@H]1N1C=NC2=C1[NH]C(=O)[NH]C2=O	standard non polar	2025-10-23	1542.63
Gas Chromatography	Xanthylic acid_TMS_25	C[Si](C)(C)O[C@@H]1[C@H](O)[C@@H](COP(=O)(O)O[Si](C)(C)C)O[C@H]1N1C=NC2=C1[NH]C(=O)N([Si](C)(C)C)C2=O	standard non polar	2025-10-23	2451.05
Gas Chromatography	Xanthylic acid_TMS_26	C[Si](C)(C)O[C@@H]1[C@H](O)[C@@H](COP(=O)(O)O[Si](C)(C)C)O[C@H]1N1C=NC2=C1N([Si](C)(C)C)C(=O)[NH]C2=O	standard non polar	2025-10-23	2617.09
Gas Chromatography	Xanthylic acid_TMS_27	C[Si](C)(C)O[C@@H]1[C@H](O)[C@@H](COP(=O)(O)O)O[C@H]1N1C=NC2=C1N([Si](C)(C)C)C(=O)N([Si](C)(C)C)C2=O	standard non polar	2025-10-23	2066.67
Gas Chromatography	Xanthylic acid_TMS_28	C[Si](C)(C)OP(=O)(OC[C@H]1O[C@@H](N2C=NC3=C2[NH]C(=O)N([Si](C)(C)C)C3=O)[C@H](O)[C@@H]1O)O[Si](C)(C)C	standard non polar	2025-10-23	2360.27
Gas Chromatography	Xanthylic acid_TMS_29	C[Si](C)(C)OP(=O)(OC[C@H]1O[C@@H](N2C=NC3=C2N([Si](C)(C)C)C(=O)[NH]C3=O)[C@H](O)[C@@H]1O)O[Si](C)(C)C	standard non polar	2025-10-23	1837.69
Gas Chromatography	Xanthylic acid_TMS_30	C[Si](C)(C)OP(=O)(O)OC[C@H]1O[C@@H](N2C=NC3=C2N([Si](C)(C)C)C(=O)N([Si](C)(C)C)C3=O)[C@H](O)[C@@H]1O	standard non polar	2025-10-23	853.735
Gas Chromatography	Xanthylic acid_TMS_31	C[Si](C)(C)O[C@@H]1[C@@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)O[C@@H](N2C=NC3=C2[NH]C(=O)[NH]C3=O)[C@@H]1O[Si](C)(C)C	standard non polar	2025-10-23	1275.62
Gas Chromatography	Xanthylic acid_TMS_32	C[Si](C)(C)O[C@@H]1[C@@H](COP(=O)(O)O[Si](C)(C)C)O[C@@H](N2C=NC3=C2[NH]C(=O)N([Si](C)(C)C)C3=O)[C@@H]1O[Si](C)(C)C	standard non polar	2025-10-23	1560.2
Gas Chromatography	Xanthylic acid_TMS_33	C[Si](C)(C)O[C@@H]1[C@@H](COP(=O)(O)O[Si](C)(C)C)O[C@@H](N2C=NC3=C2N([Si](C)(C)C)C(=O)[NH]C3=O)[C@@H]1O[Si](C)(C)C	standard non polar	2025-10-23	1139.27
Gas Chromatography	Xanthylic acid_TMS_34	C[Si](C)(C)O[C@@H]1[C@@H](COP(=O)(O)O)O[C@@H](N2C=NC3=C2N([Si](C)(C)C)C(=O)N([Si](C)(C)C)C3=O)[C@@H]1O[Si](C)(C)C	standard non polar	2025-10-23	2332.44
Gas Chromatography	Xanthylic acid_TMS_35	C[Si](C)(C)O[C@@H]1[C@@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)O[C@@H](N2C=NC3=C2[NH]C(=O)N([Si](C)(C)C)C3=O)[C@@H]1O	standard non polar	2025-10-23	1500.17
Gas Chromatography	Xanthylic acid_TMS_36	C[Si](C)(C)O[C@@H]1[C@@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)O[C@@H](N2C=NC3=C2N([Si](C)(C)C)C(=O)[NH]C3=O)[C@@H]1O	standard non polar	2025-10-23	1940.95
Gas Chromatography	Xanthylic acid_TMS_37	C[Si](C)(C)O[C@@H]1[C@@H](COP(=O)(O)O[Si](C)(C)C)O[C@@H](N2C=NC3=C2N([Si](C)(C)C)C(=O)N([Si](C)(C)C)C3=O)[C@@H]1O	standard non polar	2025-10-23	1397.84
Gas Chromatography	Xanthylic acid_TMS_38	C[Si](C)(C)O[C@@H]1[C@H](O)[C@@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)O[C@H]1N1C=NC2=C1[NH]C(=O)N([Si](C)(C)C)C2=O	standard non polar	2025-10-23	1630.93
Gas Chromatography	Xanthylic acid_TMS_39	C[Si](C)(C)O[C@@H]1[C@H](O)[C@@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)O[C@H]1N1C=NC2=C1N([Si](C)(C)C)C(=O)[NH]C2=O	standard non polar	2025-10-23	1402.87
Gas Chromatography	Xanthylic acid_TMS_40	C[Si](C)(C)O[C@@H]1[C@H](O)[C@@H](COP(=O)(O)O[Si](C)(C)C)O[C@H]1N1C=NC2=C1N([Si](C)(C)C)C(=O)N([Si](C)(C)C)C2=O	standard non polar	2025-10-23	1843.25
Gas Chromatography	Xanthylic acid_TMS_41	C[Si](C)(C)OP(=O)(OC[C@H]1O[C@@H](N2C=NC3=C2N([Si](C)(C)C)C(=O)N([Si](C)(C)C)C3=O)[C@H](O)[C@@H]1O)O[Si](C)(C)C	standard non polar	2025-10-23	2507.94
Gas Chromatography	Xanthylic acid_TMS_42	C[Si](C)(C)O[C@@H]1[C@@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)O[C@@H](N2C=NC3=C2[NH]C(=O)N([Si](C)(C)C)C3=O)[C@@H]1O[Si](C)(C)C	standard non polar	2025-10-23	1759.3
Gas Chromatography	Xanthylic acid_TMS_43	C[Si](C)(C)O[C@@H]1[C@@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)O[C@@H](N2C=NC3=C2N([Si](C)(C)C)C(=O)[NH]C3=O)[C@@H]1O[Si](C)(C)C	standard non polar	2025-10-23	1917.39
Gas Chromatography	Xanthylic acid_TMS_44	C[Si](C)(C)O[C@@H]1[C@@H](COP(=O)(O)O[Si](C)(C)C)O[C@@H](N2C=NC3=C2N([Si](C)(C)C)C(=O)N([Si](C)(C)C)C3=O)[C@@H]1O[Si](C)(C)C	standard non polar	2025-10-23	1963.0
Gas Chromatography	Xanthylic acid_TMS_45	C[Si](C)(C)O[C@@H]1[C@@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)O[C@@H](N2C=NC3=C2N([Si](C)(C)C)C(=O)N([Si](C)(C)C)C3=O)[C@@H]1O	standard non polar	2025-10-23	4119.89
Gas Chromatography	Xanthylic acid_TMS_46	C[Si](C)(C)O[C@@H]1[C@H](O)[C@@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)O[C@H]1N1C=NC2=C1N([Si](C)(C)C)C(=O)N([Si](C)(C)C)C2=O	standard non polar	2025-10-23	1964.71
Gas Chromatography	Xanthylic acid_TMS_47	C[Si](C)(C)O[C@@H]1[C@@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)O[C@@H](N2C=NC3=C2N([Si](C)(C)C)C(=O)N([Si](C)(C)C)C3=O)[C@@H]1O[Si](C)(C)C	standard non polar	2025-10-23	1396.0
Gas Chromatography	Xanthylic acid_TMS_1	C[Si](C)(C)O[C@@H]1[C@@H](COP(=O)(O)O)O[C@@H](N2C=NC3=C2[NH]C(=O)[NH]C3=O)[C@@H]1O	standard polar	2025-10-23	2112.1
Gas Chromatography	Xanthylic acid_TMS_2	C[Si](C)(C)O[C@@H]1[C@H](O)[C@@H](COP(=O)(O)O)O[C@H]1N1C=NC2=C1[NH]C(=O)[NH]C2=O	standard polar	2025-10-23	2087.05
Gas Chromatography	Xanthylic acid_TMS_3	C[Si](C)(C)OP(=O)(O)OC[C@H]1O[C@@H](N2C=NC3=C2[NH]C(=O)[NH]C3=O)[C@H](O)[C@@H]1O	standard polar	2025-10-23	2500.82
Gas Chromatography	Xanthylic acid_TMS_4	C[Si](C)(C)N1C(=O)[NH]C(=O)C2=C1N([C@@H]1O[C@H](COP(=O)(O)O)[C@@H](O)[C@H]1O)C=N2	standard polar	2025-10-23	2073.76
Gas Chromatography	Xanthylic acid_TMS_5	C[Si](C)(C)N1C(=O)[NH]C2=C(N=CN2[C@@H]2O[C@H](COP(=O)(O)O)[C@@H](O)[C@H]2O)C1=O	standard polar	2025-10-23	2258.75
Gas Chromatography	Xanthylic acid_TMS_6	C[Si](C)(C)O[C@@H]1[C@@H](COP(=O)(O)O)O[C@@H](N2C=NC3=C2[NH]C(=O)[NH]C3=O)[C@@H]1O[Si](C)(C)C	standard polar	2025-10-23	1564.39
Gas Chromatography	Xanthylic acid_TMS_7	C[Si](C)(C)O[C@@H]1[C@@H](COP(=O)(O)O[Si](C)(C)C)O[C@@H](N2C=NC3=C2[NH]C(=O)[NH]C3=O)[C@@H]1O	standard polar	2025-10-23	2305.97
Gas Chromatography	Xanthylic acid_TMS_8	C[Si](C)(C)O[C@@H]1[C@@H](COP(=O)(O)O)O[C@@H](N2C=NC3=C2[NH]C(=O)N([Si](C)(C)C)C3=O)[C@@H]1O	standard polar	2025-10-23	2502.26
Gas Chromatography	Xanthylic acid_TMS_9	C[Si](C)(C)O[C@@H]1[C@@H](COP(=O)(O)O)O[C@@H](N2C=NC3=C2N([Si](C)(C)C)C(=O)[NH]C3=O)[C@@H]1O	standard polar	2025-10-23	2537.52
Gas Chromatography	Xanthylic acid_TMS_10	C[Si](C)(C)O[C@@H]1[C@H](O)[C@@H](COP(=O)(O)O[Si](C)(C)C)O[C@H]1N1C=NC2=C1[NH]C(=O)[NH]C2=O	standard polar	2025-10-23	1679.79
Gas Chromatography	Xanthylic acid_TMS_11	C[Si](C)(C)O[C@@H]1[C@H](O)[C@@H](COP(=O)(O)O)O[C@H]1N1C=NC2=C1[NH]C(=O)N([Si](C)(C)C)C2=O	standard polar	2025-10-23	2382.97
Gas Chromatography	Xanthylic acid_TMS_12	C[Si](C)(C)O[C@@H]1[C@H](O)[C@@H](COP(=O)(O)O)O[C@H]1N1C=NC2=C1N([Si](C)(C)C)C(=O)[NH]C2=O	standard polar	2025-10-23	1933.64
Gas Chromatography	Xanthylic acid_TMS_13	C[Si](C)(C)OP(=O)(OC[C@H]1O[C@@H](N2C=NC3=C2[NH]C(=O)[NH]C3=O)[C@H](O)[C@@H]1O)O[Si](C)(C)C	standard polar	2025-10-23	2176.85
Gas Chromatography	Xanthylic acid_TMS_14	C[Si](C)(C)OP(=O)(O)OC[C@H]1O[C@@H](N2C=NC3=C2[NH]C(=O)N([Si](C)(C)C)C3=O)[C@H](O)[C@@H]1O	standard polar	2025-10-23	2501.72
Gas Chromatography	Xanthylic acid_TMS_15	C[Si](C)(C)OP(=O)(O)OC[C@H]1O[C@@H](N2C=NC3=C2N([Si](C)(C)C)C(=O)[NH]C3=O)[C@H](O)[C@@H]1O	standard polar	2025-10-23	2733.96
Gas Chromatography	Xanthylic acid_TMS_16	C[Si](C)(C)N1C(=O)C2=C(N([C@@H]3O[C@H](COP(=O)(O)O)[C@@H](O)[C@H]3O)C=N2)N([Si](C)(C)C)C1=O	standard polar	2025-10-23	1102.29
Gas Chromatography	Xanthylic acid_TMS_17	C[Si](C)(C)O[C@@H]1[C@@H](COP(=O)(O)O[Si](C)(C)C)O[C@@H](N2C=NC3=C2[NH]C(=O)[NH]C3=O)[C@@H]1O[Si](C)(C)C	standard polar	2025-10-23	1902.02
Gas Chromatography	Xanthylic acid_TMS_18	C[Si](C)(C)O[C@@H]1[C@@H](COP(=O)(O)O)O[C@@H](N2C=NC3=C2[NH]C(=O)N([Si](C)(C)C)C3=O)[C@@H]1O[Si](C)(C)C	standard polar	2025-10-23	2558.48
Gas Chromatography	Xanthylic acid_TMS_19	C[Si](C)(C)O[C@@H]1[C@@H](COP(=O)(O)O)O[C@@H](N2C=NC3=C2N([Si](C)(C)C)C(=O)[NH]C3=O)[C@@H]1O[Si](C)(C)C	standard polar	2025-10-23	2592.39
Gas Chromatography	Xanthylic acid_TMS_20	C[Si](C)(C)O[C@@H]1[C@@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)O[C@@H](N2C=NC3=C2[NH]C(=O)[NH]C3=O)[C@@H]1O	standard polar	2025-10-23	1959.8
Gas Chromatography	Xanthylic acid_TMS_21	C[Si](C)(C)O[C@@H]1[C@@H](COP(=O)(O)O[Si](C)(C)C)O[C@@H](N2C=NC3=C2[NH]C(=O)N([Si](C)(C)C)C3=O)[C@@H]1O	standard polar	2025-10-23	1672.61
Gas Chromatography	Xanthylic acid_TMS_22	C[Si](C)(C)O[C@@H]1[C@@H](COP(=O)(O)O[Si](C)(C)C)O[C@@H](N2C=NC3=C2N([Si](C)(C)C)C(=O)[NH]C3=O)[C@@H]1O	standard polar	2025-10-23	2739.42
Gas Chromatography	Xanthylic acid_TMS_23	C[Si](C)(C)O[C@@H]1[C@@H](COP(=O)(O)O)O[C@@H](N2C=NC3=C2N([Si](C)(C)C)C(=O)N([Si](C)(C)C)C3=O)[C@@H]1O	standard polar	2025-10-23	1866.14
Gas Chromatography	Xanthylic acid_TMS_24	C[Si](C)(C)O[C@@H]1[C@H](O)[C@@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)O[C@H]1N1C=NC2=C1[NH]C(=O)[NH]C2=O	standard polar	2025-10-23	2309.44
Gas Chromatography	Xanthylic acid_TMS_25	C[Si](C)(C)O[C@@H]1[C@H](O)[C@@H](COP(=O)(O)O[Si](C)(C)C)O[C@H]1N1C=NC2=C1[NH]C(=O)N([Si](C)(C)C)C2=O	standard polar	2025-10-23	2750.95
Gas Chromatography	Xanthylic acid_TMS_26	C[Si](C)(C)O[C@@H]1[C@H](O)[C@@H](COP(=O)(O)O[Si](C)(C)C)O[C@H]1N1C=NC2=C1N([Si](C)(C)C)C(=O)[NH]C2=O	standard polar	2025-10-23	2292.9
Gas Chromatography	Xanthylic acid_TMS_27	C[Si](C)(C)O[C@@H]1[C@H](O)[C@@H](COP(=O)(O)O)O[C@H]1N1C=NC2=C1N([Si](C)(C)C)C(=O)N([Si](C)(C)C)C2=O	standard polar	2025-10-23	897.396
Gas Chromatography	Xanthylic acid_TMS_28	C[Si](C)(C)OP(=O)(OC[C@H]1O[C@@H](N2C=NC3=C2[NH]C(=O)N([Si](C)(C)C)C3=O)[C@H](O)[C@@H]1O)O[Si](C)(C)C	standard polar	2025-10-23	2179.3
Gas Chromatography	Xanthylic acid_TMS_29	C[Si](C)(C)OP(=O)(OC[C@H]1O[C@@H](N2C=NC3=C2N([Si](C)(C)C)C(=O)[NH]C3=O)[C@H](O)[C@@H]1O)O[Si](C)(C)C	standard polar	2025-10-23	1937.76
Gas Chromatography	Xanthylic acid_TMS_30	C[Si](C)(C)OP(=O)(O)OC[C@H]1O[C@@H](N2C=NC3=C2N([Si](C)(C)C)C(=O)N([Si](C)(C)C)C3=O)[C@H](O)[C@@H]1O	standard polar	2025-10-23	1180.79
Gas Chromatography	Xanthylic acid_TMS_31	C[Si](C)(C)O[C@@H]1[C@@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)O[C@@H](N2C=NC3=C2[NH]C(=O)[NH]C3=O)[C@@H]1O[Si](C)(C)C	standard polar	2025-10-23	576.745
Gas Chromatography	Xanthylic acid_TMS_32	C[Si](C)(C)O[C@@H]1[C@@H](COP(=O)(O)O[Si](C)(C)C)O[C@@H](N2C=NC3=C2[NH]C(=O)N([Si](C)(C)C)C3=O)[C@@H]1O[Si](C)(C)C	standard polar	2025-10-23	2452.71
Gas Chromatography	Xanthylic acid_TMS_33	C[Si](C)(C)O[C@@H]1[C@@H](COP(=O)(O)O[Si](C)(C)C)O[C@@H](N2C=NC3=C2N([Si](C)(C)C)C(=O)[NH]C3=O)[C@@H]1O[Si](C)(C)C	standard polar	2025-10-23	1753.59
Gas Chromatography	Xanthylic acid_TMS_34	C[Si](C)(C)O[C@@H]1[C@@H](COP(=O)(O)O)O[C@@H](N2C=NC3=C2N([Si](C)(C)C)C(=O)N([Si](C)(C)C)C3=O)[C@@H]1O[Si](C)(C)C	standard polar	2025-10-23	2506.55
Gas Chromatography	Xanthylic acid_TMS_35	C[Si](C)(C)O[C@@H]1[C@@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)O[C@@H](N2C=NC3=C2[NH]C(=O)N([Si](C)(C)C)C3=O)[C@@H]1O	standard polar	2025-10-23	2140.51
Gas Chromatography	Xanthylic acid_TMS_36	C[Si](C)(C)O[C@@H]1[C@@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)O[C@@H](N2C=NC3=C2N([Si](C)(C)C)C(=O)[NH]C3=O)[C@@H]1O	standard polar	2025-10-23	1655.18
Gas Chromatography	Xanthylic acid_TMS_37	C[Si](C)(C)O[C@@H]1[C@@H](COP(=O)(O)O[Si](C)(C)C)O[C@@H](N2C=NC3=C2N([Si](C)(C)C)C(=O)N([Si](C)(C)C)C3=O)[C@@H]1O	standard polar	2025-10-23	1388.84
Gas Chromatography	Xanthylic acid_TMS_38	C[Si](C)(C)O[C@@H]1[C@H](O)[C@@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)O[C@H]1N1C=NC2=C1[NH]C(=O)N([Si](C)(C)C)C2=O	standard polar	2025-10-23	2640.33
Gas Chromatography	Xanthylic acid_TMS_39	C[Si](C)(C)O[C@@H]1[C@H](O)[C@@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)O[C@H]1N1C=NC2=C1N([Si](C)(C)C)C(=O)[NH]C2=O	standard polar	2025-10-23	2632.99
Gas Chromatography	Xanthylic acid_TMS_40	C[Si](C)(C)O[C@@H]1[C@H](O)[C@@H](COP(=O)(O)O[Si](C)(C)C)O[C@H]1N1C=NC2=C1N([Si](C)(C)C)C(=O)N([Si](C)(C)C)C2=O	standard polar	2025-10-23	1312.67
Gas Chromatography	Xanthylic acid_TMS_41	C[Si](C)(C)OP(=O)(OC[C@H]1O[C@@H](N2C=NC3=C2N([Si](C)(C)C)C(=O)N([Si](C)(C)C)C3=O)[C@H](O)[C@@H]1O)O[Si](C)(C)C	standard polar	2025-10-23	2602.85
Gas Chromatography	Xanthylic acid_TMS_42	C[Si](C)(C)O[C@@H]1[C@@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)O[C@@H](N2C=NC3=C2[NH]C(=O)N([Si](C)(C)C)C3=O)[C@@H]1O[Si](C)(C)C	standard polar	2025-10-23	1662.42
Gas Chromatography	Xanthylic acid_TMS_43	C[Si](C)(C)O[C@@H]1[C@@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)O[C@@H](N2C=NC3=C2N([Si](C)(C)C)C(=O)[NH]C3=O)[C@@H]1O[Si](C)(C)C	standard polar	2025-10-23	886.707
Gas Chromatography	Xanthylic acid_TMS_44	C[Si](C)(C)O[C@@H]1[C@@H](COP(=O)(O)O[Si](C)(C)C)O[C@@H](N2C=NC3=C2N([Si](C)(C)C)C(=O)N([Si](C)(C)C)C3=O)[C@@H]1O[Si](C)(C)C	standard polar	2025-10-23	2539.01
Gas Chromatography	Xanthylic acid_TMS_45	C[Si](C)(C)O[C@@H]1[C@@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)O[C@@H](N2C=NC3=C2N([Si](C)(C)C)C(=O)N([Si](C)(C)C)C3=O)[C@@H]1O	standard polar	2025-10-23	2274.49
Gas Chromatography	Xanthylic acid_TMS_46	C[Si](C)(C)O[C@@H]1[C@H](O)[C@@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)O[C@H]1N1C=NC2=C1N([Si](C)(C)C)C(=O)N([Si](C)(C)C)C2=O	standard polar	2025-10-23	1925.43
Gas Chromatography	Xanthylic acid_TMS_47	C[Si](C)(C)O[C@@H]1[C@@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)O[C@@H](N2C=NC3=C2N([Si](C)(C)C)C(=O)N([Si](C)(C)C)C3=O)[C@@H]1O[Si](C)(C)C	standard polar	2025-10-23	1913.16

Biological Properties

Cellular Locations

Cytoplasm

Biospecimen Locations

Feces

Tissue Locations

Not Available

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
MMDBp0192133	Hypoxanthine-guanine phosphoribosyltransferase	Unknown	P00492	Homo sapiens
MMDBp0192235	GMP synthase [glutamine-hydrolyzing]	Unknown	P49915	Homo sapiens
MMDBp0192263	Bis(5'-nucleosyl)-tetraphosphatase [asymmetrical]	Unknown	P50583	Homo sapiens
MMDBp0192499	Inosine-5'-monophosphate dehydrogenase 2	Unknown	P12268	Homo sapiens
MMDBp0192501	Inosine-5'-monophosphate dehydrogenase 1	Unknown	P20839	Homo sapiens
MMDBp0193860	Cytosolic 5'-nucleotidase 3	Enzyme	Q9H0P0	Homo sapiens
MMDBp0193932	Cytosolic purine 5'-nucleotidase	Unknown	P49902	Homo sapiens
MMDBp0194183	Inosine-5'-monophosphate dehydrogenase	Enzyme	A4D0Z6	Homo sapiens

Human Pathways

Pathways

Name	SMPDB/PathBank

Microbial Pathways

Pathways

Name	SMPDB/PathBank	Species
Purine Nucleotides De Novo Biosynthesis		Escherichia coli Pseudomonas aeruginosa Escherichia coli SMS-3-5 Escherichia coli UTI89 Escherichia coli 55989 Escherichia coli SE11 Pseudomonas aeruginosa PA7 Escherichia coli CFT073 Pseudomonas stutzeri Klebsiella pneumoniae Pseudomonas fluorescens Pf-5 Salmonella enterica Shewanella denitrificans OS217 Megamonas hypermegale Pseudomonas fluorescens Pseudomonas putida Citrobacter koseri Proteus mirabilis Shigella boydii Shigella dysenteriae Shigella flexneri Shigella sonnei Vibrio vulnificus Corynebacterium diphtheriae Thiobacillus denitrificans Enterobacter cancerogenus Methylibium petroleiphilum Citrobacter youngae Shewanella denitrificans Escherichia albertii Citrobacter koseri ATCC BAA-895 Cronobacter sakazakii ATCC BAA-894 Enterobacter cloacae subsp. cloacae ATCC 13047 Escherichia coli E24377A Escherichia coli O127:H6 str. E2348/69 Escherichia coli UMN026 Escherichia fergusonii ATCC 35469 Escherichia coli ED1a Escherichia coli IAI39 Klebsiella pneumoniae subsp. pneumoniae MGH 78578 Escherichia coli 042 Edwardsiella tarda FL6-60 Proteus mirabilis HI4320 Pseudomonas putida KT2440 Pseudomonas fluorescens Pf0-1 Pseudomonas stutzeri A1501 Pseudomonas fluorescens SBW25 Pseudomonas putida GB-1 Salmonella enterica subsp. enterica serovar Typhimurium str. LT2 Salmonella enterica subsp. enterica serovar Newport str. SL254 Salmonella enterica subsp. enterica serovar Heidelberg str. SL476 Salmonella enterica subsp. enterica serovar Agona str. SL483 Salmonella enterica subsp. enterica serovar Dublin str. CT02021853 Shigella sonnei Ss046 Shigella flexneri 5 str. 8401 Vibrio parahaemolyticus RIMD 2210633 Yersinia enterocolitica subsp. enterocolitica 8081 Yersinia pseudotuberculosis IP 31758 Cedecea davisae Cedecea davisae DSM 4568 Citrobacter amalonaticus Citrobacter amalonaticus Y19 Citrobacter freundii Citrobacter youngae ATCC 29220 Enterobacter hormaechei Escherichia albertii TW07627 Klebsiella aerogenes Salmonella Salmonella enterica subsp. enterica serovar Typhimurium Trabulsiella guamensis Trabulsiella guamensis ATCC 49490 Edwardsiella tarda Edwardsiella tarda ATCC 23685 Hafnia alvei Hafnia alvei ATCC 51873 Morganella morganii Morganella morganii subsp. morganii KT Providencia stuartii ATCC 25827 Serratia marcescens subsp. marcescens Db11 Yersinia enterocolitica Yersinia pestis Yersinia pseudotuberculosis Plesiomonas shigelloides 302-73 Grimontia hollisae CIP 101886 Vibrio fluvialis Vibrio fluvialis PG41 Vibrio mimicus Dialister succinatiphilus Dialister succinatiphilus YIT 11850 Ralstonia eutropha H16 Vibrio cholerae M66-2 Vibrio cholerae O1 biovar El Tor str. N16961 Shewanella frigidimarina NCIMB 400 Candidatus Desulforudis audaxviator MP104C Corynebacterium diphtheriae NCTC 13129 Klebsiella aerogenes KCTC 2190 Acidovorax citrulli AAC00-1 Acidovorax sp. JS42 Acidovorax ebreus TPSY Rhodoferax ferrireducens T118 Burkholderia mallei ATCC 23344 Burkholderia pseudomallei 1710b Burkholderia mallei NCTC 10229 Burkholderia pseudomallei 1106a Citrobacter rodentium ICC168 Cronobacter turicensis z3032 Cupriavidus metallidurans CH34 Dickeya dadantii Ech703 Dickeya zeae Ech1591 Dickeya dadantii Ech586 Dickeya dadantii 3937 Edwardsiella ictaluri 93-146 Enterobacter sp. 638 Enterobacter cloacae SCF1 Erwinia billingiae Eb661 Ferrimonas balearica DSM 9799 Herminiimonas arsenicoxydans Klebsiella pneumoniae 342 Marinobacter aquaeolei VT8 Methylibium petroleiphilum PM1 Methylotenera mobilis JLW8 Chromobacterium violaceum ATCC 12472 Pantoea ananatis LMG 20103 Pectobacterium atrosepticum SCRI1043 Pectobacterium carotovorum subsp. carotovorum PC1 Photobacterium profundum SS9 Polaromonas sp. JS666 Pseudomonas syringae pv. tomato str. DC3000 Pseudomonas syringae pv. phaseolicola 1448A Pseudomonas syringae pv. syringae B728a Pseudomonas entomophila L48 Psychromonas ingrahamii 37 Ralstonia solanacearum GMI1000 Salmonella enterica subsp. enterica serovar Paratyphi A str. Shewanella oneidensis MR-1 Shewanella sp. ANA-3 Shewanella amazonensis SB2B Shewanella sp. W3-18-1 Shewanella baltica OS155 Shewanella loihica PV-4 Shewanella sediminis HAW-EB3 Shewanella pealeana ATCC 700345 Shewanella baltica OS195 Shewanella halifaxensis HAW-EB4 Shewanella woodyi ATCC 51908 Shewanella piezotolerans WP3 Shigella flexneri 2a str. 301 Thiobacillus denitrificans ATCC 25259 Tolumonas auensis DSM 9187 Variovorax paradoxus EPS Verminephrobacter eiseniae EF01-2 Vibrio vulnificus CMCP6 Vibrio vulnificus YJ016 Atlantibacter hermannii NBRC 105704 Klebsiella michiganensis KCTC 1686 Chania multitudinisentens RB-25
Purine Nucleotides De Novo Biosynthesis 2
Purine Ribonucleosides Degradation

Metabolic Reactions

Reactions

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

See All Associated Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference
MMDBr0018516	Inosinic acid	Xanthylic acid	Inosine-5'-monophosphate dehydrogenase	Dehydrogenation	PathBank	31602464
MMDBr0018520	L-Glutamine	L-Glutamic acid	GMP synthase [glutamine-hydrolyzing]	Synthesis	PathBank	31602464
MMDBr0019334	Xanthine	Xanthylic acid	Xanthine-guanine phosphoribosyltransferase	Transfer of a ribosyl group	PathBank	31602464
MMDBr0019845	Inosinic acid	Xanthylic acid	Putative inosine-5'-monophosphate dehydrogenase 1	Dehydrogenation	PathBank	31602464
MMDBr0019849	L-Glutamine	L-Glutamic acid	Unknown Protein		PathBank	31602464

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Proteobacteria	4	Human feces; Human sputum; Human ; Human unknown; Pig ; Human pleural fluid plaque; Human dental plaque; Human nasal swab; Human feces; pleural fluid plaque; bal; Cattle ; River trout ; Chicken ; Human subgingival plaque; Turkey ; Sheep ; Dog ; Lion	Unknown; Metabolic reconstruction
Bacteria/Eubacteria	Firmicutes	498	Human feces; Human pleural fluid plaque; Pig ; Human sputum; Human ; Human subgingival plaque; Human saliva; Human urine; Human mucosa; Human supragingival plaque; Cattle	Metabolic reconstruction
Bacteria/Eubacteria	Proteobacteria	509	Human feces; Human sputum; Human ; Human unknown; Pig ; Human pleural fluid plaque; Human dental plaque; Human nasal swab; Human feces; pleural fluid plaque; bal; Cattle ; River trout ; Chicken ; Human subgingival plaque; Turkey ; Sheep ; Dog ; Lion	Unknown; Metabolic reconstruction
Bacteria/Eubacteria	Actinobacteria	154	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; Cattle	Metabolic reconstruction
Bacteria/Eubacteria	Verrucomicrobia	3	Human ; Human feces	Metabolic reconstruction
Bacteria/Eubacteria	Bacteroidetes	132	Human feces; Human appendix biopsy; Human ; Human saliva; Human gastric fluid; Human urine; Human subgingival plaque; Human supragingival plaque	Metabolic reconstruction
Bacteria/Eubacteria	Synergistetes	3	Human feces	Metabolic reconstruction
Bacteria	Firmicutes	2	Human feces; Human pleural fluid plaque; Pig ; Human sputum; Human ; Human subgingival plaque; Human saliva; Human urine; Human mucosa; Human supragingival plaque; Cattle	Metabolic reconstruction
Bacteria/Eubacteria	Spirochaetes	15	Human feces; Human ; Pig	Metabolic reconstruction
Archaea	Thaumarchaeota	1		Metabolic reconstruction
Bacteria/Eubacteria	Fusobacteria	20	Human feces; Human	Metabolic reconstruction
Archaea	Euryarchaeota	5		Metabolic reconstruction
Bacteria/Eubacteria	Candidatus melainabacteria	1	Human feces	Metabolic reconstruction
Bacteria/Eubacteria	Tenericutes	8	Human feces; Human	Metabolic reconstruction
Bacteria/Eubacteria	Planctomycetes	2	Human feces	Metabolic reconstruction
Archaea	Crenarchaeota	1		Metabolic reconstruction
Bacteria	Synergistetes	1	Human feces	Metabolic reconstruction
Bacteria/Eubacteria	Chloroflexi	5
Bacteria/Eubacteria	Deinococcus-thermus	5
Bacteria/Eubacteria	Aquificae	3
Eukaryota/Fungi	Ascomycota	28	Human feces; Human saliva; Human supragingival plaque	Unknown
Bacteria/Eubacteria	Chlorobi	10
Eukaryota/Fungi	Basidiomycota	4
Archaea/Archaea	Euryarchaeota	34		Metabolic reconstruction
Archaea/Archaea	Korarchaeota	1
Archaea/Archaea	Thaumarchaeota	1		Metabolic reconstruction
Eukaryota/Fungi	Chytridiomycota	1
Eukaryota/Fungi	Microsporidia	2
Bacteria/Eubacteria	Acidobacteria	1
Bacteria/Eubacteria	Chlamydiae	10	Human ; Sheep ; Cat
Bacteria/Eubacteria	Dictyoglomi	1
Bacteria/Eubacteria	Elusimicrobia	1
Bacteria/Eubacteria	Cyanobacteria	25
Archaea/Archaea	Crenarchaeota	12		Metabolic reconstruction
Bacteria	nah	1
Bacteria/Eubacteria	Thermotogae	6
Bacteria/Eubacteria	Nitrospirae	1
Bacteria/Eubacteria	Gemmatimonadetes	1
Bacteria	Tenericutes	1	Human feces; Human	Metabolic reconstruction

Exposure Sources

Other Exposures

Source Type	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Feces	Detected but not Quantified									HMDB

External Links

HMDB ID

HMDB0001554

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

XANTHOSINE-5-PHOSPHATE

BiGG ID

35623

Wikipedia Link

Xanthosine monophosphate

METLIN ID

Not Available

PubChem Compound

73323

PDB ID

Not Available

ChEBI ID

15652

Food Biomarker Ontology

Not Available

CMMC Knowledgebase

Not Available

General References

Hedstrom L: IMP dehydrogenase: mechanism of action and inhibition. Curr Med Chem. 1999 Jul;6(7):545-60. [PubMed:10390600 ]
Jayaram HN, Cooney DA, Grusch M, Krupitza G: Consequences of IMP dehydrogenase inhibition, and its relationship to cancer and apoptosis. Curr Med Chem. 1999 Jul;6(7):561-74. [PubMed:10390601 ]
Franchetti P, Grifantini M: Nucleoside and non-nucleoside IMP dehydrogenase inhibitors as antitumor and antiviral agents. Curr Med Chem. 1999 Jul;6(7):599-614. [PubMed:10390603 ]
Minakawa N, Matsuda A: Mechanism-based design of inosine 5-monophosphate dehydrogenase inhibitors: synthesis and biological activities of 5-ethynyl-1-beta-D-ribofuranosylimidazole-4-carboxamide (EICAR) and its derivatives. Curr Med Chem. 1999 Jul;6(7):615-28. [PubMed:10390604 ]
Pitera JW, Munagala NR, Wang CC, Kollman PA: Understanding substrate specificity in human and parasite phosphoribosyltransferases through calculation and experiment. Biochemistry. 1999 Aug 10;38(32):10298-306. doi: 10.1021/bi990250w. [PubMed:10441123 ]
Heroux A, White EL, Ross LJ, Borhani DW: Crystal structures of the Toxoplasma gondii hypoxanthine-guanine phosphoribosyltransferase-GMP and -IMP complexes: comparison of purine binding interactions with the XMP complex. Biochemistry. 1999 Nov 2;38(44):14485-94. doi: 10.1021/bi990507q. [PubMed:10545170 ]
Heroux A, White EL, Ross LJ, Davis RL, Borhani DW: Crystal structure of Toxoplasma gondii hypoxanthine-guanine phosphoribosyltransferase with XMP, pyrophosphate, and two Mg(2+) ions bound: insights into the catalytic mechanism. Biochemistry. 1999 Nov 2;38(44):14495-506. doi: 10.1021/bi990508i. [PubMed:10545171 ]
Digits JA, Hedstrom L: Species-specific inhibition of inosine 5'-monophosphate dehydrogenase by mycophenolic acid. Biochemistry. 1999 Nov 16;38(46):15388-97. doi: 10.1021/bi991558q. [PubMed:10563825 ]
Digits JA, Hedstrom L: Drug selectivity is determined by coupling across the NAD+ site of IMP dehydrogenase. Biochemistry. 2000 Feb 22;39(7):1771-7. doi: 10.1021/bi992288e. [PubMed:10677226 ]
Markland W, McQuaid TJ, Jain J, Kwong AD: Broad-spectrum antiviral activity of the IMP dehydrogenase inhibitor VX-497: a comparison with ribavirin and demonstration of antiviral additivity with alpha interferon. Antimicrob Agents Chemother. 2000 Apr;44(4):859-66. doi: 10.1128/AAC.44.4.859-866.2000. [PubMed:10722482 ]
McMillan FM, Cahoon M, White A, Hedstrom L, Petsko GA, Ringe D: Crystal structure at 2.4 A resolution of Borrelia burgdorferi inosine 5'-monophosphate dehydrogenase: evidence of a substrate-induced hinged-lid motion by loop 6. Biochemistry. 2000 Apr 18;39(15):4533-42. doi: 10.1021/bi992645l. [PubMed:10758003 ]
Albrecht W, Storck M, Pfetsch E, Martin W, Abendroth D: Development and application of a high-performance liquid chromatography-based assay for determination of the activity of inosine 5'-monophosphate dehydrogenase in whole blood and isolated mononuclear cells. Ther Drug Monit. 2000 Jun;22(3):283-94. doi: 10.1097/00007691-200006000-00009. [PubMed:10850395 ]
Sintchak MD, Nimmesgern E: The structure of inosine 5'-monophosphate dehydrogenase and the design of novel inhibitors. Immunopharmacology. 2000 May;47(2-3):163-84. doi: 10.1016/s0162-3109(00)00193-4. [PubMed:10878288 ]
Wall M, Shim JH, Benkovic SJ: Human AICAR transformylase: role of the 4-carboxamide of AICAR in binding and catalysis. Biochemistry. 2000 Sep 19;39(37):11303-11. doi: 10.1021/bi0007268. [PubMed:10985775 ]
Frueh FW, Hayashibara KC, Brown PO, Whitlock JP Jr: Use of cDNA microarrays to analyze dioxin-induced changes in human liver gene expression. Toxicol Lett. 2001 Jul 6;122(3):189-203. doi: 10.1016/s0378-4274(01)00364-2. [PubMed:11489354 ]
Glander P, Braun KP, Hambach P, Bauer S, Mai I, Roots I, Waiser J, Fritsche L, Neumayer HH, Budde K: Non-radioactive determination of inosine 5'-monophosphate dehydro-genase (IMPDH) in peripheral mononuclear cells. Clin Biochem. 2001 Oct;34(7):543-9. doi: 10.1016/s0009-9120(01)00267-3. [PubMed:11738390 ]
Rauniyar RK, Suzuma K, King AL, Aiello LP, King GL: Differential effects of bactericidal/permeability-increasing protein (BPI) analogues on retinal neovascularization and retinal pericyte growth. Invest Ophthalmol Vis Sci. 2002 Feb;43(2):503-9. [PubMed:11818397 ]
Daxecker H, Raab M, Muller MM: Influence of mycophenolic acid on inosine 5'-monophosphate dehydrogenase activity in human peripheral blood mononuclear cells. Clin Chim Acta. 2002 Apr;318(1-2):71-7. doi: 10.1016/s0009-8981(01)00801-4. [PubMed:11880114 ]
Stoychev G, Kierdaszuk B, Shugar D: Xanthosine and xanthine. Substrate properties with purine nucleoside phosphorylases, and relevance to other enzyme systems. Eur J Biochem. 2002 Aug;269(16):4048-57. doi: 10.1046/j.1432-1033.2002.03097.x. [PubMed:12180982 ]
Prosise GL, Luecke H: Crystal structures of Tritrichomonasfoetus inosine monophosphate dehydrogenase in complex with substrate, cofactor and analogs: a structural basis for the random-in ordered-out kinetic mechanism. J Mol Biol. 2003 Feb 14;326(2):517-27. doi: 10.1016/s0022-2836(02)01383-9. [PubMed:12559919 ]
Wolan DW, Cheong CG, Greasley SE, Wilson IA: Structural insights into the human and avian IMP cyclohydrolase mechanism via crystal structures with the bound XMP inhibitor. Biochemistry. 2004 Feb 10;43(5):1171-83. doi: 10.1021/bi030162i. [PubMed:14756553 ]
Barsotti C, Pesi R, Giannecchini M, Ipata PL: Evidence for the involvement of cytosolic 5'-nucleotidase (cN-II) in the synthesis of guanine nucleotides from xanthosine. J Biol Chem. 2005 Apr 8;280(14):13465-9. doi: 10.1074/jbc.M413347200. Epub 2005 Feb 6. [PubMed:15699053 ]
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 ]
Vethe NT, Bergan S: Determination of inosine monophosphate dehydrogenase activity in human CD4+ cells isolated from whole blood during mycophenolic acid therapy. Ther Drug Monit. 2006 Oct;28(5):608-13. doi: 10.1097/01.ftd.0000245680.38143.ca. [PubMed:17038874 ]

Showing metabocard for Xanthylic acid (MMDBc0029670)

MOL for #<Metabolite:0x00007f9ada7c81d0>

3D MOL for #<Metabolite:0x00007f9ada7c81d0>

3D SDF for #<Metabolite:0x00007f9ada7c81d0>

3D-SDF for #<Metabolite:0x00007f9ada7c81d0>

PDB for #<Metabolite:0x00007f9ada7c81d0>

3D PDB for #<Metabolite:0x00007f9ada7c81d0>

SMILES for #<Metabolite:0x00007f9ada7c81d0>

INCHI for #<Metabolite:0x00007f9ada7c81d0>

Structure for #<Metabolite:0x00007f9ada7c81d0>

3D Structure for #<Metabolite:0x00007f9ada7c81d0>