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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2021-09-14 15:38:58 UTC

HMDB ID

HMDB0001554

Secondary Accession Numbers

HMDB01554

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) Xanthylic acid can also be used in quantitative measurements of the Inosine monophosphate dehydrogenase enzyme activities in purine metabolism. This measurement is important for optimal thiopurine therapy for children with acute lymphoblastic leukaemia (ALL). (PMID: 16725387 ).

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>
HMDB0001554

> <DATABASE_NAME>
hmdb

> <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

View in JSmol View NMR Assignments View Stereo Labels

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

Chemical Formula

C₁₀H₁₃N₄O₉P

Average Molecular Weight

364.2054

Monoisotopic Molecular Weight

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 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Cytoplasm (HMDB: HMDB0001554)

Source

Endogenous

Endogenous (HMDB: HMDB0001554)

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

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

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

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

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

Equine

Horse (FooDB: FOOD00378)

Herbs and Spices (FooDB: FOOD00866)

Nut

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

Fruit

Pome

Drupe

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

Tropical fruit

Berry

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

Other fruit

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

Citrus

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

Fruits (FooDB: FOOD00871)

Vegetable

Shoot vegetable

Fruit vegetable

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

Root vegetable

Cabbage

Leaf vegetable

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

Mushroom

Tuber

Onion-family vegetable

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

Other vegetable

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

Stalk vegetable

Brassica

Brassicas (FooDB: FOOD00857)

Cereal and cereal product

Other bread

Other bread (FooDB: FOOD00269)

Cereal

Cereal product

Dough

Sourdough (FooDB: FOOD00275)

Cereals and cereal products (FooDB: FOOD00858)

Pulse

Bean

Lentil

Lentils (FooDB: FOOD00098)

Pea

Other pulse

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

Pulses (FooDB: FOOD00867)

Soy

Soy bean (FooDB: FOOD00085)

Soy product

Other soy product (FooDB: FOOD00271)

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

Gourd

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

Tea

Herbal tea

Greenthread tea (FooDB: FOOD00820)

Cocoa and cocoa product

Cocoa

Cocoa bean (FooDB: FOOD00182)

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Glutamate Metabolism (PathBank: SMP0087371)
Purine Nucleotides De Novo Biosynthesis 2 (PathBank: SMP0122223)
Purine Nucleotides De Novo Biosynthesis (PathBank: SMP0002377)
Purine Metabolism (PathBank: SMP0063668)
Purine Nucleotides De Novo Biosynthesis (PathBank: SMP0121307)
Purine Ribonucleosides Degradation (PathBank: SMP0002088)

Disease pathway

4-Hydroxybutyric Aciduria/Succinic Semialdehyde Dehydrogenase Deficiency (PathBank: SMP0120445)
Xanthinuria Type II (PathBank: SMP0120578)
Succinic Semialdehyde Dehydrogenase Deficiency (PathBank: SMP0120631)
Gout or Kelley-Seegmiller Syndrome (PathBank: SMP0120709)
Xanthine Dehydrogenase Deficiency (Xanthinuria) (PathBank: SMP0120717)
Mitochondrial DNA Depletion Syndrome (PathBank: SMP0120820)
Adenylosuccinate Lyase Deficiency (PathBank: SMP0120670)
AICA-Ribosiduria (PathBank: SMP0120673)
Purine Nucleoside Phosphorylase Deficiency (PathBank: SMP0120756)
Adenine Phosphoribosyltransferase Deficiency (APRT) (PathBank: SMP0120819)
Myoadenylate Deaminase Deficiency (PathBank: SMP0120821)
Adenosine Deaminase Deficiency (PathBank: SMP0120448)
Homocarnosinosis (PathBank: SMP0120494)
Lesch-Nyhan Syndrome (LNS) (PathBank: SMP0120508)
2-Hydroxyglutric Aciduria (D and L Form) (PathBank: SMP0120659)
Molybdenum Cofactor Deficiency (PathBank: SMP0120752)
Hyperinsulinism-Hyperammonemia Syndrome (PathBank: SMP0120496)
Xanthinuria Type I (PathBank: SMP0120577)
Mitochondrial DNA Depletion Syndrome (PathBank: SMP0000536)

Drug action pathway

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

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

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

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M-H]-	Not Available	164.738	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000130
[M+H]+	Not Available	175.3	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000130

Predicted Molecular 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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	183.661	31661259
DarkChem	[M+H]+	183.661	31661259
DarkChem	[M-H]-	177.28	31661259
DarkChem	[M-H]-	177.28	31661259
AllCCS	[M+H]+	177.199	32859911
AllCCS	[M-H]-	171.277	32859911
DeepCCS	[M+H]+	160.932	30932474
DeepCCS	[M-H]-	158.537	30932474
DeepCCS	[M-2H]-	192.209	30932474
DeepCCS	[M+Na]+	166.878	30932474
AllCCS	[M+H]+	177.2	32859911
AllCCS	[M+H-H2O]+	174.4	32859911
AllCCS	[M+NH4]+	179.8	32859911
AllCCS	[M+Na]+	180.5	32859911
AllCCS	[M-H]-	171.3	32859911
AllCCS	[M+Na-2H]-	170.9	32859911
AllCCS	[M+HCOO]-	170.5	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Xanthylic acid	O[C@@H]1[C@@H](COP(O)(O)=O)O[C@H]([C@@H]1O)N1C=NC2=C1NC(=O)NC2=O	4035.4	Standard polar	33892256
Xanthylic acid	O[C@@H]1[C@@H](COP(O)(O)=O)O[C@H]([C@@H]1O)N1C=NC2=C1NC(=O)NC2=O	1939.5	Standard non polar	33892256
Xanthylic acid	O[C@@H]1[C@@H](COP(O)(O)=O)O[C@H]([C@@H]1O)N1C=NC2=C1NC(=O)NC2=O	3735.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Xanthylic acid,1TMS,isomer #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	2833.0	Semi standard non polar	33892256
Xanthylic acid,1TMS,isomer #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	2804.8	Semi standard non polar	33892256
Xanthylic acid,1TMS,isomer #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	2999.0	Semi standard non polar	33892256
Xanthylic acid,1TMS,isomer #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	2955.4	Semi standard non polar	33892256
Xanthylic acid,1TMS,isomer #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	2937.6	Semi standard non polar	33892256
Xanthylic acid,2TMS,isomer #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[Si](C)(C)C	2712.7	Semi standard non polar	33892256
Xanthylic acid,2TMS,isomer #10	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	3054.6	Semi standard non polar	33892256
Xanthylic acid,2TMS,isomer #11	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	3031.7	Semi standard non polar	33892256
Xanthylic acid,2TMS,isomer #2	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	2916.3	Semi standard non polar	33892256
Xanthylic acid,2TMS,isomer #3	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	2874.8	Semi standard non polar	33892256
Xanthylic acid,2TMS,isomer #4	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	2887.6	Semi standard non polar	33892256
Xanthylic acid,2TMS,isomer #5	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	2890.8	Semi standard non polar	33892256
Xanthylic acid,2TMS,isomer #6	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	2851.0	Semi standard non polar	33892256
Xanthylic acid,2TMS,isomer #7	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	2861.8	Semi standard non polar	33892256
Xanthylic acid,2TMS,isomer #8	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	2975.4	Semi standard non polar	33892256
Xanthylic acid,2TMS,isomer #9	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	3046.3	Semi standard non polar	33892256
Xanthylic acid,3TMS,isomer #1	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	2844.8	Semi standard non polar	33892256
Xanthylic acid,3TMS,isomer #1	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	3311.7	Standard non polar	33892256
Xanthylic acid,3TMS,isomer #1	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	4430.7	Standard polar	33892256
Xanthylic acid,3TMS,isomer #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=C1N([Si](C)(C)C)C(=O)[NH]C2=O	2967.8	Semi standard non polar	33892256
Xanthylic acid,3TMS,isomer #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=C1N([Si](C)(C)C)C(=O)[NH]C2=O	3333.2	Standard non polar	33892256
Xanthylic acid,3TMS,isomer #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=C1N([Si](C)(C)C)C(=O)[NH]C2=O	4458.2	Standard polar	33892256
Xanthylic acid,3TMS,isomer #11	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	2923.2	Semi standard non polar	33892256
Xanthylic acid,3TMS,isomer #11	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	3359.9	Standard non polar	33892256
Xanthylic acid,3TMS,isomer #11	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	4881.6	Standard polar	33892256
Xanthylic acid,3TMS,isomer #12	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	3040.8	Semi standard non polar	33892256
Xanthylic acid,3TMS,isomer #12	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	3255.4	Standard non polar	33892256
Xanthylic acid,3TMS,isomer #12	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	4258.6	Standard polar	33892256
Xanthylic acid,3TMS,isomer #13	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	3034.9	Semi standard non polar	33892256
Xanthylic acid,3TMS,isomer #13	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	3336.7	Standard non polar	33892256
Xanthylic acid,3TMS,isomer #13	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	4242.3	Standard polar	33892256
Xanthylic acid,3TMS,isomer #14	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	3104.3	Semi standard non polar	33892256
Xanthylic acid,3TMS,isomer #14	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	3306.1	Standard non polar	33892256
Xanthylic acid,3TMS,isomer #14	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	4579.9	Standard polar	33892256
Xanthylic acid,3TMS,isomer #2	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	2833.4	Semi standard non polar	33892256
Xanthylic acid,3TMS,isomer #2	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	3325.5	Standard non polar	33892256
Xanthylic acid,3TMS,isomer #2	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	4795.7	Standard polar	33892256
Xanthylic acid,3TMS,isomer #3	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	2817.5	Semi standard non polar	33892256
Xanthylic acid,3TMS,isomer #3	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	3387.5	Standard non polar	33892256
Xanthylic acid,3TMS,isomer #3	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	4774.0	Standard polar	33892256
Xanthylic acid,3TMS,isomer #4	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	2923.9	Semi standard non polar	33892256
Xanthylic acid,3TMS,isomer #4	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	3294.3	Standard non polar	33892256
Xanthylic acid,3TMS,isomer #4	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	4144.0	Standard polar	33892256
Xanthylic acid,3TMS,isomer #5	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	2979.7	Semi standard non polar	33892256
Xanthylic acid,3TMS,isomer #5	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	3251.7	Standard non polar	33892256
Xanthylic acid,3TMS,isomer #5	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	4453.4	Standard polar	33892256
Xanthylic acid,3TMS,isomer #6	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	2982.4	Semi standard non polar	33892256
Xanthylic acid,3TMS,isomer #6	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	3327.6	Standard non polar	33892256
Xanthylic acid,3TMS,isomer #6	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	4435.7	Standard polar	33892256
Xanthylic acid,3TMS,isomer #7	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	2947.4	Semi standard non polar	33892256
Xanthylic acid,3TMS,isomer #7	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	3346.6	Standard non polar	33892256
Xanthylic acid,3TMS,isomer #7	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	4864.5	Standard polar	33892256
Xanthylic acid,3TMS,isomer #8	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	2905.3	Semi standard non polar	33892256
Xanthylic acid,3TMS,isomer #8	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	3309.2	Standard non polar	33892256
Xanthylic acid,3TMS,isomer #8	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	4185.3	Standard polar	33892256
Xanthylic acid,3TMS,isomer #9	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	2968.4	Semi standard non polar	33892256
Xanthylic acid,3TMS,isomer #9	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	3266.5	Standard non polar	33892256
Xanthylic acid,3TMS,isomer #9	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	4483.0	Standard polar	33892256
Xanthylic acid,4TMS,isomer #1	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	2912.3	Semi standard non polar	33892256
Xanthylic acid,4TMS,isomer #1	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	3253.9	Standard non polar	33892256
Xanthylic acid,4TMS,isomer #1	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	3911.6	Standard polar	33892256
Xanthylic acid,4TMS,isomer #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=C1N([Si](C)(C)C)C(=O)N([Si](C)(C)C)C2=O	3047.6	Semi standard non polar	33892256
Xanthylic acid,4TMS,isomer #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=C1N([Si](C)(C)C)C(=O)N([Si](C)(C)C)C2=O	3255.8	Standard non polar	33892256
Xanthylic acid,4TMS,isomer #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=C1N([Si](C)(C)C)C(=O)N([Si](C)(C)C)C2=O	4200.6	Standard polar	33892256
Xanthylic acid,4TMS,isomer #11	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	3110.1	Semi standard non polar	33892256
Xanthylic acid,4TMS,isomer #11	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	3238.3	Standard non polar	33892256
Xanthylic acid,4TMS,isomer #11	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	4024.1	Standard polar	33892256
Xanthylic acid,4TMS,isomer #2	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	2967.8	Semi standard non polar	33892256
Xanthylic acid,4TMS,isomer #2	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	3218.7	Standard non polar	33892256
Xanthylic acid,4TMS,isomer #2	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	4138.7	Standard polar	33892256
Xanthylic acid,4TMS,isomer #3	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	2958.1	Semi standard non polar	33892256
Xanthylic acid,4TMS,isomer #3	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	3276.2	Standard non polar	33892256
Xanthylic acid,4TMS,isomer #3	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	4106.3	Standard polar	33892256
Xanthylic acid,4TMS,isomer #4	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	2926.8	Semi standard non polar	33892256
Xanthylic acid,4TMS,isomer #4	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	3304.7	Standard non polar	33892256
Xanthylic acid,4TMS,isomer #4	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	4444.0	Standard polar	33892256
Xanthylic acid,4TMS,isomer #5	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	3035.6	Semi standard non polar	33892256
Xanthylic acid,4TMS,isomer #5	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	3182.9	Standard non polar	33892256
Xanthylic acid,4TMS,isomer #5	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	3896.7	Standard polar	33892256
Xanthylic acid,4TMS,isomer #6	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	3026.9	Semi standard non polar	33892256
Xanthylic acid,4TMS,isomer #6	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	3254.1	Standard non polar	33892256
Xanthylic acid,4TMS,isomer #6	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	3871.7	Standard polar	33892256
Xanthylic acid,4TMS,isomer #7	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	3058.9	Semi standard non polar	33892256
Xanthylic acid,4TMS,isomer #7	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	3242.0	Standard non polar	33892256
Xanthylic acid,4TMS,isomer #7	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	4177.8	Standard polar	33892256
Xanthylic acid,4TMS,isomer #8	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	3020.1	Semi standard non polar	33892256
Xanthylic acid,4TMS,isomer #8	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	3206.2	Standard non polar	33892256
Xanthylic acid,4TMS,isomer #8	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	3938.4	Standard polar	33892256
Xanthylic acid,4TMS,isomer #9	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	3013.3	Semi standard non polar	33892256
Xanthylic acid,4TMS,isomer #9	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	3267.4	Standard non polar	33892256
Xanthylic acid,4TMS,isomer #9	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	3908.0	Standard polar	33892256
Xanthylic acid,5TMS,isomer #1	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	3036.2	Semi standard non polar	33892256
Xanthylic acid,5TMS,isomer #1	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	3146.1	Standard non polar	33892256
Xanthylic acid,5TMS,isomer #1	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	3712.6	Standard polar	33892256
Xanthylic acid,5TMS,isomer #2	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	3028.2	Semi standard non polar	33892256
Xanthylic acid,5TMS,isomer #2	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	3200.5	Standard non polar	33892256
Xanthylic acid,5TMS,isomer #2	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	3679.3	Standard polar	33892256
Xanthylic acid,5TMS,isomer #3	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	3076.4	Semi standard non polar	33892256
Xanthylic acid,5TMS,isomer #3	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	3202.0	Standard non polar	33892256
Xanthylic acid,5TMS,isomer #3	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	3890.7	Standard polar	33892256
Xanthylic acid,5TMS,isomer #4	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	3135.1	Semi standard non polar	33892256
Xanthylic acid,5TMS,isomer #4	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	3164.8	Standard non polar	33892256
Xanthylic acid,5TMS,isomer #4	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	3706.8	Standard polar	33892256
Xanthylic acid,5TMS,isomer #5	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	3124.0	Semi standard non polar	33892256
Xanthylic acid,5TMS,isomer #5	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	3177.4	Standard non polar	33892256
Xanthylic acid,5TMS,isomer #5	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	3741.3	Standard polar	33892256
Xanthylic acid,6TMS,isomer #1	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	3169.4	Semi standard non polar	33892256
Xanthylic acid,6TMS,isomer #1	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	3128.0	Standard non polar	33892256
Xanthylic acid,6TMS,isomer #1	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	3548.9	Standard polar	33892256
Xanthylic acid,1TBDMS,isomer #1	CC(C)(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	3062.9	Semi standard non polar	33892256
Xanthylic acid,1TBDMS,isomer #2	CC(C)(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	3032.9	Semi standard non polar	33892256
Xanthylic acid,1TBDMS,isomer #3	CC(C)(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	3227.1	Semi standard non polar	33892256
Xanthylic acid,1TBDMS,isomer #4	CC(C)(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	3168.8	Semi standard non polar	33892256
Xanthylic acid,1TBDMS,isomer #5	CC(C)(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	3169.9	Semi standard non polar	33892256
Xanthylic acid,2TBDMS,isomer #1	CC(C)(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(C)(C)C	3151.6	Semi standard non polar	33892256
Xanthylic acid,2TBDMS,isomer #10	CC(C)(C)[Si](C)(C)OP(=O)(O)OC[C@H]1O[C@@H](N2C=NC3=C2N([Si](C)(C)C(C)(C)C)C(=O)[NH]C3=O)[C@H](O)[C@@H]1O	3431.0	Semi standard non polar	33892256
Xanthylic acid,2TBDMS,isomer #11	CC(C)(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(C)(C)C)C1=O	3400.7	Semi standard non polar	33892256
Xanthylic acid,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H](COP(=O)(O)O[Si](C)(C)C(C)(C)C)O[C@@H](N2C=NC3=C2[NH]C(=O)[NH]C3=O)[C@@H]1O	3313.5	Semi standard non polar	33892256
Xanthylic acid,2TBDMS,isomer #3	CC(C)(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(C)(C)C)C3=O)[C@@H]1O	3317.8	Semi standard non polar	33892256
Xanthylic acid,2TBDMS,isomer #4	CC(C)(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)(C)C)C(=O)[NH]C3=O)[C@@H]1O	3299.0	Semi standard non polar	33892256
Xanthylic acid,2TBDMS,isomer #5	CC(C)(C)[Si](C)(C)O[C@@H]1[C@H](O)[C@@H](COP(=O)(O)O[Si](C)(C)C(C)(C)C)O[C@H]1N1C=NC2=C1[NH]C(=O)[NH]C2=O	3294.6	Semi standard non polar	33892256
Xanthylic acid,2TBDMS,isomer #6	CC(C)(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(C)(C)C)C2=O	3302.1	Semi standard non polar	33892256
Xanthylic acid,2TBDMS,isomer #7	CC(C)(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)(C)C)C(=O)[NH]C2=O	3278.3	Semi standard non polar	33892256
Xanthylic acid,2TBDMS,isomer #8	CC(C)(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(C)(C)C	3359.2	Semi standard non polar	33892256
Xanthylic acid,2TBDMS,isomer #9	CC(C)(C)[Si](C)(C)OP(=O)(O)OC[C@H]1O[C@@H](N2C=NC3=C2[NH]C(=O)N([Si](C)(C)C(C)(C)C)C3=O)[C@H](O)[C@@H]1O	3435.7	Semi standard non polar	33892256
Xanthylic acid,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H](COP(=O)(O)O[Si](C)(C)C(C)(C)C)O[C@@H](N2C=NC3=C2[NH]C(=O)[NH]C3=O)[C@@H]1O[Si](C)(C)C(C)(C)C	3456.1	Semi standard non polar	33892256
Xanthylic acid,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H](COP(=O)(O)O[Si](C)(C)C(C)(C)C)O[C@@H](N2C=NC3=C2[NH]C(=O)[NH]C3=O)[C@@H]1O[Si](C)(C)C(C)(C)C	3867.9	Standard non polar	33892256
Xanthylic acid,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H](COP(=O)(O)O[Si](C)(C)C(C)(C)C)O[C@@H](N2C=NC3=C2[NH]C(=O)[NH]C3=O)[C@@H]1O[Si](C)(C)C(C)(C)C	4521.3	Standard polar	33892256
Xanthylic acid,3TBDMS,isomer #10	CC(C)(C)[Si](C)(C)O[C@@H]1[C@H](O)[C@@H](COP(=O)(O)O[Si](C)(C)C(C)(C)C)O[C@H]1N1C=NC2=C1N([Si](C)(C)C(C)(C)C)C(=O)[NH]C2=O	3548.5	Semi standard non polar	33892256
Xanthylic acid,3TBDMS,isomer #10	CC(C)(C)[Si](C)(C)O[C@@H]1[C@H](O)[C@@H](COP(=O)(O)O[Si](C)(C)C(C)(C)C)O[C@H]1N1C=NC2=C1N([Si](C)(C)C(C)(C)C)C(=O)[NH]C2=O	3892.8	Standard non polar	33892256
Xanthylic acid,3TBDMS,isomer #10	CC(C)(C)[Si](C)(C)O[C@@H]1[C@H](O)[C@@H](COP(=O)(O)O[Si](C)(C)C(C)(C)C)O[C@H]1N1C=NC2=C1N([Si](C)(C)C(C)(C)C)C(=O)[NH]C2=O	4490.1	Standard polar	33892256
Xanthylic acid,3TBDMS,isomer #11	CC(C)(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)(C)C)C(=O)N([Si](C)(C)C(C)(C)C)C2=O	3545.6	Semi standard non polar	33892256
Xanthylic acid,3TBDMS,isomer #11	CC(C)(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)(C)C)C(=O)N([Si](C)(C)C(C)(C)C)C2=O	3923.4	Standard non polar	33892256
Xanthylic acid,3TBDMS,isomer #11	CC(C)(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)(C)C)C(=O)N([Si](C)(C)C(C)(C)C)C2=O	4752.5	Standard polar	33892256
Xanthylic acid,3TBDMS,isomer #12	CC(C)(C)[Si](C)(C)OP(=O)(OC[C@H]1O[C@@H](N2C=NC3=C2[NH]C(=O)N([Si](C)(C)C(C)(C)C)C3=O)[C@H](O)[C@@H]1O)O[Si](C)(C)C(C)(C)C	3616.4	Semi standard non polar	33892256
Xanthylic acid,3TBDMS,isomer #12	CC(C)(C)[Si](C)(C)OP(=O)(OC[C@H]1O[C@@H](N2C=NC3=C2[NH]C(=O)N([Si](C)(C)C(C)(C)C)C3=O)[C@H](O)[C@@H]1O)O[Si](C)(C)C(C)(C)C	3745.8	Standard non polar	33892256
Xanthylic acid,3TBDMS,isomer #12	CC(C)(C)[Si](C)(C)OP(=O)(OC[C@H]1O[C@@H](N2C=NC3=C2[NH]C(=O)N([Si](C)(C)C(C)(C)C)C3=O)[C@H](O)[C@@H]1O)O[Si](C)(C)C(C)(C)C	4372.6	Standard polar	33892256
Xanthylic acid,3TBDMS,isomer #13	CC(C)(C)[Si](C)(C)OP(=O)(OC[C@H]1O[C@@H](N2C=NC3=C2N([Si](C)(C)C(C)(C)C)C(=O)[NH]C3=O)[C@H](O)[C@@H]1O)O[Si](C)(C)C(C)(C)C	3603.1	Semi standard non polar	33892256
Xanthylic acid,3TBDMS,isomer #13	CC(C)(C)[Si](C)(C)OP(=O)(OC[C@H]1O[C@@H](N2C=NC3=C2N([Si](C)(C)C(C)(C)C)C(=O)[NH]C3=O)[C@H](O)[C@@H]1O)O[Si](C)(C)C(C)(C)C	3825.1	Standard non polar	33892256
Xanthylic acid,3TBDMS,isomer #13	CC(C)(C)[Si](C)(C)OP(=O)(OC[C@H]1O[C@@H](N2C=NC3=C2N([Si](C)(C)C(C)(C)C)C(=O)[NH]C3=O)[C@H](O)[C@@H]1O)O[Si](C)(C)C(C)(C)C	4348.5	Standard polar	33892256
Xanthylic acid,3TBDMS,isomer #14	CC(C)(C)[Si](C)(C)OP(=O)(O)OC[C@H]1O[C@@H](N2C=NC3=C2N([Si](C)(C)C(C)(C)C)C(=O)N([Si](C)(C)C(C)(C)C)C3=O)[C@H](O)[C@@H]1O	3651.7	Semi standard non polar	33892256
Xanthylic acid,3TBDMS,isomer #14	CC(C)(C)[Si](C)(C)OP(=O)(O)OC[C@H]1O[C@@H](N2C=NC3=C2N([Si](C)(C)C(C)(C)C)C(=O)N([Si](C)(C)C(C)(C)C)C3=O)[C@H](O)[C@@H]1O	3820.2	Standard non polar	33892256
Xanthylic acid,3TBDMS,isomer #14	CC(C)(C)[Si](C)(C)OP(=O)(O)OC[C@H]1O[C@@H](N2C=NC3=C2N([Si](C)(C)C(C)(C)C)C(=O)N([Si](C)(C)C(C)(C)C)C3=O)[C@H](O)[C@@H]1O	4564.4	Standard polar	33892256
Xanthylic acid,3TBDMS,isomer #2	CC(C)(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(C)(C)C)C3=O)[C@@H]1O[Si](C)(C)C(C)(C)C	3487.8	Semi standard non polar	33892256
Xanthylic acid,3TBDMS,isomer #2	CC(C)(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(C)(C)C)C3=O)[C@@H]1O[Si](C)(C)C(C)(C)C	3913.8	Standard non polar	33892256
Xanthylic acid,3TBDMS,isomer #2	CC(C)(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(C)(C)C)C3=O)[C@@H]1O[Si](C)(C)C(C)(C)C	4727.6	Standard polar	33892256
Xanthylic acid,3TBDMS,isomer #3	CC(C)(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)(C)C)C(=O)[NH]C3=O)[C@@H]1O[Si](C)(C)C(C)(C)C	3444.8	Semi standard non polar	33892256
Xanthylic acid,3TBDMS,isomer #3	CC(C)(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)(C)C)C(=O)[NH]C3=O)[C@@H]1O[Si](C)(C)C(C)(C)C	3970.4	Standard non polar	33892256
Xanthylic acid,3TBDMS,isomer #3	CC(C)(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)(C)C)C(=O)[NH]C3=O)[C@@H]1O[Si](C)(C)C(C)(C)C	4700.3	Standard polar	33892256
Xanthylic acid,3TBDMS,isomer #4	CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H](COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)O[C@@H](N2C=NC3=C2[NH]C(=O)[NH]C3=O)[C@@H]1O	3495.8	Semi standard non polar	33892256
Xanthylic acid,3TBDMS,isomer #4	CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H](COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)O[C@@H](N2C=NC3=C2[NH]C(=O)[NH]C3=O)[C@@H]1O	3787.8	Standard non polar	33892256
Xanthylic acid,3TBDMS,isomer #4	CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H](COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)O[C@@H](N2C=NC3=C2[NH]C(=O)[NH]C3=O)[C@@H]1O	4316.7	Standard polar	33892256
Xanthylic acid,3TBDMS,isomer #5	CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H](COP(=O)(O)O[Si](C)(C)C(C)(C)C)O[C@@H](N2C=NC3=C2[NH]C(=O)N([Si](C)(C)C(C)(C)C)C3=O)[C@@H]1O	3587.9	Semi standard non polar	33892256
Xanthylic acid,3TBDMS,isomer #5	CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H](COP(=O)(O)O[Si](C)(C)C(C)(C)C)O[C@@H](N2C=NC3=C2[NH]C(=O)N([Si](C)(C)C(C)(C)C)C3=O)[C@@H]1O	3805.7	Standard non polar	33892256
Xanthylic acid,3TBDMS,isomer #5	CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H](COP(=O)(O)O[Si](C)(C)C(C)(C)C)O[C@@H](N2C=NC3=C2[NH]C(=O)N([Si](C)(C)C(C)(C)C)C3=O)[C@@H]1O	4494.6	Standard polar	33892256
Xanthylic acid,3TBDMS,isomer #6	CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H](COP(=O)(O)O[Si](C)(C)C(C)(C)C)O[C@@H](N2C=NC3=C2N([Si](C)(C)C(C)(C)C)C(=O)[NH]C3=O)[C@@H]1O	3561.8	Semi standard non polar	33892256
Xanthylic acid,3TBDMS,isomer #6	CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H](COP(=O)(O)O[Si](C)(C)C(C)(C)C)O[C@@H](N2C=NC3=C2N([Si](C)(C)C(C)(C)C)C(=O)[NH]C3=O)[C@@H]1O	3882.4	Standard non polar	33892256
Xanthylic acid,3TBDMS,isomer #6	CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H](COP(=O)(O)O[Si](C)(C)C(C)(C)C)O[C@@H](N2C=NC3=C2N([Si](C)(C)C(C)(C)C)C(=O)[NH]C3=O)[C@@H]1O	4469.9	Standard polar	33892256
Xanthylic acid,3TBDMS,isomer #7	CC(C)(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)(C)C)C(=O)N([Si](C)(C)C(C)(C)C)C3=O)[C@@H]1O	3558.6	Semi standard non polar	33892256
Xanthylic acid,3TBDMS,isomer #7	CC(C)(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)(C)C)C(=O)N([Si](C)(C)C(C)(C)C)C3=O)[C@@H]1O	3910.6	Standard non polar	33892256
Xanthylic acid,3TBDMS,isomer #7	CC(C)(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)(C)C)C(=O)N([Si](C)(C)C(C)(C)C)C3=O)[C@@H]1O	4736.9	Standard polar	33892256
Xanthylic acid,3TBDMS,isomer #8	CC(C)(C)[Si](C)(C)O[C@@H]1[C@H](O)[C@@H](COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)O[C@H]1N1C=NC2=C1[NH]C(=O)[NH]C2=O	3486.2	Semi standard non polar	33892256
Xanthylic acid,3TBDMS,isomer #8	CC(C)(C)[Si](C)(C)O[C@@H]1[C@H](O)[C@@H](COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)O[C@H]1N1C=NC2=C1[NH]C(=O)[NH]C2=O	3816.1	Standard non polar	33892256
Xanthylic acid,3TBDMS,isomer #8	CC(C)(C)[Si](C)(C)O[C@@H]1[C@H](O)[C@@H](COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)O[C@H]1N1C=NC2=C1[NH]C(=O)[NH]C2=O	4356.0	Standard polar	33892256
Xanthylic acid,3TBDMS,isomer #9	CC(C)(C)[Si](C)(C)O[C@@H]1[C@H](O)[C@@H](COP(=O)(O)O[Si](C)(C)C(C)(C)C)O[C@H]1N1C=NC2=C1[NH]C(=O)N([Si](C)(C)C(C)(C)C)C2=O	3578.3	Semi standard non polar	33892256
Xanthylic acid,3TBDMS,isomer #9	CC(C)(C)[Si](C)(C)O[C@@H]1[C@H](O)[C@@H](COP(=O)(O)O[Si](C)(C)C(C)(C)C)O[C@H]1N1C=NC2=C1[NH]C(=O)N([Si](C)(C)C(C)(C)C)C2=O	3829.5	Standard non polar	33892256
Xanthylic acid,3TBDMS,isomer #9	CC(C)(C)[Si](C)(C)O[C@@H]1[C@H](O)[C@@H](COP(=O)(O)O[Si](C)(C)C(C)(C)C)O[C@H]1N1C=NC2=C1[NH]C(=O)N([Si](C)(C)C(C)(C)C)C2=O	4518.2	Standard polar	33892256
Xanthylic acid,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H](COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)O[C@@H](N2C=NC3=C2[NH]C(=O)[NH]C3=O)[C@@H]1O[Si](C)(C)C(C)(C)C	3677.6	Semi standard non polar	33892256
Xanthylic acid,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H](COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)O[C@@H](N2C=NC3=C2[NH]C(=O)[NH]C3=O)[C@@H]1O[Si](C)(C)C(C)(C)C	3917.6	Standard non polar	33892256
Xanthylic acid,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H](COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)O[C@@H](N2C=NC3=C2[NH]C(=O)[NH]C3=O)[C@@H]1O[Si](C)(C)C(C)(C)C	4160.2	Standard polar	33892256
Xanthylic acid,4TBDMS,isomer #10	CC(C)(C)[Si](C)(C)O[C@@H]1[C@H](O)[C@@H](COP(=O)(O)O[Si](C)(C)C(C)(C)C)O[C@H]1N1C=NC2=C1N([Si](C)(C)C(C)(C)C)C(=O)N([Si](C)(C)C(C)(C)C)C2=O	3826.4	Semi standard non polar	33892256
Xanthylic acid,4TBDMS,isomer #10	CC(C)(C)[Si](C)(C)O[C@@H]1[C@H](O)[C@@H](COP(=O)(O)O[Si](C)(C)C(C)(C)C)O[C@H]1N1C=NC2=C1N([Si](C)(C)C(C)(C)C)C(=O)N([Si](C)(C)C(C)(C)C)C2=O	3944.6	Standard non polar	33892256
Xanthylic acid,4TBDMS,isomer #10	CC(C)(C)[Si](C)(C)O[C@@H]1[C@H](O)[C@@H](COP(=O)(O)O[Si](C)(C)C(C)(C)C)O[C@H]1N1C=NC2=C1N([Si](C)(C)C(C)(C)C)C(=O)N([Si](C)(C)C(C)(C)C)C2=O	4263.0	Standard polar	33892256
Xanthylic acid,4TBDMS,isomer #11	CC(C)(C)[Si](C)(C)OP(=O)(OC[C@H]1O[C@@H](N2C=NC3=C2N([Si](C)(C)C(C)(C)C)C(=O)N([Si](C)(C)C(C)(C)C)C3=O)[C@H](O)[C@@H]1O)O[Si](C)(C)C(C)(C)C	3841.9	Semi standard non polar	33892256
Xanthylic acid,4TBDMS,isomer #11	CC(C)(C)[Si](C)(C)OP(=O)(OC[C@H]1O[C@@H](N2C=NC3=C2N([Si](C)(C)C(C)(C)C)C(=O)N([Si](C)(C)C(C)(C)C)C3=O)[C@H](O)[C@@H]1O)O[Si](C)(C)C(C)(C)C	3873.6	Standard non polar	33892256
Xanthylic acid,4TBDMS,isomer #11	CC(C)(C)[Si](C)(C)OP(=O)(OC[C@H]1O[C@@H](N2C=NC3=C2N([Si](C)(C)C(C)(C)C)C(=O)N([Si](C)(C)C(C)(C)C)C3=O)[C@H](O)[C@@H]1O)O[Si](C)(C)C(C)(C)C	4174.7	Standard polar	33892256
Xanthylic acid,4TBDMS,isomer #2	CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H](COP(=O)(O)O[Si](C)(C)C(C)(C)C)O[C@@H](N2C=NC3=C2[NH]C(=O)N([Si](C)(C)C(C)(C)C)C3=O)[C@@H]1O[Si](C)(C)C(C)(C)C	3780.8	Semi standard non polar	33892256
Xanthylic acid,4TBDMS,isomer #2	CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H](COP(=O)(O)O[Si](C)(C)C(C)(C)C)O[C@@H](N2C=NC3=C2[NH]C(=O)N([Si](C)(C)C(C)(C)C)C3=O)[C@@H]1O[Si](C)(C)C(C)(C)C	3941.9	Standard non polar	33892256
Xanthylic acid,4TBDMS,isomer #2	CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H](COP(=O)(O)O[Si](C)(C)C(C)(C)C)O[C@@H](N2C=NC3=C2[NH]C(=O)N([Si](C)(C)C(C)(C)C)C3=O)[C@@H]1O[Si](C)(C)C(C)(C)C	4261.8	Standard polar	33892256
Xanthylic acid,4TBDMS,isomer #3	CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H](COP(=O)(O)O[Si](C)(C)C(C)(C)C)O[C@@H](N2C=NC3=C2N([Si](C)(C)C(C)(C)C)C(=O)[NH]C3=O)[C@@H]1O[Si](C)(C)C(C)(C)C	3749.5	Semi standard non polar	33892256
Xanthylic acid,4TBDMS,isomer #3	CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H](COP(=O)(O)O[Si](C)(C)C(C)(C)C)O[C@@H](N2C=NC3=C2N([Si](C)(C)C(C)(C)C)C(=O)[NH]C3=O)[C@@H]1O[Si](C)(C)C(C)(C)C	3993.2	Standard non polar	33892256
Xanthylic acid,4TBDMS,isomer #3	CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H](COP(=O)(O)O[Si](C)(C)C(C)(C)C)O[C@@H](N2C=NC3=C2N([Si](C)(C)C(C)(C)C)C(=O)[NH]C3=O)[C@@H]1O[Si](C)(C)C(C)(C)C	4229.4	Standard polar	33892256
Xanthylic acid,4TBDMS,isomer #4	CC(C)(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)(C)C)C(=O)N([Si](C)(C)C(C)(C)C)C3=O)[C@@H]1O[Si](C)(C)C(C)(C)C	3748.2	Semi standard non polar	33892256
Xanthylic acid,4TBDMS,isomer #4	CC(C)(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)(C)C)C(=O)N([Si](C)(C)C(C)(C)C)C3=O)[C@@H]1O[Si](C)(C)C(C)(C)C	4002.3	Standard non polar	33892256
Xanthylic acid,4TBDMS,isomer #4	CC(C)(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)(C)C)C(=O)N([Si](C)(C)C(C)(C)C)C3=O)[C@@H]1O[Si](C)(C)C(C)(C)C	4410.4	Standard polar	33892256
Xanthylic acid,4TBDMS,isomer #5	CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H](COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)O[C@@H](N2C=NC3=C2[NH]C(=O)N([Si](C)(C)C(C)(C)C)C3=O)[C@@H]1O	3799.1	Semi standard non polar	33892256
Xanthylic acid,4TBDMS,isomer #5	CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H](COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)O[C@@H](N2C=NC3=C2[NH]C(=O)N([Si](C)(C)C(C)(C)C)C3=O)[C@@H]1O	3852.2	Standard non polar	33892256
Xanthylic acid,4TBDMS,isomer #5	CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H](COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)O[C@@H](N2C=NC3=C2[NH]C(=O)N([Si](C)(C)C(C)(C)C)C3=O)[C@@H]1O	4117.5	Standard polar	33892256
Xanthylic acid,4TBDMS,isomer #6	CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H](COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)O[C@@H](N2C=NC3=C2N([Si](C)(C)C(C)(C)C)C(=O)[NH]C3=O)[C@@H]1O	3772.7	Semi standard non polar	33892256
Xanthylic acid,4TBDMS,isomer #6	CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H](COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)O[C@@H](N2C=NC3=C2N([Si](C)(C)C(C)(C)C)C(=O)[NH]C3=O)[C@@H]1O	3926.7	Standard non polar	33892256
Xanthylic acid,4TBDMS,isomer #6	CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H](COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)O[C@@H](N2C=NC3=C2N([Si](C)(C)C(C)(C)C)C(=O)[NH]C3=O)[C@@H]1O	4088.9	Standard polar	33892256
Xanthylic acid,4TBDMS,isomer #7	CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H](COP(=O)(O)O[Si](C)(C)C(C)(C)C)O[C@@H](N2C=NC3=C2N([Si](C)(C)C(C)(C)C)C(=O)N([Si](C)(C)C(C)(C)C)C3=O)[C@@H]1O	3831.2	Semi standard non polar	33892256
Xanthylic acid,4TBDMS,isomer #7	CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H](COP(=O)(O)O[Si](C)(C)C(C)(C)C)O[C@@H](N2C=NC3=C2N([Si](C)(C)C(C)(C)C)C(=O)N([Si](C)(C)C(C)(C)C)C3=O)[C@@H]1O	3930.4	Standard non polar	33892256
Xanthylic acid,4TBDMS,isomer #7	CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H](COP(=O)(O)O[Si](C)(C)C(C)(C)C)O[C@@H](N2C=NC3=C2N([Si](C)(C)C(C)(C)C)C(=O)N([Si](C)(C)C(C)(C)C)C3=O)[C@@H]1O	4245.2	Standard polar	33892256
Xanthylic acid,4TBDMS,isomer #8	CC(C)(C)[Si](C)(C)O[C@@H]1[C@H](O)[C@@H](COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)O[C@H]1N1C=NC2=C1[NH]C(=O)N([Si](C)(C)C(C)(C)C)C2=O	3789.3	Semi standard non polar	33892256
Xanthylic acid,4TBDMS,isomer #8	CC(C)(C)[Si](C)(C)O[C@@H]1[C@H](O)[C@@H](COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)O[C@H]1N1C=NC2=C1[NH]C(=O)N([Si](C)(C)C(C)(C)C)C2=O	3888.0	Standard non polar	33892256
Xanthylic acid,4TBDMS,isomer #8	CC(C)(C)[Si](C)(C)O[C@@H]1[C@H](O)[C@@H](COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)O[C@H]1N1C=NC2=C1[NH]C(=O)N([Si](C)(C)C(C)(C)C)C2=O	4153.5	Standard polar	33892256
Xanthylic acid,4TBDMS,isomer #9	CC(C)(C)[Si](C)(C)O[C@@H]1[C@H](O)[C@@H](COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)O[C@H]1N1C=NC2=C1N([Si](C)(C)C(C)(C)C)C(=O)[NH]C2=O	3761.6	Semi standard non polar	33892256
Xanthylic acid,4TBDMS,isomer #9	CC(C)(C)[Si](C)(C)O[C@@H]1[C@H](O)[C@@H](COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)O[C@H]1N1C=NC2=C1N([Si](C)(C)C(C)(C)C)C(=O)[NH]C2=O	3943.7	Standard non polar	33892256
Xanthylic acid,4TBDMS,isomer #9	CC(C)(C)[Si](C)(C)O[C@@H]1[C@H](O)[C@@H](COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)O[C@H]1N1C=NC2=C1N([Si](C)(C)C(C)(C)C)C(=O)[NH]C2=O	4122.0	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Xanthylic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-0002-9613000000-3054f73e4c9456039ed6	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Xanthylic acid GC-MS (2 TMS) - 70eV, Positive	splash10-01ot-9521200000-1e6fc3c628d8ebd23b37	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Xanthylic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Xanthylic acid LC-ESI-QTOF , negative-QTOF	splash10-0ik9-7964000000-bce7ee60221f82790f35	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Xanthylic acid LC-ESI-QTOF , positive-QTOF	splash10-0002-9400000000-05c1ae772c001a15a8c6	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Xanthylic acid 35V, Positive-QTOF	splash10-0002-9200000000-743d2f19ea30c814c56a	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Xanthylic acid 10V, Positive-QTOF	splash10-0002-9210000000-f36c079a2869c6c7c63d	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Xanthylic acid 20V, Positive-QTOF	splash10-0002-9300000000-0cea344051256ed9d642	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Xanthylic acid 40V, Positive-QTOF	splash10-0002-9300000000-1295bb6a6dfffef31dd2	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Xanthylic acid 20V, Positive-QTOF	splash10-0002-9400000000-7125a3a52d3308d6b367	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Xanthylic acid 40V, Negative-QTOF	splash10-0fb9-9400000000-f93509061523b8f0b012	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Xanthylic acid 10V, Positive-QTOF	splash10-0002-9310000000-a910c200bfc66c8e1c46	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Xanthylic acid 40V, Positive-QTOF	splash10-0002-9000000000-1ff54bb8d71e1ea585f2	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Xanthylic acid 20V, Negative-QTOF	splash10-03fs-9380000000-2a0fbd1929733b4918d1	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Xanthylic acid 10V, Negative-QTOF	splash10-03di-1039000000-f0bd4ff644ac79937301	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Xanthylic acid 10V, Positive-QTOF	splash10-0udi-0913000000-d17f1d77b992fc6e9f04	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Xanthylic acid 20V, Positive-QTOF	splash10-0udi-0900000000-efbdb918f50ba610575d	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Xanthylic acid 40V, Positive-QTOF	splash10-0udi-2900000000-cf070bd16aacd3dcb6fb	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Xanthylic acid 10V, Negative-QTOF	splash10-0imi-6509000000-d931cb1dcaeba678220c	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Xanthylic acid 20V, Negative-QTOF	splash10-0fbc-9300000000-e596281ec38113a9653c	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Xanthylic acid 40V, Negative-QTOF	splash10-004i-9100000000-1caa46ecd17db343ddd3	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Xanthylic acid 10V, Positive-QTOF	splash10-0udi-0900000000-ac450658003af6c0a109	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Xanthylic acid 20V, Positive-QTOF	splash10-0udi-0900000000-448bfe6677d2f8fe1f3c	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Xanthylic acid 40V, Positive-QTOF	splash10-0udi-1900000000-10c12403e596a9b5bf0a	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Xanthylic acid 10V, Negative-QTOF	splash10-03di-3009000000-8a668987618bcd1531e7	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Xanthylic acid 20V, Negative-QTOF	splash10-004i-9000000000-4b2bf772bc8415c9f24c	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Xanthylic acid 40V, Negative-QTOF	splash10-004i-9201000000-907dd40cbb70b7a5c62d	2021-09-23	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

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

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

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

VMH ID

XMP

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Hattori, Kyoji; Kawahara, Shin; Hagiwara, Takeshige. 5'-Xanthylic acid. Jpn. Kokai Tokkyo Koho (1985), 3 pp.

Material Safety Data Sheet (MSDS)

Not Available

General References

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. [PubMed:14756553 ]
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. [PubMed:17038874 ]
Khalil PN, Erb N, Khalil MN, Escherich G, Janka-Schaub GE: Validation and application of a high-performance liquid chromatographic-based assay for determination of the inosine 5'-monophosphate dehydrogenase activity in erythrocytes. J Chromatogr B Analyt Technol Biomed Life Sci. 2006 Sep 14;842(1):1-7. Epub 2006 May 24. [PubMed:16725387 ]
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. Epub 2005 Feb 6. [PubMed:15699053 ]
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. [PubMed:12559919 ]
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. [PubMed:12180982 ]
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. [PubMed:11880114 ]
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 ]
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. [PubMed:11738390 ]
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. [PubMed:11489354 ]
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. [PubMed:10985775 ]
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. [PubMed:10878288 ]
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. [PubMed:10850395 ]
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. [PubMed:10758003 ]
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. [PubMed:10722482 ]
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. [PubMed:10677226 ]
Digits JA, Hedstrom L: Species-specific inhibition of inosine 5'-monophosphate dehydrogenase by mycophenolic acid. Biochemistry. 1999 Nov 16;38(46):15388-97. [PubMed:10563825 ]
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. [PubMed:10545171 ]
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. [PubMed:10545170 ]
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. [PubMed:10441123 ]
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 ]
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 ]
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 ]
Hedstrom L: IMP dehydrogenase: mechanism of action and inhibition. Curr Med Chem. 1999 Jul;6(7):545-60. [PubMed:10390600 ]

Only showing the first 10 proteins. There are 14 proteins in total.

Show all enzymes and transporters

Enzymes

Enzyme Details

1. 5'-nucleotidase

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

Reactions

Xanthylic acid + Water → Xanthosine + Phosphate	details

Enzyme Details

2. Cytosolic 5'-nucleotidase 1B

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

Reactions

Xanthylic acid + Water → Xanthosine + Phosphate	details

Enzyme Details

3. Cytosolic 5'-nucleotidase 1A

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

Reactions

Xanthylic acid + Water → Xanthosine + Phosphate	details

Enzyme Details

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

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

Reactions

Xanthylic acid + Water → Xanthosine + Phosphate	details

Enzyme Details

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

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

Reactions

Xanthylic acid + Water → Xanthosine + Phosphate	details

Enzyme Details

6. Inosine triphosphate pyrophosphatase

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

Reactions

Xanthosine 5-triphosphate + Water → Xanthylic acid + Pyrophosphate	details

Enzyme Details

7. Hypoxanthine-guanine phosphoribosyltransferase

General function:: Involved in hypoxanthine phosphoribosyltransferase activity
Specific function:: Converts guanine to guanosine monophosphate, and hypoxanthine to inosine monophosphate. Transfers the 5-phosphoribosyl group from 5-phosphoribosylpyrophosphate onto the purine. Plays a central role in the generation of purine nucleotides through the purine salvage pathway.
Gene Name:: HPRT1
Uniprot ID:: P00492
Molecular weight:: 24579.155

Reactions

Xanthylic acid + Pyrophosphate → Xanthine + Phosphoribosyl pyrophosphate	details

Enzyme Details

8. GMP synthase [glutamine-hydrolyzing]

General function:: Involved in catalytic activity
Specific function:: Involved in the de novo synthesis of guanine nucleotides which are not only essential for DNA and RNA synthesis, but also provide GTP, which is involved in a number of cellular processes important for cell division.
Gene Name:: GMPS
Uniprot ID:: P49915
Molecular weight:: 76714.79

Reactions

Adenosine triphosphate + Xanthylic acid + Glutamine + Water → Adenosine monophosphate + Pyrophosphate + Guanosine monophosphate + Glutamic acid	details
Adenosine triphosphate + Xanthylic acid + Ammonia → Adenosine monophosphate + Pyrophosphate + Guanosine monophosphate	details

Enzyme Details

9. Bis(5'-nucleosyl)-tetraphosphatase [asymmetrical]

General function:: Involved in hydrolase activity
Specific function:: Asymmetrically hydrolyzes Ap4A to yield AMP and ATP. Plays a major role in maintaining homeostasis.
Gene Name:: NUDT2
Uniprot ID:: P50583
Molecular weight:: 16829.09

Reactions

P1,P4-Bis(5'-xanthosyl) tetraphosphate + Water → Xanthosine 5-triphosphate + Xanthylic acid	details

Enzyme Details

10. Inosine-5'-monophosphate dehydrogenase 2

General function:: Involved in catalytic activity
Specific function:: Catalyzes the conversion of inosine 5'-phosphate (IMP) to xanthosine 5'-phosphate (XMP), the first committed and rate-limiting step in the de novo synthesis of guanine nucleotides, and therefore plays an important role in the regulation of cell growth. Could also have a single-stranded nucleic acid-binding activity and could play a role in RNA and/or DNA metabolism. It may also have a role in the development of malignancy and the growth progression of some tumors.
Gene Name:: IMPDH2
Uniprot ID:: P12268
Molecular weight:: 55804.495

Reactions

Inosinic acid + NAD + Water → Xanthylic acid + NADH	details
Inosinic acid + NAD + Water → Xanthylic acid + NADH + Hydrogen Ion	details

Only showing the first 10 proteins. There are 14 proteins in total.

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Showing metabocard for Xanthylic acid (HMDB0001554)

MOL for HMDB0001554 (Xanthylic acid)

3D MOL for HMDB0001554 (Xanthylic acid)

3D SDF for HMDB0001554 (Xanthylic acid)

3D-SDF for HMDB0001554 (Xanthylic acid)

PDB for HMDB0001554 (Xanthylic acid)

3D PDB for HMDB0001554 (Xanthylic acid)

SMILES for HMDB0001554 (Xanthylic acid)

INCHI for HMDB0001554 (Xanthylic acid)

Structure for HMDB0001554 (Xanthylic acid)

3D Structure for HMDB0001554 (Xanthylic acid)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

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Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes

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