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Showing NP-Card for 3,7-Dimethyluric acid (NP0001152)

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Record Information
Version2.0
Created at2006-05-22 14:17:30 UTC
Updated at2021-10-07 20:38:45 UTC
NP-MRD IDNP0001152
Secondary Accession NumbersNone
Natural Product Identification
Common Name3,7-Dimethyluric acid
Description3,7-Dimethyluric acid is a methyl derivative of uric acid, found occasionally in human urine. 3,7-Dimethyluric is one of the purine components in urinary calculi. Methylated purines originate from the metabolism of methylxanthines (caffeine, theophylline and theobromine). Methyluric acids are indistinguishable from uric acid by simple methods routinely used in clinical laboratories, requiring the use of high-performance liquid chromatography (HPLC). Purine derivatives in urinary calculi could be considered markers of abnormal purine metabolism. The content of a purine derivative in stone depends on its average urinary excretion in the general population, similarity to the chemical structure of uric acid, and content of the latter in stone. This suggests that purines in stones represent a solid solution with uric acid as solvent. It is also plausible that methylxanthines, ubiquitous components of the diet and drugs, are involved in the pathogenesis of urolithiasis. Caffeine is metabolized via successive pathways mainly catalyzed by CYP1A2, xanthine oxidase or N-acetyltransferase-2 to give 14 different metabolites. CYP1A2 activity shows an inter-individual variability among the population. CYP1A2, an isoform of the CYP1A cytochrome P450 super-family, is involved in the metabolism of many drugs and plays a potentially important role in the induction of chemical carcinogenesis (PMID: 11712316 , 15833286 , 3506820 , 15013152 ).
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0001152 (3,7-Dimethyluric acid)


  Mrv1652309042000252D          

 14 15  0  0  0  0            999 V2000
   19.6448   -4.8676    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.8431   -3.2173    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.4139   -5.6926    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.3382   -4.2035    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.8431   -5.6926    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.3382   -5.5315    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.1284   -4.4550    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.5575   -5.2800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5575   -4.4550    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8197   -4.8676    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8431   -4.0424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1284   -5.2800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5946   -3.4193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8431   -6.5177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 10  2  0  0  0  0
  2 11  2  0  0  0  0
  3 12  2  0  0  0  0
  4  9  1  0  0  0  0
  4 10  1  0  0  0  0
  4 13  1  0  0  0  0
  5  8  1  0  0  0  0
  5 12  1  0  0  0  0
  5 14  1  0  0  0  0
  6  8  1  0  0  0  0
  6 10  1  0  0  0  0
  7 11  1  0  0  0  0
  7 12  1  0  0  0  0
  8  9  2  0  0  0  0
  9 11  1  0  0  0  0
M  END
Download

3D MOL for NP0001152 (3,7-Dimethyluric acid)

HMDB0001982
     RDKit          3D
3,7-Dimethyluric acid
 22 23  0  0  0  0  0  0  0  0999 V2000
    2.8278   -0.9569   -0.0230 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7021   -0.0461    0.0524 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9172    1.2677    0.2290 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0842    1.7247    0.3307 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8669    2.1249    0.3002 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3995    1.7071    0.1998 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3891    2.4861    0.2633 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6511    0.3727    0.0193 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4353   -0.4883   -0.0511 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0925   -1.7162   -0.2283 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4320   -1.5958   -0.2623 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1919   -2.5868   -0.4175 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7967   -0.3194   -0.1119 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1517    0.1801   -0.0977 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7025   -0.4814   -0.4975 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5026   -1.8792   -0.5310 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0934   -1.2399    1.0279 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0611    3.1403    0.4377 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5017   -2.5714   -0.3161 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6262    0.0653    0.9205 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7129   -0.4145   -0.8662 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2511    1.2270   -0.3782 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  0
  9  2  1  0
 13  8  1  0
  1 15  1  0
  1 16  1  0
  1 17  1  0
  5 18  1  0
 10 19  1  0
 14 20  1  0
 14 21  1  0
 14 22  1  0
M  END
Download

3D SDF for NP0001152 (3,7-Dimethyluric acid)


  Mrv1652309042000252D          

 14 15  0  0  0  0            999 V2000
   19.6448   -4.8676    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.8431   -3.2173    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.4139   -5.6926    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.3382   -4.2035    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.8431   -5.6926    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.3382   -5.5315    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.1284   -4.4550    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.5575   -5.2800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5575   -4.4550    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8197   -4.8676    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8431   -4.0424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1284   -5.2800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5946   -3.4193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8431   -6.5177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 10  2  0  0  0  0
  2 11  2  0  0  0  0
  3 12  2  0  0  0  0
  4  9  1  0  0  0  0
  4 10  1  0  0  0  0
  4 13  1  0  0  0  0
  5  8  1  0  0  0  0
  5 12  1  0  0  0  0
  5 14  1  0  0  0  0
  6  8  1  0  0  0  0
  6 10  1  0  0  0  0
  7 11  1  0  0  0  0
  7 12  1  0  0  0  0
  8  9  2  0  0  0  0
  9 11  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0001152

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CN1C(=O)NC2=C1C(=O)NC(=O)N2C

> <INCHI_IDENTIFIER>
InChI=1S/C7H8N4O3/c1-10-3-4(8-6(10)13)11(2)7(14)9-5(3)12/h1-2H3,(H,8,13)(H,9,12,14)

> <INCHI_KEY>
HMLZLHKHNBLLJD-UHFFFAOYSA-N

> <FORMULA>
C7H8N4O3

> <MOLECULAR_WEIGHT>
196.1634

> <EXACT_MASS>
196.059640142

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
22

> <JCHEM_AVERAGE_POLARIZABILITY>
17.69108590108656

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3,7-dimethyl-2,3,6,7,8,9-hexahydro-1H-purine-2,6,8-trione

> <ALOGPS_LOGP>
-0.61

> <JCHEM_LOGP>
-1.0968408043333333

> <ALOGPS_LOGS>
-1.31

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.314126160972181

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.12966218404884

> <JCHEM_PKA_STRONGEST_BASIC>
-6.024680278721663

> <JCHEM_POLAR_SURFACE_AREA>
81.75

> <JCHEM_REFRACTIVITY>
55.422000000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.62e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3,7-dimethyluric acid

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for NP0001152 (3,7-Dimethyluric acid)

HMDB0001982
     RDKit          3D
3,7-Dimethyluric acid
 22 23  0  0  0  0  0  0  0  0999 V2000
    2.8278   -0.9569   -0.0230 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7021   -0.0461    0.0524 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9172    1.2677    0.2290 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0842    1.7247    0.3307 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8669    2.1249    0.3002 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3995    1.7071    0.1998 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3891    2.4861    0.2633 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6511    0.3727    0.0193 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4353   -0.4883   -0.0511 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0925   -1.7162   -0.2283 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4320   -1.5958   -0.2623 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1919   -2.5868   -0.4175 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7967   -0.3194   -0.1119 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1517    0.1801   -0.0977 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7025   -0.4814   -0.4975 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5026   -1.8792   -0.5310 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0934   -1.2399    1.0279 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0611    3.1403    0.4377 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5017   -2.5714   -0.3161 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6262    0.0653    0.9205 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7129   -0.4145   -0.8662 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2511    1.2270   -0.3782 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  0
  9  2  1  0
 13  8  1  0
  1 15  1  0
  1 16  1  0
  1 17  1  0
  5 18  1  0
 10 19  1  0
 14 20  1  0
 14 21  1  0
 14 22  1  0
M  END
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PDB for NP0001152 (3,7-Dimethyluric acid)

HEADER    PROTEIN                                 04-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-20         0                                  
HETATM    1  O   UNK     0      36.670  -9.086   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      31.440  -6.006   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      28.773 -10.626   0.000  0.00  0.00           O+0
HETATM    4  N   UNK     0      34.231  -7.847   0.000  0.00  0.00           N+0
HETATM    5  N   UNK     0      31.440 -10.626   0.000  0.00  0.00           N+0
HETATM    6  N   UNK     0      34.231 -10.325   0.000  0.00  0.00           N+0
HETATM    7  N   UNK     0      30.106  -8.316   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0      32.774  -9.856   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      32.774  -8.316   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      35.130  -9.086   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      31.440  -7.546   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      30.106  -9.856   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      34.710  -6.383   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      31.440 -12.166   0.000  0.00  0.00           C+0
CONECT    1   10                                                            
CONECT    2   11                                                            
CONECT    3   12                                                            
CONECT    4    9   10   13                                                  
CONECT    5    8   12   14                                                  
CONECT    6    8   10                                                       
CONECT    7   11   12                                                       
CONECT    8    5    6    9                                                  
CONECT    9    4    8   11                                                  
CONECT   10    1    4    6                                                  
CONECT   11    2    7    9                                                  
CONECT   12    3    5    7                                                  
CONECT   13    4                                                            
CONECT   14    5                                                            
MASTER        0    0    0    0    0    0    0    0   14    0   30    0
END
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3D PDB for NP0001152 (3,7-Dimethyluric acid)

COMPND    HMDB0001982
HETATM    1  C1  UNL     1       2.828  -0.957  -0.023  1.00  0.00           C  
HETATM    2  N1  UNL     1       1.702  -0.046   0.052  1.00  0.00           N  
HETATM    3  C2  UNL     1       1.917   1.268   0.229  1.00  0.00           C  
HETATM    4  O1  UNL     1       3.084   1.725   0.331  1.00  0.00           O  
HETATM    5  N2  UNL     1       0.867   2.125   0.300  1.00  0.00           N  
HETATM    6  C3  UNL     1      -0.400   1.707   0.200  1.00  0.00           C  
HETATM    7  O2  UNL     1      -1.389   2.486   0.263  1.00  0.00           O  
HETATM    8  C4  UNL     1      -0.651   0.373   0.019  1.00  0.00           C  
HETATM    9  C5  UNL     1       0.435  -0.488  -0.051  1.00  0.00           C  
HETATM   10  N3  UNL     1      -0.093  -1.716  -0.228  1.00  0.00           N  
HETATM   11  C6  UNL     1      -1.432  -1.596  -0.262  1.00  0.00           C  
HETATM   12  O3  UNL     1      -2.192  -2.587  -0.418  1.00  0.00           O  
HETATM   13  N4  UNL     1      -1.797  -0.319  -0.112  1.00  0.00           N  
HETATM   14  C7  UNL     1      -3.152   0.180  -0.098  1.00  0.00           C  
HETATM   15  H1  UNL     1       3.703  -0.481  -0.497  1.00  0.00           H  
HETATM   16  H2  UNL     1       2.503  -1.879  -0.531  1.00  0.00           H  
HETATM   17  H3  UNL     1       3.093  -1.240   1.028  1.00  0.00           H  
HETATM   18  H4  UNL     1       1.061   3.140   0.438  1.00  0.00           H  
HETATM   19  H5  UNL     1       0.502  -2.571  -0.316  1.00  0.00           H  
HETATM   20  H6  UNL     1      -3.626   0.065   0.921  1.00  0.00           H  
HETATM   21  H7  UNL     1      -3.713  -0.415  -0.866  1.00  0.00           H  
HETATM   22  H8  UNL     1      -3.251   1.227  -0.378  1.00  0.00           H  
CONECT    1    2   15   16   17
CONECT    2    3    9
CONECT    3    4    4    5
CONECT    5    6   18
CONECT    6    7    7    8
CONECT    8    9    9   13
CONECT    9   10
CONECT   10   11   19
CONECT   11   12   12   13
CONECT   13   14
CONECT   14   20   21   22
END
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SMILES for NP0001152 (3,7-Dimethyluric acid)

CN1C(=O)NC2=C1C(=O)NC(=O)N2C
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INCHI for NP0001152 (3,7-Dimethyluric acid)

InChI=1S/C7H8N4O3/c1-10-3-4(8-6(10)13)11(2)7(14)9-5(3)12/h1-2H3,(H,8,13)(H,9,12,14)
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View in JSmol
Synonyms
ValueSource
3,7-DimethylateGenerator
3,7-Dimethylic acidGenerator
37-Dimethyluric acidHMDB
37-DimethylateHMDB
37-Dimethylic acidHMDB
3,7-Dimethyl-2,6,8-trihydroxypurineHMDB
3,7-Dimethyl-7,9-dihydro-1H-purine-2,6,8(3H)-trioneHMDB
3,7-DMUHMDB
Chemical FormulaC7H8N4O3
Average Mass196.1634 Da
Monoisotopic Mass196.05964 Da
IUPAC Name3,7-dimethyl-2,3,6,7,8,9-hexahydro-1H-purine-2,6,8-trione
Traditional Name3,7-dimethyluric acid
CAS Registry Number13087-49-5
SMILES
CN1C(=O)NC2=C1C(=O)NC(=O)N2C
InChI Identifier
InChI=1S/C7H8N4O3/c1-10-3-4(8-6(10)13)11(2)7(14)9-5(3)12/h1-2H3,(H,8,13)(H,9,12,14)
InChI KeyHMLZLHKHNBLLJD-UHFFFAOYSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, simulated)varshavi.d26@gmail.comNot AvailableNot Available2021-08-10View Spectrum
Species
Species of Origin
Species NameSourceReference
Abelmoschus esculentusFooDB
Actinidia chinensisFooDB
Agaricus bisporusFooDB
AgaveFooDB
Allium ampeloprasumFooDB
Allium ascalonicumFooDB
Allium cepaFooDB
Allium cepa L.FooDB
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Chemical Taxonomy
Description Belongs to the class of organic compounds known as xanthines. These are purine derivatives with a ketone group conjugated at carbons 2 and 6 of the purine moiety.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassImidazopyrimidines
Sub ClassPurines and purine derivatives
Direct ParentXanthines
Alternative Parents
Substituents
  • Xanthine
  • 6-oxopurine
  • Purinone
  • Alkaloid or derivatives
  • Pyrimidone
  • N-substituted imidazole
  • Pyrimidine
  • Azole
  • Imidazole
  • Heteroaromatic compound
  • Vinylogous amide
  • Lactam
  • Urea
  • Azacycle
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP-1.33Gaspari, F., Vigano, G., Orisio, S., Bonati, M., Livio, M., & Remuzzi, G. (1987). Aspirin prolongs bleeding time in uremia by a mechanism distinct from platelet cyclooxygenase inhibition. The Journal of clinical investigation, 79(6), 1788-1797.
Predicted Properties
PropertyValueSource
Water Solubility9.62 g/LALOGPS
logP-0.61ALOGPS
logP-1.1ChemAxon
logS-1.3ALOGPS
pKa (Strongest Acidic)8.13ChemAxon
pKa (Strongest Basic)-6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area81.75 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity55.42 m³·mol⁻¹ChemAxon
Polarizability17.69 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0001982
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB022780
KNApSAcK IDNot Available
Chemspider ID74994
KEGG Compound IDC16360
BioCyc IDCPD-12482
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound83126
PDB IDNot Available
ChEBI ID68531
Good Scents IDNot Available
References
General References
  1. Safranow K, Machoy Z: Simultaneous determination of 16 purine derivatives in urinary calculi by gradient reversed-phase high-performance liquid chromatography with UV detection. J Chromatogr B Analyt Technol Biomed Life Sci. 2005 May 25;819(2):229-35. [PubMed:15833286 ]
  2. Safranow K: [Identification and quantitation of purine derivatives in urinary calculi as markers of abnormal purine metabolism by using high-performance liquid chromatography (HPLC)]. Ann Acad Med Stetin. 2000;46:35-49. [PubMed:11712316 ]