Showing metabocard for 1,3,7-Trimethyluric acid (MMDBc0000582)

Record Information
Version1.0
StatusDetected and Quantified
Creation Date2020-12-10 18:50:26 UTC
Update Date2024-04-30 19:33:06 UTC
Metabolite IDMMDBc0000582
Metabolite Identification
Common Name1,3,7-Trimethyluric acid
Description1,3,7-Trimethyluric acid is a methyl derivative of uric acid, found occasionally in human urine. 1,3,7-Trimethyluracil 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
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for #<Metabolite:0x00007f9233fb9330>


  Mrv1652309042000262D          

 15 16  0  0  0  0            999 V2000
   -0.3984   -2.1500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435   -1.3654    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435   -0.0305    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6284   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4534   -0.6979    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    0.1271    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7845    0.1271    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701   -1.1104    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556   -2.3479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7845   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    0.9521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  2  6  1  0  0  0  0
  6  7  2  0  0  0  0
  4  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
  3 12  1  0  0  0  0
 12 13  2  0  0  0  0
 11 14  1  0  0  0  0
  8 15  1  0  0  0  0
M  END
Download

3D MOL for #<Metabolite:0x00007f9233fb9330>

HMDB0002123
     RDKit          3D
1,3,7-Trimethyluric acid
 25 26  0  0  0  0  0  0  0  0999 V2000
   -1.0054    3.0639    0.1023 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7801    1.6353    0.0984 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4943    1.2206    0.0872 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4561    2.0621    0.0804 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7655   -0.1239    0.0831 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2633   -1.0483    0.0903 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2930   -2.2701    0.0839 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6333   -2.0825    0.0730 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4432   -3.0402    0.0649 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9389   -0.7930    0.0723 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2427   -0.1493    0.0624 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5184   -0.5917    0.1014 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5940   -1.5783    0.1089 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7781    0.7405    0.1055 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9950    1.1243    0.1161 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2158    3.5366   -0.5189 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0159    3.3351   -0.2553 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8271    3.4119    1.1506 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2410   -3.1640    0.0871 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3585    0.3551    1.0424 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1849    0.6760   -0.6982 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0517   -0.8257   -0.2038 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5134   -1.1867   -0.3517 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8258   -1.8022    1.1746 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2889   -2.5057   -0.4169 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  2  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
  6 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  2  0
 14  2  1  0
 10  5  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  7 19  1  0
 11 20  1  0
 11 21  1  0
 11 22  1  0
 13 23  1  0
 13 24  1  0
 13 25  1  0
M  END
Download

3D SDF for #<Metabolite:0x00007f9233fb9330>


  Mrv1652309042000262D          

 15 16  0  0  0  0            999 V2000
   -0.3984   -2.1500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435   -1.3654    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435   -0.0305    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6284   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4534   -0.6979    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    0.1271    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7845    0.1271    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701   -1.1104    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556   -2.3479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7845   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    0.9521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  2  6  1  0  0  0  0
  6  7  2  0  0  0  0
  4  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
  3 12  1  0  0  0  0
 12 13  2  0  0  0  0
 11 14  1  0  0  0  0
  8 15  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0000582

> <DATABASE_NAME>
MIME

> <SMILES>
CN1C(=O)NC2=C1C(=O)N(C)C(=O)N2C

> <INCHI_IDENTIFIER>
InChI=1S/C8H10N4O3/c1-10-4-5(9-7(10)14)11(2)8(15)12(3)6(4)13/h1-3H3,(H,9,14)

> <INCHI_KEY>
BYXCFUMGEBZDDI-UHFFFAOYSA-N

> <FORMULA>
C8H10N4O3

> <MOLECULAR_WEIGHT>
210.19

> <EXACT_MASS>
210.075290206

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
25

> <JCHEM_AVERAGE_POLARIZABILITY>
19.815503960334613

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
-0.49

> <JCHEM_LOGP>
-0.8731647386666664

> <ALOGPS_LOGS>
-0.87

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.463980111537293

> <JCHEM_PKA_STRONGEST_BASIC>
-5.670348659606715

> <JCHEM_POLAR_SURFACE_AREA>
72.96000000000001

> <JCHEM_REFRACTIVITY>
60.3187

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.83e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1,3,7-trimethyluric acid

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for #<Metabolite:0x00007f9233fb9330>

HMDB0002123
     RDKit          3D
1,3,7-Trimethyluric acid
 25 26  0  0  0  0  0  0  0  0999 V2000
   -1.0054    3.0639    0.1023 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7801    1.6353    0.0984 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4943    1.2206    0.0872 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4561    2.0621    0.0804 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7655   -0.1239    0.0831 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2633   -1.0483    0.0903 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2930   -2.2701    0.0839 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6333   -2.0825    0.0730 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4432   -3.0402    0.0649 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9389   -0.7930    0.0723 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2427   -0.1493    0.0624 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5184   -0.5917    0.1014 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5940   -1.5783    0.1089 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7781    0.7405    0.1055 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9950    1.1243    0.1161 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2158    3.5366   -0.5189 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0159    3.3351   -0.2553 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8271    3.4119    1.1506 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2410   -3.1640    0.0871 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3585    0.3551    1.0424 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1849    0.6760   -0.6982 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0517   -0.8257   -0.2038 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5134   -1.1867   -0.3517 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8258   -1.8022    1.1746 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2889   -2.5057   -0.4169 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  2  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
  6 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  2  0
 14  2  1  0
 10  5  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  7 19  1  0
 11 20  1  0
 11 21  1  0
 11 22  1  0
 13 23  1  0
 13 24  1  0
 13 25  1  0
M  END
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PDB for #<Metabolite:0x00007f9233fb9330>

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  C   UNK     0      -0.744  -4.013   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0      -0.268  -2.549   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0       1.197  -2.073   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.197  -0.533   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0      -0.268  -0.057   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0      -1.173  -1.303   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -2.713  -1.303   0.000  0.00  0.00           O+0
HETATM    8  N   UNK     0       2.530   0.237   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0       3.864  -0.533   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       5.198   0.237   0.000  0.00  0.00           O+0
HETATM   11  N   UNK     0       3.864  -2.073   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0       2.530  -2.843   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       2.530  -4.383   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       5.198  -2.843   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.530   1.777   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    6                                                  
CONECT    3    2    4   12                                                  
CONECT    4    3    5    8                                                  
CONECT    5    4    6                                                       
CONECT    6    5    2    7                                                  
CONECT    7    6                                                            
CONECT    8    4    9   15                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   14                                                  
CONECT   12   11    3   13                                                  
CONECT   13   12                                                            
CONECT   14   11                                                            
CONECT   15    8                                                            
MASTER        0    0    0    0    0    0    0    0   15    0   32    0
END
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3D PDB for #<Metabolite:0x00007f9233fb9330>

COMPND    HMDB0002123
HETATM    1  C1  UNL     1      -1.005   3.064   0.102  1.00  0.00           C  
HETATM    2  N1  UNL     1      -0.780   1.635   0.098  1.00  0.00           N  
HETATM    3  C2  UNL     1       0.494   1.221   0.087  1.00  0.00           C  
HETATM    4  O1  UNL     1       1.456   2.062   0.080  1.00  0.00           O  
HETATM    5  C3  UNL     1       0.766  -0.124   0.083  1.00  0.00           C  
HETATM    6  C4  UNL     1      -0.263  -1.048   0.090  1.00  0.00           C  
HETATM    7  N2  UNL     1       0.293  -2.270   0.084  1.00  0.00           N  
HETATM    8  C5  UNL     1       1.633  -2.083   0.073  1.00  0.00           C  
HETATM    9  O2  UNL     1       2.443  -3.040   0.065  1.00  0.00           O  
HETATM   10  N3  UNL     1       1.939  -0.793   0.072  1.00  0.00           N  
HETATM   11  C6  UNL     1       3.243  -0.149   0.062  1.00  0.00           C  
HETATM   12  N4  UNL     1      -1.518  -0.592   0.101  1.00  0.00           N  
HETATM   13  C7  UNL     1      -2.594  -1.578   0.109  1.00  0.00           C  
HETATM   14  C8  UNL     1      -1.778   0.740   0.105  1.00  0.00           C  
HETATM   15  O3  UNL     1      -2.995   1.124   0.116  1.00  0.00           O  
HETATM   16  H1  UNL     1      -0.216   3.537  -0.519  1.00  0.00           H  
HETATM   17  H2  UNL     1      -2.016   3.335  -0.255  1.00  0.00           H  
HETATM   18  H3  UNL     1      -0.827   3.412   1.151  1.00  0.00           H  
HETATM   19  H4  UNL     1      -0.241  -3.164   0.087  1.00  0.00           H  
HETATM   20  H5  UNL     1       3.359   0.355   1.042  1.00  0.00           H  
HETATM   21  H6  UNL     1       3.185   0.676  -0.698  1.00  0.00           H  
HETATM   22  H7  UNL     1       4.052  -0.826  -0.204  1.00  0.00           H  
HETATM   23  H8  UNL     1      -3.513  -1.187  -0.352  1.00  0.00           H  
HETATM   24  H9  UNL     1      -2.826  -1.802   1.175  1.00  0.00           H  
HETATM   25  H10 UNL     1      -2.289  -2.506  -0.417  1.00  0.00           H  
CONECT    1    2   16   17   18
CONECT    2    3   14
CONECT    3    4    4    5
CONECT    5    6    6   10
CONECT    6    7   12
CONECT    7    8   19
CONECT    8    9    9   10
CONECT   10   11
CONECT   11   20   21   22
CONECT   12   13   14
CONECT   13   23   24   25
CONECT   14   15   15
END
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SMILES for #<Metabolite:0x00007f9233fb9330>

CN1C(=O)NC2=C1C(=O)N(C)C(=O)N2C
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INCHI for #<Metabolite:0x00007f9233fb9330>

InChI=1S/C8H10N4O3/c1-10-4-5(9-7(10)14)11(2)8(15)12(3)6(4)13/h1-3H3,(H,9,14)
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Synonyms
ValueSource
1,3,7-Trimethyl-2,3,6,7,8,9-hexahydro-1H-purine-2,6,8-trioneChEBI
1,3,7-TrimethylurateChEBI
7,9-Dihydro-1,3,7-trimethyl-1H-purine-2,6,8(3H)-trioneChEBI
8-OxocaffeineChEBI
8-Oxy-caffeineChEBI
1,3,7-TrimethylateGenerator
1,3,7-Trimethylic acidGenerator
1,3, 7-Trimethyluric acidHMDB
1,3,7-Trimethyl-7,9-dihydro-1H-purine-2,6,8(3H)-trioneHMDB
2,6,8-Trihydroxy-1,3,7-trimethylpurineHMDB
8-Hydroxy-1,3,7-trimethyl-3,7-dihydro-1H-purine-2,6-dioneHMDB
Trimethyl uric acidHMDB
Molecular FormulaC8H10N4O3
Average Mass210.19
Monoisotopic Mass210.075290206
IUPAC Name1,3,7-trimethyl-2,3,6,7,8,9-hexahydro-1H-purine-2,6,8-trione
Traditional Name1,3,7-trimethyluric acid
CAS Registry NumberNot Available
SMILES
CN1C(=O)NC2=C1C(=O)N(C)C(=O)N2C
InChI Identifier
InChI=1S/C8H10N4O3/c1-10-4-5(9-7(10)14)11(2)8(15)12(3)6(4)13/h1-3H3,(H,9,14)
InChI KeyBYXCFUMGEBZDDI-UHFFFAOYSA-N