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Showing metabocard for 1,7-Dimethyluric acid (HMDB0011103)

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enzymes (2) Show 2 proteins
Record Information
Version5.0
StatusDetected and Quantified
Creation Date2008-10-16 22:22:16 UTC
Update Date2023-02-21 17:17:26 UTC
HMDB IDHMDB0011103
Secondary Accession Numbers
  • HMDB11103
Metabolite Identification
Common Name1,7-Dimethyluric acid
Description1,7-Dimethyluric acid, also known as 1,7-dimethylate, 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. 1,7-Dimethyluric acid is an extremely weak basic (essentially neutral) compound (based on its pKa). 1,7-Dimethyluric acid exists in all living organisms, ranging from bacteria to humans. 1,7-dimethyluric acid can be biosynthesized from paraxanthine through the action of the enzymes cytochrome P450 1A2 and cytochrome P450 2A6. In humans, 1,7-dimethyluric acid is involved in caffeine metabolism.
Structure
Data?1676999846
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0011103 (1,7-Dimethyluric acid)


  Mrv1652309042000332D          

 14 15  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  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
M  END
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3D MOL for HMDB0011103 (1,7-Dimethyluric acid)

HMDB0011103
     RDKit          3D
1,7-Dimethyluric acid
 22 23  0  0  0  0  0  0  0  0999 V2000
    2.9176   -1.3850   -0.0370 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8084   -0.4438   -0.0351 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0255    0.8840   -0.0839 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2165    1.2919   -0.1315 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0287    1.7870   -0.0840 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2632    1.4079   -0.0345 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4398    2.0815   -0.0220 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4247    1.1658    0.0359 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6666    1.3597    0.0657 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8700   -0.0486    0.0588 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5682   -1.3197    0.1198 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5269    0.0491    0.0168 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5259   -0.8453    0.0150 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2791   -2.0628    0.0612 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7094   -2.2780    0.5872 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1617   -1.7504   -1.0552 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8375   -0.9268    0.3813 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2010    2.8301   -0.1225 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5657    3.1244   -0.0518 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8500   -1.5715   -0.9442 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5399   -1.2381    0.6635 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9961   -2.1112    0.5966 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  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
 13 14  2  0
 13  2  1  0
 12  6  2  0
  1 15  1  0
  1 16  1  0
  1 17  1  0
  5 18  1  0
  7 19  1  0
 11 20  1  0
 11 21  1  0
 11 22  1  0
M  END
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3D SDF for HMDB0011103 (1,7-Dimethyluric acid)


  Mrv1652309042000332D          

 14 15  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  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
M  END
> <DATABASE_ID>
HMDB0011103

> <DATABASE_NAME>
hmdb

> <SMILES>
CN1C(=O)NC2=C1C(=O)N(C)C(=O)N2

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

> <INCHI_KEY>
NOFNCLGCUJJPKU-UHFFFAOYSA-N

> <FORMULA>
C7H8N4O3

> <MOLECULAR_WEIGHT>
196.1634

> <EXACT_MASS>
196.059640142

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
22

> <JCHEM_AVERAGE_POLARIZABILITY>
18.06105286981368

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2,8-dihydroxy-1,7-dimethyl-6,7-dihydro-1H-purin-6-one

> <ALOGPS_LOGP>
-0.81

> <JCHEM_LOGP>
0.47086302666666646

> <ALOGPS_LOGS>
-1.36

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
10.480737061798054

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.9649633548664176

> <JCHEM_PKA_STRONGEST_BASIC>
-1.8635946742632101

> <JCHEM_POLAR_SURFACE_AREA>
90.95

> <JCHEM_REFRACTIVITY>
48.9246

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.49e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1,7-dimethyluric acid

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for HMDB0011103 (1,7-Dimethyluric acid)

HMDB0011103
     RDKit          3D
1,7-Dimethyluric acid
 22 23  0  0  0  0  0  0  0  0999 V2000
    2.9176   -1.3850   -0.0370 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8084   -0.4438   -0.0351 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0255    0.8840   -0.0839 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2165    1.2919   -0.1315 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0287    1.7870   -0.0840 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2632    1.4079   -0.0345 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4398    2.0815   -0.0220 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4247    1.1658    0.0359 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6666    1.3597    0.0657 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8700   -0.0486    0.0588 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5682   -1.3197    0.1198 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5269    0.0491    0.0168 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5259   -0.8453    0.0150 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2791   -2.0628    0.0612 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7094   -2.2780    0.5872 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1617   -1.7504   -1.0552 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8375   -0.9268    0.3813 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2010    2.8301   -0.1225 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5657    3.1244   -0.0518 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8500   -1.5715   -0.9442 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5399   -1.2381    0.6635 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9961   -2.1112    0.5966 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  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
 13 14  2  0
 13  2  1  0
 12  6  2  0
  1 15  1  0
  1 16  1  0
  1 17  1  0
  5 18  1  0
  7 19  1  0
 11 20  1  0
 11 21  1  0
 11 22  1  0
M  END
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PDB for HMDB0011103 (1,7-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  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
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                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   14                                                  
CONECT   12   11    3   13                                                  
CONECT   13   12                                                            
CONECT   14   11                                                            
MASTER        0    0    0    0    0    0    0    0   14    0   30    0
END
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3D PDB for HMDB0011103 (1,7-Dimethyluric acid)

COMPND    HMDB0011103
HETATM    1  C1  UNL     1       2.918  -1.385  -0.037  1.00  0.00           C  
HETATM    2  N1  UNL     1       1.808  -0.444  -0.035  1.00  0.00           N  
HETATM    3  C2  UNL     1       2.025   0.884  -0.084  1.00  0.00           C  
HETATM    4  O1  UNL     1       3.217   1.292  -0.132  1.00  0.00           O  
HETATM    5  N2  UNL     1       1.029   1.787  -0.084  1.00  0.00           N  
HETATM    6  C3  UNL     1      -0.263   1.408  -0.034  1.00  0.00           C  
HETATM    7  N3  UNL     1      -1.440   2.081  -0.022  1.00  0.00           N  
HETATM    8  C4  UNL     1      -2.425   1.166   0.036  1.00  0.00           C  
HETATM    9  O2  UNL     1      -3.667   1.360   0.066  1.00  0.00           O  
HETATM   10  N4  UNL     1      -1.870  -0.049   0.059  1.00  0.00           N  
HETATM   11  C5  UNL     1      -2.568  -1.320   0.120  1.00  0.00           C  
HETATM   12  C6  UNL     1      -0.527   0.049   0.017  1.00  0.00           C  
HETATM   13  C7  UNL     1       0.526  -0.845   0.015  1.00  0.00           C  
HETATM   14  O3  UNL     1       0.279  -2.063   0.061  1.00  0.00           O  
HETATM   15  H1  UNL     1       2.709  -2.278   0.587  1.00  0.00           H  
HETATM   16  H2  UNL     1       3.162  -1.750  -1.055  1.00  0.00           H  
HETATM   17  H3  UNL     1       3.837  -0.927   0.381  1.00  0.00           H  
HETATM   18  H4  UNL     1       1.201   2.830  -0.122  1.00  0.00           H  
HETATM   19  H5  UNL     1      -1.566   3.124  -0.052  1.00  0.00           H  
HETATM   20  H6  UNL     1      -2.850  -1.571  -0.944  1.00  0.00           H  
HETATM   21  H7  UNL     1      -3.540  -1.238   0.664  1.00  0.00           H  
HETATM   22  H8  UNL     1      -1.996  -2.111   0.597  1.00  0.00           H  
CONECT    1    2   15   16   17
CONECT    2    3   13
CONECT    3    4    4    5
CONECT    5    6   18
CONECT    6    7   12   12
CONECT    7    8   19
CONECT    8    9    9   10
CONECT   10   11   12
CONECT   11   20   21   22
CONECT   12   13
CONECT   13   14   14
END
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SMILES for HMDB0011103 (1,7-Dimethyluric acid)

CN1C(=O)NC2=C1C(=O)N(C)C(=O)N2
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INCHI for HMDB0011103 (1,7-Dimethyluric acid)

InChI=1S/C7H8N4O3/c1-10-3-4(8-6(10)13)9-7(14)11(2)5(3)12/h1-2H3,(H,8,13)(H,9,14)
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View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
ValueSource
1,7-DimethylateGenerator
1,7-Dimethylic acidGenerator
1,7-DimethylurateHMDB
7,9-Dihydro-1,7-dimethyl-1H-purine-2,6,8(3H)-trioneHMDB
1,7-Dimethyluric acidHMDB
Chemical FormulaC7H8N4O3
Average Molecular Weight196.1634
Monoisotopic Molecular Weight196.059640142
IUPAC Name2,8-dihydroxy-1,7-dimethyl-6,7-dihydro-1H-purin-6-one
Traditional Name1,7-dimethyluric acid
CAS Registry Number33868-03-0
SMILES
CN1C(=O)NC2=C1C(=O)N(C)C(=O)N2
InChI Identifier
InChI=1S/C7H8N4O3/c1-10-3-4(8-6(10)13)9-7(14)11(2)5(3)12/h1-2H3,(H,8,13)(H,9,14)
InChI KeyNOFNCLGCUJJPKU-UHFFFAOYSA-N
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
  • Hydroxypyrimidine
  • N-substituted imidazole
  • Pyrimidine
  • Imidazole
  • Azole
  • Heteroaromatic compound
  • Lactam
  • Azacycle
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Biological locationSource
Process
Naturally occurring process
Role
Biological roleIndustrial application
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M-H]-MetCCS_train_neg134.05830932474
[M-H]-Not Available134.058http://allccs.zhulab.cn/database/detail?ID=AllCCS00000361
Predicted Molecular Properties
PropertyValueSource
Water Solubility8.49 g/LALOGPS
logP-0.81ALOGPS
logP0.47ChemAxon
logS-1.4ALOGPS
pKa (Strongest Acidic)2.96ChemAxon
pKa (Strongest Basic)-1.9ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area90.95 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity48.92 m³·mol⁻¹ChemAxon
Polarizability18.06 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+143.18231661259
DarkChem[M-H]-141.20431661259
DeepCCS[M+H]+135.40830932474
DeepCCS[M-H]-133.01230932474
DeepCCS[M-2H]-168.0430932474
DeepCCS[M+Na]+142.66830932474
AllCCS[M+H]+141.832859911
AllCCS[M+H-H2O]+137.632859911
AllCCS[M+NH4]+145.632859911
AllCCS[M+Na]+146.732859911
AllCCS[M-H]-139.432859911
AllCCS[M+Na-2H]-139.832859911
AllCCS[M+HCOO]-140.332859911

Predicted Retention Times

Underivatized

Chromatographic MethodRetention TimeReference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. 2.38 minutes32390414
Predicted by Siyang on May 30, 20229.2084 minutes33406817
Predicted by Siyang using ReTip algorithm on June 8, 20223.07 minutes32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid659.5 seconds40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid288.0 seconds40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid74.7 seconds40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid165.4 seconds40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid46.9 seconds40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid250.3 seconds40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid295.3 seconds40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)80.7 seconds40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid611.4 seconds40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid290.5 seconds40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid784.2 seconds40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid206.5 seconds40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid180.4 seconds40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate596.2 seconds40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA184.7 seconds40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water156.4 seconds40023050

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
1,7-Dimethyluric acidCN1C(=O)NC2=C1C(=O)N(C)C(=O)N22487.3Standard polar33892256
1,7-Dimethyluric acidCN1C(=O)NC2=C1C(=O)N(C)C(=O)N22121.0Standard non polar33892256
1,7-Dimethyluric acidCN1C(=O)NC2=C1C(=O)N(C)C(=O)N22190.8Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
1,7-Dimethyluric acid,1TMS,isomer #1CN1C(=O)[NH]C2=C(C1=O)N(C)C(=O)N2[Si](C)(C)C1999.7Semi standard non polar33892256
1,7-Dimethyluric acid,1TMS,isomer #1CN1C(=O)[NH]C2=C(C1=O)N(C)C(=O)N2[Si](C)(C)C2240.9Standard non polar33892256
1,7-Dimethyluric acid,1TMS,isomer #1CN1C(=O)[NH]C2=C(C1=O)N(C)C(=O)N2[Si](C)(C)C2881.8Standard polar33892256
1,7-Dimethyluric acid,1TMS,isomer #2CN1C(=O)C2=C([NH]C(=O)N2C)N([Si](C)(C)C)C1=O1985.9Semi standard non polar33892256
1,7-Dimethyluric acid,1TMS,isomer #2CN1C(=O)C2=C([NH]C(=O)N2C)N([Si](C)(C)C)C1=O2248.6Standard non polar33892256
1,7-Dimethyluric acid,1TMS,isomer #2CN1C(=O)C2=C([NH]C(=O)N2C)N([Si](C)(C)C)C1=O2859.3Standard polar33892256
1,7-Dimethyluric acid,2TMS,isomer #1CN1C(=O)C2=C(N([Si](C)(C)C)C1=O)N([Si](C)(C)C)C(=O)N2C1985.9Semi standard non polar33892256
1,7-Dimethyluric acid,2TMS,isomer #1CN1C(=O)C2=C(N([Si](C)(C)C)C1=O)N([Si](C)(C)C)C(=O)N2C2286.7Standard non polar33892256
1,7-Dimethyluric acid,2TMS,isomer #1CN1C(=O)C2=C(N([Si](C)(C)C)C1=O)N([Si](C)(C)C)C(=O)N2C2470.8Standard polar33892256
1,7-Dimethyluric acid,1TBDMS,isomer #1CN1C(=O)[NH]C2=C(C1=O)N(C)C(=O)N2[Si](C)(C)C(C)(C)C2205.1Semi standard non polar33892256
1,7-Dimethyluric acid,1TBDMS,isomer #1CN1C(=O)[NH]C2=C(C1=O)N(C)C(=O)N2[Si](C)(C)C(C)(C)C2449.9Standard non polar33892256
1,7-Dimethyluric acid,1TBDMS,isomer #1CN1C(=O)[NH]C2=C(C1=O)N(C)C(=O)N2[Si](C)(C)C(C)(C)C2829.0Standard polar33892256
1,7-Dimethyluric acid,1TBDMS,isomer #2CN1C(=O)C2=C([NH]C(=O)N2C)N([Si](C)(C)C(C)(C)C)C1=O2203.7Semi standard non polar33892256
1,7-Dimethyluric acid,1TBDMS,isomer #2CN1C(=O)C2=C([NH]C(=O)N2C)N([Si](C)(C)C(C)(C)C)C1=O2454.8Standard non polar33892256
1,7-Dimethyluric acid,1TBDMS,isomer #2CN1C(=O)C2=C([NH]C(=O)N2C)N([Si](C)(C)C(C)(C)C)C1=O2810.5Standard polar33892256
1,7-Dimethyluric acid,2TBDMS,isomer #1CN1C(=O)C2=C(N([Si](C)(C)C(C)(C)C)C1=O)N([Si](C)(C)C(C)(C)C)C(=O)N2C2406.2Semi standard non polar33892256
1,7-Dimethyluric acid,2TBDMS,isomer #1CN1C(=O)C2=C(N([Si](C)(C)C(C)(C)C)C1=O)N([Si](C)(C)C(C)(C)C)C(=O)N2C2714.1Standard non polar33892256
1,7-Dimethyluric acid,2TBDMS,isomer #1CN1C(=O)C2=C(N([Si](C)(C)C(C)(C)C)C1=O)N([Si](C)(C)C(C)(C)C)C(=O)N2C2578.0Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 1,7-Dimethyluric acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-029l-0900000000-fa683b3e4ecb7c70f2062017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 1,7-Dimethyluric acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 1,7-Dimethyluric acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - 1,7-Dimethyluric acid LC-ESI-QFT , positive-QTOFsplash10-0002-0900000000-f40482c57d127e32f8e42020-07-21HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 1,7-Dimethyluric acid LC-ESI-QTOF 35V, positive-QTOFsplash10-0007-0900000000-6860551c1745ba41864f2020-07-21HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 1,7-Dimethyluric acid NA , positive-QTOFsplash10-0002-0900000000-c180cf8aed0912f88a752020-07-21HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 1,7-Dimethyluric acid LC-ESI-QFT , negative-QTOFsplash10-0002-0900000000-ae0b921d4ce14cd8443d2020-07-21HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 1,7-Dimethyluric acid LC-ESI-QTOF 35V, negative-QTOFsplash10-001i-0900000000-9d422231f3b705d6e8152020-07-21HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 1,7-Dimethyluric acid Orbitrap 4V, positive-QTOFsplash10-0002-0900000000-440ffa8e3cca49f55cc52020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 1,7-Dimethyluric acid Orbitrap 5V, positive-QTOFsplash10-0002-0900000000-9191d6a6a1abdd23d8112020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 1,7-Dimethyluric acid Orbitrap 5V, positive-QTOFsplash10-0002-0900000000-1b5e888daf17a0165e552020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 1,7-Dimethyluric acid Orbitrap 6V, positive-QTOFsplash10-0005-0900000000-df2cb96313fe3610cc442020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 1,7-Dimethyluric acid Orbitrap 7V, positive-QTOFsplash10-0007-0900000000-6234b012018c1ae4d86e2020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 1,7-Dimethyluric acid Orbitrap 9V, positive-QTOFsplash10-0006-1900000000-86334014f96303c723042020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 1,7-Dimethyluric acid Orbitrap 11V, positive-QTOFsplash10-0006-6900000000-ca9b5373df8e0ea8fcd32020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 1,7-Dimethyluric acid Orbitrap 13V, positive-QTOFsplash10-01bc-9300000000-7a850dc063e0bf5fd5fb2020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 1,7-Dimethyluric acid n/a 13V, positive-QTOFsplash10-0006-0900000000-0277172e5e710f4775de2020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 1,7-Dimethyluric acid n/a 13V, positive-QTOFsplash10-03di-6900000000-542cf592e0459e911f5c2020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 1,7-Dimethyluric acid n/a 13V, positive-QTOFsplash10-00xr-9000000000-db67735b192b87b601b32020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 1,7-Dimethyluric acid n/a 13V, positive-QTOFsplash10-000i-0900000000-e0b8225c7958cf0367cf2020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 1,7-Dimethyluric acid n/a 13V, positive-QTOFsplash10-03di-0900000000-8cd35e2b2191f4fb94a12020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 1,7-Dimethyluric acid n/a 13V, positive-QTOFsplash10-004s-3900000000-f3c613d69643e20758ce2020-07-22HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1,7-Dimethyluric acid 10V, Positive-QTOFsplash10-0002-0900000000-bd55edf6a44d0c64f3b12016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1,7-Dimethyluric acid 20V, Positive-QTOFsplash10-0002-0900000000-1ba40353172a8d8a0d532016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1,7-Dimethyluric acid 40V, Positive-QTOFsplash10-0002-9600000000-9845b1cfa11ec4dcced02016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1,7-Dimethyluric acid 10V, Negative-QTOFsplash10-0002-1900000000-45f918e65bf50b9c83ce2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1,7-Dimethyluric acid 20V, Negative-QTOFsplash10-0002-2900000000-683f1d7f14c8b26bd2cd2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1,7-Dimethyluric acid 40V, Negative-QTOFsplash10-05mp-9200000000-9022272eeb07eb313dfd2016-08-03Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-03FELIX labView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Blood
  • Feces
  • Urine
Tissue Locations
  • Kidney
  • Liver
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot Available
Normal
      Not Available
 details
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
UrineDetected and Quantified3.0 (2.38 - 6.7) umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal adenoma 		details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothColorectal Cancer details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer		 details
UrineDetected and Quantified20.0 (5.7-32.0) umol/mmol creatinineAdult (>18 years old)Both
Asthma		 details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal adenoma 		details
Associated Disorders and Diseases
Disease References
Colorectal cancer
  1. Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ]
  2. Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
Asthma
  1. Zydron M, Baranowski J, Baranowska I: Separation, pre-concentration, and HPLC analysis of methylxanthines in urine samples. J Sep Sci. 2004 Oct;27(14):1166-72. [PubMed:15537072 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB027886
KNApSAcK IDNot Available
Chemspider ID82720
KEGG Compound IDC16356
BioCyc IDCPD-12483
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound91611
PDB IDNot Available
ChEBI ID68449
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDMDB00000796
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Sinues B, Fanlo A, Mayayo E, Carcas C, Vicente J, Arenaz I, Cebollada A: CYP2A6 activity in a healthy Spanish population: effect of age, sex, smoking, and oral contraceptives. Hum Exp Toxicol. 2008 May;27(5):367-72. doi: 10.1177/0960327107082224. [PubMed:18715882 ]

Enzymes

Enzyme Details
1. Xanthine dehydrogenase/oxidase
General function:
Involved in oxidoreductase activity
Specific function:
Key enzyme in purine degradation. Catalyzes the oxidation of hypoxanthine to xanthine. Catalyzes the oxidation of xanthine to uric acid. Contributes to the generation of reactive oxygen species. Has also low oxidase activity towards aldehydes (in vitro).
Gene Name:
XDH
Uniprot ID:
P47989
Molecular weight:
146422.99
Reactions
Paraxanthine + Oxygen + Water → 1,7-Dimethyluric acid + Hydrogen peroxidedetails
Enzyme Details
2. Cytochrome P450 1A2
General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Most active in catalyzing 2-hydroxylation. Caffeine is metabolized primarily by cytochrome CYP1A2 in the liver through an initial N3-demethylation. Also acts in the metabolism of aflatoxin B1 and acetaminophen. Participates in the bioactivation of carcinogenic aromatic and heterocyclic amines. Catalizes the N-hydroxylation of heterocyclic amines and the O-deethylation of phenacetin.
Gene Name:
CYP1A2
Uniprot ID:
P05177
Molecular weight:
58406.915