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Showing NP-Card for 1-Methyluric acid (NP0001035)

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Record Information
Version2.0
Created at2006-05-22 15:12:32 UTC
Updated at2021-10-07 20:38:48 UTC
NP-MRD IDNP0001035
Secondary Accession NumbersNone
Natural Product Identification
Common Name1-Methyluric acid
Description1-Methyluric acid is one of the three main theophylline metabolites in man. 1-Methyluric acid is one of the purine components in urinary calculi. Methylated purines originate from the metabolism of methylxanthines (caffeine, theophylline, and theobromine). Methyluric acids can be distinguished from uric acid via 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 superfamily, 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 , 4039734 , 9890610 ).
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0001035 (1-Methyluric acid)


  Mrv1652309042000282D          

 13 14  0  0  0  0            999 V2000
    2.7845    0.6979    0.0000 C   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    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556   -0.1271    0.0000 O   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    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435    2.1904    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6284    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4534    1.5229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435    0.8555    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    2.3479    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7845    2.3479    0.0000 O   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
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
  5 10  1  0  0  0  0
  6 11  1  0  0  0  0
 11 12  1  0  0  0  0
  2 12  1  0  0  0  0
 12 13  2  0  0  0  0
M  END
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3D MOL for NP0001035 (1-Methyluric acid)

HMDB0003099
     RDKit          3D
1-Methyluric acid
 19 20  0  0  0  0  0  0  0  0999 V2000
    2.9923   -0.2113    0.0486 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5517    0.0573   -0.0077 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0729    1.2929   -0.2344 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9106    2.2202   -0.3981 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2453    1.5764   -0.2928 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1822    0.6244   -0.1251 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5367    0.5958   -0.1272 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9390   -0.6796    0.1021 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1557   -1.0213    0.1576 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8363   -1.4079    0.2400 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7231   -0.6568    0.1097 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6440   -0.9208    0.1648 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0284   -2.1075    0.3821 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2737   -0.5626    1.0826 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5188    0.7201   -0.1560 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2108   -1.0422   -0.6234 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6026    2.5432   -0.4701 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1639    1.4280   -0.2815 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8182   -2.4483    0.4288 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
 11 12  1  0
 12 13  2  0
 12  2  1  0
 11  6  2  0
  1 14  1  0
  1 15  1  0
  1 16  1  0
  5 17  1  0
  7 18  1  0
 10 19  1  0
M  END
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3D SDF for NP0001035 (1-Methyluric acid)


  Mrv1652309042000282D          

 13 14  0  0  0  0            999 V2000
    2.7845    0.6979    0.0000 C   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    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556   -0.1271    0.0000 O   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    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435    2.1904    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6284    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4534    1.5229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435    0.8555    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    2.3479    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7845    2.3479    0.0000 O   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
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
  5 10  1  0  0  0  0
  6 11  1  0  0  0  0
 11 12  1  0  0  0  0
  2 12  1  0  0  0  0
 12 13  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0001035

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CN1C(=O)NC2=C(NC(=O)N2)C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C6H6N4O3/c1-10-4(11)2-3(9-6(10)13)8-5(12)7-2/h1H3,(H,9,13)(H2,7,8,12)

> <INCHI_KEY>
QFDRTQONISXGJA-UHFFFAOYSA-N

> <FORMULA>
C6H6N4O3

> <MOLECULAR_WEIGHT>
182.1368

> <EXACT_MASS>
182.043990078

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
19

> <JCHEM_AVERAGE_POLARIZABILITY>
15.725862137209987

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
-1.15

> <JCHEM_LOGP>
-1.32051687

> <ALOGPS_LOGS>
-1.75

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.880095047769107

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.671819121930137

> <JCHEM_PKA_STRONGEST_BASIC>
-6.168799154143619

> <JCHEM_POLAR_SURFACE_AREA>
90.54

> <JCHEM_REFRACTIVITY>
50.5253

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.23e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1-methyluric acid

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for NP0001035 (1-Methyluric acid)

HMDB0003099
     RDKit          3D
1-Methyluric acid
 19 20  0  0  0  0  0  0  0  0999 V2000
    2.9923   -0.2113    0.0486 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5517    0.0573   -0.0077 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0729    1.2929   -0.2344 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9106    2.2202   -0.3981 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2453    1.5764   -0.2928 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1822    0.6244   -0.1251 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5367    0.5958   -0.1272 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9390   -0.6796    0.1021 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1557   -1.0213    0.1576 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8363   -1.4079    0.2400 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7231   -0.6568    0.1097 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6440   -0.9208    0.1648 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0284   -2.1075    0.3821 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2737   -0.5626    1.0826 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5188    0.7201   -0.1560 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2108   -1.0422   -0.6234 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6026    2.5432   -0.4701 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1639    1.4280   -0.2815 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8182   -2.4483    0.4288 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
 11 12  1  0
 12 13  2  0
 12  2  1  0
 11  6  2  0
  1 14  1  0
  1 15  1  0
  1 16  1  0
  5 17  1  0
  7 18  1  0
 10 19  1  0
M  END
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PDB for NP0001035 (1-Methyluric 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       5.198   1.303   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0       3.864   2.073   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0       2.530   1.303   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       2.530  -0.237   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       1.197   2.073   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.197   3.613   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0      -0.268   4.089   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0      -1.173   2.843   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -2.713   2.843   0.000  0.00  0.00           O+0
HETATM   10  N   UNK     0      -0.268   1.597   0.000  0.00  0.00           N+0
HETATM   11  N   UNK     0       2.530   4.383   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0       3.864   3.613   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       5.198   4.383   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   12                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   10                                                  
CONECT    6    5    7   11                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8    5                                                       
CONECT   11    6   12                                                       
CONECT   12   11    2   13                                                  
CONECT   13   12                                                            
MASTER        0    0    0    0    0    0    0    0   13    0   28    0
END
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3D PDB for NP0001035 (1-Methyluric acid)

COMPND    HMDB0003099
HETATM    1  C1  UNL     1       2.992  -0.211   0.049  1.00  0.00           C  
HETATM    2  N1  UNL     1       1.552   0.057  -0.008  1.00  0.00           N  
HETATM    3  C2  UNL     1       1.073   1.293  -0.234  1.00  0.00           C  
HETATM    4  O1  UNL     1       1.911   2.220  -0.398  1.00  0.00           O  
HETATM    5  N2  UNL     1      -0.245   1.576  -0.293  1.00  0.00           N  
HETATM    6  C3  UNL     1      -1.182   0.624  -0.125  1.00  0.00           C  
HETATM    7  N3  UNL     1      -2.537   0.596  -0.127  1.00  0.00           N  
HETATM    8  C4  UNL     1      -2.939  -0.680   0.102  1.00  0.00           C  
HETATM    9  O2  UNL     1      -4.156  -1.021   0.158  1.00  0.00           O  
HETATM   10  N4  UNL     1      -1.836  -1.408   0.240  1.00  0.00           N  
HETATM   11  C5  UNL     1      -0.723  -0.657   0.110  1.00  0.00           C  
HETATM   12  C6  UNL     1       0.644  -0.921   0.165  1.00  0.00           C  
HETATM   13  O3  UNL     1       1.028  -2.107   0.382  1.00  0.00           O  
HETATM   14  H1  UNL     1       3.274  -0.563   1.083  1.00  0.00           H  
HETATM   15  H2  UNL     1       3.519   0.720  -0.156  1.00  0.00           H  
HETATM   16  H3  UNL     1       3.211  -1.042  -0.623  1.00  0.00           H  
HETATM   17  H4  UNL     1      -0.603   2.543  -0.470  1.00  0.00           H  
HETATM   18  H5  UNL     1      -3.164   1.428  -0.281  1.00  0.00           H  
HETATM   19  H6  UNL     1      -1.818  -2.448   0.429  1.00  0.00           H  
CONECT    1    2   14   15   16
CONECT    2    3   12
CONECT    3    4    4    5
CONECT    5    6   17
CONECT    6    7   11   11
CONECT    7    8   18
CONECT    8    9    9   10
CONECT   10   11   19
CONECT   11   12
CONECT   12   13   13
END
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SMILES for NP0001035 (1-Methyluric acid)

CN1C(=O)NC2=C(NC(=O)N2)C1=O
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INCHI for NP0001035 (1-Methyluric acid)

InChI=1S/C6H6N4O3/c1-10-4(11)2-3(9-6(10)13)8-5(12)7-2/h1H3,(H,9,13)(H2,7,8,12)
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View in JSmol
Synonyms
ValueSource
1-MethylateGenerator
1-Methylic acidGenerator
1-MethylurateHMDB
Chemical FormulaC6H6N4O3
Average Mass182.1368 Da
Monoisotopic Mass182.04399 Da
IUPAC Name1-methyl-2,3,6,7,8,9-hexahydro-1H-purine-2,6,8-trione
Traditional Name1-methyluric acid
CAS Registry Number708-79-2
SMILES
CN1C(=O)NC2=C(NC(=O)N2)C1=O
InChI Identifier
InChI=1S/C6H6N4O3/c1-10-4(11)2-3(9-6(10)13)8-5(12)7-2/h1H3,(H,9,13)(H2,7,8,12)
InChI KeyQFDRTQONISXGJA-UHFFFAOYSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 600 MHz, 5%_DMSO, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, 5%_DMSO, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
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Amelanchier alnifoliaFooDB
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Anethum graveolensFooDB
Angelica keiskeiFooDB
Annona cherimolaFooDB
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Annona reticulataFooDB
Annona squamosaFooDB
Anthriscus cerefoliumFooDB
Apium graveolensFooDB
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Apium graveolens var. rapaceumFooDB
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Arachis hypogaeaFooDB
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Artemisia vulgarisFooDB
Artocarpus altilisFooDB
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Auricularia auricula-judaeFooDB
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Avena sativa L.FooDB
Averrhoa carambolaFooDB
Basella albaFooDB
Benincasa hispidaFooDB
Bertholletia excelsaFooDB
Beta vulgarisFooDB
Beta vulgaris ssp. ciclaFooDB
Borago officinalisFooDB
Brassica alboglabraFooDB
Brassica junceaFooDB
Brassica napusFooDB
Brassica napus var. napusFooDB
Brassica oleraceaFooDB
Brassica oleracea var. botrytisFooDB
Brassica oleracea var. capitataFooDB
Brassica oleracea var. gemmiferaFooDB
Brassica oleracea var. gongylodesFooDB
Brassica oleracea var. italicaFooDB
Brassica oleracea var. sabaudaFooDB
Brassica oleracea var. viridisFooDB
Brassica rapaFooDB
Brassica rapa ssp. chinensisFooDB
Brassica rapa var. pekinensisFooDB
Brassica rapa var. rapaFooDB
Brassica ruvoFooDB
Brosimum alicastrumFooDB
Byrsonima crassifoliaFooDB
Cajanus cajanFooDB
Canarium ovatumFooDB
Cannabis sativaCannabisDB
      Not Available
Cantharellus cibariusFooDB
Capparis spinosaFooDB
Capsicum annuumFooDB
Capsicum annuum L.FooDB
Capsicum annuum var. annuumFooDB
Capsicum chinenseFooDB
Capsicum pubescensFooDB
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Carissa macrocarpaFooDB
Carthamus tinctoriusFooDB
Carum carviFooDB
CaryaFooDB
Carya illinoinensisFooDB
CastaneaFooDB
Castanea crenataFooDB
Castanea mollissimaFooDB
Castanea sativaFooDB
Ceratonia siliquaFooDB
Chamaemelum nobileFooDB
Chamerion angustifoliumFooDB
Chenopodium albumFooDB
Chenopodium quinoaFooDB
Chrysanthemum coronariumFooDB
Cicer arietinumFooDB
Cichorium endiviaFooDB
Cichorium intybusFooDB
CinnamomumFooDB
Cinnamomum aromaticumFooDB
Cinnamomum verumFooDB
CirsiumFooDB
Citrullus lanatusFooDB
Citrus ×limon (L.) Burm. f. (pro sp.)FooDB
Citrus aurantiifoliaFooDB
Citrus latifoliaFooDB
Citrus limonFooDB
Citrus maximaFooDB
Citrus paradisiFooDB
Citrus reticulataFooDB
Citrus X sinensis (L.) Osbeck (pro. sp.)FooDB
Cocos nuciferaFooDB
Coffea arabica L.FooDB
Coffea canephoraFooDB
Colocasia esculentaFooDB
Corchorus olitoriusFooDB
Coriandrum sativum L.FooDB
CorylusFooDB
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Crateva religiosaFooDB
Crocus sativusFooDB
Cucumis meloFooDB
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CucurbitaFooDB
Cucurbita maximaFooDB
Cucurbita moschataFooDB
Cuminum cyminumFooDB
Curcuma longaFooDB
Cydonia oblongaFooDB
Cymbopogon citratusFooDB
Cynara cardunculusFooDB
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Daucus carotaFooDB
Daucus carota ssp. sativusFooDB
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Dysphania ambrosioidesFooDB
ElaeisFooDB
Eleocharis dulcisFooDB
Elettaria cardamomumFooDB
Empetrum nigrumFooDB
Eragrostis tefFooDB
Eriobotrya japonicaFooDB
Eruca vesicaria subsp. SativaFooDB
Eugenia javanicaFooDB
Eugenia unifloraFooDB
Eutrema japonicumFooDB
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Fagopyrum tataricumFooDB
FagusFooDB
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Ficus caricaFooDB
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Foeniculum vulgareFooDB
Fragaria x ananassaFooDB
Garcinia mangostanaFooDB
Gaylussacia baccataFooDB
Ginkgo bilobaFooDB
Glycine maxFooDB
GossypiumFooDB
Grifola frondosaFooDB
Hedysarum alpinumFooDB
Helianthus annuus L.FooDB
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Hibiscus sabbariffaFooDB
Hippophae rhamnoidesFooDB
Hordeum vulgareFooDB
Hyssopus officinalis L.FooDB
Illicium verumFooDB
Ipomoea aquaticaFooDB
Ipomoea batatasFooDB
JuglansFooDB
Juglans ailanthifoliaFooDB
Juglans cinereaFooDB
Juglans nigra L.FooDB
Juglans regiaFooDB
Lablab purpureusFooDB
Lactuca sativaFooDB
Lagenaria sicerariaFooDB
Lathyrus sativusFooDB
Laurus nobilis L.FooDB
Lens culinarisFooDB
Lentinus edodesFooDB
Lepidium sativumFooDB
Levisticum officinaleFooDB
Linum usitatissimumFooDB
Litchi chinensisFooDB
Luffa aegyptiacaFooDB
LupinusFooDB
Lupinus albusFooDB
MacadamiaFooDB
Macadamia tetraphyllaFooDB
Malpighia emarginataFooDB
MalusFooDB
Malus pumilaFooDB
Mammea americanaFooDB
Mangifera indicaFooDB
Manihot esculentaFooDB
Manilkara zapotaFooDB
Maranta arundinaceaFooDB
Matricaria recutitaFooDB
Matteuccia struthiopterisFooDB
Medicago sativaFooDB
Melissa officinalis L.FooDB
MenthaFooDB
Mentha aquaticaFooDB
Mentha arvensisFooDB
Mentha spicataFooDB
Mentha x piperitaFooDB
Mespilus germanicaFooDB
Metroxylon saguFooDB
Momordica charantiaFooDB
MorchellaceaeFooDB
Morella rubraFooDB
Moringa oleiferaFooDB
MorusFooDB
Morus nigraFooDB
Mus musculusLOTUS Database
Musa acuminataFooDB
Musa x paradisiacaFooDB
MyricaFooDB
Myristica fragransFooDB
NelumboFooDB
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Nephelium lappaceumFooDB
Nuphar luteaFooDB
Ocimum basilicumFooDB
Oenothera biennisFooDB
Olea europaeaFooDB
OpuntiaFooDB
Opuntia cochenilliferaFooDB
Opuntia macrorhizaFooDB
Origanum majoranaFooDB
Origanum onitesFooDB
Origanum vulgareFooDB
Origanum X majoricumFooDB
Oryza rufipogonFooDB
Oryza sativaFooDB
Pachyrhizus erosusFooDB
Panax ginsengFooDB
Pangium eduleFooDB
Panicum miliaceumFooDB
Passiflora edulisFooDB
Pastinaca sativaFooDB
Pediomelum esculentumFooDB
Perideridia oreganaFooDB
Persea americanaFooDB
Petasites japonicusFooDB
Petroselinum crispumFooDB
Phaseolus coccineusFooDB
Phaseolus lunatusFooDB
Phaseolus vulgarisFooDB
Phoenix dactyliferaFooDB
Photinia melanocarpaFooDB
Phyllostachys edulisFooDB
PhysalisFooDB
Physalis philadelphica var. immaculataFooDB
Phytolacca americanaFooDB
Pimenta dioicaFooDB
Pimpinella anisumFooDB
PinusFooDB
Pinus edulisFooDB
Piper nigrum L.FooDB
Pistacia veraFooDB
Pisum sativumFooDB
Pleurotus ostreatusFooDB
Polygonum alpinumFooDB
Portulaca oleraceaFooDB
Pouteria sapotaFooDB
Prunus armeniacaFooDB
Prunus aviumFooDB
Prunus avium L.FooDB
Prunus cerasusFooDB
Prunus domesticaFooDB
Prunus dulcisFooDB
Prunus persicaFooDB
Prunus persica var. nucipersicaFooDB
Prunus persica var. persicaFooDB
Prunus tomentosaFooDB
Prunus virginianaFooDB
Psidium cattleianumFooDB
Psidium guajavaFooDB
Psophocarpus tetragonolobusFooDB
Punica granatumFooDB
Pyrus communisFooDB
Pyrus pyrifoliaFooDB
QuercusFooDB
Raphanus sativusFooDB
Raphanus sativus var. longipinnatusFooDB
Raphanus sativus var. sativusFooDB
Rheum rhabarbarumFooDB
Ribes aureumFooDB
Ribes glandulosumFooDB
Ribes nigrumFooDB
Ribes rubrumFooDB
Ribes uva-crispaFooDB
RosaFooDB
Rubus arcticusFooDB
Rubus chamaemorusFooDB
Rubus idaeusFooDB
Rubus occidentalisFooDB
Rubus spectabilisFooDB
RumexFooDB
Rumex acetosaFooDB
Rumex articusFooDB
Sagittaria latifoliaFooDB
Salix pulchraFooDB
Salvia elegansFooDB
Salvia hispanicaFooDB
Salvia officinalisFooDB
Salvia rosmarinusFooDB
Sambucus nigraFooDB
Sambucus nigra L.FooDB
Satureja hortensis L.FooDB
Satureja montanaFooDB
Scorzonera hispanicaFooDB
Secale cerealeFooDB
Sechium eduleFooDB
Sesamum indicumFooDB
Sesbania bispinosaFooDB
Sinapis albaFooDB
SisymbriumFooDB
Solanum lycopersicumFooDB
Solanum lycopersicum var. cerasiformeFooDB
Solanum lycopersicum var. lycopersicumFooDB
Solanum melongenaFooDB
Solanum quitoenseFooDB
Solanum tuberosumFooDB
Sorbus aucupariaFooDB
Sorghum bicolorFooDB
Spinacia oleraceaFooDB
Syzygium aromaticumFooDB
Syzygium cuminiFooDB
Syzygium jambosFooDB
Tamarindus indicaFooDB
Taraxacum officinaleFooDB
Tetragonia tetragonioidesFooDB
ThelespermaFooDB
Thymus pulegioidesFooDB
Thymus vulgarisFooDB
Tilia cordataFooDB
Tilia L.FooDB
Tragopogon porrifoliusFooDB
Trigonella foenum-graecumFooDB
TriticumFooDB
Triticum aestivumFooDB
Triticum durumFooDB
Triticum speltaFooDB
Triticum turanicumFooDB
Typha angustifoliaFooDB
VacciniumFooDB
Vaccinium angustifoliumFooDB
Vaccinium angustifolium X Vaccinium corymbosumFooDB
Vaccinium arboreumFooDB
Vaccinium corymbosumFooDB
Vaccinium deliciosumFooDB
Vaccinium elliottiiFooDB
Vaccinium macrocarponFooDB
Vaccinium myrtilloidesFooDB
Vaccinium myrtillusFooDB
Vaccinium ovalifoliumFooDB
Vaccinium ovatumFooDB
Vaccinium oxycoccosFooDB
Vaccinium parvifoliumFooDB
Vaccinium reticulatumFooDB
Vaccinium stamineumFooDB
Vaccinium uliginosumFooDB
Vaccinium vitis-idaeaFooDB
Valerianella locustaFooDB
VanillaFooDB
Verbena officinalisFooDB
Viburnum eduleFooDB
Vicia fabaFooDB
Vigna aconitifoliaFooDB
Vigna angularisFooDB
Vigna mungoFooDB
Vigna radiataFooDB
Vigna umbellataFooDB
Vigna unguiculataFooDB
Vigna unguiculata ssp. cylindricaFooDB
Vigna unguiculata ssp. unguiculataFooDB
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VitisFooDB
Vitis aestivalisFooDB
Vitis labruscaFooDB
Vitis rotundifoliaFooDB
Vitis vinifera L.FooDB
Xanthosoma sagittifoliumFooDB
Zea mays L.FooDB
Zingiber officinaleFooDB
ZizaniaFooDB
Zizania aquaticaFooDB
Ziziphus zizyphusFooDB
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
  • Pyrimidine
  • Azole
  • Imidazole
  • Heteroaromatic compound
  • Vinylogous amide
  • Lactam
  • Urea
  • Azacycle
  • Hydrocarbon derivative
  • Organic oxide
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Organopnictogen compound
  • Organic oxygen 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 Solubility5 mg/mLNot Available
LogP-0.57Gaspari, 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 Solubility3.23 g/LALOGPS
logP-1.2ALOGPS
logP-1.3ChemAxon
logS-1.8ALOGPS
pKa (Strongest Acidic)7.67ChemAxon
pKa (Strongest Basic)-6.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area90.54 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity50.53 m³·mol⁻¹ChemAxon
Polarizability15.73 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0003099
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB023107
KNApSAcK IDNot Available
Chemspider ID62926
KEGG Compound IDC16359
BioCyc IDCPD-14119
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID2821
PubChem Compound69726
PDB IDNot Available
ChEBI ID68441
Good Scents IDNot Available
References
General References
  1. Knoppert DC, Spino M, Beck R, Thiessen JJ, MacLeod SM: Cystic fibrosis: enhanced theophylline metabolism may be linked to the disease. Clin Pharmacol Ther. 1988 Sep;44(3):254-64. [PubMed:3046811 ]
  2. Tateishi T, Asoh M, Yamaguchi A, Yoda T, Okano YJ, Koitabashi Y, Kobayashi S: Developmental changes in urinary elimination of theophylline and its metabolites in pediatric patients. Pediatr Res. 1999 Jan;45(1):66-70. [PubMed:9890610 ]
  3. Nakano K, Assenza SP, Brown PR: Reversed-phase liquid chromatographic investigation of UV-absorbing low-molecular-weight compounds in saliva. J Chromatogr. 1982 Dec 10;233:51-60. [PubMed:7161362 ]
  4. Grygiel JJ, Wing LM, Farkas J, Birkett DJ: Effects of allopurinol on theophylline metabolism and clearance. Clin Pharmacol Ther. 1979 Nov;26(5):660-7. [PubMed:498708 ]
  5. Kilbane AJ, Silbart LK, Manis M, Beitins IZ, Weber WW: Human N-acetylation genotype determination with urinary caffeine metabolites. Clin Pharmacol Ther. 1990 Apr;47(4):470-7. [PubMed:2328555 ]
  6. Miller CA, Slusher LB, Vesell ES: Polymorphism of theophylline metabolism in man. J Clin Invest. 1985 May;75(5):1415-25. [PubMed:4039734 ]