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

$$$$
Download

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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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
Species of Origin
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 ]
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  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 ]