Record Information
Version1.0
Creation date2011-09-21 00:18:20 UTC
Update date2015-10-09 22:30:58 UTC
Primary IDFDB022712
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name1,3-Dimethyluric acid
Description1,3-Dimethyluric acid is a product of theophylline metabolism in man. 1,3-Dimethyluric acid 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, 4039734) [HMDB]
CAS Number944-73-0
Structure
Thumb
Synonyms
SynonymSource
OxytheophyllineChEBI
1,3-DimethylateGenerator
1,3-Dimethylic acidGenerator
1,3-DimethylurateHMDB
1,3-Dimethyluric acidhmdb
Predicted Properties
PropertyValueSource
Water Solubility8.69 g/LALOGPS
logP-0.74ALOGPS
logP-1.1ChemAxon
logS-1.4ALOGPS
pKa (Strongest Acidic)7.74ChemAxon
pKa (Strongest Basic)-5.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area81.75 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity55.42 m³·mol⁻¹ChemAxon
Polarizability17.74 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC7H8N4O3
IUPAC name1,3-dimethyl-2,3,6,7,8,9-hexahydro-1H-purine-2,6,8-trione
InChI IdentifierInChI=1S/C7H8N4O3/c1-10-4-3(8-6(13)9-4)5(12)11(2)7(10)14/h1-2H3,(H2,8,9,13)
InChI KeyOTSBKHHWSQYEHK-UHFFFAOYSA-N
Isomeric SMILESCN1C2=C(NC(=O)N2)C(=O)N(C)C1=O
Average Molecular Weight196.1634
Monoisotopic Molecular Weight196.059640142
Classification
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
Ontology
Disposition

Source:

Biological location:

Process

Naturally occurring process:

Role

Biological role:

Foods
  • Cocoa and cocoa products
  • Beverages:

    Physico-Chemical Properties - Experimental
    Physico-Chemical Properties - Experimental
    PropertyValueReference
    Physical stateSolid
    Physical DescriptionNot Available
    Mass CompositionNot Available
    Melting PointNot Available
    Boiling PointNot Available
    Experimental Water SolubilityNot Available
    Experimental logPNot Available
    Experimental pKaNot Available
    Isoelectric pointNot Available
    ChargeNot Available
    Optical RotationNot Available
    Spectroscopic UV DataNot Available
    DensityNot Available
    Refractive IndexNot Available
    Spectra
    Spectra
    Spectrum TypeDescriptionSplash KeyView
    Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00kr-1900000000-572b5e917ae798f7285dJSpectraViewer
    LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-01ot-1900000000-bbb1123e337bff47c690JSpectraViewer | MoNA
    LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-02mr-7900000000-fad7e7de9dee95b2d94bJSpectraViewer | MoNA
    LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-047i-6900000000-b985a0b78d94b88e5577JSpectraViewer | MoNA
    Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0900000000-6845b92ac4775760f4e2JSpectraViewer
    Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0005-0900000000-b12d2b6804ac76c77b2dJSpectraViewer
    Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-08gi-9400000000-3767a7fbda9ed867cbc5JSpectraViewer
    Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0900000000-f5b0e3ac88c5546199d9JSpectraViewer
    Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0900000000-f914e8dc73864e65caffJSpectraViewer
    Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-9300000000-ea85e3f13c8017afbbb3JSpectraViewer
    1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
    2D NMR[1H,13C] 2D NMR SpectrumNot AvailableJSpectraViewer
    ChemSpider ID63527
    ChEMBL IDCHEMBL795
    KEGG Compound IDNot Available
    Pubchem Compound ID70346
    Pubchem Substance IDNot Available
    ChEBI IDNot Available
    Phenol-Explorer IDNot Available
    DrugBank IDNot Available
    HMDB IDHMDB01857
    CRC / DFC (Dictionary of Food Compounds) IDNot Available
    EAFUS IDNot Available
    Dr. Duke IDNot Available
    BIGG IDNot Available
    KNApSAcK IDNot Available
    HET IDNot Available
    Food Biomarker OntologyNot Available
    VMH IDNot Available
    Flavornet IDNot Available
    GoodScent IDNot Available
    SuperScent IDNot Available
    Wikipedia IDNot Available
    Phenol-Explorer Metabolite IDNot Available
    Duplicate IDSNot Available
    Old DFC IDSNot Available
    Associated Foods
    FoodContent Range AverageReference
    FoodReference
    Biological Effects and Interactions
    Health Effects / BioactivitiesNot Available
    EnzymesNot Available
    PathwaysNot Available
    MetabolismNot Available
    BiosynthesisNot Available
    Organoleptic Properties
    FlavoursNot Available
    Files
    MSDSshow
    References
    Synthesis ReferenceNot Available
    General ReferenceNot Available
    Content Reference