Record Information
Version1.0
Creation date2011-09-21 00:24:46 UTC
Update date2015-10-09 22:32:39 UTC
Primary IDFDB023107
Secondary Accession NumbersNot Available
Chemical Information
FooDB 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 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, 9890610) [HMDB]
CAS Number708-79-2
Structure
Thumb
Synonyms
SynonymSource
1-MethylateGenerator
1-Methylic acidGenerator
1-MethylurateHMDB
Predicted Properties
PropertyValueSource
Water Solubility3.23 g/LALOGPS
logP-1.1ALOGPS
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 FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC6H6N4O3
IUPAC name1-methyl-2,3,6,7,8,9-hexahydro-1H-purine-2,6,8-trione
InChI IdentifierInChI=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
Isomeric SMILESCN1C(=O)NC2=C(NC(=O)N2)C1=O
Average Molecular Weight182.1368
Monoisotopic Molecular Weight182.043990078
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:

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, Positivesplash10-0far-2900000000-7c88ba8c892ca8263473JSpectraViewer
    LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-001i-0900000000-f2e42cd67ce1106bed63JSpectraViewer | MoNA
    LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-001i-0900000000-9fd2304504c5787dc255JSpectraViewer | MoNA
    LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0a4i-9000000000-6069b457c0c038edb8dfJSpectraViewer | MoNA
    LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0006-0900000000-f47eba015e7f8d9f21a7JSpectraViewer | MoNA
    Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0900000000-9fb7b528d968cab88bd3JSpectraViewer
    Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0059-1900000000-eb2d1569b5bdfeef979aJSpectraViewer
    Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000w-9300000000-065aa3463c121bf31312JSpectraViewer
    Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-1900000000-62dd716e79c8fa6f5ee0JSpectraViewer
    Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-3900000000-bf85a8ad5b7719f36abaJSpectraViewer
    Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9100000000-7db60439b29417bbbe0dJSpectraViewer
    1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
    2D NMR[1H,13C] 2D NMR SpectrumNot AvailableJSpectraViewer
    ChemSpider ID62926
    ChEMBL IDCHEMBL793
    KEGG Compound IDC16359
    Pubchem Compound ID69726
    Pubchem Substance IDNot Available
    ChEBI IDNot Available
    Phenol-Explorer IDNot Available
    DrugBank IDNot Available
    HMDB IDHMDB03099
    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
    Pathways
    NameSMPDB LinkKEGG Link
    Caffeine MetabolismSMP00028 map00232
    MetabolismNot Available
    BiosynthesisNot Available
    Organoleptic Properties
    FlavoursNot Available
    Files
    MSDSshow
    References
    Synthesis ReferenceNot Available
    General ReferenceNot Available
    Content Reference