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Showing Compound 3-Methyluric acid (FDB022770)

Record Information
Version1.0
Creation date2011-09-21 00:19:19 UTC
Update date2015-07-21 06:57:21 UTC
Primary IDFDB022770
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name3-Methyluric acid
Description3-Methyluric acid is a methyl derivative of uric acid, found occasionally in human urine. 3-Methyluracil 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) [HMDB]
CAS Number605-99-2
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
3-MethylateGenerator
3-Methylic acidGenerator
3-Methyl-2,6,8-trioxopurineHMDB
3-Methyl-7,9-dihydro-3H-purine-2,6,8-trioneHMDB
3-MethylurateHMDB
4,9-dihydro-3-Methyl-1H-purine-2,6,8(3H)-trioneHMDB
4,9-Dihydro-3-methyl-1H-purine-2,6,8(3H)-trionehmdb
Predicted Properties
PropertyValueSource
Water Solubility3.79 g/LALOGPS
logP-1ALOGPS
logP-1.3ChemAxon
logS-1.7ALOGPS
pKa (Strongest Acidic)7.66ChemAxon
pKa (Strongest Basic)-6.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area90.54 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity50.53 m³·mol⁻¹ChemAxon
Polarizability15.62 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC6H6N4O3
IUPAC name3-methyl-2,3,6,7,8,9-hexahydro-1H-purine-2,6,8-trione
InChI IdentifierInChI=1S/C6H6N4O3/c1-10-3-2(7-5(12)8-3)4(11)9-6(10)13/h1H3,(H2,7,8,12)(H,9,11,13)
InChI KeyODCYDGXXCHTFIR-UHFFFAOYSA-N
Isomeric SMILESCN1C2=C(NC(=O)N2)C(=O)NC1=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
    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
    EI-MS/GC-MS
    TypeDescriptionSplash KeyView
    Predicted GC-MS3-Methyluric acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0w39-1900000000-4493eeacfd3b31bf832aSpectrum
    Predicted GC-MS3-Methyluric acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
    Predicted GC-MS3-Methyluric acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
    MS/MS
    TypeDescriptionSplash KeyView
    MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-001i-1900000000-7bce57917a5f609da3ba2021-09-20View Spectrum
    MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-0006-9800000000-279d680e2ffcb04ad7e02021-09-20View Spectrum
    MS/MSLC-MS/MS Spectrum - 30V, Negativesplash10-0006-9100000000-3bf2f0fa51aa58bcedae2021-09-20View Spectrum
    MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-c658507237f6f9aa6a6d2021-09-20View Spectrum
    MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-001i-0900000000-833bbd5ce51f926796182021-09-20View Spectrum
    MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-0a4i-9000000000-ff93732db21ada6d10792021-09-20View Spectrum
    MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-0a4i-9200000000-48d667ee9b881e1f49cd2021-09-20View Spectrum
    MS/MSLC-MS/MS Spectrum - 0V, Positivesplash10-001i-0900000000-4f69861b810b8c8e29322021-09-20View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0900000000-a68b56cfc61693cc09d32016-08-01View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-1900000000-70450e20782b787888042016-08-01View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0le9-9400000000-9a16030e87688510dd072016-08-01View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0900000000-064ba09247119134215d2016-08-03View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001r-2900000000-440959c7239da4a5e5cc2016-08-03View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9300000000-b3af7b9a39ec8e73e1c52016-08-03View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0900000000-fa33d1f90dc5e1d6cf642021-09-22View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-0900000000-1be9499dfc9068f23ee72021-09-22View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0rki-9100000000-ab442babdbe0af347c272021-09-22View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0900000000-edc51048cb5eee9df5e12021-09-23View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-0900000000-c78227a2eb31d6e894492021-09-23View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-dceeb3684f917d3b370e2021-09-23View Spectrum
    NMRNot Available
    ChemSpider ID11311
    ChEMBL IDCHEMBL791
    KEGG Compound IDNot Available
    Pubchem Compound ID11804
    Pubchem Substance IDNot Available
    ChEBI IDNot Available
    Phenol-Explorer IDNot Available
    DrugBank IDNot Available
    HMDB IDHMDB01970
    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
    MSDSNot Available
    References
    Synthesis ReferenceNot Available
    General ReferenceNot Available
    Content ReferenceNot Available