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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2006-05-22 14:17:37 UTC
Update Date2017-12-07 01:48:12 UTC
HMDB IDHMDB0002123
Secondary Accession Numbers
  • HMDB02123
Metabolite Identification
Common Name1,3,7-Trimethyluric acid
Description1,3,7-Trimethyluric acid is a methyl derivative of uric acid, found occasionally in human urine. 1,3,7-Trimethyluracil 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 ).
Structure
Thumb
Synonyms
ValueSource
1,3,7-TrimethylurateChEBI
7,9-dihydro-1,3,7-Trimethyl-1H-purine-2,6,8(3H)-trioneChEBI
8-Oxy-caffeineChEBI
1,3,7-TrimethylateGenerator
1,3,7-Trimethylic acidGenerator
1,3, 7-Trimethyluric acidHMDB
1,3,7-Trimethyl-7,9-dihydro-1H-purine-2,6,8(3H)-trioneHMDB
2,6,8-Trihydroxy-1,3,7-trimethylpurineHMDB
8-Hydroxy-1,3,7-trimethyl-3,7-dihydro-1H-purine-2,6-dioneHMDB
Trimethyl uric acidHMDB
Chemical FormulaC8H10N4O3
Average Molecular Weight210.19
Monoisotopic Molecular Weight210.075290206
IUPAC Name1,3,7-trimethyl-2,3,6,7,8,9-hexahydro-1H-purine-2,6,8-trione
Traditional Name1,3,7-trimethyluric acid
CAS Registry Number5415-44-1
SMILES
CN1C(=O)NC2=C1C(=O)N(C)C(=O)N2C
InChI Identifier
InChI=1S/C8H10N4O3/c1-10-4-5(9-7(10)14)11(2)8(15)12(3)6(4)13/h1-3H3,(H,9,14)
InChI KeyBYXCFUMGEBZDDI-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as xanthines. These are purine derivatives with a ketone group conjugated at carbons 2 and 6 of the purine moiety.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganoheterocyclic compounds
Sub ClassImidazopyrimidines
Direct ParentXanthines
Alternative Parents
Substituents
  • Xanthine
  • 6-oxopurine
  • Purinone
  • Alkaloid or derivatives
  • Pyrimidone
  • N-substituted imidazole
  • Pyrimidine
  • Azole
  • Imidazole
  • Heteroaromatic compound
  • Vinylogous amide
  • Lactam
  • Urea
  • Azacycle
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effect

Health effect:

  Health condition:

Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

  Organ and components:

Source:

Process

Naturally occurring process:

  Biological process:

    Biochemical pathway:

Role

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility5.5 mg/mL at 15 °CNot Available
LogP-0.37GASPARI,F & BONATI,M (1987)
Predicted Properties
PropertyValueSource
Water Solubility28.3 g/LALOGPS
logP-0.49ALOGPS
logP-0.87ChemAxon
logS-0.87ALOGPS
pKa (Strongest Acidic)8.46ChemAxon
pKa (Strongest Basic)-5.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area72.96 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity60.32 m³·mol⁻¹ChemAxon
Polarizability19.82 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0udi-1900000000-7ceff209b1b0d4f92cf0View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, N/A (Annotated)splash10-03di-0090000000-c6489ab09ec74614db4cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, N/A (Annotated)splash10-001a-6900000000-ac2e74a460c865c0636bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, N/A (Annotated)splash10-067l-9100000000-cbac42dd288a8ef44fd8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-0006-0900000000-a9bff7d94cd5ffe280b9View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0udj-0900000000-5316637dfdcce19f087aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0090000000-153ea9ea8b4fe3692bfbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ik9-1790000000-2d17afbf34659471f524View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0m2a-4900000000-c783d40d7ed0c6ae44a9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0190000000-9858aab04a40f6286f93View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-1790000000-2089332ab35983ee2c77View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-066u-8900000000-53f14da0e8f43679f03fView in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Cytoplasm
Biofluid Locations
  • Blood
  • Feces
  • Urine
Tissue Location
  • Kidney
  • Liver
Pathways
NameSMPDB/PathwhizKEGG
Caffeine MetabolismPw000015Pw000015 greyscalePw000015 simpleMap00232
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot Available
Normal
    details
    BloodDetected but not Quantified Adult (>18 years old)Both
    Normal
    details
    BloodDetected but not Quantified Adult (>18 years old)Both
    Normal
    details
    UrineDetected and Quantified0.63 (0.63-0.93) umol/mmol creatinineAdult (>18 years old)BothNormal details
    Abnormal Concentrations
    BiofluidStatusValueAgeSexConditionReferenceDetails
    BloodDetected but not Quantified Adult (>18 years old)Both
    Colorectal adenoma
    details
    FecesDetected but not Quantified Adult (>18 years old)BothColorectal Cancer details
    FecesDetected but not Quantified Adult (>18 years old)BothColorectal Cancer details
    UrineDetected but not Quantified Adult (>18 years old)Both
    Colorectal adenoma
    details
    UrineDetected and Quantified2.19 (0.0-5.0) umol/mmol creatinineAdult (>18 years old)Both
    Asthma
    details
    Associated Disorders and Diseases
    Disease References
    Asthma
    1. Zydron M, Baranowski J, Baranowska I: Separation, pre-concentration, and HPLC analysis of methylxanthines in urine samples. J Sep Sci. 2004 Oct;27(14):1166-72. [PubMed:15537072 ]
    Associated OMIM IDs
    DrugBank IDNot Available
    DrugBank Metabolite IDDBMET00222
    Phenol Explorer Compound IDNot Available
    Phenol Explorer Metabolite IDNot Available
    FoodDB IDFDB022854
    KNApSAcK IDNot Available
    Chemspider ID71754
    KEGG Compound IDNot Available
    BioCyc IDNot Available
    BiGG IDNot Available
    Wikipedia LinkNot Available
    METLIN IDNot Available
    PubChem Compound79437
    PDB IDNot Available
    ChEBI ID691622
    References
    Synthesis ReferenceNot Available
    Material Safety Data Sheet (MSDS)Download (PDF)
    General References
    1. Morris GS, Simmonds HA, Davies PM: Use of biological fluids for the rapid diagnosis of potentially lethal inherited disorders of human purine and pyrimidine metabolism. Biomed Chromatogr. 1986 Jun;1(3):109-18. [PubMed:3506820 ]
    2. Safranow K, Machoy Z: Simultaneous determination of 16 purine derivatives in urinary calculi by gradient reversed-phase high-performance liquid chromatography with UV detection. J Chromatogr B Analyt Technol Biomed Life Sci. 2005 May 25;819(2):229-35. [PubMed:15833286 ]
    3. Safranow K: [Identification and quantitation of purine derivatives in urinary calculi as markers of abnormal purine metabolism by using high-performance liquid chromatography (HPLC)]. Ann Acad Med Stetin. 2000;46:35-49. [PubMed:11712316 ]
    4. Caubet MS, Comte B, Brazier JL: Determination of urinary 13C-caffeine metabolites by liquid chromatography-mass spectrometry: the use of metabolic ratios to assess CYP1A2 activity. J Pharm Biomed Anal. 2004 Feb 4;34(2):379-89. [PubMed:15013152 ]